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Method for preparing diethylamino hydroxybenzoyl hexyl benzoate

A technology of diethylamino hydroxybenzoyl benzoic acid and hydroxybenzoyl, which is applied in the field of manufacturing diethylamino hydroxybenzoyl hexyl benzoate, can solve problems such as difficulty in application and mass production constraints, and achieve mass production Effects of production, high yield, and reduced number of purifications

Pending Publication Date: 2022-01-28
AS科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the crystallization method disclosed in said patent is a method of obtaining DHHB in a solid form by recooling to a temperature lower than the melting point after complete dissolution at a temperature higher than the melting point of DHHB (54° C.), and must go through a pulverization process.
This method is difficult to apply to general mass production equipment, so it will be restricted in mass production

Method used

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  • Method for preparing diethylamino hydroxybenzoyl hexyl benzoate
  • Method for preparing diethylamino hydroxybenzoyl hexyl benzoate
  • Method for preparing diethylamino hydroxybenzoyl hexyl benzoate

Examples

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Effect test

manufacture example 1

[0061] Production Example 1. Synthesis of 2-(4-N,N-diethylamino-2-hydroxybenzoyl)benzoic acid

[0062] After putting 3-diethylaminophenol (1.0 kg, 7.87 mol) and phthalic anhydride (1.17 kg, 7.87 mol) into the 3-neck flask, it was stirred with toluene (5.0 L). After raising the internal temperature of the reactor to 110-115° C. and stirring for 2 hours, it was cooled to 0-10° C. and the precipitated solid was filtered to obtain the title compound (1.7 kg, 89.9%).

[0063] 1 H NMR (CDCl 3 ): 12.52(s,1H),7.91(dd,1H),7.62(m,2H),7.33(dd,1H),6.74(d,1H),6.13(dd,1H),6.20(d,1H) ,1.16(m,6H)

manufacture example 2-11

[0064] Production Example 2-1. Synthesis of 1-chlorohexane

[0065] 1-Hexanol (1.2kg, 11.70mol) and dimethylformamide (DMF, 8.5g, 0.12mol) were stirred and SOCl was added dropwise while maintaining the internal temperature below 30°C 2 (2.1 kg, 17.6 mol). After completion of the dropwise addition, the internal temperature was raised to 80 to 90° C. and stirred for 5 hours. After confirming the completion of the reaction, cooling was performed, and 5 L of purified water was added to separate layers to obtain the title compound (1.3 kg, 94.2%).

[0066] 1 H NMR (CDCl 3 ): 3.49(t,2H), 1.72(m,2H), 1.28(m,2H), 1.27(m,4H), 0.88(m,3H).

manufacture example 2-21

[0067] Production Example 2-2. Synthesis of 1-bromohexane

[0068] 1-Hexanol (1.2 kg, 11.70 mol) and tetrahydrofuran (THF, 6.0 L) were stirred, and PBr was added dropwise while maintaining the internal temperature below 10 °C 3 (3.2 kg, 17.6 mol). After completion of the dropwise addition, the internal temperature was maintained at 10° C. or lower and stirred for 3 hours. After confirming the completion of the reaction, 5 L of purified water was thrown in and the layer was separated to obtain the title compound (1.8 kg, 91.4%).

[0069] 1 H NMR (CDCI 3 ): 3.40(t,2H), 1.85(m,2H), 1.43(m,2H), 1.31(m,4H), 0.90(m,3H).

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Abstract

The present invention relates to a method for preparing diethylamino hydroxybenzoyl hexyl benzoate and, specifically, to: a method for preparing diethylamino hydroxybenzoyl hexyl benzoate, which has a simple preparation process and can be commercially mass produced; and crystalline diethylamino hydroxybenzoyl hexyl benzoate particles prepared thereby. According to the present invention, crystalline diethylamino hydroxybenzoyl hexyl benzoate particles having an excellent ultraviolet blocking effect can be stably obtained in a high yield.

Description

technical field [0001] The present invention relates to a kind of manufacturing method of diethylamino hydroxybenzoyl hexyl benzoate, in particular to a kind of manufacturing method of diethylamino hydroxy benzoyl hexyl benzoate which is easy to manufacture and can realize commercial mass production , A method for producing crystalline particles of diethylaminohydroxybenzoylhexylbenzoate, and diethylaminohydroxybenzoylhexylbenzoate produced by the production method. Background technique [0002] All ultraviolet rays, including those contained in sunlight, are carcinogens. The International Agency for Research on Cancer, or IARC, classifies all types of UV rays as Group I carcinogens, ie substances known to induce cancer. [0003] In addition to being carcinogenic, UV rays can damage the skin, eyes and immune system and induce skin aging. In theory, aging can be delayed by 27 times when it is not exposed to ultraviolet light. In particular, a large amount of UV-B (320nm~28...

Claims

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Application Information

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IPC IPC(8): C07C213/06C07C219/34C07C213/10C07C221/00C07C225/22C07C229/52C07C227/14
CPCC07C227/18C07C229/52C07C213/06C07C219/34C07C213/10
Inventor 尹种培白弦玗崔银花
Owner AS科技有限公司
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