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Benzoic acid
Benzoic acid
/bɛnˈzoʊ.ɪk/, C7H6O2 (or C6H5COOH), is a colorless crystalline solid and a simple aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only known source. Benzoic acid
Benzoic acid
occurs naturally in many plants[8] and serves as an intermediate in the biosynthesis of many secondary metabolites. Salts of benzoic acid are used as food preservatives and benzoic acid is an important precursor for the industrial synthesis of many other organic substances. The salts and esters of benzoic acid are known as benzoates /ˈbɛnzoʊ.eɪt/.

Contents

1 History 2 Production

2.1 Industrial preparations 2.2 Laboratory synthesis

2.2.1 By hydrolysis 2.2.2 From benzaldehyde 2.2.3 From bromobenzene 2.2.4 From benzyl alcohol 2.2.5 From benzyl chloride 2.2.6 Historical preparation

3 Uses

3.1 Precursor to plasticizers 3.2 Precursor to sodium benzoate and related preservatives 3.3 Medicinal 3.4 Benzoyl chloride 3.5 Niche and laboratory uses

4 Biology and health effects 5 Reactions

5.1 Aromatic ring 5.2 Carboxyl group

6 References 7 External links

History[edit] Benzoic acid
Benzoic acid
was discovered in the sixteenth century. The dry distillation of gum benzoin was first described by Nostradamus
Nostradamus
(1556), and then by Alexius Pedemontanus (1560) and Blaise de Vigenère (1596).[9] Pioneer work in 1830 through a variety of experiences based on amygdalin, obtained from bitter almonds (the fruit of Prunus dulcis) oil by Pierre Robiquet
Pierre Robiquet
and Antoine Boutron-Charlard, two French chemists, had produced benzaldehyde [10] but they failed in working out a proper interpretation of the structure of amygdalin that would account for it, and thus missed the identification of the benzoyl radical C7H5O. This last step was achieved some few months later (1832) by Justus von Liebig
Justus von Liebig
and Friedrich Wöhler, who determined the composition of benzoic acid.[11] These latter also investigated how hippuric acid 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.[12] It is also one of the chemical compounds found in castoreum. This compound is gathered from the castor sacs of the North American beaver. Production[edit] Industrial preparations[edit] Benzoic acid
Benzoic acid
is produced commercially by partial oxidation of toluene with oxygen. The process is catalyzed by cobalt or manganese naphthenates. The process uses abundant materials, and proceeds in high yield.[13]

Laboratory synthesis[edit] Benzoic acid
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. Benzoic acid
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. This process usually gives a yield of around 65% [14] The solubility of benzoic acid in over 40 solvents with references to original sources can be found as part of the Open Notebook Science Challenge.[15] By hydrolysis[edit] Like other nitriles and amides, benzonitrile and benzamide can be hydrolyzed to benzoic acid or its conjugate base in acid or basic conditions. From benzaldehyde[edit] The base-induced disproportionation of benzaldehyde, the Cannizzaro reaction, affords equal amounts of benzoate and benzyl alcohol; the latter can be removed by distillation.

From bromobenzene[edit] Bromobenzene
Bromobenzene
can be converted to benzoic acid by "carboxylation" of the intermediate phenylmagnesium bromide.[16] This synthesis offers a convenient exercise for students to carry out a Grignard reaction, an important class of carbon–carbon bond forming reaction in organic chemistry.[17][18][19][20][21] From benzyl alcohol[edit] Benzyl alcohol
Benzyl alcohol
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. From benzyl chloride[edit] Benzoic acid
Benzoic acid
can be prepared by oxidation of benzyl chloride in the presence of alkaline KMnO4:

C6H5CH2Cl + 2 KOH + 2 [O] → C6H5COOH + KCl + H2O

Historical preparation[edit] The first industrial process involved the reaction of benzotrichloride (trichloromethyl benzene) with calcium hydroxide in water, using iron or iron salts as catalyst. The resulting calcium benzoate is converted to benzoic acid with hydrochloric acid. 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. Uses[edit] Benzoic acid
Benzoic acid
is mainly consumed in the production of phenol by oxidative decarboxylation at 300−400 °C:[22]

