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Conversion of 1,2,5,6-hexanetetrol (HTO) to tetrahydrofuran dicarboxylic acid (THFDCA)

A technology of tetrahydrofuran dimethanol and hydroxyadipic acid, which is applied in metal/metal oxide/metal hydroxide catalysts, organic chemistry, chemical instruments and methods, etc., can solve the problem that the direct oxidation of primary alcohols has not been widely studied.

Active Publication Date: 2020-11-20
ARCHER DANIELS MIDLAND CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Direct oxidation of primary alcohols in the absence of functional groups under mild conditions with oxygen has not been extensively studied

Method used

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  • Conversion of 1,2,5,6-hexanetetrol (HTO) to tetrahydrofuran dicarboxylic acid (THFDCA)
  • Conversion of 1,2,5,6-hexanetetrol (HTO) to tetrahydrofuran dicarboxylic acid (THFDCA)
  • Conversion of 1,2,5,6-hexanetetrol (HTO) to tetrahydrofuran dicarboxylic acid (THFDCA)

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0045] Example 1. Tetrahydrofuran dimethanol (35 g), 100 ml of deionized water and 2 g of platinum-bismuth were added to a 3-necked flask equipped with a condenser. The reaction mixture was refluxed in an oil bath at 60°C with continuous stirring. An aqueous solution of NaOH (21 g in 40 ml) was added dropwise and after complete addition the mixture was heated to 150° C. overnight (ca. 16 hours). During the course of the reaction, samples were taken from the reaction mixture at regular intervals and then stored under ambient conditions prior to NMR analysis. Based on NMR data, the conversion of tetrahydrofuran dimethanol was 70%, with a yield of THFDCA of 50%.

example 2

[0046] Example 2. Tetrahydrofuran dimethanol (4 g: cis / trans), 30 ml deionized water, 2 g NaOH and 0.5 g Pt(Bi) / C were added to a 100 cc reactor. The reaction mixture was heated up to 150° C. under 6.9 MPa (1000 psi) of air for 3 hours. Based on NMR data, the conversion of tetrahydrofuran dimethanol was higher than 98%, with 87% yield of THFDCA and 13% of the monobasic acid, 2,5-anhydro-3,4-dideoxyhexanoic acid.

example 3

[0047] Example 3. Tetrahydrofuran dimethanol (35 g), 100 ml of deionized water and 2 g of platinum-bismuth were added to a 3-necked flask equipped with a condenser. The reaction mixture was refluxed in an oil bath at 60°C with continuous stirring. An aqueous solution of NaOH (21 g in 40 ml) was added dropwise, and after the addition was complete, the mixture was heated to 60° C. overnight (about 16 hours). During the course of the reaction, samples were taken from the reaction mixture at regular intervals and then stored under ambient conditions prior to NMR analysis. Based on NMR data, the conversion of tetrahydrofurandimethanol was 91%, with an 89% yield of 2,5-anhydro-3,4-dideoxyhexanoic acid, and no measurable yield of THFDCA. The reaction is shown below (and in figure 2 upper part of ):

[0048]

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Abstract

Disclosed herein are methods for synthesizing useful intermediates and / or products from 1,2,5,6-hexanetetrol (HTO), which itself can be derived from a sugar. In an aspect, a process is provided for production of THFDCA from 1,2,5,6-hexanetetrol (HTO). The process comprises the steps of (a) ring closing to form a ring compound and (b) oxidizing using a catalyst comprising platinum and bismuth to form an acid mixture. Step (a) may be performed before or after step (b).

Description

technical field [0001] The present invention relates to the conversion of 1,2,5,6-tetrahydroxyhexane (HTO) to tetrahydrofurandicarboxylic acid (THFDCA). Background technique [0002] Biomass contains carbohydrates or sugars that can be converted into value-added products. The production of biomass-derived products for non-food uses is a growing industry. Bio-based fuels are an example of an application of increasing interest. Another application of interest is the use of biomass as a feedstock for the synthesis of various chemical feedstocks from renewable hydrocarbon sources. [0003] In recent years, due to the abundance, renewable nature, and worldwide distribution of biomass, increasing efforts have been devoted to finding ways to utilize it as a feedstock for the production of organic chemicals. The conversion of sugars into value-added chemicals is of great importance when considering possible downstream chemical processing technologies. [0004] Heterogeneous cata...

Claims

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Application Information

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IPC IPC(8): C07D307/68
CPCC07D307/68C07D307/18B01J21/18B01J23/6447C07D307/24
Inventor 马驰骋
Owner ARCHER DANIELS MIDLAND CO