Quick Search
Benzenecarboxylic acid is a white or colorless crystalline organic compound with the formula C6H5COOH, whose structure consists of a benzene ring (C6H6) with a carboxyl (−C(=O)OH) substituent.
CAS Number: 55582-31-5
EC Number: 200-618-2
IUPAC Name: Benzenecarboxylic acid
Chemical Formula: C10H8O3
Other names: 65-85-0, Dracylic acid, benzenecarboxylic acid, Benzeneformic acid, Carboxybenzene, phenylformic acid, Benzenemethanoic acid, Phenylcarboxylic acid, Retardex, Retarder BA, Tenn-Plas, Salvo liquid, Benzoesaeure GK, Benzoesaeure GV, Acide benzoique, Solvo powder, Benzoic acid, tech., Unisept BZA, Benzoesaeure, HA 1 (acid), Kyselina benzoova, FEMA No. 2131, Benzenemethonic acid, Vevovitall, Acido benzoico, Menno-florades, Benzoicum acidum, E 210, AI3-0310, DTXSID6020143, Acidum benzoicum, NSC-149, 8SKN0B0MIM, Benzoic acid (e 210), Sodium benzoic acid, Tennplas, INS NO.210, E210, CHEBI:30746, INS-210, Phenyl carboxylic acid, DTXCID80143, E-210, Provita, Provita Combat, Whitfield's, Eyelids Wipes, Provita Equiband, Acid, Benzoic, Rheumatism Diarrhea, Benzoate, Potassium, RefChem:6620, 200-618-2, hydron;benzoate, Benzoic acid (natural), Benzoate (VAN), HA 1, Benzoesaeure [German], Caswell No. 081, Diacylic acid, Oracylic acid, Acide benzoique [French], Acido benzoico [Italian], Kyselina benzoova [Czech], NSC 149, CCRIS 1893, Diacylate, HSDB 704, Salvo, liquid, Solvo, powder, AI3-03710, MFCD00002398, EPA Pesticide Chemical Code 009101, Aromatic carboxylic acid, Benzoic acid (Standard), Salvo powder, Benzoic acid [USAN:JAN], CAS-65-85-0, NSC7918, 14322-82-8, EINECS 200-618-2, UNII-8SKN0B0MIM, Benzoic acid [USP:JAN], phenylcarboxy, Dracylate, benzoic aicd, benzoic-acid, benzoic_acid, bezoic acid, Aromatic acid, benzenecarboxylic, Benzyl acid, benzoic- acid, Retarder BAX, 1gyx, 1kqb, Benzoic acid CRS, Glycopyrronium Bromide EP Impurity D, Benzoic acid (NIST), 760 - Preservatives, ANTAZOLINE_met016, WLN: QVR, benzene-2-carboxylic acid, EUCATROPINE_met034, Benzoic acid, 99.5%, CYCLANDELATE_met022, BENZOIC ACID [II], BENZOIC ACID [MI], Benzoic acid, ACS reagent, bmse000300, CHEMBL541, Epitope ID:139965, EC 200-618-2, BENZOIC ACID [FCC], BENZOIC ACID [JAN], SCHEMBL1378, SCHEMBL1809, BENZOIC-4-D1 ACID, BENZOIC ACID [FHFI], BENZOIC ACID [HSDB], SAMPL4, O1, TRIPELENNAMINE_met034, SCHEMBL20583, SCHEMBL22028, Benzoic acid (JP18/USP), BENZOIC ACID [VANDF], Benzoic acid - Melting point, MLS002415717, 27 - Preservatives in Cream, BENZOIC ACID [MART.], BIDD:ER0597, SCHEMBL129247, BENZOIC ACID [USP-RS], BENZOIC ACID [WHO-DD], BENZOIC ACID [WHO-IP], Benzoic acid, AR, >=99%, Benzoic acid, LR, >=99%, NSC149, orb1224318, orb1310251, orb3029218, SCHEMBL1518068, SCHEMBL1533094, SCHEMBL1939722, SCHEMBL3859000, SCHEMBL4626763, 31 - Preservatives in Mascara, BENZOICUM ACIDUM [HPUS], SCHEMBL11324395, HY-N0216R, Benzoic acid (7CI,8CI,9CI), Benzoic acid, analytical standard, Benzoic acid, p.a., 99.5%, MSK2501, BENZOIC ACID [GREEN BOOK], BDBM197302, HMS2092F18, HMS2267D03, HMS3652B03, HMS5082G22, Pharmakon1600-01503001, BENZOIC ACID [EP MONOGRAPH], HY-N0216, MBA96084, SAA21784, Tox21_202403, Tox21_300180, BENZOIC ACID [USP MONOGRAPH], EBC-04017, MFCD03456189, NSC758203, s4161, SBB040515, STK301730, Benzoic acid, ReagentPlus(R), 99%, AKOS000119619, Benzoic acid 100 |Ig/mL in Acetone, BS-3752, CCG-213088, DB03793, FB33492, NSC-758203, ACIDUM