Benzoic acid

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Benzoic acid

Benzoic acid, C₇H₆O₂ (or C₆H₅COOH), is a colorless crystalline solid and the simplest aromatic carboxylic acid

Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
. The name derived from gum benzoin, which was for a long time the only source for benzoic acid. This weak acid and its salts are used as a food preservative. Benzoic acid is an important precursor for the synthesis of many other organic substances.
History
Benzoic acid was discovered in the 16th century.

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History

Benzoic acid was discovered in the 16th century. The dry distillation

Dry distillation

Dry distillation is the heating of solid materials to produce liquid or gaseous products . The method may or may not involve pyrolysis/thermolysis....
of gum benzoin first described by Nostradamus

Nostradamus

Michel de Nostredame , usually Latinized to Nostradamus, was a France apothecary and reputed Prophet who published collections of prophecy that have since become famous worldwide....
(1556), and subsequently by Alexius Pedemontanus

Alexius Pedemontanus

Alessio Piemontese, also known under his Latin name of Alexius Pedemontanus, was the pseudonym of a 16th century Italy physician, Alchemy, and author of the immensely popular book, The Secrets of Alexis of Piedmont....
(1560) and Blaise de Vigenère

Blaise de Vigenère

Blaise de Vigen?re was a France diplomat and cryptographer. The Vigen?re cipher is so named due to the cipher being incorrectly attributed to him in the 19th century....
(1596).

Justus von Liebig

Justus von Liebig

Justus von Liebig was a German chemist who made major contributions to agriculture and biology chemistry, and worked on the organization of organic chemistry....
and Friedrich Wöhler

Friedrich Wöhler

Friedrich W?hler was a Germany chemist, best-known for his synthesis of urea, but also the first to isolate several chemical elements....
determined the structure of benzoic acid in 1832. They also investigated how hippuric acid

Hippuric acid

Hippuric acid is an carboxylic acid found in the urine of horses and other herbivores. Hippuric acid crystallizes in rhombic prisms which are readily soluble in hot water, melt at 187 ?C and decompose at about 240 ?C....
is related to benzoic acid.

In 1875 Salkowski discovered the antifungal abilities of benzoic acid, which was used for a long time in the preservation of benzoate-containing cloudberry fruits

Cloudberry

The cloudberry , also called bakeapple in Newfoundland and Labrador, Cape Breton Island and southern Nova Scotia, is a slow-growing alpine or sub-Arctic species of Rubus, producing amber-colored edible fruit....
.

Production

Industrial preparations

Benzoic acid is produced commercially by partial oxidation of toluene

Toluene

Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
. The process is catalyzed by cobalt

Cobalt

Cobalt is a hard, lustrous, grey metal, a chemical element with symbol Co and atomic number 27. Although cobalt-based colors and pigments have been used since ancient times, and miners have long used the name kobold ore for some minerals, cobalt was only discovered in 1735 by Georg Brandt....
or manganese

Manganese

Manganese is a chemical element, designated by the symbol Mn. It has the atomic number 25. It is found as a Oxidation state in nature , and in many minerals....
naphthenate

Naphthenate

Naphthenates are the salt of naphthenic acids, which are an acidic fraction from petroleum processing, and which are composed of a mixture of organic acids, especially cycloalkyl carboxylic acids....
s. The process uses cheap raw materials, proceeds in high yield, and is considered environmentally green.

U.S. production capacity is estimated to be 126,000 tonne

Tonne

A tonne or metric ton , also referred to as a metric tonne, is a measurement of mass equal to 1,000 kilograms, or 2204.6226 pounds....
s per year (139,000 tons), much of which is consumed domestically to prepare other industrial chemicals.

Laboratory synthesis

Benzoic acid is cheap and readily available, so the laboratory synthesis of benzoic acid is mainly practiced for its pedagogical value. It is a common undergraduate preparation.

