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Synthesis method of 3, 5, 5-trimethylhexanal, catalytic system and application

A technology of trimethylhexanal and a synthesis method, which is applied in the field of homogeneous catalysis, can solve the problems of harsh reaction conditions, low activity of a catalytic system, instability, etc., and achieves the effects of stabilizing the catalytic system, improving the reaction activity, and being difficult to deactivate.

Pending Publication Date: 2022-02-18
上海簇睿低碳能源技术有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] In view of the above-mentioned shortcoming of the prior art, the purpose of the present invention is to provide a kind of synthetic method of 3,5,5-trimethylhexanal, for solving the problem of preparing 3,5,5-trimethylhexanal in the prior art The reaction conditions in the hexanal process are harsh, and the catalytic system is low in activity and unstable.

Method used

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  • Synthesis method of 3, 5, 5-trimethylhexanal, catalytic system and application
  • Synthesis method of 3, 5, 5-trimethylhexanal, catalytic system and application
  • Synthesis method of 3, 5, 5-trimethylhexanal, catalytic system and application

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[0027] The invention provides a kind of synthetic method of 3,5,5-trimethylhexanal, the method comprises the following steps:

[0028] In the presence of metal catalysts, triphenylphosphine oxide compound 1 (L1), and organic phosphine compound 2 (L2), diisobutene undergoes hydroformylation reaction with synthesis gas to obtain the 3,5,5-trimethylhexyl aldehyde.

[0029]

[0030] In the method of the present invention, the metal catalyst is a metal rhodium compound, including but not limited to rhodium trichloride, rhodium acetate, carbonylbis(triphenylphosphino)rhodium chloride, rhodium dicarbonyl acetylacetonate, 1,5-cyclooctyl Diene (acetylacetonate) rhodium, (acetylacetonyl) carbonyl (triphenylphosphine) rhodium, hydrogenated carbonyl tris (triphenylphosphine) rhodium, bis (triphenylphosphine) carbonyl rhodium chloride, tris (triphenylphosphine) rhodium One or more of rhodium chloride, tetrakis(triphenylphosphine)rhodium hydride, etc. Preferably, the metal catalyst is ...

Embodiment 1

[0101]

[0102] Weigh 2.58mg (0.01mmol) of rhodium dicarbonyl acetylacetonate catalyst, 307.47mg (0.5mmol) of three (2,4-di-tert-butylphenyl) phosphine oxide, 129.4mg (0.2mmol) of three (2, 4-di-tert-butylphenyl) phosphite, a certain amount of toluene solvent is placed in a 100ml autoclave, after using nitrogen replacement three times, the diisobutylene raw material (2 , the molar ratio of 4,4-trimethyl-1-pentene to 2,4,4-trimethyl-2-pentene is 7:3), and then replaced by a mixture of carbon monoxide and hydrogen (1:1) 5 times, then pour in the mixed gas of carbon monoxide and hydrogen (1:1) to 3MPa, the rhodium concentration in the reaction system is 100ppm, start stirring and then heat the reactor to 110°C, after 5 hours of constant temperature and pressure reaction, the reactor will naturally Cooled to room temperature, evacuated the remaining gas in the reactor under ventilated conditions, opened the reactor, added an internal standard to take a sample, analyzed the prod...

Embodiment 2

[0104] Using the same operating method as in Example 1 to react, compared with Example 1, three (2,4-di-tert-butylphenyl) phosphine oxide was replaced by 268.35mg (0.5mmol) of three (2-(tert-butyl base)-4-methoxyphenyl)phosphine oxide, the total conversion of diisobutene was 96%, and the yield of 3,5,5-trimethylhexanal was 91%.

[0105]

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Abstract

The invention belongs to the technical field of homogeneous catalysis, and relates to a synthesis method of 3, 5, 5-trimethylhexanal, a catalytic system and application. The method comprises the following steps: diisobutylene and synthesis gas are subjected to a hydroformylation reaction in the presence of a metal catalyst, a triphenylphosphine oxide compound 1 (L1) and an organic phosphine compound 2 (L2), and 3, 5, 5-trimethylhexanal is obtained. Other organic phosphine compounds are introduced into the metal catalyst / triphenylphosphine oxide system, so that the reaction activity and reaction effect of the triphenylphosphine oxide catalytic system are greatly improved, the 3, 5, 5-trimethylhexanal can be synthesized under relatively mild conditions, the substrate conversion rate is high, and the yield is high. The catalytic system provided by the invention is more stable, is not easy to inactivate, and is more suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of homogeneous catalysis, and relates to a synthesis method, a catalytic system and an application of 3,5,5-trimethylhexanal. Background technique [0002] C9 aldehyde is an important organic chemical intermediate. Chemical products such as alcohols and acids prepared from C9 aldehyde have many applications in the fields of plasticizers, detergents, surfactants, and refrigerants. For example, branched 3,5,5-trimethylhexanal is converted into 3,5,5-trimethylhexanal through further oxidative esterification and other reactions, which is widely used in high-grade lubricants, coatings and High-end chemicals in daily chemicals and other fields. [0003] Since Otto Roelen discovered the hydroformylation reaction of olefins in 1938, the hydroformylation catalytic system has experienced cobalt carbonyl high-pressure catalytic system, triphenylphosphine modified rhodium carbonyl low-pressure catalytic system, and wat...

Claims

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Application Information

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IPC IPC(8): C07C45/50B01J31/22C07C47/02
CPCC07C45/505B01J31/2234B01J31/1875B01J31/0271B01J31/0262B01J31/0259B01J2231/321B01J2531/822B01J35/19C07C47/02
Inventor 孙予罕王慧宋文越王栋梁焦玉佩范晨阳
Owner 上海簇睿低碳能源技术有限公司
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