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Acrylamide is a chemical that naturally forms in starchy food products during high-temperature cooking, including frying, baking, roasting and also industrial processing, at +120°C and low moisture.
The main chemical process that causes this is known as the Maillard Reaction; it is the same reaction that ‘browns’ food and affects its taste.
Acrylamide forms from sugars and amino acids (mainly one called asparagine) that are naturally present in many foods.
CAS Number: 79-06-1
EC Number: 201-173-7
IUPAC Name: Prop-2-enamide
Chemical Formula: C3H5NO
Other names: ACRYLAMIDE, 79-06-1, 2-Propenamide, prop-2-enamide, Propenamide, Ethylenecarboxamide, Acrylic amide, Vinyl amide, Akrylamid, Acrylic acid amide, Acrylagel, Propeneamide, Optimum, 9003-05-8, 2-Propeneamide, Amresco Acryl-40, Ethylene Carboxamide, Propenoic acid amide, Amid kyseliny akrylove, RCRA waste number U007, Acrylamide Monomer, Akrylamid [Czech], CCRIS 7, Amide propenoic acid, NSC 7785, Porisutoron, HSDB 191, Amid kyseliny akrylove [Czech], acryl amide, CHEBI:28619, Flokonit E, Aminogen PA, Acrylamide Monome, Flygtol GB, Stipix AD, EINECS 201-173-7, Superfloc 84, Cytame 5, UNII-20R035KLCI, Sursolan P 5, Solvitose 433, Sumitex A 1, Superfloc 900, Cyanamer P 35, Gelamide 250, Nacolyte 673, Versicol W 11, BRN 0605349, Magnafloc R 292, Sumirez A 17, Sumirez A 27, 20R035KLCI, Aerofloc 3453, Cyanamer P 250, Praestol 2800, DTXSID5020027, Himoloc SS 200, Stokopol D 2624, ACYLAMIDE-, AI3-04119, Bio-Gel P 2, Reten 420, American Cyanamid KPAM, BioGel P-100, K-PAM, NSC-7785, American Cyanamid P-250, Dow ET 597, DTXCID6027, Taloflote, Pamid, AAM, Acrylamide, electrophoresis grade, NSC7785, EC 201-173-7, Acrylamide [UN2074] [Poison], MFCD00008032, Himoloc OK 507, Percol 720, PAARK 123sh, ACRYLAMIDE (IARC), ACRYLAMIDE [IARC], ACRYLAMIDE (MART.), ACRYLAMIDE [MART.], PAA-1, Dow J 100, PAA 70L, PAM-50, Acrilamida, Q 41F, AP 273, ET 597, Acrylamide 1000 microg/mL in Methanol, CAS-79-06-1, J 100, P 250, P 300, Propenoic acid, amide, UN2074, RCRA waste no. U007, acrylarnide, Acrylamide (1.0 mg/mL in Deionized water with 0.1% Formic Acid), Amide propenoate, 2-propene amide, acrylioic acid amide, 1HC, 37 - Acrylamide, Acrylamide, 97%, Bio Gel P2, Bio Gel P-2, Bio-Gel P-2, ACRYLAMIDE [MI], CH2CHCONH2, ACRYLAMIDE [HSDB], bmse000392, Acrylamide Solution, 40%, Acrylamide, >=98.0%, Acrylamide, >=99.9%, RCRA Waste Number U007, WLN: ZV1U1, PROPENAMIDE (50%), Acrylamide_RamanathanGurudeeban, BIDD, Acrylamide, analytical standard, CHEMBL348107, GTPL4553, Acrylamide, for synthesis, 99%, USEPA Pesticide Code: 600008, BCP25183, Tox21_201526, Tox21_300145, BDBM50226193, NSC116573, NSC116574, NSC116575, NSC118185, STL282727, 788 - Acrylamide analysis in snacks, 881 - Acrylamide analysis in coffee, AKOS000120965, Ethylene monoclinic tablets carboxamide, Acrylamide, purum, >=98.0% (GC), NSC-116573, NSC-116574, NSC-116575, NSC-118185, UN 2074, Acrylamide Monomer (ca. 50% in Water), Acrylamide Monomer [for Electrophoresis], NCGC00090736-01, NCGC00090736-02, NCGC00090736-03, NCGC00090736-04, NCGC00090736-05, NCGC00253932-01, NCGC00259076-01, Acrylamide Monomer, [for Electrophoresis], Acrylamide, SAJ first grade, >=98.0%, 1ST001221, DB-124507, DB-253723, A0139, A1132, Acrylamide, Ultrapure, Electrophoresis Grade, NS00009623, EN300-20803, C01659, G77307, Acrylamide, suitable for electrophoresis, >=99%, A839565, Acrylamide, for electrophoresis, >=99.0% (GC), Q342939, Acrylamide, for molecular biology, >=99% (HPLC), J-200356, J-510287, Acrylamide, certified reference material, TraceCERT(R), Acrylamide, for electrophoresis, >=99% (HPLC), powder, BC269F2E-D242-48E1-87E4-E51DB86FF0A8, F8880-6341, InChI=1/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5, Acrylamide, for Northern and Southern blotting, powder blend, Acrylamide, Vetec(TM) reagent grade, suitable for electrophoresis, 9082-06-8
