Diallyl maleate Chemical Properties

Melting point:

−47 °C(lit.)

Boiling point:

106-116 °C4 mm Hg

Density 

1.074 g/mL at 20 °C(lit.)

vapor density 

6.6 (vs air)

vapor pressure 

4 mm Hg ( 25 °C)

refractive index 

n20/D 1.469(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

form 

clear liquid

color 

Colorless to Almost colorless

Odor

pungent odor

Water Solubility 

Soluble in water 151.2 mg/L @ 25°C.

BRN 

1725954

InChIKey

ZPOLOEWJWXZUSP-WAYWQWQTSA-N

LogP

2.126 (est)

CAS DataBase Reference

999-21-3(CAS DataBase Reference)

EPA Substance Registry System

Diallyl maleate (999-21-3)

Safety Information

Hazard Codes 

Xn

Risk Statements 

21/22-36/37/38-22-20/21

Safety Statements 

26-36/37

RIDADR 

UN 2810 6.1/PG 3

WGK Germany 

3

RTECS 

ON0700000

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29171900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Diallyl maleate Usage And Synthesis

Chemical Properties

colorless liquid with a pungent odor.

Uses

An agent for the promotion of branching in emulsion polymers

Uses

Diallyl maleate has potential applications in polyester resins, adhesives, and ion exchange resins. When used at low levels, Diallyl Maleate is an effective agent for the promotion of branching in emulsion polymers.

Preparation

Diallyl maleate is obtained by the sulfuric acid-catalyzed esterification of maleic anhydride with propyl alcohol.

Safety Profile

Poison by ingestion and intraperitoneal routes. Moderately toxic by skin contact. A skin and eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALLYL COMPOUNDS and ESTERS.

Synthesis

A typical procedure for the synthesis of diallyl maleate from maleic anhydride and acryl alcohol is as follows: maleic anhydride (1 mmol, 0.15 g), acryl alcohol (5 mmol, 0.46 mL, 0.37 g), and HFDAIL as a catalyst (10 mol/mol of maleic anhydride, 0.05 g) were charged into a 50 mL round-bottomed flask equipped with a Dean-Stark device, reflux condenser, and magnetic stirrer in a 50 mL round bottom flask. The reaction mixture was stirred at 125 °C for 7 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) using ethyl acetate/hexane (2:8) as eluent. When TLC showed that the reaction was complete, the isolated product (diallyl maleate) was obtained by extraction with ethyl acetate (3 x 5 mL) and evaporation of ethyl acetate under reduced pressure to give the target product as a yellow oily liquid in 95% yield (0.26 g, boiling point = 340 °C). The resulting product was dried under vacuum at 70 °C for 5 hours. The viscous ionic liquid can be directly reused without further treatment after removing water under vacuum at 80 °C for 5 h. The product was dried under vacuum for 5 h at 70 °C.

References

[1] Journal of Molecular Liquids, 2017, vol. 227, p. 153 - 160
[2] Patent: US2249768, 1939,
[3] Sci. Ind. Osaka, 1958, vol. 32, p. 228
[4] Chem.Abstr., 1959, p. 7007
[5] Patent: US2249768, 1939,

Diallyl maleate(999-21-3)Related Product Information

• DIALLYL MALATE
• DIALLYL MALEATE, (MALEIC ACID DIALLYL ESTER)
• Monomethyl maleate
• Maleic acid
• Diethyl maleate
• Monoethyl maleate
• Diallyl maleate
• 2-Butene-1,4-diol
• ALLYL ACRYLATE
• Dimethyl maleate
• Allyl ether
• DIMETHALLYL MALEATE