Solvent

Solvent

Overview
A solvent is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute
Solution
In chemistry, a solution is a homogeneous mixture composed of only one phase. In such a mixture, a solute is dissolved in another substance, known as a solvent. The solvent does the dissolving.- Types of solutions :...

, resulting in a solution
Solution
In chemistry, a solution is a homogeneous mixture composed of only one phase. In such a mixture, a solute is dissolved in another substance, known as a solvent. The solvent does the dissolving.- Types of solutions :...

 that is soluble in a certain volume of solvent at a specified temperature
Temperature
Temperature is a physical property of matter that quantitatively expresses the common notions of hot and cold. Objects of low temperature are cold, while various degrees of higher temperatures are referred to as warm or hot...

. Common uses for organic
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 solvents are in dry cleaning
Dry cleaning
Dry cleaning is any cleaning process for clothing and textiles using a chemical solvent other than water. The solvent used is typically tetrachloroethylene , abbreviated "perc" in the industry and "dry-cleaning fluid" by the public...

 (e.g., tetrachloroethylene
Tetrachloroethylene
Tetrachloroethylene, also known under its systematic name tetrachloroethene and many other names, is a chlorocarbon with the formula Cl2C=CCl2. It is a colourless liquid widely used for dry cleaning of fabrics, hence it is sometimes called "dry-cleaning fluid." It has a sweet odor detectable by...

), as a paint thinner
Paint thinner
A paint thinner is a solvent used to thin oil-based paints or clean up after their use, although all such solvents have other uses. Commercially, "paint thinner" is usually a name for mineral spirits.Products used as paint thinners include:*Mineral spirits...

 (e.g., toluene, turpentine), as nail polish removers and glue solvents (acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...

, methyl acetate
Methyl acetate
Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is normally a flammable liquid with a characteristic, pleasant smell like certain glues or nail polish removers. Methyl acetate has characteristics very similar...

, ethyl acetate
Ethyl acetate
Ethyl acetate is the organic compound with the formula CH3COOCH2CH3. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and cigarettes...

), in spot removers (e.g., hexane
Hexane
Hexane is a hydrocarbon with the chemical formula C6H14; that is, an alkane with six carbon atoms.The term may refer to any of four other structural isomers with that formula, or to a mixture of them. In the IUPAC nomenclature, however, hexane is the unbranched isomer ; the other four structures...

, petrol ether), in detergents (citrus terpenes), in perfume
Perfume
Perfume is a mixture of fragrant essential oils and/or aroma compounds, fixatives, and solvents used to give the human body, animals, objects, and living spaces "a pleasant scent"...

s (ethanol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...

), and nail polish, (part of how it stays on nails) and in chemical synthesis.
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Encyclopedia
A solvent is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute
Solution
In chemistry, a solution is a homogeneous mixture composed of only one phase. In such a mixture, a solute is dissolved in another substance, known as a solvent. The solvent does the dissolving.- Types of solutions :...

, resulting in a solution
Solution
In chemistry, a solution is a homogeneous mixture composed of only one phase. In such a mixture, a solute is dissolved in another substance, known as a solvent. The solvent does the dissolving.- Types of solutions :...

 that is soluble in a certain volume of solvent at a specified temperature
Temperature
Temperature is a physical property of matter that quantitatively expresses the common notions of hot and cold. Objects of low temperature are cold, while various degrees of higher temperatures are referred to as warm or hot...

. Common uses for organic
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 solvents are in dry cleaning
Dry cleaning
Dry cleaning is any cleaning process for clothing and textiles using a chemical solvent other than water. The solvent used is typically tetrachloroethylene , abbreviated "perc" in the industry and "dry-cleaning fluid" by the public...

 (e.g., tetrachloroethylene
Tetrachloroethylene
Tetrachloroethylene, also known under its systematic name tetrachloroethene and many other names, is a chlorocarbon with the formula Cl2C=CCl2. It is a colourless liquid widely used for dry cleaning of fabrics, hence it is sometimes called "dry-cleaning fluid." It has a sweet odor detectable by...

), as a paint thinner
Paint thinner
A paint thinner is a solvent used to thin oil-based paints or clean up after their use, although all such solvents have other uses. Commercially, "paint thinner" is usually a name for mineral spirits.Products used as paint thinners include:*Mineral spirits...

 (e.g., toluene, turpentine), as nail polish removers and glue solvents (acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...

, methyl acetate
Methyl acetate
Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is normally a flammable liquid with a characteristic, pleasant smell like certain glues or nail polish removers. Methyl acetate has characteristics very similar...

, ethyl acetate
Ethyl acetate
Ethyl acetate is the organic compound with the formula CH3COOCH2CH3. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and cigarettes...

), in spot removers (e.g., hexane
Hexane
Hexane is a hydrocarbon with the chemical formula C6H14; that is, an alkane with six carbon atoms.The term may refer to any of four other structural isomers with that formula, or to a mixture of them. In the IUPAC nomenclature, however, hexane is the unbranched isomer ; the other four structures...

, petrol ether), in detergents (citrus terpenes), in perfume
Perfume
Perfume is a mixture of fragrant essential oils and/or aroma compounds, fixatives, and solvents used to give the human body, animals, objects, and living spaces "a pleasant scent"...

s (ethanol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...

), and nail polish, (part of how it stays on nails) and in chemical synthesis. The use of inorganic
Inorganic chemistry
Inorganic chemistry is the branch of chemistry concerned with the properties and behavior of inorganic compounds. This field covers all chemical compounds except the myriad organic compounds , which are the subjects of organic chemistry...

 solvents (other than water) is typically limited to research chemistry
Chemistry
Chemistry is the science of matter, especially its chemical reactions, but also its composition, structure and properties. Chemistry is concerned with atoms and their interactions with other atoms, and particularly with the properties of chemical bonds....

 and some technological processes.

In 2005, the worldwide market for solvents had a total volume of around 17.9 million tons, which led to a turnover of about €8,000,000,000.

Solutions and solvation


When one substance is dissolved
Dissolution (chemistry)
Dissolution is the process by which a solid, liquid or gas forms a solution in a solvent. In solids this can be explained as the breakdown of the crystal lattice into individual ions, atoms or molecules and their transport into the solvent. For liquids and gases, the molecules must be compatible...

 into another, a solution
Solution
In chemistry, a solution is a homogeneous mixture composed of only one phase. In such a mixture, a solute is dissolved in another substance, known as a solvent. The solvent does the dissolving.- Types of solutions :...

 is formed. This is opposed to the situation when the compounds are insoluble
Solubility
Solubility is the property of a solid, liquid, or gaseous chemical substance called solute to dissolve in a solid, liquid, or gaseous solvent to form a homogeneous solution of the solute in the solvent. The solubility of a substance fundamentally depends on the used solvent as well as on...

 and one of them precipitate like sand in water. In solution, all of the ingredients are uniformly distributed at a molecular level and no residue remains. The mixing is referred to as miscibility
Miscibility
Miscibility is the property of liquids to mix in all proportions, forming a homogeneous solution. In principle, the term applies also to other phases , but the main focus is usually on the solubility of one liquid in another...

