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Preparation method of 1,4-cyclohexanedimethanol

A technology of cyclohexane dimethanol and dimethyl toluate, which is applied in the field of preparation of chemical intermediates, can solve the problems of high hydrogenation pressure, achieve the effects of increasing yield, realizing catalytic hydrogenation reaction, and reducing pollution

Active Publication Date: 2015-02-04
SHANGYU SUNFIT CHEM
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  • Abstract
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Problems solved by technology

[0007] The Chinese patent application with publication number CN102795965A discloses a synthesis method of 1,4-cyclohexanedimethanol, using dimethyl terephthalate as a starting material, adopting a fixed-bed continuous reaction, and proceeding in two steps. Ru / Al 2 o 3 The modified catalyst is used for catalysis, the hydrogenation temperature is 140°C, the hydrogenation pressure is 4.0MPa, and the aromatic ring is hydrogenated; then the copper chromium modified catalyst is used for catalysis, the hydrogenation temperature is 180°C, and the pressure is 5.0MPa. The ester group is hydrogenated to obtain 1,4-cyclohexanedimethanol with a total yield of 94.3%, but there is a disadvantage that the hydrogenation pressure is too high

Method used

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  • Preparation method of 1,4-cyclohexanedimethanol
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  • Preparation method of 1,4-cyclohexanedimethanol

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Embodiment 1

[0026] In a 500mL autoclave, add 200g of water as a solvent, dimethyl terephthalate (19g, 0.1mol), RhCl 3 .3H 2 O (0.13g, 0.5mmol), the phosphine ligand represented by formula (II) (0.59g, 1mmol). After sealing the autoclave, extract the air in the autoclave, and replace it with nitrogen and hydrogen in sequence. Under the hydrogen pressure of 1.0MPa, stir and heat to 80°C to start the reaction. Keep the required hydrogen pressure until the reaction is completed. After six hours, cool and filter. The reaction solution was analyzed by gas chromatography, and the internal standard method was used to calculate the concentration of the reactant, the concentration of the intermediate product and the concentration of the product 1,4-cyclohexanedimethanol, and the reaction conversion rate was 93.5%, and the 1,4-cyclohexane The selectivity of dimethanol is 98.3%; among them, the mass ratio of trans 1,4-cyclohexanedimethanol to cis 1,4-cyclohexanedimethanol is 6.5:1, trans 1,4-cyclohe...

Embodiment 2

[0029] In a 500mL autoclave, sequentially add 200g of water as a solvent, dimethyl terephthalate (19g, 0.1mol), rhodium (II) acetate dimer (CAS: 15956-28-2, 0.22g, 0.5mmol ), the phosphine ligand represented by formula (II) (0.59 g, 1 mmol). After sealing the autoclave, extract the air in the autoclave, and replace it with nitrogen and hydrogen in sequence. Under the hydrogen pressure of 1.0MPa, stir and heat to 80°C to start the reaction. Keep the required hydrogen pressure until the reaction is completed. After six hours, cool and filter. The reaction solution was analyzed by gas chromatography, and the internal standard method was used to calculate the concentration of the reactant, the concentration of the intermediate product and the concentration of the product 1,4-cyclohexanedimethanol, and the reaction conversion rate was 90.1%, and the 1,4-cyclohexane The selectivity of dimethanol is 94.5%; among them, the mass ratio of trans 1,4-cyclohexanedimethanol to cis 1,4-cyclo...

Embodiment 3

[0031] In a 500mL autoclave, sequentially add 200g of n-butanol as solvent, dimethyl terephthalate (19g, 0.1mol), RhCl 3 .3H 2 O (0.13g, 0.5mmol), the phosphine ligand represented by formula (II) (0.59g, 1mmol). After sealing the autoclave, extract the air in the autoclave, and replace it with nitrogen and hydrogen in sequence. Under the hydrogen pressure of 1.0MPa, stir and heat to 80°C to start the reaction. Keep the required hydrogen pressure until the reaction is completed. After six hours, cool and filter. The reaction solution was analyzed by gas chromatography, and the internal standard method was used to calculate the concentration of the reactant, the concentration of the intermediate product and the concentration of the product 1,4-cyclohexanedimethanol, and the reaction conversion rate was 91.2%. 1,4-cyclohexane The selectivity of dimethanol is 93.8%, among which, the mass ratio of trans 1,4-cyclohexanedimethanol to cis 1,4-cyclohexanedimethanol is 6:1, trans 1,4-c...

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Abstract

The invention discloses a preparation method of 1,4-cyclohexanedimethanol, which comprises the following steps: carrying out hydrogenation reaction on p-dimethyl ditoluate in a solvent under the catalytic actions of a rhodium-containing catalyst and phosphine ligand; and after the reaction is completed, carrying out after-treatment to obtain the 1,4-cyclohexanedimethanol. The rhodium-containing catalyst is used as the hydrogenation catalyst, and the special phosphine ligand which can be coordinated with the rhodium-containing catalyst is added to enhance the activity of the rhodium-containing catalyst, so that the hydrogenation of the aromatic ring and the hydrogenation of the ester group can occur in one catalytic system, thereby simplifying the operation steps and enhancing the reaction yield.

Description

technical field [0001] The invention belongs to the preparation method of chemical intermediates, in particular to a preparation method of 1,4-cyclohexanedimethanol. Background technique [0002] 1,4-cyclohexanedimethanol, CAS number: 105-08-8, the structure is shown in formula (Ⅰ), is an important chemical intermediate, mainly used in the manufacture of polyester fiber, polyester electrical appliances , unsaturated polyester resins, polyester glazes, polyurethane foams, and for the production of lubricants and hydraulic fluids. [0003] [0004] The Chinese patent application whose publication number is CN101096332A discloses a method for producing 1,4-cyclohexanedimethanol from the hydrogenation of p-phenylenedimethanol, the catalyst used in the method is Al 2 o 3 As the carrier, metal Ru is used as the active component, the content of the active component metal Ru in the catalyst is 1-10wt%, the particle size of the catalyst is 80-200 mesh, the hydrogenation reaction...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C31/27C07C29/149
CPCB01J31/2404B01J2531/822C07C29/149C07C31/276
Inventor 梁旭华汪文婷王菊瑾黄生建
Owner SHANGYU SUNFIT CHEM
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