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Catalyst for preparing ethylenically unsaturated aldehyde from ethylenically unsaturated alcohol, its preparation method and use

A catalyst and unsaturated technology, applied in chemical instruments and methods, physical/chemical process catalysts, carbon-based compound preparation, etc., can solve the problems of process safety, low selectivity, poor reactivity, etc., and achieve cheap and easy raw materials, The preparation method is simple and the activity is stable

Active Publication Date: 2020-06-16
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Copper catalysts have poor activity and low selectivity to the oxidation of unsaturated alcohols, and cannot meet the requirements of industrialization; although silver catalysts have good activity to the oxidation of unsaturated alcohols and have high yield and selectivity, they cannot be used under high temperature conditions. Under the environment, the silver nanoparticles are easy to aggregate and grow, which makes the silver catalyst easy to sinter, resulting in a short life of the catalyst.
At the same time, during the sintering process, the surface of the catalyst is easy to deposit carbon, which will cause the blockage of the catalyst pores, increase the internal pressure of the reactor, and cause process safety problems

Method used

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  • Catalyst for preparing ethylenically unsaturated aldehyde from ethylenically unsaturated alcohol, its preparation method and use
  • Catalyst for preparing ethylenically unsaturated aldehyde from ethylenically unsaturated alcohol, its preparation method and use
  • Catalyst for preparing ethylenically unsaturated aldehyde from ethylenically unsaturated alcohol, its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Preparation of Catalyst A: Add 5.25g TiO to 43.24g concentration of 25wt% ammonia under stirring condition 2 Make it form a suspension, add 3.99g of Ir to this suspension 5 (PO 4 ) 6 (OH) 2 , reacted at 60°C for 5h, left at room temperature and aged for 11h, washed the obtained precipitate by centrifugation, freeze-dried and then roasted at 400°C for 5h as a carrier; 0.17g of AgNO3 was dissolved in 0.2mL of water, 0.20g (NH4)2C2O4 was dissolved in 0.32mL of water, and the two solutions were placed in a 40°C water bath to react under stirring conditions. Wash the precipitate after reacting for 1 hour, add 0.34 mL of 5 mol / L ethylenediamine aqueous solution to the precipitate after washing for 2-3 times to obtain a silver-amine complex solution, add 3.08 gCu(NO 3 ) 2 , 0.002gRe(NO 3 ) 3 , 0.38gMo(NO 3 ) 4 Dissolved into a uniform solution, added the prepared carrier to the above solution, stirred for about 1 h, evaporated the solvent at 100°C, and calcined at 35...

Embodiment 2

[0052] Preparation of Catalyst B: Except using 3.06 g AgNO 3 , 2.16g Cu(NO 3 ) 2 , 0.01g Re(NO 3 ) 3 , 0.30gMo(NO 3 ) 4 , 3.68g TiO 2 , 4.06g Ir 5 (PO 4 ) 6 (OH) 2 . In the obtained catalyst B, silver accounts for 18.50wt%, copper accounts for 7wt%, rhenium accounts for 0.05wt%, molybdenum accounts for 0.80wt%, TiO 2 Accounted for 35%, Ir5(PO 4 ) 6 (OH) 2 Accounting for 38.65wt%.

[0053] Catalyst B Reactivity Test: Tested with reference to the method of Example 1, the reaction conversion rate was 72%, and the selectivity of 3-methyl-2-butene-1-aldehyde was 97%.

[0054] Catalyst B service life test: test with reference to the method of Example 1, the reaction activity did not decrease within 4000h, the conversion rate remained at 69-72%, the selectivity remained at 97-98%, and the reaction conversion rate began to decrease after 4200 hours. After 5000 hours, the conversion rate dropped below 50%.

Embodiment 3

[0056] Preparation of Catalyst C: Except using 4.13 g AgNO 3 , 0.15g Cu(NO 3 ) 2 , 0.09g Re(NO 3 ) 3 , 0.16gMo(NO 3 ) 4 , 4.20g TiO 2 , 3.53g Ir 5 (PO 4 ) 6 (OH) 2 . In the obtained catalyst C, silver accounts for 25wt%, copper accounts for 0.5wt%, rhenium accounts for 0.43wt%, molybdenum accounts for 0.43wt%, TiO 2 40%, Ir 5 (PO 4 ) 6 (OH) 2 Accounting for 33.65wt%.

[0057] Catalyst C Reactivity Test: Tested with reference to the method of Example 1, the reaction conversion rate was 75%, and the selectivity of 3-methyl-2-butene-1-aldehyde was 99%.

[0058] Catalyst C service life test: test with reference to the method of embodiment 1, the reaction activity does not see reduction in 4000h, the conversion rate is maintained at 73-75%, the selectivity is maintained at 97-99%, and the reaction conversion rate begins to decrease after 4100 hours. After 5000 hours, the conversion rate dropped below 50%.

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Abstract

The invention discloses a catalyst for preparing ethylenically unsaturated aldehyde from ethylenically unsaturated alcohol, its preparation method and application. The catalyst comprises 1-30wt% silver, 0.1-10wt% copper, 0.01-1wt% rhenium, 0.01-1wt% molybdenum, 30-50wt% TiO 2 , 20‑40wt% Ir 5 (PO 4 ) 6 (OH) 2 . The catalyst is particularly suitable for the oxidation of 3-methyl-2-butene-1-alcohol to prepare 3-methyl-2-butene-1-aldehyde. The catalyst of the invention has the characteristics of high reactivity, strong high-temperature sintering resistance, good stability, etc., and is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a catalyst for preparing ethylenically unsaturated aldehydes from ethylenically unsaturated alcohols, especially a catalyst for preparing 3-methyl-2-butene-1-aldehyde by oxidation of 3-methyl-2-butene-1 alcohol and its preparation method. Background technique [0002] 3-Methyl-2-butene-1-al, also known as isopentenal, is the raw material for the synthesis of isophytic alcohol; it can also be used as the starting material for the synthesis of citral, and then for the production of vitamin A, vitamin E, β- Carotene; it can also be used to synthesize spices such as damascenone and ironone. [0003] In the patent JPS60246340, it is reported that 3-methyl-2-buten-1-ol is oxidized by oxygen to obtain 3-methyl-2- Butene-1-al, the target product selectivity can reach 96%. This reaction needs to be carried out under relatively high temperature conditions, and the catalyst is easily sintered during the continuous operation of the reac...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J27/19C07C45/38C07C47/21
CPCB01J27/19C07C45/38C07C47/21
Inventor 张旭张涛吕英东郭劲资程晓波王延斌朱龙龙黎源华卫琦
Owner WANHUA CHEM GRP CO LTD
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