, whereas the ability to dissolve one compound into another is known as solubility
Solubility
Solubility is the property of a solid, liquid, or gaseous chemical substance called solute to dissolve in a solid, liquid, or gaseous solvent to form a homogeneous solution of the solute in the solvent. The solubility of a substance fundamentally depends on the used solvent as well as on...

. However, in addition to mixing, both substances in the solution interact with each other. When something is dissolved, molecules of the solvent arrange themselves around molecules of the solute. Heat
Heat
In physics and thermodynamics, heat is energy transferred from one body, region, or thermodynamic system to another due to thermal contact or thermal radiation when the systems are at different temperatures. It is often described as one of the fundamental processes of energy transfer between...

 is involved and entropy
Entropy
Entropy is a thermodynamic property that can be used to determine the energy available for useful work in a thermodynamic process, such as in energy conversion devices, engines, or machines. Such devices can only be driven by convertible energy, and have a theoretical maximum efficiency when...

 is increased making the solution more thermodynamically
Thermodynamics
Thermodynamics is a physical science that studies the effects on material bodies, and on radiation in regions of space, of transfer of heat and of work done on or by the bodies or radiation...

 stable than the solute alone. This arrangement is mediated by the respective chemical properties of the solvent and solute, such as hydrogen bonding, dipole moment
Bond dipole moment
The bond dipole moment uses the idea of electric dipole moment to measure the polarity of a chemical bond within a molecule. The bond dipole μ is given by:\mu = \delta \, d....

 and polarizability
Polarizability
Polarizability is the measure of the change in a molecule's electron distribution in response to an applied electric field, which can also be induced by electric interactions with solvents or ionic reagents. It is a property of matter...

.

Solvent classifications


Solvents can be broadly classified into two categories: polar and non-polar. Generally, the dielectric constant
Dielectric constant
The relative permittivity of a material under given conditions reflects the extent to which it concentrates electrostatic lines of flux. In technical terms, it is the ratio of the amount of electrical energy stored in a material by an applied voltage, relative to that stored in a vacuum...

 of the solvent provides a rough measure of a solvent's polarity. The strong polarity of water is indicated, at 20 °C, by a dielectric constant of 80.10;. Solvents with a dielectric constant of less than 15 are generally considered to be nonpolar. Technically, the dielectric constant measures the solvent's ability to reduce the field strength of the electric field surrounding a charged particle
Ion
An ion is an atom or molecule in which the total number of electrons is not equal to the total number of protons, giving it a net positive or negative electrical charge. The name was given by physicist Michael Faraday for the substances that allow a current to pass between electrodes in a...

 immersed in it. This reduction is then compared to the field strength
Field strength
In physics, the field strength of a field is the magnitude of its vector value.In theoretical physics, field strength is another name for the curvature form...

 of the charged particle in a vacuum. In layman's terms, dielectric constant of a solvent can be thought of as its ability to reduce the solute's internal charge
Chemical polarity
In chemistry, polarity refers to a separation of electric charge leading to a molecule or its chemical groups having an electric dipole or multipole moment. Polar molecules interact through dipole–dipole intermolecular forces and hydrogen bonds. Molecular polarity is dependent on the difference in...

.

Other polarity scales


Dielectric constants are not the only measure of polarity. Because solvents are used by chemists to carry out chemical reactions or observe chemical and biological phenomena, more specific measures of polarity are required.

The Grunwald Winstein
Saul Winstein
Saul Winstein was the Canadian chemist who discovered the Winstein reaction, in which he argued a non-classical cation was needed to explain the stability of the norbornyl cation. This fueled a debate with Herbert C. Brown over the existence of delocalized cations such as this. Richard F...

 mY scale
measures polarity in terms of solvent influence on buildup of positive charge of a solute during a chemical reaction.

Kosower's Z scale measures polarity in terms of the influence of the solvent on uv
Ultraviolet
Ultraviolet light is electromagnetic radiation with a wavelength shorter than that of visible light, but longer than X-rays, in the range 10 nm to 400 nm, and energies from 3 eV to 124 eV...

 absorption maxima of a salt, usually pyridinium
Pyridinium
Pyridinium refers to the cationic form of pyridine. This can either be due to protonation of the ring nitrogen or because of addition of a substituent to the ring nitrogen, typically via alkylation. The lone pair of electrons on the nitrogen atom of pyridine is not delocalized, and thus pyridine...

 iodide
Iodide
An iodide ion is the ion I−. Compounds with iodine in formal oxidation state −1 are called iodides. This page is for the iodide ion and its salts. For information on organoiodides, see organohalides. In everyday life, iodide is most commonly encountered as a component of iodized salt,...

 or the pyridinium zwitterion
Zwitterion
In chemistry, a zwitterion is a neutral molecule with a positive and a negative electrical charge at different locations within that molecule. Zwitterions are sometimes also called inner salts.-Examples:...

.

Donor number and donor acceptor scale measures polarity in terms of how a solvent interacts with specific substances, like a strong Lewis acid
Lewis acid
]The term Lewis acid refers to a definition of acid published by Gilbert N. Lewis in 1923, specifically: An acid substance is one which can employ a lone pair from another molecule in completing the stable group of one of its own atoms. Thus, H+ is a Lewis acid, since it can accept a lone pair,...

 or a strong Lewis base.

The polarity, dipole moment, polarizability and hydrogen bonding of a solvent determines what type of compounds
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...

 it is able to dissolve and with what other solvents or liquid compounds it is miscible. As a rule of thumb, polar solvents dissolve polar compounds best and non-polar solvents dissolve non-polar compounds best: "like dissolves like". Strongly polar compounds like sugars (e.g., sucrose) or ionic compounds, like inorganic
Inorganic chemistry
Inorganic chemistry is the branch of chemistry concerned with the properties and behavior of inorganic compounds. This field covers all chemical compounds except the myriad organic compounds , which are the subjects of organic chemistry...

 salt
Salt
In chemistry, salts are ionic compounds that result from the neutralization reaction of an acid and a base. They are composed of cations and anions so that the product is electrically neutral...

s (e.g., table salt) dissolve only in very polar solvents like water, while strongly non-polar compounds like oil
Oil
An oil is any substance that is liquid at ambient temperatures and does not mix with water but may mix with other oils and organic solvents. This general definition includes vegetable oils, volatile essential oils, petrochemical oils, and synthetic oils....

s or wax
Wax
thumb|right|[[Cetyl palmitate]], a typical wax ester.Wax refers to a class of chemical compounds that are plastic near ambient temperatures. Characteristically, they melt above 45 °C to give a low viscosity liquid. Waxes are insoluble in water but soluble in organic, nonpolar solvents...

es dissolve only in very non-polar organic solvents like hexane
Hexane
Hexane is a hydrocarbon with the chemical formula C6H14; that is, an alkane with six carbon atoms.The term may refer to any of four other structural isomers with that formula, or to a mixture of them. In the IUPAC nomenclature, however, hexane is the unbranched isomer ; the other four structures...

