Ethyl acrylate
Encyclopedia
Ethyl acrylate is an organic compound
primarily used in the preparation of various polymer
s. It is a clear liquid with an acrid penetrating odor. The human nose is capable of detecting this odor at a thousand times lower concentration than is considered harmful if continuously exposed for some period of time.
can be reacted with ethanol
using sulfuric acid
as a catalyst to produce ethyl acrylate. It may also be prepared from acetylene
, carbon monoxide
and ethanol.
Ethyl acrylate will readily polymerize upon standing and polymerization is accelerated by heat, light, and peroxide
s.
Although there are some reports claiming that ethyl acrylate is a carcinogen
, major respected bodies regard the evidence of human carcinogenicity as weak and/or inconsistent. The International Agency for Research on Cancer
stated, "Overall evaluation, Ethyl acrylate is possibly carcinogenic to humans (Group 2B)." The United States Environmental Protection Agency
(EPA) states, "Human studies on occupational exposure to ethyl acrylate... have suggested a relationship between exposure to the chemical(s) and colorectal cancer, but the evidence is conflicting and inconclusive. In a study by the National Toxicology Program (NTP), increased incidences of squamous cell papilloma
s and carcinomas of the forestomach were observed in rats and mice exposed via gavage (experimentally placing the chemical in the stomach). However, the NTP recently determined that these data were not relevant to human carcinogenicity and removed ethyl acrylate from its list of carcinogens." (Occupational exposure generally involves exposure that occurs regularly, over an extended period of time.)
Ethyl acrylate can irritate the nose, throat and lungs.
One favorable safety aspect is that ethyl acrylate has good warning properties; the odor threshold
is much lower than any level of health concern. In other words, the bad odor warns people of ethyl acrylate's presence long before the concentration reaches a level capable of creating a serious health risk. Reports of the exact levels vary somewhat, but, for example, the U.S. E.P.A. reports an odor threshold of 0.0012 parts per million (ppm), but the E.P.A.'s lowest level of health concern, the Acute Exposure Guideline Level-1 (AEGL-1) is 8.3 ppm, which is almost 7000 times the odor threshold.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
primarily used in the preparation of various polymer
Polymer
A polymer is a large molecule composed of repeating structural units. These subunits are typically connected by covalent chemical bonds...
s. It is a clear liquid with an acrid penetrating odor. The human nose is capable of detecting this odor at a thousand times lower concentration than is considered harmful if continuously exposed for some period of time.
Chemistry
Ethyl acrylate can be prepared by several industrial methods. AcrylonitrileAcrylonitrile
Acrylonitrile is the chemical compound with the formula C3H3N. This pungent-smelling colorless liquid often appears yellow due to impurities. It is an important monomer for the manufacture of useful plastics. In terms of its molecular structure, it consists of a vinyl group linked to a nitrile...
can be reacted with ethanol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...
using sulfuric acid
Sulfuric acid
Sulfuric acid is a strong mineral acid with the molecular formula . Its historical name is oil of vitriol. Pure sulfuric acid is a highly corrosive, colorless, viscous liquid. The salts of sulfuric acid are called sulfates...
as a catalyst to produce ethyl acrylate. It may also be prepared from acetylene
Acetylene
Acetylene is the chemical compound with the formula C2H2. It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is unstable in pure form and thus is usually handled as a solution.As an alkyne, acetylene is unsaturated because...
, carbon monoxide
Carbon monoxide
Carbon monoxide , also called carbonous oxide, is a colorless, odorless, and tasteless gas that is slightly lighter than air. It is highly toxic to humans and animals in higher quantities, although it is also produced in normal animal metabolism in low quantities, and is thought to have some normal...
and ethanol.
Ethyl acrylate will readily polymerize upon standing and polymerization is accelerated by heat, light, and peroxide
Peroxide
A peroxide is a compound containing an oxygen–oxygen single bond or the peroxide anion .The O−O group is called the peroxide group or peroxo group. In contrast to oxide ions, the oxygen atoms in the peroxide ion have an oxidation state of −1.The simplest stable peroxide is hydrogen peroxide...
s.
Uses
Ethyl acrylate is used in the production of polymers including resins, plastics, rubber, and denture material.Human Health & Safety
Ethyl acrylate's main safety issue arises from its being flammable and highly reactive.Although there are some reports claiming that ethyl acrylate is a carcinogen
Carcinogen
A carcinogen is any substance, radionuclide, or radiation that is an agent directly involved in causing cancer. This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes...
, major respected bodies regard the evidence of human carcinogenicity as weak and/or inconsistent. The International Agency for Research on Cancer
International Agency for Research on Cancer
The International Agency for Research on Cancer is an intergovernmental agency forming part of the World Health Organisation of the United Nations....
stated, "Overall evaluation, Ethyl acrylate is possibly carcinogenic to humans (Group 2B)." The United States Environmental Protection Agency
United States Environmental Protection Agency
The U.S. Environmental Protection Agency is an agency of the federal government of the United States charged with protecting human health and the environment, by writing and enforcing regulations based on laws passed by Congress...
(EPA) states, "Human studies on occupational exposure to ethyl acrylate... have suggested a relationship between exposure to the chemical(s) and colorectal cancer, but the evidence is conflicting and inconclusive. In a study by the National Toxicology Program (NTP), increased incidences of squamous cell papilloma
Squamous cell papilloma
A Squamous cell papilloma is a generally benign papilloma that arises from the stratified squamous epithelium of the skin, lip, oral cavity, tongue, pharynx, larynx, esophagus, cervix, vagina or anal canal...
s and carcinomas of the forestomach were observed in rats and mice exposed via gavage (experimentally placing the chemical in the stomach). However, the NTP recently determined that these data were not relevant to human carcinogenicity and removed ethyl acrylate from its list of carcinogens." (Occupational exposure generally involves exposure that occurs regularly, over an extended period of time.)
Ethyl acrylate can irritate the nose, throat and lungs.
One favorable safety aspect is that ethyl acrylate has good warning properties; the odor threshold
Odor detection threshold
The odor detection threshold is the lowest concentration of a certain odor compound that is perceivable by the human sense of smell. The thresholds of a chemical compound is determined in part by its shape, polarity, partial charges and molecular mass...
is much lower than any level of health concern. In other words, the bad odor warns people of ethyl acrylate's presence long before the concentration reaches a level capable of creating a serious health risk. Reports of the exact levels vary somewhat, but, for example, the U.S. E.P.A. reports an odor threshold of 0.0012 parts per million (ppm), but the E.P.A.'s lowest level of health concern, the Acute Exposure Guideline Level-1 (AEGL-1) is 8.3 ppm, which is almost 7000 times the odor threshold.