Rf Value Of Benzoic Acid

Organic chemical compound (C6H5COOH)

Benzoic acrid

Names
Preferred IUPAC proper noun Benzoic acrid[ane]
Systematic IUPAC proper name Benzenecarboxylic acrid
Other names Carboxybenzene E210 Dracylic acid Phenylmethanoic acid BzOH
Identifiers
CAS Number	65-85-0 Y
3D model (JSmol)	Interactive image
3DMet	B00053
Beilstein Reference	636131
ChEBI	CHEBI:30746 Y
ChEMBL	ChEMBL541 Y
ChemSpider	238 Y
DrugBank	DB03793 Y
ECHA InfoCard	100.000.562
EC Number	200-618-2
E number	E210 (preservatives)
Gmelin Reference	2946
KEGG	D00038 Y
MeSH	benzoic+acid
PubChem CID	243
RTECS number	DG0875000
UNII	8SKN0B0MIM Y
CompTox Dashboard (EPA)	DTXSID6020143
InChI InChI=1S/C7H6O2/c8-7(9)6-4-two-one-3-5-6/h1-5H,(H,viii,ix) Y Key: WPYMKLBDIGXBTP-UHFFFAOYSA-N Y InChI=1/C7H6O2/c8-7(9)half dozen-4-two-1-3-five-6/h1-5H,(H,8,9) Cardinal: WPYMKLBDIGXBTP-UHFFFAOYAD
SMILES O=C(O)c1ccccc1
Backdrop
Chemical formula	C 7 H 6 O 2
Molar mass	122.123 g/mol
Advent	Colorless crystalline solid
Odor	Faint, pleasant odour
Density	1.2659g/cm3 (fifteen °C) 1.0749k/cm3 (130 °C)[2]
Melting point	122 °C (252 °F; 395 1000)[7]
Boiling betoken	250 °C (482 °F; 523 Grand)[7]
Solubility in water	1.7g/L (0 °C) two.viiyard/L (18 °C) three.44m/L (25 °C) 5.51one thousand/L (40 °C) 21.45g/L (75 °C) 56.31g/Fifty (100 °C)[2] [3]
Solubility	Soluble in acetone, benzene, CCliv, CHCliii, booze, ethyl ether, hexane, phenyls, liquid ammonia, acetates
Solubility in methanol	30g/100 chiliad (−18 °C) 32.1m/100 g (−13 °C) 71.5k/100 g (23 °C)[2]
Solubility in ethanol	25.4g/100 g (−18 °C) 47.1k/100 g (15 °C) 52.ivg/100 one thousand (19.2 °C) 55.9thousand/100 g (23 °C)[ii]
Solubility in acetone	54.twog/100 one thousand (20 °C)[2]
Solubility in olive oil	four.22g/100 grand (25 °C)[2]
Solubility in 1,4-Dioxane	55.3m/100 one thousand (25 °C)[two]
log P	one.87
Vapor pressure	0.16Pa (25 °C) 0.19kPa (100 °C) 22.6kPa (200 °C)[four]
Acerbity (pK a)	4.202 (HtwoO)[5] xi.02 (DMSO)[6]
Magnetic susceptibility (χ)	−seventy.28·x−6 cm3/mol
Refractive index (n D)	ane.5397 (twenty °C) 1.504 (132 °C)[ii]
Viscosity	1.26mPa (130 °C)
Structure
Crystal structure	Monoclinic
Molecular shape	Planar
Dipole moment	1.72D in dioxane
Thermochemistry
Heat capacity (C)	146.sevenJ/mol·K[iv]
Std molar entropy (S ⦵ 298)	167.viJ/mol·M[2]
Std enthalpy of formation (Δf H ⦵ 298)	−385.twokJ/mol[2]
Std enthalpy of combustion (Δc H ⦵ 298)	−3228kJ/mol[iv]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Irritant
GHS labelling:
Pictograms	[8]
Signal word	Danger
Adventure statements	H318, H335 [8]
Precautionary statements	P261, P280, P305+P351+P338 [8]
NFPA 704 (burn diamond)	2 1 0
Wink bespeak	121.v °C (250.vii °F; 394.6 K)[vii]
Autoignition temperature	571 °C (one,060 °F; 844 1000)[7]
Lethal dose or concentration (LD, LC):
LD50 (median dose)	1700mg/kg (rat, oral)
Safety information canvas (SDS)	JT Bakery
Related compounds
Related carboxylic acids	Hydroxybenzoic acids Aminobenzoic acids, Nitrobenzoic acids, Phenylacetic acrid
Related compounds	Benzaldehyde, Benzyl alcohol, Benzoyl chloride, Benzylamine, Benzamide
Except where otherwise noted, data are given for materials in their standard land (at 25 °C [77 °F], 100 kPa). Yverify (what is Y N  ?) Infobox references

