Acrylamide

HCID 6579CAS 79-06-1

基本情報

標準SMILES
C=CC(N)=O
InChIKey
HRPVXLWXLXDGHG-UHFFFAOYSA-N
分子式
C3H5NO
平均分子量
71.08 g/mol
単同位体質量
71.03711378

概要

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.

名称と識別子

優先名称
Acrylamide
IUPAC
prop-2-enamide
現地名
アクリルアミド
英語名
Acrylamide
分子式
C3H5NO
分子量
71.08

名称と別名

ACRYLAMIDE79-06-12-Propenamideprop-2-enamidePropenamideAcrylic acid amideAcrylic amideEthylenecarboxamideVinyl amideAkrylamidAcrylagelPropeneamide
名称をさらに表示
アクリルアミド (モノマー)プロペンアミド2-プロペンアミドアコフロックアクリル酸アミドセパランアクリルアミドHGXアクリルアミドモノマー標準原液アクリルサンアミド2-プロペンアマイドアクリルアマイドアクリルアミド (モノマー) (約50%水溶液)アクリルアミド標準品アクリルアミド,モノマーアクリルアミド.モノマーアクリルアミド 溶液アクリルアミド, 1000 µg/mL in MeOHアクリルアミドaamAcrylamidAcylamide
OptimumAmresco Acryl-40Propenoic acid amideEthylene CarboxamideAmid kyseliny akryloveRCRA waste number U007Acrylamide MonomerDTXSID5020027

データベース識別子

CAS
79-06-1、9003-05-8、9082-06-8、91079-40-2
PubChem CID
6579
DTXSID
DTXSID5020027
ChEMBL
CHEMBL348107
ChEBI
CHEBI:28619
UNII
20R035KLCI
EC Number
201-173-7、293-428-4、618-657-2
Nikkaji
J2.408B

物性

構造計算による物性

XLogP
-0.7
極性表面積
43.1 Ų
水素結合供与体数
1
水素結合受容体数
1
回転可能結合数
1
重原子数
5

実験および物理化学的性質

Chemical Classes · 2 件

Hazardous Air Pollutants (HAPs)

Carcinogens

PolymersPlastics & Rubber -> Other Monomers
CosmeticsCosmetic ingredients (Acrylamide) -> CIR (Cosmetic Ingredient Review)
pHpH = 5.0-6.5 /50% aqueous solution/
SpringerMaterials PropertiesSchoenflies notation
PesticidesPesticide -> EPA IRIS

物理化学的性質

融点
82 · 82-86 °C(lit.)
沸点
125 °C25 · 125 °C25 mm Hg(lit.)
比重(密度)
1 · 1,322 g/cm3
蒸気密度
2.45 · 2.45 (vs air)
蒸気圧
0.03 mm · 0.03 mm Hg ( 40 °C)
屈折率
1.46 · 1.460

化学的性質

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

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H301: 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.

Danger

H301 (94.8%): Toxic if swallowed [Danger Acute toxicity, oral]

危険有害性情報

Regulatory Information · 6 件

Chemical: 2-Propenamide

Hazard Traits - Carcinogenicity; Dermatotoxicity; Developmental Toxicity; Genotoxicity; Hematotoxicity; Neurotoxicity; Reproductive Toxicity; Respiratory Toxicity

Regulation (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/15534

Restricted substance: Acrylamide

Other Safety InformationPEC / SN / Other assessments - Acrylamide: Health and Environment
DOT Label · 3 件

Poison

Poison

Flammable Liquid

Fire Hazards · 6 件

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 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.

Fire PotentialCombustible solid.
Health Hazards · 5 件

Classified as very toxic; probable 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 CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

安全と保護具

Fire Fighting · 4 件

Fight fire from maximum distance. Dike fire control water for later disposal; do 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.

First Aid Measures · 4 件

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.

Accidental Release Measures · 4 件

· 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.

· 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.

First Aid · 6 件

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:

(General first aid procedures)

Safe StorageSeparated from incompatible materials. See Chemical Dangers. Cool. Keep in the dark. Well closed. Store in an area without drain or sewer access.
Firefighting HazardsClosed containers may rupture violently when heated.

