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Acrylamid
aam · 2-PROPENAMIDE · prop-2-enamide · ACRYLAMIDE MONOMER · PROPENAMIDE · Acrylic amide · optimum · Acrylamid
Identifikatoren & physikalische Daten
| CAS No. | 79-06-1 |
|---|---|
| Summenformel | C3H5NO |
| Durchschnittliche Molmasse | 71,08 g/mol |
| Monoisotopische Masse | 71,03711378 g/mol |
| SMILES | C=CC(N)=O |
| InChIKey | HRPVXLWXLXDGHG-UHFFFAOYSA-N |
| PubChem CID | 6579 |
| ChEMBL | CHEMBL348107 |
| ChEBI | CHEBI:28619 |
| EC No. | 201-173-7 |
| DTXSID | DTXSID5020027 |
| Lokaler Name | Acrylamid |
Chemische & physikalische Eigenschaften
| XLogP | -0,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 43,1 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 5 |
| Formalladung | 0 |
| Komplexität | 57,9 |
| Stoffklassen | Hazardous Air Pollutants (HAPs)Carcinogens |
| Polymers | Plastics & Rubber -> Other Monomers |
| Kosmetika | Cosmetic ingredients (Acrylamide) -> CIR (Cosmetic Ingredient Review) |
| pH | pH = 5.0-6.5 /50% aqueous solution/5.0-7.0 (50g/l, H2O, 20℃) |
| SpringerMaterials Properties | Schoenflies notation |
| Pestizide | Pesticide -> EPA IRIS |
| LogP (Verteilungskoeffizient) | log Kow = -0.67-0.78 |
| Geruch | Odorless |
| Dichte | 1.122 at 86 °F (EPA, 1998) - Denser than waterwill sink1.122 at 30 °C/4 °C1.13 g/cm³1.122 @ 30°C1,322 g/cm3 |
| Viscosity | 2.71 cP at 25 °C /50% aqueous solution/ |
| Color/Form | Flake-like crystals from benzeneWhite crystalline ... solid |
| Löslichkeit | greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)In water, 3.711X10+2 g/L at 20 °C4.048X10+2 g/L at 30 °CSoluble in ethanol, ethyl ether and acetoneSolubility (g/100 mL) at 30 °C in: methanol 155ethanol 86.2acetone 63.1ethyl acetate 12.6chloroform 2.66benzene 0.346heptane 0.0068390 mg/mL at 25 °CSolubility in water, g/100ml at 25 °C: 204 (very good)2040 g/L (25°C)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. |
| Schmelzpunkt | 82-86 °C(lit.) |
| Siedepunkt | 125 °C25 mm Hg(lit.) |
| Dampfdichte | 2.45 (vs air) |
| Dampfdruck | 0.03 mm Hg ( 40 °C) |
| Brechungsindex | 1.460 |
| Flammpunkt | 138 °C |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | powder |
| pKa (Säurekonstante) | 15.35±0.50(Predicted) |
| Farbe | White |
| Geruch | Odorless solid |
| Merck | 14,129 |
| BRN | 605349 |
| Henry-Konstante | (x 10-9 atmm3/mol): 3.03 at 20 °C (approximate - calculated from water solubility and vapor pressure) |
| Stabilität | 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. |
| Hauptanwendungen | cleaning productscosmeticsenvironmentalfood and beveragespersonal care |
| InChI | 1S/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5) |
| InChIKey | HRPVXLWXLXDGHG-UHFFFAOYSA-N |
| SMILES | NC(=O)C=C |
| LogP (Verteilungskoeffizient) | -0.9 at 20℃ and pH7 |
| CAS Datenbank | 79-06-1(CAS DataBase Reference) |
| NIST chemische Informationen | Acrylamide(79-06-1) |
| EPA chemische Informationen | Acrylamide (79-06-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]P203, P260, P261, P264, P264+P265, P270, P271, P272, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 3.7% (58 of 1562) of reports.H301 (94.8%): Toxic if swallowed [Danger Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Chemical: 2-PropenamideHazard Traits - CarcinogenicityDermatotoxicityDevelopmental ToxicityGenotoxicityHematotoxicityNeurotoxicityReproductive ToxicityRespiratory ToxicityRegulation (EC) No 178/2002 (amended)2-Propenamide is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenamide are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 09-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15534Restricted substance: Acrylamide |
| Weitere Sicherheitsinformationen | PEC / SN / Other assessments - Acrylamide: Health and Environment |
| DOT-Kennzeichnung | PoisonFlammable Liquid |
| Brandgefahren | Pure acrylamide will decompose at 347-572F giving ammonia, hydrogen and carbon monoxide. Avoid strong oxidizers. Avoid heat, ultraviolet light. Hazardous polymerization may occur. It readily polymerizes when heated to the melting point or when exposed to ultraviolet light. It is known to polymerize with violence when heated. (EPA, 1998)Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)polymerization hazard]:Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:· Combustible material: may burn but does not ignite readily.Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air. |
| Brandpotenzial | Combustible solid. |