BENZOICUM [WHO-IP LATIN], Benzoic acid 100 microg/mL in Acetone, Benzoic acid, >=99.5%, FCC, FG, Benzoic Acid (tablets), 100 x 1.0g, Benzoic acid, ACS reagent, >=99.5%, NCGC00091886-01, NCGC00091886-02, NCGC00091886-03, NCGC00091886-05, NCGC00254112-01, NCGC00259952-01, TIAPROFENIC ACID IMPURITY D [EP], Benzoic acid, USP, 99.5-100.5%, BP-30148, MSK2501-1000, SMR001252220, SY009192, Benzoic acid, tested according to Ph.Eur., SBI-0206720.P001, Benzoic acid, SAJ first grade, >=99.5%, DB-029471, B0062, B2635, Benzoic Acid(Discontinued,See C4X-18172), CS-0008257, NS00008785, ST45061539, SW219833-1, Benzoic Acid 2000 |Ig/mL in Dichloromethane, Benzoic acid, natural, >=99.5%, FCC, FG, Benzoic acid, SAJ special grade, >=99.5%, Benzoic acid, Vetec(TM) reagent grade, 98%, EN300-18007, 2-BENZOYL-5-METHOXYBENZOQUINONE_met032, Benzoic acid on polystyrene, 1.6-2.1 mmol/g, Benzoic acid, meets USP testing specifications, C00180, C00539, D00038, D85168, MEFENAMIC ACID IMPURITY D [EP IMPURITY], AB00949635_05, AB00949635_06
Some uses of Benzenecarboxylic acid:
1. Use as a precursor to plasticizer:
Benzenecarboxylic acid is the ingredient needed in the production of Benzoate and Dibenzoate plasticizers.
These plasticizers are mainly used in flooring, film, adhesives, and sealants.
Typical Benzoate plasticizers include Isodecyl Benzoate (IDB) and Isononyl Benzoate (INB).
Common Dibenzoate plasticizers include Dipropylene Glycol Dibenzoate and Neopentylglycol Dibenzoate.
2. Benzenecarboxylic acid use as a feed additive
Pig farmers around the globe have been relying on Zinc Oxide to counter piglets’ Post-Weaning Diarrhea (PWD) for decades.
Yet Zinc Oxide's use has been restricted in recent years due to its severe environmental repercussions.
In face of the coming ban of Zinc Oxide in EU, and the growing restriction on its use globally, feed additive manufacturers have turned to Benzenecarboxylic acid as an alternative.
Either administered directly or applied with slow-releasing coatings, Benzenecarboxylic acid is effective in the prevention and mitigation of PWD.
Benzenecarboxylic acid poses no harm to the environment due to its organic nature.
Moreover, Benzenecarboxylic acid can also accelerate piglets’ fattening process.
3.Use as a Food Preservative and a Precursor to other Benzoic Salt Preservatives:
Benzenecarboxylic acid is a powerful anti-septic agent widely used in food and animal feed.
However, due to its poor solubility, Benzenecarboxylic acid is often more preferable to use its salts instead.
Sodium salt, Calcium salt, and Potassium salt of Benzenecarboxylic acid are among the most common food preservatives in the modern food industry.
Some uses of Benzenecarboxylic acid:
Batteries
Cleaning products and household care
Air freshener
Home air fresheners, including candles
Cleaning products and household care
Carpet and floor
Cleaning products for carpet or other flooring, which do not fit into a more refined category
Additive
Bulking
Cleaning products and household care
General household cleaning
Cleaning products for general household cleaning
Laboratory supplies
Products specifically used in a laboratory setting, e.g. laboratory diagnostics or consumables, solvents and reagents used in experiments or laboratory.
Personal care
General personal care products which do not fit into a more refined category.
