基本情報
- CAS
2873-97-4- 標準SMILES
C=CC(=O)NC(C)(C)CC(C)=O- InChIKey
OMNKZBIFPJNNIO-UHFFFAOYSA-N- 分子式
- C9H15NO2
- 平均分子量
- 169.22 g/mol
- 単同位体質量
- 169.11027872
名称と識別子
- 優先名称
- N-(1,1-Dimethyl-3-oxobutyl)acrylamide
- IUPAC
- N-(2-methyl-4-oxopentan-2-yl)prop-2-enamide
- 現地名
- ジアセトンアクリルアミド
- 英語名
- Diacetone acrylamide
- 分子式
- C9H15NO2
- 分子量
- 169.22
名称と別名
名称をさらに表示
データベース識別子
- CAS
2873-97-4- PubChem CID
- 17888
- DTXSID
DTXSID1024916- ChEMBL
CHEMBL3183854- UNII
- 3Z8J3430Z2
- EC Number
- 220-713-2
- Nikkaji
- J7.924C
物性
構造計算による物性
- XLogP
- 0.4
- 極性表面積
- 46.2 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 2
- 回転可能結合数
- 4
- 重原子数
- 12
- 形式電荷
- 0
- 複雑度
- 207
実験および物理化学的性質
Solubility
Very soluble (NTP, 1992)
Highly sol in water and most organic solvents
Soluble in chloroform
Boiling Point
248 °F at 8 mmHg (NTP, 1992)
120 °C @ 8 mm Hg
Melting Point
135 to 136 °F (NTP, 1992)
57-58 °C
Physical Description
Diacetone acrylamide appears as white crystals. (NTP, 1992)
Large Crystals; Dry Powder; Liquid
White hygroscopic solid; [Merck Index] White or yellow crystalline solid; [MSDSonline]
Stability/Shelf Life
HAS LONG SHELF LIFE; SHOWS NO POLYMERIZATION ON PROLONGED STORAGE.
50% NEUTRAL WATER SOLN IS STABLE @ PH 7.5-7.7 FOR UP TO 6 MO; HIGHLY REACTIVE VINYL MONOMER.
物理化学的性質
- 融点
- 54 · 54-56 °C (lit.)
- 沸点
- 120 °C · 120 °C (8 mmHg)
- 比重(密度)
- 1.0873 · 1.0873 (rough estimate)
- 蒸気圧
- 0.109 Pa · 0.109Pa at 20℃
- 屈折率
- 1.42 · 1.4200 (estimate)
- 闪点
- 230 °F · >230 °F
- 貯蔵温度
- Inert atmosphere,Room Temperature
- 酸解離定数(Pka)
- 14.12 · 14.12±0.46(Predicted)
- 外見
- 結晶性粉末またはフレーク
- 色
- ホワイト~クリーム
- 水溶解度
- 溶ける
- Merck
- 14 · 14,2963
- BRN
- 1928444 · 1928444
- InChI
- 1S/C9H15NO2/c1-5-8(12)10-9(3,4)6-7(2)11/h5H,1,6H2,2-4H3,(H,10,12)
- InChIKey
- OMNKZBIFPJNNIO-UHFFFAOYSA-N
- SMILES
- CC(=O)CC(C)(C)NC(=O)C=C
- LogP
- 0.321 at · 0.321 at 21℃
- CAS データベース
- 2873 · 2873-97-4(CAS DataBase Reference)
- NISTの化学物質情報
- 2 · 2-Propenamide, n-(1,1-dimethyl-3-oxobutyl)-(2873-97-4)
- EPAの化学物質情報
- N-(1,1-Dimethyl-3-oxobutyl)acrylamide (2873-97-4)
化学的性質
化学的特性Diacetone acrylamide is a white to cream crystalline powder or flakes, it may undergo autoxidation upon exposure to the air to form explosive peroxides.
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 18% (65 of 362) of reports.
Warning
H302 (82%): Harmful if swallowed [Warning Acute toxicity, oral];H361 (49.4%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 362 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 65 of 362 reports by companies.;There are 6 notifications provided by 297 of 362 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
危険有害性情報
Regulatory Information
Chemical: 2-Propenamide, N-(1,1-dimethyl-3-oxobutyl)-
2-Propenamide, N-(1,1-dimethyl-3-oxobutyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenamide, N-(1,1-dimethyl-3-oxobutyl)- 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: 22-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13212
2-Propenamide, N-(1,1-dimethyl-3-oxobutyl)-: Does not have an individual approval but may be used under an appropriate group standard
Reactivity Profile
DIACETONE ACRYLAMIDE forms polymers in solution, in bulk, or in emulsion. May react vigorously with strong oxidizing agents. Can react exothermically with reducing agents (such as alkali metals and hydrides) to release gaseous hydrogen. May react exothermically with both acids and bases. May undergo autoxidation upon exposure to the air to form explosive peroxides.
