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Benzoic acid From Wikipedia, the free encyclopedia
Benzoic acid /bɛnˈzoʊ.ɪk/, C7H6O2 (or
Benzoic acid
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 occurs naturally in many plants[8] and it 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/.
Benzoic acid crystals
Contents
IUPAC name Benzoic acid
1 History
Other names
2 Production 2.1 Industrial preparations
Carboxybenzene; E210; Dracylic acid; Phenylmethanoic acid; Benzenecarboxylic acid
2.2 Laboratory synthesis
Identifiers
2.2.1 By
CAS number 65850
hydrolysis
PubChem
2.2.2 From benzaldehyde
243
ChemSpider 238 UNII
8SKN0B0MIM
EC number
2006182
DrugBank
DB03793
alcohol
KEGG
D00038
2.2.5 From benzyl
MeSH
benzoic+acid
chloride
ChEBI
CHEBI:30746
ChEMBL
CHEMBL541
RTECS number
DG0875000
Beilstein Reference
636131
2.2.3 From bromobenzene 2.2.4 From benzyl
2.2.6 Historical preparation 3 Uses 3.1 Precursor to plasticizers
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plasticizers 3.2 Precursor to sodium benzoate and related preservatives 3.3 Medicinal
Gmelin Reference
2946
3DMet
B00053
Jmol3D images
Image 1 (http://chemapps.stolaf.edu/jmol/jmol.php? model=O%3DC%28O%29c1ccccc1) Image 2 (http://chemapps.stolaf.edu/jmol/jmol.php? model=c1ccc%28cc1%29C%28%3DO%29O)
3.4 Benzoyl chloride 3.5 Niche and
SMILES
laboratory uses
InChI
4 Biology and health effects
Properties
5 Reactions 5.1 Aromatic ring
Molecular formula
C7H6O2
5.2 Carboxyl group
Molar mass 122.12 g mol−1
6 References
Appearance Colorless crystalline solid
7 External links
Odor
faint, pleasant odor
Density
1.2659 g/cm3 (15 °C) 1.0749 g/cm3 (130 °C)[1]
History Benzoic acid was discovered in the sixteenth century. The dry distillation of gum benzoin was first described by 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 and Antoine BoutronCharlard, two French chemists, had produced benzaldehyde [10] but they failed in working out a proper interpretation of the structure of amygdalin that would 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 and Friedrich Wöhler, who determined the composition of benzoic acid.[11] These latter also investigated how hippuric acid is related to benzoic acid.
Melting point
122.41 °C (252.34 °F; 395.56 K)[5]
Boiling point 249.2 °C (480.6 °F; 522.3 K)[6] 370 °C (698 °F; 643 K) decomposes[1] Solubility in 1.7 g/L (0 °C) water 2.7 g/L (18 °C) 3.44 g/L (25 °C) 5.51 g/L (40 °C) 21.45 g/L (75 °C) 56.31 g/L (100 °C)[1][2] Solubility
soluble in acetone, benzene, CCl4, CHCl3, alcohol, ethyl ether, hexane, phenyls, liquid ammonia, acetates
Solubility in 30 g/100 g (18 °C) methanol 32.1 g/100 g (13 °C) 71.5 g/100 g (23 °C)[1] Solubility in 25.4 g/100 g (18 °C) ethanol 47.1 g/100 g (15 °C) 52.4 g/100 g (19.2 °C) 55.9 g/100 g (23 °C)[1] Solubility in 54.2 g/100 g (20 °C)[1] acetone Solubility in 4.22 g/100 g (25 °C)[1] olive oil Solubility in 55.3 g/100 g (25 °C)[1]
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In 1875 Salkowski discovered the antifungal abilities of benzoic acid, which was used for a long time in the preservation of benzoatecontaining cloudberry fruits.[12]
1,4Dioxane
It is also one of the chemical compounds found in castoreum. This compound is gathered from the beaver plant food.[13]
Acidity (pKa) 4.202[4]
log P
1.87
Vapor pressure
0.16 Pa (25 °C) 0.19 kPa (100 °C) 22.6 kPa (200 °C)[3]
Refractive index (nD)
1.5397 (20 °C) 1.504 (132 °C)[1]
Viscosity
1.26 mPa (130 °C)
Production Industrial preparations Benzoic acid is produced commercially by partial oxidation of toluene with oxygen. The process is catalyzed by cobalt or manganese naphthenates. The process uses cheap raw materials, and proceeds in high yield.