| Gesundheitsgefahren | Classified as very toxicprobable oral lethal human dose is between 50 and 500 mg/kg or between 1 teaspoon and 1 ounce for a 150 lb. person. Polymerized acrylamide is not toxic, but the monomer can cause peripheral nerve damage. It is a cumulative neurotoxin and repeated exposure to small amounts may cause serious injury to the nervous system. The neurological effects may be delayed. Polymer inhibitors or stabilizers added to the monomer may also produce toxicity. The symptoms of acrylamide toxicity are consistent with mid-brain lesions and blocked transport along both motor and sensory axons. Individuals with nervous system diseases should not be exposed to acrylamide. (EPA, 1998)Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)polymerization hazard]:Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:· TOXIC and/or CORROSIVEinhalation, ingestion or skin contact with material may cause severe injury or death. |
| Gefahrenübersicht | 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.Can cause sensorimotor neuropathy after occupational exposurePolyacrylamide, with less than 0.01% acrylamide, is nontoxic and considered safe as a cosmetic ingredient. . . . Available data indicate no unique sensitivity to the fetus. . . . Most cases of acrylamide poisoning in humans involved exposures over weeks or months from handling the monomer in the course of polymerization. . . . Kim et al. (2017) reported two cases of dermal and neural toxicity in Korean grouting workers with exposure to grouting agents that contained a high concentration of acrylamide (32 and 39% monomer). [ACGIH] Allergic contact dermatitis reported in laboratory workers using polyacrylamide gels for electrophoresis[Kanerva, p. 1738] Germ cell mutagens that have shown to increase the mutant frequency in the progeny of exposed mammals. [MAK] Acrylamide (UN2074) has warning of explosive polymerization[ERG 2016] |
| DOT-Nummer und Handbuch | 3426 153P2074 153P |
| FDA-Anforderungen | Homopolymers and copolymers of acrylamide are indirect food additives for use only as a component of adhesives. /Homopolymers and copolymers of acrylamide/ |
| Reaktive Gruppe | Amides and Imides |
| EG-Einstufung | Symbol: TR: 45-46-20/21-25-36/38-43-48/23/24/25-62S: 53-45Note: D, E |
| UN-Einstufung | UN Hazard Class: 6.1UN Pack Group: III |
| Brandbekämpfung | Fight fire from maximum distance. Dike fire control water for later disposaldo not scatter the material.Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)polymerization hazard]:Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:Use water spray, powder, alcohol-resistant foam, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention . Wear protective gloves when administering first aid.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Give one or two glasses of water to drink. Refer immediately for medical attention. |
| Freisetungsmaßnahmen | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| Erste Hilfe | Warning: Effects may be delayed. Caution is advised.Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)polymerization hazard]:Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:General First Aid:(General first aid procedures) |
| Sichere Lagerung | Separated from incompatible materials. See Chemical Dangers. Cool. Keep in the dark. Well closed. Store in an area without drain or sewer access. |
| Firefighting Hazards | Closed containers may rupture violently when heated. |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA).Biological Exposure Indices (BEI) [ACGIH] - N-(2-Carbamoylethyl)valine (CbEv) in blood (not critical)BEI = 500 pmo/g globin (After 120 days of representative work/exposure to Acrylamide)S-(2-Carbamoylethyl)mercapturic acid (AAMA) in urine (end of shift)BEI = 800 ug/g creatine. |
| Brandbekämpfungsverfahren | Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical, or carbon dioxide.Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.Use dry chemical, carbon dioxide, water spray, or foam extinguishers. ... The only respirators recommended for firefighting are self-contained breathing apparatuses that have full face-pieces and are operated in a pressure-demand or other positive-pressure mode. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. Dike fire control water for later disposaldo not scatter the material.If material is on fire or involved in fire: Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical, or carbon dioxide. /Acrylamide, solid or Acrylamide/For more Fire Fighting Procedures (Complete) data for ACRYLAMIDE (6 total), please visit the HSDB record page. |