Chemic compound

Benzoic acid is a white (or colorless) solid organic compound with the formula C₆H₅COOH, whose structure consists of a benzene ring (C₆H_{half dozen} ) with a carboxyl (−C(=O)OH) substituent. It is the simplest effluvious carboxylic acid. The proper noun is derived from gum benzoin, which was for a long time its but source.

Benzoic acid occurs naturally in many plants^[nine] and serves every bit an intermediate in the biosynthesis of many secondary metabolites. Salts of benzoic acrid are used as food preservatives. Benzoic acid is an important forerunner for the industrial synthesis of many other organic substances. The salts and esters of benzoic acrid are known as benzoates .

History [edit]

Benzoic acid was discovered in the sixteenth century. The dry distillation of gum benzoin was commencement described past Nostradamus (1556), and so by Alexius Pedemontanus (1560) and Blaise de Vigenère (1596).^[10]

Justus von Liebig and Friedrich Wöhler adamant the limerick of benzoic acid.^[11] These latter as well investigated how hippuric acid is related to benzoic acid.

In 1875 Salkowski discovered the antifungal properties of benzoic acid, which was used for a long time in the preservation of benzoate-containing cloudberry fruits.^{[12] [ disputed – talk over ]}

Production [edit]

Industrial preparations [edit]

Benzoic acid is produced commercially by partial oxidation of toluene with oxygen. The process is catalyzed past cobalt or manganese naphthenates. The procedure uses abundant materials, and gain in high yield.^[13]

The start industrial procedure involved the reaction of benzotrichloride (trichloromethyl benzene) with calcium hydroxide in water, using atomic number 26 or iron salts as catalyst. The resulting calcium benzoate is converted to benzoic acrid with hydrochloric acrid. The product contains significant amounts of chlorinated benzoic acid derivatives. For this reason, benzoic acid for human being consumption was obtained by dry distillation of glue benzoin. Food-form benzoic acid is at present produced synthetically.

Laboratory synthesis [edit]

Benzoic acrid is cheap and readily bachelor, 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 past recrystallization from h2o because of its high solubility in hot h2o and poor solubility in cold water. The avoidance of organic solvents for the recrystallization makes this experiment especially safe. This process usually gives a yield of around 65%.^[fourteen]

Past hydrolysis [edit]

Like other nitriles and amides, benzonitrile and benzamide tin can be hydrolyzed to benzoic acrid or its conjugate base in acrid or basic conditions.

From Grignard reagent [edit]

Bromobenzene tin can be converted to benzoic acid past "carboxylation" of the intermediate phenylmagnesium bromide.^[fifteen] This synthesis offers a convenient exercise for students to carry out a Grignard reaction, an important course of carbon–carbon bail forming reaction in organic chemical science.^{[xvi] [17] [18] [19] [20]}

Oxidation of benzyl compounds [edit]

Benzyl alcohol^{[21] [22]} and benzyl chloride and virtually all benzyl derivatives are readily oxidized to benzoic acrid.

Uses [edit]

Benzoic acid is mainly consumed in the product of phenol by oxidative decarboxylation at 300−400 °C:^[23]

${\displaystyle {\ce {C6H5CO2H + 1/2 O2 -> C6H5OH + CO2}}}$

The temperature required can be lowered to 200 °C by the add-on 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 plasticizers, such as the glycol-, diethyleneglycol-, and triethyleneglycol esters, are obtained past transesterification of methyl benzoate with the corresponding diol.^[23] These plasticizers, which are used similarly to those derived from terephthalic acrid ester, represent alternatives to phthalates.^[23]

Precursor to sodium benzoate and related preservatives [edit]

Benzoic acid and its salts are used as nutrient preservatives, represented by the Due east numbers E210, E211, E212, and E213. Benzoic acid inhibits the growth of mold, yeast^[24] and some bacteria. It is either added straight or created from reactions with its sodium, potassium, or calcium salt. The mechanism starts with the assimilation of benzoic acrid 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 nutrient.^[25] Benzoic acid, benzoates and their derivatives are used as preservatives for acidic foods and beverages such every bit citrus fruit juices (citric acid), sparkling drinks (carbon dioxide), soft drinks (phosphoric acid), pickles (vinegar) and other acidified foods.