Structure Crystal structure
Monoclinic
Molecular shape
planar
Dipole moment
1.72 D in Dioxane Thermochemistry
Specific 146.7 J/mol·K[3] heat capacity C Std molar entropy So298
U.S. production capacity is estimated to be 126,000 tonnes 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. 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.[14] The solubility of benzoic acid in over 40 http://en.wikipedia.org/wiki/Benzoic_acid
167.6 J/mol·K[1]
Std enthalpy 385.2 kJ/mol[1] of formation ΔfHo298 Std enthalpy 3228 kJ/mol[3] of combustion ΔcHo298 Hazards MSDS
JT Baker (http://hazard.com/msds/mf/baker/baker/files/b1356.htm)
GHS pictograms GHS signal word
[7]
Danger
GHS hazard H318, H335[7] statements GHS P261, P280, P305+351+338[7] precautionary statements EU Index
Not listed 3/11
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solvents with references to original sources can be found as part of the Open Notebook Science Challenge.[15] By hydrolysis
Benzoic acid Wikipedia, the free encyclopedia
EU classification
Xi
Rphrases
R37, R41
Sphrases
S26, S39
Main hazards Irritant
Like other nitriles and amides, benzonitrile and benzamide can be hydrolyzed to benzoic acid or its conjugate base in acid or basic conditions.
NFPA 704
From benzaldehyde
Autoignition 571 °C (1,060 °F; 844 K)[6] temperature
The baseinduced disproportionation of benzaldehyde, the Cannizzaro reaction, affords equal amounts of benzoate and benzyl alcohol; the latter can be removed by distillation.
LD50
2 Flash point
1
0
121.5 °C (250.7 °F; 394.6 K)[6]
1700 mg/kg (rat, oral) Related compounds
Related carboxylic acids
Hydroxybenzoic acids Aminobenzoic acids, Nitrobenzoic acids, Phenylacetic acid
Related compounds
Benzaldehyde, Benzyl alcohol, Benzoyl chloride, Benzylamine, Benzamide
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
() (what is: / ?) Infobox references
From bromobenzene Bromobenzene can be converted to benzoic acid by "carbonation" 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] From benzyl alcohol http://en.wikipedia.org/wiki/Benzoic_acid
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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 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 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. Foodgrade benzoic acid is now produced synthetically.
Uses Benzoic acid is mainly consumed in the production of phenol by oxidative decarboxylation at 300−400 °C:[19] 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 Benzoate plasticizers, such as the glycol, diethylenegylcol, 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 Benzoic acid and its salts are used as a food preservatives, represented by the Enumbers E210, E211, E212, and E213. Benzoic acid inhibits the growth of mold, yeast[20] 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.[21] 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.[22][23] http://en.wikipedia.org/wiki/Benzoic_acid
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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.[24]
Medicinal 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.[25][26] As the principal component of benzoin resin, 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 was used as an expectorant, analgesic, and antiseptic in the early 20th century.[27]
Benzoyl chloride Benzoic acid is a precursor to benzoyl chloride, C6H5C(O)Cl by treatment with thionyl chloride, phosgene or one of the chlorides of phosphorus. 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 In teaching laboratories, benzoic acid is a common standard for calibrating a bomb calorimeter.[28]
Biology and health effects Benzoic acid is relatively nontoxic. It is excreted as hippuric acid.[29] Benzoic acid is metabolized by butyrateCoA ligase into an intermediate product, benzoylCoA,[30] which is then metabolized by glycine Nacyltransferase into hippuric acid.[31] 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 species (e.g., cranberry, V. vitis macrocarpon; bilberry, V. myrtillus) contain as much as 0.03–0.13% free 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).[32] Gum benzoin contains up to 20% of benzoic acid and 40% benzoic acid esters.[33] Cryptanaerobacter phenolicus is a bacterium species that produces benzoate from phenol via 4 hydroxybenzoate[34] Benzoic acid is present as part of hippuric acid (Nbenzoylglycine) in urine of mammals, especially herbivores (Gr. hippos = horse; ouron = urine). Humans produce about 0.44 g/L hippuric acid per day in their urine, and if the person is exposed to toluene or benzoic acid, it can rise above that level.[35] 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.[32] Cats have a significantly lower tolerance against benzoic acid and its salts than rats and mice. Lethal dose for cats http://en.wikipedia.org/wiki/Benzoic_acid
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can be as low as 300 mg/kg body weight.[36] The oral LD50 for rats is 3040 mg/kg, for mice it is 1940– 2263 mg/kg.[32] In Taipei, Taiwan, a city health survey in 2010 found that 30% of dried and pickled food products had too much benzoic acid, which may affect the liver and kidney,[37] along with more serious issues like excessive cyclamate.
Reactions Reactions of benzoic acid can occur at either the aromatic ring or at the carboxyl group:
Aromatic ring
Electrophilic aromatic substitution reaction will take place mainly in 3position 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.[38] Conversely, if an activating group (electrondonating) 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 All the reactions mentioned for carboxylic acids are also possible for benzoic acid. Benzoic acid esters are the product of the acid catalysed reaction with alcohols. 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 DIBALH, 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 http://en.wikipedia.org/wiki/Benzoic_acid
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hydroxide.
