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E210 Benzoic acid is the simplest member of the aromatic carboxylic acid family.
E210 Benzoic acid is a weak acid that is a precursor for the synthesis of many important organic compounds.
More than 90 percent of commercial E210 Benzoic acid is converted directly to phenol and caprolactam.
CAS: 65-85-0
MF: C7H6O2
MW: 122.12
EINECS: 200-618-2
Synonyms
210;a 1 (acid);Mefenamic Acid Impurity D;Benzyl acid;SS Benzoic Acid;Glycopyrronium Bromide EP Impurity D;price benzoic acid;Benzoic acid Manufacturer
E210 Benzoic acid's use in the production of glycol benzoates for the application of plasticizer in adhesive formulations is increasing.
E210 Benzoic acid is also used in the manufacture of alkyd resins and drilling mud additive for crude oil recovery applications.
E210 Benzoic acid is also used as a rubber polymerization activator, retardant, resins, alkyd paint, plasticizers, dyestuffs, and fibers.
E210 Benzoic acid and its esters occur in apricots, cranberries, mushrooms and jasmine plants.
The history of E210 Benzoic acid dates back to sixteenth century.
In the year of 1875 Salkowski a prominent scientist discovered its antifungal abilities.
In medicine, E210 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.
E210 Benzoic acid and sodium benzoate are commonly used food preservative.
In acidic conditions, E210 Benzoic acid has inhibitory effect on yeast and mold.
When pH value is 3 antibacterial strength, when pH was 6 for a lot of mould effect is very poor, so the inhibition the optimum pH value is 2.5-4.0.
In the food industry with plastic barrels concentrated fruit and vegetable juice, the maximum usage shall not exceed 2.0g/kg; in the jam (not including canned), fruit juice (taste) drinks, soy sauce, vinegar in the maximum amount is 1.0g/kg; in Wine, candy, wine in the maximum amount of 0.8g/kg in the low salt; pickles, sauces, candied fruit, use the largest 0.5g/kg in carbonate; use the largest beverage 0.2g/kg. because of solubility of benzoic acid, when used will be stirring, or dissolved in a small amount of hot water or ethanol.
The use of concentrated fruit juice in the soft drink used for E210 Benzoic acid easily volatile with steam, E210 Benzoic acid is commonly used in the sodium salt.
E210 Benzoic acid in food industry is a common preservative in dairy products, but not allowed to be added.
In general, E210 Benzoic acid is considered to be safe. But for some special populations, including infants, long-term intake of benzoic acid may lead to asthma, urticaria, metabolic acidosis and other adverse reactions.
Paul deodorant E210 Benzoic acid is also used as a beverage.
As the cream sweet perfume fragrance.
Can also be used for chocolate, lemon, orange, sub berries, nuts, candied fruit and other edible flavor type.
Tobacco flavor also commonly used.
In addition of E210 Benzoic acid is also used as a pesticide, medicine, dye, mordant and plasticizer agent for the production of raw materials, polyamide resin and alkyd resin modifying agent and steel equipment anti rust agent.
E210 Benzoic acid is a colorless, crystalline solid also known as benzenecarboxylic acid.
E210 Benzoic acid is the simplest aromatic carboxylic acid, with a carboxyl group (-COOH) bonded directly to the benzene ring.
E210 Benzoic acid is found naturally in the benzoin resin of a number of plants.
E210 Benzoic acid is a compound comprising a benzene ring core carrying a carboxylic acid substituent.
E210 Benzoic 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.
E210 Benzoic acid is a conjugate acid of a benzoate.
E210 Benzoic acid, H3B03, also known as boracic acid, orthoboric acid, and sassolite, is a white solid composed of triclinic crystals.
E210 Benzoic acid is a derivative of barium oxide and is soluble in water.
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.
E210 Benzoic 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.
The benzoyl group is often abbreviated "Bz" (not to be confused with "Bn", which is used for benzyl), thus E210 Benzoic acid is also denoted as BzOH, since the benzoyl group has the formula −C6H5CO.
E210 Benzoic acid 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 and serves as an intermediate in the biosynthesis of many secondary metabolites.
Salts of benzoic acid are used as food preservatives.
E210 Benzoic acid is an important precursor for the industrial synthesis of many other organic substances.
The salts and esters of E210 Benzoic acid are known as benzoates.
History
E210 Benzoic acid was found in the 16th century.
In 1556, Nostradamus first described carbonization effect of benzoin; After the Alexius Pedemontanus and Brian blessed decipher were discovered in 1560 and 1596.
