阅读说明：本技术 一种光稳定剂中间体的制备方法 (Preparation method of light stabilizer intermediate ) 是由 祝君威 杨光 袁开锋 于 2019-07-29 设计创作，主要内容包括：本发明公开了一种光稳定剂中间体的制备方法,先以1-辛氧基-2,2,6,6-四甲基-4-哌啶醇和氯乙酰氯在催化剂作用下反应生成2-氯-乙酸(1-辛氧基-2,2,6,6-四甲基-4-氧基)酯,然后再和4-氨基-2,2,6,6-四甲基哌啶反应,合格后进行结晶离心,最终得到固体2-(2,2,6,6-四甲基-4-哌啶胺基)-乙酸(1-辛氧基-2,2,6,6-四甲基-4-氧基)酯；此光稳定剂中间体制备工艺流程简单,分离提纯过程简便,反应时间短,产品收率可达93%左右。(The invention discloses a preparation method of a light stabilizer intermediate, which comprises the steps of reacting 1-octyloxy-2, 2,6, 6-tetramethyl-4-piperidinol with chloroacetyl chloride under the action of a catalyst to generate 2-chloro-acetic acid (1-octyloxy-2, 2,6, 6-tetramethyl-4-oxy) ester, then reacting with 4-amino-2, 2,6, 6-tetramethyl piperidine, crystallizing and centrifuging after the product is qualified, and finally obtaining solid 2- (2,2,6, 6-tetramethyl-4-piperidinylamino) -acetic acid (1-octyloxy-2, 2,6, 6-tetramethyl-4-oxy) ester; the preparation process of the light stabilizer intermediate is simple, the separation and purification process is simple and convenient, the reaction time is short, and the product yield can reach about 93 percent.)

1. A light stabilizer intermediate characterized by the structural formula:

。

2. the light stabilizer intermediate as claimed in claim 1, wherein the synthetic route of the preparation method is as follows:

3. the intermediate of claim 2, wherein the preparation method comprises the following steps:

(1) dissolving chloroacetyl chloride in an organic solvent 1, adding a catalyst 1, and dropwise adding 1-octyloxy-2, 2,6, 6-tetramethyl-4-piperidinol;

(2) after the dropwise addition is finished, carrying out reaction to obtain solid 2-chloro-acetic acid (1-octyloxy-2, 2,6, 6-tetramethyl-4-oxy) ester;

(3) dissolving solid 2-chloro-acetic acid (1-octyloxy-2, 2,6, 6-tetramethyl-4-oxy) ester in an organic solvent 2, adding a catalyst 2, and dropwise adding 4-amino-2, 2,6, 6-tetramethylpiperidine for reaction to obtain a light stabilizer intermediate 2- (2,2,6, 6-tetramethyl-4-piperidinylamino) -acetic acid (1-octyloxy-2, 2,6, 6-tetramethyl-4-oxy) ester.

4. A light stabilizer intermediate as claimed in claim 3, wherein: the charging ratio of the 1-octyloxy-2, 2,6, 6-tetramethyl-4-piperidinol, the chloroacetyl chloride, the 4-amino-2, 2,6, 6-tetramethylpiperidine, the catalyst 1, the organic solvent 1, the catalyst 2 and the organic solvent 2 is as follows by mass: 1: 0.396-0.595:0.519-0.575:0.354-0.530:0.702-4.105:0.354-0.530:0.702-4.105.

5. A light stabilizer intermediate as claimed in claim 3, wherein: the organic solvent 1 is any one of dichloromethane, dichloroethane, trichloromethane and carbon tetrachloride; the organic solvent 2 is any one of dichloromethane, dichloroethane, chloroform and carbon tetrachloride.

6. A light stabilizer intermediate as claimed in claim 3, wherein: the catalyst 1 is any one of triethylamine, diethylamine, dimethylamine and pyridine.

7. A light stabilizer intermediate as claimed in claim 3, wherein: the catalyst 2 is any one of triethylamine, diethylamine, dimethylamine and pyridine.

8. A light stabilizer intermediate as claimed in claim 3, wherein: the dropping temperature in the step (1) is-20 to-10 ℃.

9. A light stabilizer intermediate as claimed in claim 3, wherein: the reaction temperature of the step (2) is 0-10 ℃, and the reaction time is 2-4 hours.

10. A light stabilizer intermediate as claimed in claim 3, wherein: the dripping temperature in the step (3) is 15-30 ℃, the reaction temperature is 30-50 ℃, and the reaction time is 2-6 hours.

Technical Field

The invention relates to a preparation method of a light stabilizer intermediate, belonging to the field of preparation of light stabilizer intermediates.

