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Allyl acetate hydroformylation method

A technology of propylene acetate hydroformyl and hydroformyl, applied in the field of formylation reaction, can solve problems such as reduction, and achieve the effect of simple process

Inactive Publication Date: 2017-03-22
CNOOC TIANJIN CHEM RES & DESIGN INST +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The commonly used phosphine ligand in the hydroformylation reaction of allyl alcohol is triphenylphosphine, but this catalytic system generates 3-hydroxybutyraldehyde (4-HBA) in addition to the desired linear product Hydroxy-2-methylpropanal (HMPA) and other branched products, thereby reducing the yield of 1,4-butanediol

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0023] Add rhodium acetylacetonate dicarbonyl (0.08mmol) and bisphosphine-I ligand (0.48mmol) into a 300mL autoclave, replace the atmosphere in the autoclave with nitrogen three times, and then add 100g of toluene. Syngas (CO / H 2 The volume ratio is 1:1) to replace the atmosphere in the kettle three times, then raise the temperature to 70°C, add 17.6g of propylene acetate, and pressurize with synthesis gas to a pressure (gauge pressure) of 1.2MPa. Keep the pressure of the reactor at 1.2MPa, monitor the reaction of the gas, and when the gas does not react further, cool the reactor and release the gas. The reaction solution was analyzed by gas chromatography, and the results are shown in Table 1.

Embodiment 2

[0025] Add rhodium acetylacetonate dicarbonyl (0.06mmol) and bisphosphine-I ligand (0.60mmol) into a 300mL autoclave, replace the atmosphere in the autoclave with nitrogen three times, and then add 100g of n-heptane. Syngas (CO / H 2 The volume ratio is 1:1) to replace the atmosphere in the kettle three times, then raise the temperature to 75°C, add 13.6g of propylene acetate, and pressurize with synthesis gas to a pressure (gauge pressure) of 1.0MPa. Keep the pressure of the reactor at 1.0 MPa, monitor the reaction of the gas, and when the gas does not react further, cool the reactor and release the gas. The reaction solution was analyzed by gas chromatography, and the results are shown in Table 1.

Embodiment 3

[0027] Add rhodium acetylacetonate dicarbonyl (0.08mmol) and bisphosphine-I ligand (0.40mmol) into a 300mL autoclave, replace the atmosphere in the autoclave with nitrogen three times, and then add 100g of toluene. Syngas (CO / H 2 The volume ratio is 1:1) to replace the atmosphere in the kettle three times, then raise the temperature to 65°C, add 6.8g of propylene acetate, and pressurize with synthesis gas to a pressure (gauge pressure) of 1.5MPa. Keep the pressure of the reactor at 1.5MPa, monitor the reaction of the gas, and when the gas does not react further, cool the reactor and release the gas. The reaction solution was analyzed by gas chromatography, and the results are shown in Table 1.

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Abstract

The invention discloses an allyl acetate hydroformylation method. The method includes the step that with the existence of a solvent and a catalyst system, a hydroformylation reaction happens to allyl acetate, carbon monoxide and hydrogen, butyraldehyde acetate is generated. The catalyst system comprises a rhodium complex and 6,6'-(3,3',5,5'-4-tert-butylbiphenyl-2,2'-biradical)bis(oxy)bisdibenzo[d,f][1,3,2] dioxaphospholane heterocyclic heptylene . By the adoption of the method, the butyraldehyde acetate is prepared through the allyl acetate in a hydroformylation manner with higher efficiency, and the method has the beneficial effects that the process is simple, the straight-chain product selectivity is high, and catalyst ligands are easy to synthesized.

Description

[0001] Technical field: [0002] The invention relates to a formylation reaction, in particular to a method for producing butyraldehyde acetate by hydroformylation of propylene acetate. [0003] Background technique: [0004] 1,4-Butanediol (BDO for short) is an important organic and fine chemical raw material, which is widely used in the fields of medicine, chemical industry, textile, papermaking, automobile and daily chemical industry. BDO can produce polybutylene terephthalate (PBT), γ-butyrolactone (GBL) and polyurethane resin (PU Resin), coatings and plasticizers, etc., as well as solvents and brighteners in the electroplating industry Wait. [0005] American LYONDELL Chemical Company (formerly Arco Chemical Company) and Japanese Kuraray Company (KURARY) successfully developed an industrial method for synthesizing 1,4-butanediol from propylene oxide as raw material. In this process method, firstly, propylene oxide isomerized to produce allyl alcohol, and then the allyl a...

Claims

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Application Information

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IPC IPC(8): C07C67/38C07C69/14B01J31/24
CPCC07C67/38B01J31/2471B01J2231/321B01J2531/0238B01J2531/822C07C69/14
Inventor 李晨于海斌蒋凌云李继霞郝婷婷王鹏飞王本雷李俊刘艳
Owner CNOOC TIANJIN CHEM RES & DESIGN INST
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