Benzoic Acid
Benzyl acid · Acide benzoique · Benzoesaeure · Benzoic acid, for analysis ACS · Nipacide · Benzoic aBenzoic acidcid · FEMA 2131 · a 1 (acid)
Identifiers & Physical Properties
| CAS No. | 65-85-0 |
|---|---|
| Molecular formula | C7H6O2 |
| Average molar mass | 122.12 g/mol |
| Monoisotopic mass | 122.03677943 g/mol |
| SMILES | O=C(O)c1ccccc1 |
| InChIKey | WPYMKLBDIGXBTP-UHFFFAOYSA-N |
| PubChem CID | 243 |
| ChEMBL | CHEMBL541 |
| ChEBI | CHEBI:30746 |
| EC No. | 200-618-2 |
| DTXSID | DTXSID6020143 |
Chemical & Physical Properties
| XLogP | 1.9 |
|---|---|
| Topological polar surface area | 37.3 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 1 |
| Heavy atoms | 9 |
| Formal charge | 0 |
| Complexity | 103 |
| pH | About 4 (solution in water)pH = 2.8 (Saturated soln at 25 °C)3.66(1 mM solution)3.12(10 mM solution)2.6(100 mM solution) |
| LogP (partition coefficient) | 1.87log Kow = 1.87 |
| LogS | -1.55 |
| Odor | Odorless or with a slight benzaldehyde odorFAINT, PLEASANT ODORat 100.00 %. faint balsam urine |
| Taste | ALMOST TASTELESS /BENZOIC ACID USP/BITTER TASTETaste detection 8.5X10+1 ppm /Media and purity not specified/ |
| Density | 1.316 at 82.4 °F (USCG, 1999) - Denser than waterwill sink1.2659 g/cu cm at 15 °CSp gr: 1.316 at 24 °C/4 °C (solid)1.029 at 180 °C/4 °C (liquid)1.3 g/cm³Relative density of the vapour/air-mixture at 20 °C (air = 1): 11.316 @ 15°C1.08 |
| Viscosity | 1.26 cP at 130 °C |
| Color/Form | Monoclinic tablets, plates, leafletsWhite scales or needle crystalsMonoclinic leaflets or needles |
| Solubility | less than 1 mg/mL at 68 °F (NTP, 1992)3400Mixtures of excess benzoic acid & water form 2 liquid phases beginning at 89.7 °Cthe two phases unite at critical solution temperature of 117.2 °Csolubility in water increased by alkaline substances.Monomer & dimer models for solubility of benzoic acid in simple binary and ternary solvents are reported.In water, 3.5X10+3 mg/L at 25 °C1 g dissolves in: 2.3 mL alcohol (cold), 1.5 mL alcohol (boiling), 4.5 mL chloroform, 3 mL ether, 3 mL acetone, 30 mL carbon tetrachloride,10 mL benzene, 30 mL carbon disulfide, 23 mL oil of turpentine. Also soluble in volatile and fixed oilsslightly soluble in petroleum ethersoluble, clear, colorless (95% ethanol, 1gm/3mL)Slightly soluble. 0.34 g/100 mL |
| Flash point | 250 °F (NTP, 1992)250 °F (121 °C) (closed cup)121 °C c.c. |
| Boiling point | 480 °F at 760 mmHg (NTP, 1992)249.2249.2 °C at 760 mm Hg249 °C249 °C @760 [mm Hg]249 °C(lit.) |
| Decomposition | When heated to decomp it emits acrid smoke and irritating fumes. |
| Melting point | 121-125 °C(lit.) |
| 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 |
| FLAVIS Number | 08.021 | Benzoic acid |
| Storage conditions | 2-8°C |
| Physical state | Solid |
| pKa (acidity coefficient) | 4.19(at 25℃) |
| Color | White to yellow-beige to orange |
| Odor type | balsamic |
| Biological source | synthetic |
| Specific heat capacity | Cp(crystal): 1.2 J/(g·K), at 25℃ |
| 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 ADJUSTERSPRESERVATIVEFRAGRANCE |
| 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 |
| SMILES | OC(=O)c1ccccc1 |
| LogP (partition coefficient) | 1.870 |
| CAS DataBase Reference | 65-85-0(CAS DataBase Reference) |
| Substances Added to Food (formerly EAFUS) | BENZOIC ACID |
| FDA 21 CFR | 175.300177.1390 |
| SCOGS (Select Committee on GRAS Substances) | Benzoic Acid |
| EWG's Food Scores | 1-3 |
| FDA UNII | 8SKN0B0MIM |
| NIST Chemistry Reference | Benzoic acid(65-85-0) |
| EPA Substance Registry System | Benzoic acid (65-85-0) |
| UNSPSC Code | 77101502 |
| NACRES | NA.24 |
| GHS pictogram | GHS05,GHS08 |
| Signal word | Danger |
| GHS hazard statements | H315-H318-H372 |
| GHS precautionary statements | P280-P302+P352-P305+P351+P338+P310-P314 |
| Target organs | Lungs |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Faceshields, Gloves |
| Hazard symbols | Xn,T,Xi |
| Risk statements (R) | 22-36-42/43-36/37/38-40-63-43-23/24/25-45-41-37/38-20/21/22-48/23-38-67-37 |
| Safety statements (S) | 26-45-37/39-24-22-36/37-24/25-23-53-36-63-39 |
| UN transport number | UN 3077 9/PG 3 |
