BENZOIC ACID (BENZOK AST)
BENZOIC ACID (BENZOK AST)
Cas number: 65-85-0
EC number: 200-618-2
synonyms:
benzoic acid; 65-85-0; Dracylic acid; benzenecarboxylic acid; Carboxybenzene; Benzeneformic acid; phenylformic acid Benzenemethanoic acid; Phenylcarboxylic acid; Retardex; Benzoesaeure GK; Benzoesaeure GV; Retarder BA ; Tenn-Plas; Acide benzoique; Salvo liquid; Solvo powder; Benzoesaeure; Flowers of benzoin; Flowers ofbenjamin; Benzoic acid, tech.; Unisept BZA; HA 1 (acid); Kyselina benzoova; Benzoic acid (natural);Benzoate (VAN); HA 1; Benzoesaeure [German]; Caswell No. 081; Diacylic acid; Oracylic acid; Acide benzoique [French];Acido benzoico [Italian]; Benzenemethonic acid; Kyselina benzoova [Czech]; NSC 149;E 210; Benzoicacid; FEMA No. 2131; CCRIS1893; HSDB 704; UNII-8SKN0B0MIM; AI3-0310; Salvo, liquid;Solvo, powder; AI3-03710; Benzoic acid [USAN:JAN]; EPA Pesticide Chemical Code 009101; Benzoic acid Natural;C7H6O2; E210; CHEBI:30746; Aromatic carboxylic acid; EINECS 200-618-2;WPYMKLBDIGXBTP-UHFFFAOYSA-N; Benzeneformate; Phenylformate; Tennplas;MFCD00002398;SBB040515; Benzenemethanoate; Benzenecarboxylate; Retarded BA;DSSTox_CID_143; Phenyl carboxylic acid; DSSTox_RID_75396; DSSTox_GSID_20143;Benzoic acid, ammonium salt; Acido benzoico; CAS-65-85-0; NSC7918; Benzoic acid, tech;Benzoic acid (TN); Benzoic acid [USP:JAN]; phenylcarboxy; Diacylate; Dracylate,Aromatic acid; Salvo powder; Carboxypolystyrene; MP Benzoic acid; Retarder BAX;1gyx; 1kqb; phenyl formic acid; Benzoic Acid USP; Sodium benzoic acid; Natural Benzoic Acid;Benzoic acid,medicinal; Benzoic acid / Benzoate; WLN: QVR; BENZOIC ACID, ACS; 8SKN0B0MIM; BENZOIC ACID- D5;bmse000300; CHEMBL541; Epitope ID:139965; AC1L18SV; AC1Q73KP; SCHEMBL1378;ACMC-1BI02; SAMPL4, O1; PHENYL, 4-CARBOXY-; Benzoic acid (JP17/USP); KSC352Q8R;MLS002415717; ARONIS27062; BIDD:ER0597; Benzoic acid, AR, >=99%; Benzoic acid, LR, >=99%;Benzoic acid, 99% 250g; NSC149; ZINC1011; DTXSID6020143; ScavengePoreTM benzoic acid; CTK2F2888;HMDB01870; Benzoic acid (7CI,8CI,9CI); Benzoic acid, analytical standard; Benzoic acid, p.a., 99.5%;NSC-149; MolPort-000-871-563; BDBM197302; HMS2092F18; HMS2267D03;HMS3652B03; Pharmakon1600-01503001; Tox21_202403; Tox21_300180;ANW-35104; ANW-44013; BENZOIC ACID,99%,EXTRA PURE; LS-280; MFCD03456189;NSC758203; STK301730; Benzoic acid, ReagentPlus(R), 99%; AKOS000119619; AS04617;BS-3752; CCG-213088; DB03793; LS41489; MCULE-4467353796; NE10192;NSC-758203; RL04514; RTR-032704; TRA0015745; TRA0068106; Benzoic acid, >=99.5%, FCC, FG;Benzoic acid, ACS reagent, >=99.5%; NCGC00091886-01; NCGC00091886-02; NCGC00091886-03; NCGC00254112-01;NCGC00259952-01; 117500-35-3; 4CN-0999; AJ-07949; AK109354; AN-22195; AN-23749;Benzoic acid, USP, 99.5-100.5%; BP-30148; BT000118; K073; KB-75310; OR033950;OR320218; OR321743; SC-46861; SMR001252220; Benzoic acid, tested according to Ph.Eur.; SBI-0206720.P001; AB1002068;Benzoic acid, SAJ first grade, >=99.5%; DB-029471; RT-004576; TR-035735; 606-EP2269610A2;606-EP2269988A2; 606-EP2270002A1; 606-EP2270006A1; 606-EP2270008A1; 606-EP2270009A1; 606-EP2270010A1;606-EP2270011A1; 606-EP2270114A1; 606-EP2272822A1; 606-EP2272827A1; 606-EP2272848A1; 606-EP2274983A1;606-EP2275105A1; 606-EP2275401A1; 606-EP2275413A1; 606-EP2277507A1; 606-EP2277848A1; 606-EP2277867A2;606-EP2277870A1; 606-EP2277879A1; 606-EP2277881A1; 606-EP2280003A2; 606-EP2280010A2; 606-EP2281559A1,606-EP2281563A1; 606-EP2281812A1; 606-EP2281819A1; 606-EP2281823A2; 606-EP2284146A2; 606-EP2284147A2;606-EP2284149A1; 606-EP2284160A1; 606-EP2284165A1; 606-EP2284169A1; 606-EP2284178A2; 606-EP2284179A2;606-EP2377845A1; B0062; B2635; FT-0622705; ST24030107; ST45061539;Benzoic acid,natural, >=99.5%, FCC, FG;Benzoic acid, SAJ special grade, >=99.5%; Benzoic acid, Vetec(TM) reagent grade, 98%;Benzoic acid on polystyrene, 1.6-2.1 mmol/g; Benzoic acid, meets USP testing specifications;Benzoic acid, purified by sublimation, >=99%; C00180; C00539; D00038; AB00949635_05; AB00949635_06;A835250; SR-05000001919; Benzoic acid, puriss. p.a., ACS reagent, 99.9%; I01-1943;SR-05000001919-1; 0BE368DC-6DE6-4927-AECF-E4BB2968A4A0; Melting point standard 121-123C, analytical standard;Z57127480; F2191-0092; Benzoic acid, NIST(R) SRM(R) 39j,calorimetric standard;Benzoic acid, Standard for quantitative NMR, TraceCERT(R); S4161,6585-0;S4162,121-54-0,Benzoic acid, European Pharmacopoeia (EP) Reference Standard; Benzoic acid, for calorimetrical determination (approx. 26460 J/g);