In 1875, the salkowski discovered the antifungal potency of E210 Benzoic acid, so benzoic acid is used for long term preservation cloudberry.
E210 Benzoic acid Chemical Properties
Melting point: 121-125 °C(lit.)
Boiling point: 249 °C(lit.)
density: 1.08
bulk density: 500kg/m3
vapor density: 4.21 (vs air)
vapor pressure: 10 mm Hg ( 132 °C)
refractive index: 1.504
FEMA: 2131 | BENZOIC ACID
Fp: 250 °F
storage temp.: 2-8°C
solubility: soluble, clear, colorless (95% ethanol, 1gm/3mL)
form: Solid
pka: 4.19(at 25℃)
color: White to yellow-beige to orange
PH: 3.66(1 mM solution);3.12(10 mM solution);2.6(100 mM solution);
Odor: at 100.00 %. faint balsam urine
Odor Type: balsamic
biological source: synthetic
Water Solubility: Slightly soluble. 0.34 g/100 mL
JECFA Number: 850
Merck: 14,1091
BRN: 636131
Henry's Law Constant: (x 10-8 atmm3/mol): 7.02 (calculated, U.S. EPA, 1980a)
Stability: Stable. Combustible. Incompatible with strong bases, strong oxidizing agents, alkalies.
Cosmetics Ingredients Functions: pH ADJUSTERS PRESERVATIVE FRAGRANCE
Cosmetic Ingredient Review (CIR): Benzoic acid (65-85-0)
InChI: 1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
InChIKey: WPYMKLBDIGXBTP-UHFFFAOYSA-N
LogP: 1.870
CAS DataBase Reference: 65-85-0(CAS DataBase Reference)
NIST Chemistry Reference: Benzoic acid(65-85-0)
EPA Substance Registry System: E210 Benzoic acid (65-85-0)
Scaly or needle like crystals. With the smell of formaldehyde or benzene.
Slightly soluble in water, soluble in ethanol, methanol, diethyl ether, chloroform, benzene, toluene, CS2, CCl4 and turpentine.
E210 Benzoic acid, C6H5COOH, also known as benzene carboxylic acid and phenyl formic acid,is a colorless, monoclinic crystalline solid that has a melting point of 122.4"C and sublimes readily at 100·C.
E210 Benzoic acid is an aromatic carboxylic acid that is slightly soluble in water and moderately soluble in alcohol and ether.
E210 Benzoic acid is used as a preservative and its derivatives are valuable in medicine, commerce, and industry.
Colorless to white needles, scales, or powder with a faint benzoin or benzaldehyde-like odor.
Shaw et al. (1970) reported a taste threshold in water of 85 ppm.
Uses
E210 Benzoic acid is an important benzoic acid derivative produced industrially by neutralization of benzoic acid using sodium hydroxide or sodium bicarbonate solution.
Calcium benzoate, potassium benzoate, and other benzoate salts are also produced.
E210 Benzoic acid and sodium benzoate (C6H5COONa) are used as food preservatives and added to foods, juices, and beverages that are acidic.
1. Used as a chemical reagent and preservative.
2. Benzoic acid is important type food preservative.
Under acidic conditions, E210 Benzoic acid has inhibitory effects to mold, yeast and bacteria , but the effect is weak acid producing bacteria.
The most appropriate antimicrobial pH values is ranging from 2.5 to 4, generally lower, the pH value is appropriate from 4.5 to 5.
In the food industry with plastic barrels concentrated fruit and vegetable juice, the maximum use amount shall not be over 2.0g/kg; in jam (excluding canned), (taste) juice drink, soy sauce, vinegar in the maximum dose of 1.0g/kg; in soft candy, wine, wine in the maximum dose of 0.8 g/kg separately; in the low salt pickled vegetables, the sauce, candied fruit, maximum dose is 0.5 g/kg; in carbonated drinks in the largest amount of use is 0.2g/kg. due to benzoic acid, slightly soluble in water, its use can be a small amount of ethanol enable dissolved.
3.Preservative; anti microbial agents.
Due to the low solubility of E210 Benzoic acid and use shall be stirring, or dissolved in a small amount of hot water or ethanol.
When used in the soft drink with fruit juice concentrate, for E210 Benzoic acid easy volatile with the water vapor, so often used in the sodium salt, besides the above sodium equivalent to benzoic acid 0.847g.
4.Often used as a fixative agent or preservative.