For all syntheses, benzoic acid can be purified by recrystallization from water because of its high solubility in hot water and poor solubility in cold water. The avoidance of organic solvents for the recrystallization makes this experiment particularly safe. Other possible recrystallization solvents include 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....
(anhydrous

Anhydrous

As a general term, a substance is said to be anhydrous if it contains no water. The way of achieving the anhydrous form differs from one substance to another....
or aqueous), benzene

Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
, petroleum ether, and a mixture of ethanol and water.

By hydrolysis

Like any other nitrile

Nitrile

A nitrile is any organic compound which has a -Carbon=Nitrogen functional group. The -C=N functional group is called a nitrile group....
or amide

Amide

In chemistry, an amide is one of three kinds of compounds:* the organic chemistry functional group characterized by a carbonyl group linked to a nitrogen atom , or a compound that contains this functional group ; or...
, benzonitrile

Benzonitrile

Benzonitrile is the chemical compound with the formula C6H5CN, abbreviated PhenylCN. This aromatic organic compound is colourless, with a sweet almond odour....
and benzamide

Benzamide

Benzamide is an off-white solid with the chemical formula of C6H5CONH2. It is a derivative of benzoic acid. It is slightly soluble in water, and soluble in many organic solvents....
can be hydrolyzed to benzoic acid or its conjugate base in acid or basic conditions.

From benzaldehyde

The base-induced disproportionation

Disproportionation

Disproportionation or dismutation is used to describe two particular types of chemical reaction:* A chemical reaction of the type: 2A ? A' + A" where A, A' and A" are different chemical species....
of benzaldehyde

Benzaldehyde

Benzaldehyde is a chemical compound consisting of a benzene ring with an aldehyde substituent. It is the simplest representative of the aromatic aldehydes and one of the most industrially used members of this family of compounds....
, the Cannizzaro reaction

Cannizzaro reaction

The Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction that involves the base -induced disproportionation of an aldehyde lacking a hydrogen atom in the alpha position....
, affords equal amounts of benzoate and benzyl alcohol

Benzyl alcohol

Benzyl alcohol is an organic compound with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn", thus benzyl alcohol is denoted as BnOH....
; the latter can be removed by distillation

Distillation

Distillation is a method of separation process mixtures based on differences in their Volatility in a boiling liquid mixture. Distillation is a unit operation, or a physical separation process, and not a chemical reaction....
.

From bromobenzene

Bromobenzene

Bromobenzenes are a group of halocarbons formed in a substitution reaction between bromine and benzene with a hydrogen bromide by-product. The name strictly refers to monobromobenzene, a benzene with a single bromine; however it can be used to refer to a benzene containing any number of bromine molecules....
can be converted to benzoic acid by "carbonation" of the intermediate phenylmagnesium bromide

Phenylmagnesium bromide

Phenylmagnesium bromide, with the simplified formula C6H5MgBr, is a magnesium-containing organometallic compound. It is so commonly used that it is commercially available as a solution in diethyl ether or tetrahydrofuran ....
:

C₆H₅MgBr + CO₂ ? C₆H₅CO₂MgBr

C₆H₅CO₂MgBr + HCl ? C₆H₅CO₂H + MgBrCl

From benzyl alcohol

Benzyl alcohol

Benzyl alcohol is an organic compound with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn", thus benzyl alcohol is denoted as BnOH....
is refluxed with potassium permanganate or other oxidizing reagents in water. The mixture is hot filtered to remove manganese dioxide and then allowed to cool to afford benzoic acid.