| Lagerbedingungen | Keep container tightly closed in a dry and well-ventilated place. Light sensitive. Store under inert gas. Storage class (TRGS 510): Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects.Separate from oxidizing materials and peroxides. Store in a cool, dry, well-ventilated location. Store away from heat, sunlight, acids, and alkalies.Store separately in an area isolated from flammables, combustibles, or other yellow coded materials. ... Store in a secure poison location. ... Store only if stabilized, under inert gas. Before entering confined space where acrylamide may be present, check to make sure that an explosive concentration does not exist. Store in tightly-closed containers in a cool, well-ventilated area. Metal containers involving the transfer of this chemical should be grounded and bonded. Where possible, automatically pump liquid from drums or other storage containers to process containers. Drums must be equipped with self-closing valves, pressure vacuum bungs, and flame arresters. Use only nonsparking tools and equipment, especially when opening and closing containers of this chemical. Sources of ignition, such as smoking and open flames, are prohibited where this chemical is used, handled, or stored in a manner that could create a potential fire or explosion hazard.PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/The effectiveness of phenolic inhibitors is dependent on the presence of oxygen and the monomers must be stored under air rather than an inert atmosphere. Temp must be kept low to minimize formation of peroxides and other products. Moisture may cause rust-initiated polymerization. /Acrylic acid & derivatives/ |
| Reinigungsverfahren | ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.Prompt cleanup and removal are necessary.Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Stay upwindkeep out of low areas. Ventilate closed spaces before entering them. Use water spray to reduce vapors. Remove all ignition sources. Small spills: absorb with sand or other noncombustible absorbent materials and place into containers for later disposal. Small dry spills: with clean shovel place materials into clean, dry container and covermove containers from spill area. Large spills: dike far ahead of spill for later disposal. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area of spill or leak after cleanup is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters.1) VENTILATE AREA ... 2) FOR SMALL QUANTITY, SWEEP ONTO PAPER OR OTHER SUITABLE MATERIAL, PLACE IN APPROPRIATE CONTAINER & BURN IN SAFE PLACE (SUCH AS FUME HOOD). LARGE QUANTITY MAY BE RECLAIMED.For more Cleanup Methods (Complete) data for ACRYLAMIDE (6 total), please visit the HSDB record page. |
| Freisetung ohne Brand | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)polymerization hazard]:Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: |
| Entsorgungsverfahren | Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U007, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubberContaminated packaging: Dispose of as unused product.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 EPA-approved disposal site. Incineration with provisions for scrubbing of nitrogen oxides from flue gases. Deep well injection.For more Disposal Methods (Complete) data for ACRYLAMIDE (12 total), please visit the HSDB record page. |
| Toxikologische Informationen | CDC-ATSDR Toxicological Profile |
| Treatment | EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration. |
| Cancer Sites | Endocrine[in animals: tumors of the lungs, testes, thyroid & adrenal glands] |
| Wechselwirkungen | The primary objective of this investigation was to assess the neuroprotective efficacy of lithium in an acrylamide (ACR)-induced neuropathy model in mice. In this study, Kunming male mice were administered ACR (25 mg/kg bw, i.p. once a day) with or without lithium (25 mg/kg bw, i.p. once a day) for 2 weeks. All ACR-administered mice exhibited severe symptoms of neuropathy. We found that treatment with lithium effectively alleviated behavioral deficits in animals elicited by acrylamide. Interestingly, the reduction of hippocampal neurogenesis resulting from ACR injection was promoted by administration of lithium. Further, lithium treatment significantly offset ACR-induced depletion in p-GSK-3beta (Ser9) levels in hippocampus. Collectively our findings suggest the propensity of lithium to attenuate ACR-induced neuropathy. Further studies are necessary to understand the precise molecular mechanism by which the lithium attenuates neuropathy. Nevertheless, our data clearly demonstrate the beneficial effects of lithium on ACR-induced neuropathy in mice and suggest its possible therapeutic application as an adjuvant in the management of other forms of neuropathy in humans.... The present study investigated the efficacy of geraniol (GE, a natural monoterpene) to mitigate acrylamide (ACR)-induced oxidative stress, mitochondrial