References 1. ^ a b c d e f g h i j k http://chemister.ru/Database/propertiesen.php?dbid=1&id=679 2. ^ Seidell, Atherton; Linke, William F. (1952). [Google Books (http://books.google.com/books? id=k2e5AAAAIAAJ) Solubilities of Inorganic and Organic Compounds]. Van Nostrand. Retrieved 20140529. 3. ^ a b c Benzoic acid (http://webbook.nist.gov/cgi/cbook.cgi?ID=C65850&Mask=FFFF&Units=SI) in Linstrom, P.J.; Mallard, W.G. (eds.) NIST Chemistry WebBook, NIST Standard Reference Database Number 69. National Institute of Standards and Technology, Gaithersburg MD. http://webbook.nist.gov (retrieved 20140523) 4. ^ Harris, Daniel (2010). Quantitative Chemical Analysis (8 ed.). New York: W. H. Freeman and Company. pp. AP12. ISBN 9781429254366. 5. ^ Melting point of benzoic acid (http://lxsrv7.oru.edu/~alang/meltingpoints/meltingpointof.php?csid=238) 6. ^ a b c Record (http://gestisen.itrust.de/nxt/gateway.dll? f=id$t=default.htm$vid=gestiseng:sdbeng$id=022810) in the GESTIS Substance Database from the IFA 7. ^ a b c SigmaAldrich Co., Benzoic acid (http://www.sigmaaldrich.com/catalog/product/aldrich/w213101). Retrieved on 20140523. 8. ^ "Scientists uncover last steps for benzoic acid creation in plants" (http://www.purdue.edu/newsroom/releases/2012/Q3/scientistsuncoverlaststepsforbenzoicacidcreation inplants.html). Purdue Agriculture News. 9. ^ Neumüller OA (1988). Römpps ChemieLexikon (6 ed.). Stuttgart: Frankh'sche Verlagshandlung. ISBN 3 440045161. OCLC 50969944 (https://www.worldcat.org/oclc/50969944). 10. ^ 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, http://en.wikipedia.org/wiki/Benzoic_acid
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11. ^ Liebig J, Wöhler F (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Chemie, 3 (3): 249–282. doi:10.1002/jlac.18320030302 (http://dx.doi.org/10.1002%2Fjlac.18320030302). 12. ^ Salkowski E (1875). Berl Klin Wochenschr 12: 297–298. 13. ^ The Beaver: Its Life and Impact. Dietland MullerSchwarze, 2003, page 43 (book at google books (http://books.google.fr/books?id=HZ5WjXB5Pr8C&lpg=PA39&ots=WYwTmWi yJ&dq=Castoreum%20beekeeping&lr&hl=fr&pg=PA43#v=onepage&q=Castoreum%20beekeeping&f=false)) 14. ^ D. D. Perrin; W. L. F. Armarego (1988). Purification of Laboratory Chemicals (3rd ed.). Pergamon Press. p. 94. ISBN 0080347150. 15. ^ solubility of benzoic acid in organic solvents (http://lxsrv7.oru.edu/~alang/onsc/solubility/allsolvents.php? solute=benzoic+acid) 16. ^ Donald L. Pavia (2004). Introduction to Organic Laboratory Techniques: A Small Scale Approach. Thomson Brooks/Cole. pp. 312–314. ISBN 0534408338. 17. ^ Shirley, D. A. (1954). "The Synthesis of Ketones from Acid Halides and Organometallic Compounds of Magnesium, Zinc, and Cium". Org. React. 8: 28–58. 18. ^ 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 πBonds, Part 1 (http://dx.doi.org/10.1016/B9780080523491.000020). Elsevier Science. pp. 49–75. ISBN 9780080523491. 19. ^ Maki, Takao; Takeda, Kazuo (2000). "Ullmann's Encyclopedia of Industrial Chemistry". doi:10.1002/14356007.a03_555 (http://dx.doi.org/10.1002%2F14356007.a03_555). ISBN 3527306730. |chapter= ignored (help).
20. ^ 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" (http://aem.asm.org/cgi/content/abstract/57/12/3410). Appl Environ Microbiol. 1991 December 57 (12): 3410– 4. PMC 183988 (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC183988). PMID 1785916 (https://www.ncbi.nlm.nih.gov/pubmed/1785916). 21. ^ Pastrorova I, de Koster CG, Boom JJ (1997). "Analytic Study of Free and Ester Bound Benzoic and Cinnamic Acids of Gum Benzoin Resins by GCMS HPLCfrit FABMS". Phytochem Anal 8 (2): 63–73. doi:10.1002/(SICI)10991565(199703)8:2<63::AIDPCA337>3.0.CO;2Y (http://dx.doi.org/10.1002%2F%28SICI%2910991565%28199703%298%3A2%3C63%3A%3AAID PCA337%3E3.0.CO%3B2Y). 22. ^ GSFA Online Food Additive Group Details: Benzoates (2006) (http://www.codexalimentarius.net/gsfaonline/groups/details.html?id=162) 23. ^ EUROPEAN PARLIAMENT AND COUNCIL DIRECTIVE No 95/2/EC of 20 February 1995 on food additives other than colours and sweeteners (Conslegversions do not contain the latest changes in a law) (http://europa.eu.int/eurlex/en/consleg/pdf/1995/en_1995L0002_do_001.pdf) 24. ^ BfR article Indications of the possible formation of benzene from benzoic acid in foods (http://www.bfr.bund.de/cm/245/indications_of_the_possible_formation_of_benzene_from_benzoic_acid_in_f oods.pdf), BfR Expert Opinion No. 013/2006, 1 December 2005 25. ^ "Whitfield Ointment" (http://www.medipharmalimited.com/whitfield_ointment.asp). 26. ^ 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 0781734819.
