Бензилглицидиловый эфир

Description

Benzylglycidyl ether is a glycidyl derivative, a monofunctional glycidyl ether of benzyl alcohol. Formula C10H12O2, CAS number 2930-05-4, synonyms 1-benzyloxy-2,3-epoxypropane, benzyl-2,3-epoxypropyl ether.

Basic Attributes

• Chemical formula: C10H12O2
• Molecular weight: 164.2
• Exact weight: 164.20
• EU number: 220-899-5
• HS code: 29329990
• PSA specifications: 21.8
• XLogP3: 1.3

Physico-chemical characteristics

• Color/shape: colorless to light yellow
• Density: 1.077 g/ml at 25 °C (lit.)
• Melting point: 89.5-90.1 °C
• Boiling point: 70-73 °C at 11 mmHg. Art.
• Flash point: >230°F
• Refractive index: n20/D 1.5170 (lit.)
• Storage conditions: refrigerator, critical temperature 2-8 °C

Synthesis and reactivity

Rac-/(R)-benzylglycidyl ether is used in the synthesis of atactic and isotactic linear polycarbonates based on benzyl-1,2-glycerol carbonate. Biocatalytic cleavage of racemic benzylglycidyl ether by the fungus Talaromyces flavus has been described, as well as enzymatic cleavage to (S)-benzylglycidyl ether with 30% enantiomeric excess and (R)-3-benzyloxypropane-1,2-diol with 40% enantiomeric excess by Bacillus alcalophilus cells - these reactions are used to obtain optically active derivatives from racemic mixtures. The compound also reacts with the K⁻, K⁺(15-crown-5)₂ system to form potassium glycide oxide and bibenzyl.

Scope of application

As a monofunctional glycidyl ether, the compound is used as an active diluent for epoxy resins: one epoxy group reduces the viscosity of the composition and participates in the curing reaction without forming additional crosslinks, which improves the processability of coatings and casting compounds. The presence of a chiral center at the epoxy carbon atom also makes the substance a convenient starting compound for asymmetric synthesis through kinetic enzymatic separation of enantiomers.

Storage conditions

Store in the refrigerator at a temperature of 2-8 °C, in a tightly closed container, protected from moisture and light - the epoxy ring is reactive and opens under the influence of nucleophiles, acids and bases even at room temperature.

Comparison with other glycidyl ethers

Compared to bifunctional glycidyl ethers, such as bisphenol A diglycidyl ether, monofunctional benzyl glycidyl ether does not create additional crosslinks during the curing of the epoxy composition, so it is used specifically as a viscosity and flexibility modifier, and not as a primary crosslinking agent. This functional selectivity makes it a convenient component in formulations where it is important to maintain a controlled crosslink density while reducing the process viscosity of the composition.

This approach is in demand in the production of casting compounds in the electronics industry.