Benzoic acid, pharmaceutical secondary standard; traceable to USP; Benzoic acid, United States Pharmacopeia (USP) Reference StandardBenzoic acid，4-fluoro-2,6dimethyl-， methyl ester; InChI=1/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9;;Benzoic acid, puriss. p.a., ACS reagent, reag. Ph. Eur., >=99.9% (alkalimetric); 331473-08-6;8013-63-6; Benzoic acid, certified reference material for titrimetry, certified by BAM according to ISO 17025, >=99.5%;Benzoic acid, meets analytical specification of Ph. Eur., BP, USP, FCC, E210, ;99.5-100.5% (alkalimetric); BOX;Carboxypolystyrene, 100-200 mesh, extent of labeling: 0.5-1.5 mmol/g loading, 1 % cross-linked;
Carboxypolystyrene, 100-200 mesh, extent of labeling: 1.6-3.0 mmol/g loading, 1 % cross-linked;Mettler-Toledo Calibration substance ME 18555, Benzoic acid, analytical standard,;for the calibration of the thermosystem 900, traceable to primary standards (LGC);ScavengePore(TM) benzoic acid, macroporous, 40-70 mesh, extent of labeling: 0.5-1.5 mmol per g loading;Acide benzoique ;Aromatic carboxylic acid; Benzenecarboxylic acid; Benzeneformic acid ;Benzenemethanoic acid; Benzoesaeure; Dracylic acid; e210; Phenylcarboxylic acid;Phenylformic acid; Benzoate; Aromatic carboxylate; Benzenecarboxylate; Benzeneformate ;Benzenemethanoate; Dracylate; Phenylcarboxylate; Phenylformate;Benzenemethonic acid; Benzoic acid sodium salt; Carboxybenzene; Diacylate ;Diacylic acid; Oracylic acid; Sodium benzoate; Sodium benzoic acid;Acid, benzoic MeSH; Kendall brand OF benzoic acid sodium salt; Benzoate, potassium; Potassium benzoate; Ucephan;Benzoic acid (IUPAC Name); benzene carboxylic acid; Benzenecarboxylic acid; benzeneformic acid; Benzenemethanoic acid;Phenylformate; Benzenecarboxylic acid; Benzeneformic acid; Benzenemethanoic acid; Benzoesaeure GK; Benzoesaeure GV ;Carboxybenzene; Dracylic acid; Phenylcarboxylic acid; Phenylformic acid; Retarder BA; Retardex; Salvo, liquid; Solvo, powder ;
Tenn-Plas; Acide benzoique; Benzoic acid, tech.; Kyselina benzoova; Benzoesaeure; Salvo powder; E 210; HA 1; HA 1 (acid);Phenylcarboxy; Benzenemethonic acid; Diacylic acid; Flowers of benjamin; Flowers of benzoin; Oracylic acid; Retarder BAX; NSC 149;Bronsted-Lowry acid, Bronsted acid, carboxylate, acetic acid, acrylic acid,methacrylic acid, formic acid, fumaric acid,ethanoic acid, malonic acid, maleic acid, salicyclic acid, succinic acid, phthalic acid, isophthalic acid, terephthalic acid, lactic acid, propionic acid, propanoic acid, pyruvic acid, tartaric acid, mesotartaric acid, racemic acid, meta-chloroperoxybenzoic acid,peracetic acid, acetoacetic acid, arachidic acid, arachidonic acid, lauric acid, linoleic acid, linolenic acid, myristic acid, oleic acid,palmitic acid, stearic acid, amino acid, aspartic acid, glutamic acid, ascorbic acid, folic acid, formaldehyde, formyl group,hydroxyl group, carbonyl group; benzoikasit; benzoik asit; benzoik asid; benzoikasid; benzoikacit; benzoik acit;benzoik asid; benzoyik asit; benzoyik acid; Benzoik Acid; Benzoik acid; benzoik Acid; BENZOIK ACID; BENZOIK AST; KARBOKSBENZEN; karboksibenzen; karboksi benzen; benzoikacid; benzenkarboksilikasit; benzen karboksilitasit; benzen karboksilikacid; Benzoyik Acite; Benzoyik Acite; benzenkarboksilikacit; benzoicasit;benzoic acit; benzoic asid; Benzoic asid; Benzoik Asit; Benzoic Asit; Benzoik asit; Benzoyik asit; benzoyik asit; benzoyic acit; benzoik acit; benzoyik acide; benzoyik acide; Benzoik Acit; Benzoyik Acide; Benzoyik Acide; benzoyik acite; benzoyik acite; Benzoik Acit; BENZOIK Acit; BENZOK AST; BENZOK ACD; BENZOK ASDE; benzoikasit; acide benzoique; acide benzoic; L’acide benzoique; L’ acide benzoic; Benzoik Asit; Benzoic Asit; Benzoik asit; Benzoyik asit; benzoyik asit; benzoyic acit; benzoik acit; benzoyik acide; benzoyik acide
