Isosorbide dimethyl ether Chemical Properties

Melting point:

-70°C

Boiling point:

93-95 °C0.1 mm Hg(lit.)

Density 

1.15 g/mL at 25 °C(lit.)

vapor pressure 

12.54Pa at 20℃

refractive index 

n20/D 1.461(lit.)

Flash point:

227 °F

storage temp. 

Sealed in dry,Room Temperature

form 

Liquid

color 

Clear colorless to light yellow

PH

7.0-8.0 (100g/l, H2O, 20℃)

optical activity

[α]21/D +96.1°, c = 2 in chloroform

Water Solubility 

Soluble in water.

BRN 

80854

InChIKey

MEJYDZQQVZJMPP-ULAWRXDQSA-N

LogP

-1.62

CAS DataBase Reference

5306-85-4(CAS DataBase Reference)

Safety Information

Safety Statements 

23-24/25

WGK Germany 

3

HS Code 

29092000

MSDS

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

Isosorbide dimethyl ether Usage And Synthesis

Chemical Properties

clear colorless to light yellow liquid. very stable under neutral conditions, hygroscopic and miscible with most organic solvents.

Uses

dimethyl isosorbide is a carrier, solvent, and viscosity controller. Its particular skin-penetrating ability opens the possibility of enhancing active substance efficacy in optical products. Its physical characteristics and solubility properties are superior to those of propylene glycol, glycerin, or ethyl alcohol.

Uses

Isosorbide dimethyl ether (DMI), a sustainable solvent, is widely used in various cosmetic and pharmaceutical formulations.
General applications:
DMI can be used as an alternative green solvent for epoxidation of cyclooctene, Baylis–Hillman reaction of isomaltulose-derived aldehydes with α,β-unsaturated ketones and also in solid-phase synthesis.
It can be used as a coalescent for water-borne paints, where it acts as a co-solvent during the water loss phase and as a coalescing agent during the film formation.

Preparation

Isosorbide dimethyl ether is synthesized from isosorbide by methylation.
Isosorbide dimethyl ether is obtained from stock like D-sorbitol, which is mainly derived from the hydrogenation of D-glucose.
Isosorbide dimethyl has a low level of toxicity and is referred to as a green solvent due to its production from renewable/raw material.
The boiling point of this solvent is high.
lt is used as a substitute to dimethyl sulfoxide,and dimethylformamide-like solvents.

General Description

Dimethyl isosorbide (DMI) is a biobased greener solvent and thus aligns with "Use of Renewable Feedstocks" and "Safer Solvents and Auxiliaries".

Flammability and Explosibility

Non flammable

Synthesis

The general procedure for the synthesis of (3S,3aR,6R,6aR)-6-methoxyhexahydrofuro[3,2-b]furan-3-ol, (3R,3aR,6S,6aR)-6-methoxyhexahydrofuro[3,2-b]furan-3-ol, and isosorbide dimethylether using ethylene glycol dimethyl ether and isosorbide as raw materials is as follows: isosorbide, 1,2-dimethoxyethane ( ethylene glycol dimethyl ether) and heteropolyacid were sequentially added into a stainless steel high-pressure reactor and the reactor was sealed. The reaction mixture was magnetically stirred at 150°C for 5 hours. The molar ratio of 1,2-dimethoxyethane to isosorbide was 20:1, and the mass ratio of heteropolyacid to isosorbide was 0.2:1. After the reaction was completed, the reactor was cooled to room temperature. The reaction mixture was analyzed using gas chromatography, and the conversion and yield of the methylated product of isosorbide was calculated as molar percentage (mol%) by internal standard method.

References

[1] Patent: CN105646514, 2016, A. Location in patent: Paragraph 0041; 0042; 0043; 0044; 0045; 0046
[2] RSC Advances, 2015, vol. 5, # 31, p. 24139 - 24143

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