dysfunction and neurotoxicity in a rat model and compared its efficacy to that of curcumin (CU, a spice active principle with multiple biological activities). ACR administration (50 mg/kg bw, i.p. 3 times/week) for 4 weeks to growing rats caused typical symptoms of neuropathy. ACR rats provided with daily oral supplements of phytoconstituents (GE: 100 mg/kg bw/dCU: 50 mg/kg bw/d, 4 weeks) exhibited marked improvement in behavioral tests. Both phytoconstituents markedly attenuated ACR-induced oxidative stress as evidenced by the diminished levels of reactive oxygen species, malondialdehyde and nitric oxide and restored the reduced glutathione levels in sciatic nerve (SN) and brain regions (cortex - Ct, cerebellum - Cb). Further, both phytoconstituents effectively diminished ACR-induced elevation in cytosolic calcium levels in SN and Cb. Furthermore, diminution in the levels of oxidative markers in the mitochondria was associated with elevation in the activities of antioxidant enzymes. While ACR mediated elevation in the acetylcholinesterase activity was reduced by both actives, the depletion in dopamine levels was restored only by CU in brain regions. Taken together our findings ... demonstrate that the neuromodulatory propensity of GE is indeed comparable to that of CU and may be exploited as a therapeutic adjuvant in the management of varied human neuropathy conditions.... The current study assessed mixture effects of the three known genotoxic chemicals, 2,4-dichlorophenoxyacetic acid (2,4-D), acrylamide (AA), and maleic hydrazide (MH), in an experiment with a fixed ratio design setup. The genotoxic effects were assessed with the single-cell gel electrophoresis assay (comet assay) for both single chemicals and the ternary mixture. The concentration ranges used were 0-1.4, 0-20, and 0-37.7 mM for 2,4-D, AA, and MH, respectively. Mixture toxicity was tested with a fixed ratio design at a 10:23:77% ratio for 2.4-D:AA:MH. Results indicated that the three chemicals yielded a synergistic mixture effect. It is not clear which mechanisms are responsible for this interaction.The aim of this study was to investigate the protective effects of N-acetylcysteine NAC) against acrylamide toxicity in liver and small and large intestine tissues in rats. The rats were divided into four groups. Acrylamide administration increased malondialdehyde (MDA) levels in all tissues significantly (p<0.05). Butacrylamide+NAC administration decreased MDA levels significantly as compared to the acrylamide group, and lowered it to a level close to the control group values (p<0.05). Glitathione (GSH) levels in liver and small intestine tissues reduced significantly in the acrylamide group (p<0.05). Butacrylamide+NAC administration increased GSH levels significantly in all tissues. Whereas GST activity decreased significantly in the acrylamide group in liver and small intestine tissues as compared to the other groups (p<0.05), the GST activity increased significantly in the acrylamide+NAC group in all tissues as compared to the acrylamide group (p<0.05). Liver histopathology showed that the liver epithelial cells were damaged significantly in the acrylamide group. Small intestine histopathology showed that the intestinal villous epithelial cells were damaged significantly in the acrylamide group. Our results indicate that a high level of acrylamide causes oxidative damage in liver and small and large intestine tissues, while N-acetylcysteine administration in a pharmacological dose shows to have an antioxidant effect in preventing this damage.For more Interactions (Complete) data for ACRYLAMIDE (33 total), please visit the HSDB record page. |
| Zielorgane | Cancer, Neurological (Nervous System), Reproductive (Producing Children)Eyes, skin, central nervous system, peripheral nervous system, reproductive system |
| Gesundheitliche Auswirkungen | Acrylamide is neurotoxic and causes the disassembly or rearrangement of intermediate filaments. It may also damage the male reproductive glands and is believed to be carcinogenic. (L1157) |