Historical preparations

The first industrial process involved the reaction of benzotrichloride

Benzotrichloride

Benzotrichloride, is an organic compound with the chemical formula C6H5CCl3. It is principally used as an intermediate in the preparation of other chemical products such as dyes....
(trichloromethyl benzene) with calcium hydroxide

Calcium hydroxide

Calcium hydroxide, traditionally called slaked lime, hydrated lime, or pickling lime, is a chemical compound with the chemical formula Calcium2....
in water, using iron

Iron

Iron is a chemical element with the symbol Fe and atomic number 26. Iron is a Group 8 element and period 4 element. Iron is lustrous and silvery in color....
or iron salts

Iron(III) chloride

Iron chloride, Generic name called ferric chloride, is an industrial scale commodity chemical compound, with the formula IronChlorine3....
as catalyst. The resulting calcium benzoate

Calcium benzoate

Calcium benzoate is the calcium salt of benzoic acid. It is used in the food industry as a preservative; its E number is E213....
is converted to benzoic acid with hydrochloric acid

Hydrochloric acid

Hydrochloric acid is the solution of hydrogen chloride in water. It is a highly corrosive, strong acid mineral acid and has major industrial uses....
. The product contains significant amounts of chlorinated benzoic acid derivatives. For this reason, benzoic acid for human consumption was obtained by dry distillation of gum benzoin. Food-grade benzoic acid is now produced synthetically.

Alkyl

Alkyl

An alkyl is a univalent Radical consisting of carbon and hydrogen atoms, arranged in a chain. The Alkyls form homologous series with the general formula CnH2n+1....
substituted benzene

Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
derivatives give benzoic acid with the stoichiometric oxidants potassium permanganate

Potassium permanganate

Potassium permanganate is the inorganic chemical compound potassiummanganeseoxygen4, a water soluble salt consisting of equal Mole amounts of potassium and permanganate ions....
, chromium trioxide

Chromium trioxide

The acid anhydride of chromic acid, CrO3, is chromium trioxide or chromium oxide; industrially, this compound is sometimes sold as "chromic acid"....
, nitric acid

Nitric acid

Nitric acid , also known as aqua fortis and spirit of nitre, is a highly corrosion and toxic strong acid that can cause severe burns....
.

Uses

Feedstock

Benzoic acid is used to make a large number of chemicals, important examples of which are:

Benzoyl chloride
Benzoyl chloride

Benzoyl chloride, also known as benzenecarbonyl chloride, is a colourless, fuming liquid, C6H5COCl, with an irritating odour....
, C₆H₅C(O)Cl, is obtained by treatment of benzoic with thionyl chloride
Thionyl chloride

Thionyl chloride is an inorganic compound with the chemical formula SulfurOxygenChlorine2. It is a reactive chemical reagent used in chlorination chemical reaction....
, phosgene
Phosgene

Phosgene is the chemical compound with the chemical formula COCl2. This colorless gas gained infamy as a chemical weapon during World War I, but it is also a valued industrial reagent and building block in organic synthesis....
or one of the chlorides of phosphorus
Phosphorus chlorides

Phosphorus pentachloride is the chemical compound with the formula PCl5. It is one of the most important phosphorus chlorides, others being phosphorus trichloride and phosphorus oxytrichloride....
. C₆H₅C(O)Cl is an important starting material for several benzoic acid derivates like benzyl benzoate
Benzyl benzoate

Benzyl benzoate is the ester of benzyl alcohol and benzoic acid, with the formula C6H5CH2O2CC6H5....
, which is used in artificial flavours and insect repellent
Insect repellent

An insect repellent is a substance applied to skin, clothing, or other surfaces which discourages insects from landing or climbing on that surface....
s.
Benzoate plasticizer
Plasticizer

Plasticizers or Dispersants are additives that increase the plasticity or fluidity of the material to which they are added, these include plastics, cement, concrete, wallboard and clay bodies....
s, such as the glycol-, diethylengylcol-, and triethyleneglycol esters, are obtained by transesterification
Transesterification

In organic chemistry, transesterification is the process of exchanging the alcohol group of an ester compound with another alcohol. These reactions are often catalyst by the addition of an acid or base ....
of methyl benzoate
Methyl benzoate

Methyl benzoate is an ester with the chemical formula C6H5COOCH3. It is formed by the condensation of methanol and benzoic acid....
with the corresponding diol
Diol