C6H5CO2H + 1/2 O2 → C6H5OH + CO2

The temperature required can be lowered to 200 °C by the addition of catalytic amounts of copper(II) salts. The phenol can be converted to cyclohexanol, which is a starting material for nylon synthesis. Precursor to plasticizers[edit] Benzoate
Benzoate
plasticizers, such as the glycol-, diethyleneglycol-, and triethyleneglycol esters, are obtained by transesterification of methyl benzoate with the corresponding diol. Alternatively these species arise by treatment of benzoylchloride with the diol. These plasticizers are used similarly to those derived from terephthalic acid ester. Precursor to sodium benzoate and related preservatives[edit] Benzoic acid
Benzoic acid
and its salts are used as a food preservatives, represented by the E-numbers
E-numbers
E210, E211, E212, and E213. Benzoic acid inhibits the growth of mold, yeast[23] and some bacteria. It is either added directly or created from reactions with its sodium, potassium, or calcium salt. The mechanism starts with the absorption of benzoic acid into the cell. If the intracellular pH changes to 5 or lower, the anaerobic fermentation of glucose through phosphofructokinase is decreased by 95%. The efficacy of benzoic acid and benzoate is thus dependent on the pH of the food.[24] Acidic food and beverage like fruit juice (citric acid), sparkling drinks (carbon dioxide), soft drinks (phosphoric acid), pickles (vinegar) 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 controlled by international food law.[25][26] Concern has been expressed that benzoic acid and its salts may react with ascorbic acid (vitamin C) in some soft drinks, forming small quantities of benzene.[27] See also: Benzene
Benzene
in soft drinks Medicinal[edit] Benzoic acid
Benzoic acid
is a constituent of Whitfield's ointment which is used for the treatment of fungal skin diseases such as tinea, ringworm, and athlete's foot.[28][29] As the principal component of gum benzoin, benzoic acid is also a major ingredient in both tincture of benzoin and Friar's balsam. Such products have a long history of use as topical antiseptics and inhalant decongestants. Benzoic acid
Benzoic acid
was used as an expectorant, analgesic, and antiseptic in the early 20th century.[30] Benzoyl chloride[edit] Benzoic acid
Benzoic acid
is a precursor to benzoyl chloride, C6H5C(O)Cl by treatment with thionyl chloride, phosgene or one of the chlorides of phosphorus. Benzoyl chloride
Benzoyl chloride
is an important starting material for several benzoic acid derivates like benzyl benzoate, which is used in artificial flavours and insect repellents. Niche and laboratory uses[edit] In teaching laboratories, benzoic acid is a common standard for calibrating a bomb calorimeter.[31] Biology and health effects[edit] Benzoic acid
Benzoic acid
is relatively nontoxic. It is excreted as hippuric acid.[32] Benzoic acid
Benzoic acid
is metabolized by butyrate-CoA ligase into an intermediate product, benzoyl-CoA,[33] which is then metabolized by glycine N-acyltransferase into hippuric acid.[34] Benzoic acid
Benzoic acid
occurs naturally as do its esters in many plant and animal species. Appreciable amounts have been found in most berries (around 0.05%). Ripe fruits of several Vaccinium
Vaccinium
species (e.g., cranberry, V. vitis macrocarpon; bilberry, V. myrtillus) contain as much as 0.03–0.13% free benzoic acid. Benzoic acid
Benzoic acid
is also formed in apples 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 rock ptarmigan (Lagopus muta) as well as in gland secretions of male muskoxen (Ovibos moschatus) or Asian bull elephants (Elephas maximus).[35] Gum benzoin contains up to 20% of benzoic acid and 40% benzoic acid esters.[36] Cryptanaerobacter phenolicus is a bacterium species that produces benzoate from phenol via 4-hydroxybenzoate[37] Benzoic acid
Benzoic acid
is present as part of hippuric acid (N-benzoylglycine) in urine of mammals, especially herbivores (Gr. hippos = horse; ouron = urine). Humans produce about 0.44 g/L hippuric acid in their urine, and if the person is exposed to toluene or benzoic acid, it can rise above that level.[38] For humans, the World Health Organization's International Programme on Chemical Safety (IPCS) suggests a provisional tolerable intake would be 5 mg/kg body weight per day.[35] Cats have a significantly lower tolerance against benzoic acid and its salts than rats and mice. Lethal dose for cats can be as low as 300 mg/kg body weight.[39] The oral LD50 for rats is 3040 mg/kg, for mice it is 1940–2263 mg/kg.[35] In Taipei, Taiwan, a city health survey in 2010 found that 30% of dried and pickled food products had benzoic acid.[40] Reactions[edit] Reactions of benzoic acid can occur at either the aromatic ring or at the carboxyl group: Aromatic ring[edit]

Electrophilic aromatic substitution
Electrophilic aromatic substitution
reaction will take place mainly in 3-position due to the electron-withdrawing carboxylic group; i.e. benzoic acid is meta directing. The second substitution reaction (on the right) is slower because the first nitro group is deactivating.[41] 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 accumulate to a significant extent. Carboxyl group[edit] All the reactions mentioned for carboxylic acids are also possible for benzoic acid.

