1,4-Butanediol vinyl ether

Synonym(s):1,4-Butanediol monovinyl ether;1,4-Butanediolmonovinylether;4-(Ethenyloxy)-1-butanol;4-(Vinyloxy)-1-butanol;4-Hydroxybutyl vinyl ether

CAS NO.：17832-28-9
Empirical Formula: C6H12O2
Molecular Weight: 116.16
MDL number: MFCD00080697
EINECS: 241-793-5
SAFETY DATA SHEET (SDS)
Update Date: 2024-08-21 22:41:43

What is 1,4-Butanediol vinyl ether?

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

Properties of 1,4-Butanediol vinyl ether

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
form	clear liquid
pka	15.04±0.10(Predicted)
Specific Gravity	0.93
color	Colorless to Light yellow
explosive limit	1.4-9.9%(V)
Water Solubility	75 g/L (20 ºC)
CAS DataBase Reference	17832-28-9(CAS DataBase Reference)
EPA Substance Registry System	1-Butanol, 4-(ethenyloxy)- (17832-28-9)

Safety information for 1,4-Butanediol vinyl ether

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H302:Acute toxicity,oral H319:Serious eye damage/eye irritation H412:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes	P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.