. Similarly, water and hexane
Hexane
Hexane is a hydrocarbon with the chemical formula C6H14; that is, an alkane with six carbon atoms.The term may refer to any of four other structural isomers with that formula, or to a mixture of them. In the IUPAC nomenclature, however, hexane is the unbranched isomer ; the other four structures...

 (or vinegar
Vinegar
Vinegar is a liquid substance consisting mainly of acetic acid and water, the acetic acid being produced through the fermentation of ethanol by acetic acid bacteria. Commercial vinegar is produced either by fast or slow fermentation processes. Slow methods generally are used with traditional...

 and vegetable oil) are not miscible with each other and will quickly separate into two layers even after being shaken well.

Polar protic and polar aprotic


Solvents with a relative static permittivity greater than 15 can be further divided into protic
Protic
Protić is a Serbian surname. It may refer to:* Milorad B. Protić, an astronomer* Miodrag B. Protić, a painter* Stojan Protić, Yugoslav political figure...

 and aprotic. Protic solvents solvate anions (negatively charged solutes) strongly via hydrogen bonding. Water is a protic solvent. Aprotic solvents such as acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...

 or dichloromethane
Dichloromethane
Dichloromethane is an organic compound with the formula CH2Cl2. This colorless, volatile liquid with a moderately sweet aroma is widely used as a solvent. Although it is not miscible with water, it is miscible with many organic solvents...

 tend to have large dipole moments (separation of partial positive and partial negative charges within the same molecule) and solvate positively charged species via their negative dipole. In chemical reaction
Chemical reaction
A chemical reaction is a process that leads to the transformation of one set of chemical substances to another. Chemical reactions can be either spontaneous, requiring no input of energy, or non-spontaneous, typically following the input of some type of energy, such as heat, light or electricity...

s the use of polar protic solvents favors the SN1
SN1 reaction
The SN1 reaction is a substitution reaction in organic chemistry. "SN" stands for nucleophilic substitution and the "1" represents the fact that the rate-determining step is unimolecular...

 reaction mechanism
Reaction mechanism
In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical change occurs.Although only the net chemical change is directly observable for most chemical reactions, experiments can often be designed that suggest the possible sequence of steps in...

, while polar aprotic solvents favor the SN2
SN2 reaction
The SN2 reaction is a type of nucleophilic substitution, where a lone pair from a nucleophile attacks an electron deficient electrophilic center and bonds to it, expelling another group called a leaving group. Thus the incoming group replaces the leaving group in one step...

 reaction mechanism.

Properties table of common solvents


The solvents are grouped into non-polar, polar aprotic, and polar protic solvents and ordered by increasing polarity. The polarity is given as the dielectric constant
Dielectric constant
The relative permittivity of a material under given conditions reflects the extent to which it concentrates electrostatic lines of flux. In technical terms, it is the ratio of the amount of electrical energy stored in a material by an applied voltage, relative to that stored in a vacuum...

. The properties of solvents that exceed those of water are bolded.

Solvent Chemical formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....

Boiling point
Boiling point
The boiling point of an element or a substance is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid....

Dielectric constant
Dielectric constant
The relative permittivity of a material under given conditions reflects the extent to which it concentrates electrostatic lines of flux. In technical terms, it is the ratio of the amount of electrical energy stored in a material by an applied voltage, relative to that stored in a vacuum...

Density
Density
The mass density or density of a material is defined as its mass per unit volume. The symbol most often used for density is ρ . In some cases , density is also defined as its weight per unit volume; although, this quantity is more properly called specific weight...

Dipole moment
Non-polar solvents
Pentane
Pentane
Pentane is an organic compound with the formula C5H12 — that is, an alkane with five carbon atoms. The term may refer to any of three structural isomers, or to a mixture of them: in the IUPAC nomenclature, however, pentane means exclusively the n-pentane isomer; the other two being called...

CH3-CH2-CH2-CH2-CH3 36 °C 1.84 0.626 g/ml 0.00 D
Cyclopentane
Cyclopentane
Cyclopentane is a highly flammable alicyclic hydrocarbon with chemical formula 510 and CAS number 287-92-3, consisting of a ring of five carbon atoms each bonded with two hydrogen atoms above and below the plane. It occurs as a colorless liquid with a petrol-like odor. Its melting point is −94 °C...

C5H10 40 °C 1.97 0.751 g/ml 0.00 D
Hexane
Hexane
Hexane is a hydrocarbon with the chemical formula C6H14; that is, an alkane with six carbon atoms.The term may refer to any of four other structural isomers with that formula, or to a mixture of them. In the IUPAC nomenclature, however, hexane is the unbranched isomer ; the other four structures...

CH3-CH2-CH2-CH2-CH2-CH3 69 °C 1.88 0.655 g/ml 0.00 D
Cyclohexane
Cyclohexane
Cyclohexane is a cycloalkane with the molecular formula C6H12. Cyclohexane is used as a nonpolar solvent for the chemical industry, and also as a raw material for the industrial production of adipic acid and caprolactam, both of which being intermediates used in the production of nylon...

C6H12 81 °C 2.02 0.779 g/ml 0.00 D
Benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....

C6H6 80 °C 2.3 0.879 g/ml 0.00 D
Toluene
Toluene
Toluene, formerly known as toluol, is a clear, water-insoluble liquid with the typical smell of paint thinners. It is a mono-substituted benzene derivative, i.e., one in which a single hydrogen atom from the benzene molecule has been replaced by a univalent group, in this case CH3.It is an aromatic...

C6H5-CH3 111 °C 2.38 0.867 g/ml 0.36 D
1,4-Dioxane
1,4-Dioxane
1,4-Dioxane, often called dioxane because the other isomers of dioxane are rare, is a heterocyclic organic compound. It is a colorless liquid with a faint sweet odor similar to that of diethyl ether. It is classified as an ether. This colorless liquid is mainly used as a stabilizer for the solvent...

/-CH2-CH2-O-CH2-CH2-O-\ 101 °C 2.3 1.033 g/ml 0.45 D
Chloroform
Chloroform
Chloroform is an organic compound with formula CHCl3. It is one of the four chloromethanes. The colorless, sweet-smelling, dense liquid is a trihalomethane, and is considered somewhat hazardous...

CHCl3 61 °C 4.81 1.498 g/ml 1.04 D
Diethyl ether
Diethyl ether
Diethyl ether, also known as ethyl ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula . It is a colorless, highly volatile flammable liquid with a characteristic odor...

CH3CH2-O-CH2-CH3 35 °C 4.3 0.713 g/ml 1.15 D
Polar
Chemical polarity
In chemistry, polarity refers to a separation of electric charge leading to a molecule or its chemical groups having an electric dipole or multipole moment. Polar molecules interact through dipole–dipole intermolecular forces and hydrogen bonds. Molecular polarity is dependent on the difference in...

 aprotic solvents
Dichloromethane
Dichloromethane
Dichloromethane is an organic compound with the formula CH2Cl2. This colorless, volatile liquid with a moderately sweet aroma is widely used as a solvent. Although it is not miscible with water, it is miscible with many organic solvents...

