Method for preparing 1,10-decanediol through supercritical dimethyl sebacate hydrogenation

A technology of dimethyl sebacate and decanediol, which is applied in the field of supercritical hydrogenation of dimethyl sebacate to prepare 1,10-decanediol, which can solve the problems of high pressure and large amount of hydrogen recycling

Active Publication Date: 2016-04-20
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At a reaction temperature of 230~280°C and a hydrogenation pressure of 20~25MPa, the conversion rate is as high as 100%, and the selectivity is as high as 95%. The disadvantage of this process is that the pressure is high, so the application is limited.
[0009] In the process of preparing high-carbon alcohols by hydrogenation of esters above, the yield of high-carbon alcohols depends on the pressure and amount of hydrogen in the reactor. Therefore, hydrogen is usually in excess (generally the ratio of hydrogen to ester is above 150:1), The recycling of hydrogen is relatively large

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] (1), methyl alcohol and dimethyl sebacate are mixed homogeneously with mass ratio 2:3; (2), the raw material in hydrogen and step (1) is mixed with certain hydrogen-ester ratio and sent into the fixed-bed reactor Pre-mixer; (3), the uniformly mixed raw materials in step (2) are continuously fed into a 10ml 20~40 mesh Cu / ZnO / Al 2 o 3 Catalyst (Cu50%wt, ZnO40%wt, Al 2 o 3 10%wt) fixed-bed reactor for hydrogenation reaction under certain conditions. (see Table 1 for specific conditions); (4), the product enters the separator and separates to obtain 1,10-decanediol. The reaction results are shown in Table 1.

[0020] Table 1 embodiment 1 reaction conditions and reaction result

[0021] Reaction temperature / ℃ air speed / h -1 hydrogen ester ratio Reaction pressure / MPa X / % S / % 240 0.3 80:1 8.5 98.69 97.99 245 0.4 50:1 8 99.05 95.48 250 0.5 35:1 9 99.85 94.23

[0022] Note: X , the conversion rate of dimethyl sebacate; ...

Embodiment 2

[0026] (1), methyl alcohol and dimethyl sebacate are mixed homogeneously with 1:3 mass ratio; (2), hydrogen and the raw material in the step (1) are mixed with certain hydrogen-ester ratio and sent to the fixed-bed reactor Pre-mixer; (3), the uniformly mixed raw materials in step (2) are continuously fed into a 10ml 20~40 mesh Cu / ZnO / Al 2 o 3 Catalyst (Cu50%wt, ZnO30%wt, Al 2 o 3 20%wt) fixed-bed reactor, hydrogenation reaction is carried out under certain conditions. (see Table 2 for specific conditions); (4), the product enters the separator and separates to obtain 1,10-decanediol. The reaction results are shown in Table 2.

[0027] Table 2 embodiment 2 reaction conditions and reaction result

[0028] Reaction temperature / ℃ air speed / h -1 hydrogen ester ratio Reaction pressure / MPa X / % S / % 240 0.3 90:1 9 95.46 98.99 250 0.4 75:1 8.5 98.45 92.48 260 0.5 45:1 8 99.15 91.23

[0029] Note: X , the conversion rate of dime...

Embodiment 3

[0031] (1), methyl alcohol and dimethyl sebacate are mixed homogeneously with 1:1 mass ratio; (2), hydrogen is mixed with the raw material in step (1) and sent to fixed-bed reactor with certain hydrogen-ester ratio Pre-mixer; (3), the uniformly mixed raw materials in step (2) are continuously fed into a 10ml 20~40 mesh Cu / ZnO / Al 2 o 3 Catalyst (Cu40%wt, ZnO40%wt, Al 2 o 3 20%wt) fixed-bed reactor, hydrogenation reaction is carried out under certain conditions. (see Table 3 for the specific conditions); (4), the product enters the separator and separates to obtain 1,10-decanediol. The reaction results are shown in Table 3.

[0032] Table 3 embodiment 3 reaction conditions and reaction result

[0033] Reaction temperature / ℃ air speed / h -1 hydrogen ester ratio Reaction pressure / MPa X / % S / % 240 0.3 90:1 9 93.46 98.89 250 0.4 75:1 8.5 94.45 93.48 260 0.5 45:1 8 96.15 90.23

[0034] Note: X , the conversion rate of dimethyl...

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Abstract

The present invention discloses a method for preparing 1,10-decanediol through supercritical dimethyl sebacate hydrogenation. The method comprises that: (1) methanol is adopted as a supercritical fluid, the methanol and dimethyl sebacate are uniformly mixed, the obtained mixture is conveyed into a pre-mixer through a high-pressure injection pump, the pressure of hydrogen is increased through a hydrogen pressurization system to achieve a certain pressure, the pressurized hydrogen is conveyed to the pre-mixer and then is continuously conveyed into a fixed bed reactor loaded with a supported catalyst, and a hydrogenation reaction is performed at a reaction temature of 240-280 DEG C under a reaction pressure of 7-12 MPa according to a hydrogen to ester ratio of 30:1-150:1, wherein the reaction system is in the supercritical state of the methanol, and the used catalyst is a Cu / ZnO / Al2O3 catalyst; and (2) vapor-liquid separation is performed, the liquid phase product is collected, and the decanediol is rectified from the liquid phase product. According to the method of the present invention, the methanol is adopted as the supercritical fluid and does not have corrosion, the mass transfer resistance during the dimethyl sebacate reaction process can be eliminated, the hydrogen to ester ratio is low, and the conversion rate of the dimethyl sebacate and the selectivity of the 1,10-decanediol are high.

Description

technical field [0001] The invention belongs to the field of catalytic hydrogenation, and relates to a method for preparing 1,10-decanediol by hydrogenating supercritical dimethyl sebacate. Background technique [0002] 1,10-Decanediol is an emerging fine chemical raw material. It has two hydroxyl groups located at both ends of the carbon chain. It has high reactivity and can react with organic acids, isocyanates, anhydrides, etc. to produce different types of derivatives. . Due to its unique performance and the ability to produce a series of new fine chemical products, it is increasingly used in the fields of new polyurethanes, polyesters, plasticizers, pesticides, pharmaceuticals, and lubricant additives. It is mainly used to improve the mechanical strength of the product, and improve the performance of the product such as hydrolysis resistance, heat resistance and chemical corrosion resistance. [0003] At present, the 1,10-decanediol production process adopted by resea...

Claims

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Application Information

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IPC IPC(8): C07C31/20C07C29/149
CPCY02P20/52Y02P20/54
Inventor 黄冬袁俊秀王康杨智中徐冬梅
Owner CHINA PETROLEUM & CHEM CORP
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