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Method for producing aldehyde using bisphosphite and group 8-10 metal compound, and such bisphosphite

A bisphosphite and carbon double bond technology, applied in the field of aldehyde preparation, can solve the problems of reduced target aldehyde yield and inability to inhibit isomerization reaction, etc., to maintain catalyst activity, maintain productivity, hydrolysis resistance or The effect of high thermal stability

Active Publication Date: 2009-04-22
KURARAY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The present inventors applied the above-mentioned conventional hydroformylation reaction of rhodium compound and phosphorus compound to 1-methoxy-2,7- When using non-conjugated dienes such as octadiene, the following problems arise: the target product is not only an aldehyde formed by hydroformylation of the carbon-carbon double bond at the end of the molecule, but also a lot of carbon-carbon double bonds inside the molecule. Hydroformylation, resulting in a large amount of undesired by-products; or the inability to inhibit the isomerization reaction of the carbon-carbon double bond at the end of the molecule and inside the molecule, resulting in the problem that the yield of the target aldehyde cannot be avoided

Method used

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  • Method for producing aldehyde using bisphosphite and group 8-10 metal compound, and such bisphosphite
  • Method for producing aldehyde using bisphosphite and group 8-10 metal compound, and such bisphosphite
  • Method for producing aldehyde using bisphosphite and group 8-10 metal compound, and such bisphosphite

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preparation example Construction

[0038] The production method of bisphosphite (I) is not particularly limited, for example, there are the following methods.

[0039] R 1 When representing a hydrogen atom, the bisphenol represented by the formula (1-1) [hereinafter referred to as bisphenol (1- 1)] with general formula PY 1 3 (Y 1 Represent chlorine atom, bromine atom or iodine atom) shown in phosphorus trihalide compound reaction, thus prepare monophosphite shown in formula (3-1) [hereinafter referred to as monophosphite (3-1)] ( This method is hereinafter referred to as "monophosphite production method (a)").

[0040] [chemical formula 7]

[0041]

[0042] [chemical formula 8]

[0043]

[0044] On the other hand, R 1 When expressing an alkyl group, first, under an inert gas atmosphere such as nitrogen and argon, in the presence of a solvent and an alkaline substance used as needed, the bisphenol compound represented by the general formula (1-2) [hereinafter referred to as bisphenol (1-2)] react ...

Embodiment 1

[0128] [chemical formula 15]

[0129]

[0130] Add 82.12g (200mmol) 4,4',6,6'-tetra-tert-butyl-2,2'-bisphenol and 500mL toluene into a 1000mL three-necked flask with a thermometer and a dropping funnel, then add 59.2 g (390mmol) triethylamine, system nitrogen replacement. Next, 11.4 mL (130 mmol) of phosphorus trichloride was added dropwise over 30 minutes while maintaining the internal temperature at 20-30° C., and after the dropwise addition was completed, it was further stirred at room temperature for 12 hours. After the reaction is terminated, the by-product triethylamine hydrochloride is removed by filtration, and toluene and triethylamine (50° C. / 0.01 MPa) are decompressed from the resulting filtrate to obtain 95.0 g of crude monophosphite (3 -1). It was recrystallized and purified from a mixed solvent of 300 mL of acetonitrile and 150 mL of tetrahydrofuran to obtain 82.80 g of monophosphite (3-1) (based on phosphorus trichloride, the yield was 75%, and the purity w...

Embodiment 2

[0132] [chemical formula 16]

[0133]

[0134] Add 8.49g (10mmol) of monophosphite (3-1) and 50mL of toluene to a 100mL three-necked flask with a thermometer and a dropping funnel, and then add 1.52g (15mmol) of triethylamine to replace the system with nitrogen. Next, 2.6 mL (30 mmol) of phosphorus trichloride was added dropwise over 30 minutes while the internal temperature was kept at 20-30° C. After the dropwise addition, the temperature was raised to 70° C. and further stirred for 12 hours. After returning to room temperature, by-product triethylamine hydrochloride was removed by filtration, and phosphorus trichloride, toluene and triethylamine (50°C / 0.01MPa) were distilled off under reduced pressure from the obtained filtrate, thereby obtaining 10.5 g of crude Halophosphite (5-1).

[0135] [chemical formula 17]

[0136]

[0137] Then, add 10.5 g of the crude halogenated phosphorous acid ester (5-1), 100 mL of toluene and 3.03 g (30 mmol) of triethylamine obtained ...

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Abstract

Disclosed is a bisphosphite represented by the following general formula (I). Also disclosed is a method for producing an aldehyde, which is characterized in that a nonconjugated diene with 6-20 carbon atoms which has a carbon-carbon double bond at an end of the molecule is reacted with carbon monoxide and hydrogen in the presence of the bisphosphite and a group 8-10 metal compound. In the formula, A represents an optionally substituted alkylene group, an optionally substituted cycloalkylene group, an optionally substituted phenylene group or an optionally substituted naphthylene group; and R<1> represents a hydrogen atom or an alkyl group.

Description

technical field [0001] The present invention relates to a preparation method of aldehyde, which is characterized in that: in the presence of a bisphosphite with a specific structure and a metal compound of Group 8-10, a non-aldehydic compound having a carbon-carbon double bond at the end and having 6-20 carbon atoms Conjugated dienes react with carbon monoxide and hydrogen; the invention in turn relates to bisphosphites therein. The aldehydes obtained by the present invention can be used as pharmaceutical and pesticide intermediates or raw materials for various chemicals. Background technique [0002] The process of preparing aldehydes by reacting olefinic compounds with carbon monoxide and hydrogen in the presence of Group 8-10 metal compounds or Group 8-10 metal compounds and phosphorus compounds is called "hydroformylation reaction" or "carbonyl "Synthesis", as a method for preparing aldehydes, is known to have extremely high industrial application value. [0003] In th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6574C07C45/50C07C47/277B01J31/28C07B61/00
CPCB01J2531/822B01J31/185C07C45/50B01J2531/80C07F9/65746C07C45/49B01J2231/321C07C47/277C07F9/6574B01J31/28
Inventor 杉冈尚德安仁靏田拓大岩崎秀治
Owner KURARAY CO LTD
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