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Process for production of carbonyl compounds

一种羰基化合物、制造方法的技术，应用在碳基化合物制备、有机化合物的制备、氧化制备羰基化合物等方向，能够解决难以获得醛类、不能充分地满足工业上的需要、重金属废弃物处理麻烦等问题

Inactive Publication Date: 2006-04-19
SUMITOMO CHEM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the oxidation method using chromic acid, the disposal of heavy metal waste is troublesome, and it is difficult to obtain aldehydes due to oxidation to carboxylic acid.
In addition, in the method of oxidation using lead tetraacetate, lead tetraacetate has problems in storage stability, and the method of oxidation using periodic acid or periodate and the method of oxidation using pentavalent organic bismuth reagent There is a problem that expensive reagents must be used in the method, so these methods cannot fully meet the needs of industry

Method used

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  • Process for production of carbonyl compounds
  • Process for production of carbonyl compounds
  • Process for production of carbonyl compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] In a 100mL four-necked flask with a stirring device and a reflux cooling tube, drop into trans-3,3-dimethyl-2-(1,2-dihydroxy-2-methylpropyl)cyclopropanecarboxylic acid methyl ester (Content: 94.1% by weight) 0.2 g, 30 mL of acetonitrile, 0.1 g of triphenylbismuth, and 13.1 g of potassium carbonate. Methyl cyclopropanecarboxylate (content : 94.1% by weight) 10 ml of acetonitrile solution of 2 g, and 10 mL of acetonitrile solution in which 1.7 g of bromine was dissolved. Stir at this temperature for 30 minutes to allow it to react, then filter the insoluble components from the reaction solution, and wash with about 25 mL of acetonitrile to obtain a compound containing trans-3,3-dimethyl-2-formylcyclopropanecarboxylate The organic layer of methyl ester was 62.1 g.

[0056] Content of methyl trans-3,3-dimethyl-2-formylcyclopropanecarboxylate: 2.1% by weight.

[0057] Yield: 88%.

Embodiment 2

[0059] In a 100mL four-necked flask with a stirring device and a reflux cooling tube, drop into trans-3,3-dimethyl-2-(1,2-dihydroxy-2-methylpropyl)cyclopropanecarboxylic acid methyl ester (content: 94.1% by weight) 2.2 g, acetonitrile (3% by weight containing water) 30 mL, triphenylbismuth 0.05 g, succinimide 0.1 g, and potassium carbonate 5.3 g. 20 mL of an acetonitrile solution in which 1.9 g of bromine was dissolved was dropped therein at room temperature over 3.8 hours. Stir at this temperature for 30 minutes to allow it to react, then filter the insoluble components from the reaction solution, and wash with about 25 mL of acetonitrile to obtain a compound containing trans-3,3-dimethyl-2-formylcyclopropanecarboxylate 60.6 g of the organic layer of methyl ester.

[0060] Content of methyl trans-3,3-dimethyl-2-formylcyclopropanecarboxylate: 2.1% by weight.

[0061] Yield: 86%.

Embodiment 3

[0063]In a 100mL four-necked flask with a stirring device and a reflux cooling tube, drop into trans-3,3-dimethyl-2-(1,2-dihydroxy-2-methylpropyl)cyclopropanecarboxylic acid methyl ester (Content: 94% by weight) 0.22 g, acetonitrile (containing 3% by weight of water) 20 mL, succinimide group 0.1 g, triphenylbismuth 0.05 g, and potassium carbonate 5.3 g. Into it at an internal temperature of 40° C., 3 hours and 3.8 hours were added dropwise in parallel to dissolve trans-3,3-dimethyl-2-(1,2-dihydroxy-2-methylpropyl) ring 10 mL of an acetonitrile (3% by weight water) solution of 1.98 g of methyl propanecarboxylate (content: 94% by weight) and 20 mL of an acetonitrile (3% by weight water) solution in which 1.9 g of bromine was dissolved. Stir at this temperature for 30 minutes to allow it to react, then filter the insoluble components from the reaction solution, and wash with about 25 mL of acetonitrile to obtain a compound containing trans-3,3-dimethyl-2-formylcyclopropanecarboxy...

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Abstract

A process for the production of carbonyl compounds, characterized by reacting a diol represented by the general formula (1): (1) [wherein R<1>, R<2>, R<3> and R<4> are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or the like, with the provisos that all of R<1>, R<2>, R<3> and R<4> are not hydrogen simultaneously and that R<1> and R<2>, or R<3> and R<4>, together with the carbon atoms to which they are bonded, may form a ring] with bromine or an inorganic bromine compound in the presence of a bismuth(III) compound and a base to form carbonyl compounds represented by the general formulae (2) and (3): (2) [wherein R<1> and R<3> are each as defined above] (3) [wherein R<2> and R<4> are each as defined above].

Description

technical field [0001] The present invention relates to a method for producing carbonyl compounds. Background technique [0002] Carbonyl compounds represented by aldehydes are very important compounds as various chemical products, their synthetic intermediates, and the like. As a method for producing a carbonyl compound, a method of oxidatively cleaving a carbon-carbon bond to which a hydroxyl group is bonded in the vic.-diols by oxidizing the vic.-diols is known. Known methods such as oxidation using chromic acid (for example J.Am.Chem.Soc., 1962, 84 , 1252), the method of using lead tetraacetate to carry out oxidation (such as Chem.Ber., 1931, 64 , 260), the method of using periodate or periodate to carry out oxidation (such as Bull.Soc., Chim.Fr., 1928, 43 , 683), a method for oxidation using a pentavalent organic bismuth reagent (such as Tetrahedron, 1981, 37 , 73) etc. However, in the method of oxidation using chromic acid, the disposal of heavy metal waste is tro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/313C07C69/757C07D317/54C07C45/29C07C45/30C07C67/333
CPCC07C67/333C07D317/54C07C45/30C07C69/757C07C45/29C07C67/313
Inventor 高野尚之萩谷弘寿
Owner SUMITOMO CHEM CO LTD
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