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27. ^ Lillard, Benjamin (1919). "Practical druggist and pharmaceutical review of reviews" (http://books.google.com/? id=cs3mAAAAMAAJ&pg=PA25&lpg=PA25&dq=beef+extract+analgesic#v=onepage&q=beef%20extract%20 analgesic&f=false). 28. ^ Experiment 2: Using Bomb Calorimetry to Determine the Resonance Energy of Benzene (http://www.uwlax.edu/faculty/loh/pdf_files/chm313_pdf/Manual_current/chm313_Expt2_bomb.pdf) 29. ^ Cosmetic Ingredient Review Expert Bindu Nair (2001). "Final Report on the Safety Assessment of Benzyl Alcohol, Benzoic Acid, and Sodium Benzoate". Int J Tox 20 (Suppl. 3): 23–50. doi:10.1080/10915810152630729 (http://dx.doi.org/10.1080%2F10915810152630729). PMID 11766131 (https://www.ncbi.nlm.nih.gov/pubmed/11766131). 30. ^ "butyrateCoA ligase" (http://www.brendaenzymes.org/php/result_flat.php4? ecno=6.2.1.2&Suchword=&organism%5B%5D=Homo+sapiens&show_tm=0). BRENDA. Technische Universität Braunschweig. Retrieved 7 May 2014. |chapter= ignored (help) 31. ^ "glycine Nacyltransferase" (http://www.brendaenzymes.info/php/result_flat.php4? ecno=2.3.1.13&Suchword=&organism%5B%5D=Homo+sapiens&show_tm=0). BRENDA. Technische Universität Braunschweig. Retrieved 7 May 2014. |chapter= ignored (help) 32. ^ a b c "Concise International Chemical Assessment Document 26: BENZOIC ACID AND SODIUM BENZOATE" (http://www.inchem.org/documents/cicads/cicads/cicad26.htm). 33. ^ Tomokuni K, Ogata M (1972). "Direct Colorimetric Determination of Hippuric Acid in Urine". Clin Chem 18 (4): 349–351. PMID 5012256 (https://www.ncbi.nlm.nih.gov/pubmed/5012256). 34. ^ Juteau, Pierre; Valérie Côté, Marie Duckett, Réjean Beaudet, François Lépine, Richard Villemur and JeanGuy Bisaillon (January 2005). "Cryptanaerobacter phenolicus gen. nov., sp. nov., an anaerobe that transforms phenol into benzoate via 4hydroxybenzoate" (http://ijs.sgmjournals.org/content/55/1/245.abstract? relatedurls=yes&legid=ijs;55/1/245). IJSEM 55 (1): 245–250. doi:10.1099/ijs.0.029140 (http://dx.doi.org/10.1099%2Fijs.0.029140). PMID 15653882 (https://www.ncbi.nlm.nih.gov/pubmed/15653882). 35. ^ Krebs HA, Wiggins D, Stubbs M (1983). "Studies on the mechanism of the antifungal action of benzoate" (http://www.biochemj.org/bj/214/0657/2140657.pdf). Biochem J 214 (3): 657–663. PMC 1152300 (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1152300). PMID 6226283 (https://www.ncbi.nlm.nih.gov/pubmed/6226283). 36. ^ 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 (http://dx.doi.org/10.1136%2Fvr.90.3.53). PMID 4672555 (https://www.ncbi.nlm.nih.gov/pubmed/4672555). 37. ^ Chen, Jian; Y.L. Kao (18 January 2010). "Nearly 30% dried, pickled foods fail safety inspections" (http://www.chinapost.com.tw/taiwan/national/nationalnews/2010/01/18/241326/Nearly30.htm). The China Post. 38. ^ Brewster, R. Q.; Williams, B.; Phillips, R. (1955), "3,5Dinitrobenzoic Acid" (http://www.orgsyn.org/demo.aspx?prep=cv3p0337), Org. Synth.; Coll. Vol. 3: 337
External links International Chemical Safety Card 0103
http://en.wikipedia.org/wiki/Benzoic_acid
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(http://www.inchem.org/documents/icsc/icsc/eics0103.htm) SIDS Initial Assessment Report for Benzoic Acid (http://www.inchem.org/documents/sids/sids/BENZOATES.pdf) from the Organisation for Economic Cooperation and Development (OECD) ChemicalLand (http://www.chemicalland21.com/arokorhi/industrialchem/organic/BENZOIC%20ACID.htm) Retrieved from "http://en.wikipedia.org/w/index.php?title=Benzoic_acid&oldid=636779195" Categories: Benzoic acids Excipients This page was last modified on 5 December 2014 at 17:31. Text is available under the Creative Commons AttributionShareAlike License; additional may apply. By using this site, you agree to the of Use and Privacy Policy. Wikipedia® is a ed trademark of the Wikimedia Foundation, Inc., a nonprofit organization.