毒性情報

Toxicological InformationCDC-ATSDR Toxicological Profile
Treatment · 1 件

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 · 2 件

Endocrine

[in animals: tumors of the lungs, testes, thyroid & adrenal glands]

Interactions · 5 件

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/d; CU: 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.

Target Organs · 3 件

Cancer, Neurological (Nervous System), Reproductive (Producing Children)

Nervous

Eyes, skin, central nervous system, peripheral nervous system, reproductive system

Health EffectsAcrylamide 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)

法規制情報

FDA RequirementsHomopolymers and copolymers of acrylamide are indirect food additives for use only as a component of adhesives. /Homopolymers and copolymers of acrylamide/
RCRA Requirements · 1 件

U007; As 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 Requirements · 1 件

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: 10/4/82; Sunset date: 10/4/92.

Atmospheric Standards · 2 件

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 Reportable Quantities · 2 件

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 microns; or is handled in solution or in molten form; or 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 ... .

State Drinking Water Guidelines · 3 件

(AZ) ARIZONA 0.01 ug/L

(FL) FLORIDA 1 ug/L

(ME) MAINE 0.08 ug/L

安全データ

F
8-10
OEB
D
OEL
TWA: 0.03 mg/m3 [skin]
wgk
3
IDLA
60 mg/m3
tsca
TSCA listed

毒性と防護

毒性アクリルアミド単量体は毒性が強く,皮膚からも吸収され,中枢神経麻ひ症状を引き起こす.LD50 170 mg/kg(マウス,経口).

化学と産業

薬理情報

Mechanism of Action · 2 件

... In this study, we first investigated the effects of acrylamide (ACR) on slow axonal transport of neurofilaments in cultured rat dorsal root ganglia (DRG) neurons through live-cell imaging approach. Then for the underlying mechanisms exploration, the protein level of neurofilament subunits, motor proteins kinesin and dynein, and dynamitin subunit of dynactin in DRG neurons were assessed by western blotting and the concentrations of ATP was detected using the ATP Assay Kit. The results showed that ACR treatment results in a dose-dependent decrease of slow axonal transport of neurofilaments. Furthermore, ACR intoxication significantly increases the protein levels of the three neurofilament subunits (NF-L, NF-M, NF-H), kinesin, dynein, and dynamitin subunit of dynactin in DRG neurons. In addition, ATP level decreased significantly in ACR-treated DRG neurons. Our findings indicate that ACR exposure retards slow axonal transport of NF-M, and suggest that the increase of neurofilament cargoes, motor proteins, dynamitin of dynactin, and the inadequate ATP supply contribute to the ACR-induced retardation of slow axonal transport.

Acrylamide produces a central-peripheral distal axonopathy when administered chronically. This is characterized functionally by decreases in the monosynaptic reflex and dorsal root potential and alterations in the characteristics of the dorsal root reflex. Acute administration of acrylamide inhibits the oxidative enzyme complex nicotinamide adenine dinucleotide (reduced form)-tetrazolium reductase and slows retrograde axoplasmic transport. This study was carried out to determine if the spinal cord reflexes are also affected following acute administration of acrylamide. Dose response studies revealed a dose-dependent increase in both the monosynaptic reflex and dorsal root reflex. A single injection of 50 mg/kg acrylamide caused an increase in both the monosynaptic reflex and dorsal root reflex within 15 min and continued for over 3 hr. These data are paradoxical since chronic administration of acrylamide results in decreased function. Two possible mechanisms are proposed. First, calcium ion regulation may be involved in both the acute and chronic effects of acrylamide on spinal cord reflexes. Second, a depolarization of the neurons is occurring just prior to cell injury or death.

Biological Half-Life · 5 件

Plasma (animal studies): 2 days; whole body (animal studies): 6-18 days; [TDR, p. 40]

Acrylamide elimination is biphasic with an alpha half-life of less than 5 hours and a beta half-life of 6 to 8 days.