Fragrance ingredient
Masking
Non-functional constituent
Personal care
Acne treatment
Facial cleansing products (excluding scrubs), for acne treatment
Personal care
Body hygiene
Body wash
Body cleaners, washes, shower gels
Body hygiene
Hand soap
Liquid hand soaps
Baby lotion
Baby cream or lotion (excluding diaper creams)
Baby wipes
Textile wipes and towelettes specifically marketed for use on infants
Dental care
Mouthwash
Antiseptic and dental mouthwashes and rinses
Toothpastes and dentrifices
Deodorants and antiperspirants
Facial cleansing and moisturizing
Face cleansing wipes
Textile wipes or pads treated with cleansing solution applied to the face to clean or improve the characteristics of skin on the face
Facial cleansing and moisturizing
Face cream/moisturizer
Moisturizers, lotions, and creams for treating the face (excluding eye-specific products)
Face mask
Leave-on masks or peels for treatment of the face
General moisturizing
Hand/body lotion
Products specifically marketed for application to hands or body to moisturize or improve skin characteristics (excluding baby lotion)
Hair styling and care
General hair styling or hair care products
Hair conditioner
Rinse-out everyday hair conditioners (excluding combo shampoo/conditioner products)
Hair conditioning treatment
Hair styling products for imparting hold, shine, or texture to hair
Shampoos, including dual shampoo/conditioner products
Make-up and related products
Lip products primarily for protection
Lip color
Colored lip products, excluding glosses
Lip liner
Pencils for lining lips
Products for removing face make-up
Sexual wellness products, including personal lubricants
Shaving and hair removal
Aftershave products applied to the skin following shaving to provide scent, or improve skin characteristics
Shaving creams, foams, balms and soaps
Specialized bath products
Bubble bath
Products added to bath water to create bubbles, may provide cleaning, fragrance, or improve skin characteristics (including bubble bath marketed to babies or children)
Pesticides
Insect repellent
Skin products for repelling insects from skin
pH regulating agent
ph adjuster
plasticizer
preservatives and antioxidants
Benzenecarboxylic acid is used as a food and drug preservative.
Furthermore, Benzenecarboxylic acid is used as a chemical standard and intermediate.
The largest use of Benzenecarboxylic acid is as a chemical raw material in the production of phenol, caprolactam, glycol dibenzoates esters, and sodium and/or potassium benzoate.
Benzenecarboxylic acid is used in reserving foods, fats, fruit juices, alkaloidal solutions; manufacture of benzoates & benzoyl compounds, dyes; in calico printing; for curing tobacco.
Benzenecarboxylic acid is mainly consumed in the production of phenol by oxidative decarboxylation at 300−400 °C.
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.
Benzenecarboxylic acid can be used as recursor to plasticizers.
Benzoate plasticizers, such as the glycol-, diethyleneglycol-, and triethyleneglycol esters, are obtained by transesterification of methyl benzoate with the corresponding diol.
These plasticizers, which are used similarly to those derived from terephthalic acid ester, represent alternatives to phthalates.
Benzenecarboxylic acid can be precursor to sodium benzoate and related preservatives.
Further, Benzenecarboxylic acid and its salts are used as food preservatives, represented by the E numbers E210, E211, E212, and E213.
Benzenecarboxylic acid inhibits the growth of mold, yeast and some bacteria.
Benzenecarboxylic acid is either added directly or created from reactions with its sodium, potassium, or calcium salt.
The mechanism starts with the absorption of Benzenecarboxylic 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 Benzenecarboxylic acid and benzoate is thus dependent on the pH of the food.
Benzenecarboxylic acid, benzoates and their derivatives are used as preservatives for acidic foods and beverages such as citrus fruit juices (citric acid), sparkling drinks (carbon dioxide), soft drinks (phosphoric acid), pickles (vinegar) and other acidified foods.
Typical concentrations of Benzenecarboxylic acid as a preservative in food are between 0.05 and 0.1%.
Foods in which Benzenecarboxylic acid may be used and maximum levels for its application are controlled by local food laws.
However, concern has been expressed that Benzenecarboxylic acid and its salts may react with ascorbic acid (vitamin C) in some soft drinks, forming small quantities of carcinogenic benzene.
Benzenecarboxylic acid is a constituent of Whitfield's ointment which is used for the treatment of fungal skin diseases such as ringworm and athlete's foot.
As the principal component of gum benzoin, Benzenecarboxylic 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.
Benzenecarboxylic acid was used as an expectorant, analgesic, and antiseptic in the early 20th century.
Furthermore, Benzenecarboxylic acid has niche and laboratory uses
In teaching laboratories, Benzenecarboxylic acid is a common standard for calibrating a bomb calorimeter.
