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HomeProduct name listAcrylamide

Acrylamide

Synonym(s):2-Propenamide;Acrylamide;Acrylic acid amide;Prop-2-enamide

  • CAS NO.:79-06-1
  • Empirical Formula: C3H5NO
  • Molecular Weight: 71.08
  • MDL number: MFCD00008032
  • EINECS: 201-173-7
  • Update Date: 2023-09-08 21:17:32
Acrylamide Structural Picture

What is Acrylamide?

Description

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.

Description

Acrylamide is the simplest unsaturated organic amide. Despite its low molar mass, and because it is highly polar, it is a solid rather than a liquid. As the hazard information table indicates, it is extremely toxic in multiple ways.
In 1949, Otto Bayer at Bayer AG (Leverkusen, West Germany) described the preparation of acrylamide. (Bayer was not related to the founding Bayer family.) Chemist Bayer synthesized acrylamide via the acid-catalyzed hydrolysis of acrylonitrile. This is the only manufacturing method in use today. But in 2019, Kemira Ltd. (Helsinki, Finland) announced that it will begin to produce biobased acrylamide in its Mobile, AL, plant.
By far the major use of acrylamide is polymerization into polyacrylamides, which, depending on their molar masses and degree of cross-linking, are valuable for flocculating solids suspended in water, thickening water for use in enhanced petroleum recovery, and agricultural soil conditioning.
Acrylamide has become notorious in the past 20 years because traces of it have been found in commercial and home-cooked foods. Most of these are starchy foods such as French fries, potato chips, and some breads. In general, higher temperatures and longer cooking times increase the formation of acrylamide. Smoking tobacco, however, results in much higher blood acrylamide concentrations than any food source.

The Uses of Acrylamide

Over 90% of acrylamide is used to make polyacrylamides (PAMs), and the remaining 10% is used to make N-methylolacrylamide (NMA) and other monomers. Water treatment PAMs consumed 60% of the acrylamide; PAMs for pulp and paper production consume 20% of the acrylamide; and PAMs for mineral processing consume 10% of the acrylamide. Some of the specific uses of acrylamide are:
In liquid-solid separation where acrylamide polymers act as flocculants and aids in mineral processing, waste treatment and water treatment. They also help reduce sludge volumes in these applications.
As additives in the manufacture of paper and paper board products, leather and paint industries. In the paper industry PAMs act as retention aids during wet end processing and in wet strength additives.
In the manufacture of synthetic resins for pigment binders for textile/leather industries, and In enhanced oil recovery.
use in protein electrophoresis (PAGE), synthesis of dyes and copolymers for contact lenses. It is reasonably anticipated to be a hum an carcinogen.

What are the applications of Application

Acrylamide Solution, 40% is commonly used matrix for electrophoretic separation of nucleic acids and proteins

What are the applications of Application

Acrylamide is a highly toxic, but commonly used matrix for electrophoretic separation of nucleic acids and proteins

Properties of Acrylamide

Melting point: 82-86 °C(lit.)
Boiling point: 125 °C25 mm Hg(lit.)
Density  1,322 g/cm3
Flash point: 138 °C
storage temp.  2-8°C
solubility  2040 g/L (25°C)
form  powder
appearance white crystals
color  White
Odor Odorless solid
Water Solubility  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.
Sensitive  Light Sensitive

Safety information for Acrylamide

Signal word Danger
Pictogram(s)

Skull and Crossbones
Acute Toxicity
GHS06

Health Hazard
GHS08
GHS Hazard Statements H301:Acute toxicity,oral
H315:Skin corrosion/irritation
H317:Sensitisation, Skin
H319:Serious eye damage/eye irritation
H340:Germ cell mutagenicity
H350:Carcinogenicity
H372:Specific target organ toxicity, repeated exposure
Precautionary Statement Codes P202:Do not handle until all safety precautions have been read and understood.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Acrylamide

InChIKey HRPVXLWXLXDGHG-UHFFFAOYSA-N

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