Acrylamide is found in products such as potato crisps, French fries, bread, biscuits and coffee.
Acrylamide was first detected in foods in April 2002 although it is likely that it has been present in food since cooking began.
Acrylamide also has many non-food industrial uses and is present in tobacco smoke.
Acrylamide is a chemical that naturally forms in starchy food products during everyday high-temperature cooking.
Acrylamide is likely that acrylamide has been present in food since cooking began.
Acrylamide mainly forms from sugars and amino acids (mainly one called asparagine) that are naturally present in many foods. The chemical reaction that causes this is known as the Maillard Reaction.
This is the same chemical reaction that ‘browns’ food and affects its taste.
Acrylamide also has widespread industrial non-food uses and is present in tobacco smoke.
Acrylamide (or acrylic amide) is an organic compound with the chemical formula CH2=CHC(O)NH2.
Acrylamide is a white odorless solid, soluble in water and several organic solvents.
From the chemistry perspective, acrylamide is a vinyl-substituted primary amide (CONH2).
Acrylamide is produced industrially mainly as a precursor to polyacrylamides, which find many uses as water-soluble thickeners and flocculation agents.
Acrylamide is highly toxic, likely to be carcinogenic, but its main derivative polyacrylamide is nontoxic.
The possibility that this innocuous bulk chemical contains traces of its hazardous precursor has long attracted attention.
Production
Acrylamide can be prepared by the hydrolysis of acrylonitrile:
CH2=CHCN + H2O → CH2=CHC(O)NH2
The reaction is catalyzed by sulfuric acid as well as various metal salts.
Hydrolysis is however mainly catalyzed by the enzyme nitrile hydratase.
In 2008, an estimated 750,000,000 kg of polyacrylamide were produced, which requires an equal amount of the monomer acrylamide.
Because acrylamide is volatile and hazardous, it is mainly handled as an aqueous solution.
Uses
The majority of acrylamide is used to manufacture various polymers, especially polyacrylamide.
This water soluble polymer, which has very low toxicity, is widely used as thickener and flocculating agent.
These functions are valuable in the purification of drinking water, corrosion inhibition, mineral extraction, and paper making.
Polyacrylamide gels are routinely used in medicine and biochemistry for purification and assays.
Acrylamide can arise in some cooked foods via a series of steps by the reaction of the amino acid asparagine and glucose.
This condensation, one of the Maillard reactions, followed by dehydrogenation produces N-(D-glucos-1-yl)-L-asparagine, which upon pyrolysis generates some acrylamide.
Acrylamide is a colorless, odorless, crystalline solid that can react violently when melted. When it is heated, sharp fumes may be released.Acrylamide is used to make polyacrylamide, which is mainly used in treating waste water discharge from water treatment plants and industrial processes.