Benzoic acid
Benzoic acid
esters are the product of the acid catalysed reaction with alcohols. Benzoic acid
Benzoic acid
amides are more easily available by using activated acid derivatives (such as benzoyl chloride) or by coupling reagents used in peptide synthesis like DCC and DMAP. The more active benzoic anhydride is formed by dehydration using acetic anhydride or phosphorus pentoxide. Highly reactive acid derivatives such as acid halides are easily obtained by mixing with halogenation agents like phosphorus chlorides or thionyl chloride. Orthoesters can be obtained by the reaction of alcohols under acidic water free conditions with benzonitrile. Reduction to benzaldehyde and benzyl alcohol is possible using DIBAL-H, LiAlH4 or sodium borohydride. The copper catalysed decarboxylation of benzoate to benzene may be effected by heating in quinoline. Also, Hunsdiecker decarboxylation can be achieved by forming the silver salt and heating. Benzoic acid can also be decarboxylated by heating with an alkali hydroxide or calcium hydroxide.

References[edit]

^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 745. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.  ^ a b c d e f g h i j k http://chemister.ru/Database/properties-en.php?dbid=1&id=679 ^ Seidell, Atherton; Linke, William F. (1952). Solubilities of Inorganic and Organic Compounds. Van Nostrand. Retrieved 2014-05-29.  ^ a b c Benzoic acid
Benzoic acid
in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD), http://webbook.nist.gov (retrieved 2014-05-23) ^ Harris, Daniel (2010). Quantitative Chemical Analysis (8 ed.). New York: W. H. Freeman and Company. pp. AP12. ISBN 9781429254366.  ^ a b c d Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health ^ a b c Sigma-Aldrich
Sigma-Aldrich
Co., Benzoic acid. Retrieved on 2014-05-23. ^ "Scientists uncover last steps for benzoic acid creation in plants". Purdue Agriculture News.  ^ Neumüller O-A (1988). Römpps Chemie-Lexikon (6 ed.). Stuttgart: Frankh'sche Verlagshandlung. ISBN 3-440-04516-1. OCLC 50969944.  ^ Nouvelles expériences sur les amandes amères et sur l'huile volatile qu'elles fournissent Robiquet, Boutron-Charlard, Annales de chimie et de physique, 44 (1830), 352–382, ^ Liebig J; Wöhler F (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Chemie. 3 (3): 249–282. doi:10.1002/jlac.18320030302.  ^ Salkowski E (1875). Berl Klin Wochenschr. 12: 297–298.  Missing or empty title= (help) ^ Wade, Leroy G. (2014). Organic chemistry (Pearson new international edition ed.). Harlow: Pearson Education Limited. p. 985. ISBN 1-292-02165-9. CS1 maint: Extra text (link) ^ D. D. Perrin; W. L. F. Armarego (1988). Purification of Laboratory Chemicals (3rd ed.). Pergamon Press. p. 94. ISBN 0-08-034715-0.  ^ solubility of benzoic acid in organic solvents ^ Donald L. Pavia (2004). Introduction to Organic Laboratory Techniques: A Small Scale Approach. Thomson Brooks/Cole. pp. 312–314. ISBN 0-534-40833-8.  ^ Shirley, D. A. (1954). "The Synthesis of Ketones from Acid Halides and Organometallic Compounds of Magnesium, Zinc, and Cadmium". Org. React. 8: 28–58.  ^ Huryn, D. M. (1991). "Carbanions of Alkali and Alkaline Earth Cations: (ii) Selectivity of Carbonyl Addition Reactions". In Trost, B. M.; Fleming, I. Comprehensive Organic Synthesis, Volume 1: Additions to C—X π-Bonds, Part 1. Elsevier Science. pp. 49–75. ISBN 978-0-08-052349-1.  ^ Portland Community College. "The Grignard Reaction. Preparation of Benzoic Acid" <"Archived copy" (PDF). Archived from the original (PDF) on 26 February 2015. Retrieved 12 March 2015. > ^ University of Wisconsin-Madison. "Experiment 9: Synthesis of Benzoic Acid via Carbonylation of a Grignard Reagent" <http://www.chem.wisc.edu/courses/342/Fall2004/Experiment_9.pdf> ^ Towson University. "Experiment 3: Preparation of Benzoic Acid"<"Archived copy" (PDF). Archived from the original (PDF) on 13 April 2015. Retrieved 12 March 2015. > ^ Maki, Takao; Takeda, Kazuo (2000). "Benzoic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a03_555. ISBN 3527306730. . ^ A D Warth (1 December 1991). "Mechanism of action of benzoic acid on Zygosaccharomyces bailii: effects on glycolytic metabolite levels, energy production, and intracellular pH". Appl Environ Microbiol. 57 (12): 3410–4. PMC 183988 . PMID 1785916.  ^ Pastrorova I, de Koster CG, Boom JJ (1997). "Analytic Study of Free and Ester
Ester
Bound Benzoic and Cinnamic Acids of Gum Benzoin Resins by GC-MS HPLC-frit FAB-MS". Phytochem Anal. 8 (2): 63–73. doi:10.1002/(SICI)1099-1565(199703)8:2<63::AID-PCA337>3.0.CO;2-Y.  ^ GSFA Online Food Additive Group Details: Benzoates (2006) Archived 26 September 2007 at the Wayback Machine. ^ EUROPEAN PARLIAMENT AND COUNCIL DIRECTIVE No 95/2/EC of 20 February 1995 on food additives other than colours and sweeteners (Consleg-versions do not contain the latest changes in a law) Archived 19 April 2003 at the Wayback Machine. ^ BfR article Indications of the possible formation of benzene from benzoic acid in foods, BfR Expert Opinion No. 013/2006, 1 December 2005 ^ "Whitfield Ointment".  ^ Charles Owens Wilson; Ole Gisvold; John H. Block (2004). Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical. Lippincott Williams & Wilkins. p. 234. ISBN 0-7817-3481-9.  ^ Lillard, Benjamin (1919). "Practical druggist and pharmaceutical review of reviews".  ^ Experiment 2: Using Bomb Calorimetry to Determine the Resonance Energy of Benzene
Benzene
Archived 9 March 2012 at the Wayback Machine. ^ Cosmetic Ingredient Review Expert Panel Bindu Nair (2001). "Final Report on the Safety Assessment of Benzyl Alcohol, Benzoic Acid, and Sodium
Sodium
Benzoate". Int J Tox. 20 (Suppl. 3): 23–50. doi:10.1080/10915810152630729. PMID 11766131.  ^ "butyrate-CoA ligase". BRENDA. Technische Universität Braunschweig. Retrieved 7 May 2014.  section= ignored (help) ^ "glycine N-acyltransferase". BRENDA. Technische Universität Braunschweig. Retrieved 7 May 2014.  section= ignored (help) ^ a b c "Concise International Chemical Assessment Document 26: BENZOIC ACID AND SODIUM BENZOATE".  ^ Tomokuni K, Ogata M (1972). "Direct Colorimetric Determination of Hippuric Acid in Urine". Clin Chem. 18 (4): 349–351. PMID 5012256.  ^ Juteau, Pierre; Valérie Côté; Marie-France Duckett; Réjean Beaudet; François Lépine; Richard Villemur; Jean-Guy Bisaillon (January 2005). " Cryptanaerobacter phenolicus gen. nov., sp. nov., an anaerobe that transforms phenol into benzoate via 4-hydroxybenzoate". International Journal of Systematic and Evolutionary Microbiology. 55 (1): 245–250. doi:10.1099/ijs.0.02914-0. PMID 15653882.  ^ Krebs HA, Wiggins D, Stubbs M (1983). "Studies on the mechanism of the antifungal action of benzoate" (PDF). Biochem J. 214 (3): 657–663. PMC 1152300 . PMID 6226283.  ^ Bedford PG, Clarke EG (1972). "Experimental benzoic acid poisoning in the cat". Vet Rec. 90 (3): 53–58. doi:10.1136/vr.90.3.53. PMID 4672555.  ^ Chen, Jian; Y.L. Kao (18 January 2010). "Nearly 30% dried, pickled foods fail safety inspections". The China Post.  ^ Brewster, R. Q.; Williams, B.; Phillips, R. (1955). "3,5-Dinitrobenzoic Acid". Organic Syntheses. ; Collective Volume, 3, p. 337 

External links[edit]

Wikimedia Commons has media related to Benzoic acid.

