アクリルアミド
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
識別子と物理属性
| CAS No. | 79-06-1 |
|---|---|
| 分子式 | C3H5NO |
| 平均分子量 | 71.08 g/mol |
| 単同位体質量 | 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 |
| 現地名 | アクリルアミド |
化学・物理的性質
| XLogP | -0.7 |
|---|---|
| 極性表面積 | 43.1 |
| 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 |
| 形式電荷 | 0 |
| 複雑度 | 57.9 |
| 物質分類 | Hazardous Air Pollutants (HAPs)Carcinogens |
| Polymers | Plastics & Rubber -> Other Monomers |
| 化粧品 | 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 |
| 農薬 | Pesticide -> EPA IRIS |
| LogP（分配係数） | log Kow = -0.67-0.78 |
| 臭い | Odorless無臭の固体 |
| 密度 | 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 |
| 溶解度 | 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)2040g/L（25℃）水中のアクリルアミドの従来の試験濃度は 250 mg/mL であり、透明な無色の溶液が得られます。水への溶解度は少なくとも 40% (w/v) で、30°C の水で 215g/100mL と報告されています。 |
| 融点 | 82-86 °C(lit.) |
| 沸点 | 125 °C25 mm Hg(lit.) |
| 蒸気密度 | 2.45 (vs air) |
| 蒸気圧 | 0.03 mm Hg ( 40 °C) |
| 屈折率 | 1.460 |
| 引火点 | 138 °C |
| 貯蔵条件 | 2-8°C |
| 外観・状態 | 粉 |
| pKa（酸解離定数） | 15.35±0.50(Predicted) |
| 色 | 白い |
| Merck | 14,129 |
| BRN | 605349 |
| ヘンリー定数 | (x 10-9 atmm3/mol): 3.03 at 20 °C (approximate - calculated from water solubility and vapor pressure) |
| 安定性 | 不安定。 50℃以上に加熱しないでください。爆発的。酸、塩基、酸化剤、還元剤、鉄および鉄塩、銅、アルミニウム、真鍮、フリーラジカル開始剤とは相容れない。空気に敏感。吸湿性。 |
| 主な用途 | 洗浄剤化粧品環境食品および飲料パーソナルケア |
| InChI | 1S/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5) |
| InChIKey | HRPVXLWXLXDGHG-UHFFFAOYSA-N |
| SMILES | NC(=O)C=C |
| LogP（分配係数） | -0.9 at 20℃ and pH7 |
| CAS データベース | 79-06-1(CAS DataBase Reference) |
| NISTの化学物質情報 | Acrylamide(79-06-1) |
| EPAの化学物質情報 | Acrylamide (79-06-1) |
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.
安全性と法規制
| GHS 分類 | 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] |
|---|---|
| 規制情報 | 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 |
| その他の安全情報 | PEC / SN / Other assessments - Acrylamide: Health and Environment |
| 輸送ラベル（DOT） | PoisonFlammable Liquid |
| 火災危険 | 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. |
| 火災の可能性 |
用途
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.
製法・合成法
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.