| Water hazard class (WGK) | 1 |
| RTECS number | DG0875000 |
| F | 21 |
| Autoignition temperature | 570 °C |
| Hazard Note | Harmful |
| TSCA inventory status | TSCA listed |
| Customs code | 2916 31 00 |
| Hazard class | 9Eye Dam. 1Skin Irrit. 2STOT RE 1 Inhalation |
| Storage class | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Hazardous substances data | 65-85-0(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 1700 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
| REACH registrations | Active |
| Limited quantities | 5.0 kg (11 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
Safety & Regulations
| GHS classification | DangerH315: Causes skin irritation [Warning Skin corrosion/irritation]H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]P260, P264, P264+P265, P270, P280, P302+P352, P305+P354+P338, P317, P319, P321, P332+P317, P362+P364, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.9% (28 of 3274) of reports. |
|---|---|
| Regulatory information | Chemical: Benzoic acidRegulation (EC) No 1831/2003 (amended)Benzoic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzoic acid are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)04/30/EC, Reg. (EU) 2016/2016, Reg. (EU) 2017/1113, Reg. (EU) No 540/2011, Reg. (EU) No 823/2012Status: Active Update: 30-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13124Benzoic acid: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | IMAP assessments - Benzoic acid: Environment tier I assessmentIMAP assessments - Benzoic acid: Human health tier II assessment |
| Fire hazards | Behavior in Fire: Vapor from molten benzoic acid may form explosive mixture with air. Concentrated dust may form explosive mixture. (USCG, 1999)Combustible. Finely dispersed particles form explosive mixtures in air. Risk of fire and explosion on contact with incompatible substances. See Chemical Dangers. |
| Fire potential | Slight, when exposed to heat or flame...Benzoic acid is burned in oxygen as primary thermochemical standard to calibrate oxygen bomb calorimeters used in... determination of calorific value of liquid hydrocarbon fuels. If the benzoic acid is powdered (rather than pelleted...), very rapid combustion occurs and flame front may burn through the non-metallic... seals on valve seats and the bomb may be destroyed. |
| Health hazards | Dust may be irritating to nose and eyes. At elevated temperatures, fumes may cause irritation of eyes, respiratory system, and skin. (USCG, 1999) |
| Hazards summary | A skin and eye irritant[ICSC] Causes non-immunological contact urticaria[Kanerva, p. 218] Benzoic acid alkali salts cause pseudoallergic reactions[MAK] TLV Basis: Irritation of eye and respiratory tract, and lung damageLow level oral exposures are considered safe . . . [ACGIH] See Sodium benzoate and Potassium benzoate. |
| FDA requirements | Substance added directly to human food affirmed as generally recognized as safe (GRAS). Current usage results in a max level of 0.1% in food.This substance is generally recognized as safe for use at a level not exceeding 0.1 percent in accordance with good manufacturing or feeding practice.Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: Benzoic acid is included in topical acne drug products.Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: Benzoic acid is included in skin protectant drug products.Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: Benzoic acid is included in topical antifungal drug products. |
| Reactive group | Acids, Carboxylic |
| Special Reports | USEPASubst Risk Notice, 8EHQ-1177-0018 (1978).Benzoic acid, Indian Chemical Manufacturers Association, Indian Exchange, Indian Exchange Place, Calcutta 700 001, India, 1986. CIS/88/00785NTIS/PB85-141216, Benzoic acid. Scientific Literature Review of Benzyl Alcohol, Benzaldehyde, Benzoic Acid and Related Cmpds in Flavor Usage. NTIS Order No. PB85-141216 |
| EPA Safer Chemical | Chemical: Benzoic acidGreen circle - The chemical has been verified to be of low concern based on experimental and modeled data. |
