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Acrylamide

Acrylamide structure

Acrylamide 

structure
  • CAS No:

    79-06-1

  • Formula:

    C3H5NO

  • Chemical Name:

    Acrylamide

  • Synonyms:

    ETHYLENECARBOXAMIDE;ACRYLAMIDE 2K;ACRYLAMIDE 4K;ACRYLAMIDE-HG;ACRYLAMIDE HGX;ACRYLAMIDE MONOMER;ACRYL-40(TM);ACRYLIC ACID AMIDE

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

Acrylamide is odorless and colorless crystal. It is soluble in water, ethanol, acetone, ether, and methyl chloroform, and slightly soluble in toluene but insoluble in benzene. Acrylamide is a water-soluble monomer with two reactive centers (a vinyl group - with its reactive double bond, and an amide group). Because of its high reactivity, aqueous acrylamide monomer is stabilized with dissolved cupric salts and oxygen to prevent polymerization during shipping and storage. Acrylamide, in monomeri


Acrylamide is an odorless, white crystalline solid that initially was produced for commercial purposes by reaction of acrylonitrile with hydrated sulfuric acid.Acrylamide exists in two forms: a monomer and a polymer. Monomer acrylamide readily participates in radicalinitiated polymerization reactions, whose products form the basis of most of its industrial applications. The single unit form of acrylamide is toxic to the nervous system, a carcinogen in laboratory animals and a suspected carcinogen in humans. The multiple unit or polymeric form is not known to be toxic.Acrylamide is formed as a by-product of the Maillard reaction. The Maillard reaction is best known as a reaction that produces pleasant flavor, taste, and golden color in fried and baked foods; the reaction occurs between amines and carbonyl compounds, particularly reducing sugars and the amino acid asparagine. In the first step of the reaction, asparagine reacts with a reducing sugar, forming a Schiff’s base. From this compound, acrylamide is formed following a complex reaction pathway that includes decarboxylation and a multistage elimination reaction. Acrylamide formation in bakery products, investigated in a model system, showed that free asparagine was a limiting factor. Treatment of flours with asparaginase practically prevented acrylamide formation. Coffee drinking and smoking are other major sources apart from the human diet.


Acrylamide, in monomeric form, is an odorless, flake-like crystals which sublime slow at room temperature. May be dissolved in a flammable liquid.


ChEBI: A member of the class of acrylamides that results from the formal condensation of acrylic acid with ammonia.


acrylamide: An inert gel (polyacrylamide)employed as a medium inelectrophoresis. It is used particularlyin the separation of macromolecules,such as nucleic acids and proteins.

Acrylamide Basic Attributes

71.08

71.08

605349

201-173-7

TSCA listed

White

29241900

Characteristics

43.09000

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.

0.358

White crystals

1,322 g/cm3

82-86 °C(lit.)

125 °C25 mm Hg(lit.)

138 °C

1.460

Acrylamide is routinely tested at 250 mg/mL in water, giving a clear colorless solution. It is soluble at least to 40% (w/v) in water, and reportedly up to 215 g/100 mL in water at 30°C.

Storage Room low temperature ventilation drying ,Separate storage with oxidizing agent, acid, food and chemical additive

0.03 mm Hg ( 40 °C)

2.45 (vs air)

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.

The volatility of acrylamide is low (0.03 mmHg at 40 °C), and it does not pose a significant flammability hazard.

A VIOLENT EXPLOSION OCCURRED DURING COMMON LAB PROCEDURE OF DISSOLVING ELECTROPHORESIS POLYACRYLAMIDE GELS WITH H2O2, IN ORDER TO MEASURE RADIOACTIVE SPECIES BY SCINTILLATION COUNTING.

Odorless solid

5.0-7.0 (50g/l, H2O, 20℃)

15.35±0.50(Predicted)

(x 10-9atmm3/mol): 3.03 at 20 °C (approximate - calculated from water solubility and vapor pressure)

Acrylamide is very soluble in water. The solvent is not necessarily water soluble.

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].

424°C

2-8°C

Safety Information

III

6.1

UN 3426 6.1/PG 3

3

T

53-45-24-36/37/39-26-36/37

AS3325000

T

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.

Unstable. Do not heat above 50C. Explosive. Incompatible with acids, bases, oxidizing agents, reducing agents, iron and iron salts, copper, aluminium, brass, free radical initiators. Air sensitive. Hygroscopic.

P201-P261-P280-P304 + P340 + P312-P305 + P351 + P338-P308 + P313

45-46-20/21-25-36/38-43-48/23/24/25-62-48/20/21/22-22-24/25

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.