Hazard Classes and Categories
Acute Tox. 4 (82%);Repr. 2 (49.4%)
Acute toxicity (Oral) - Category 4
安全と保護具
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.;STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter.;RECOMMENDED GLOVE MATERIALS: Permeation data indicate that butyl rubber gloves may provide protection to contact with this compound. Butyl rubber over latex gloves is recommended. However, if this chemical makes direct contact with your gloves, or if a tear, hole or puncture develops, remove them at once. (NTP, 1992)
毒性情報
Antidote and Emergency Treatment
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
Non-Human Toxicity Values
LD50 Rat oral 1770 mg/kg
LD50 Mouse oral 1303 mg/kg
法規制情報
Regulatory Information
Chemical: 2-Propenamide, N-(1,1-dimethyl-3-oxobutyl)-
2-Propenamide, N-(1,1-dimethyl-3-oxobutyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenamide, N-(1,1-dimethyl-3-oxobutyl)- 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: 22-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13212
2-Propenamide, N-(1,1-dimethyl-3-oxobutyl)-: Does not have an individual approval but may be used under an appropriate group standard
安全データ
- F
- 3
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- AS3475000
- 毒性
- LD50 orally in mice: 7.7 mmol/kg (Hashimoto)
- hs_code
- 29241990
- risk_code
- 22
- 化審法
- (2)-1024
- hazard_code
- Xn
- safety_code
- 23-24/25
- Hazard Classifications
- Acute Tox. 4 Oral
- ストレージクラス
- 11 - Combustible Solids
- 有毒物質データの
- 2873-97-4(Hazardous Substances Data)
化学と産業
用途と製造
Uses
Used to make coatings, laminates, sealers, adhesives, and lubricating oils; to impart water tolerance and vapor permeability to copolymer films; as cross-linking agent in polyester resins; in color photography; in orthopedic bandages; in air sprays; [HSDB] Used as adhesion improver for cellulosics, concrete, and glass; [Hawley]
Textiles (Fiber & Fabric Manufacturing) [Category: Industry];Plastic Composites Manufacturing [Category: Industry];Photographic Processing [Category: Other];Cement Producing [Category: Industry];Glass Manufacturing [Category: Industry]
In mfr of coatings, laminates, sealers, adhesives, lubricating oils
Imparts water tolerance and vapor permeability to copolymer films; cross-linking agent in polyester resins; color photography
ORTHOPEDIC BANDAGE COMPRISING DIACETONE ACRYLAMIDE
IN AIR SPRAYS
U.S. Production
2023: 1,000,000 - <2,500,000 lb;2022: 1,000,000 - <5,000,000 lb;2021: 1,000,000 - <2,500,000 lb;2020: 1,000,000 - <5,000,000 lb
(1977) NOT PRODUCED COMMERCIALLY IN US
(1979) NOT PRODUCED COMMERCIALLY IN US
Methods of Manufacturing
REACTION OF ACRYLONITRILE WITH ACETONE IN PRESENCE OF CONCENTRATED SULFURIC ACID; REACTION OF ACRYLONITRILE WITH 1,1-DIMETHYL-3-OXOBUTANOL VIA RITTER REACTION
Prepd by reaction of acrylonitrile with acetone in presence of concn sulfuric acid: Coleman et al, J Polym Sci 3a, 1601 (1965); Coleman, US patent 3,277,056 (1966 to Lubrizol).
N-Substituted acrylamides may also be prepared from acetylene, carbon monoxide, and an amine using an iron or nickel carbonyl catalyst.
General Manufacturing Information
Paint and Coating Manufacturing;Plastics Material and Resin Manufacturing;Not Known or Reasonably Ascertainable
2-Propenamide, N-(1,1-dimethyl-3-oxobutyl)-: ACTIVE
Similar to acrylic esters in polymerization behavior. Forms high mol wt polymers in bulk, soln, or emulsion. Esp suitable for electropolymerization.
応用分野
用途コーティング剤、ラミネート剤、シール剤、接着剤、潤滑油等の製造、ホモポリマーは耐紫外線性の親水性、ただし非水溶性のポリマーとして用いられる。また、各種ビニルモノマーと共重合させて耐紫外線性、吸湿性、極性官能基を付与した機能性ポリマーになる。コンタクトレンズ用ポリマーとしてメタクリル酸2-ヒドロキシエスチルに4%量共重合させて軟質化する。
用途DAAM(ダイアセトンアクリルアミド)は各種コーティング剤(常温架橋型)、繊維処理剤、紙処理剤、感光性樹脂、ヘアスプレー用、接着剤、架橋剤、樹脂改質剤などに使用されます。 応用例と改良点は以下の通りです。 ■塗料分野 架橋剤(ジヒドラジド)を用いる事により、耐水性、耐アルコール性が補強され、密着性に優れる光沢の良い塗膜が得られます。 ■接着剤 接着性強度アップが図れます。 ■感光剤分野(ポリエステル系) 露光後の硬度、可撓性、耐水性に優れた版材が得られます。 ■ホモポリマーは吸湿、吸水性、ガス透過性を示します。
用途有機合成原料。
使用Diacetone acrylamide is used in epoxy resin, acryl emulsion, water based paints, waste water treatment, photosensitive resins, waterborne coatings and gel electrophoresis. It is also used in the manufacture of permanent press fabrics.
一般的な説明Diacetone acrylamide is a white crystals, it is an acrylic type monomer, used as a crosslinking monomer to make functional copolymers.
上流・下流製品情報
上流原料
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