Also used as a fruit juice aroma conservation agents.
As a perfume with perfume fragrance.
Can also be used for chocolate, lemon, orange, berries, nuts, candied fruit type edible essence.
Tobacco flavor is also commonly used.
5.E210 Benzoic acid and its sodium salt are food preservatives.
Under acidic conditions, E210 Benzoic acid has inhibition of yeasts and molds.
When pH 3, antibacterial strength and when pH 6, many fungi effect is very poor, so the antibacterial optimum pH is 2.5-4.0.
E210 Benzoic acid is mainly used for the production of sodium benzoate preservatives, dyes intermediates, pesticides, plasticizers, mordant, medicine, spice and also can be used as alkyd resin and polyamide resin modifier for the production of polyester, terephthalic acid and used equipment, iron and steel anti rust agent.
6.Mainly used for antifungal and antiseptic.
7.Used in medicine, dye carriers, plasticizer, spices and food preservatives such as production, and can also be used to paint of alkyd resin performance improvement; used as pharmaceutical and dye intermediates, used for the preparation of plasticizer and spices etc., as well as equipment, iron and steel anti rust agent.
Agricultural Uses
Fungicide, Insecticide: Used in the manufacture of benzoates; plasticizers, benzoyl chloride, alkyd resins, in the manufacture of food preservatives, in use as a dye binder in calico printing; in curing of tobacco, flavors, perfumes, dentifrices, standard in analytical chemistry.
Not currently registered for use in the U.S. E210 Benzoic acid is currently used in about a dozen European countries.
Pharmaceutical Applications
Benzoic acid is widely used in cosmetics, foods, and pharmaceuticals, as an antimicrobial preservative.
Greatest activity is seen at pH values between 2.5–4.5.
Benzoic acid also has a long history of use as an antifungal agent in topical therapeutic preparations such as Whitfield’s ointment (benzoic acid 6% and salicylic acid 3%).
Clinical Use
E210 Benzoic acid is a metabolite of benzyl alcohol and sodium benzoate is the sodium salt of benzoic acid.
These three related compounds are used as preservatives in a variety of products, such as cosmetics, toothpastes, hair products, medication preparations, and emollients, and in foods.
They are well-recognized to cause nonimmunological CoU and reactions are concentration-dependent.
Both oral intake and cutaneous contact of benzyl alcohol, E210 Benzoic acid, or sodium benzoate can cause immediate reactions; however, there is a lack of correlation between the two and skin tests should not be used to predict sensitivity to oral intake of these preservatives.
Immediate reactions to the oral ingestion of these preservatives are rare.
Nettis et al. investigated 47 patients with a history of urticaria after the ingestion of meals or products containing sodium benzoate, and only one patient had a generalized urticarial reaction to an oral challenge test of 50 mg of sodium benzoate.
Calorimetry
E210 Benzoic acid is the most commonly used chemical standard to determine the heat of capacity of a bomb calorimeter.
Feed stock
E210 Benzoic acid is used to make a large number of chemicals, important examples of which are:
Benzoyl chloride, C6H5C(O)Cl, is obtained by treatment of benzoic with thionyl chloride, phosgene or one of the chlorides of phosphorus.
C6H5C(O) Cl is an important starting material for several benzoic acid derivates like benzyl benzoate, which is used in artificial flavours and insect repellents.
Food preservative
E210 Benzoic acid and its salts are used as a food preservatives, represented by the E-numbers E210, E211, E212, and E213.
E210 Benzoic acid inhibits the growth of mold, yeast and some bacteria.
E210 Benzoic acid is either added directly or created from reactions with its sodium, potassium, or calcium salt.
The mechanism starts with the absorption of E210 Benzoic acid in to the cell.
Medicinal
E210 Benzoic acid is a constituent of Whitfiel's ointment which is used for the treatment of fungal skin diseases such as tinea, ringworm, and athlete's foot.
As the principal component of benzoin resin, E210 Benzoic acid is also a major ingredient in both tincture of benzoin and Fria's balsam.
Such products have a long history of use as topical antiseptics and inhalant decongestants.
E210 Benzoic acid was used as an expectorant, analgesic, and antiseptic in the early 20th century.
Preparation
Industrial preparation method
The industrial E210 Benzoic acid is mainly by toluene liquid phase air oxidation preparation.
The process was with cobalt naphthenate as catalyst, in response to temperature is 140-160 ℃ and operating pressure is 0.2-0.3MPa and response generation benzoic acid.