 (DCM)
CH2Cl2 40 °C 9.1 1.3266 g/ml 1.60 D
Tetrahydrofuran
Tetrahydrofuran
Tetrahydrofuran is a colorless, water-miscible organic liquid with low viscosity at standard temperature and pressure. This heterocyclic compound has the chemical formula 4O. As one of the most polar ethers with a wide liquid range, it is a useful solvent. Its main use, however, is as a precursor...

 (THF)
/-CH2-CH2-O-CH2-CH2-\ 66 °C 7.5 0.886 g/ml 1.75 D
Ethyl acetate
Ethyl acetate
Ethyl acetate is the organic compound with the formula CH3COOCH2CH3. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and cigarettes...

CH3-C(=O)-O-CH2-CH3 77 °C 6.02 0.894 g/ml 1.78 D
Acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...

CH3-C(=O)-CH3 56 °C 21 0.786 g/ml 2.88 D
Dimethylformamide
Dimethylformamide
Dimethylformamide is an organic compound with the formula 2NCH. Commonly abbreviated as DMF , this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions...

 (DMF)
H-C(=O)N(CH3)2 153 °C 38 0.944 g/ml 3.82 D
Acetonitrile
Acetonitrile
Acetonitrile is the chemical compound with formula . This colourless liquid is the simplest organic nitrile. It is produced mainly as a byproduct of acrylonitrile manufacture...

 (MeCN)
CH3-C≡N 82 °C 37.5 0.786 g/ml 3.92 D
Dimethyl sulfoxide
Dimethyl sulfoxide
Dimethyl sulfoxide is an organosulfur compound with the formula 2SO. This colorless liquid is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water...

 (DMSO)
CH3-S(=O)-CH3 189 °C 46.7 1.092 g/ml 3.96 D
Polar protic
Protic
Protić is a Serbian surname. It may refer to:* Milorad B. Protić, an astronomer* Miodrag B. Protić, a painter* Stojan Protić, Yugoslav political figure...

 solvents
Formic acid
Formic acid
Formic acid is the simplest carboxylic acid. Its chemical formula is HCOOH or HCO2H. It is an important intermediate in chemical synthesis and occurs naturally, most notably in the venom of bee and ant stings. In fact, its name comes from the Latin word for ant, formica, referring to its early...

H-C(=O)OH 101 °C 58 1.21 g/ml 1.41 D
n-Butanol
N-Butanol
n-Butanol or n-butyl alcohol or normal butanol is a primary alcohol with a 4-carbon structure and the molecular formula C4H9OH. Its isomers include isobutanol, 2-butanol, and tert-butanol...

CH3-CH2-CH2-CH2-OH 118 °C 18 0.810 g/ml 1.63 D
Isopropanol (IPA) CH3-CH(-OH)-CH3 82 °C 18 0.785 g/ml 1.66 D
n-Propanol CH3-CH2-CH2-OH 97 °C 20 0.803 g/ml 1.68 D
Ethanol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...

CH3-CH2-OH 79 °C 24.55 0.789 g/ml 1.69 D
Methanol
Methanol
Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...

CH3-OH 65 °C 33 0.791 g/ml 1.70 D
Acetic acid
Acetic acid
Acetic acid is an organic compound with the chemical formula CH3CO2H . It is a colourless liquid that when undiluted is also called glacial acetic acid. Acetic acid is the main component of vinegar , and has a distinctive sour taste and pungent smell...

CH3-C(=O)OH 118 °C 6.2 1.049 g/ml 1.74 D
Water H-O-H 100 °C 80 1.000 g/ml 1.85 D


There's another powerful way to look at these same solvents. By knowing their Hansen solubility parameter values (HSPiP), which are based on δD=dispersion bonds, δP=polar bonds and δH=hydrogen bonds, you know important things about their inter-molecular interactions with other solvents and also with polymers, pigments, nanoparticles etc. so you can do two things. First, you can create rational formulations knowing, for example, that there is a good HSP match between a solvent and a polymer. Second, you can make rational substitutions for "good" solvents (they dissolve things well) that are "bad" (for the environment, for health, for cost etc.). The following table shows that the intuitions from "non-polar", "polar aprotic" and "polar protic" are put numerically - the "polar" molecules have higher levels of δP and the protic solvents have higher levels of δH. Because numerical values are used, comparisons can be made rationally by comparing numbers. So acetonitrile is much more polar than acetone but slightly less hydrogen bonding.
{| border="1" cellpadding="5" cellspacing="0" align="center" style="text-align:center"
! Solvent
! Chemical formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....


! δD Dispersion
! δP Polar
! δH Hydrogen bonding
|- bgcolor="#DDDDDD"
| colspan="5"|Non-polar solvents
|- bgcolor="#DDDDDD"
| Hexane
Hexane
Hexane is a hydrocarbon with the chemical formula C6H14; that is, an alkane with six carbon atoms.The term may refer to any of four other structural isomers with that formula, or to a mixture of them. In the IUPAC nomenclature, however, hexane is the unbranched isomer ; the other four structures...


| CH3-CH2-CH2-CH2-CH2-CH3
| 14.9
| 0.0
| 0.0
|- bgcolor="#DDDDDD"
| Benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....


| C6H6
| 18.4
| 0.0
| 2.0
|- bgcolor="#DDDDDD"
| Toluene
Toluene
Toluene, formerly known as toluol, is a clear, water-insoluble liquid with the typical smell of paint thinners. It is a mono-substituted benzene derivative, i.e., one in which a single hydrogen atom from the benzene molecule has been replaced by a univalent group, in this case CH3.It is an aromatic...


| C6H5-CH3
| 18.0
| 1.4
| 2.0
|- bgcolor="#DDDDDD"
| Diethyl ether
Diethyl ether
Diethyl ether, also known as ethyl ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula . It is a colorless, highly volatile flammable liquid with a characteristic odor...


| CH3CH2-O-CH2-CH3
| 14.5
| 2.9
| 4.6
|- bgcolor="#DDDDDD"
| Chloroform
Chloroform
Chloroform is an organic compound with formula CHCl3. It is one of the four chloromethanes. The colorless, sweet-smelling, dense liquid is a trihalomethane, and is considered somewhat hazardous...


| CHCl3
| 17.8
| 3.1
| 5.7
|- bgcolor="#DDDDDD"
| 1,4-Dioxane
1,4-Dioxane
1,4-Dioxane, often called dioxane because the other isomers of dioxane are rare, is a heterocyclic organic compound. It is a colorless liquid with a faint sweet odor similar to that of diethyl ether. It is classified as an ether. This colorless liquid is mainly used as a stabilizer for the solvent...


| /-CH2-CH2-O-CH2-CH2-O-\
| 17.5
| 1.8
| 9.0
|- bgcolor="#FFCCFF"
| colspan="5"|Polar aprotic solvents
|- bgcolor="#FFCCFF"
| Ethyl acetate
Ethyl acetate
Ethyl acetate is the organic compound with the formula CH3COOCH2CH3. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and cigarettes...


| CH3-C(=O)-O-CH2-CH3
| 15.8
| 5.3
| 7.2
|- bgcolor="#FFCCFF"
| Tetrahydrofuran
Tetrahydrofuran
Tetrahydrofuran is a colorless, water-miscible organic liquid with low viscosity at standard temperature and pressure. This heterocyclic compound has the chemical formula 4O. As one of the most polar ethers with a wide liquid range, it is a useful solvent. Its main use, however, is as a precursor...