| Ökotoxizitätswerte | LC50Species: Pimephales promelas (fathead minnow)Conditions: flow-through bioassay with measured concentrations, 24.1 °C, dissolved oxygen 7.2 mg/L, hardness 50.8 mg/L calcium carbonate , alkalinity 43.3 mg/L calcium carbonate and pH 7.1Concentration: 109 mg/L for 96 hr (confidence limit 103-115 mg/L)EC50Conditions: flow-through bioassay with measured concentrations, 24.1 °C, dissolved oxygen 7.2 mg/L, hardness 50.8 mg/L calcium carbonate, , alkalinity 43.3 mg/L calcium carbonate and pH 7.1Concentration: 105 mg/L for 96 hrEffect: loss of equilibriumSpecies: Pimephales promelas (Fathead Minnow) weight 0.11 g, length 17 mmConditions: freshwater, flow through, 22 °C, pH 8.0-8.5Concentration: 230000 ug/L for 96 hr (95% confidence interval: 160000-340000 ug/L) />99% purity/Species: Oncorhynchus mykiss (rainbow trout) weight 1.0 g, length 40 mmConditions: freshwater, flow through, 12 °C, pH 8.0-8.5Concentration: 88000 ug/L for 96 hrEffect: general behavior changes />99% purity/For more Ecotoxicity Values (Complete) data for ACRYLAMIDE (25 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an experimental Koc value of 50(2) indicates that acrylamide is expected to have very high to high mobility in soil(SRC). In an experiment evaluating leaching using soil TLC, Rf values ranging from 0.64 to 0.88, measured on four soils, indicated acrylamide is mobile in soil with higher mobility in sandy soils than in clay soils(3). Volatilization of acrylamide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.7X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 0.00675 mm Hg at 25 °C(4), and water solubility, 3.711X10+5 mg/L(5). Acrylamide is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Acrylamide is susceptible to biodegradation in soil(6). Utilizing the Japanese MITI(7) and OECD 301D Closed Bottle tests(8), 70 and 98.1% of the Theoretical BOD was reached in 4 weeks, respectively, indicating that acrylamide is readily biodegradable. The nitrogen in acrylamide was recovered as inorganic nitrogen with recoveries after 3 and 14 days at 30 °C ranging from 11-71% in Clarion soil and 74-95% in Canisteo soil, respectively(9). Results from these studies suggested that acrylamide is hydrolyzed in soil under aerobic conditions to produce ammonium ion, which is then oxidized to nitrite ion and nitrate ion(9). In another study using 4 central New York soils at 70% of their moisture capacity, half-lives ranging from 18 to 45 hr were observed(10).AQUATIC FATE: Based on a classification scheme(1), an experimental Koc value of 50(2) indicates that acrylamide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estiamted Henry's Law constant of 1.7X10-9 atm-cu m/mole(SRC), derived from acrylamide's vapor pressure, 0.00675 mm Hg(4), and water solubility, 3.711X10+5 mg/L(5). According to a classification(6), a BCF of 1 for fingerling rainbow trout(7) suggests bioconcentration in aquatic organisms is low(SRC). Acrylamide is susceptible to biodegradation in water(8). Utilizing the Japanese MITI(9) and OECD 301D Closed Bottle tests(10), 70 and 98.1% of the Theoretical BOD was reached in 4 weeks, respectively, indicating that acrylamide is readily biodegradable. In two river die-away tests using aerated Thames River water, the lag time for biodegradation to begin was 220 and 50 hr(11). In the latter case, 90% of the acrylamide disappeared in approximately 150 hr(11). The hydrolysis half-life of acrylamide is >38 years at a pH 7(12).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), acrylamide, which has a vapor pressure of 0.00675 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase acrylamide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 1.4 days(SRC), calculated from its rate constant of 1.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Vapor-phase acrylamide is also degraded in the atmosphere by reaction with ozone(SRC)the half-life for this reaction in air is estimated to be 6.5 days(SRC), calculated from its rate constant of 1.8X10-18 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Acrylamide does not absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC). |
| Lebensmitteluntersuchungswerte | Acrylamide concentrations of 183-404 ug/kg were detected in french fries, <25-202 ug/kg in bread crusts and <25-1522 ug /kg flat breads(1). An acrylamide level of nearly 300 ug/kg was formed in bread crisps over a time-period of toasting(2). Acrylamide was formed in biscuits during the baking using recipes containing sucrose, fructose and/or glucose(3). Frying tests indicated that the French fries that were fried in oils having lower heat transfer coefficients contained lower acrylamide concentrations (913 ug/kg), whereas those fried with oils having higher heat transfer coefficients contained higher acrylamide concentrations (1219 ug/kg)(4). Two different batches of 40 potato crisps brands from 18 producers in 2014 found acrylamide content ranged from 108 to 2180 ug/kg, with an average value of 630 ug/kg and a median of 556 ug/kg(5)in 2014, potato crisps showed an average acrylamide content 14.6% lower than the previous report in 2009 and 57.6% lower than the first report in 2004(5).Acrylamide levels were measured in foods in the 2003 FDA Total Diet Study, which represents 286 ready-to-eat foods in the US food