| FIFRA requirements | Residues of benzoic acid are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops or to raw agricultural commodities after harvest. Use: preservative for formulations.Residues of benzoic acid are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to animals. Use: preservative for formulations.As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Benzoic acid is found on List D. Case No: 4013Pesticide type: Insecticide, fungicideCase Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.Active ingredient (AI): Benzoic acidAI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled." |
| Reactivity Profile | At high temperature BENZOIC ACID can react with oxidizing reagents. |
| Fire fighting | Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| First aid measures | Fresh air, rest.Remove contaminated clothes. Rinse and then wash skin with water and soap.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Refer for medical attention . |
| First aid | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.INHALATION: IMMEDIATELY leave the contaminated areatake deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be usedif not available, use a level of protection greater than or equal to that advised under Protective Clothing.INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992) |
| Safe storage | Store only in original container. Separated from incompatible materials. See Chemical Dangers. Fireproof. Store in an area without drain or sewer access. |
| Exposure control and personal protection | 0.5 [mg/m3], respirable fraction (2 mg/m3, inhalable fraction)[German Research Foundation (DFG)] |
| Fire fighting procedures | If material on fire or involved in fire: Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. |
| Storage conditions | The bulk material should be stored in well-closed container in a cool dry place. |
| Cleanup methods | Cover with soda ash or sodium bicarbonate. Mix and add water.Environmental considerations: Land spill: Dig a pit, pond, lagoon, or holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be contained with a flexible impermeable membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water.Environmental considerations: Water spill: If dissolved, in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount. Remove trapped material with suction hoses. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.Personal protection: protective clothing and face shield. Sweep spilled substance into covered plastic containers. If appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water. |
| Disposal methods | SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.The following wastewater treatment technologies have been investigated for benzoic acid: concentration process: biological treatment.Incineration: Waste material can be burned in an approved incinerator with an afterburner, as a soln in a flammable solvent or as a solid packaged in paper, plastic or cardboard.The following wastewater treatment technologies have been investigated for benzoic acid: concentration process: activated carbon.The following wastewater treatment technologies have been investigated for benzoic acid: concentration process: resin adsorption. |
| Spillage disposal | Personal protection: protective clothing and face shield. Do NOT let this chemical enter the environment. Sweep spilled substance into covered plastic containers. Carefully collect remainder in covered containers. If appropriate, moisten first to prevent dusting. Then store and dispose of according to local regulations. |
| Preventive Measures | SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary.For more Preventive Measures (Complete) data for BENZOIC ACID (6 total), please visit the HSDB record page. |
| Eye Prevention | Wear safety goggles. |
| Body burden | Benzoic acid was found in one of twelve breath samples taken from people in New Jersey. Benzoic acid was not found in the drinking water or air samples from this study(1). |