 (THF)
| /-CH2-CH2-O-CH2-CH2-\
| 16.8
| 5.7
| 8.0
|- bgcolor="#FFCCFF"
| Dichloromethane
Dichloromethane
Dichloromethane is an organic compound with the formula CH2Cl2. This colorless, volatile liquid with a moderately sweet aroma is widely used as a solvent. Although it is not miscible with water, it is miscible with many organic solvents...


| CH2Cl2
| 17.0
| 7.3
| 7.1
|- bgcolor="#FFCCFF"
| Acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...


| CH3-C(=O)-CH3
| 15.5
| 10.4
| 7.0
|- bgcolor="#FFCCFF"
| Acetonitrile
Acetonitrile
Acetonitrile is the chemical compound with formula . This colourless liquid is the simplest organic nitrile. It is produced mainly as a byproduct of acrylonitrile manufacture...

 (MeCN)
| CH3-C≡N
| 15.3
| 18.0
| 6.1
|- bgcolor="#FFCCFF"
| Dimethylformamide
Dimethylformamide
Dimethylformamide is an organic compound with the formula 2NCH. Commonly abbreviated as DMF , this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions...

 (DMF)
| H-C(=O)N(CH3)2
| 17.4
| 13.7
| 11.3
|- bgcolor="#FFCCFF"
| Dimethyl sulfoxide
Dimethyl sulfoxide
Dimethyl sulfoxide is an organosulfur compound with the formula 2SO. This colorless liquid is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water...

 (DMSO)
| CH3-S(=O)-CH3
| 18.4
| 16.4
| 10.2
|- bgcolor="#FFCCCC"
| colspan="5"|Polar protic solvents
|- bgcolor="#FFCCCC"
| Acetic acid
Acetic acid
Acetic acid is an organic compound with the chemical formula CH3CO2H . It is a colourless liquid that when undiluted is also called glacial acetic acid. Acetic acid is the main component of vinegar , and has a distinctive sour taste and pungent smell...


| CH3-C(=O)OH
| 14.5
| 8.0
| 13.5
|- bgcolor="#FFCCCC"
| n-Butanol
N-Butanol
n-Butanol or n-butyl alcohol or normal butanol is a primary alcohol with a 4-carbon structure and the molecular formula C4H9OH. Its isomers include isobutanol, 2-butanol, and tert-butanol...


| CH3-CH2-CH2-CH2-OH
| 16.0
| 5.7
| 15.8
|- bgcolor="#FFCCCC"
| Isopropanol
| CH3-CH(-OH)-CH3
| 15.8
| 6.1
| 16.4
|- bgcolor="#FFCCCC"
| n-Propanol
| CH3-CH2-CH2-OH
| 16.0
| 6.8
| 17.4
|- bgcolor="#FFCCCC"
| Ethanol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...


| CH3-CH2-OH
| 15.8
| 8.8
| 19.4
|- bgcolor="#FFCCCC"
| Methanol
Methanol
Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...


| CH3-OH
| 14.7
| 12.3
| 22.3
|- bgcolor="#FFCCCC"
| Formic acid
Formic acid
Formic acid is the simplest carboxylic acid. Its chemical formula is HCOOH or HCO2H. It is an important intermediate in chemical synthesis and occurs naturally, most notably in the venom of bee and ant stings. In fact, its name comes from the Latin word for ant, formica, referring to its early...


| H-C(=O)OH
| 14.6
| 10.0
| 14.0
|- bgcolor="#FFCCCC"
| Water
| H-O-H
| 15.5
| 16.0
| 42.3

Consider a simple example of rational substitution. Suppose for environmental reasons we needed to replace the chlorinated solvent, chloroform, with a solvent (blend) of equal solvency using a mixture of two non-chlorinated solvents from this table. Via trial-and-error, a spreadsheet or some software such as HSPiP we find that a 50:50 mix of toluene and 1,4 dioxane is a close match. The δD of the mixture is the average of 18.0 and 17.5 = 17.8. The δP of the mixture is the average of 1.4 and 1.8 = 1.6 and the δH of the mixture is the average of 2.0 and 9.0 = 5.5. So the mixture is 17.8, 1.6, 5.5 compared to Chloroform at 17.8, 3.1, 5.7. Because Toluene itself has many health issues, other mixtures of solvents can be found using a full Hansen solubility parameter dataset.

Boiling point



An important property of solvents is boiling point. This also determines the speed of evaporation. Small amounts of low-boiling solvents like diethyl ether
Diethyl ether
Diethyl ether, also known as ethyl ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula . It is a colorless, highly volatile flammable liquid with a characteristic odor...

, dichloromethane
Dichloromethane
Dichloromethane is an organic compound with the formula CH2Cl2. This colorless, volatile liquid with a moderately sweet aroma is widely used as a solvent. Although it is not miscible with water, it is miscible with many organic solvents...

, or acetone will evaporate in seconds at room temperature, while high-boiling solvents like water or dimethyl sulfoxide
Dimethyl sulfoxide
Dimethyl sulfoxide is an organosulfur compound with the formula 2SO. This colorless liquid is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water...

 need higher temperatures, an air flow, or the application of vacuum
Vacuum
In everyday usage, vacuum is a volume of space that is essentially empty of matter, such that its gaseous pressure is much less than atmospheric pressure. The word comes from the Latin term for "empty". A perfect vacuum would be one with no particles in it at all, which is impossible to achieve in...

 for fast evaporation.
  • Low boilers: boiling temperature below 100 °C (boiling point of water)
  • Medium boilers: between 100 °C and 150 °C
  • High boilers: above 150 °C

Density


Most organic solvents have a lower density
Density
The mass density or density of a material is defined as its mass per unit volume. The symbol most often used for density is ρ . In some cases , density is also defined as its weight per unit volume; although, this quantity is more properly called specific weight...

 than water, which means they are lighter and will form a separate layer on top of water. An important exception: most of the halogen
Halogen
The halogens or halogen elements are a series of nonmetal elements from Group 17 IUPAC Style of the periodic table, comprising fluorine , chlorine , bromine , iodine , and astatine...

ated solvents like dichloromethane
Dichloromethane
Dichloromethane is an organic compound with the formula CH2Cl2. This colorless, volatile liquid with a moderately sweet aroma is widely used as a solvent. Although it is not miscible with water, it is miscible with many organic solvents...

 or chloroform
Chloroform
Chloroform is an organic compound with formula CHCl3. It is one of the four chloromethanes. The colorless, sweet-smelling, dense liquid is a trihalomethane, and is considered somewhat hazardous...

 will sink to the bottom of a container, leaving water as the top layer. This is important to remember when partitioning
Partition coefficient
In chemistry and the pharmaceutical sciences, a partition- or distribution coefficient is the ratio of concentrations of a compound in the two phases of a mixture of two immiscible solvents at equilibrium. The terms "gas/liquid partition coefficient" and "air/water partition coefficient" are...

 compounds between solvents and water in a separatory funnel
Separatory funnel
A separatory funnel, also known as separation funnel, separating funnel, or colloquially sep funnel, is a piece of laboratory glassware used in liquid-liquid extractions to separate the components of a mixture between two immiscible solvent phases of different densities Typically, one of the...

 during chemical syntheses.

