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
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 |
Abamectin manufacturer
PAARICHEM RESOURCES LLP
JSK Chemicals
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