| Interactions | The metabolism of the benzoates depletes glycine concentrations and can therefore alter the glycine-dependent metabolism of other compounds. /Investigators/ demonstrated that benzoic acid or sodium benzoate successfully competed with aspirin for glycine, resulting in increased concentration and persistence of salicylic acid in the body. Almost total inhibition of salicyluric acid formation in humans was achieved using either 2.7 g benzoic acid or 3.2 g sodium benzoate.In rat liver microsomes deferoxamine was a potent inhibitor of the oxidation of the scavenging agent, benzoate. Nearly complete inhibition was observed at 33-100 uM.Groups of 25 male and 25 female mice were given benzoic acid at a dose of 40 mg/kg bw/day, sodium bisulfite at 80 mg/kg bw/day, or a mixture of the two for 17 months. Mortality was greater in the groups receiving the mixture (62%) than in those receiving the individual substances (32%) at eight months.Wistar rats /were administered/ 40 mg benzoic acid/kg/day and 80 mg sodium bisulphite/kg/day once daily /for/ 72 weeks. 50 rats /with/ initial body weight /of/ 100-120g /experienced/ reduced weight gain, kidney function and reaction on stress factors were altered (no further information), /and/ the erythrocyte sedimentation rate was increased. |
| Health effects | People must absorb small amounts of copper every day because copper is essential for good health, however, high levels of copper can be harmful. Very-high doses of copper can cause damage to your liver and kidneys, and can even cause death. Copper may induce allergic responses in sensitive individuals. (L278, L279) |
| Ecotoxicity values | LC50Species: Colinus virginianus (Northern bobwhite quail) diet >5620 ppm for 8 daysSpecies: Anas platyrhynchos (Mallard duck) diet >5620 ppm for 8 daysLD50Species: Anas platyrhynchos (Mallard duck) oral via capsule >2510 mg/kgEC50Species: Anabaena inaequalis (Cyanobacteria)Conditions: staticConcentration: 9 mg/L for 14 daysEffect: cell multiplication inhibitionFor more Ecotoxicity Values (Complete) data for BENZOIC ACID (16 total), please visit the HSDB record page. |
| Environmental fate | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 15(SRC), determined from a structure estimation method(2), indicates that benzoic acid is expected to have very high mobility in soil(SRC). The pKa of benzoic acid is 4.20(3), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the compound exists as an anion and anions do not volatilize. Benzoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 7.0X10-4 mm Hg at 25 °C(5). Mineralization half-life in Captina silt loam for benzoic acid in solution was 4.5 hr after a 30 minute lag(6) and complete degradation occurred in 1 day using a Niagra silt loam inoculum(7), suggesting that biodegradation may be an important fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 15(SRC), determined from a structure estimation method(2), indicates that benzoic acid is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 4.20(3) indicates benzoic acid will exist almost entirely in the anion form at pH values of 5 to 9 and, therefore, volatilization from water or moist soil surfaces is not expected to be an important fate process(SRC). According to a classification scheme(4), a BCF range of <10 to 21(5) suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation half-lives of 0.85 and 3.6 days using inoculum from a polluted river and a reservoir, respectively(6), suggest that biodegradation may be an important fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benzoic acid, which has a vapor pressure of 7X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase benzoic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 9 days(SRC), calculated from its rate constant of 1.2X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Benzoic acid absorbs light at wavelengths >290 nm(4) and, therefore, may be expected to be susceptible to direct photolysis by sunlight(SRC). |
