Catalyst used in ring-opening hydrogenation reaction of furan derivative

Abstract

The invention relates to a catalyst used in a ring-opening hydrogenation reaction of a furan derivative. The catalyst is applied to direct preparation of one-step ring-opening hydrogenation of 1,5-pentanediol and 1,2-pentanediol by taking furfural or furfuryl alcohol serving as a raw material under a mild condition. The catalyst can provide two active ingredients, namely the ring-opening active center of a transition metal oxide and the hydrogenation active center of Pt, Pd, Rh, Ru, Co or Ni, wherein the active center of the transition metal oxide is mainly used for adsorbing furfural or furfuryl alcohol and directly hydrogenating a furan ring for opening the furan ring; and the hydrogenation active center of a noble metal or Co, Ni and the like is mainly used for quickly hydrogenating an intermediate material and hydrogenating subsequent enol so as to obtain 1,5-pentanediol and 1,2-pentanediol. An environmentally-friendly, reproducible, low-cost, mild and effective method is provided for producing 1,5-pentanediol and 1,2-pentanediol. The high-performance ring-opening hydrogenation catalyst is also suitable for the ring-opening hydrogenation reaction of other furan derivatives.

Description

technical field [0001] The present patent relates to the preparation and application of a catalyst for the direct ring-opening hydrogenation reaction of furan derivatives under mild conditions. Background technique [0002] At present, the ring-opening hydrogenation of furan derivatives in industry is mainly used for the preparation of 1,5-pentanediol and 1,2-pentanediol. 1,5-Pentanediol is a widely used chemical product that can be used as a raw material for new polyesters, coatings, adhesives, plasticizers and sealants, as well as directly as cutting oils, detergents, wetting agents and special solvents. 1,2-Pentanediol is an intermediate for the production of pesticide propiconazole, and can also be directly used as a special solvent. Both pentanediols are currently expensive fine chemicals. Wherein, the synthesis method of 1,5-pentanediol mainly includes: (1) using tetrahydrofuran alcohol as raw material to directly hydrogenate ring-opening to prepare 1,5-pentanediol,...

AI Technical Summary

Problems solved by technology

Wherein the synthesis method of 1,5-pentanediol mainly includes: (1) using tetrahydrofuran alcohol as a raw material to directly hydrogenate ring-opening to prepare 1,5-pentanediol, the pressure range is 8MPa-42MPa, the temperature is 120°C-330°C, The method has high reaction temperature, large equipment investment, and high difficulty in operation; (2) cyclopentadiene is photooxidized to prepare epoxypentenol, and then hydrogenated at 70-100 ° C and about 6 MPa pressure to prepare 1,5 -pentanediol, but the preparation efficiency of cyclopentadiene photooxidation is low, so that the economy is not high; (3) firstly adopt glutaric acid as raw material to prepare 1,5-methyl glutarate, and then act on copper-zinc-aluminum catalyst 1,5-pentanediol is prepared by hydrogenation at 150-350°C and 3-5MPa, the conversion rate is greater than 95%, and the selectivity of 1,5-pentanediol is greater than 95% (Chinese patent CN1565728A), but the process flow It is relatively long, and the cost of glutaric acid is relatively high; (4) react with substituted vinyl ether and substituted acrolein to generate substituted 3,4-dihydropyran, then prepare glutaraldehyde through catalytic hydrolysis, and then Hydrogenation generates substituted pentanediol (Chinese patent CN1072168A), and the catalyst uses Raney nickel, modified Raney nickel, alumina loaded with platinum, palladium or nickel

This method has a long technical route and high cost

(5) Using Ru as the active component supported catalyst, using 1,5-glutaraldehyde as raw material, under relatively mild reaction conditions, 60-120 ° C, 2MPa-8MPa, hydrogenation to prepare 1,5-pentanedialdehyde Alcohol, high conversion and selectivity, but the cost of raw materials used in this technology is relatively high

The preparation method of 1,2-pentanediol mainly contains: (1) U.S. Patent US4479021 discloses to be raw material with n-pentene, formic acid and hydrogen peroxide, prepares 1,2-pentanediol, but can produce peroxygen during operation Acetic acid has certain safety risks, and Chinese patent CN1552684A has also utilized similar method; (2) U.S. Patent US4605795 discloses in benzene solvent, adopts pentene and perpropionic acid epoxidation to make 1-pentene oxide, and then Saponification to obtain 1,2-pentanediol process, but the solvent is more polluting to the environment

[0003] In summary, the current methods for preparing 1,5-pentanediol have harsh reaction conditions, high pressure and temperature, which lead to high initial investment costs of the device, difficult operation, and greatly increased reaction costs; and these methods use The cost of raw materials is relatively high, all of which are based on fossil energy, and today we are facing the difficulty of depletion of fossil energy

And 1,2-pentanediol's synthetic method technological process is long, and also faces above-mentioned similar problem

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