The distribution and metabolism of 2,3-(14)C-labeled acrylamide were studied in male rats. Three dose levels of acrylamide (1.0, 10, or 100 mg/kg) were administered orally. ... Elimination of the radiolabel from most tissues was biphasic with a terminal half-life of approx 8 days. The amount of (14)C in blood remained constant at 12% of the dose for about 7 days. However, (14)C in plasma was eliminated readily. The concn-time curve of parent acrylamide in tissues and blood fit a monoexponential curve with a half-life of approx 2 hr.

Elimination from the tissues occurs in two phases: in the first phase its half-life is 5 hr, and in the second (delayed) phase, 8 days or less.

The excretion half-life of parent acrylamide in rat urine was 7.8 hr. Using [1-14C]-acrylamide, ... /it was reported/ that approx 6% of the dose was exhaled as /carbon dioxide/. In an extensive study of the kinetics of both orally and iv admin [2,3-14C]-acrylamide, it was shown that the rate of elimination of the radiolabel in urine was independent of the route of admin. Within 24 hr, about 2/3 of the dose was excreted in the urine and 3/4 in 7 days. Fecal excretion was small (4.8% in 24 hr and 6% by 7 days). Since 15% of the dose appeared in the bile within 6 hr, acrylamide or its derivatives must undergo enterohepatic circulation. Thus, approx 80% of the radiolabel was excreted within 7 days and, of this, a very large proportion (90%) was in the form of metabolites.

Metabolism/Metabolites · 6 件

Acrylamide is primarily (90 to 95%) excreted in the urine as conjugated metabolite with less then 2% parent compound appearing in the urine. Smaller amounts of metabolites are also present in feces, bile, and other biological matrices, still with only small amounts being eliminated as unchanged parent. Acrylamide elimination is biphasic with an alpha half-life of less than 5 hours and a beta half-life of 6 to 8 days.

Urinary metabolites among acrylamide-exposed animals were identified as N-acetyl-S- (3-amino-3-oxopropyl) cysteine (the N-acetyl-cysteine conjugate of acrylamide, following glutathione conjugation accounting for 67% of the total urinary metabolites found in rats, 41% of the total found in mice), N-acetyl-S- (3-amino-2-hydroxy-3-oxopropyl) cysteine (16% in rats, 21% in mice), N-acetyl-S- (1-carbamoyl-2-hydroxyethyl) cysteine (9% in rats, 12% in mice), glycidamide (6% in rats, 17% in mice), 2,3-dihydroxy-propionamide (2% in rats, 5% in mice), and a small amount of the parent compound (which was not possible to quantify).

... In the present study, a low-dose of acrylamide (ACR; 18 mg/kg) was administered to male Wistar rats for 40 days. Ultra performance liquid chromatography/time of flight mass spectrometry (UPLC-Q-TOF MS) was used to examine urine samples from ACR-dosed and control animals. Multiple statistical analyses with principal component analysis (PCA) were used to investigate metabolite profile changes in urine samples, and to screen for potential neurotoxicity biomarkers. PCA showed differences between the ACR-dosed and control groups 20 days after the start of dosing; a bigger separation between the two groups was seen after dosing for 40 days. Levels of 4-guanidinobutanoic acid and 2-oxoarginine were significantly higher in urine from the ACR-dosed group than in urine from the control group after 10 days (p<0.05). Receiver operator characteristic (ROC) curve analysis suggested that 4-guanidinobutanoic acid and 2-oxoarginine were the major metabolites. Our results suggest that high levels of 4-guanidinobutanoic acid and 2-oxoarginine may be related to ACR neurotoxicity. These metabolites could, therefore, act as sensitive biomarkers for ACR exposure and be useful for investigating toxic mechanisms. They may also provide a scientific foundation for assessing the effects of chronic low-dose ACR exposure on human health.