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Benzoic acid From Wikipedia, the free encyclopedia
Benzoic acid /bɛnˈzoʊ.ɪk/, C7H6O2 (or
Benzoic acid
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 occurs naturally in many plants[8] and it 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/.
Benzoic acid crystals
Contents
IUPAC name Benzoic acid
1 History
Other names
2 Production 2.1 Industrial preparations
Carboxybenzene; E210; Dracylic acid; Phenylmethanoic acid; Benzenecarboxylic acid
2.2 Laboratory synthesis
Identifiers
2.2.1 By
CAS number 65850
hydrolysis
PubChem
2.2.2 From benzaldehyde
243
ChemSpider 238 UNII
8SKN0B0MIM
EC number
2006182
DrugBank
DB03793
alcohol
KEGG
D00038
2.2.5 From benzyl
MeSH
benzoic+acid
chloride
ChEBI
CHEBI:30746
ChEMBL
CHEMBL541
RTECS number
DG0875000
Beilstein Reference
636131
2.2.3 From bromobenzene 2.2.4 From benzyl
2.2.6 Historical preparation 3 Uses 3.1 Precursor to plasticizers
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plasticizers 3.2 Precursor to sodium benzoate and related preservatives 3.3 Medicinal
Gmelin Reference
2946
3DMet
B00053
Jmol3D images
Image 1 (http://chemapps.stolaf.edu/jmol/jmol.php? model=O%3DC%28O%29c1ccccc1) Image 2 (http://chemapps.stolaf.edu/jmol/jmol.php? model=c1ccc%28cc1%29C%28%3DO%29O)
3.4 Benzoyl chloride 3.5 Niche and
SMILES
laboratory uses
InChI
4 Biology and health effects
Properties
5 Reactions 5.1 Aromatic ring
Molecular formula
C7H6O2
5.2 Carboxyl group
Molar mass 122.12 g mol−1
6 References
Appearance Colorless crystalline solid
7 External links
Odor
faint, pleasant odor
Density
1.2659 g/cm3 (15 °C) 1.0749 g/cm3 (130 °C)[1]
History Benzoic acid was discovered in the sixteenth century. The dry distillation of gum benzoin was first described by 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 and Antoine BoutronCharlard, two French chemists, had produced benzaldehyde [10] but they failed in working out a proper interpretation of the structure of amygdalin that would 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 and Friedrich Wöhler, who determined the composition of benzoic acid.[11] These latter also investigated how hippuric acid is related to benzoic acid.
Melting point
122.41 °C (252.34 °F; 395.56 K)[5]
Boiling point 249.2 °C (480.6 °F; 522.3 K)[6] 370 °C (698 °F; 643 K) decomposes[1] Solubility in 1.7 g/L (0 °C) water 2.7 g/L (18 °C) 3.44 g/L (25 °C) 5.51 g/L (40 °C) 21.45 g/L (75 °C) 56.31 g/L (100 °C)[1][2] Solubility
soluble in acetone, benzene, CCl4, CHCl3, alcohol, ethyl ether, hexane, phenyls, liquid ammonia, acetates
Solubility in 30 g/100 g (18 °C) methanol 32.1 g/100 g (13 °C) 71.5 g/100 g (23 °C)[1] Solubility in 25.4 g/100 g (18 °C) ethanol 47.1 g/100 g (15 °C) 52.4 g/100 g (19.2 °C) 55.9 g/100 g (23 °C)[1] Solubility in 54.2 g/100 g (20 °C)[1] acetone Solubility in 4.22 g/100 g (25 °C)[1] olive oil Solubility in 55.3 g/100 g (25 °C)[1]
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In 1875 Salkowski discovered the antifungal abilities of benzoic acid, which was used for a long time in the preservation of benzoatecontaining cloudberry fruits.[12]
1,4Dioxane
It is also one of the chemical compounds found in castoreum. This compound is gathered from the beaver plant food.[13]
Acidity (pKa) 4.202[4]
log P
1.87
Vapor pressure
0.16 Pa (25 °C) 0.19 kPa (100 °C) 22.6 kPa (200 °C)[3]
Refractive index (nD)
1.5397 (20 °C) 1.504 (132 °C)[1]
Viscosity
1.26 mPa (130 °C)
Production Industrial preparations Benzoic acid is produced commercially by partial oxidation of toluene with oxygen. The process is catalyzed by cobalt or manganese naphthenates. The process uses cheap raw materials, and proceeds in high yield.
Structure Crystal structure
Monoclinic
Molecular shape
planar
Dipole moment
1.72 D in Dioxane Thermochemistry
Specific 146.7 J/mol·K[3] heat capacity C Std molar entropy So298
U.S. production capacity is estimated to be 126,000 tonnes 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. 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.[14] The solubility of benzoic acid in over 40 http://en.wikipedia.org/wiki/Benzoic_acid
167.6 J/mol·K[1]
Std enthalpy 385.2 kJ/mol[1] of formation ΔfHo298 Std enthalpy 3228 kJ/mol[3] of combustion ΔcHo298 Hazards MSDS
JT Baker (http://hazard.com/msds/mf/baker/baker/files/b1356.htm)
GHS pictograms GHS signal word
[7]
Danger
GHS hazard H318, H335[7] statements GHS P261, P280, P305+351+338[7] precautionary statements EU Index
Not listed 3/11
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solvents with references to original sources can be found as part of the Open Notebook Science Challenge.[15] By hydrolysis
Benzoic acid Wikipedia, the free encyclopedia
EU classification
Xi
Rphrases
R37, R41
Sphrases
S26, S39
Main hazards Irritant
Like other nitriles and amides, benzonitrile and benzamide can be hydrolyzed to benzoic acid or its conjugate base in acid or basic conditions.
