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Method for producing carbonyl compounds

A technology for carbonyl compounds and ruthenium compounds, applied in the field of preparation of carbonyl compounds, can solve the problems of low catalyst activity and inability to obtain reactions, etc.

Inactive Publication Date: 2003-04-09
MITSUBISHI RAYON CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the activity of various catalysts in any of the above-mentioned methods is not very high, and hydrogen acceptors such as acetone must be added, and the reaction that is easy to realize industrially cannot be obtained.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Into a SUS autoclave with a capacity of 500 mL, 40.6 g of ruthenium tris(acetylacetonate) and 225.1 g of trioctylphosphine 6 times the mole were charged, hydrogen gas was introduced at a hydrogen pressure of 0.8 MPa, and the mixture was heated at 150° C. for 3 hours. Preparation of ruthenium complex catalyst.

[0045] Add 70.31 g of 1,4-butanediol and 30.1 g of γ-butyrolactone to a 300-mL four-neck flask equipped with a stirrer, a condenser, a temperature measuring instrument and a sampling port, and raise the temperature to 205°C. Then, 2.65 g of the aforementioned ruthenium complex catalyst (concentration of ruthenium metal: 1000 ppm by weight) was added, followed by heating and stirring at 203° C. for 5 hours. Measure the 1,4-butanediol conversion rate of the reaction solution, the selectivity of γ-butyrolactone, the amount of addition product of trioctylphosphine and γ-butyrolactone, and the weight ratio of the addition product in the reaction solution . The resul...

Embodiment 2

[0047] Except that the trioctylphosphine of 6 times of moles is changed into 4 times of moles to prepare the catalyst, and the ruthenium complex catalyst 2.65g used in the reaction is changed into 1.78g, other operations are the same as in Example 1, and the ruthenium complex catalyst is prepared Catalyst and dehydrogenation reaction. Measure the 1,4-butanediol conversion rate of the obtained reaction solution, the selectivity of γ-butyrolactone, the amount of addition product of trioctylphosphine and γ-butyrolactone, and the weight ratio of the addition product in the reaction solution . The results are shown in Table 1.

Embodiment 3

[0049] Except that the trioctylphosphine of 6 times of moles is changed into 2 times of moles to prepare the catalyst, and the ruthenium complex catalyst 2.65g used in the reaction is changed into 0.90g, other operations are the same as in Example 1, and the ruthenium complex catalyst is prepared Catalyst and dehydrogenation reaction. Measure the 1,4-butanediol conversion rate of the obtained reaction solution, the selectivity of γ-butyrolactone, the amount of addition product of trioctylphosphine and γ-butyrolactone, and the weight ratio of the addition product in the reaction solution . The results are shown in Table 1.

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Abstract

To provide a method for producing a carbonyl compound which does not need the addition of a hydrogen acceptor in the dehydrogenation of an alcohol by using an organic phosphine-ruthenium complex catalyst, reduces the formation of addition products and can attain the beneficial ligand cost in the dehydrogenation complex catalyst, additionally provide a method for producing a carbonyl compound, being capable of increasing the reaction rate as well as the reaction efficiency. When the carbonyl compound is produced by dehydrogenation of the alcohol in the presence of the organic phosphine-ruthenium complex catalyst, an organic phosphine and a ruthenium compound are mixed at an atom ratio of P / Ru of 2-8, then heated and the resultant product is used as the catalyst.

Description

technical field [0001] The invention relates to a method for preparing carbonyl compounds by dehydrogenating alcohols in the presence of organic phosphine-ruthenium complex catalysts. More specifically, it relates to a method for preparing lactone by dehydrogenating dihydric alcohol with two primary hydroxyl groups in the presence of an organic phosphine-ruthenium complex catalyst. Background technique [0002] Several methods are known for the dehydrogenation of alcohols to carbonyl compounds in the presence of organophosphine-ruthenium complex catalysts. For example, in the presence of a ruthenium-tetrahydride-tris(triphenylphosphine) complex catalyst, a method for preparing a lactone compound by dehydrogenating a dihydric alcohol (J.Orgmet.Chem., 1992, 429, 269-274) , the method (Bull.Chem.Soc.Jpn., 1988, 61.2291-2294) of methanol dehydrogenation in the presence of ruthenium-chloro-tetraacetoxy-ethyldiphenylphosphine complex catalyst, in acetic acid-phosphine The method...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/29C07B41/06
CPCB01J31/24C07B41/06C07C45/292C07C2531/24C07D307/32
Inventor 宇都宫贤高桥和成川上公德
Owner MITSUBISHI RAYON CO LTD