Benzoic acid
Names
Preferred IUPAC name
Benzoic acid[1]
Systematic IUPAC name
Benzenecarboxylic acid
Other names
Carboxybenzene
E210
Dracylic acid
Phenylmethanoic acid
BzOH
Identifiers
CAS Number
65-85-0 ☑
Benzoic acid /bɛnˈzoʊ.ɪk/ is a white (or colorless) solid with the formula C6H5CO2H. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source. Benzoic acid occurs naturally in many plants[9] and serves as an intermediate in the biosynthesis of many secondary metabolites. Salts of benzoic acid are used as food preservatives. 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/.
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).[10]
Justus von Liebig and Friedrich Wöhler 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
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 abundant materials, and proceeds in high yield.[13]
toluene oxidation
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.
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. This process usually gives a yield of around 65% [14]
By hydrolysis
Like other nitriles and amides, benzonitrile and benzamide can be hydrolyzed to benzoic acid or its conjugate base in acid or basic conditions.
From Grignard reagent
Bromobenzene can be converted to benzoic acid by “carboxylation” of the intermediate phenylmagnesium bromide.[15] 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.[16][17][18][19][20]
Oxidation of benzyl compounds
Benzyl alcohol[21][22] and benzyl chloride and virtually all benzyl derivatives are readily oxidized to benzoic acid.
Uses
Benzoic acid is mainly consumed in the production of phenol by oxidative decarboxylation at 300-400 °C:[23]
Precursor to plasticizers
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 benzoyl chloride 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 E numbers E210, E211, E212, and E213. Benzoic acid inhibits the growth of mold, yeast[24] 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.[25] 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 local food laws.[26][27]
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 carcinogenic benzene.[28]
See also: Benzene in soft drinks
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.[29][30] 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 was used as an expectorant, analgesic, and antiseptic in the early 20th century.[31]
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. 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
In teaching laboratories, benzoic acid is a common standard for calibrating a bomb calorimeter.[32]
Biology and health effects
Benzoic acid occurs naturally as do its esters in many plant and animal species. Appreciable amounts are 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).[33] Gum benzoin contains up to 20% 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 4-hydroxybenzoate.[36]
Reactions
Reactions of benzoic acid can occur at either the aromatic ring or at the carboxyl group:
Aromatic ring
benzoic acid aromatic ring reactions
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.[37] 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
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 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.
benzoic acid group reactions
Safety and mammalian metabolism
It is excreted as hippuric acid.[38] Benzoic acid is metabolized by butyrate-CoA ligase into an intermediate product, benzoyl-CoA,[39] which is then metabolized by glycine N-acyltransferase into hippuric acid.[40] Humans metabolize toluene and benzoic acid which is excreted as hippuric acid.[41]
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.[33] 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.[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 dried and pickled food products had benzoic acid.[43]
Benzoic acid appears as a white crystalline solid. Slightly soluble in water. The primary hazard is the potential for environmental damage if released. Immediate steps should be taken to limit spread to the environment. Used to make other chemicals, as a food preservative, and for other uses.