Some important uses of Benzenecarboxylic acid are listed below:
The production of phenol involves the use of Benzenecarboxylic acid.
Benzenecarboxylic acid is used in ointments that prevent or treat fungal skin diseases.
Moreover, Benzenecarboxylic acid is used as a preservative in the food industry.
Benzenecarboxylic acid is an ingredient in many cosmetic products, such as lipsticks.
Benzenecarboxylic acid is also a precursor to benzoyl chloride, which finds its application in making other chemicals, dyes, perfumes, herbicides and medicines.
One of the components of toothpaste, mouthwash, and face wash creams is Benzenecarboxylic acid.
Benzenecarboxylic acid is also used in the manufacture of dyes and in insect repellants.
Some other uses of Benzenecarboxylic acid:
Adhesives and sealant chemicals
Agricultural chemicals (non-pesticidal)
Cosmetics and personal care
Finishing agents
Food and beverage additive, preservative
Heat Stabilizer
Intermediates
Lubricants and lubricant additives
Paint additives and coating additives not described by other categories
Plasticizers
Solvents (for cleaning and degreasing)
Solvents (which become part of product formulation or mixture)
Surface active agents
Adhesives and sealants
Agricultural products (non-pesticidal)
Anti-freeze and de-icing products
Automotive care products
Building/construction materials not covered elsewhere
Cleaning and furnishing care products
Electrical and electronic products
Floor coverings
Food / Beverage / Nutrition use.
Laundry and dishwashing products
Lubricants and greases
Mixed Metal Heat Stabilizer
Non-TSCA use
Paints and coatings
Personal care products
Plastic and rubber products not covered elsewhere
Toys, playground, and sporting equipment
Auto Products
Inside the Home
Personal Care
Pet Care
Personal care product
Manufacturing industry
Material processing agent
Coloring agent
Fluorescent agent
Antipyretic
Expectorant
Fungicide
Vulnerary
Food and nutrition
Food additive
Flavoring agent
Agriculture
Pesticide
Insecticide
Pesticide
Pharmaceutical industry
Biomarker
Eosinophilic esophagitis
Biological role
Waste product
Allergen
Anesthetic
Anti bacterial
Anti otitic
Anti salmonella
Anti septic
Anti yeast
Choleretic
Fungicide
Insectifuge
Phytoalexin
Uricosuric
Modulator
Inhibitor
Enzyme inhibitor
EC 1.14.18.1 (tyrosinase) inhibitor
Environmental role
Air pollutant
Adhesives
Agricultural Chemicals
Cosmetics
Personal Care
Finishing Agents
Food and Beverage Additive
Preservative
Heat Stabilizer
Lubricants
Paint Additives
Solvents
Floor Coverings
DESCRIPTION
Benzenecarboxylic acid is the simplest aromatic carboxylic acid.
More to that, Benzenecarboxylic acid is used in the production of numerous industrial additives such as the Benzoate plasticizers.
Together with several of Benzenecarboxylic acid's salts, Benzenecarboxylic acid is used as food and feed preservatives.
Esters of Benzenecarboxylic acid are common fragrances.
In recent years, Benzenecarboxylic acid is also found to be effective against piglets’ post-weaning diarrhea when administered as a feed additive.
Benzenecarboxylic acid appears as a white crystalline solid.
Moreover, Benzenecarboxylic acid is lightly soluble in water.
The primary hazard of Benzenecarboxylic acid is the potential for environmental damage if released.
Immediate steps should be taken to limit spread of Benzenecarboxylic acid to the environment.
Benzenecarboxylic acid is used to make other chemicals, as a food preservative, and for other uses.
Benzenecarboxylic acid is a compound comprising a benzene ring core carrying a carboxylic acid substituent.
More to that, Benzenecarboxylic acid 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.
Benzenecarboxylic acid is a conjugate acid of a benzoate.
Benzenecarboxylic acid is a white (or colorless) solid organic compound, whose structure consists of a benzene ring (C6H6) with a carboxyl (−C(=O)OH) substituent.
Further, Benzenecarboxylic acid is the simplest aromatic carboxylic acid.
The name of Benzenecarboxylic acid is derived from gum benzoin, which was for a long time its only source.
Benzenecarboxylic acid occurs naturally in many plants and serves as an intermediate in the biosynthesis of many secondary metabolites.
Salts of Benzenecarboxylic acid are used as food preservatives.
Benzenecarboxylic acid is an important precursor for the industrial synthesis of many other organic substances.