To study the toxic effect of chronic exposure to acrylamide (AA) at low-dose levels, we applied a metabolomics approach based on ultra-performance liquid chromatography/mass spectrometry (UPLC-MS). A total of 40 male Wistar rats were randomly assigned to different groups: control, low-dose AA (0.2 mg/kg bw), middle-dose AA (1 mg/kg bw) and high-dose AA (5 mg/kg bw). The rats continuously received AA via drinking water for 16 weeks. Rat urine samples were collected at different time points for measurement of metabolomic profiles. Thirteen metabolites, including the biomarkers of AA exposure (AAMA, GAMA and iso-GAMA), were identified from the metabolomic profiles of rat urine. Compared with the control group, the treated groups showed significantly increased intensities of GAMA, AAMA, iso-GAMA, vinylacetylglycine, 1-salicylate glucuronide, PE (20:1(11Z)/14:0), cysteic acid, L-cysteine, p-cresol sulfate and 7-ketodeoxycholic acid, as well as decreased intensities of 3-acetamidobutanal, 2-indolecarboxylic acid and kynurenic acid in rat urine. Notably, three new candidate biomarkers (p-cresol sulfate, 7-ketodeoxycholic acid and 1-salicylate glucuronide) in rat urine exposed to AA have been found in this study. The results indicate exposure to AA disrupts the metabolism of lipids and amino acids, induces oxidative stress.

For more Metabolism/Metabolites (Complete) data for ACRYLAMIDE (8 total), please visit the HSDB record page.

Acrylamide is absorbed following oral, inhalation, and dermal exposure and is widely distributed, tending to accumulate in the red blood cells. In the proposed major metabolic pathway acrylamide reacts with glutathione to form S-beta-propionamide glutathione conjugate which is excreted in the urine as cysteine or N-acetylcysteine derivatives. The major urinary metabolite (accounting for 48% of the excreted dose) is N-acetylcysteine-S-beta-propionamide. Alternately, acrylamide may be oxidized to glycidamide by CYP2E1. Glycidamide then goes on to form similar glutathione conjugates or undergos hydrolysis, leading to the formation of 2,3-dihydroxypropionamide and 2,3-dihydroxypropionicacid. (A635, A324, L1887)

Absorption, Distribution and Excretion · 5 件

Acrylamide is well absorbed after oral, dermal, inhalational, and parenteral exposure, including through intact skin and mucous membranes. Efficient absorption of this compound is demonstrated by the observation that peak blood concentrations occur at approximately 1 hour after exposure. It is estimated that human elimination rates of acrylamide are only one-fifth that seen in rats.

Acrylamide is primarily (90 to 95%) excreted in the urine as conjugated metabolite with less then 2% parent compound appearing in the urine. Smaller amounts of metabolites are also present in feces, bile, and other biological matrices, still with only small amounts being eliminated as unchanged parent. Acrylamide elimination is biphasic with an alpha half-life of less than 5 hours and a beta half-life of 6 to 8 days.

In rats given 0.5-100 mg/kg bw of either (1-14(C))- or (2,3-14(C))acrylamide intravenously or orally, radioactivity was distributed rapidly throughout the body, with no selective accumulation in any tissue. Radioactivity was also distributed evenly among tissues of beagle dogs and miniature pigs

... Can be absorbed through ... mucous membranes and lungs as well as the GI tract.

For more Absorption, Distribution and Excretion (Complete) data for ACRYLAMIDE (14 total), please visit the HSDB record page.

用途と製造

Uses · 6 件

CIR ingredient: Acrylamide

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.

Used as a polymer or copolymer to produce sealants, adhesives, fibers, paper sizing, molded parts, water coagulants, and textiles. In the United States, 90% of acrylamide is used to produce polyacrylamide for water treatment (60%), pulp and paper production (20%) and mineral processing (10%); [ACGIH]

Pulp and Paper Processing [Category: Industry]

For acrylamide (USEPA/OPP Pesticide Code: 600008) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

It 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.

ImpuritiesPossible contaminants include sodium sulfate, acrylic acid, sulfuric acid, and water, depending on the mode of synthesis. The commercial product has been reported to contain residual levels of 1-100 mg/kg acrylonitrile.
U.S. Exports(1972) NEGLIGIBLE
U.S. Imports(1972) NEGLIGIBLE
U.S. Production · 5 件

2023: 400,000,000 - <550,000,000 lb

(1972) 1.45X10+10 G

(1975) GREATER THAN 9.08X10+5 G

(1983) 86,233 lb

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 2-Propenamide. National Production Volume: 296,109,253 lb/yr.

