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Propan-1-ol
 
 
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Propan-1-ol is a primary alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
 with the formula CH3CH2CH2OH. It is also known as 1-propanol, 1-propyl alcohol, n-propyl alcohol, or simply propanol. It is an isomer
Isomer

In chemistry, isomers are compounds with the same molecular formula but different structural formulae. Isomers do not necessarily share similar properties unless they also have the same functional groups....
 of propan-2-ol. It is used as a solvent in the pharmaceutical industry, and for resins and cellulose esters. It is formed naturally in small amounts during many fermentation processes.

opanol shows the normal reactions of a primary alcohol
Primary alcohol

A primary alcohol is an alcohol which has the hydroxyl radical connected to a primary carbon. It can also be defined as a molecule containing a ??CH2OH? group....
.






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Propan-1-ol is a primary alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
 with the formula CH3CH2CH2OH. It is also known as 1-propanol, 1-propyl alcohol, n-propyl alcohol, or simply propanol. It is an isomer
Isomer

In chemistry, isomers are compounds with the same molecular formula but different structural formulae. Isomers do not necessarily share similar properties unless they also have the same functional groups....
 of propan-2-ol. It is used as a solvent in the pharmaceutical industry, and for resins and cellulose esters. It is formed naturally in small amounts during many fermentation processes.

Chemical properties

1-Propanol shows the normal reactions of a primary alcohol
Primary alcohol

A primary alcohol is an alcohol which has the hydroxyl radical connected to a primary carbon. It can also be defined as a molecule containing a ??CH2OH? group....
. Thus it can be converted to alkyl halides
Haloalkane

The haloalkanes are a group of chemical compounds, consisting of alkanes, such as methane or ethane, with one or more halogens linked, such as chlorine or fluorine, making them a type of organic halide....
; for example red phosphorus
Phosphorus

Phosphorus is the chemical element that has the symbol P and atomic number 15. The name comes from the and . A Valency nonmetal of the nitrogen group, phosphorus is commonly found in inorganic phosphate minerals....
 and iodine
Iodine

Iodine , is a chemical element that has the symbol I and atomic number 53. Naturally-occurring iodine is a single isotope with 74 neutrons....
 produce n-propyl iodide
N-Propyl iodide

n-Propyl iodide is a colorless, flammable chemical compound. It has the chemical formula C3H7I and is prepared by heating Propan-1-ol with iodine and phosphorus....
 in 90% yield, while PCl3
Phosphorus trichloride

Phosphorus trichloride is the most important of the three phosphorus chlorides. It is an important Chemical industry, being used for the manufacture of organophosphorus compounds for a wide variety of applications....
 with catalytic ZnCl2
Zinc chloride

Zinc chloride is the name of chemical compound with the chemical formula zincchlorine2 and its hydrates. Zinc chlorides, of which nine crystalline forms are known, are colorless or white and highly soluble in water....
 gives 1-chloropropane. Reaction with acetic acid
Acetic acid

Acetic acid, CH3COOH, also known as ethanoic acid, is an organic acid which gives vinegar its sour taste and pungent smell. Pure, water-free acetic acid is a colourless liquid that absorbs water from the environment , and freezes at 16.7 Celsius to a colourless crystalline solid....
 in the presence of an H2SO4
Sulfuric acid

Sulfuric acid, hydrogen2sulfuroxygen4, is a strong mineral acid. It is soluble in water at all concentrations. Sulfuric acid has many applications, and is one of the top products of the chemical industry....
 catalyst under Fischer esterification
Fischer esterification

Fischer esterification or Fischer-Speier esterification is a special type of esterification and the process of forming an ester by refluxing a carboxylic acid and an alcohol in the presence of an acid catalyst....
 conditions gives propyl acetate, while refluxing propanol overnight with formic acid alone can produce propyl formate in 65% yield. Oxidation of 1-propanol with Na2Cr2O7
Sodium dichromate

Sodium dichromate is the chemical compound with the formula sodiumChromiumOxygen. Usually, however, the salt is handled as its dihydrate Na2Cr2O7?2water of crystallization....
 and H2SO4 gives only a 36% yield of propionaldehyde
Propionaldehyde

Propionaldehyde or propanal is the organic compound with the formula CH3CH2CHO. It is a saturate 3-carbon aldehyde and is a structural isomerism of propanone....
, and therefore for this type of reaction higher yielding methods using PCC
Pyridinium chlorochromate