Background

The light stabilizer is an additive of high molecular products, which can shield or absorb the energy of ultraviolet rays, quench singlet oxygen and decompose hydroperoxide into inactive substances, etc., so that the possibility of photochemical reaction can be eliminated or slowed down, and the process of photoaging can be prevented or delayed under the radiation of light, thereby achieving the purpose of prolonging the service life of the high molecular products.

The hindered amine is an organic amine compound with steric hindrance, has a good inhibition effect on the photo-oxidative degradation reaction of high polymers and organic compounds, and is a light stabilizer with excellent performance.

Disclosure of Invention

The invention solves the technical problems of easy migration of hindered amine molecules, poor compatibility with industrial solvents, pesticide intolerance, toxicity and the like in the prior art, and provides a preparation method of a light stabilizer intermediate to solve the problems in the prior art.

In order to achieve the purpose, the technical scheme adopted by the invention is as follows:

a light stabilizer intermediate having the formula:

。

as an improvement of the invention, the synthetic process route of the preparation method is as follows:

as an improvement of the invention, the method comprises the following specific steps:

(1) dissolving chloroacetyl chloride in an organic solvent 1, adding a catalyst 1, and dropwise adding 1-octyloxy-2, 2,6, 6-tetramethyl-4-piperidinol;

(2) after the dropwise addition is finished, carrying out reaction to obtain solid 2-chloro-acetic acid (1-octyloxy-2, 2,6, 6-tetramethyl-4-oxy) ester;

(3) dissolving solid 2-chloro-acetic acid (1-octyloxy-2, 2,6, 6-tetramethyl-4-oxy) ester in an organic solvent 2, adding a catalyst 2, and dropwise adding 4-amino-2, 2,6, 6-tetramethylpiperidine for reaction to obtain a light stabilizer intermediate 2- (2,2,6, 6-tetramethyl-4-piperidinylamino) -acetic acid (1-octyloxy-2, 2,6, 6-tetramethyl-4-oxy) ester.

As an improvement of the present invention, the charging ratio of the 1-octyloxy-2, 2,6, 6-tetramethyl-4-piperidinol, chloroacetyl chloride, 4-amino-2, 2,6, 6-tetramethylpiperidine, catalyst 1, organic solvent 1, catalyst 2, and organic solvent 2 is, by mass: 1: 0.396-0.595:0.519-0.575:0.354-0.530:0.702-4.105:0.354-0.530:0.702-4.105.

As an improvement of the invention, the organic solvent 1 is any one of dichloromethane, dichloroethane, chloroform and carbon tetrachloride; the organic solvent 2 is any one of dichloromethane, dichloroethane, chloroform and carbon tetrachloride.

As an improvement of the invention, the catalyst 1 is any one of triethylamine, diethylamine, dimethylamine and pyridine.

In an improvement of the invention, the catalyst 2 is any one of triethylamine, diethylamine, dimethylamine and pyridine.

As an improvement of the invention, the dropping temperature in the step (1) is-20 to-10 ℃.

As an improvement of the invention, the reaction temperature of the step (2) is 0-10 ℃, and the reaction time is 2-4 hours.

As an improvement of the invention, the dripping temperature in the step (3) is 15-30 ℃, the reaction temperature is 30-50 ℃, and the reaction time is 2-6 hours.

Compared with the prior art, the invention has the following beneficial effects because the technology is adopted:

the light stabilizer intermediate 2- (2,2,6, 6-tetramethyl-4-piperidylamino) -acetic acid (1-octyloxy-2, 2,6, 6-tetramethyl-4-oxy) ester obtained by the invention is a direct raw material for preparing the light stabilizer 2- {4- [4, 6-bis (N-butyl-1, 2,2,6, 6-pentamethylpiperidinylamino) -1,3, 5-triazine-2-yl ]2,2,6, 6-tetramethyl-4-piperidylamino } -acetic acid (1-octyloxy-2, 2,6, 6-tetramethyl-4-oxy) ester, and the light stabilizer intermediate also has the application effect of the light stabilizer due to the long carbon chain of the octyloxy group, the compatibility with high polymer materials is improved, the downstream product of the light stabilizer 2- {4- [4, 6-bis (N-butyl-1, 2,2,6, 6-pentamethylpiperidinyl) -1,3, 5-triazine-2 yl ]2,2,6, 6-tetramethyl-4-piperidinylamino } -acetic acid (1-octyloxy-2, 2,6, 6-tetramethyl-4-oxy) ester has good compatibility with most industrial solvents and excellent high polymer compatibility, and can increase the oxidation resistance and light stability, slow down the aging decomposition and prolong the service life when added into plastics, rubber or coatings; in the processing and using process, no special smell is generated, the original color of the material is not influenced, and the high-temperature resistance is obvious.

Detailed Description

The present invention will be further illustrated with reference to the following specific embodiments.