In addition, acrylamide and polyacrylamides are used in the production of dyes and organic chemicals, contact lenses, cosmetics and toiletries, permanent-press fabrics, paper and textile production, pulp and paper production, ore processing, sugar refining, and as a chemical grouting agent and soil stabilizer for the construction of tunnels, sewers, wells and reservoirs.Acrylamide is formed in foods that are rich in carbohydrates when they are fried, grilled, or baked.
The largest use for acrylamide is as an intermediate in the production of organic chemicals and in the synthesis of polyacrylamides. Acute (short-term) and chronic (long-term) oral exposures to acrylamide have resulted in damage to the nervous system in humans and animals.
Human data are inadequate on acrylamide and cancer risk. In rats orally exposed to acrylamide, significantly increased incidences of tumors at multiple sites have been observed. EPA has classified acrylamide as a Group B2, probable human carcinogen.
Appearance: white crystalline solid, no odor
Density: 1.322 g/cm3
Melting point: 84.5 °C (184.1 °F; 357.6 K)
Boiling point: None (polymerization); decomposes at 175-300°C
Solubility in water: 390 g/L (25 °C)
Molecular Weight: 71.08 g/mol
XLogP3: -0.7
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Rotatable Bond Count: 1
Exact Mass: 71.037113783 g/mol
Monoisotopic Mass: 71.037113783 g/mol
Topological Polar Surface Area: 43.1Ų
Heavy Atom Count: 5
Complexity: 57.9
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Acrylamide is a colorless, odorless, crystalline amide that polymerizes rapidly and can form as a byproduct during the heating of starch-rich foods to high temperatures. Acrylamide is used in the production of polymers mainly in the water treatment industry, pulp and paper industry and textile treatment industry and is used as a laboratory reagent.
The polymer is nontoxic, but exposure to the monomer can cause central and peripheral nervous system damage resulting in hallucinations, drowsiness and numbness in the hands and legs. Acrylamide is reasonably anticipated to be a human carcinogen.
Acrylamide (ACR) is a chemical used in many industries around the world and more recently was found to form naturally in foods cooked at high temperatures. Acrylamide is a neurotoxicant, reproductive toxicant, and carcinogen in animal species. Only the neurotoxic effects have been observed in humans and only at high levels of exposure in occupational settings.
The mechanism underlying neurotoxic effects of ACR may be basic to the other toxic effects seen in animals. This mechanism involves interference with the kinesin-related motor proteins in nerve cells or with fusion proteins in the formation of vesicles at the nerve terminus and eventual cell death. Neurotoxicity and resulting behavioral changes can affect reproductive performance of ACR-exposed laboratory animals with resulting decreased reproductive performance. Further, the kinesin motor proteins are important in sperm motility, which could alter reproduction parameters.
Effects on kinesin proteins could also explain some of the genotoxic effects on ACR. These proteins form the spindle fibers in the nucleus that function in the separation of chromosomes during cell division. This could explain the clastogenic effects of the chemical noted in a number of tests for genotoxicity and assays for germ cell damage. Other mechanisms underlying ACR-induced carcinogenesis or nerve toxicity are likely related to an affinity for sulfhydryl groups on proteins. Binding of the sulfhydryl groups could inactive proteins/enzymes involved in DNA repair and other critical cell functions.
Direct interaction with DNA may or may not be a major mechanism for cancer induction in animals. The DNA adducts that form do not correlate with tumor sites and ACR is mostly negative in gene mutation assays except at high doses that may not be achievable in the diet. All epidemiologic studies fail to show any increased risk of cancer from either high-level occupational exposure or the low levels found in the diet.
In fact, two of the epidemiologic studies show a decrease in cancer of the large bowel. A number of risk assessment studies were performed to estimate increased cancer risk. The results of these studies are highly variable depending on the model. There is universal consensus among international food safety groups in all countries that examined the issue of ACR in the diet that not enough information is available at this time to make informed decisions on which to base any regulatory action.
