4-hydroxybutanal

4-hydroxybutanal Property

Boiling point:

103.07°C (rough estimate)

Density 

1.0808

refractive index 

1.4384

storage temp. 

Refrigerator

solubility 

Chloroform (Sparingly), Ethyl Acetate (Slightly)

form 

Oil

pka

14.89±0.10(Predicted)

color 

Colourless

Stability:

Hygroscopic

EPA Substance Registry System

Butanal, 4-hydroxy- (25714-71-0)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

4-hydroxybutanal Chemical Properties,Usage,Production

Uses

4-Hydroxybutanal is used in preparation of deoxykeoses and acetonides. 4-Hydroxybutanal is also a metabolite of Tegafur , a prodrug used for various cancer chemotherapies.

Reactions

4-Hydroxybutanal forms a cyclic hemiacetal when the hydroxyl oxygen add to the aldehyde group. Methanol reacts with this cyclic hemiacetal to form 2-methoxytetrahydrofuran which is our desired product.2-Methoxytetrahydrofuran is a cyclic acetal. The hydroxyl oxygen of 4-Hydroxybutanal reacts with the aldehyde to form cyclic ether linkage.

Synthesis

The 4-hydroxybutanal which is produced as the high yield product of the invention hydroformylation process can be separated and recovered by conventional distillation procedures. It is highly preferred, however, to subject the hydroformylation product mixture to aqueous phase extraction. Surprisingly it was found that water is capable of extracting 4-hydroxybutanal from the product mixture substantially to the exclusion of the other product mixture components. In a commercial scale operation, an aqueous phase stream can be contacted countercurrently and continuously with reaction product effluent from the hydroformylation reaction zone. The resultant aqueous phase containing 4-hydroxybutanal is an excellent vehicle for subsequent processing procedures, such as hydrogenation of 4-hydroxybutanal with Raney nickel to produce valuable 1,4-butanediol.
literature source US04064145

References

[1] QINGYONG MENG Ming B H Chenggen Zhang. A theoretical model study on the cyclic reaction of 4-hydroxybutanal catalyzed by Br?nsted acid[J]. Canadian Journal of Chemistry, 2009, 68 1: 1610-1619. DOI:10.1139/V09-126.
[2] LUDMILA LEITE. Transformation of 4-hydroxybutanal over porcelain[J]. Journal of Molecular Catalysis A: Chemical, 1999, 144 2: Pages 323-328. DOI:10.1016/S1381-1169(98)00382-3.
[3] https://patents.google.com/patent/CN114149312A/en