Consumption Patterns · 5 件

40% FOR POLYACRYLAMIDES USED IN THE WATER TREATMENT INDUSTRY; 20% FOR POLYACRYLAMIDES USED IN THE PULP AND PAPER INDUSTRY; 40% FOR POLYACRYLAMIDES USED IN MISC APPLICATIONS INCL DRILLING MUD ADDITIVES, TEXTILE TREATMENT, SURFACE COATINGS (1973)

45% FOR WATER TREATMENT, 20% FOR OIL DRILLING, 20% FOR PULP AND PAPER, 10% FOR MINERAL PROCESSING, 5% OTHER (1984)

Water treatment, 45%; oil drilling, 20%; pulp and paper, 20%; mineral processing, 10%; other, 5%.

Demand: 1987: 110 million lb; 1988 /projected/: 100 million lb; 1992 /projected/: 120 million lb (Includes imports of 15 to 20 million lb in 1987; exports are negligible).

For more Consumption Patterns (Complete) data for ACRYLAMIDE (6 total), please visit the HSDB record page.

応用分野 · 7 件

解説アクリルアミド,融点85.5 ℃,沸点87 ℃(267 Pa).d425"1.127.水,メタノール,エタノール,アセトン,酢酸エチルに可溶.光,熱により重合しやすいので,冷暗所に保存する.重合方法により水に不溶のポリマーも水溶性ポリマーも合成できる.ポリマーは,接着剤,分散剤,紙や繊維などの仕上げ剤,塗料,凝集沈殿促進剤などに用いられる.森北出版「化学辞典(第2版)

用途合成繊維、樹脂添加剤

用途紙力増強剤?凝集剤重合原料、繊維加工剤、接着剤性能向上加工剤、化粧品原料、アクリル系熱硬化性塗料合成原料、凝集剤?土壌改良剤?紙力増強剤?接着剤原料

説明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.

使用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.

一般的な説明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.

使用用途アクリルアミドは、ほぼ全量がアクリルアミドポリマー (ポリアクリルアミド) の原料として使用されています。アクリルアミドがそのまま別の用途に使用されるケースとしては、他のポリマーに少量モノマー成分として使用される以外はほとんどありません。なお、クリルアミドポリマーの使用用途は以下のとおりです。 1. 凝集剤 ポリアクリルアミドは、汚水処理などで凝集剤として利用されます。 2. 接着剤 ポリアクリルアミドは、の原料としても利用されます。 3. 農業分野 ポリアクリルアミドは土壌改良用途用、特に土壌の保水性や透水性を改善するため、農業分野で利用されています。 4. 医療分野 ポリアクリルアミドは、医療用品などの原料としても使用されます。 5. その他 アクリルアミドポリマーは、紙力増強剤や繊維加工、漏水防止剤、染料、UV塗料、レンズ材料など、シェービングジェルや整髪剤などの化粧品にも利用されます。

調製方法 · 3 件

製造方法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.

製造方法を酸触媒 (やなど) の存在下で加水分解する方法です。この反応は以下のように表されます。 CH2=CHCN + H2O → CH2=CHCONH2 この反応では、アクリロニトリルと水が反応してアクリルアミドが生成します。また、酸触媒によってニトリル基の加水分解が促進されます。 その他、アクリロニトリルの加水分解反応をニトリルヒドラーゼという微生物由来の酵素を用いて合成することも可能です。ニトリルヒドラーゼはニトリルを加水分解する酵素で、製造効率の観点で優れているため、工業的にも採用されています。 参考文献

純化方法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. [Dawson et al. Data for Biochemical Research, Oxford Press 1986 p. 449, Beilstein 2 IV 1471.] CAUTION: Acrylamide is extremely TOXIC (neurotoxic), and precautions must be taken to avoid skin contact or inhalation. Use gloves and handle in a well-ventilated fume cupboard.

上流・下流製品情報

下流製品

補足説明

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

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