Too little is known about levels of this chemical in different foods and the potential risk from dietary exposure. Avoidance of foods containing ACR would result in worse health issues from an unbalanced diet or pathogens from under cooked foods.
There is some consensus that low levels of ACR in the diet are not a concern for neurotoxicity or reproductive toxicity in humans, although further research is need to study the long-term, low-level cumulative effects on the nervous system. Any relationship to cancer risk from dietary exposure is hypothetical at this point and awaits more definitive studies.
Acrylamide is a white crystalline chemical substance and is a raw material for production of polyacrylamide.
Solid acrylamide (abbreviated AM) is usually colorless and transparent flaky crystals with pure product being white crystalline solid which is soluble in water, methanol, ethanol, propanol, and slightly soluble in ethyl acetate, chloroform, and benzene.
Acrylamide can be hydrolyzed to acrylic acid in acidic or alkaline environment.
Acrylamide is a large class of the parent compound of monomers including methacrylamide, the AMPS (anionic monomer, 2-Acraylamide-2-Methyl Propane Sulfonic Acid), the DMC (cationic monomer, methyl-acryloyloxyethyl trimethyl ammonium chloride) and N-substituted acrylamide compound.
Occupational exposure is mainly seen in acrylamide production and the synthesis of resins, adhesives, etc.
Acrylamide is also possible for contract in underground construction, upon soil improvement, painting, paper industry and garment processing.
At daily life, people can touch it in smoking, drinking and eating the starchy foods processed at high temperature.
Chemical Properties
Acrylamide is odorless and colorless crystal.
Acrylamide 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.
Synthesis
At the end of 19th century, people had first made acrylamide using propylene chloride and ammonia.
In 1954, American Cyanamid Company uses sulfuric acid hydrolysis of acrylonitrile for industrial production.
In 1972, Mitsui Toatsu Chemicals, Inc. had first established the skeleton copper (see the metal catalyst) catalyzed acrylamide synthesis via acrylonitrile hydration.
Then other countries have developed different types of catalyst and applied this technology for industrial production.
In 1980s, Japanese Nitto Chemical Industry Company has achieved that using biological catalyst for industrial production of acrylamide from acrylonitrile.
Sulfuric acid hydration way
Acrylonitrile and water is hydrolyzed into acrylamide sulfate in the presence of sulfuric acid and then treated neutralized liquid ammonia to give ammonium sulfate and acrylamide:
CH2 = CHCN + H2O + H2SO4 → CH2 = CHCONH2 • H2SO4 CH2 = CHCONH2 • H2SO4 + 2NH3→ CH2 = CHCONH2 + (NH4) 2SO4
The disadvantage of this method is by-producing a large number of low-value, low fertilizing efficacy-ammonium sulfate and causing serious sulfuric acid corrosion and pollution.
Catalytic hydration way
Acrylonitrile is reacted with water by the copper-based catalyst to have liquid phase hydration reaction at 70~120 °C at 0.4MPa pressure.
CH2 = CH-CN + H2O → CH2 = CHCONH2; Filter the catalyst after reaction catalyst; recycle the unreacted acrylonitrile; acrylamide solution was concentrated and cooled to give crystals.
This is a simple method with the yield up to 98%.
Polymerization
For polymerization of acrylamide, people generally applies chemical catalytic systems or photocatalytic systems.
Chemical catalyst system: chemical catalytic polymerization of acrylamide is done in the systems containing the trigger and accelerator.
Trigger reagents participating the reaction include ammonium persulfate (or potassium persulfate) and hydrogen peroxide while the accelerator includes dimethylamine propionitrile and so on.
Because the polymerization of acrylamide can performed under both acidic or alkaline conditions, so the choice of trigger and accelerator should be changed with pH.
When the aqueous solution of acrylamide (Arc), cross-linking agent (Bis) and tetramethylethylenediamine (tetramethyl ethylene diamine, TEMED) is added into ammonium persulfate (ammoniumpersulfate, AP), AP [(NH4) 2S20s] immediately generate radical (S: OU-2S07), after the reaction between Arc and the free radicals, then it becomes "activate", activated Arc connects with each other to form a long chain poly.