Typical concentrations of benzoic acid as a preservative in food are between 0.05 and 0.one%. Foods in which benzoic acid may be used and maximum levels for its application are controlled by local food laws.^{[26] [27]}

Concern has been expressed that benzoic acrid and its salts may react with ascorbic acid (vitamin C) in some soft drinks, forming minor quantities of carcinogenic benzene.^[28]

Medicinal [edit]

Benzoic acid is a constituent of Whitfield's ointment which is used for the handling of fungal skin diseases such as ringworm and athlete's foot.^{[29] [30]} As the primary component of gum benzoin, benzoic acid is likewise 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 acrid was used as an expectorant, analgesic, and clarified in the early 20th century.^[31]

Niche and laboratory uses [edit]

In teaching laboratories, benzoic acid is a mutual standard for calibrating a bomb calorimeter.^[32]

Biology and health effects [edit]

Benzoic acid occurs naturally every bit do its esters in many plant and animal species. Appreciable amounts are found in most berries (effectually 0.05%). Ripe fruits of several Vaccinium species (due east.g., cranberry, 5. vitis macrocarpon; bilberry, V. myrtillus) comprise as much as 0.03–0.13% free benzoic acid. Benzoic acid is also formed in apples subsequently 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).^[33] Gum benzoin contains up to xx% of benzoic acid and 40% benzoic acid esters.^[34]

In terms of its biosynthesis, benzoate is produced in plants from cinnamic acid.^[35] A pathway has been identified from phenol via four-hydroxybenzoate.^[36]

Reactions [edit]

Reactions of benzoic acid can occur at either the aromatic band or at the carboxyl group.

Aromatic ring [edit]

Electrophilic aromatic substitution reaction will take place mainly in iii-position due to the electron-withdrawing carboxylic group; i.east. benzoic acid is meta directing.^[37]

Carboxyl group [edit]

Reactions typical for carboxylic acids apply also to benzoic acrid.^[23]

• Benzoate esters are the product of the acid catalysed reaction with alcohols.
• Benzoic acid amides are usually prepared from benzoyl chloride.
• Dehydration to benzoic anhydride is induced with 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 nether acidic water costless conditions with benzonitrile.
• Reduction to benzaldehyde and benzyl booze is possible using DIBAL-H, LiAlH₄ or sodium borohydride.
• Decarboxylation to benzene may exist effected by heating in quinoline in the presence of copper salts. Hunsdiecker decarboxylation can be achieved by heating the silver salt.

Safety and mammalian metabolism [edit]

It is excreted every bit hippuric acid.^[38] Benzoic acrid is metabolized by butyrate-CoA ligase into an intermediate production, benzoyl-CoA,^[39] which is then metabolized by glycine N-acyltransferase into hippuric acid.^[40] Humans metabolize toluene which is too excreted equally hippuric acid.^[41]

For humans, the World Health Organization'due south International Programme on Chemical Safety (IPCS) suggests a provisional tolerable intake would be 5 mg/kg torso weight per mean solar day.^[33] Cats have a significantly lower tolerance against benzoic acrid and its salts than rats and mice. Lethal dose for cats tin be as low as 300 mg/kg trunk weight.^[42] The oral LD₅₀ for rats is 3040 mg/kg, for mice it is 1940–2263 mg/kg.^[33]

In Taipei, Taiwan, a city health survey in 2010 found that 30% of stale and pickled food products had benzoic acid.^[43]

References [edit]