A diol or glycol is a chemical compound containing two hydroxyl groups Vicinal diols have hydroxyl groups attached to adjacent atoms. Examples of vicinal diol compounds are ethylene glycol and propylene glycol....
. Alternatively these species arise by treatment of benzoylchloride with the diol. These plasticizers are used similarly to those derived from terephthalic acid ester.
Phenol
Phenol

Phenol, also known as carbolic acid, is a toxic, white crystalline solid with a sweet tarry odor, commonly referred to as a "hospital smell"....
, C₆H₅OH, is obtained by oxidative decarboxylation
Decarboxylation

Decarboxylation is any chemical reaction in which a carboxyl group is split off from a compound as carbon dioxide ....
at 300-400°C. The temperature required can be lowered to 200°C by the addition of catalytic amounts of copper(II) salts
Copper

Copper is a chemical element with the symbol Cu and atomic number 29.It is a ductile metal with very high thermal and electrical conductivity....
. The phenol can be converted to cyclohexanol
Cyclohexanol

Cyclohexanol is the organic compound with the Chemical formula 5CHOH. The molecule is related to cyclohexane ring by replacement of one hydrogen atom by a hydroxide....
, which is a starting material for nylon
Nylon

Nylon is a generic designation for a family of synthetic polymers known generically as polyamides and first produced on February 28, 1935 by Wallace Carothers at DuPont....
synthesis.

Food preservative

Benzoic acid and its salts are used as a food preservative

Preservative

A preservative is a natural or synthetic chemical compound that is added to products such as foods, pharmaceuticals, paints, biological samples, wood, etc....
, represented by the E-numbers E210, E211

Sodium benzoate

Sodium benzoate , also called benzoate of soda, has the chemical formula NaC6H5CO2. It is the sodium salt of benzoic acid and exists in this form when dissolved in water....
, E212

Potassium benzoate

Potassium benzoate , the potassium salt of benzoic acid, is a food preservative that inhibits the growth of mold, yeast and some bacterium. It works best in low-pH products, below 4.5, where it exists as benzoic acid....
, and E213

Calcium benzoate

Calcium benzoate is the calcium salt of benzoic acid. It is used in the food industry as a preservative; its E number is E213....
. Benzoic acid inhibits the growth of mold

Mold

Molds include all species of microscopic fungi that grow in the form of Multicellular organism filaments, called hyphae. In contrast, microscopic fungi that grow as single cells are called yeasts....
, yeast

Yeast

Yeasts are eukaryote microorganisms classified in the Kingdom fungus, with about 1,500 species currently described; they dominate fungal diversity in the oceans....
and some bacteria. It is either added directly or created from reactions with its sodium

Sodium

Sodium is an element which has the symbol Na , atomic number 11, atomic mass 23 amu , and a common oxidation number +1. Sodium is a soft, silvery white, highly reactive element and is a member of the alkali metals within "group 1" ....
, potassium

Potassium

Potassium is a chemical element. It has the symbol K , atomic number 19, and atomic mass 39.0983. Potassium was first isolated from potash, hence the name....
, or calcium

Calcium

Calcium is the chemical element with the symbol Ca and atomic number 20. It has an atomic mass of 40.078 amu. Calcium is a soft grey alkaline earth metal, and is the fifth most abundant element by mass in the earth's Crust ....
salt. The mechanism starts with the absorption of benzoic acid in to the cell. If the intracellular pH

pH is a measure of the Acid or Base of a solution. It is defined as the cologarithm of the Activity of dissolved hydrogen ions . Hydrogen ion activity coefficients cannot be measured experimentally, so they are based on theoretical calculations....
changes to 5 or lower, the anaerobic fermentation

Fermentation (biochemistry)

Fermentation is the process of deriving energy from the Redox of organic compounds, such as carbohydrates, using an Endogeny electron acceptor, which is usually an organic compound....
of glucose

Glucose

Glucose , a monosaccharide also known as grape sugar, blood sugar, or corn sugar, is a very important carbohydrate in biology....
through phosphofructokinase