The solution containing this polymer chain, although is sticky but can’t form a gel and can form into a gel only when Bis is also presented.
In the AP-TEMED catalyzed system, the initiating polymerization rate between Arc and Bis is positively proportional to the square root of the concentration of AP and can occur rapidly under alkaline conditions.
For example, the complete polymerization of 7% Arc, only needs 0.5 h upon pH8.8; however, needs 1.5 h upon pH4.3.
In addition, temperature, oxygen molecules and other impurities will also affect the rate of polymerization.
Usually faster polymerization occurs at room temperature than at 0 °C; Solution subjecting to pre-pumping also has faster polymerization rate than that without pre-puming.
Photocatalytic System: This catalysis of this system is vitamin B2.
Photo-polymerization process is catalyzed at light excitation.
Vitamin B: in the presence of oxygen and ultraviolet light, can produce products containing free radicals whose function is similar as AP agent described above.
The mixture is usually placed next to a fluorescent lamp where the reaction can take place.
When using Vitamin B2 for catalyzing, TEMED is not demaned, but adding it can accelerate the rate of polymerization.
Gel formed by photo-polymerization is milky white like with poor transparency.
The advantage of using this catalyst is that it needs a very small amount (1ml/100mi) without any adverse effect on the analysis of samples; polymerization time can be extended or shortened by chaning the light intensity and time.
The apertube of chemical polymerization is smaller thant that of photo-polymerization.
The reproducibility and transparency is also better for the former one than the latter one.
However, the trigger of the chemical polymerization, AP, is a strong oxidizing agent, tend to cause loss of activity of certain protein molecules if remaining in the gel or cause distortion on the electrophoresis pattern.
Uses
Acrylamide can be used as a monomer of polyacrylamide.
Its polymer or copolymer is used as chemical grouting materials, soil conditioners, flocculants, adhesives and coatings.
Polyacrylamide, when used as a kind of additive, can improve the oil recycling efficiency.
When used as flocculants, it can be used for sewage treatment.
Acrylamide can also be used as a paper strength agent.
Acrylamide is the most important products in acrylamide and methacrylamide-based products.
Since its application in industry in 1954, the demand gradually increase.
Acrylamide is mainly used for the preparation of water soluble polymers which can be used as additives to improve oil recovery; as a flocculant, thickening agents, and paper additives.
A small amount of acrylamide is introduce the hydrophilic center into the lipophilic polymer to improve the viscosity, increase the softening point and improve anti-solvents ability of resin, and can aso introduce a center for the coloring property of dye.
Acrylamide is also often used as a component of the photopolymer.
For the vinyl polymer, its crosslinking reaction can take advantage of this kind of reactive amide groups.
Acrylamide can co-polymerizze with certain monomers such as vinyl acetate, styrene, vinyl chloride, vinylidene chloride, and acrylonitrile to obtain a polymer with a variety of applications.
The main application areas:
used for the oilfield; the materials can be used in oilfield injection of wells for adjustment of the injection profile.
Mix this product with initiator, and deaerator and inject into the high permeability layer part of water wells.
This will lead the formation of high-viscosity polymer unearth of the stratum.
This can plug the large pore, increase the swept volume of oil, and enhance the oil recovery.
In addition, the product polymer or copolymer can be used for tertiary oil recovery, fracturing, water shutoff, drilling mixing process and chemical grouting.
Acrylamide can be used as flocculants. Its partially hydrolyzed product and its graft copolymer of methyl cellulose can be used in wastewater treatment and sewage treatment.
Soil conditioner; using the hydrolyzed product as soil amendments can aggregate soil and can improve air circulation, water permeability and water retention.
Modification of fiber and resin processing; using acrylamide for carbamylation or graft polymerization can improve the resin arrangement of a variety of fiber containing synthetic fiber, as well as for warp and printing paste in order to improve the basic physical properties of fabrics as well as preventing wrinkle, shrink and keeping a good hand feeling.