NFPA 704
From benzaldehyde
Autoignition 571 °C (1,060 °F; 844 K)[6] temperature
The baseinduced disproportionation of benzaldehyde, the Cannizzaro reaction, affords equal amounts of benzoate and benzyl alcohol; the latter can be removed by distillation.
LD50
2 Flash point
1
0
121.5 °C (250.7 °F; 394.6 K)[6]
1700 mg/kg (rat, oral) Related compounds
Related carboxylic acids
Hydroxybenzoic acids Aminobenzoic acids, Nitrobenzoic acids, Phenylacetic acid
Related compounds
Benzaldehyde, Benzyl alcohol, Benzoyl chloride, Benzylamine, Benzamide
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
() (what is: / ?) Infobox references
From bromobenzene Bromobenzene can be converted to benzoic acid by "carbonation" 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] From benzyl alcohol http://en.wikipedia.org/wiki/Benzoic_acid
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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 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 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. Foodgrade benzoic acid is now produced synthetically.
Uses Benzoic acid is mainly consumed in the production of phenol by oxidative decarboxylation at 300−400 °C:[19] 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 Benzoate plasticizers, such as the glycol, diethylenegylcol, 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 Benzoic acid and its salts are used as a food preservatives, represented by the Enumbers E210, E211, E212, and E213. Benzoic acid inhibits the growth of mold, yeast[20] 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.[21] 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.[22][23] http://en.wikipedia.org/wiki/Benzoic_acid
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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.[24]
Medicinal 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.[25][26] As the principal component of benzoin resin, 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 was used as an expectorant, analgesic, and antiseptic in the early 20th century.[27]
Benzoyl chloride Benzoic acid is a precursor to benzoyl chloride, C6H5C(O)Cl by treatment with thionyl chloride, phosgene or one of the chlorides of phosphorus. 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 In teaching laboratories, benzoic acid is a common standard for calibrating a bomb calorimeter.[28]
Biology and health effects Benzoic acid is relatively nontoxic. It is excreted as hippuric acid.[29] Benzoic acid is metabolized by butyrateCoA ligase into an intermediate product, benzoylCoA,[30] which is then metabolized by glycine Nacyltransferase into hippuric acid.[31] 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 species (e.g., cranberry, V. vitis macrocarpon; bilberry, V. myrtillus) contain as much as 0.03–0.13% free 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).[32] Gum benzoin contains up to 20% of benzoic acid and 40% benzoic acid esters.[33] Cryptanaerobacter phenolicus is a bacterium species that produces benzoate from phenol via 4 hydroxybenzoate[34] Benzoic acid is present as part of hippuric acid (Nbenzoylglycine) in urine of mammals, especially herbivores (Gr. hippos = horse; ouron = urine). Humans produce about 0.44 g/L hippuric acid per day in their urine, and if the person is exposed to toluene or benzoic acid, it can rise above that level.[35] 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.[32] Cats have a significantly lower tolerance against benzoic acid and its salts than rats and mice. Lethal dose for cats http://en.wikipedia.org/wiki/Benzoic_acid
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can be as low as 300 mg/kg body weight.[36] The oral LD50 for rats is 3040 mg/kg, for mice it is 1940– 2263 mg/kg.[32] In Taipei, Taiwan, a city health survey in 2010 found that 30% of dried and pickled food products had too much benzoic acid, which may affect the liver and kidney,[37] along with more serious issues like excessive cyclamate.
Reactions Reactions of benzoic acid can occur at either the aromatic ring or at the carboxyl group:
Aromatic ring
Electrophilic aromatic substitution reaction will take place mainly in 3position 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.[38] Conversely, if an activating group (electrondonating) 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 All the reactions mentioned for carboxylic acids are also possible for benzoic acid. Benzoic acid esters are the product of the acid catalysed reaction with alcohols. 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 DIBALH, 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 http://en.wikipedia.org/wiki/Benzoic_acid
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hydroxide.
