• Name

  Diacetone acrylamide

• EINECS 220-713-2
• CAS No. 2873-97-4
• Article Data7
• CAS DataBase
• Density 0.965 g/cm³
• Solubility Soluble in water
• Melting Point 54-56 °C(lit.)
• Formula C₉H₁₅NO₂
• Boiling Point 325.9 °C at 760 mmHg
• Molecular Weight 169.224
• Flash Point 139.4 °C
• Transport Information
• Appearance white to cream crystalline powder or flakes
• Safety 23-24/25
• Risk Codes 22
• Molecular Structure
• Hazard Symbols Xn
• Synonyms 2-Propenamide, N,N-bis(2-oxopropyl)-;Acrylamide, N- (1,1-dimethyl-3-oxobutyl)-;Diacetoneacrylamide (DAAM);N-(1, 1-Dimethyl-3-oxobutyl)acrylamide;N-(1, 1-Dimethyl-3-oxobutyl)-2-propenamide;N-(2-(2-Methyl-4-oxopentyl))acrylamide;2-Propenamide,N-(1,1-dimethyl-3-oxobutyl)-;Acrylamide, N, N-diacetonyl-;DAAM (DiAcetone Acrylamide);Diacetone Acrylamide (DAAM);Diacetone acrylamide;2-Propenamide, N- (1,1-dimethyl-3-oxobutyl)-;
• PSA 46.17000
• LogP 1.43720

Diacetoneacrylamide Consensus Reports

Diacetoneacrylamide Specification

1. Introduction of Diacetoneacrylamide
Diacetoneacrylamide is also called N-(1,1-Dimethyl-3-oxobutyl)acrylamide; 2-Propenamide, N,N-bis(2-oxopropyl)- ; 2-Propenamide, N-(1,1-dimethyl-3-oxobutyl)- ; Acrylamide, N,N-diacetonyl- ; Diacetone acrylamide ; N-(1,1-Dimethyl-3-oxobutyl)-2-propenamide ; N-(2-(2-Methyl-4-oxopentyl))acrylamide. The IUPAC Name of it is N-(2-Methyl-4-oxopentan-2-yl)prop-2-enamide.

2. Properties of Diacetoneacrylamide
Melting Point: 54-56 °C(lit.)
Boiling point: 120 °C (8 mmHg)
Flashing point: >230 °F
Water Solubility: soluble
Sensitive: Hygroscopic
Appearance: white to cream crystalline powder or flakes

3. Toxicity of Diacetoneacrylamide

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	oral	1303mg/kg (1303mg/kg)		Archives of Toxicology. Vol. 47, Pg. 179, 1981.
rabbit	LD50	skin	> 10gm/kg (10000mg/kg)		Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 113, 1990.
rat	LD50	oral	1770mg/kg (1770mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 113, 1990.

4. Safety Information of Diacetoneacrylamide
Hazard Codes: Xn
Risk Statements: 22
R22: Harmful if swallowed.
Safety Statements: 23-24/25
S23: Do not breathe vapour. 
S24/25: Avoid contact with skin and eyes.
WGK Germany: 1
RTECS: AS3475000
F:3
Hazardous Substances Data:2873-97-4(Hazardous Substances Data)
Moderately toxic by ingestion. When heated to decomposition it emits toxic fumes of NO_x.

5. Preparation of Diacetoneacrylamide
React acrylonitrile and 4-hydroxy-4-methyl-2-pentanone in the presence of at least 93% sulfuric acid to form a reaction mixture; contacting said reaction mixture with water and with a suitable water-immiscible organic solvent to form a liquid two-phase mixture consisting of an aqueous phase and an organic phase; Neutralizing or alkalizing the aqueous phase with an alkalizing agent; Separating the neutralized or alkalized aqueous phase; and recover N-(1,1-dimethyl-3-oxobutyl)acrylamide from the organic phase, the improvement comprising, between the reaction step and the contacting step: cooling the reaction mixture to about 15° C. and adding a suitable organic solvent thereto, while maintaining the temperature at about 15°-20° C., to precipitate a crystalline intermediate reaction product from said reaction mixture having the formula and washing said intermediate reaction product with a suitable organic solvent to remove oily impurities and sulfuric acid therefrom.

6. Use of Diacetoneacrylamide
Diacetoneacrylamide can be used primarily as a homopolymer and it  also widely used in paint, moisture and good perm and spray tackifier resin, photosensitive resin and its additives.

7. Other details of Diacetoneacrylamide
Chemical Stability: Not available 
Conditions to Avoid: Incompatible materials, exposure to moist air or water. 
Incompatibilities with Other Materials Strong oxidizing agents, strong bases. 
Hazardous Decomposition Products Nitrogen oxides, carbon monoxide, carbon dioxide. 
Hazardous Polymerization Has not been reported. 
First Aid Measures of
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin: Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. 
Ingestion: Get medical aid. Wash mouth out with water. 
Inhalation: Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. 
Handling and Storage:
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. 
Storage: Store in a cool, dry place. Store in a tightly closed container.