Often, specific gravity is cited in place of density. Specific gravity is defined as the density of the solvent divided by the density of water at the same temperature. As such, specific gravity is a unitless value. It readily communicates whether a water-insoluble solvent will float (SG < 1.0) or sink (SG > 1.0) when mixed with water.

{| class="wikitable" border="1" style="margin:1em auto;text-align:center;"
|-
! Solvent
! Specific gravity
|-
| Pentane
| 0.626
|-
| Petroleum ether
| 0.656
|-
| Hexane
| 0.659
|-
| Heptane
| 0.684
|-
| Diethyl amine
| 0.707
|-
| Diethyl ether
| 0.713
|-
| Triethyl amine
| 0.728
|-
| Tert-butyl methyl ether
| 0.741
|-
| Cyclohexane
| 0.779
|-
| Tert-butyl alcohol
| 0.781
|-
| Isopropanol
| 0.785
|-
| Acetonitrile
| 0.786
|-
| Ethanol
| 0.789
|-
| Acetone
| 0.790
|-
| Methanol
| 0.791
|-
| Methyl isobutyl ketone
| 0.798
|-
| Isobutyl alcohol
| 0.802
|-
| 1-Propanol
| 0.803
|-
| Methyl ethyl ketone
| 0.805
|-
| 2-Butanol
| 0.808
|-
| Isoamyl alcohol
| 0.809
|-
| 1-Butanol
| 0.810
|-
| Diethyl ketone
| 0.814
|-
| 1-Octanol
| 0.826
|-
| p-Xylene
| 0.861
|-
| m-Xylene
| 0.864
|-
| Toluene
| 0.867
|-
| Dimethoxyethane
| 0.868
|-
| Benzene
| 0.879
|-
| Butyl acetate
| 0.882
|-
| 1-Chlorobutane
| 0.886
|-
| Tetrahydrofuran
| 0.889
|-
| Ethyl acetate
| 0.895
|-
| o-Xylene
| 0.897
|-
| Hexamethylphosphorus triamide
| 0.898
|-
| 2-Ethoxyethyl ether
| 0.909
|-
| N,N-Dimethylacetamide
| 0.937
|-
| Diethylene glycol dimethyl ether
| 0.943­
|-
| N,N-Dimethylformamide
| 0.944
|-
| 2-Methoxyethanol
| 0.965
|-
| Pyridine
| 0.982
|-
| Propanoic acid
| 0.993
|-
| Water
| 1.000
|-
| 2-Methoxyethyl acetate
| 1.009
|-
| Benzonitrile
| 1.01
|-
| 1-Methyl-2-pyrrolidinone
| 1.028
|-.
| Hexamethylphosphoramide
| 1.03
|-
| 1,4-Dioxane
| 1.033
|-
| Acetic acid
| 1.049
|-
| Acetic anhydride
| 1.08
|-
| Dimethyl sulfoxide
| 1.092
|-
| Chlorobenzene
| 1.1066
|-
| Deuterium oxide
| 1.107
|-
| Ethylene glycol
| 1.115
|-
| Diethylene glycol
| 1.118
|-
| Propylene carbonate
| 1.21
|-
| Formic acid
| 1.22
|-
| 1,2-Dichloroethane
| 1.245
|-
| Glycerin
| 1.261
|-
| Carbon disulfide
| 1.263
|-
| 1,2-Dichlorobenzene
| 1.306
|-
| Methylene chloride
| 1.326
|-
| Nitromethane
| 1.382
|-
| 2,2,2-Trifluoroethanol
| 1.393
|-
| Chloroform
| 1.498
|-
| 1,1,2-Trichlorotrifluoroethane
| 1.575
|-
| Carbon tetrachloride
| 1.594
|-
| Tetrachloroethylene
| 1.623
|}­­­­

Fire


Most organic solvents are flammable or highly flammable, depending on their volatility. Exceptions are some chlorinated solvents like dichloromethane
Dichloromethane
Dichloromethane is an organic compound with the formula CH2Cl2. This colorless, volatile liquid with a moderately sweet aroma is widely used as a solvent. Although it is not miscible with water, it is miscible with many organic solvents...

 and chloroform
Chloroform
Chloroform is an organic compound with formula CHCl3. It is one of the four chloromethanes. The colorless, sweet-smelling, dense liquid is a trihalomethane, and is considered somewhat hazardous...

. Mixtures of solvent vapors and air can explode
Explosion
An explosion is a rapid increase in volume and release of energy in an extreme manner, usually with the generation of high temperatures and the release of gases. An explosion creates a shock wave. If the shock wave is a supersonic detonation, then the source of the blast is called a "high explosive"...

. Solvent vapors are heavier than air; they will sink to the bottom and can travel large distances nearly undiluted. Solvent vapors can also be found in supposedly empty drums and cans, posing a flash fire
Flash fire
A flash fire is a sudden, intense fire caused by ignition of a mixture of air and a dispersed flammable substance such as a solid , flammable or combustible liquid , or a flammable gas...

 hazard; hence empty containers of volatile solvents should be stored open and upside down.

Both diethyl ether
Diethyl ether
Diethyl ether, also known as ethyl ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula . It is a colorless, highly volatile flammable liquid with a characteristic odor...

 and carbon disulfide
Carbon disulfide
Carbon disulfide is a colorless volatile liquid with the formula CS2. The compound is used frequently as a building block in organic chemistry as well as an industrial and chemical non-polar solvent...

 have exceptionally low autoignition temperature
Autoignition temperature
The autoignition temperature or kindling point of a substance is the lowest temperature at which it will spontaneously ignite in a normal atmosphere without an external source of ignition, such as a flame or spark. This temperature is required to supply the activation energy needed for combustion...

s which increase greatly the fire risk associated with these solvents. The autoignition temperature of carbon disulfide is below 100°C (212°F), so objects such as steam
Steam
Steam is the technical term for water vapor, the gaseous phase of water, which is formed when water boils. In common language it is often used to refer to the visible mist of water droplets formed as this water vapor condenses in the presence of cooler air...

 pipes, light bulbs, hotplates and recently extinguished bunsen burner
Bunsen burner
A Bunsen burner, named after Robert Bunsen, is a common piece of laboratory equipment that produces a single open gas flame, which is used for heating, sterilization, and combustion.- Operation:...

s are able to ignite its vapours.