Benzoic acid, C6H5COOH, is a colourless crystalline solid and the simplest aromatic carboxylic acid. 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%). Cranberries contain as much as 300-1300 mg free benzoic acid per kg fruit. Benzoic acid is a fungistatic compound that is widely used as a food preservative. It often is conjugated to glycine in the liver and excreted as hippuric acid. Benzoic acid is a byproduct of phenylalanine metabolism in bacteria. It is also produced when gut bacteria process polyphenols (from ingested fruits or beverages).
Benzoic acid is a compound comprising a benzene ring core carrying a carboxylic acid substituent. It has a role as an antimicrobial food preservative, an EC 3.1.1.3 (triacylglycerol lipase) inhibitor, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, a plant metabolite, a human xenobiotic metabolite, an algal metabolite and a drug allergen. It is a conjugate acid of a benzoate.
Benzoic Acid
Benzoic acid or benzene-carbonic-acid is a monobasic aromatic acid, moderately strong, white crystalline powder, very soluble in alcohol, ether, and benzene, but poorly soluble in water (0.3 g of benzoic acid in 100 g of water at 20 °C).
Benzoic acid has the advantage that it does not affect the odor or taste of the soft drink, if used in small quantities. The preserving quality of benzoic acid is based on its activity to delay the multiplication of several groups of microorganisms, which, however, are not killed by this product. The low solubility of benzoic acid in water complicates its application in products containing large amounts of water. Therefore, the water-soluble salt sodium benzoate is used.
This product, which is the salt of benzoic acid, has no preserving activity by itself. Therefore, after addition of sodium benzoate, the acidity of the soft drink is increased (pH < 3.5), with the result that free undissociated benzoic acid is formed, which has a preserving property. In an alkaline environment, benzoic acid is split into ions and thus loses its preserving activity.
Sodium benzoate is the sodium salt of benzoic acid used as a white crystalline or amorphous (without crystal structure) powder, very soluble in water (66 g of sodium benzoate in 100 g of water at 20 °C) but poorly soluble in alcohol.
Description of of Benzoic Acid;
Benzoic acid, C6H5COOH, is a colourless crystalline solid and the simplest aromatic carboxylic acid. 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%). Cranberries contain as much as 300-1300 mg free benzoic acid per kg fruit. Benzoic acid is a fungistatic compound that is widely used as a food preservative. It often is conjugated to glycine in the liver and excreted as hippuric acid. Benzoic acid is a byproduct of phenylalanine metabolism in bacteria. It is also produced when gut bacteria process polyphenols (from ingested fruits or beverages).
Formula of Benzoic Acid : C7H6O2
Physical and Chemical Properties of Benzoic Acid;
Boiling point of Benzoic Acid; 249 °C (1013 hPa)
Density of Benzoic Acid; 1.321 g/cm3 (20 °C)
Flash point of Benzoic Acid; 121 °C
Ignition temperature of Benzoic Acid; 570 °C
Melting Point of Benzoic Acid; 121 – 123 °C
pH value of Benzoic Acid; 2.5 – 3.5 (H²O, 20 °C) (saturated solution)
Vapor pressure of Benzoic Acid; 0.001 hPa (20 °C)
Bulk density of Benzoic Acid; 500 kg/m3
Solubility of Benzoic Acid; 2.9 g/l
Physical Description of Benzoic Acid;
DryPowder
Liquid
Liquid, PelletsLargeCrystals
OtherSolid
PelletsLargeCrystals
Color of Benzoic Acid;
White scales or needle crystals
Odor of Benzoic Acid;
Odorless or with a slight benzaldehyde odor
Application of Benzoic Acid;
Benzoic acid, a white, crystalline organic compound belonging to the family of carboxylic acids, widely used as a food preservative and in the manufacture of various cosmetics, dyes, plastics, and insect repellents.
First described in the 16th century, benzoic acid exists in many plants; it makes up about 20 percent of gum benzoin, a vegetable resin. It was first prepared synthetically about 1860 from compounds derived from coal tar. It is commercially manufactured by the chemical reaction of toluene (a hydrocarbon obtained from petroleum) with oxygen at temperatures around 200° C (about 400° F) in the presence of cobalt and manganese salts as catalysts. Pure benzoic acid melts at 122° C (252° F) and is very slightly soluble in water.
Among the derivatives of benzoic acid are sodium benzoate, a salt used as a food preservative; benzyl benzoate, an ester used as a miticide; and benzoyl peroxide, used in bleaching flour and in initiating chemical reactions for preparing certain plastics.
Benzoic acid has been used in the preparation of vials for the HPLC analysis of various polyamines in biological fluids, tissues and isolated/cultured cells.
It may be employed as an intermediate in the synthesis of the following
• paints
• pigments
• varnish
• wetting agents
• aroma compounds
• benzoyl chloride
• benzotrichloride
It may also be used to investigate the mechanism of complex addition reaction of hydroxyl radicals with various aromatic compounds.