Pyridinium chlorochromate is a reddish orange solid reagent used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones. Pyridinium chlorochromate, or PCC, will not fully oxidize the alcohol to the carboxylic acid as does the Jones reagent....
 or the Swern oxidation
Swern oxidation

The Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol is redox to an aldehyde or ketone using oxalyl chloride, dimethyl sulfoxide and an organic base, such as triethylamine....
 are recommended. Oxidation with chromic acid
Chromic acid

Chromic acid generally refers to a collection of chemical compound generated by the acidification of solutions containing chromate and dichromate ion or the dissolving of chromium trioxide in sulfuric acid....
 yields propionic acid
Propionic acid

Propionic acid is a naturally-occurring carboxylic acid with chemical formula CarbonHydrogen3CH2COxygenOH. In the pure state, it is a colorless liquid with a pungent odor....


Propanol Reactions



Preparation

1-Propanol is a major constituent of fusel oil, a by-product formed from certain amino acid
Amino acid

In chemistry, an amino acid is a molecule containing both amine and carboxyl functional groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent....
s when potatoes or grains are fermented to produce ethanol. This is no longer a significant source of propanol.

1-Propanol is manufactured by catalytic hydrogenation
Hydrogenation

Hydrogenation is the chemical reaction that results from the addition of hydrogen . The process is usually employed to a redox or Saturation organic compounds....
 of propionaldehyde
Propionaldehyde

Propionaldehyde or propanal is the organic compound with the formula CH3CH2CHO. It is a saturate 3-carbon aldehyde and is a structural isomerism of propanone....
. The propionaldehyde is itself produced via the oxo process, by hydroformylation
Hydroformylation

Hydroformylation, also known as oxo synthesis, is an important industrial process for the production of aldehydes from alkenes. This chemical reaction entails the addition of a formyl group and a hydrogen atom to a carbon-carbon double bond....
 of ethylene
Ethylene

Ethylene is the chemical compound with the formula C2H4. It is the simplest alkene. Because it contains a carbon-carbon double bond, ethylene is called an unsaturated hydrocarbon or an olefin....
 using carbon monoxide
Carbon monoxide

Carbon monoxide, with the chemical formula CO, is a colorless and odorless, tasteless, yet highly toxic gas. Its molecules consist of one carbon atom covalent bond to one oxygen atom....
 and hydrogen
Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
 in the presence of a catalyst such as cobalt octacarbonyl
Dicobalt octacarbonyl

Dicobalt octacarbonyl is the chemical compound Co28. This metal carbonyl is a versatile reagent in organometallic chemistry and organic synthesis....
 or a rhodium
Rhodium

Rhodium is a chemical element that is a rare, silvery-white, hard transition metal and a member of the platinum group. Rhodium is found in platinum ores and is used in alloys with platinum and as a catalyst....
 complex.

H2C=CH2
Ethylene

Ethylene is the chemical compound with the formula C2H4. It is the simplest alkene. Because it contains a carbon-carbon double bond, ethylene is called an unsaturated hydrocarbon or an olefin....
  + CO
Carbon monoxide

Carbon monoxide, with the chemical formula CO, is a colorless and odorless, tasteless, yet highly toxic gas. Its molecules consist of one carbon atom covalent bond to one oxygen atom....
  + H2
Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
  ? CH3CH2CH=O
Propionaldehyde

Propionaldehyde or propanal is the organic compound with the formula CH3CH2CHO. It is a saturate 3-carbon aldehyde and is a structural isomerism of propanone....


CH3CH2CH=O + H2 ? CH3CH2CH2OH

A traditional laboratory preparation of 1-propanol involves treating n-propyl iodide
N-Propyl iodide

n-Propyl iodide is a colorless, flammable chemical compound. It has the chemical formula C3H7I and is prepared by heating Propan-1-ol with iodine and phosphorus....
 with moist Ag2O
Silver(I) oxide

Silver oxide is the chemical compound with the chemical formula Ag2O. It is a fine black or dark brown powder that is used to prepare other silver compounds....
.

History

1-Propanol was discovered in 1853 by Chancel, who obtained it by fractional distillation
Fractional distillation

Fractional distillation is the separation of a mixture into its component parts, or fractions, such as in separating chemical compound by their boiling point by heating them to a temperature at which several fractions of the compound will evaporate....
 of fusel oil.

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