| Food survey values | Apple wine and apple essence contain 0.329 and 40 ppm of benzoic acid, respectively(1). Benzoic acid and sodium benzoate are common food additives, being used as food preservatives at a concentration of 0.1% and as antimicrobial agents in food at concentration levels of 0.29-0.00001%(1). Most berries contain about 0.05% of benzoic acid(2). Benzoic acid has been detected but not quantified in pine sprout tea(3). Benzoic acid has been detected in concentrations of 10, 50, 10, and <5 ppb in canned creamed, canned kernel, frozen kernel, and fresh kernel sweet corn, respectively(4). Benzoic acid was detected in fine particle organic matter emitted from Chinese cooking. Four representative restaurants in Guangzhou city, China: Cantonese style (fresh local ingredients, lightly seasoned, stir fry, peanut and blended oil)Hunan style (spicy and sour dishes, steamed, peanut oil)Sichuan style (sharp and spicy, sauteing, blended oil), and Dongbei style (home-cooking, pot roast, simmering, marinating, canola and peanut oil) Average benzoic acid concentrations in fine particulates were 39, 17, 30, and 20 ng/mg of POM (particulate organic matter), respectively(5). |
| Adverse effects | ACGIH Carcinogen - Not Suspected. |
| Exposure routes | The substance can be absorbed into the body by inhalation, by ingestion and through the skin.Oral (L277)inhalation (L277)dermal (L277) |
| Toxicity summary | Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.orgExcess copper is sequestered within hepatocyte lysosomes, where it is complexed with metallothionein. Copper hepatotoxicity is believed to occur when the lysosomes become saturated and copper accumulates in the nucleus, causing nuclear damage. This damage is possibly a result of oxidative damage, including lipid peroxidation. Copper inhibits the sulfhydryl group enzymes such as glucose-6-phosphate 1-dehydrogenase, glutathione reductase, and paraoxonases, which protect the cell from free oxygen radicals. It also influences gene expression and is a co-factor for oxidative enzymes such as cytochrome C oxidase and lysyl oxidase. In addition, the oxidative stress induced by copper is thought to activate acid sphingomyelinase, which lead to the production of ceramide, an apoptotic signal, as well as cause hemolytic anemia. Copper-induced emesis results from stimulation of the vagus nerve. (L277, T49, A174, L280) |
| Average Daily Intake | The average daily intake of benzoic acid is 312 mg of which 278 mg is absorbed as sodium benzoate and 34 mg as benzoic acid(1). |
| Ecotoxicity excerpts | /AQUATIC SPECIES/ 0.5 mg/L of benzoic acid did not affect growth of blue-green alga, Anabaena flosaquae./AQUATIC SPECIES/ Lethal to goldfish in 7-96 hr at 200 mg/Llethal to orange spotted sunfish in 1 hr at 550-570 mg/L. /Conditions of bioassay not specified in source examined//AQUATIC SPECIES/ EC50/LC50 values (24-96 hr) for most of the other aquatic species tested (protozoa, molluscs, crustaceans, fish, amphibians) were in the range of 100-1291 mg/L. As seen with daphnids, the pH value of the test medium influences the toxicity of benzoic acid, which proved to be more toxic at lower pH levels./AQUATIC SPECIES/ Developmental toxicity effects seen in frog (Xenopus) embryos were craniofacial defects, especially microcephaly, and abnormal gut coiling.For more Ecotoxicity Excerpts (Complete) data for BENZOIC ACID (6 total), please visit the HSDB record page. |
| Signs and Symptoms | Sore throat. Cough.Redness. Swelling. Itching.Redness. Pain. Corneal damage.Abdominal pain. Nausea. Vomiting.Breathing high levels of copper can cause irritation of the nose and throat. Ingesting high levels of copper can cause nausea, vomiting, diarrhea, headache, dizziness, and respiratory difficulty. (L278, L279) |
| Atmospheric standards | This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Benzoic acid is produced, as an intermediate or a final product, by process units covered under this subpart. |
| CERCLA reportable quantities | Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2270 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b). |
| Clean Water Act requirements | Benzoic acid is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance. |
| State drinking water guidelines | (FL) Florida 28,000 ug/L(ME) Maine 28,000 ug/L(MN) Minnesota 30000 ug/L(NH) New Hampshire 28,000 ug/L |
| F | 21 |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Faceshields, Gloves |
| Water hazard class (WGK) | 1 |
| TSCA inventory status | TSCA listed |