More than 90 percent of commercial benzoic acid is converted directly to phenol and caprolactam. Its use in the production of glycol benzoates for the application of plasticizer in adhesive formulations is increasing. The organic compound is also used in the manufacture of alkyd resins and drilling mud additive for crude oil recovery applications. It is also used as a rubber polymerization activator and retardant.
Benzoic acid is converted to its salts and esters for use as a preservative application in foods, drugs, and personal products. In medicine, benzoic acid is the principal component of benzoin resin, and 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.
Industry Uses of Benzoic Acid;
Adhesives and sealant chemicals
Agricultural chemicals (non-pesticidal)
Intermediates
Lubricants and lubricant additives
Paint additives and coating additives not described by other categories
Plasticizers
Consumer Uses of Benzoic Acid;
Adhesives and Sealants
Agricultural Products (non-pesticidal)
Anti-Freeze and De-icing Products
Building/Construction Materials not covered elsewhere
Electrical and Electronic Products
Floor Coverings
Lubricants and Greases
Paints and Coatings
Personal Care Products
Plastic and Rubber Products not covered elsewhere
Benzoik asit
Benzoik asit Görünümü : Renksiz, Kristal Veya Toz Yapda Kat
Kimyasal Ad : Benzenecarboxylci Acid, Carboxybenzene, Benzoik asit
Benzoik asit Kimyasal Formülü : C6H5COOH
Benzoik asit Ambalaj ekli : 25 kg’lk torbalarda
Benzoik asit Tanm ve Kullanm Alanlar :
Benzoik asit C6H5COOH renksiz bir kat kristalin ve basit bir aromatik karboksilik asittir. ad uzun bir süre sadece bilinen kaynak oldu sakz benzoin, elde edilir. Benzoik asit birçok bitki doal olarak bulunan ve bir çok ikincil metabolitlerin biyosentezinde bir ara madde olarak hizmet eder. benzoik asit tuzlar, gda koruyucu maddeler olarak kullanlan ve benzoik asit birçok organik maddelerin endüstriyel sentezi için önemli bir ön-madde olan. tuzlar ve benzoik asit esterleri benzoatlar olarak bilinir.
Benzoik asitin Kullanm Alanlar
Benzoik asit Gdalarda mikrobik bozunmay önlemek için kullanlr.
Benzoik asit En çok kullanld alanlar meyve suyu, marmelat, reçel, gazl içecekler, turular, ketçap ve benzeri ürünlerdir.
Benzoik asit ve tuzlar, asitli ve zayf asitli gdalarda koruyucu katk maddesi olarak kullanlr ve çou organik maddenin sentezi için önemli bir ön maddedir.
Ticari olarak elde edilen benzoik asidin %90′ direk olarak fenole ve kaprolaktama dönütürülür.
Kozmetikte ampuanlarn, parfümlerin, tra köpüklerinin, saç spreylerinin ve saç boyalarnn içeriklerinde de benzoik asit bulunmaktadr.
Benzoik asit Otomobillerin antifrizlerinde soutucu ksmna eklenen kimyasallarn içeriine katlr.
Benzoik asit Tütün ilaçlamada ve dier böcek öldürücü ilaç içeriklerinde yer alr.
Benzoik asit Analitik kimya labotaruvarlarnda standart referans olarak kullanlr.
Benzoik asit Whitfield Merhemi eklinde derideki mantar hastalklarnda kullanlr.
Benzoik asitle ilgili bilgilendirme:
CAS numaras
65-85-0
EC numaras
200-618-2
PubChem
243
ChemSpider
238
RTECS numaras
DG0875000
Moleküler formülü
C7H6O2
Molar kütle
122.12 g mol-1
Görünü
Renksiz kristal kat
Younluk
1.27 g/cm3
Benzoik asit özellikle ilenmi yiyeceklerde bulunan bir katk maddesidir. çikolata, çeitli meyve sular, ekerlemeler, dondurma, kremalar ve ciklette bulunur. benzoik asit, astm, deri döküntülerigibi çeitli allerjik raksiyonlara neden olur. aspirin allerjisi olan kiilerin daha dikkatli olmalar gerekir.
Molekül arl 122.12 olan benzoik asit (C6H5COOH); beyaz pulcuk ya da küçük kristaller halinde olan bir organik asittir. Organik çözücü karmnda ve scak suda kolaylkla çözülebilmektedir. Benzoik asit (BA) alkol, eter, benzen, kloroform, karbon disülfit ve karbon tetraklorid içerisinde yüksek çözünürlük gösterir fakat suda çok az bir çözünme özelliine sahiptir.
Benzoik asit ilk kez 1988 ylnda Avrupa’da üretilmitir. lk olarak 16. yüzylda benzoin reçinesinden kuru damtma yöntemiyle elde edilmitir. 1875 ylnda mayalanma ve küflenmeye kar etkili olduu görülmü ve böylece gda sektöründe yaygn bir ekilde kullanlmaya balanmtr.