References 1. ^ a b c d e f g h i j k http://chemister.ru/Database/propertiesen.php?dbid=1&id=679 2. ^ Seidell, Atherton; Linke, William F. (1952). [Google Books (http://books.google.com/books? id=k2e5AAAAIAAJ) Solubilities of Inorganic and Organic Compounds]. Van Nostrand. Retrieved 20140529. 3. ^ a b c Benzoic acid (http://webbook.nist.gov/cgi/cbook.cgi?ID=C65850&Mask=FFFF&Units=SI) in Linstrom, P.J.; Mallard, W.G. (eds.) NIST Chemistry WebBook, NIST Standard Reference Database Number 69. National Institute of Standards and Technology, Gaithersburg MD. http://webbook.nist.gov (retrieved 20140523) 4. ^ Harris, Daniel (2010). Quantitative Chemical Analysis (8 ed.). New York: W. H. Freeman and Company. pp. AP12. ISBN 9781429254366. 5. ^ Melting point of benzoic acid (http://lxsrv7.oru.edu/~alang/meltingpoints/meltingpointof.php?csid=238) 6. ^ a b c Record (http://gestisen.itrust.de/nxt/gateway.dll? f=id$t=default.htm$vid=gestiseng:sdbeng$id=022810) in the GESTIS Substance Database from the IFA 7. ^ a b c SigmaAldrich Co., Benzoic acid (http://www.sigmaaldrich.com/catalog/product/aldrich/w213101). Retrieved on 20140523. 8. ^ "Scientists uncover last steps for benzoic acid creation in plants" (http://www.purdue.edu/newsroom/releases/2012/Q3/scientistsuncoverlaststepsforbenzoicacidcreation inplants.html). Purdue Agriculture News. 9. ^ Neumüller OA (1988). Römpps ChemieLexikon (6 ed.). Stuttgart: Frankh'sche Verlagshandlung. ISBN 3 440045161. OCLC 50969944 (https://www.worldcat.org/oclc/50969944). 10. ^ 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, http://en.wikipedia.org/wiki/Benzoic_acid
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11. ^ Liebig J, Wöhler F (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Chemie, 3 (3): 249–282. doi:10.1002/jlac.18320030302 (http://dx.doi.org/10.1002%2Fjlac.18320030302). 12. ^ Salkowski E (1875). Berl Klin Wochenschr 12: 297–298. 13. ^ The Beaver: Its Life and Impact. Dietland MullerSchwarze, 2003, page 43 (book at google books (http://books.google.fr/books?id=HZ5WjXB5Pr8C&lpg=PA39&ots=WYwTmWi yJ&dq=Castoreum%20beekeeping&lr&hl=fr&pg=PA43#v=onepage&q=Castoreum%20beekeeping&f=false)) 14. ^ D. D. Perrin; W. L. F. Armarego (1988). Purification of Laboratory Chemicals (3rd ed.). Pergamon Press. p. 94. ISBN 0080347150. 15. ^ solubility of benzoic acid in organic solvents (http://lxsrv7.oru.edu/~alang/onsc/solubility/allsolvents.php? solute=benzoic+acid) 16. ^ Donald L. Pavia (2004). Introduction to Organic Laboratory Techniques: A Small Scale Approach. Thomson Brooks/Cole. pp. 312–314. ISBN 0534408338. 17. ^ Shirley, D. A. (1954). "The Synthesis of Ketones from Acid Halides and Organometallic Compounds of Magnesium, Zinc, and Cium". Org. React. 8: 28–58. 18. ^ 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 πBonds, Part 1 (http://dx.doi.org/10.1016/B9780080523491.000020). Elsevier Science. pp. 49–75. ISBN 9780080523491. 19. ^ Maki, Takao; Takeda, Kazuo (2000). "Ullmann's Encyclopedia of Industrial Chemistry". doi:10.1002/14356007.a03_555 (http://dx.doi.org/10.1002%2F14356007.a03_555). ISBN 3527306730. |chapter= ignored (help).
20. ^ 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" (http://aem.asm.org/cgi/content/abstract/57/12/3410). Appl Environ Microbiol. 1991 December 57 (12): 3410– 4. PMC 183988 (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC183988). PMID 1785916 (https://www.ncbi.nlm.nih.gov/pubmed/1785916). 21. ^ Pastrorova I, de Koster CG, Boom JJ (1997). "Analytic Study of Free and Ester Bound Benzoic and Cinnamic Acids of Gum Benzoin Resins by GCMS HPLCfrit FABMS". Phytochem Anal 8 (2): 63–73. doi:10.1002/(SICI)10991565(199703)8:2<63::AIDPCA337>3.0.CO;2Y (http://dx.doi.org/10.1002%2F%28SICI%2910991565%28199703%298%3A2%3C63%3A%3AAID PCA337%3E3.0.CO%3B2Y). 22. ^ GSFA Online Food Additive Group Details: Benzoates (2006) (http://www.codexalimentarius.net/gsfaonline/groups/details.html?id=162) 23. ^ EUROPEAN PARLIAMENT AND COUNCIL DIRECTIVE No 95/2/EC of 20 February 1995 on food additives other than colours and sweeteners (Conslegversions do not contain the latest changes in a law) (http://europa.eu.int/eurlex/en/consleg/pdf/1995/en_1995L0002_do_001.pdf) 24. ^ BfR article Indications of the possible formation of benzene from benzoic acid in foods (http://www.bfr.bund.de/cm/245/indications_of_the_possible_formation_of_benzene_from_benzoic_acid_in_f oods.pdf), BfR Expert Opinion No. 013/2006, 1 December 2005 25. ^ "Whitfield Ointment" (http://www.medipharmalimited.com/whitfield_ointment.asp). 26. ^ 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 0781734819.