Acrylamide can be used as paper enhancer; copolymer of acrylamide and acrylic acid or partial hydrolysis products of polyacrylamide can be used as paper strength reinforcing agent for either replacing or combining with starch, and water-soluble amino resin.
it can be used as an adhesive agent including glass fiber adhesive agent with the combination of phenolic resin and polyacrylamide solution, as well as pressure sensitive adhesive combined with synthetic rubber.
Acrylamide is the raw material for producing polyacrylamide and related products.
Acrylamide can be used as the monomer of polyacrylamide. Its polymer or copolymer can be used as chemical grouting materials, soil conditioners, flocculants, adhesives and coatings.
Polyacrylamide, as an additive, can improve oil recovery.
As a kind of flocculants, it can be used for waste water treatment as well as paper strength enhancer can.
Acrylamide is the raw material for producing polyacrylamide and related products.
Acrylamide can also used for determining the relative molecular weight of acid.
Production methods
Acrylonitrile sulfate hydration; Acrylonitrile and water is hydrolyzed into acrylamide sulfate in the presence of sulfuric acid and then treated neutralized liquid ammonia to give ammonium sulfate and acrylamide:
The reaction products further undergoes filtering and separation.
Crystallize the filtrate, dry to obtain the final product.
The disadvantage of this method is by-producing a large number of low-value, low fertilizing efficacy-ammonium sulfate and causing serious sulfuric acid corrosion and pollution.
This method can produce by-products of 2280 kg ammonium sulfate in per tons of acrylonitrile.
Material consumption amount: Acrylonitrile (100%) 980kg/t, sulfuric acid (100%) 200kg/t, ammonia (100%) 700kg/t.
Direct hydration of acrylonitrile: acrylonitrile is directly hydrated by water with copper being the catalyst at 85-125 °C and 0.3-0.4MPa pressure.
The yielding aqueous solution of acrylamide (containing only small amounts of by-products) can be directly sold as a finished product.
This method avoids acrylamide dust pollution and is advantageous for labor protection for using aqueous solution.
Reference Product Specifications: appearance: white flakes or powder.
With first-grade product containing content ≥95%; Secondary-grade content ≥90%; grade III content ≥85%.
Enzyme catalysis; at room temperature transfer the acrylonitrile solution into the fixed-bed reactor containing bacteria catalyst; after the reaction, 100% of acrylonitrile is converted into acrylamide.
After isolation and even without the necessity of refining and concentration, we can get the acrylamide industrial products.
Concentrated sulfuric acid hydration method: mixture containing sulfate, phenothiazine (polymerization inhibitor), and water is added to the reactor; stir slowly with dropping acrylonitrile After the addition is completed, raise the temperature to 95~100 °C, keep the temperature for 50 min.
Cool to 20~25 °C, dilute with an appropriate amount of water, neutralize with sodium carbonate, filtrate to obtain aqueous acrylic acid solution.
Further cool and crystallize, separate, dry to obtain the completed products.
Catalytic hydration method; acrylonitrile and water undergoes liquid phase hydration in the presence of copper-based catalyst;
Acrylamide is generally used for continuous production with the reaction temperature being 85~120 °C, reaction pressure being 0.29~0.39 MPa, feed concentration of 6.5%, airspeed being 5 L/ h, the conversion rate being 85%, and selectivity being about 95% and the concentration of acrylamide in the reaction being 7% to 8%.
Aqueous solution obtained by this method may be directly used as the product for sale.
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.
Chemical Properties
Acrylamide, in monomeric form, is an odorless, flake-like crystals which sublime slow at room temperature.
May be dissolved in a flammable liquid.
Uses
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.
Acrylamide is reasonably anticipated to be a hum an carcinogen.
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
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.
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.
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.
About Acrylamide
Helpful information
Acrylamide is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 100 000 to < 1 000 000 tonnes per annum.
Acrylamide is used by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
Widespread uses by professional workers
Acrylamide is used in the following products: pH regulators and water treatment products and laboratory chemicals.
Acrylamide has an industrial use resulting in manufacture of another substance (use of intermediates).
