Process for production of benzaldehyde co.mpound

A compound and technology of benzaldehyde, applied in the field of benzaldehyde compounds, can solve the problems of increasing environmental load, complicated operation and difficulty, and achieve the effect of reducing the amount of production and reducing the environmental load

Inactive Publication Date: 2009-08-12
UBE IND LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] However, in this method, since the generated salt must be temporarily separated and purified before use, the operation is complicated. In addition, in the Sommelet reaction, an aqueous acetic acid solution or an aqueous propionic acid solution containing ammonia is used as Solvent use, at this time, relative to 1 mole of salt formed by piperonyl chloride and hexamethylenetetramine, the amount of ammonia used is 0.5 to 4 moles, preferably 2 to 3.5 moles, so a large amount of new waste from ammonia, thereby causing a problem of increasing the environmental load, so this method is hardly an industrially superior method
[0017] In addition, in Cited Document 2, there is no description at all about the usage ratio of piperonyl chloride and hexamethylenetetramine used in the preparation of salt.

Method used

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  • Process for production of benzaldehyde co.mpound
  • Process for production of benzaldehyde co.mpound
  • Process for production of benzaldehyde co.mpound

Examples

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preparation example Construction

[0041] According to the production method of the benzaldehyde compound of the present invention, the benzyl compound having a leaving group used as a starting material is represented by the following general formula (I).

[0042]

[0043] In the above formula (I), L represents a group selected from a halogen atom, a hydroxysulfonyloxy group, an alkylsulfonyloxy group with or without a substituent, and an arylsulfonyloxy group with or without a substituent. Leaving group;

[0044] x, y, and z are the number of alkoxy substituents, each representing an integer of 0 or 1, and combined according to x+y+z becoming an integer of 1 to 3; R 1 ~R 3 Each independently represents a hydrogen atom, or a hydrocarbon group with or without a substituent, or, when x+y+z represents an integer of 2 or 3, an alkoxy substituent: OR 1 , OR 2 , OR 3 Any two of them can be bonded to each other to form an alkylenedioxy group, and form a ring structure together with two carbon atoms adjacent to ...

Embodiment 1

[0109] Example 1 (Synthesis of piperonal [heliotropin heliotropin]: molar ratio of hexamethylenetetramine to benzyl chloride compound: 0.25)

[0110] In a 200ml 3-necked flask, mix 17.06g (100mmol) of piperonyl chloride and 8.5ml of acetic acid with a purity of more than 96%, and add 3.50g (25mmol) of hexamethylenetetramine at a temperature of 20 to 27°C. , at a temperature of 115-125° C., stirring while refluxing to react, and prepare a mixed solution containing piperonyl chloride / hexamethylenetetramine salt (1). The mixed solution (1) was refluxed at a temperature of 115 to 125° C., and the mixed solution formed by 8.5 ml of water and 6.3 ml of hydrochloric acid aqueous solution with a concentration of 35% by mass was added dropwise thereto, to the mixed reaction solution obtained (pH: 0.80) at a temperature of 90 to 100° C. and stirred under reflux for 2 hours to synthesize piperonal. After the above reaction was completed, the obtained reaction solution was left to cool t...

Embodiment 2

[0115] Embodiment 2 (the synthesis of piperonal: the mol ratio of hexamethylenetetramine to benzyl chloride compound: 0.39)

[0116] In a 200ml 3-neck flask, mix 114.6g (1.10mol) of aqueous hydrochloric acid solution with a concentration of 35% by weight and 9.79g (0.300mol) of paraformaldehyde with a purity of 92% by weight, and cool the flask to an internal temperature of 8-9°C . A solution of 12.21 g (0.100 mol) of 1,2-methylenedioxybenzene in 20 ml of toluene was slowly added dropwise to the above liquid mixture, and stirred for 7 hours while maintaining the internal temperature at 8 to 9°C to allow reaction. After the reaction was completed, the obtained reaction solution was transferred to a separatory funnel, and the water layer was separated and removed. The organic layer obtained is transferred in the 3-neck flask of 200ml, after toluene is distilled off under reduced pressure, the concentrate obtained is carried out quantitative analysis with gas chromatography (int...

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Abstract

Disclosed is a process for the production of a benzaldehyde of the formula (II), which comprises the steps of: mixing a mixed solution (1) or (2) with water and an acid to prepare a mixed reaction solution, where the mixed solution (1) contains a salt produced by reacting a benzyl compound of the formula (I) having a leaving group (L) with hexamethylenetetramine in a solvent and a solvent and the mixed solution (2) contains the compound of the formula (I), a solvent for the compound and hexamethylenetetramine; and subjecting the mixed reaction solution to a reaction to produce the benzaldehyde compound, wherein the molar ratio of hexamethylenetetramine to the compound of the formula (I) is adjusted to a value not smaller than 0.25 and smaller than 1.00. (I) (II) wherein L represents a halogen atom or the like; x, y and z independently represent an integer of 0 or 1, provided that sum total of x, y and z ranges from 1 to 3; R<1> to R<3> independently represent a hydrogen atom or a hydrocarbon group which may have a substituent, or any two members of R1 to R3 may together form an alkylenedioxy group and form a cyclic structure together with two contiguous carbon atoms located on the benzene ring.

Description

technical field [0001] The present invention relates to a method for producing a benzaldehyde compound by performing a Sommelet reaction with, for example, a benzyl compound having a leaving group (such as a halogen atom, etc.) and hexamethylenetetramine. In more detail, the present invention relates to a method that can reduce the amount of hexamethylenetetramine when the benzaldehyde compound is prepared through the Sommelet reaction of a benzyl compound having a leaving group and hexamethylenetetramine, It is an industrially advantageous method that can produce the target compound in an industrially satisfactory yield and can reduce the amount of reaction waste generated. [0002] The benzaldehyde compound prepared by the method of the invention is a useful compound as a synthetic intermediate of medicine and pesticide and spice. Background technique [0003] The background art of the method of the present invention is described in the following documents. [0004] [Pat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/27C07C47/575C07D317/54
CPCC07C45/00C07D317/46
Inventor 土井隆志吉田佳弘藤津悟
Owner UBE IND LTD
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