| RTECS number | DG0875000 |
| UN transport number | UN 3077 9/PG 3 |
| Customs code | 2916 31 00 |
| Toxicity | LD50 orally in Rabbit: 1700 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
| Risk statements (R) | 22-36-42/43-36/37/38-40-63-43-23/24/25-45-41-37/38-20/21/22-48/23-38-67-37 |
| Signal word | Danger |
| GHS pictogram | GHS05,GHS08 |
| Hazard symbols | Xn,T,Xi |
| hazard_note | Harmful |
| Safety statements (S) | 26-45-37/39-24-22-36/37-24/25-23-53-36-63-39 |
| Hazard class | 9Eye Dam. 1Skin Irrit. 2STOT RE 1 Inhalation |
| Storage class | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Target organs | Lungs |
| GHS hazard statements | H315-H318-H372 |
| Limited quantities | 5.0 kg (11 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
| REACH registrations | Active |
| Autoignition temperature | 570 °C |
| GHS precautionary statements | P280-P302+P352-P305+P351+P338+P310-P314 |
| Hazardous substances data | 65-85-0(Hazardous Substances Data) |
Applications & Uses
Uses
1. Used as a chemical reagent and preservative. 2. Benzoic acid is important type food preservative. Under acidic conditions, It 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 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 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.Benzoic acid and its sodium salt are food preservatives. Under acidic conditions, it 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. 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.
Description
Benzoic acid is a colorless, crystalline solid also known as benzenecarboxylic acid. It is the simplest aromatic carboxylic acid, with a carboxyl group (-COOH) bonded directly to the benzene ring. It is found naturally in the benzoin resin of a number of plants.
Occurrence
Reported found in fresh apple, apricot (Prunus armeniaca L.), strawberry fruit, cherry (Prunus cerasus L.), butter, boiled and cooked beef, pork fat, white wine, black tea, green tea, fresh plum, mushroom, Bourbon vanilla (Vanilla planifolia Andrews), and other natural sources. Reported as being a constituent of various oils, resins and flower absolutes; hyacinth, tuberose, neroli bigarade, Chinese cinnamon, cinnamon leaves, anise, vertiver, ylang-ylang, Tolu balsam and clove; it is contained in fairly sizable amounts in gum benzoin, from which benzoic acid is extracted by sublimation.
History
Benzoic acid was first isolated from the dry distillation of benzoin by Blaise de Vigenère (1523–1596) in the 16th century. Friedrich Whler (1800–1882) and Justus von Liebig (1803–1873) prepared benzoic acid from oxidizing bitter almond oil (benzaldehyde) in 1832 and determined the formula for each of these compounds. They proposed that bitter almond oil, C7H6O, and benzoic acid were derivatives from the benzoyl radical, C7H5O; the radical theory was a major early theory in the development of organic chemistry.
Uses
Calorimetry Benzoic acid is the most commonly used chemical standard to determine the heat of capacity of a bomb calorimeter. Feed stock 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 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 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 in to the cell. Medicinal 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, 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. Benzoic acid was used as an expectorant, analgesic, and antiseptic in the early 20th century.
Uses
Sodium benzoate 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. Benzoic acid and sodium benzoate (C6H5COONa) are used as food preservatives and added to foods, juices, and beverages that are acidic.
General Description
Boric acid,H3B03, also known as boracic acid, orthoboric acid, and sassolite, is a white solid composed of triclinic crystals.It 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.
Preparation & Synthesis
Preparation
Industrial preparation method The industrial 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, it 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.
Preparation
By oxidation of toluene with nitric acid or sodium bichromate or from benzonitrile.