Explosive peroxide formation


Ether
Ether
Ethers are a class of organic compounds that contain an ether group — an oxygen atom connected to two alkyl or aryl groups — of general formula R–O–R'. A typical example is the solvent and anesthetic diethyl ether, commonly referred to simply as "ether"...

s like diethyl ether
Diethyl ether
Diethyl ether, also known as ethyl ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula . It is a colorless, highly volatile flammable liquid with a characteristic odor...

 and tetrahydrofuran
Tetrahydrofuran
Tetrahydrofuran is a colorless, water-miscible organic liquid with low viscosity at standard temperature and pressure. This heterocyclic compound has the chemical formula 4O. As one of the most polar ethers with a wide liquid range, it is a useful solvent. Its main use, however, is as a precursor...

 (THF) can form highly explosive organic peroxide
Organic peroxide
Organic peroxides are organic compounds containing the peroxide functional group . If the R' is hydrogen, the compound is called an organic hydroperoxide. Peresters have general structure RCOOR. The O-O bond easily breaks and forms free radicals of the form RO·...

s upon exposure to oxygen and light, THF is normally more able to form such peroxide
Peroxide
A peroxide is a compound containing an oxygen–oxygen single bond or the peroxide anion .The O−O group is called the peroxide group or peroxo group. In contrast to oxide ions, the oxygen atoms in the peroxide ion have an oxidation state of −1.The simplest stable peroxide is hydrogen peroxide...

s than diethyl ether. One of the most susceptible solvents is diisopropyl ether
Diisopropyl ether
Diisopropyl ether is secondary ether that is used as a solvent. It is a colorless liquid that is slightly soluble in water, but miscible with most organic solvents...

.

The heteroatom (oxygen
Oxygen
Oxygen is the element with atomic number 8 and represented by the symbol O. Its name derives from the Greek roots ὀξύς and -γενής , because at the time of naming, it was mistakenly thought that all acids required oxygen in their composition...

) stabilizes the formation of a free radical which is formed by the abstraction of a hydrogen
Hydrogen
Hydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...

 atom by another free radical. The carbon centred free radical thus formed is able to react with an oxygen molecule to form a peroxide compound. A range of tests can be used to detect the presence of a peroxide in an ether; one is to use a combination of iron sulfate
Iron sulfate
Iron sulfate may refer to:*Ferrous sulphate, Iron sulfate, FeSO4*Ferric sulphate, Iron sulfate, Fe23...

 and potassium thiocyanate
Potassium thiocyanate
Potassium thiocyanate is the chemical compound with the molecular formula KSCN. It is an important salt of the thiocyanate anion, one of the pseudohalides...

. The peroxide is able to oxidize the Fe2+ ion to an Fe3+ ion which then form a deep red coordination complex with the thiocyanate
Thiocyanate
Thiocyanate is the anion [SCN]−. It is the conjugate base of thiocyanic acid. Common derivatives include the colourless salts potassium thiocyanate and sodium thiocyanate. Organic compounds containing the functional group SCN are also called thiocyanates...

. In extreme cases the peroxides can form crystalline solids within the vessel of the ether.

Unless the desiccant
Desiccant
A desiccant is a hygroscopic substance that induces or sustains a state of dryness in its local vicinity in a moderately well-sealed container....

 used can destroy the peroxides, they will concentrate during distillation due to their higher boiling point
Boiling point
The boiling point of an element or a substance is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid....

. When sufficient peroxides have formed, they can form a crystalline and shock sensitive solid precipitate. When this solid is formed at the mouth of the bottle, turning the cap may provide sufficient energy for the peroxide to detonate. Peroxide formation is not a significant problem when solvents are used up quickly; they are more of a problem for laboratories which take years to finish a single bottle. Ethers have to be stored in the dark in closed canisters in the presence of stabilizers like butylated hydroxytoluene
Butylated hydroxytoluene
Butylated hydroxytoluene , also known as butylhydroxytoluene, is a lipophilic organic compound that is primarily used as an antioxidant food additive as well as an antioxidant additive in cosmetics, pharmaceuticals, jet fuels, rubber, petroleum products, electrical transformer oil, and embalming...

 (BHT) or over sodium hydroxide.

Peroxides may be removed by washing with acidic iron(II) sulfate, filtering through alumina, or distilling
Distillation
Distillation is a method of separating mixtures based on differences in volatilities of components in a boiling liquid mixture. Distillation is a unit operation, or a physical separation process, and not a chemical reaction....

 from sodium
Sodium
Sodium is a chemical element with the symbol Na and atomic number 11. It is a soft, silvery-white, highly reactive metal and is a member of the alkali metals; its only stable isotope is 23Na. It is an abundant element that exists in numerous minerals, most commonly as sodium chloride...

/benzophenone
Benzophenone
Benzophenone is the organic compound with the formula 2CO, generally abbreviated Ph2CO. Benzophenone is a widely used building block in organic chemistry, being the parent diarylketone.-Uses:...

. Alumina does not destroy the peroxides; it merely traps them. The advantage of using sodium/benzophenone is that moisture
Moisture
Humidity is the amount of moisture the air can hold before it rains. Moisture refers to the presence of a liquid, especially water, often in trace amounts...

 and oxygen
Oxygen
Oxygen is the element with atomic number 8 and represented by the symbol O. Its name derives from the Greek roots ὀξύς and -γενής , because at the time of naming, it was mistakenly thought that all acids required oxygen in their composition...

 are removed as well.

Health effects


General health hazards associated with solvent exposure include toxicity to the nervous system, reproductive damage, liver and kidney damage, respiratory impairment, cancer, and dermatitis
Dermatitis
-Etymology:Dermatitis derives from Greek derma "skin" + -itis "inflammation" and genetic disorder.-Terminology:There are several different types of dermatitis. The different kinds usually have in common an allergic reaction to specific allergens. The term may describe eczema, which is also called...

.

Many solvents can lead to a sudden loss of consciousness if inhaled
Inhalation
Inhalation is the movement of air from the external environment, through the air ways, and into the alveoli....

 in large amounts. Solvents like diethyl ether
Diethyl ether
Diethyl ether, also known as ethyl ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula . It is a colorless, highly volatile flammable liquid with a characteristic odor...

 and chloroform
Chloroform
Chloroform is an organic compound with formula CHCl3. It is one of the four chloromethanes. The colorless, sweet-smelling, dense liquid is a trihalomethane, and is considered somewhat hazardous...

 have been used in medicine as anesthetics, sedatives, and hypnotics for a long time. Ethanol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...

 (grain alcohol) is a widely used and abused psychoactive drug
Psychoactive drug
A psychoactive drug, psychopharmaceutical, or psychotropic is a chemical substance that crosses the blood–brain barrier and acts primarily upon the central nervous system where it affects brain function, resulting in changes in perception, mood, consciousness, cognition, and behavior...

. Diethyl ether, chloroform, and many other solvents (e.g., from gasoline
Gasoline
Gasoline , or petrol , is a toxic, translucent, petroleum-derived liquid that is primarily used as a fuel in internal combustion engines. It consists mostly of organic compounds obtained by the fractional distillation of petroleum, enhanced with a variety of additives. Some gasolines also contain...

 or glues) are used recreationally in glue sniffing, often with harmful long term health effects like neurotoxicity
Neurotoxicity
Neurotoxicity occurs when the exposure to natural or artificial toxic substances, which are called neurotoxins, alters the normal activity of the nervous system in such a way as to cause damage to nervous tissue. This can eventually disrupt or even kill neurons, key cells that transmit and process...

 or cancer
Cancer
Cancer , known medically as a malignant neoplasm, is a large group of different diseases, all involving unregulated cell growth. In cancer, cells divide and grow uncontrollably, forming malignant tumors, and invade nearby parts of the body. The cancer may also spread to more distant parts of the...

