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Process for producing carbonyl compound

A technology of carbonyl compounds and compounds, applied in the field of production of carbonyl compounds, which can solve the problems of low reactivity and inability to obtain favorable effects

Inactive Publication Date: 2005-07-13
NAT INST OF ADVANCED IND SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the low reactivity and the need to use large amounts of hydrochloric acid, these methods cannot yet be considered as industrially advantageous (B.R. James and G.L. Rempel, J. Am. Chem. Soc., 91 , p. 863 (1969); J. Harpern, B.R. James and A.L.W. Kemp, J. Am. Chem. Soc., 88, p. 5142 (1966))
That is, it has been considered so far that the method of hydration of alkynes by adding a transition metal catalyst and an acid cannot obtain favorable effects.

Method used

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  • Process for producing carbonyl compound
  • Process for producing carbonyl compound
  • Process for producing carbonyl compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-4

[0088] 0.005g methyl (triphenylphosphine) gold (0.01mmol) is dissolved in 1ml and forms a solution in the solvent shown in table 1, adds the 1-octyne (1mmol) of 0.11g in this solution and by the concentrated sulfuric acid ( 0.5mmol) dissolved in 0.5ml of water to form an aqueous solution. Table 1 summarizes the yield of 2-octanone after stirring at 70 °C for 1 hour.

[0089] Table 1

[0090] Example

Embodiment 5

[0092] The reaction was performed in the same manner as in Example 1 except that 1-butyl-3-methylimidazolium hexafluorophosphate was used as a solvent. As a result, 2-octanone was obtained in a yield of 89%.

Embodiment 6

[0094] The reaction was performed in the same manner as in Example 5 except that 0.01 g of methyl(triphenylphosphine)gold (0.02 mmol) was used. As a result, 2-octanone was obtained in a yield of 96%.

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Abstract

The present invention relates to a method for hydrating alkynes, which enables the hydration of alkynes to proceed efficiently in terms of catalyst turnover, productivity and speed, and thereby industrially advantageously produces the corresponding carbonyl compounds. The present invention provides a method for producing a carbonyl compound comprising reacting an alkyne compound with water in an organic solvent in the presence of a gold catalyst, the gold catalyst being an organogold complex, and an acid.

Description

technical field [0001] The present invention relates to a process for the production of carbonyl compounds. Background technique [0002] Organic carbonyl compounds have important industrial value, such as raw materials for various solvents, ketone resins with excellent light resistance and chemical resistance, and radical polymerization initiators (ketone peroxides) used in the manufacture of synthetic resins wait. And, since these compounds are widely used as raw materials or reaction intermediates in the preparation of various compounds such as medicines and agricultural chemicals, carbonyl compounds are very useful compounds. [0003] So far, carbonyl compounds can be prepared by condensation reactions or oxidation reactions such as alcohols or hydrocarbons. Although known methods involve the hydration of alkynes (acetylene compounds) under acidic conditions, in practice no satisfactory results in terms of reactivity are obtained by this method unless electron-donating...

Claims

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Application Information

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IPC IPC(8): C07D333/22B01J31/24B01J31/26C07B61/00C07C45/26C07C47/02C07C47/46C07C49/04C07C49/12C07C49/16C07C49/17C07C49/573C07C49/76C07C49/78C07C49/782C07C49/84
CPCB01J31/2404B01J31/185B01J31/1865B01J31/1875B01J31/20B01J31/24B01J31/26B01J2231/32B01J2531/18C07C45/26
Inventor 水岛英一郎林辉幸佐藤一彦田中正人
Owner NAT INST OF ADVANCED IND SCI & TECH
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