- Email: [email protected]
Acrylic Acid
Acrylates see Acrylic Acid; Ethyl Acrylate; Methyl Acrylate
Acrylic Acid D Brown, Manchester University College of Pharmacy, Fort Wayne, IN, USA Ó 2014 Elsevier Inc. All rights reserved. This article is a revision of the previous edition article by Sanjay Chanda & Harihara M. Mehendale, volume 1, pp 45–46, Ó 2005, Elsevier Inc. l
Name: Acrylic acid Chemical Abstracts Service Registry Number: 79-10-7 l Synonyms: Acroleic acid; Aqueous acrylic acid; Ethylene carboxylic acid; Glacial acrylic acid (98% in aqueous solution); 2-Propenoic acid l Molecular Formula: C3H4O2 l Chemical Structure: l
H2C O
OH
acid were released. It has been shown to be oxidized by both aerobic and anaerobic pathways.
Exposure and Exposure Monitoring Human exposure to acrylic acid is mainly to its vapors, and exposure is primarily confined to production processes as acrylic acid is used in the manufacturing of numerous acrylates. Levels of acrylic acid are monitored in samples by quantification using HPLC.
Background
Toxicokinetics
Acrylic acid, also known as prop-2-enoic acid, is an organic molecule with the formula C3H4O2, and is the simplest of the unsaturated carboxylic acids. At room temperature, acrylic acid is a colorless liquid with a tart or acrid smell. Industrially, acrylic acid is produced from the oxidation of propene with molecular oxygen. Acrylic acid is highly susceptible to Michaeltype reactions, and most of the uses of this chemical involve polymerization reactions. Acrylic acid is used to produce large quantities of acrylic esters.
The excretion half-life of acrylic acid has been found to be 40 min. Both in vitro and in vivo studies of acrylic acid metabolism have shown that it is extensively metabolized to 3-hydroxyproionic acid, carbon dioxide, and mercapturic acid, all of which are eliminated in expired air and urine. Because of its rapid metabolism, acrylic acid has no potential for bioaccumulation.
Mechanism of Toxicity Uses
Acrylic acid is corrosive, and its toxicity occurs at the site of contact.
Acrylic acid is used as a building block in the production of many types of homopolymeric and copolymeric materials, including various plastics, coatings, adhesives, elastomers, paints, and polishes. Additionally, acrylic acid is used in the production of hygienic medical products, detergents, and wastewater treatment chemicals.
Environmental Fate, Behavior, Routes, and Pathways Acrylic acid’s large-scale use and production results in its release into the environment. The most likely route of exposure is inhalation because acrylic acid has a low vapor pressure. The miscibility of acrylic acid in water combined with its low vapor pressure prevent it from accumulating in the soil. Acrylic acid that is emitted into the atmosphere is degraded photochemically by reaction with hydroxyl radicals. There is no potential for long-range atmospheric transport of acrylic acid because it has an atmospheric lifetime of 1 month. Acrylic acid rapidly oxidizes when added to water, so the potential to deplete oxygen exists if a large quantity of acrylic
74
Acute and Short-Term Toxicity Animal Although a wide range of LD50 values has been reported for acrylic acid, it is generally believed to possess low to moderate acute toxicity in the oral route, and moderate acute toxicity in the inhalation and dermal routes. Many of the symptoms of acute toxicity parallel those found in humans.
Human Acrylic acid is corrosive and irritating to the skin. Exposure to vapor can cause moderate to severe skin and eye irritation. Acrylic acid can also cause forestomach edema. Acute exposure is corrosive to the eyes, nose, throat, and mucous membranes of the upper respiratory and gastrointestinal tracts. Inhalation of vapors produces a burning sensation, cough, nasal discharge, sore throat, labored breathing, headache, nausea, vomiting, confusion, dizziness, and unconsciousness.
Encyclopedia of Toxicology, Volume 1
http://dx.doi.org/10.1016/B978-0-12-386454-3.00220-7
Acrylic Acid
Chronic Toxicity Animal Animals exposed to acrylic acid via chronic inhalation developed lethargy, weight loss, kidney abnormalities, and inflammation of the upper respiratory tract. Drinking water studies in rats showed a NOAEL of 140 mg kg 1 bw per day in decreased weight gain in a 12-month study and a NOAEL of 240 mg kg 1 bw per day for histopathological changes in the stomach. Inhalation studies demonstrated a LOAEL of 5 ppm in mice exposed to acrylic acid during 90 days, based on nasal lesions. Analogous studies in rats showed a LOAEL of 75 ppm.
75
should be maintained. Artificial respiration should be provided if breathing has stopped. Treatment is usually symptomatic.