Benzoik asidin türevleri ve tuzlar; sodyum benzoat (C6H5COONa), benzonitril (C6H5 CN), benzoik asit anhidriti (C6H5CO)2O)
Benzoik asidin dsal uygulanmas ile bitkilerin biyotik ve abiyotik streslere kar tolerans kazandrdn gösteren çalmalar bulunmaktadr. Örnein domates ve fasulye bitkileri ile yaplan çalmalarda uygulanan benzoik asidin scaklk, kuraklk ve souk streslerine kar bitkilerin tolerans kazand görülmütür. Yaplan bir baka çalmada da benzoik asidin buday fidelerinde kadmiyum toksisitesine kar koruyuculuk salad görülmütür. Ayrca bitki patojenine kar da bitkiyi koruduunu gösteren çalmalar bulunmaktadr.
Benzoik asit nerelerde kullanlr?
1- Benzoik asitin En yaygn olarak kullanld sektör gda sektörüdür. Gdalarda mikrobiyolojik bozulmay önlemek için kullanlr. En çok kullanld alanlar ise meyve suyu, reçel, marmelat, gazl içecekler, turular, ketçap ve benzeri ürünlerdir.
2- Yaban mersini, kuru erik, kzlck, karanfil, tarçn ve yourt gibi baz gdalarda doal olarak da bulunan benzoik asit genellikle sodyum tuzu formunda gdalarda koruyucu katk maddesi olarak kullanlmaktadr.
3- Benzoik asit ve türevleri antimikrobiyal özellik gösterdikleri için baz içeceklerde, çikolata, mayonez, sakz, çerez gibi gdalarda da kullanlabilmektedir.
4- Benzoik asit Kimyevi, tbbi malzemelerin üretiminde kullanlmaktadr.
5- Benzoik asit Farmasötik ürünlerde antimikrobiyal koruyucu olarak kullanlmaktadr.
6- Benzoik asit; ampuan, tra köpüü, saç kremi gibi kozmetik ürünlerinin içindeki kimyevi muhteviyat korumak için katlmaktadr.
7- Kauçuk ve latekslerde sertletirici, deterjanlar için kimyasal bir inhibitör olarak da Benzoik asit kullanlmaktadr.
8- Benzoik asit Böcek ve bitki ilaçlamada kullanlan bu maddenin kimyasallar koruyucu etkisi bulunur.
9- Otomobillerde de kullanm alanna sahiptir. Antifrizlerin soutucu ksmna eklenen kimyasallarn içeriine Benzoik asidin katld da bilinmektedir.
10- Ayrca derideki mantar hastalklarnda da kullanld bilinmektedir.
Kullanm alanlar bu kadar geni çapl olan Benzoik asidin zararlar da bulunmaktadr. Sulu çözeltisi asit özellii gösterir hatta asetik asitten biraz daha kuvvetli asittir. Deri, göz ve mukozal zarlar üzerinde tahri edici etkiye sahiptir, solunduunda öksürük yapar. Baz kiilerde bu maddeye kar alerjik durum görülebilir. Bu maddenin sk kullanlmasna bal olarak astm rahatszl ortaya çkabilir. Benzoik asidin oral, dermal ya da solunum yolu ile alnmasnn vücutta ürtiker, astm, rinit ve anaflaktik ok gibi oluumlara neden olduu belirlenmitir. Benzoik asit vücutta hzl bir metabolizma faaliyeti içerisinde ilem görmekte ve vücut tarafndan atlmaktadr dolaysyla dokularda herhangi bir birikme neden olmamaktadr.
Benzoik Asidin Tanm;
Benzoik asit, C6H5COOH, renksiz, kristalimsi bir katdr ve en basit aromatik karboksilik asittir. Benzoik asit, birçok bitki ve hayvan türünde doal olarak serbest bulunur ve benzoik asit esterleri olarak balanr. Çileklerin çounda takdir edilebilir miktarlar bulunmutur (yaklak% 0,05). Kzlck, kg meyve bana 300-1300 mg serbest benzoik asit içerir. Benzoik asit, gda koruyucusu olarak yaygn olarak kullanlan fungistatik bir bileiktir. Genellikle karacierdeki glisinle konjuge edilir ve hippurik asit olarak atlr. Benzoik asit bakterilerde fenilalanin metabolizmasnn bir yan ürünüdür. Barsak bakterileri polifenolleri (yutulan meyvelerden veya içeceklerden) ilerken de üretilir.
