1,4-Butanediol vinyl ether Chemical Properties

Melting point:

-33 °C

Boiling point:

95 °C/20 mmHg (lit.)

Density 

0.939 g/mL at 25 °C (lit.)

vapor pressure 

0.3 hPa (20 °C)

refractive index 

n20/D 1.444(lit.)

Flash point:

185 °F

storage temp. 

Store at <= 20°C.

solubility 

75g/l

pka

15.04±0.10(Predicted)

form 

clear liquid

color 

Colorless to Light yellow

Specific Gravity

0.93

explosive limit

1.4-9.9%(V)

Water Solubility 

75 g/L (20 ºC)

LogP

0.43 at 25℃

CAS DataBase Reference

17832-28-9(CAS DataBase Reference)

EPA Substance Registry System

1-Butanol, 4-(ethenyloxy)- (17832-28-9)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38-22-52/53

Safety Statements 

26-36-24/25-61

RIDADR 

NA 1993 / PGIII

WGK Germany 

1

Autoignition Temperature

225 °C DIN 51794

HS Code 

2909 49 80

Toxicity

LD50 orally in Rabbit: 1738 mg/kg LD50 dermal Rat > 2000 mg/kg

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

1,4-Butanediol vinyl ether Usage And Synthesis

Chemical Properties

1,4-Butanediol vinyl ether (HBVE; 4-Hydroxybutyl vinyl ether) is a colorless or light yellow transparent liquid with a slight odor similar to ether. It is miscible with alcohols, ethers, esters and aromatic hydrocarbons.

Synthesis

1,4-Butanediol vinyl ether is prepared by reacting acetylene and 1,4-butanediol in the presence of potassium hydroxide and potassium alkoxide catalyst:        Since 1,4-butanediol contains two hydroxyl groups and the product contains active vinyl ether functional groups, some side reactions will occur. For example, further reaction of HBVE with acetylene to generate divinyl ether, and self-condensation reaction of HBVE to form a cyclic acetal. A superbase catalytic system CsF–NaOH was developed for the preparation of HBVE at a temperature of 138–14 °C and under initial acetylene pressure of 1.0–1.2 MPa. The conversion of 1,4-butanediol was 100% and the total yield of the vinyl ethers was 80% at catalyst dosage (7 mol% CsF and 7 mol% NaOH based on 1,4-butanediol) and after reaction for 3 h. Some researchers also developed heterogeneous catalysts for the reaction of acetylene and 1,4-butanediol to obtain HBVE. Potassium hydroxide was supported on carriers such as aluminum oxide, molecular sieves, silica gel and zirconia.

Reactivity Profile

The structure of the 1,4-Butanediol vinyl ether (HBVE) is a vinyl double bond directly connected with an ether bond, and due to the influence of an adjacent oxygen atom, the double bond is an electron-rich double bond and shows higher reactivity. HBVE also has a hydroxyl, and can react with a series of resins. It has wide application in fluororesin and coatings.

Flammability and Explosibility

Flammable

1,4-Butanediol vinyl ether(17832-28-9)Related Product Information

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