Synthesis method of cyclohexane dimethanol, catalyst and application thereof

A technology of cyclohexanedimethanol and a synthesis method, which is applied in the field of synthesis of cyclohexanedimethanol, can solve the problems of increased cost, lengthened process flow, reduced production efficiency, etc., and achieves improved production efficiency, simplified process flow, cost reduction and the like. low effect

Active Publication Date: 2018-05-04
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, the product of a typical hydroformylation reaction is generally an aldehyde, which usually needs to be further hydroge

Method used

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  • Synthesis method of cyclohexane dimethanol, catalyst and application thereof
  • Synthesis method of cyclohexane dimethanol, catalyst and application thereof
  • Synthesis method of cyclohexane dimethanol, catalyst and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] The three (2,4-di-tert-butylcyclohexyl) phosphine ligand used in the catalyst of this embodiment is prepared with reference to the following steps:

[0055] In the four-neck flask equipped with stirrer, reflux condenser, desiccator, constant pressure dropping funnel, thermometer and nitrogen protection device, add 20mL toluene; under nitrogen protection, add 2.7g metal sodium, start heating; when the temperature When the temperature rises to 90-100°C, the metallic sodium begins to melt, turn on the electric stirring, add 2.4mL of isoamyl alcohol, and stir to make the molten sodium disperse into fine off-white particles "sodium sand"; stop heating and cool down rapidly. When the temperature drops to about 75°C, add 2g of 2,4-di-tert-butylchlorobenzene dropwise under continuous stirring; when the temperature rises, keep the reaction temperature between 75-80°C, slowly add 10g of 2,4- Add di-tert-butylchlorobenzene for about 30 minutes, then keep it warm for 50 minutes; th...

Embodiment 2

[0065] Preparation of 3-cyclohexene-1-carbaldehyde:

[0066] Add 20g of cyclohexanedimethanol as a solvent to a stainless steel pressurized stirring tank with a volume of 50ml, heat up to melt and keep the temperature at 150°C, replace with nitrogen three times and keep the pressure at 4Mpa; add 4.8g of acrolein and 6.2g of 1,3-butane Diene. Under the condition of stirring, the temperature was maintained at 150° C. and the pressure was 4 MPa to react for 3 hours.

[0067] Sampling was carried out for GC (gas chromatography) analysis, and the yield of cyclohexene formaldehyde in terms of acrolein was >91%. Remove unreacted acrolein and butadiene by intermittent rectification under normal pressure, collect the top composition with a boiling point of 163-164°C, and obtain 3-cyclohexene- 1- Formaldehyde, spare.

[0068] Preparation of 1,4-cyclohexanedimethanol:

[0069] In the 50ml stainless steel reaction kettle, add 20g solvent (solvent is 1,4-cyclohexanedimethanol, 4-hydroxym...

Embodiment 3

[0071] The tricyclohexylphosphine ligand used in the catalyst of this example was provided by Jiangsu Sinoco Catalyst Co., Ltd., with a purity of 98%.

[0072] The synthetic method that present embodiment prepares cyclohexanedimethanol is as follows:

[0073] In a 50ml stainless steel reaction kettle, a mixture of 20g of cyclohexanol and methyl tert-butyl ether was added as a solvent, wherein the mass contents of cyclohexanol and methyl tert-butyl ether were 70%: 30%, respectively. Replace with nitrogen and synthesis gas three times in sequence, and then continue to flow synthesis gas. The composition of synthesis gas is CO and H with a volume ratio of 1:2. 2 , and maintain a pressure of 28Mpa. Add 0.03 g of precursor C 3 h 7 CCo 3 (CO) 9 , and 4 g of the aforementioned tricyclohexylphosphine as a catalyst, stirred at 110° C. for 30 min, during which the precursor was transformed into a hydrogenated polycarbonyl compound of cobalt. Take 50g of 3-cyclohexene-1-formaldehyd...

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PUM

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Abstract

The invention provides a synthesis method of cyclohexane dimethanol. The synthesis method comprises the following step: under the action of a catalyst, performing a hydroformylation reaction and a hydrogenation reaction on cyclohexene formaldehyde to obtain the cyclohexane dimethanol, wherein the catalyst comprises a cobalt compound and an organic tricyclohexylphosphine ligand; the cobalt compoundis preferably a hydrogenated polycarbonyl compound of cobalt. By adopting the synthesis method of the cyclohexane dimethanol, provided by the invention, the use of terephthalic acid and the like is avoided, the synthesis technology is simple, and the cost is low.

Description

technical field [0001] The invention relates to a method for synthesizing cyclohexanedimethanol. Background technique [0002] 1,4-Cyclohexanedimethanol (CHDM) is an aliphatic diol containing a six-membered ring in its molecular structure. Due to its cycloalkane structure, the polyester synthesized by it has higher crystallinity and temperature resistance than commonly used aliphatic diols. In recent years, the development of 1,4-cyclohexanedimethanol is very rapid, and it is the diol of polyester raw material that needs to be developed urgently in recent years. [0003] The traditional CHDM industrial preparation route is to use terephthalic acid based on petrochemical raw materials as a raw material, and prepare it through esterification and hydrogenation. The main raw material of this traditional route is terephthalic acid (PTA), which is a large-tonnage petrochemical product, prepared by oxidation of cyclohexane or cyclohexene, with many by-products, low yield, difficu...

Claims

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Application Information

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IPC IPC(8): C07C29/141C07C31/27C07C45/50C07C47/42B01J31/24
CPCB01J31/2404C07C29/141C07C45/50C07C31/27C07C47/42
Inventor 何岩乔小飞赵一鸣刘俊贤宋明炎张彦雨黎源
Owner WANHUA CHEM GRP CO LTD
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