Acrylamide is used in the following areas: building & construction work, health services and scientific research and development.
Other release to the environment of Acrylamide is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners).
Uses at industrial sites
Acrylamide is used in the following products: laboratory chemicals.
Acrylamide has an industrial use resulting in manufacture of another substance (use of intermediates).
Acrylamide is used in the following areas: scientific research and development and health services.
Acrylamide is used for the manufacture of: chemicals.
Release to the environment of Acrylamide can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates) and for thermoplastic manufacture.
Manufacture
Release to the environment of Acrylamide can occur from industrial use: manufacturing of the substance and as an intermediate step in further manufacturing of another substance (use of intermediates).
Acrylamide is a colorless, odorless, crystalline solid thatcan react violently when melted.
When it is heated, sharpfumes may be released.
Acrylamide is used to make polyacrylamide, which ismainly used in treating waste water discharge from watertreatment plants and industrial processes.
In addition, acrylamide and polyacrylamides are used inthe production of dyes and organic chemicals, contactlenses, cosmetics and toiletries, permanent-press fabrics,paper and textile production, pulp and paper production,ore processing, sugar refining, and as a chemical groutingagent and soil stabilizer for the construction of tunnels,sewers, wells and reservoirs.
Acrylamide is formed in foods that are rich incarbohydrates when they are fried, grilled, or baked.
Acrylamide is a colorless, odorless, crystalline amide that polymerizes rapidly and can form as a byproduct during the heating of starch-rich foods to high temperatures.
Acrylamide is used in the production of polymers mainly in the water treatment industry, pulp and paper industry and textile treatment industry and is used as a laboratory reagent.
The polymer is nontoxic, but exposure to the monomer can cause central and peripheral nervous system damage resulting in hallucinations, drowsiness and numbness in the hands and legs.
Acrylamide is reasonably anticipated to be a human carcinogen.
Acrylamide appears as white crystalline solid shipped either as a solid or in solution.
A confirmed carcinogen. Toxic by skin absorption.
Less dense than water and soluble in water.
Used for sewage and waste treatment, to make dyes, adhesives.
The solid is stable at room temperature, but upon melting may violently polymerize.
Use and Manufacturing
Household & Commercial/Institutional Products
Auto Products
Home Maintenance
Inside the Home
Acrylamide is used as a reactive monomer and intermediate in the production of organic chemicals and in the synthesis of polyacrylamides.
Acrylamide is also used as a flocculent for sewage and waste treatment, soil conditioning agents, ore processing, paper and textile industries, and in the manufacture of dyes, adhesives, and permanent press fabrics.
Acrylamide is used as a reactive monomer and intermediate in the production of organic chemicals.
Acrylamide has a wide variety of uses as a polymer or copolymer in such applications as adhesives, fibers, paper sizing, molded parts, water coagulant aids, grouting agent, and textiles.
Industry Uses
Intermediates
Paint additives and coating additives not described by other categories
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IDENTIFICATION AND USE: Acrylamide is a white crystalline solid.
Acrylamide is mainly used in the production of polymers and copolymers for various purposes.
All acrylamide in the environment is man-made, the main source being the release of the monomer residues from polyacrylamide used in water treatment or in industry.
Acrylamide is a chemical substance formed when starchy foods, such as potatoes and bread, are cooked at high temperatures (above 120°C).
Acrylamide can be formed when foods are:
baked
fried
grilled
toasted
roasted
Acrylamide is not deliberately added to foods – it is a natural by-product of the cooking process and has always been present in our food.
Acrylamide is found in a wide range of foods including:
roasted potatoes and root vegetables
chips
crisps
toast
cakes
biscuits
cereals
coffee
What is acrylamide?
Acrylamide is a chemical that can form in some foods during high-temperature cooking processes, such as frying, roasting, and baking.
Acrylamide in food forms from sugars and an amino acid that are naturally present in food; it does not come from food packaging or the environment.
The chemical acrylamide, or acrylic amide, is a white, odorless, crystal compound.
Acrylamide has the chemical formula C3H5NO.