. Methanol
Methanol
Methanol, also known as methyl alcohol, wood alcohol, wood naphtha or wood spirits, is a chemical with the formula CH3OH . It is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol...

 can cause permanent blindness and death. It is also dangerous because it burns with an invisible flame.

It is interesting to note that ethanol has a synergistic effect when taken in combination with many solvents. For instance a combination of toluene
Toluene
Toluene, formerly known as toluol, is a clear, water-insoluble liquid with the typical smell of paint thinners. It is a mono-substituted benzene derivative, i.e., one in which a single hydrogen atom from the benzene molecule has been replaced by a univalent group, in this case CH3.It is an aromatic...

/benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....

 and ethanol causes greater nausea
Nausea
Nausea , is a sensation of unease and discomfort in the upper stomach with an involuntary urge to vomit. It often, but not always, precedes vomiting...

/vomiting
Vomiting
Vomiting is the forceful expulsion of the contents of one's stomach through the mouth and sometimes the nose...

 than either substance alone.

Some solvents including chloroform and benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....

 (an ingredient of gasoline
Gasoline
Gasoline , or petrol , is a toxic, translucent, petroleum-derived liquid that is primarily used as a fuel in internal combustion engines. It consists mostly of organic compounds obtained by the fractional distillation of petroleum, enhanced with a variety of additives. Some gasolines also contain...

) are carcinogen
Carcinogen
A carcinogen is any substance, radionuclide, or radiation that is an agent directly involved in causing cancer. This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes...

ic. Many others can damage internal organs like the liver
Liver
The liver is a vital organ present in vertebrates and some other animals. It has a wide range of functions, including detoxification, protein synthesis, and production of biochemicals necessary for digestion...

, the kidney
Kidney
The kidneys, organs with several functions, serve essential regulatory roles in most animals, including vertebrates and some invertebrates. They are essential in the urinary system and also serve homeostatic functions such as the regulation of electrolytes, maintenance of acid–base balance, and...

s, or the brain
Human brain
The human brain has the same general structure as the brains of other mammals, but is over three times larger than the brain of a typical mammal with an equivalent body size. Estimates for the number of neurons in the human brain range from 80 to 120 billion...

.

Chronic exposure to organic solvents in the work environment can produce a range of adverse neuropsychiatric effects and, occupational exposure to organic solvents has been associated with higher numbers of painters regularly exposed to high levels of organic solvents suffering from alcoholism
Alcoholism
Alcoholism is a broad term for problems with alcohol, and is generally used to mean compulsive and uncontrolled consumption of alcoholic beverages, usually to the detriment of the drinker's health, personal relationships, and social standing...

.

General precautions

  • Avoid being exposed to solvent vapors by working in a fume hood
    Fume hood
    A fume hood or fume cupboard is a type of local ventilation device that is designed to limit exposure to hazardous or noxious fumes, vapors or dusts. A fume hood is typically a large piece of equipment enclosing five sides of a work area, the bottom of which is most commonly located at a standing...

    , or with local exhaust ventilation (LEV), or in a well ventilated area
  • Keep the storage containers tightly closed
  • Never use open flames near flammable solvents; use electrical heating instead
  • Never flush flammable solvents down the drain; read safety data sheets for proper disposal information
  • Avoid the inhalation of solvent vapors
  • Avoid contact of the solvent with the skin — many solvents are easily absorbed through the skin. They also tend to dry the skin and may cause sores and wounds.

Environmental contamination


A major pathway to induce health effects arises from spills or leaks of solvents that reach the underlying soil. Since solvents readily migrate substantial distances, the creation of widespread soil contamination
Soil contamination
Soil contamination or soil pollution is caused by the presence of xenobiotic chemicals or other alteration in the natural soil environment....

 is not uncommon; there may be about 5000 sites worldwide that have major subsurface solvent contamination; this is particularly a health risk if aquifer
Aquifer
An aquifer is a wet underground layer of water-bearing permeable rock or unconsolidated materials from which groundwater can be usefully extracted using a water well. The study of water flow in aquifers and the characterization of aquifers is called hydrogeology...

s are affected.

See also


  • Partition coefficient
    Partition coefficient
    In chemistry and the pharmaceutical sciences, a partition- or distribution coefficient is the ratio of concentrations of a compound in the two phases of a mixture of two immiscible solvents at equilibrium. The terms "gas/liquid partition coefficient" and "air/water partition coefficient" are...

     (log P) is a measure of differential solubility of a compound in two solvents
  • Solvent systems exist outside the realm of ordinary organic solvents: Supercritical fluid
    Supercritical fluid
    A supercritical fluid is any substance at a temperature and pressure above its critical point, where distinct liquid and gas phases do not exist. It can effuse through solids like a gas, and dissolve materials like a liquid...

    s, ionic liquid
    Ionic liquid
    An ionic liquid is a salt in the liquid state. In some contexts, the term has been restricted to salts whose melting point is below some arbitrary temperature, such as . While ordinary liquids such as water and gasoline are predominantly made of electrically neutral molecules, ILs are largely made...

    s and deep eutectic solvent
    Deep eutectic solvent
    A deep eutectic solvent or DES is a type of ionic solvent with special properties composed of a mixture which forms a eutectic with a melting point much lower than either of the individual components. The first generation eutectic solvents were based on mixtures of quaternary ammonium salts with...

    s
  • Water model
    Water model
    In computational chemistry, classical water models are used for the simulation of water clusters, liquid water, and aqueous solutions with explicit solvent. These models use the approximations of molecular mechanics...

  • Water pollution
    Water pollution
    Water pollution is the contamination of water bodies . Water pollution occurs when pollutants are discharged directly or indirectly into water bodies without adequate treatment to remove harmful compounds....

  • Solvents are often refluxed with an appropriate desiccant
    Desiccant
    A desiccant is a hygroscopic substance that induces or sustains a state of dryness in its local vicinity in a moderately well-sealed container....

     prior to distillation to remove water. This may be performed prior to a chemical synthesis where water may interfere with the intended reaction.
  • Occupational health
  • Lyoluminescence
    Lyoluminescence
    Lyoluminescence refers to the emission of light while dissolving a solid into a liquid solvent. It is actually a form of chemoluminescence. The most common lyoluminescent effect is seen when solid samples which have been heavily irradiated by ionizing radiation are dissolved in water...

  • Solvation
    Solvation
    Solvation, also sometimes called dissolution, is the process of attraction and association of molecules of a solvent with molecules or ions of a solute...

  • Solution
    Solution
    In chemistry, a solution is a homogeneous mixture composed of only one phase. In such a mixture, a solute is dissolved in another substance, known as a solvent. The solvent does the dissolving.- Types of solutions :...

  • Free energy of solvation

External links