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27. ^ Lillard, Benjamin (1919). "Practical druggist and pharmaceutical review of reviews" (http://books.google.com/? id=cs3mAAAAMAAJ&pg=PA25&lpg=PA25&dq=beef+extract+analgesic#v=onepage&q=beef%20extract%20 analgesic&f=false). 28. ^ Experiment 2: Using Bomb Calorimetry to Determine the Resonance Energy of Benzene (http://www.uwlax.edu/faculty/loh/pdf_files/chm313_pdf/Manual_current/chm313_Expt2_bomb.pdf) 29. ^ Cosmetic Ingredient Review Expert Bindu Nair (2001). "Final Report on the Safety Assessment of Benzyl Alcohol, Benzoic Acid, and Sodium Benzoate". Int J Tox 20 (Suppl. 3): 23–50. doi:10.1080/10915810152630729 (http://dx.doi.org/10.1080%2F10915810152630729). PMID 11766131 (https://www.ncbi.nlm.nih.gov/pubmed/11766131). 30. ^ "butyrateCoA ligase" (http://www.brendaenzymes.org/php/result_flat.php4? ecno=6.2.1.2&Suchword=&organism%5B%5D=Homo+sapiens&show_tm=0). BRENDA. Technische Universität Braunschweig. Retrieved 7 May 2014. |chapter= ignored (help) 31. ^ "glycine Nacyltransferase" (http://www.brendaenzymes.info/php/result_flat.php4? ecno=2.3.1.13&Suchword=&organism%5B%5D=Homo+sapiens&show_tm=0). BRENDA. Technische Universität Braunschweig. Retrieved 7 May 2014. |chapter= ignored (help) 32. ^ a b c "Concise International Chemical Assessment Document 26: BENZOIC ACID AND SODIUM BENZOATE" (http://www.inchem.org/documents/cicads/cicads/cicad26.htm). 33. ^ Tomokuni K, Ogata M (1972). "Direct Colorimetric Determination of Hippuric Acid in Urine". Clin Chem 18 (4): 349–351. PMID 5012256 (https://www.ncbi.nlm.nih.gov/pubmed/5012256). 34. ^ Juteau, Pierre; Valérie Côté, Marie Duckett, Réjean Beaudet, François Lépine, Richard Villemur and JeanGuy Bisaillon (January 2005). "Cryptanaerobacter phenolicus gen. nov., sp. nov., an anaerobe that transforms phenol into benzoate via 4hydroxybenzoate" (http://ijs.sgmjournals.org/content/55/1/245.abstract? relatedurls=yes&legid=ijs;55/1/245). IJSEM 55 (1): 245–250. doi:10.1099/ijs.0.029140 (http://dx.doi.org/10.1099%2Fijs.0.029140). PMID 15653882 (https://www.ncbi.nlm.nih.gov/pubmed/15653882). 35. ^ Krebs HA, Wiggins D, Stubbs M (1983). "Studies on the mechanism of the antifungal action of benzoate" (http://www.biochemj.org/bj/214/0657/2140657.pdf). Biochem J 214 (3): 657–663. PMC 1152300 (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1152300). PMID 6226283 (https://www.ncbi.nlm.nih.gov/pubmed/6226283). 36. ^ 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 (http://dx.doi.org/10.1136%2Fvr.90.3.53). PMID 4672555 (https://www.ncbi.nlm.nih.gov/pubmed/4672555). 37. ^ Chen, Jian; Y.L. Kao (18 January 2010). "Nearly 30% dried, pickled foods fail safety inspections" (http://www.chinapost.com.tw/taiwan/national/nationalnews/2010/01/18/241326/Nearly30.htm). The China Post. 38. ^ Brewster, R. Q.; Williams, B.; Phillips, R. (1955), "3,5Dinitrobenzoic Acid" (http://www.orgsyn.org/demo.aspx?prep=cv3p0337), Org. Synth.; Coll. Vol. 3: 337
External links International Chemical Safety Card 0103
http://en.wikipedia.org/wiki/Benzoic_acid
Wikimedia Commons has media related to Benzoic acid. 10/11
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(http://www.inchem.org/documents/icsc/icsc/eics0103.htm) SIDS Initial Assessment Report for Benzoic Acid (http://www.inchem.org/documents/sids/sids/BENZOATES.pdf) from the Organisation for Economic Cooperation and Development (OECD) ChemicalLand (http://www.chemicalland21.com/arokorhi/industrialchem/organic/BENZOIC%20ACID.htm) Retrieved from "http://en.wikipedia.org/w/index.php?title=Benzoic_acid&oldid=636779195" Categories: Benzoic acids Excipients This page was last modified on 5 December 2014 at 17:31. Text is available under the Creative Commons AttributionShareAlike License; additional may apply. By using this site, you agree to the of Use and Privacy Policy. Wikipedia® is a ed trademark of the Wikimedia Foundation, Inc., a nonprofit organization.
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