1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Bluish Book). Cambridge: The Royal Club of Chemistry. 2014. p. 745. doi:x.1039/9781849733069-00648. ISBN978-0-85404-182-4.
2. ^ ^{a b c d e f g h i j} "benzoic acid". chemister.ru . Retrieved 24 October 2018.
3. ^ Seidell, Atherton; Linke, William F. (1952). Solubilities of Inorganic and Organic Compounds. Van Nostrand.
4. ^ ^{a b c} Benzoic acrid in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemical science WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-05-23)
5. ^ Harris, Daniel (2010). Quantitative Chemic Analysis (eight ed.). New York: W. H. Freeman and Company. pp. AP12. ISBN9781429254366.
6. ^ Olmstead, William N.; Bordwell, Frederick Thousand. (1980). "Ion-pair association constants in dimethyl sulfoxide". The Journal of Organic Chemistry. 45 (16): 3299–3305. doi:10.1021/jo01304a033.
7. ^ ^{a b c d} Record in the GESTIS Substance Database of the Plant for Occupational Safety and Health
8. ^ ^{a b c} Sigma-Aldrich Co., Benzoic acid. Retrieved on 2014-05-23.
9. ^ "Scientists uncover concluding steps for benzoic acid creation in plants". Purdue Agriculture News.
10. ^ Neumüller O-A (1988). Römpps Chemie-Lexikon (vi ed.). Stuttgart: Frankh'sche Verlagshandlung. ISBN978-3-440-04516-9. OCLC 50969944.
11. ^ Liebig J; Wöhler F (1832). "Untersuchungen über das Radikal der Benzoesäure". Annalen der Chemie. three (three): 249–282. doi:10.1002/jlac.18320030302. hdl:2027/hvd.hxdg3f.
12. ^ Salkowski E (1875). Berl Klin Wochenschr. 12: 297–298.
13. ^ Wade, Leroy 1000. (2014). Organic Chemistry (Pearson new international ed.). Harlow: Pearson Pedagogy Express. p. 985. ISBN978-1-292-02165-2.
14. ^ D. D. Perrin; W. Fifty. F. Armarego (1988). Purification of Laboratory Chemicals (3rd ed.). Pergamon Press. pp. 94. ISBN978-0-08-034715-8.
15. ^ Donald L. Pavia (2004). Introduction to Organic Laboratory technique: A Small Scale Approach. Thomson Brooks/Cole. pp. 312–314. ISBN978-0-534-40833-6.
16. ^ Shirley, D. A. (1954). "The Synthesis of Ketones from Acid Halides and Organometallic Compounds of Magnesium, Zinc, and Cadmium". Org. React. 8: 28–58.
17. ^ Huryn, D. M. (1991). "Carbanions of Alkali and Alkaline Earth Cations: (ii) Selectivity of Carbonyl Addition Reactions". In Trost, B. M.; Fleming, I. (eds.). Comprehensive Organic Synthesis, Book 1: Additions to C—X π-Bonds, Part 1. Elsevier Science. pp. 49–75. doi:10.1016/B978-0-08-052349-1.00002-0. ISBN978-0-08-052349-i.
18. ^ "The Grignard Reaction. Training of Benzoic Acid" (PDF). Portland Customs Higher. Archived from the original (PDF) on 26 February 2015. Retrieved 12 March 2015. >
19. ^ "Experiment ix: Synthesis of Benzoic Acid via Carbonylation of a Grignard Reagent" (PDF). University of Wisconsin-Madison. Archived from the original (PDF) on 23 September 2015. Retrieved 12 March 2015.
20. ^ "Experiment three: Grooming of Benzoic Acid" (PDF). Towson Academy. Archived from the original (PDF) on 13 Apr 2015. Retrieved 12 March 2015. >
21. ^ Amakawa, Kazuhiko; Kolen'Ko, Yury V.; Villa, Alberto; Schuster, Manfred Eastward/; Csepei, Lénárd-István; Weinberg, Gisela; Wrabetz, Sabine; Naumann d'Alnoncourt, Raoul; Girgsdies, Frank; Prati, Laura; Schlögl, Robert; Trunschke, Annette (2013). "Multifunctionality of Crystalline MoV(TeNb) M1 Oxide Catalysts in Selective Oxidation of Propane and Benzyl Alcohol". ACS Catalysis. three (6): 1103–1113. doi:10.1021/cs400010q.
22. ^ Santonastaso, Marco; Freakley, Simon J.; Miedziak, Peter J.; Brett, Gemma 50.; Edwards, Jennifer Chiliad.; Hutchings, Graham J. (21 Nov 2014). "Oxidation of Benzyl Alcohol using in Situ Generated Hydrogen Peroxide". Organic Process Research & Evolution. 18 (11): 1455–1460. doi:ten.1021/op500195e. ISSN 1083-6160.
23. ^ ^{a b c d} Maki, Takao; Takeda, Kazuo (2000). Ullmann'southward Encyclopedia of Industrial Chemical science. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_555. .
