Benzilic acid

White to tan powder

Forms monoclinic needles from water

Changes to deep red color at higher temperature

Very soluble in ethanol, ethyl ether; soluble concentrated sulfuric acid; slightly soluble in acetone

In water, 1.41X10+3 mg/L at 25 °C

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 50 reports by companies from 2 notifications to the ECHA C&L Inventory.

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

Chemical: Benzeneacetic acid, .alpha.-hydroxy-.alpha.-phenyl-

Status: Active Update: 09-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25901

Benzeneacetic acid, .alpha.-hydroxy-.alpha.-phenyl-: Does not have an individual approval but may be used under an appropriate group standard

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. Benzilic acid is produced, as an intermediate or a final product, by process units covered under this subpart.

Acute Tox. 4 (100%)

Acute toxicity (Oral) - Category 4

Wear self contained breathing apparatus for fire fighting if necessary.

Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Accidental Release Measures. Personal precautions - Use personal protective equipment, avoid dust formation, avoid breathing dust, ensure adequate ventilation. Environmental precautions - Do not let product enter drains. Methods for cleaning up - Pick up and arrange disposal without creating dust. Keep in suitable, closed containers for disposal.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

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.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit 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.

Handling: Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection. Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.

In case of skin contact, wash off with soap and plenty of water.

Where risk assessment shows air-purifying respirators are appropriate use a dust mask type N95 (US) or type P1 (EN 143) respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Safety glasses for eye protection

Handle with gloves. For prolonged or repeated contact use protective gloves.

Choose body protection according to the amount and concentration of the dangerous substance at the work place.

/The Chemical Weapons Convention (CWC) is an international treaty which bans the development, production, stockpiling, and transfer or use of chemical weapons. The Convention mandates the destruction and prohibition of chemical weapons and related facilities and provides for restrictions on international trade in toxic chemicals and precursors./ The Convention's monitoring and verification measures involve submission of declarations regarding ... /Schedule 1, 2, and 3 chemicals/ and inspections by the Organization for the Prohibition of Chemical Weapons of the facilities where these chemicals are produced. ... Schedule 2 lists toxic chemicals and precursors deemed to pose a significant risk to the object and purpose of the CWC because of their lethal or incapacitating properties. Precursors may be used in the final stage for formation, or may be important for the production, of any of the chemicals listed in Schedule 1 or toxic chemicals listed in Schedule 2. Schedule 2 chemicals are not produced in large quantities for commercial ... purposes ... but may be used to manufacture such things as insecticides, herbicides, lubricants or pharmaceutical products (2). 2,2-Diphenyl-2-hydroxyacetic acid is listed in the CWC Annex on Chemicals under Schedule 2 (1).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 420(SRC), determined from a log Kow of 2.30(2) and a regression-derived equation(3), indicates that benzilic acid is expected to have moderate mobility in soil(SRC). The pKa of benzilic acid is 3.05(4), indicating that this compound will exist almost entirely exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization from moist soil is not expected because the acid exists as an anion and anions do not volatilize. Benzilic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.3X10-8 mm Hg(SRC), determined from a fragment constant method(6). A theoretical BOD of 0% in the Japanese MITI test(7) indicates that biodegradation is not an important fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 420(SRC), determined from a log Kow of 2.30(2), and a regression-derived equation(3), indicates that benzilic acid is expected to adsorb moderately to suspended solids and sediment(SRC). A pKa of 3.05(4) indicates benzilic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(5). According to a classification scheme(6), an estimated BCF of 3.2(SRC), determined from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A theoretical BOD of 0% in the Japanese MITI test(8) indicates that biodegradation is not 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), benzilic acid, which has an estimated vapor pressure of 2.3X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase benzilic acid may be removed from the air by wet or dry deposition(SRC). Benzilic acid does not contain chromophores that absorb at wavelengths >290 nm(3) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

The Koc of benzilic acid is estimated as 420(SRC), using a log Kow of 2.30(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that benzilic acid is expected to have moderate mobility in soil. The pKa of benzilic acid is 3.05(4), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5).

A BCF of <0.2 was measured in fish for benzilic acid at a concentration of 1 ppm using carp(Cyprinus carpio) which were exposed over an 6-week period(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The pKa of benzilic acid is 3.05(1), indicating that benzilic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(2). Benzilic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.3X10-8 mm Hg(SRC), determined from a fragment constant method(3).

Benzilic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). Benzilic acid does not contain chromophores that absorb at wavelengths >290 nm(1) and therefore is not susceptible to direct photolysis by sunlight(SRC).

Occupational exposure to benzilic acid may occur through inhalation of dust and dermal contact at workplaces where benzilic acid is produced or used. Limited exposure to the general population may occur due to its use as an intermediate in synthesis of the anticholinergic drug, clidinium bromide, an anticholinergic. (SRC)

Benzilic acid's production and use as a precursor in the production of chemical warfare agent 3-quinuclidinyl benzilate may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 2.3X10-8 mm Hg at 25 °C indicates benzilic acid will exist solely in the particulate phase in the atmosphere. Particulate phase benzilic acid will be removed from the atmosphere by wet or dry deposition. Benzilic acid does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight. If released to soil, benzilic acid is expected to have moderate mobility based upon an estimated Koc of 420. The pKa of benzilic acid is 3.05, indicating that this compound will exist almost entirely in the anionic form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts. Volatilization from moist soil is not expected because the acid exists as an anion and anions do not volatilize. A 0% of theoretical BOD in the Japanese MITI test indicates that biodegradation is not an important fate process. If released into water, benzilic acid is expected to adsorb moderately to suspended solids and sediment based upon a Koc of 420. The pKa indicates benzilic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. A BCF of <0.2 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to benzilic acid may occur through inhalation of dust and dermal contact at workplaces where benzilic acid is produced or used. Limited exposure to the general population may occur due to its use as an intermediate in synthesis of the drug clidinium bromide, an anticholinergic. (SRC)

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Organic acids and related compounds/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/

LD50 Mouse sc 1300 mg/kg

LD50 Mouse oral 2 g/kg /2,000 mg/kg/

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. Benzilic acid is produced, as an intermediate or a final product, by process units covered under this subpart.

Used to make 3-quinuclidinyl benzilate (chemical warfare agent) and clidinium bromide (anticholinergic drug); [HSDB]

Precursor in the synthesis of the chemical warfare agent 3-quinuclidinyl benzilate (BZ)

Used in the synthesis of the anticholinergic drug clidinium bromide

Prepared from benzil by the action of concentrated aqueous or alc KOH

Synthesis: Benzoin, nitric acid, ethanol, NaOH, and water.