Ecotoxicology
No reports of acrylic acid poisoning of the general public were found.
Acrylic acid is not thought to pose a threat to ecosystems because of its rapid oxidation to benign chemical species. Bioaccumulation of acrylic acid is low due to its low partition coefficient and rapid oxidation. No evidence of biomagnification of acrylic acid in the food chain was found. Algae have been found to be the most sensitive to acrylic acid of the aquatic organisms studied, with a noobserved-effect-concentration of 0.008 mg l 1. No studies were found regarding the toxicity of acrylic acid to terrestrial organisms.
Reproductive Toxicity
Exposure Standards and Guidelines
Rats injected with acrylic acid showed signs of teratogenic effects and embryotoxicity.
OSHA has currently set exposure limits for acrylic acid of 10 ppm for an 8-h TWA. However, these are not currently enforced by the agency. The National Institute for Occupational Safety and Health has recommended an exposure limit of 2 ppm for a 10-h TWA.
Human
Genotoxicity Both positive and negative results have been found in in vitro genotoxicity tests. An in vivo bone marrow chromosome aberration assay was negative.
Carcinogenicity The data available do not suggest that acrylic acid is carcinogenic; however, the existing data may be inadequate to conclude that it is not carcinogenic.
See also: Acrolein; Acrylamide; Acrylonitrile.
Further Reading Hellwig, J., Deckardt, K., Freisberg, K.O., 1993. Subchronic and chronic studies of the effects of oral administration of acrylic acid to rats. Food Chem. Toxicol. 3, 1–18. Klimisch, H.J., Hellwig, J., 1991. The prenatal inhalation toxicity of acrylic acid in rats. Fundam. Appl. Toxicol. 16, 656–666. Vodicka, P., Gut, I., Frantik, E., 1990. Effects of inhaled acrylic acid derivatives in rats. Toxicology 65, 209–221.
Clinical Management Relevant Websites Exposure should be terminated as soon as possible by moving the victim to fresh air. The skin, eyes, and mouth should be washed with copious amounts of water. Contaminated clothing should be removed and isolated. The victim should be kept calm and normal body temperature
http://www.osha.gov/dts/sltc/methods/organic/org028/org028.html http://www.epa.gov/ttn/atw/hlthef/acrylica.html http://www.inchem.org/documents/ehc/ehc/ehc191.htm
Acrylic Acid D Brown, Manchester University College of Pharmacy, Fort Wayne, IN, USA Ó 2014 Elsevier Inc. All rights reserved. This article is a revision of the previous edition article by Sanjay Chanda & Harihara M. Mehendale, volume 1, pp 45–46, Ó 2005, Elsevier Inc. l
Name: Acrylic acid Chemical Abstracts Service Registry Number: 79-10-7 l Synonyms: Acroleic acid; Aqueous acrylic acid; Ethylene carboxylic acid; Glacial acrylic acid (98% in aqueous solution); 2-Propenoic acid l Molecular Formula: C3H4O2 l Chemical Structure: l
H2C O
OH
acid were released. It has been shown to be oxidized by both aerobic and anaerobic pathways.
Exposure and Exposure Monitoring Human exposure to acrylic acid is mainly to its vapors, and exposure is primarily confined to production processes as acrylic acid is used in the manufacturing of numerous acrylates. Levels of acrylic acid are monitored in samples by quantification using HPLC.
Background
Toxicokinetics
Acrylic acid, also known as prop-2-enoic acid, is an organic molecule with the formula C3H4O2, and is the simplest of the unsaturated carboxylic acids. At room temperature, acrylic acid is a colorless liquid with a tart or acrid smell. Industrially, acrylic acid is produced from the oxidation of propene with molecular oxygen. Acrylic acid is highly susceptible to Michaeltype reactions, and most of the uses of this chemical involve polymerization reactions. Acrylic acid is used to produce large quantities of acrylic esters.
The excretion half-life of acrylic acid has been found to be 40 min. Both in vitro and in vivo studies of acrylic acid metabolism have shown that it is extensively metabolized to 3-hydroxyproionic acid, carbon dioxide, and mercapturic acid, all of which are eliminated in expired air and urine. Because of its rapid metabolism, acrylic acid has no potential for bioaccumulation.
Mechanism of Toxicity Uses
Acrylic acid is corrosive, and its toxicity occurs at the site of contact.
Acrylic acid is used as a building block in the production of many types of homopolymeric and copolymeric materials, including various plastics, coatings, adhesives, elastomers, paints, and polishes. Additionally, acrylic acid is used in the production of hygienic medical products, detergents, and wastewater treatment chemicals.