The salts and esters of Benzenecarboxylic acid are known as benzoates.
Benzenecarboxylic acid was discovered in the sixteenth century.
Benzenecarboxylic 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.
Benzenecarboxylic acid, C6H5COOH, is a colourless crystalline solid and the simplest aromatic carboxylic acid.
More to that, Benzenecarboxylic acid occurs naturally free and bound as benzoic acid esters in many plant and animal species.
Appreciable amounts of Benzenecarboxylic acid have been found in most berries (around 0.05%). Cranberries contain as much as 300-1300 mg free Benzenecarboxylic acid per kg fruit.
Benzenecarboxylic acid is a fungistatic compound that is widely used as a food preservative.
Moreover, Benzenecarboxylic acid often is conjugated to glycine in the liver and excreted as hippuric acid.
Benzenecarboxylic acid is a byproduct of phenylalanine metabolism in bacteria.
Benzenecarboxylic acid is also produced when gut bacteria process polyphenols (from ingested fruits or beverages).
Additionally, Benzenecarboxylic acid can be found in Serratia.
First described in the 16th century, Benzenecarboxylic acid exists in many plants.
Benzenecarboxylic acid makes up about 20 percent of gum benzoin, a vegetable resin.
Benzenecarboxylic acid was first prepared synthetically about 1860 from compounds derived from coal tar. Also, Benzenecarboxylic acid 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 Benzenecarboxylic acid melts at 122° C (252° F) and is very slightly soluble in water.
Among the derivatives of Benzenecarboxylic 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.
Industrial preparations of Benzenecarboxylic acid:
Benzoic acid is produced commercially by partial oxidation of toluene with oxygen.
The process is catalyzed by cobalt or manganese naphthenates.
The process uses abundant materials, and proceeds in high yield.
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 Benzenecarboxylic acid with hydrochloric acid.
The product contains significant amounts of chlorinated Benzenecarboxylic acid derivatives.
For this reason, Benzenecarboxylic acid for human consumption was obtained by dry distillation of gum benzoin.
Food-grade Benzenecarboxylic acid is now produced synthetically.
Laboratory synthesis of Benzenecarboxylic acid:
Benzenecarboxylic acid is cheap and readily available, so the laboratory synthesis of Benzenecarboxylic acid is mainly practiced for its pedagogical value.
Furthermore, Benzenecarboxylic acid is a common undergraduate preparation.
Benzenecarboxylic 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%.
Preperation of Benzenecarboxylic acid by hydrolysis:
Like other nitriles and amides, benzonitrile and benzamide can be hydrolyzed to Benzenecarboxylic acid or its conjugate base in acid or basic conditions.
From Grignard reagent:
Bromobenzene can be converted to Benzenecarboxylic acid by "carboxylation" of the intermediate phenylmagnesium bromide.
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.
Oxidation of benzyl compounds:
Benzyl alcohol and benzyl chloride and virtually all benzyl derivatives are readily oxidized to Benzenecarboxylic acid.
Benzenecarboxylic acid, the simplest benzene-based carboxylic acid, has been known since the 16th century.
One of its discoverers was the legendary clairvoyant Nostradamus.
Most common natural source of Benzenecarboxylic acid is gum benzoin, a resin found in the bark of trees of the genus Styrax.
Most Benzenecarboxylic acid produced today is synthetic.
First industrial synthesis of Benzenecarboxylic acid was the hydrolysis of benzotrichloride to calcium benzoate, followed by acidification.
This method has been completely displaced by the air oxidation of toluene, which avoids the problem of product contamination with chlorinated byproducts.
Many processed foods contain Benzenecarboxylic acid or one of its salts as a preservative.
Benzenecarboxylic acid inhibits the growth of bacteria, molds, and yeasts.
Furthermore, Benzenecarboxylic acid works best when the food has an acidic pH value.
Benzenecarboxylic acid is often found in topical antifungal preparations.
Benzenecarboxylic acid consists of a carboxyl group attached to a benzene ring.
Therefore, Benzenecarboxylic acid is said to be an aromatic carboxylic acid.
Benzenecarboxylic acid exists as a crystalline, colourless solid under normal conditions.
The commercial production of Benzenecarboxylic acid is done via the partial oxidation of toluene with oxygen, catalyzed by manganese or cobalt naphthenates.
Another industrial method of preparing Benzenecarboxylic acid is by reacting tri-chlorotoluene with calcium hydroxide in the presence of water, and the treatment of the calcium benzoate product with hydrochloric acid.