Phosphofructokinase

Phosphofructokinase-1 is the most important regulatory enzyme of glycolysis. It is an allosteric enzyme made of 4 subunits and controlled by several activators and Enzyme inhibitors....
is decreased by 95%. The efficacy of benzoic acid and benzoate is thus dependent on the pH of the food. Acidic food and beverage like fruit juice (citric acid

Citric acid

Citric acid is a weak organic chemistry acid, and it is a natural preservative and is also used to add an acidic, or sour, taste to foods and soft drinks....
), sparkling drinks (carbon dioxide

Carbon dioxide

Carbon dioxide is a chemical compound composed of two oxygen atoms covalent bond to a single carbon atom. It is a gas at standard temperature and pressure and exists in Earth's atmosphere in this state....
), soft drinks (phosphoric acid

Phosphoric acid

Phosphoric acid, also known as orthophosphoric acid or phosphoric acid, is a mineral acid having the chemical formula Hydrogen3PhosphorusOxygen4....
), pickles

Pickling

Pickling, also known as brining or corning, is the process of preserving food by Anaerobic organism fermentation in brine , to produce lactic acid bacteria, or marination and storing it in an acid solution, usually vinegar ....
(vinegar

Vinegar

Vinegar is an acidic liquid processed from the fermentation of ethanol in a process that yields its key ingredient, acetic acid . It also may come in a diluted form....
) or other acidified food are preserved with benzoic acid and benzoates.

Typical levels of use for benzoic acid as a preservative in food are between 0.05 – 0.1%. Foods in which benzoic acid may be used and maximum levels for its application are laid down in international food law.

Concern has been expressed that benzoic acid and its salts may react with ascorbic acid

Ascorbic acid

Ascorbic acid is a sugar acid with antioxidant properties. Its appearance is white to light-yellow crystals or powder. It is water-soluble. The L-enantiomer of ascorbic acid is commonly known as vitamin C....
(vitamin C) in some soft drinks, forming small quantities of benzene

Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
.

Medicinal

Benzoic acid is a constituent of Whitfield's Ointment

Whitfield's Ointment

Whitfield's Ointment is salicylic acid and benzoic acid in a suitable base, such as lanolin or vaseline..It is used for the treatment of fungal infections, such as athlete's foot....
which is used for the treatment of fungal skin diseases such as tinea, ringworm

Ringworm

Ringworm is a fungal infection of the skin in humans and domestic animals such as sheep and cattle. Fungi are organisms that survive by eating plant or animal material....
, and athlete's foot

Athlete's foot

Athlete's foot is a fungal infection of the skin that causes scaling, flaking, and itching of affected areas. It is typically transmitted in moist areas where people walk barefoot, such as showers or bathhouses....
.

Biology and health effects

Benzoic acid occurs naturally free and bound as benzoic acid esters in many plant and animal species. Appreciable amounts have been found in most berries (around 0.05%). Ripe fruits of several Vaccinium
Vaccinium

Vaccinium is a genus of shrubs or dwarf shrubs in the plant Family Ericaceae. The fruit of many species are eaten by humans and some are of commercial importance, including the cranberry, blueberry, bilberry or whortleberry, lingonberry or cowberry, and huckleberry ....
species (e.g., cranberry

Cranberry

Cranberries are a group of evergreen dwarf shrubs or trailing vines in the genus Vaccinium subgenus Oxycoccos, or in some treatments, in the distinct genus Oxycoccos....
, V. vitis idaea; bilberry

Bilberry

Bilberry is a name given to several species of low-growing shrubs in the genus Vaccinium that bears false berrys. The species most often referred to is Vaccinium myrtillus L., otherwise known as the European blueberry....
, V. macrocarpon) contain as much as 300-1300 mg free benzoic acid per kg fruit. Benzoic acid is also formed in apple

APPLE

This article is about the satellite APPLE. For the fruit apple, see Apple. For other uses see Apple .The Ariane Passenger PayLoad Experiment , was an experimental communication satellite with a C-Band transponder launched by Indian Space Research Organisation satellite on June 19, 1981 by Ariane 1, a launch vehicle of the European Spac...
s after infection with the fungus Nectria galligena. Among animals, benzoic acid has been identified primarily in omnivorous or phytophageous species, e.g., in viscera and muscles of the ptarmigan

Ptarmigan

The Ptarmigan, Lagopus mutaThe word ptarmigan comes from the Scottish Gaelic language t?rmachan, which may be related to torm "murmur"....
(Lagopus mutus) as well as in gland secretions of male muskoxen (Ovibos moschatus) or Asian bull elephants (Elephas maximus).

