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Process for production of adipic acid from 1,6-hexanediol

A technology of adipic acid and hexanediol, applied in the field of novel heterogeneous catalysts, can solve problems such as examples of undisclosed yields

Pending Publication Date: 2020-07-28
ARCHER DANIELS MIDLAND CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In this patent no examples are disclosed of any yields achievable by the process

Method used

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  • Process for production of adipic acid from 1,6-hexanediol
  • Process for production of adipic acid from 1,6-hexanediol
  • Process for production of adipic acid from 1,6-hexanediol

Examples

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Embodiment 1

[0063] Example 1: Conversion of 1,6-hexanediol to adipic acid using Au, Au-Pd and Au-Pt catalysts

[0064] About 25 μl of HAuCl4 aqueous solution (comprising 28.6 wt% gold) was added to a suspension containing 600 mg of supports: silica Cariact Q-10 (Fuji Silysia); titanium dioxide ST 31119 (St. Gobain); and zirconium dioxide (Di Zirconia (XZO 1247 from St. Gobain, zirconium hydroxide from MEL Chemicals) was in deionized water (35ml) while shaking. The suspension was shaken for 5 min at room temperature. 1.92 ml of NH4OH (15.85M) aqueous solution was added to the above suspension, and the resulting suspension was shaken at room temperature for 2 hours. Then, the resulting suspension was centrifuged, and the colorless supernatant was decanted. After removing the residual liquid with filter paper, the orange-yellow solid was dried overnight in an oven at 60° C. under dry air.

[0065] The above support containing about 2 wt% Au was equally divided into thirds. Appropriate c...

Embodiment 2

[0069] Example 2: Conversion of 1,6-hexanediol to adipic acid using a Pt catalyst

[0070] The zirconia Z-2087 (Daiichi Kigenso Kagaku Kogyo) support was dried overnight in an oven at 60°C under a dry air purge. The samples were calcined at 650°C for 3 hours under an air atmosphere with a temperature ramp rate of 5°C / min. Appropriate concentration of Pt(NO 3 ) 2 The aqueous solution was added to 200 mg of the carrier and stirred to impregnate the carrier. The samples were dried overnight in an oven at 60 °C under a dry air purge. In forming gas (5% H 2 and 95%N 2 ) atmosphere, the sample was reduced at 350°C for 3 hours, and the temperature ramp rate was 5°C / min. The final catalyst consisted of approximately 3.9 wt% Pt.

[0071] The following assay protocol was employed to proceed to the oxidation of 1,6-hexanediol. The catalyst (approximately 10 mg) was weighed into a glass vial insert, then aqueous 1,6-hexanediol (200 μl, 0.1 M) was added. The glass vial inserts w...

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Abstract

Processes are disclosed for the conversion of 1,6-hexanediol to adipic acid employing a chemocatalytic reaction in which 1,6-hexanediol is reacted with oxygen in the presence of particular heterogeneous catalysts including at least one of platinum or gold. The metals are preferably provided on a support selected from the group of titania, stabilized titania, zirconia, stabilized zirconia, silica or mixtures thereof, most preferably zirconia stabilized with tungsten. The reaction with oxygen is carried out at a temperature from about 100 DEG C to about 300 DEG C and at a partial pressure of oxygen from about 50 psig to about 2000 psig.

Description

[0001] This application is a divisional application of a patent with the application number 201380030851.4, the filing date is June 11, 2013, and the invention title is "Method for Producing Adipic Acid from 1,6-Hexanediol". [0002] Cross References to Related Applications [0003] This application claims the benefit of US Provisional Application No. 61 / 658,364, filed June 11, 2012, the disclosure of which is incorporated herein by reference in its entirety. technical field [0004] The present disclosure generally relates to methods for the chemically catalytic conversion of 1,6-hexanediol to adipic acid. More specifically, the present disclosure relates to methods related to the use of heterogeneous catalysis in the presence of oxygen, as well as novel heterogeneous catalysts. Background technique [0005] In most cases, commodity, intermediate and specialty organic chemicals used around the world are ultimately derived from crude oil through processes involving chemical...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/235C07C55/14B01J23/42B01J23/652B01J35/10
CPCB01J23/44B01J21/066B01J23/6527B01J23/687C07C51/235B01J23/42B01J23/52B01J35/19B01J35/613B01J35/647C07C55/14C07C51/50B01J35/615B01J35/651
Inventor E·L·迪亚斯V·J·墨菲J·A·W·舒梅克
Owner ARCHER DANIELS MIDLAND CO
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