24. ^ A D Warth (1 December 1991). "Machinery of action of benzoic acrid on Zygosaccharomyces bailii: effects on glycolytic metabolite levels, energy production, and intracellular pH". Appl Environ Microbiol. 57 (12): 3410–4. Bibcode:1991ApEnM..57.3410W. doi:10.1128/AEM.57.12.3410-3414.1991. PMC183988. PMID 1785916.
25. ^ Pastrorova I, de Koster CG, Blast JJ (1997). "Analytic Study of Free and Ester Bound Benzoic and Cinnamic Acids of Mucilage Benzoin Resins past GC-MS HPLC-frit FAB-MS". Phytochem Anal. viii (ii): 63–73. doi:10.1002/(SICI)1099-1565(199703)8:2<63::AID-PCA337>3.0.CO;two-Y.
26. ^ GSFA Online Food Condiment Grouping Details: Benzoates (2006) Archived 26 September 2007 at the Wayback Machine
27. ^ EUROPEAN PARLIAMENT AND COUNCIL DIRECTIVE No 95/2/EC of twenty February 1995 on food additives other than colours and sweeteners (Consleg-versions practice not contain the latest changes in a law) Archived 19 April 2003 at the Wayback Automobile
28. ^ "Indications of the possible formation of benzene from benzoic acid in foods, BfR Skilful Opinion No. 013/2006" (PDF). High german Federal Institute for Run a risk Assessment. ane Dec 2005. Retrieved xxx March 2022.
29. ^ "Whitfield Ointment". Archived from the original on 9 Oct 2007. Retrieved 15 October 2007.
30. ^ Charles Owens Wilson; Ole Gisvold; John H. Cake (2004). Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical . Lippincott Williams & Wilkins. pp. 234. ISBN978-0-7817-3481-3.
31. ^ Lillard, Benjamin (1919). "Troches of Benzoic Acid". Applied Druggist and Pharmaceutical Review of Reviews.
32. ^ Experiment ii: Using Bomb Calorimetry to Determine the Resonance Energy of Benzene Archived 9 March 2012 at the Wayback Machine
33. ^ ^{a b c} "Concise International Chemical Assessment Document 26: BENZOIC ACID AND SODIUM BENZOATE".
34. ^ Tomokuni K, Ogata M (1972). "Directly Colorimetric Decision of Hippuric Acid in Urine". Clin Chem. eighteen (iv): 349–351. doi:ten.1093/clinchem/18.4.349. PMID 5012256.
35. ^ Vogt, T. (2010). "Phenylpropanoid Biosynthesis". Molecular Plant. 3: 2–twenty. doi:10.1093/mp/ssp106. PMID 20035037.
36. ^ Juteau, Pierre; Valérie Côté; Marie-French republic 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:ten.1099/ijs.0.02914-0. PMID 15653882.
37. ^ Brewster, R. Q.; Williams, B.; Phillips, R. (1955). "3,5-Dinitrobenzoic Acrid". Organic Syntheses. ; Collective Volume, vol. three, p. 337
38. ^ Cosmetic Ingredient Review Skillful Panel Bindu Nair (2001). "Final Report on the Condom Assessment of Benzyl Alcohol, Benzoic Acid, and Sodium Benzoate". Int J Tox. 20 (Suppl. 3): 23–50. doi:10.1080/10915810152630729. PMID 11766131. S2CID 13639993.
39. ^ "butyrate-CoA ligase". BRENDA. Technische Universität Braunschweig. Retrieved 7 May 2014. Substrate/Product
40. ^ "glycine N-acyltransferase". BRENDA. Technische Universität Braunschweig. Retrieved vii May 2014. Substrate/Production
41. ^ Krebs HA, Wiggins D, Stubbs K (1983). "Studies on the mechanism of the antifungal action of benzoate". Biochem J. 214 (iii): 657–663. doi:ten.1042/bj2140657. PMC1152300. PMID 6226283.
42. ^ Bedford PG, Clarke EG (1972). "Experimental benzoic acid poisoning in the cat". Vet Rec. 90 (three): 53–58. doi:x.1136/vr.90.3.53. PMID 4672555. S2CID 2553612.
43. ^ Chen, Jian; Y.Fifty. Kao (18 January 2010). "Well-nigh thirty% dried, pickled foods neglect condom inspections". The China Postal service.

External links [edit]

• International Chemical Condom Card 0103
• SIDS Initial Assessment Report for Benzoic Acid from the Organisation for Economical Co-performance and Development (OECD)
• ChemicalLand

Rf Value Of Benzoic Acid,

Source: https://en.wikipedia.org/wiki/Benzoic_acid

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