Synthesis of 2,5-furandimethanol dimethyl ether_industrial additives

Background and overview^[1]

2,5-furandimethanol dimethyl ether is an excellent class of bio-based chemicals. The molecule contains the structures of both ether and furan or tetrahydrofuran, so it has good solubility properties similar to ether, furan or tetrahydrofuran. It is not only soluble in water, but also compatible with many polymers and organic substances, and can be used as an organic solvent; it can also be used in the preparation of other heterocyclic fine chemical products, such as pesticides, pharmaceuticals and other industries.

Preparation^[1]

At present, the synthesis of such furan ether compounds is usually obtained by dehydration and condensation in the presence of acidic catalysts. The main problems are low selectivity, most of them can only synthesize single-sided furan ether compounds, and the yield is not ideal. This is mainly because furan compounds are unstable under certain acidic conditions and are prone to ring-opening reactions. For example, in the presence of conventional acid catalysts—protonic acid or Lewis acid catalyst, 2,5-furandimethanol dimethyl is prepared from furfuryl alcohol. base ether method, the selectivity of this method is not high, and the yield is not ideal, with a maximum of only 56%. Therefore, how to control the acidity of the catalyst so that it can both catalyze the etherification reaction and protect the furan ring to the maximum extent has become the key to improving the selectivity and yield of furan ether compounds.

CN201810300026.6 provides a preparation method of 2,5-furandimethanol dimethyl ether: dissolve 1 gram of 2,5-furandimethanol in 80 ml of methanol and pour it into a 250 ml two-neck round-bottomed flask , add 1 gram of hierarchical ZSM-5, stir the reaction in an oil bath at 40°C, react for 12 hours, wait until the temperature drops to room temperature, filter to remove the catalyst, and the methanol in the reaction mixture is removed by vacuum distillation at 35°C to obtain Light yellow 2,5-furandimethanol dimethyl ether was analyzed by high performance liquid chromatography. The conversion rate of 2,5-furandimethanol and the selectivity of 2,5-furandimethanol dimethyl ether were 100% and 92.36 respectively. %, the yield is 92.36%.

This method has the following beneficial effects:

1) The reaction is simple and has few by-products. The yield of 2,5-furandimethanol dialkyl ether and 2,5-tetrahydrofurandimethanol dialkyl ether can reach up to 99.8%;

2) The catalyst is a solid catalyst, which has low corrosion to equipment, can be removed by filtration, and can be reused, reducing catalyst costs;

3) The alkyl alcohol and water in the reaction solution can be removed by distillation under reduced pressure, and high-purity 2,5-furandimethanol dialkyl ether and 2,5-tetrahydrofurandimethanol dialkyl ether can be easily obtained. Moreover, alkyl alcohols can be recycled and reused, further reducing production costs and making them suitable for industrial production.

Main reference materials

[1] CN201810300026.6 Preparation method of furan ether compounds