Definition
ChEBI: A member of the class of acrylamides that results from the formal condensation of acrylic acid with ammonia.
General Description
A solution of a colorless crystalline solid. Flash point depends on the solvent but below 141°F. Less dense than water. Vapors heavier than air. Toxic oxides of nitrogen produced during combustion. Used for sewage and waste treatment, to make dyes and adhesives.
Reactivity Profile
ACRYLAMIDE SOLUTION reacts with azo and diazo compounds to generate toxic gases. Flammable gases are formed with strong reducing agents. Combustion generates mixed oxides of nitrogen (NOx). Spontaneous, violent polymerization occurs at the melting point (86°C of the undissolved solid [Bretherick, 5th ed., 1995, p. 428].
Air & Water Reactions
Acrylamide is very soluble in water. The solvent is not necessarily water soluble.
Health Hazard
Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
Potential Exposure
Added to water during sewage/wastewater treatment. Used in the manufacture of plastics, resins, rubber, synthetic textiles; as a dye, pigment. A major application for monomeric acrylamide is in the production of polymers as polyacrylamides. Polyacrylamides are used for soil stabilization, gel chromatography, electrophoresis, papermaking strengtheners, clarifications, and treatment of potable water and foods.
First aid
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately. If thischemical contacts the skin, flush with water immediately. If a person breathes in large amounts of this chemical, move the exposed person to fresh air at once and perform artificial respiration. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.
Shipping
UN2074 Acrylamide, Hazard Class: 6.1; Labels: 6.1-Poisonous materials
Incompatibilities
Acrylamide may decompose with heat and polymerize at temperatures above 84 C, or exposure to light, releasing ammonia gas. Reacts violently with strong oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Reacts with reducing agents; peroxides, acids, bases, and vinyl polymerization initiators. Fine particles of dust form explosive mixture with air.
Waste Disposal
Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Acrylamide residue and sorbent material may be packaged in epoxy-lined drums and taken to an EPAapproved disposal site. Incineration with provisions for scrubbing of nitrogen oxides from flue gases. Deep well injection.
Preparation
The principal synthetic route to making acrylamide involves the hydration of acrylonitrile (ACRN). In this process an aqueous ACRN solution reacts over a copper-oxide-chromium oxide catalyst at approximately 100°C. Several other catalyst systems have been used, and most of them contain copper - in some form. The reaction step is followed by purification and concentration to a 50% solution in a vacuum evaporator. The yield of acrylamide from ACRN is 98%. The purification and concentration steps are costly and also involve the recycle of ACRN back to the reaction step. In the early part of the new century, a catalytic distillation process has been developed that converts almost 100% of the ACRN to acrylamide and allows concentration to occur in the same column where acrylamide is made. Therefore this process is less costly.
Nitto Chemical (now Dia-Nitrix) introduced a biosynthetic route from ACRN to acrylamide in Japan in 1985. This process uses an immobilized nitrile hydratase biocatalyst that converts the ACRN solution to acrylamide with a yield of 99.5%. This high yield allows a concentrated acrylamide solution to be made without the need for ACRN recycle or solution concentration. This process therefore has lower energy costs.
Flammability and Explosibility
The volatility of acrylamide is low (0.03 mmHg at 40 °C), and it does not pose a
significant flammability hazard.
Chemical Reactivity
Reactivity with Water No reaction; Reactivity with Common Materials: Data not available; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: May occur at temperature above 50°C (120°F); Inhibitor of Polymerization: Oxygen (air) plus 50 ppm of copper as copper sulfate.
Biochem/physiol Actions
Acrylamide is a reactive, water soluble vinyl monomer. It causes a decrease in the number of neuritis per cell as well as reduces the rate of protein synthesis.
Carcinogenicity
Acrylamide is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Environmental Fate
Biological. Bridié et al. (1979) reported BOD and COD values of 0.05 and 1.33 g/g using
filtered effluent from a biological sanitary waste treatment plant. These values were determined
using a standard dilution method at 20 °C for a period of 5 d. When a sewage seed was used in a
separate screening test, a BOD value of 0.92 g/g was obtained. In a treatment plant, a BOD value
of 0.40 g/g was reported after 10 d (Mills et al., 1953). The ThOD for acrylamide is 1.35 g/g.
Soil. Under aerobic conditions, acrylamide degraded to ammonium ions which oxidized to
nitrite ions and nitrate ions. The ammonium ions produced in soil may volatilize as ammonia or
accumulate as nitrite ions in sandy or calcareous soils (Abdelmagid and Tabatabai, 1982).
Chemical/Physical. Readily polymerizes at the melting point or under UV light. In the presence
of alkali, polymerization is a violent reaction. On standing, may turn to yellowish color (Windholz
et al., 1983).
storage
In
particular, this substance should be handled only when wearing appropriate
impermeable gloves to prevent skin contact, and all operations that have the
potential of producing acrylamide dusts or aerosols of solutions should be conducted
in a fume hood to prevent exposure by inhalation.
Purification Methods
Crystallise acrylamide from acetone, chloroform, ethyl acetate, methanol or *benzene/chloroform mixture, then vacuum dry and store it in the dark under vacuum. Recrystallise it from CHCl3 by dissolving 200g in 1L, heating to boiling and filtering without suction in a warmed funnel through Whatman 541 filter paper; allowing to cool to room temperature and keeping at -15o overnight. The crystals are collected with suction in a cooled funnel and washed with 300mL of cold MeOH. The crystals are air-dried in a warm oven. [Dawson et al. Data for Biochemical Research, Oxford Press 1986 p. 449, Beilstein 2 IV 1471.] CAUTION: Acrylamide is extremely TOXIC (neurotoxic), and precautions must be taken to avoid skin contact or inhalation. Use gloves and handle in a well-ventilated fume cupboard.
Toxicity evaluation
All acrylamide in the environment is synthetic, the main source
being the release of the monomer residues from polyacrylamide
used in water treatment or in industry. Products
and compounds containing polyacrylamide can serve as sources
of exposure to residues of acrylamide.