Reaction after steaming to toluene, and vacuum distillation and recrystallization to obtain the product.
The process uses cheap raw materials, high yield.
Therefore, E210 Benzoic acid is industrial uses mainly the method.
Laboratory preparation method of the main reaction:
1.C6H5CH3+ KMnO4+H2O-C6H5 COOK+KOH+MnO2+H2O(water in fron of the manganese dioxide is supplied with water reaction environment)
2.C6H5 COOK+HCl--C6H5 COOH
Drug and dosage:
Toluene 1.5g (1.7ml, 0.016mol), potassium permanganate 5g (0.032mol), CTAB(cetyl trimethyl ammonium bromide) 0.1g.
Experimental operation:
With 100 ml round bottom flask.
Install a refluxing device. add 5g potassium permanganate, 0.1g of hexadecyl trimethyl ammonium bromide, 1.7 ml of toluene and 50 ml of water to the reaction flask, stir heated boiling (vigorous stirring, violent boiling), keep the reactant solution stable boiling.
When large amounts of brown precipitate, potassium permanganate purple shallow or disappeared, the toluene layer disappeared, reaction has basically ended.
Filter out of manganese dioxide precipitation, landfill leachate by concentrated hydrochloric acid, precipitation of benzoic acid precipitation, filtering to the crude product.
The crude product water recrystallization.
In a boiling water bath for drying, weighing, measuring the melting point.
Production Methods
Industrial preparations
E210 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, proceeds in high yield, and is considered environmentally green.
Laboratory synthesis
E210 Benzoic acid is cheap and readily available, so the laboratory synthesis of benzoic acid is mainly practiced for its pedagogical value.
E210 Benzoic acid is a common undergraduate preparation.
For all syntheses, E210 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.
Other possible recrystallization solvents include acetic acid (anhydrous or aqueous), benzene, acetone, petroleum ether, and a mixture of ethanol and water.
The solubility of E210 Benzoic acid in over 40 solvents with references to original sources can be found as part of the Open Notebook Science Challenge.
Reactions
Reactions of E210 Benzoic acid can occur at either the aromatic ring or the carboxyl group :
Aromatic ring
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.
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 E210 Benzoic acid.
E210 Benzoic acid esters are the product of the acid catalysed reaction with alcohols.
E210 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.
Ortho esters 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 , Li Al H4 or sodium boro hydride.
The copper catalyzed 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.
Biotechnological Production
E210 Benzoic acid is exclusively chemically synthesized on an industrial scale.
Toluene from petrochemical routes is oxidized in the presence of the catalyst potassium permanganate to benzoic acid.
However, a recent study described for the first time a benzoic acid production process by fermentation using Streptomyces maritimus.
The production of E210 Benzoic acid during cultivation on glucose, starch, and cellobiose has been investigated.
The best results have been achieved with product concentrations of 460 mg.L-1 in 6 days using starch as substrate.
Additionally, a genetically modified S. maritimus optimized for endo-glucanasesecretion has been tested on phosphoric acid swollen cellulose.
A final product concentration of 125 mg.L-1 was observed after 4 days of cultivation.
Hazard
E210 Benzoic acid accumulation is less, low toxicity in the body involved and metabolism.
If the excessive consumption of benzoic acid, the body's liver and kidney will be jeopardized.
Maximum safety of carbonated drinks of benzoic acid usage is 5mg/kg of body weight, then calculated according to the weight of 60kg, daily limit is 300mg, benzoic acid for carbonated drinks, the maximum amount of use is 0.2g/kg, then drank 1.5kg of beverage is safe.
E210 Benzoic acid has strong toxic effects on microorganisms, but the toxicity of the sodium salt is very low.
A daily dose of 0.5g, has no toxicity to the body , even in an amount of not more than 4g of health also has no harm.
In human and animal tissues E210 Benzoic acid can bind with protein components of the glycine and detoxification, formed hippuric acid excreted in the urine.
Benzoic acid crystallites or dust on the skin, eyes, nose, and throat has stimulating effect.
Even if its sodium salt, if you take a lot, also can damage to the stomach.
The operator should wear protective equipment.
Need to be stored in a dry and ventilated place moisture, heat, away from the fire source.
Side effects
E210 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 %).
Ripe fruits of several Vaccinium species (e.g., cranberry, V. vitis idaea; bilberry, V. macrocarpon) 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, E210 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).
Gum benzoin contains up to 20 % of benzoic acid and 40% benzoic acid esters.