Environmental Fate, Behavior, Routes, and Pathways Acrylic acid’s large-scale use and production results in its release into the environment. The most likely route of exposure is inhalation because acrylic acid has a low vapor pressure. The miscibility of acrylic acid in water combined with its low vapor pressure prevent it from accumulating in the soil. Acrylic acid that is emitted into the atmosphere is degraded photochemically by reaction with hydroxyl radicals. There is no potential for long-range atmospheric transport of acrylic acid because it has an atmospheric lifetime of 1 month. Acrylic acid rapidly oxidizes when added to water, so the potential to deplete oxygen exists if a large quantity of acrylic
74
Acute and Short-Term Toxicity Animal Although a wide range of LD50 values has been reported for acrylic acid, it is generally believed to possess low to moderate acute toxicity in the oral route, and moderate acute toxicity in the inhalation and dermal routes. Many of the symptoms of acute toxicity parallel those found in humans.
Human Acrylic acid is corrosive and irritating to the skin. Exposure to vapor can cause moderate to severe skin and eye irritation. Acrylic acid can also cause forestomach edema. Acute exposure is corrosive to the eyes, nose, throat, and mucous membranes of the upper respiratory and gastrointestinal tracts. Inhalation of vapors produces a burning sensation, cough, nasal discharge, sore throat, labored breathing, headache, nausea, vomiting, confusion, dizziness, and unconsciousness.
Encyclopedia of Toxicology, Volume 1
http://dx.doi.org/10.1016/B978-0-12-386454-3.00220-7
Acrylic Acid
Chronic Toxicity Animal Animals exposed to acrylic acid via chronic inhalation developed lethargy, weight loss, kidney abnormalities, and inflammation of the upper respiratory tract. Drinking water studies in rats showed a NOAEL of 140 mg kg 1 bw per day in decreased weight gain in a 12-month study and a NOAEL of 240 mg kg 1 bw per day for histopathological changes in the stomach. Inhalation studies demonstrated a LOAEL of 5 ppm in mice exposed to acrylic acid during 90 days, based on nasal lesions. Analogous studies in rats showed a LOAEL of 75 ppm.
75
should be maintained. Artificial respiration should be provided if breathing has stopped. Treatment is usually symptomatic.
Ecotoxicology
No reports of acrylic acid poisoning of the general public were found.
Acrylic acid is not thought to pose a threat to ecosystems because of its rapid oxidation to benign chemical species. Bioaccumulation of acrylic acid is low due to its low partition coefficient and rapid oxidation. No evidence of biomagnification of acrylic acid in the food chain was found. Algae have been found to be the most sensitive to acrylic acid of the aquatic organisms studied, with a noobserved-effect-concentration of 0.008 mg l 1. No studies were found regarding the toxicity of acrylic acid to terrestrial organisms.
Reproductive Toxicity
Exposure Standards and Guidelines
Rats injected with acrylic acid showed signs of teratogenic effects and embryotoxicity.
OSHA has currently set exposure limits for acrylic acid of 10 ppm for an 8-h TWA. However, these are not currently enforced by the agency. The National Institute for Occupational Safety and Health has recommended an exposure limit of 2 ppm for a 10-h TWA.
Human
Genotoxicity Both positive and negative results have been found in in vitro genotoxicity tests. An in vivo bone marrow chromosome aberration assay was negative.
Carcinogenicity The data available do not suggest that acrylic acid is carcinogenic; however, the existing data may be inadequate to conclude that it is not carcinogenic.
See also: Acrolein; Acrylamide; Acrylonitrile.
Further Reading Hellwig, J., Deckardt, K., Freisberg, K.O., 1993. Subchronic and chronic studies of the effects of oral administration of acrylic acid to rats. Food Chem. Toxicol. 3, 1–18. Klimisch, H.J., Hellwig, J., 1991. The prenatal inhalation toxicity of acrylic acid in rats. Fundam. Appl. Toxicol. 16, 656–666. Vodicka, P., Gut, I., Frantik, E., 1990. Effects of inhaled acrylic acid derivatives in rats. Toxicology 65, 209–221.
Clinical Management Relevant Websites Exposure should be terminated as soon as possible by moving the victim to fresh air. The skin, eyes, and mouth should be washed with copious amounts of water. Contaminated clothing should be removed and isolated. The victim should be kept calm and normal body temperature
http://www.osha.gov/dts/sltc/methods/organic/org028/org028.html http://www.epa.gov/ttn/atw/hlthef/acrylica.html http://www.inchem.org/documents/ehc/ehc/ehc191.htm