Method for preparing ultraviolet light absorber UVT-150

A technology of UVT-150 and absorbent, applied in the direction of organic chemistry, etc., can solve the problems of difficult esterification reaction, difficult to increase yield, waste water pollution, etc., and achieve the effect of simple production process, mild reaction conditions and simple preparation route

Active Publication Date: 2017-07-28
HUBEI NORMAL UNIV +1
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Problems solved by technology

[0008] The problem of the above-mentioned method one is that in the substitution reaction of melamine and p-chlorobenzoic acid, it is difficult to replace the chlorine substituent on the benzene ring with the amino group in melamine, so that the yield is difficult to improve; while intermediate 2,4,6- The yield of tris[(p-carboxyphenyl)amino]-1,3,5-triazine and isooctyl alcohol is not high, so the industrial cost of this process is relatively high
[0009] The problem of the above-mentioned method two is that the ultraviolet absorber UVT-150 product is prepared by directly using isooctyl aminobenzoate as a raw material and cyanuric chloride for substitution reaction, but since the raw material of isooctyl aminobenzoate is not produced domestically, the imported raw It is quite expensive, so al

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  • Method for preparing ultraviolet light absorber UVT-150
  • Method for preparing ultraviolet light absorber UVT-150
  • Method for preparing ultraviolet light absorber UVT-150

Examples

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Embodiment 1

[0031] ①Aromatic amination reaction: Add 950g of methyl p-aminobenzoate and 2000 mL of xylene to the reactor, raise the temperature to 60-150°C and stir to dissolve, and slowly drop the pre-dissolved in 1500 mL of xylene under this condition 380g of cyanuric chloride, the dropwise addition is completed, and the reaction is carried out at 120~125°C for 5-6h. The hydrogen chloride gas generated during the reaction is introduced into the lye absorption device. After the reaction is completed, the solvent is recovered by distillation, cooled and crystallized to obtain the intermediate methyl Triazinone 1036g, yield 98%, directly used for the next step transesterification reaction without refining.

[0032] ②Transesterification reaction: Add 2000 mL of toluene, 103.6 g of sodium methoxide and 1210 mL of isooctyl alcohol into the reactor, heat and stir to dissolve, and raise the temperature to 110~115 °C, slowly add 1500 mL of toluene containing 1036 g of methyl triazone Solution, a...

Embodiment 2

[0036] ①Aromatic amination reaction: Add 850g of methyl p-aminobenzoate and 1500 mL of benzene into the reactor, raise the temperature to 60-150°C and stir to dissolve, and slowly add dropwise the pre-dissolved in 800 mL of xylene under this condition 369g of cyanuric chloride, after the dropwise addition, keep warm at 120~125°C for 5-6h, the hydrogen chloride gas generated during the reaction is introduced into the lye absorption device, after the reaction is completed, the solvent is recovered by distillation, cooled and crystallized to obtain the intermediate methyl trichloride Azinonone 951g, yield 90%, directly used for the next step transesterification reaction without refining.

[0037]②Transesterification reaction: Add 1000 mL of toluene, 80 g of sulfuric acid and 800 mL of isooctyl alcohol into the reactor, heat and stir to dissolve, and raise the temperature to 110~115 °C, slowly add 1200 mL of toluene solution of 951 g of methyl triazone, dropwise After the addition...

Embodiment 3

[0039] ①Aromatic amination reaction: Add 800g of methyl p-aminobenzoate and 1800 mL of toluene to the reactor, raise the temperature to 60-150°C and stir to dissolve, and slowly add dropwise the pre-dissolved in 900 mL of xylene under this condition After the addition of 369g cyanuric chloride, the dropwise reaction was carried out at 120~125°C for 5-6 hours. The hydrogen chloride gas generated during the reaction was introduced into the lye absorption device. After the reaction was completed, the solvent was recovered by distillation, cooled and crystallized to obtain the intermediate methyl trichloride Azinonone 850g, yield 80%, directly used for the next step transesterification reaction without refining.

[0040] ②Transesterification reaction: Add 1000 mL of toluene, 70 g of toluenesulfonic acid and 800 mL of isooctyl alcohol into the reactor, heat and stir to dissolve, and raise the temperature to 110~115 °C, slowly add 850 g of methyl triazone in 1000 mL of toluene Solut...

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Abstract

The invention discloses a method for preparing an ultraviolet light absorber UVT-150. The method is composed of the following process steps: (1) carrying out an aryl amination reaction, namely adding methyl p-aminobenzoate and an organic solvent into a reactor, heating, slowly dripping cyanuric chloride, maintaining the temperature and reacting, distilling, and crystallizing so as to obtain an intermediate methyl triazone; and (2) carrying out an ester exchange reaction, namely adding methylbenzene, a catalyst and isooctyl alcohol into the reactor, heating, dripping a toluene solution of the methyl triazone, maintaining the temperature and reacting, distilling, and crystallizing thereby obtaining the product, namely the ultraviolet light absorber UVT-150. The method disclosed by the invention is simple in process route, readily available in raw materials, convenient to operate and high in yield, and the industrialized production is easily realized.

Description

technical field [0001] The invention relates to a synthesis method of an ultraviolet absorber, in particular to a preparation method of an ultraviolet absorber UVT-150. Background technique [0002] UVT-150 (also known as octyl triazone) is a triazine ultraviolet absorber, which has a special absorption function for the UVB (275-320 nm) band, and its chemical name is 4,4',4''-( Tris(2-ethylhexyl) 1,3,5-triazine-2,4,6-triimino)tribenzoate, high photostability and protection against UV-B-induced immunosuppression, water resistance Strong, has good affinity to the keratin protein of the skin. It has the advantages of high absorption rate and low dosage. Generally, only a very small dosage is needed in sunscreen care products to achieve high SPF value and excellent waterproof effect. [0003] Currently domestic and foreign reports about 4,4',4''-(1,3,5-triazine-2,4,6-triimino)tribenzoic acid tris(2-ethylhexyl)ester (UVT-150) The synthesis method mainly contains following two ...

Claims

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Application Information

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IPC IPC(8): C07D251/70
CPCC07D251/70
Inventor 汪敦佳李小林殷国栋范玲郑春阳徐文立刘建军
Owner HUBEI NORMAL UNIV
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