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Method for synthesizing isohexitol ester

A technology for isohexitol ester and hexitol, applied in the field of preparing isohexitol ester, can solve the problems of complex operation process, high equipment requirements, long reaction time, etc., and achieves simplified reaction equipment, low equipment requirements, and shortened reaction time. Effect

Active Publication Date: 2021-05-04
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In summary, there are the following problems to be solved urgently in the process of synthesizing isosorbide dicarboxylate by adopting the above-mentioned "one-pot two-step method": the operation process is relatively complicated, the reaction time is long, the corrosiveness caused by strong acid and strong alkali requires high temperature, Operating conditions with high energy consumption such as high vacuum require high equipment

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  • Method for synthesizing isohexitol ester
  • Method for synthesizing isohexitol ester
  • Method for synthesizing isohexitol ester

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Effect test

Embodiment 1-5

[0044] Different aliphatic carboxylic acids shown in sorbitol, table 1, toluene and solid acid catalyst phosphotungstic heteropolyacid (H 3 PW 12 o 40 ) into the reactor, nitrogen replacement, closed reactor, 170 ℃ magnetic stirring reaction for 6 hours, wherein, the mol ratio of fatty carboxylic acid and sorbitol is 20:1, and the mol ratio of toluene and sorbitol is 10:1, The mass ratio of phosphotungstic heteropoly acid to sorbitol is 0.3:1. After the reaction was completed, the esterification product was quantitatively analyzed by gas chromatography internal standard method, expressed in mole percent (mol%).

[0045] The reaction results are shown in Table 1.

[0046] Table 1: Preparation of Isosorbide Carboxylate by One-Step Conversion of Sorbitol Catalyzed by Phosphotungstic Heteropoly Acid

[0047]

[0048] Typically, solid acid catalyzed sorbitol in aliphatic carboxylic acid one-step conversion of the resulting esterification products are 2-carboxylate isosorbide...

Embodiment 6

[0050] Put sorbitol, acetic acid, diethyl ketone and solid acid catalyst H-ZSM-5 molecular sieve into the reactor, replace with nitrogen, seal the reactor, and react with magnetic stirring at 190°C for 4 hours. Wherein, the molar ratio of acetic acid to sorbitol is 40:1, the molar ratio of diethyl ketone to sorbitol is 10:1, and the mass ratio of H-ZSM-5 molecular sieve to sorbitol is 0.2:1. Treat that reaction finishes, adopt gas chromatography internal standard method to carry out quantitative analysis to esterification product, represent with mole percentage (mol%), gained 2-acetate isosorbide yield is 13mol%, 5-acetate isosorbide yield 7mol%, the yield of isosorbide diacetate is 62mol%, and the total yield of isosorbide is 82mol%.

Embodiment 7

[0052] Put sorbitol, butyric acid, methyl isopropyl ketone and solid acid catalyst H-beta molecular sieve into the reactor, replace with nitrogen, seal the reactor, and react with magnetic stirring at 180°C for 10 hours. Wherein, the mol ratio of butyric acid and sorbitol is 4:1, the mol ratio of methyl isopropyl ketone and sorbitol is 4:1, and the mass ratio of H-beta molecular sieve and sorbitol is 0.01:1. Treat that reaction finishes, adopt gas chromatography internal standard method to carry out quantitative analysis to esterification product, represent with mole percentage (mol%), gained 2-butyric acid isosorbide yield is 11mol%, 5-butyric acid isosorbide The yield is 9 mol%, the yield of isosorbide dibutyrate is 65 mol%, and the total yield of isosorbide is 85 mol%.

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Abstract

The invention discloses a method for synthesizing isohexitol ester, which is characterized in that a material containing hexitol and an esterifying agent is contacted with a solid acid catalyst in the presence of an aprotic solvent, and the isohexitol ester is obtained through one-pot one-step reaction. The method is especially suitable for the reaction of directly synthesizing the isohexitol ester, especially isosorbide ester, from hexitol, especially sorbitol, the total yield of the obtained isohexitol ester is 80% or above, and the yield of the isosorbide dicarboxylate reaches 60% or above.

Description

technical field [0001] The invention relates to a method for preparing isohexitol ester, in particular to a method for directly using hexitol as a raw material to catalyze and prepare isohexitol carboxylate in one step. Background technique [0002] Hexitols (sorbitol, mannitol, and iditol) are an important class of bio-based platform molecules that can be directly converted from biomass such as fructose, glucose, and cellulose. However, unlike the low functionality of petroleum-based chemicals, the oxygen-rich structure of polyhydroxyls is the primary challenge for the high-value utilization of hexitols. For this reason, dehydration, as the deoxygenation technology with the lowest energy consumption, is preferred for the removal of hydroxyl functional groups of sugar alcohols in order to obtain high value-added derivatives. Isohexitols, including isosorbide, isomannide, and isoidide, as important secondary dehydration products of hexitols, have attracted much attention for...

Claims

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Application Information

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IPC IPC(8): C07D493/04
CPCC07D493/04
Inventor 车鹏华徐杰孙颖高进苗虹聂鑫
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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