Gum benzoin contains up to 20% of benzoic acid and 40% benzoic acid esters.

Benzoic acid is present as part of hippuric acid

Hippuric acid

Urine

Urine is a liquid waste product of the body secreted by the kidneys by a process of filtration from blood called urination and excreted through the urethra....
of mammals, especially herbivores (Gr. hippos = horse; ouron = urine). Humans produce about 0.44 g/L hippuric acid

Hippuric acid

Toluene

Toluene, also known as methylbenzene or phenylmethane, is a clear, Water -insoluble liquid with the typical smell of paint thinners, redolent of the sweet smell of the related compound benzene....
or benzoic acid it can rise above that level.

For humans, the WHO's International Programme on Chemical Safety (IPCS) suggests a provisional tolerable intake would be 5 mg/kg body weight per day. Cats have a significantly lower tolerance against benzoic acid and its salts than rats

RATS

RATS may refer to:* RATS , Regression Analysis of Time Series, a statistical package* Rough Auditing Tool for Security, a computer program...
and mice

Mouse

A mouse is a small animal that belongs to one of numerous species of rodents. The best known mouse species is the House Mouse . It is also a popular pet....
. Lethal dose for cats can be as low as 300 mg/kg body weight. The oral LD₅₀

LD50

In toxicology, the median lethal dose, LD50 , or LCt50 of a toxic substance or radiation is the Dose required to kill half the members of a tested population....
for rats is 3040 mg/kg, for mice it is 1940-2263 mg/kg.

Chemistry

Reactions of benzoic acid can occur at either the aromatic ring

Aromaticity

Aromaticity is a chemical property in which a conjugated system ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone....
or the carboxyl group

Carboxyl group

A carboxyl group is a set of four atoms bonded together and present in carboxylic acids, including amino acid. Usually abbreviated as either CO2H or COOH, this set of atoms constitutes a functional group....
:

Aromatic ring

Electrophilic aromatic substitution

Electrophilic aromatic substitution or EAS is an organic reaction in which an atom, usually hydrogen, appended to an aromatic ring is replaced by an electrophile....
reaction will take place mainly in 3-position to the electron-withdrawing carboxylic group; i.e. benzoic acid is meta directing

Electrophilic aromatic substitution

Electrophilic aromatic substitution or EAS is an organic reaction in which an atom, usually hydrogen, appended to an aromatic ring is replaced by an electrophile....
.

The second substitution reaction (on the right) is slower because the first nitro group is deactivating. Conversely, if an activating group (electron-donating) was introduced (e.g., alkyl), a second substitution reaction would occur more readily than the first and the disubstituted product might not accumulate to a significant extent.

Carboxyl group

All the reactions mentioned for carboxylic acid

Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
s are also possible for benzoic acid.

Benzoic acid esters are the product of the acid catalysed reaction with alcohols.
Benzoic acid amide
Amide

In chemistry, an amide is one of three kinds of compounds:* the organic chemistry functional group characterized by a carbonyl group linked to a nitrogen atom , or a compound that contains this functional group ; or...
s are more easily available by using activated acid derivatives (such as benzoyl chloride
Benzoyl chloride

Benzoyl chloride, also known as benzenecarbonyl chloride, is a colourless, fuming liquid, C6H5COCl, with an irritating odour....
) or by coupling reagents used in peptide synthesis
Peptide synthesis

