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Method for preparing decanediol dicarboxylate and derivative thereof

A technology of decanediol dicarboxylate and carboxylic acid, which is applied in the field of chemical preparation and can solve problems such as limited sources

Active Publication Date: 2020-04-17
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The traditional synthesis method of 1,10-decanediol generally uses diethyl sebacate as a raw material, and diethyl sebacate is derived from palm vegetable oil, and the source is limited

Method used

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  • Method for preparing decanediol dicarboxylate and derivative thereof
  • Method for preparing decanediol dicarboxylate and derivative thereof
  • Method for preparing decanediol dicarboxylate and derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] NHC catalyst cycle:

[0063] Under an inert atmosphere, sequentially add 0.5mmoLNHC catalyst into a 100mL Shrek tube And 2mmoL triethylamine, then add 0.1moL furfural, react at 80°C for 3h, after the reaction, the product is dissolved in acetic acid and filtered. The obtained filter residue was successively washed three times with methanol and three times with acetone. After drying, put it into a Shrek bottle, then add 2mmoL triethylamine and 0.1moL furfural, operate according to the above process, repeat 10 times, and measure the yield of furoin by HPLC as follows: figure 1 shown.

Embodiment 2

[0065] Under an inert atmosphere, add 0.005mmoL NHC catalyst to the Shrek tube sequentially Mix 0.02mmoL triethylamine, then add 1.0mmoL furfural, and react at 80°C for 3h to obtain furoin. Dissolve 0.5moL of the obtained furoin with acetic acid, filter to remove the NHC catalyst, transfer the filtrate to a high-pressure reactor, and then add 0.05mmoL Sc(OTf) 3 and 0.04mmoL Pd / C, filled with 4MPa H 2 , reacted at 185°C for 60min. After the mixed product is filtered and vacuum distilled, decanediol diacetate and n-decyl acetate can be obtained respectively.

[0066]

[0067] The H NMR spectrum of decanediol diacetate figure 2 Shown: 1 H NMR (400MHz, CDCl 3 ): δ=4.00(t, 6.00Hz, 4H), 2.05(s, 6H), 1.68-1.63(m, 6H), 1.40-1.25(m, 12H).

[0068] The carbon NMR spectrum of decanediol diacetate is as image 3 Shown: 13 C NMR (101MHz, CDCl 3 ): δ = 171.27, 64.63, 29.40, 29.20, 28.58, 25.88, 21.02.

[0069] The H NMR spectrum of n-decyl acetate is as Figure 4 Shown: 1 H...

Embodiment 3

[0074] Take 5.0g furfural and 100mL THF into a 500mL four-neck round bottom flask, stir at -10°C for 10min, then within 30min, add 11.83g TiCl 4 Add dropwise to the flask. After another 30 min, 8.1 g of Zn powder was divided into small portions and added to the flask within 30 min. After the addition was complete, the mixture was kept stirring at -10 °C for 1 h, then warmed to room temperature and refluxed overnight. After the reaction was completed, the reaction was quenched with ice water and filtered. The resulting solid was dissolved in dichloromethane and filtered. The obtained filtrate was extracted 2-3 times with dichloromethane, and the dichloromethane was removed by rotary evaporation. The resulting crude product was purified by silica gel chromatography to give a white solid, namely 1,2-difurylethene. Take 0.5mmoL of the 1,2-difurylethylene obtained in the above steps and place it in the autoclave, then add 0.05mmoL of Sc(OTf) 3 , 0.04mmoL Pd / C and 10mL acetic a...

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Abstract

The invention discloses a method for preparing decanediol dicarboxylate and a derivative thereof. The furfural is used as a raw material and can be obtained by hydrolyzing hemicellulose, and the furfural is efficiently converted into decanediol dicarboxylic ester, carboxylic acid n-decyl ester and corresponding alcohol through two steps of condensation and hydrogenolysis. The method is characterized in that a compound shown as a formula (I) is used as a raw material, and under the dual action of trifluoromethanesulfonate and a hydrogenation catalyst, decanediol dicarboxylate and carboxylic acid n-decyl ester are obtained through selective hydrodeoxygenation in an acid solvent. A saponification reaction is carried out on the product to obtain 1, 10-decanediol and n-decanol. The method has the advantages of cheap and accessible raw materials, high product yield, high product purity, low environmental pollution and simple process route, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of chemicals, in particular to a preparation method of decanediol dicarboxylate and n-decyl carboxylate. Background technique [0002] With the increasing depletion of non-renewable resources and resource shortages caused by population growth, the scientific community and industrial entities are increasingly paying attention to the research needs of sustainable energy and renewable chemicals. Biomass is rich in carbon resources and comes from a wide range of sources. Large-scale use of biomass resources can also promote the development of agriculture. Furfural is a small molecule of biomass platform, which can be obtained by hydrolysis of cellulose, and the global annual production can reach 280 kilotons. [0003] 1,10-Decanediol is a white needle-like crystal, easily soluble in alcohol and hot ether, and can be used as an organic solvent. At the same time, 1,10-decanediol is also an important fine chemic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/00C07C69/16C07C69/14C07D307/46
CPCC07C67/00C07D307/46C07C69/16C07C69/14
Inventor 邓晋蒋芹竹傅尧
Owner UNIV OF SCI & TECH OF CHINA
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