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Method used for producing 1, 4-cyclohexanedimethanol

A technology of cyclohexanedimethanol and cyclohexanedicarboxylate, which is applied in the field of producing 1,4-cyclohexanedimethanol, can solve the problems of low solubility and high melting point of dimethyl terephthalate, and achieve The effect of low raw material residue, good product quality, and reduced hydrogen consumption

Inactive Publication Date: 2019-11-12
HUNAN CHANGLING PETROCHEM SCI & TECH DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to provide a method for producing 1,4-cyclohexanedimethanol in order to overcome the problems of high melting point and low solubility of the raw material dimethyl terephthalate existing in the prior art

Method used

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  • Method used for producing 1, 4-cyclohexanedimethanol
  • Method used for producing 1, 4-cyclohexanedimethanol
  • Method used for producing 1, 4-cyclohexanedimethanol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Primary hydrogenation unit: Dioctyl terephthalate and H 2 Pass through the fixed bed reactor together from bottom to top (the catalyst packed in it is Pd-Rh / Al 2 o 3 (0.3% by weight Pd, 0.3% by weight Rh), the catalyst in H 2 Atmosphere, reduction and activation at 150°C for 6 hours) for hydrogenation reaction, a micro-nanoporous membrane (the average diameter of nanopores is 20nm, and the average diameter of micropores is 800μm) is set in front of the fixed-bed reactor, and hydrogen passes through the micro-nanoporous membrane , highly dispersed or dissolved in dioctyl terephthalate. The hydrogenation reaction conditions are: temperature is 110°C, pressure is 3MPa, H 2 The molar ratio to dioctyl terephthalate is 10, and the weight space velocity of dioctyl terephthalate is 0.9h -1 . According to calculation, the conversion rate of dioctyl terephthalate at the outlet of the primary hydrogenation unit is 99.9%, and the selectivity of dioctyl 1,4-cyclohexanedicarboxy...

Embodiment 2

[0045] Primary hydrogenation unit: Dibutyl terephthalate and H 2 Pass through the fixed bed reactor together (the loaded catalyst is Ru / SiO 2 (2.3% by weight Ru), the catalyst in H 2 atmosphere, reduction and activation at 120°C for 10 hours) for hydrogenation reaction, the hydrogenation reaction conditions are: temperature is 60°C, pressure is 10MPa, H 2 The molar ratio to dibutyl terephthalate is 3.5, and the weight space velocity of dibutyl terephthalate is 1.3h -1 . It is calculated that the conversion rate of dibutyl terephthalate at the outlet of the primary hydrogenation unit is 99.8%, and the selectivity of dibutyl 1,4-cyclohexanedicarboxylate is 100%.

[0046] Secondary hydrogenation unit: the primary hydrogenation product containing dibutyl 1,4-cyclohexanedicarboxylate obtained from the primary hydrogenation unit and H 2 Pass through the fixed bed reactor together (the loaded catalyst is CuO-MnO 2 -ZrO 2 (60% by weight CuO, 35% by weight MnO 2 , 5% by weight Z...

Embodiment 3

[0049] Primary hydrogenation unit: Dioctyl terephthalate and H 2 Pass through fixed bed reactor together (the catalyst of packing is Rh-Pd / C (0.3% by weight Rh, 0.2% by weight of Pd), described catalyst is in H 2 atmosphere, reduction and activation at 180°C for 5 hours) for hydrogenation reaction, the reaction conditions are: temperature 160°C, pressure 0.1MPa, H 2 The molar ratio to dioctyl terephthalate is 100, and the weight space velocity of dioctyl terephthalate is 3h -1 . According to calculation, the conversion rate of dioctyl terephthalate at the outlet of the primary hydrogenation reactor is 99.6%, and the selectivity of dioctyl 1,4-cyclohexanedicarboxylate is 99.1%.

[0050] Secondary hydrogenation unit: the primary hydrogenation product containing dioctyl 1,4-cyclohexanedicarboxylate obtained from the primary hydrogenation unit and H 2 Pass through the fixed bed reactor together (the loaded catalyst is CuO-ZnO-Al 2 o 3 (42% by weight CuO, 38% by weight ZnO, 20...

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Abstract

The invention relates to a method used for producing 1, 4-cyclohexanedimethanol, and more specifically relates to a method used for producing 1, 4-cyclohexanedimethanol from a terephthalate dibasic ester. The method comprises following steps: 1, the terephthalate dibasic ester represented by formula I and hydrogen gas are subjected to hydrogenation reaction in the presence of a first catalyst to obtain 1, 4-cyclohexane diformic acid dibasic ester, wherein in formula I, R1 and R2 are different, and are independently selected from C4-C12 alkyl; 2, the 1, 4-cyclohexane diformic acid dibasic esterobtained in step 1 and hydrogen gas are subjected to hydrogenation reaction in the presence of a second catalyst to obtain a product flow containing 1, 4-cyclohexanedimethanol; and 3, the product flow containing 1, 4-cyclohexanedimethanol obtained in step 2 is subjected to separation to obtain 1, 4-cyclohexanedimethanol product. According to the method, reaction raw materials which are liquid atnormal temperature are adopted to solve a problem that solvent circulation energy consumption is large, full utilization of catalyst activity is realized, product separation technology is simple, andthe method is especially suitable for industrialized production.

Description

technical field [0001] The invention relates to a method for producing 1,4-cyclohexanedimethanol, in particular to a method for producing 1,4-cyclohexanedimethanol from terephthalic acid dibasic ester. Background technique [0002] 1,4-Cyclohexanedimethanol (abbreviated as CHDM) is a structurally symmetrical alicyclic diol containing two primary hydroxyl groups. It is an industrially important polyester (polyterephthalic acid 1,4-cyclo Hexanedimethanol ester PCT; copolymer of terephthalic acid, ethylene glycol and less than 50% 1,4-cyclohexanedimethanol PETG; terephthalic acid, ethylene glycol and more than 50% 1,4-cyclohexanedimethanol The raw material for the production of the copolymer PCTG of hexanedimethanol is an improved product of existing glycols such as ethylene glycol and neopentyl glycol. Saturated polyester synthesized from 1,4-cyclohexanedimethanol can be used as a high-performance plasticizer for glazes and coatings, and 1,4-cyclohexanedimethanol can also be ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/149C07C31/27
CPCC07C29/149C07C67/303C07C2601/14
Inventor 向明林汪永军敖博佘喜春
Owner HUNAN CHANGLING PETROCHEM SCI & TECH DEV CO LTD
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