International Chemical Safety Card 0103 SIDS Initial Assessment Report for Benzoic Acid from the Organisation for Economic Co-operation and Development (OECD) ChemicalLand

v t e

Local anesthetics (primarily sodium channel blockers) (N01B)

Esters by acid

Aminobenzoic

Benzocaine Butacaine Butamben Chloroprocaine Dimethocaine Lucaine Meprylcaine Metabutethamine Metabutoxycaine Nitracaine Orthocaine Propoxycaine Procaine
Procaine
(Novocaine) Proxymetacaine Risocaine Tetracaine

Benzoic

Amylocaine Cocaine Cyclomethycaine α-Eucaine β-Eucaine Hexylcaine Isobucaine Piperocaine

ArCO2- (not para-amino or Ph)

Amoproxan (3,4,5-Trimethoxybenzoyl) 3-(p-Fluorobenzoyloxy)tropane

Amides

Articaine Bupivacaine# / Levobupivacaine / Ropivacaine Butanilicaine Carticaine Dibucaine Etidocaine Lidocaine# Mepivacaine Prilocaine Trimecaine

Combinations

Lidocaine / prilocaine Anesthetic / vasoconstrictor TAC Iontocaine

#WHO-EM ‡Withdrawn from market Clinical trials:

†Phase III §Never to phase III

v t e

Ectoparasiticides / arthropod (P03A)

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Benzoate

Benzyl benzoate#

Organophosphate

Malathion

Other/ungrouped

Dimethicone Quassia toluidine (Crotamiton)

#WHO-EM ‡Withdrawn from market Clinical trials:

†Phase III §Never to phase III

v t e

Food safety

Adulterants, food contaminants

3-MCPD Aldicarb Cyanide Formaldehyde Lead poisoning Melamine Mercury in fish Sudan I

Flavorings

Monosodium glutamate
Monosodium glutamate
(MSG) Salt Sugar

High-fructose corn syrup

Microorganisms

Botulism Campylobacter jejuni Clostridium perfringens Escherichia coli O104:H4 Escherichia coli O157:H7 Hepatitis A Hepatitis E Listeria Norovirus Rotavirus Salmonella

Parasitic infections through food

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Pesticides

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Preservatives

Benzoic acid Ethylenediaminetetraacetic acid
Ethylenediaminetetraacetic acid
(EDTA) Sodium
Sodium
benzoate

Sugar
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substitutes

Acesulfame potassium Aspartame Saccharin Sodium
Sodium
cyclamate Sorbitol Sucralose

Toxins, poisons, environment pollution

Aflatoxin Arsenic contamination of groundwater Benzene
Benzene
in soft drinks Bisphenol A Dieldrin Diethylstilbestrol Dioxin Mycotoxins Nonylphenol Shellfish poisoning

Food contamination incidents

Devon colic Swill milk scandal 1858 Bradford sweets poisoning 1900 English beer poisoning Morinaga Milk arsenic poisoning incident Minamata disease 1971 Iraq poison grain disaster Toxic oil syndrome 1993 Jack in the Box E. coli outbreak 1996 Odwalla E. coli outbreak 2006 North American E. coli outbreaks ICA meat repackaging controversy 2008 Canada listeriosis outbreak 2008 Chinese milk scandal 2008 Irish pork crisis 2008 United States salmonellosis outbreak 2011 Germany E. coli outbreak 2011 Taiwan food scandal 2011 United States listeriosis outbreak 2013 Bihar school meal poisoning 2013 horse meat scandal 2013 Taiwan food scandal 2014 Taiwan food scandal 2017 Brazil weak meat scandal 2017–18 South African listeriosis outbreak Food safety
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outbreaks death toll United States

Regulation, standards, watchdogs

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Institutions

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Secretary [32] => United Airlines Flight 736 [33] => Vampire Princess Miyu [34] => He-drum [35] => Club Med [36] => Zhuchanghe River Bridge [37] => Chinese Reunification [38] => 2008 Summer Olympics [39] => Haikou City Stadium [40] => Neyagawa [41] => Liangping [42] => AACTA Awards [43] => Assault %26 Battery %28Rose Tattoo album%29 [44] => Wuzhong District [45] => The Boxer Rebellion %28band%29 [46] => Xianling Tomb [47] => Yuan Jiajun [48] => Imperial Japanese Army [49] => China Expwy G45 sign with name [50] => Poon Choi ) TheInfoList.com
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