supply. Acrylamide was generally not detected (detection limit 10 ppb) or detected infrequently in dairy, eggs, fats/oils, beverages, fruits, vegetables, legumes, mixtures (casseroles, sandwiches, soups, and pizzas), and meat/poultry/fish(1). Snack foods (corn/tortilla chips, microwave popcorn, potato chips, pretzels) contained some of the highest levels of acrylamide, ranging from 46 to 536 ppb. Acrylamide was also detected relatively frequently in the grains/starches/baked good category, with the highest levels found in graham crackers (211-647 ppb) and butter-type crackers (348-425 ppb). Acrylamide was detected relatively infrequently in baby food products, with the highest levels found in arrowroot cookies (105-267 ppb), sweet potatoes (30-117 ppb), and teething biscuits (128-235 ppb). Similar acrylamide results were reported for the 2004, 2005 and 2006 FDA Total Diet Studies(1).Acrylamide concentrations in various foods and food product groups from Norway, Sweden, Switzerland, the UK, and the US have been reported as follows(1):[Table#716]The mean and range concentrations of acrylamide in potato-based foods from the Netherlands sampled in 1998 were as follows(1):[Table#717]For more Food Survey Values (Complete) data for ACRYLAMIDE (10 total), please visit the HSDB record page. |
| Unerwünschte Wirkungen | Neurotoxin - Sensorimotor |
| Expositionspfade | The substance can be absorbed into the body by inhalation, through the skin and by ingestion.inhalation, skin absorption, ingestion, skin and/or eye contactInhalation (L1157)dermal (L1157)oral (L1157). |
| Milk Concentrations | As part of the US FDA Total Diet Study for 2003, 2004, 2005 and 2006, acrylamide was not detected in whole milk, skim milk or low-fat milk, but was detected in fast food chocolate milkshakes at 14-16 ppb(1). In 1998, the mean conccentration of acrylamide in milk and milk products from the Netherlands were determined as follows (all ug/kg): chocolate drink made up with whole milk, 15coffee creamer power, 15yogurt flavored drink, 15custard caramel, 15milk powder, 15(2).The mean concentration of acrylamide in milk and milk products from the Netherlands sampled in 1998 were as follows(1):[Table#725] |
| RCRA-Anforderungen | U007As stipulated in 40 CFR 261.33, when acrylamide, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5). |
| TSCA-Anforderungen | Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Acrylamide is included on this list. Effective date: 10/4/82Sunset date: 10/4/92. |
| Luftstandards | This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Acrylamide is produced, as an intermediate or a final product, by process units covered under this subpart.Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Acrylamide is included on this list. |
| CERCLA-Meldepflichtmengen | Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2270 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b).Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Acrylamide is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 1,000 or 10,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered form and has a particle size less than 100 micronsor is handled in solution or in molten formor meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... . |
| Landesrichtlinien für Trinkwasser | (AZ) ARIZONA 0.01 ug/L(FL) FLORIDA 1 ug/L(ME) MAINE 0.08 ug/L |
| Federal Drinking Water Standards | EPA Treatment Technique in lieu of MCL. |
| Bundesrichtlinien für Trinkwasser | The maximum contaminant level goal for the following organic contaminant is zero mg/L: acrylamide. |
| F | 8-10 |
| Berufliche Expositionsstufe (OEB) | D |
| Arbeitsplatzgrenzwert (OEL) | TWA: 0.03 mg/m3 [skin] |
| Wassergefährdungsklasse (WGK) | 3 |
| Sofort lebensgefährliche Konzentration | 60 mg/m3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3426 6.1/PG III (ACRYLAMIDE SOLUTION) |
| Zollcode | 29241900 |
| RTECS-Nr. | AS3325000 |
| R-Sätze (R) | 45-46-20/21-25-36/38-43-48/23/24/25-62-48/20/21/22-22-24/25 |
| Toxizität | LD50 i.p. in mice: 170 mg/kg (Peterson, Sheth) |
| Gefahrensymbole | T |
| Sicherheitshinweise (S) | 53-45-24-36/37/39-26-36/37 |
| Gefahrenklasse | 6.1Acute Tox. 3 OralAcute Tox. 4 DermalAcute Tox. 4 InhalationCarc. 1BEye Irrit. 2Muta. 1BRepr. 2Skin Irrit. 2Skin Sens. 1STOT RE 1 Oral |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrstoffdaten | 79-06-1(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 424°C |
Anwendungen & Verwendung
Beschreibung
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.
Verwenden
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.
Herstellung & Synthese
synthetische
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.