In organic chemistry, peptide synthesis is the production of peptides, which are organic compounds in which multiple amino acids are linked via peptide bonds which are also known as amide bonds....
like DCC
Dicyclohexylcarbodiimide

Dicyclohexylcarbodiimide is an organic compound with chemical formula C13H22N2 whose primary use is to couple amino acids during artificial peptide synthesis....
and DMAP.
The more active benzoic anhydride is formed by dehydration using acetic anhydride
Acetic anhydride

Acetic anhydride is the chemical compound with the chemical formula 2O. Commonly abbreviated Acetyl2O, it is one of the simplest acid anhydrides and is a widely used reagent in organic synthesis....
or phosphorus pentoxide
Phosphorus pentoxide

Phosphorus pentoxide is a chemical compound with formula Phosphorus2Oxygen5. This white crystalline solid is the anhydride of phosphoric acid....
.
Highly reactive acid derivatives such as acid halides
Acyl halide

An acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.If the acid is a carboxylic acid, the compound contains a ?COX functional group, which consists of a carbonyl group singly bonded to a halogen atom....
are easily obtained by mixing with halogenation
Halogenation

Halogenation is a chemical reaction that incorporates a halogen atom into a molecule. More specific descriptions exist that specify the type of halogen: fluorination, chlorination, bromination, and iodination....
agents like phosphorus chlorides
Phosphorus chlorides

Phosphorus pentachloride is the chemical compound with the formula PCl5. It is one of the most important phosphorus chlorides, others being phosphorus trichloride and phosphorus oxytrichloride....
or thionyl chloride
Thionyl chloride

Thionyl chloride is an inorganic compound with the chemical formula SulfurOxygenChlorine2. It is a reactive chemical reagent used in chlorination chemical reaction....
.
Orthoester
Orthoester

In organic chemistry, an orthoester is a functional group containing three alkoxy groups attached to one carbon atom. The name can also refer to any organic compound that contains this functional group....
s can be obtained by the reaction of alcohols under acidic water free conditions with benzonitrile
Benzonitrile

Benzonitrile is the chemical compound with the formula C6H5CN, abbreviated PhenylCN. This aromatic organic compound is colourless, with a sweet almond odour....
.
Reduction to benzaldehyde
Benzaldehyde

Benzaldehyde is a chemical compound consisting of a benzene ring with an aldehyde substituent. It is the simplest representative of the aromatic aldehydes and one of the most industrially used members of this family of compounds....
and benzyl alcohol
Benzyl alcohol

Benzyl alcohol is an organic compound with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn", thus benzyl alcohol is denoted as BnOH....
is possible using DIBAL-H, LiAlH₄
Lithium aluminium hydride

Lithium aluminium hydride , commonly abbreviated to LAH, is a reducing agent used in organic synthesis. It is more powerful than the related reagent sodium borohydride due to the weaker Al-H bond compared to the B-H bond....
or sodium borohydride
Sodium borohydride

Sodium borohydride, also known as sodium tetrahydroborate, has the chemical formula sodiumboronhydrogen4. This white solid, usually encountered as a powder, is a specialty reducing agent used in the manufacture of Pharmacologys and other organic and inorganic compounds....
.
The copper catalysed decarboxylation
Decarboxylation

Decarboxylation is any chemical reaction in which a carboxyl group is split off from a compound as carbon dioxide ....
of benzoate to benzene may be effected by heating in quinoline
Quinoline

Quinoline, also known as 1-azanaphthalene, 1-benzazine, or benzo[b]pyridine, is a heterocyclic aromatic organic compound. It has the formula C9H7N and is a colourless hygroscopic liquid with a strong odour....
. Also, Hunsdiecker decarboxylation can be achieved by forming the silver salt and heating.

Benzoic acid

History

Production

Industrial preparations

Laboratory synthesis

By hydrolysis

From benzaldehyde

From bromobenzene

From benzyl alcohol

Historical preparations

Uses

Feedstock

Food preservative

Medicinal

Biology and health effects

Chemistry

Aromatic ring

Carboxyl group

Further reading

External links