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Chemical process to convert mucic acid to adipic acid

A technology of adipic acid and muconic acid, applied in the field of synthesizing saturated polycarboxylic acid esters, can solve the problems of low HMF conversion rate and insufficient reaction selectivity, etc.

Inactive Publication Date: 2016-08-24
AGENCY FOR SCI TECH & RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Stepwise hydrogenolysis of 5-hydroxymethylfurfural (HMF) can produce 1,6-hexanediol (a potential precursor of adipic acid) with high selectivity, although HMF conversion is low
Although the DODH reaction conditions are quite mild, the choice of substrates is limited to polyols and the reaction selectivity is not high enough

Method used

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  • Chemical process to convert mucic acid to adipic acid
  • Chemical process to convert mucic acid to adipic acid
  • Chemical process to convert mucic acid to adipic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Example 1: Materials

[0075]All starting materials were commercially available and used as received unless otherwise indicated. Muconic acid (98%), 3-pentanol (98%), TsOH (98%), 2-propanol (99.9%) were purchased from Merck; trans, trans-muconic acid (98%), 3- Octanol (99%) and 5% Pt / C were purchased from Aldrich. Methyltrioxyrhenium (MTO) (98%), Re 2 o 7 (99.99%) and Re 2 (CO) 10 was purchased from Strem Chemical, USA; 1-butanol (99.5%) was purchased from BDH Laboratory Supplies, England. Other reagents involved were from Sigma or Merck. Obtained using Brucker AV-400 (400MHz) spectrometer 1 H and 13 C NMR spectra. Chemical shifts are reported in ppm with reference to tetramethylsilane with solvent resonance as internal standard.

Embodiment 2

[0076] Example 2: General procedure for the synthesis of diethyl mucate 6

[0077] Mucic acid (5.0 g), H 2 SO 4 A mixture of (1ml) and ethanol (150.0ml) was refluxed (80°C) for 24h. The reaction mixture was cooled to room temperature and then stored at 3°C ​​for 1 day. The white precipitate was filtered off, washed with a small amount of cold ethanol, and dried under vacuum at 50 °C overnight. The mother liquor was evaporated to dryness to give a brown solid. The solid obtained from the mother liquor was recrystallized in 10 ml ethanol and recovered by the procedure as described above. The total amount of diethyl mucate was 5.1 g (90.0% yield).

Embodiment 3

[0078] Example 3: General Procedure for Deoxygenation Dehydration (DODH) of Mucic Acid

[0079] A mixture of mucic acid (1mmol, 210mg), methyl trioxyrhenium (MTO) (0.05mmol, 12mg), TsOH (0.05mmol, 12mg) and 3-pentanol (20.0ml) was placed in a flowing 50ml flask air or N 2 Under reflux (120°C). The mixture was initially a white suspension, then turned into a brown and clear solution after 4 h. After 12 h, the reaction mixture was evaporated to dryness. The solid was recrystallized to give the product. For kinetic studies, 1 ml of the reaction mixture was taken at specific time intervals and dried for NMR analysis; a known amount of mesitylene was added as an internal standard.

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Abstract

The present invention provides a method of synthesizing an ester of a saturated carboxylic acid from a saturated polyhydroxycarboxylic acid by performing a deoxydehydration reaction and a hydrogen transfer reaction.

Description

technical field [0001] The present invention generally relates to methods of synthesizing esters of saturated polycarboxylic acids. Background technique [0002] The production of bulk chemicals and fuels from renewable bio-based feedstocks has significant implications for the sustainability of human societies. As one of the most in-demand "fall-in" chemicals from biological sources, adipic acid is mainly used in the high-volume production of nylon-6,6 polyamides. 1 Global demand for adipic acid is growing at 3-3.5% per annum and is expected to reach 3.3 million metric tons in 2016. Currently, commercial adipic acid is mainly derived from petroleum-based cyclohexane, a process involving the oxidation of nitric acid. In addition to the non-renewable source of raw material cyclohexane used in this synthetic route, large amounts of nitrogen oxides (N 2 O, NO and NO 2 ) is also a major environmental issue. Therefore, it is highly desirable to develop sustainable and environ...

Claims

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Application Information

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IPC IPC(8): C07C67/00C07C51/09C07C55/14C07C57/16C07C69/44
CPCC07C67/08C07C67/303C07C51/09C07C51/377C07C69/44C07C69/602C07C55/14C07C57/16C07C51/36
Inventor 张玉根李秀凯
Owner AGENCY FOR SCI TECH & RES
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