Benzoik asitin formülü: C7H6O2
Benzoik Asitin Fiziksel ve Kimyasal Özellikleri;
Benzoik Asidin Kaynama Noktas; 249 ° C (1013 hPa)
Benzoik Asit Younluu; 1.321 g / cm3 (20 ° C)
Benzoik Asit Parlama Noktas; 121 ° C
Benzoik Asitin Ateleme Scakl; 570 ° C
Benzoik Asitin Erime Noktas; 121 – 123 ° C
Benzoik Asit’in pH deeri; 2.5 – 3.5 (H20, 20 ° C) (doymu çözelti)
Benzoik Asidin buhar basnc; 0.001 hPa (20 ° C)
Benzoik Asit younluu; 500 kg / m3
Benzoik Asidin Çözünürlüü; 2,9 g / l
Benzoik Asitin Fiziksel Tanm;
Kuru Toz
Sv
Sv, Pellet Büyük Kristaller
Dier katlar
Pelet Büyük Kristaller
Benzoik Asitin Rengi;
Beyaz bsküller veya ine kristalleri
Benzoik Asit Koku;
Kokusuz veya hafif bir benzaldehid kokusu ile
Benzoik Asit Uygulamas
Benzoik asit, karboksilik asit ailesine ait, gda koruyucusu olarak ve çeitli kozmetik, boya, plastik ve böcek kovucularnn imalatnda kullanlan beyaz, kristalimsi bir organik bileiktir.
lk defa 16. yüzylda tanmlanan benzoik asit birçok bitki içinde bulunur; Bu, sebze reçinesinin sakz benzoininin yüzde 20’sini oluturuyor. lk önce kömür katranndan türetilmi bileiklerden sentetik olarak yaklak 1860 hazrland. Ticari olarak katalizör olarak kobalt ve manganez tuzlarnn varlnda toluen’in (petrol tarafndan elde edilen bir hidrokarbon) yaklak 200 ° C (yaklak 400 ° F) scaklktaki oksijen ile kimyasal reaksiyonu ile üretilir. Saf benzoik asit 122 ° C’de (252 ° F) erir ve suda çok az çözünür.
Benzoik asit türevleri arasnda gda koruyucusu olarak kullanlan bir tuz olan sodyum benzoat; Benzil benzoat, bir mitit öldürücü olarak kullanlan bir ester; Ve benzoil peroksit, unun aartlmasnda ve baz plastiklerin hazrlanmas için kimyasal tepkimelerin balatlmasnda kullanlr.
Benzoik asit biyolojik svlar, dokular ve izole edilmi / kültürlenmi hücrelerdeki çeitli poliaminlerin HPLC analizi için flakonlarn hazrlanmasnda kullanlmtr.
Aadaki sentezde bir ara madde olarak kullanlabilir
• boyalar
• pigmentler
• vernik
• slatma maddeleri
• aroma bileikleri
• benzoil klorür
• benzotrimlorür
Hidroksil radikallerinin çeitli aromatik bileiklerle kompleks ilaveli reaksiyon mekanizmasn aratrmak için de kullanlabilir.
Ticari benzoik asidin% 90’dan fazlas dorudan fenol ve kaprolaktam haline dönütürülür. Yapkan formülasyonlarda plastikletiricinin uygulanmas için glikol benzoatlarn üretiminde kullanm artmaktadr. Organik bileik, ham ya geri kazanm uygulamalar için alkid reçineleri ve delme çamuru katk maddesinin imalatnda da kullanlr. Ayn zamanda bir kauçuk polimerizasyon etkinletiricisi ve geciktirici olarak kullanlr.
Benzoik asit gdalar, ilaçlar ve kiisel ürünlerdeki koruyucu bir uygulama olarak kullanlmak üzere tuzlarna ve esterlerine dönütürülür. Tpta benzoik asit benzoin reçinesinin ana bileenidir ve tinea, bademcik ve atlet aya gibi mantar cilt hastalklarnn tedavisinde kullanlan Whitfield merheminin bir unsurudur.
Benzoik Asit Sanayi Kullanm;
Yaptrclar ve dolgu macunu kimyasallar
Tarmsal kimyasallar (böcek öldürücü olmayan)
Ara ürünler
Yalayclar ve ya katklar
Dier kategorilerde anlatlmayan boya katklar ve kaplama katklar
plastikletiriciler
Benzoik Asitin Tüketici Kullanmlar;
Yaptrclar ve Yaptrclar
Tarm Ürünleri (böcek öldürücü olmayan)
Antifriz ve Buz Çözücü Ürünler
Bina / naat Malzemeleri baka yerde kapsanmamaktadr
Elektrikli ve Elektronik Ürünler
Zemin Kaplamalar
Yalayclar ve Gresler
Boyalar ve Kaplamalar
Kiisel Bakm ürünleri
Baka yerde kapsanmayan plastik ve kauçuk ürünler
L’acide benzoïque
L’acide benzoïque, de formule chimique C6H5COOH (ou C7H6O2) est un acide carboxylique aromatique dérivé du benzène.
Description
L’acide benzoïque est utilisé comme conservateur alimentaire et est naturellement présent dans certaines plantes. C’est par exemple l’un des principaux constituants de la gomme benjoin, utilisée dans des encens dans les églises de Russie et d’autres communautés orthodoxes. Bien qu’étant un acide faible, l’acide benzoïque n’est que peu soluble dans l’eau du fait de la présence du cycle benzénique apolaire.