UN 2074 6.1/PG III (ACRYLAMIDE, SOLID)

Acrylamide is used in the plastic polymers industry for water treatments and soil stabilization and to prepare polyacrylamide gels for electrophoresis. This neurotoxic, carcinogenic, and genotoxic substance is known to have caused contact dermatitis in industrial and laboratory workers

Toxicity

Potential occupational carcinogen. NIOSH REL: TWA 0.03, IDLH: 60; OSHA PEL: TWA 0.3; ACGIH TLV: TWA 0.03.

Drug Information

The acute toxicity of acrylamide is moderate by ingestion or skin contact. Skin exposure leads to redness and peeling of the skin of the palms. Aqueous acrylamide solutions cause eye irritation; exposure to a 50% solution of acrylamide caused slight corneal injury and slight conjunctival irritation, which healed in 8 days. The chronic toxicity of acrylamide is high. Repeated exposure to ~2 mg/kg per day may result in neurotoxic effects, including unsteadiness, muscle weakness, and numbness in the feet (leading to paralysis of the legs), numbness in the hands, slurred speech, vertigo, and fatigue. Exposure to slightly higher repeated doses in animal studies has induced multisite cancers and reproductive effects, including abortion, reduced fertility, and mutagenicity. Acrylamide is listed in IARC Group 2B ("possible human carcinogen") and is classified as a "select carcinogen" under the criteria of the OSHA Laboratory Standard.

Acrylamide Use and Manufacturing

Methods of Manufacturing

1. Acrylonitrile sulfuric acid hydration: acrylonitrile and water in the presence of sulfuric acid hydrolysis into acrylamide sulfate, and then neutralized with liquid ammonia to produce acrylamide solution and ammonium sulfate, the reactant after separation and filtration, the filtrate crystallization, drying Have finished. The disadvantage of this method is the by-product of a large number of low-value ammonium sulfate, and there are serious problems such as sulfuric acid corrosion and pollution. Per ton of acrylamide by-product of ammonium sulfate 2280kg. Raw material consumption quota: acrylonitrile (100%) 980kg / t, sulfuric acid (100%) 200kg / t, ammonia (100%) 700kg / t.
2. Acrylonitrile direct hydration: acrylonitrile and water in the presence of copper catalyst, 85-125 ℃ and 0.3-0.4MPa pressure directly derived from hydration. The method of aqueous acrylamide solution (containing only a small amount of by-products), can be directly sold as a product, to avoid acrylamide dust pollution, with water solution is beneficial to labor protection. Product reference specifications: the appearance of white scaly or powder. Grade content ≥ 95%; second grade content ≥ 90%; third grade content ≥ 85%.
3. Enzymatic catalysis: the aqueous solution of acrylonitrile at room temperature into a fixed bed reactor equipped with bacteria catalyst, the reaction of acrylonitrile 100% conversion to acrylamide. By separation, or even without purification, concentration of acrylamide to get the industrial products.

Uses

Acrylamide (or acrylic amide) is a chemical compound with the chemical formula C3H5NO. Its IUPAC name is prop-2-enamide. It is a white odorless crystalline solid, soluble in water, ethanol, ether, and chloroform. Acrylamide decomposes in the presence of acids, bases, oxidizing agents, iron, and iron salts. It decomposes non-thermally to form ammonia, and thermal decomposition produces carbon monoxide, carbon dioxide, and oxides of nitrogen.Acrylamide can be prepared by the hydrolysis of acrylonitrile by nitrile hydratase. In industry, most acrylamide is used to synthesize polyacrylamides, which find many uses as water-soluble thickeners. These include use in wastewater treatment, gel electrophoresis (SDS-PAGE), papermaking, ore processing, tertiary oil recovery, and the manufacture of permanent press fabrics. Some acrylamide is used in the manufacture of dyes and the manufacture of other monomers.The discovery of acrylamide in some cooked starchy foods in 2002 prompted concerns about the carcinogenicity of those foods. As of 2014 it is still not clear whether acrylamide consumption affects people's risk of developing cancer.Acrylamide is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.


Acrylamide contained in polyacrylamide gels used for electrophoresis caused contact dermatitis in laboratory workers.


In the production of polyacrylamides, which are used in water and waste treatment, paper and pulp processing, cosmetic additives, and textile processing; in adhesives and grouts; as cross-linking agents in vinyl polymers

Computed Properties

Molecular Weight:71.08
XLogP3:-0.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:71.037113783
Monoisotopic Mass:71.037113783
Topological Polar Surface Area:43.1
Heavy Atom Count:5
Complexity:57.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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  • Data: 2026-07-16
  • Price: 13225.00Yuan/mt
  • Change: 0

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