It’s used to make plastics and treat wastewater, among other things.
Overexposure at work can cause damage to your nervous system.
It’s also thought to increase cancer risk.
Every day you’re exposed to acrylamide through smoking and secondhand smoke, as well as personal care products and household items.
In 2002, Swedish scientists also discovered the compound in a wide range of foods, including baked goods and coffee.
Scientists believe the acrylamide in food is a product of the Maillard reaction. This reaction occurs when sugars and amino acids are heated above 248°F (120°C) .
What is known is that when coffee beans are roasted, acrylamide is formed.
There’s no way to remove it from coffee, so when you drink it, you’re exposing yourself to the chemical.
Acrylamide is a potentially harmful chemical formed during the coffee bean roasting process.
Acrylamide is a chemical widely used during the manufacturing of paper, dye, and other industrial products. Acrylamide can also be formed when certain foods are cooked at high temperatures.
Frying, baking, or roasting certain foods, such as potatoes or grains, can create acrylamide.
French fries and potato chips, for example, may have measurable acrylamide levels.
Acrylamide is also found in cigarette smoke.
How does acrylamide get into foods?
When certain foods are cooked at high temperatures, sugars, such as glucose and fructose, can react with the free amino acid, asparagine, to form acrylamide.
Acrylamide forms as part of a chemical reaction, known as the Maillard reaction, which contributes to the aroma, taste, and color of cooked foods.
Acrylamide is one of the hundreds of chemicals that can form during the Maillard reaction.
Acrylamide is a chemical that naturally forms in starchy foods when they are cooked at high temperatures, for example, roasting, frying and baking.
The browner the food is after cooking, the higher the level of acrylamide present.
What foods are of most concern for acrylamide?
The most important food groups are fried potato products, like chips, crisps, roast potatoes and other roasted root vegetables, bread, coffee, biscuits and crackers.
Once again, the browner the food is after cooking the more acrylamide will be present.
Acrylamide is a chemical substance formed by a reaction between amino acids and sugars.
Acrylamide typically occurs when foods with high starch content such as potatoes, root vegetables, cereal-based foods, bread, coffee and coffee substitutes are cooked at high temperatures (over 120°C).
Acrylamide is a suspected carcinogen. The presence of acrylamide in food was initially detected in 2002.
Yet in 2015 the EFSA (European Food Safety Authority) stated that current levels of dietary exposure to acrylamide were a growing concern as the levels of acrylamide were not consistently decreasing.
Acrylamide is also known as vinyl amide and acrylamide monomer
Acrylamide is a colourless, odourless solid
Acrylamide is an important industrial chemical
Acrylamide can be released into the environment during its production and use
the general public may be exposed to low amounts via ingestion of food (as it is produced naturally in foods cooked at high temperatures) and via cigarette smoke
breathing in dust or vapours of acrylamide for a short period of time can cause sore throat and cough
ingestion of large amounts of acrylamide may cause burning and ulceration of the mouth and throat and stomach upset
Skin contact can lead to irritation, numbness, tingling, sweating, itchy rash and peeling
Acrylamide may be able to cause cancer in humans
Acrylamide may harm the unborn child
What is acrylamide?
Acrylamide is a colourless, odourless solid. Other names for acrylamide are vinyl amide and acrylamide monomer.
What is acrylamide used for?
Acrylamide is an important industrial chemical that is used to produce polyacrylamides, which are used as cleaning agents in water treatment processes.
Acrylamide is also used as a grouting agent and to produce dyes and other industrial chemicals.
How does acrylamide get into the environment?
Acrylamide can enter the environment during its production and use.
Acrylamide is important not to over-cook certain foods. Over-cooking or burning certain foods means that these foods can be higher in acrylamide.
Acrylamide is a chemical thatis formed naturally when some foods; containing asparagine (an amino acid) and sugars; are cooked at high temperatures (above 120⁰C) such as by frying, roasting, baking, grilling and toasting.
Legislation is in place to reduce acrylamide levels in food, as it is a probable carcinogen in humans.