On trouve de l’acide benzoïque dans les plantes alimentaires :
– en quantité notable dans le canneberge d’Amérique11 (Vaccinium macrocarpon) : 48,10 mg·100ml-1.
– dans une moindre mesure dans la poudre de cacao (Theobroma cacao) : 0,06 mg·100ml-1.
Parmi les principaux composés qui dérivent de l’acide benzoïque, on peut citer l’acide salicylique et l’acide acétylsalicylique plus connu sous le nom d’aspirine.
En tant qu’additif alimentaire, il est référencé en Europe sous le code E210. Ses sels, que l’on appelle des benzoates, sont référencés sous les numéros :
E211 Benzoate de sodium (Ba)
E212 Benzoate de potassium (Ba)
E213 Benzoate de calcium (Ba)
Au-dessus de 370 °C, il se décompose en formant du benzène et du dioxyde de carbone. L’acide benzoïque a une odeur forte et est facilement inflammable.
Historique
En 1830, Wöhler rencontre Justus von Liebig, qui poursuit des recherches similaires sur les cyanates. Ils extraient, en 1837, l’amygdaline à partir des amandes amères, et découvrent l’acide benzoïque en oxydant l’amygdaline par l’acide nitrique. En 1832, ils publient les résultats de travaux et montrent que les radicaux organiques peuvent se combiner à l’hydrogène électropositif aussi bien qu’à l’oxygène électronégatif. Ils éditent ensemble les Annalen der Chemie und Pharmazie.
Production du acide benzoïque
Production industrielle
L’acide benzoïque est produit industriellement par oxydation partielle du toluène par l’oxygène en phase gazeuse en présence de catalyseurs tels que des sels de cuivre12 ou le pentoxyde de vanadium (V2O5).
Synthèse au laboratoire
L’acide benzoïque est peu cher et disponible auprès de nombreux fournisseurs. Sa synthèse au laboratoire est seulement pratiquée à titre d’exercices pédagogiques.
L’oxydation du toluène, de l’alcool benzylique ou du benzaldéhyde par le permanganate de potassium produit aussi de l’acide benzoïque.
On peut l’obtenir par l’hydrolyse d’un composé de même niveau d’oxydation que lui (par exemple à partir du benzonitrile ou du benzamide).
On peut aussi l’obtenir par réaction d’un réactif de Grignard avec le dioxyde de carbone. Le schéma réactionnel ci-dessous montre par exemple l’obtention de l’acide benzoïque à partir du bromobenzène.
Benzoic acid synthesis.png
Précautions
Phrases de risque :
R22 (Nocif en cas d’ingestion)
R36 (Irritant pour les yeux)
Conseils de prudence :
S24 (Éviter le contact avec la peau)
Risques
Selon une étude britannique publiée en 2007, l’acide benzoïque favorise l’hyperactivité infantile, plus précisément le trouble du déficit de l’attention13,14.
Alimentation
L’acide benzoïque fait partie des additifs alimentaires et porte le numéro SIN E21015.
L’acide benzoïque est aussi contenu naturellement dans certains aliments (notamment dans les fruits de la Plaquebière…)
Réglementation
Sur le plan de la réglementation des produits phytopharmaceutiques :
pour l’Union européenne : cette substance active est inscrite à l’annexe I de la directive 91/414/CEE par la directive 2004/30/CE.
pour la France : cette substance active est autorisée dans la composition de préparations bénéficiant d’une autorisation de mise sur le marché.
Acide benzoïque
Sodium Benzoate, Benzoic Acid
L’acide benzoïque provient avant tout de la résine du benjoin, mais on le retrouve également chez d’autres plantes, ainsi que dans le miel et les produits laitiers.
Son sel, le benzoate de sodium, est soluble et convient également comme agent conservateur pour les produits alimentaires et cosmétiques.
Ces deux agents inhibent la croissance de levures et de moisissures, et ont également un effet légèrement antimicrobien.
acide benzoïque : C6H5COOH solide blanc aspect soyeux ; monoacide faible peu soluble dans l’eau ( 3g/L à 25 °C) ; masse molaire : 122 g/mol ; conservateur alimentaire utilisé dans les boissons rafraichissantes sans alcool (
L’acide benzoïque est un acide carboxylique aromatique dérivé du benzène. Il se trouve à l’état naturel dans certains fruits ou dans certaines plantes. Commercialement, l’acide benzoïque est produit par synthèse chimique à partir du toluène. La dose journalière admissible (DJA) établie pour ce conservateur peut être dépassée, en particulier chez les enfants forts consommateurs d’aliments vecteurs (comme les boissons aromatisées). Des réactions d’hypersensibilité et d’allergies ont aussi été recensées (asthme, prurit, rougeurs). L’acide benzoïque est enfin soupçonné de favoriser l’hyperactivité chez les enfants, seul ou en combinaison avec des colorants azoïques.
Fonction principale Conservateur
Famille Acide benzoïque et ses sels