Undecane to pentadecane dicarboxylic acid di(2,2,6,6-tetramethylpiperidinyl)ester and use thereof

A technology of tetramethylpiperidinyl and dibasic acid dimethyl ester, which is applied in the field of hindered amine light stabilizer compounds, and can solve the problems of complex production process, limited application, high production cost, etc.

Inactive Publication Date: 2008-04-30
XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Before the 1980s, long-chain dibasic acids were mainly chemically synthesized. The productio

Method used

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  • Undecane to pentadecane dicarboxylic acid di(2,2,6,6-tetramethylpiperidinyl)ester and use thereof
  • Undecane to pentadecane dicarboxylic acid di(2,2,6,6-tetramethylpiperidinyl)ester and use thereof
  • Undecane to pentadecane dicarboxylic acid di(2,2,6,6-tetramethylpiperidinyl)ester and use thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0036] Preparation of dimethyl undecanedibasic acid:

[0037] In a three-necked flask equipped with a magnetic stirrer, a thermometer, and a reflux condenser, add 0.1 mol of undecanedibasic acid, 40 ml of methanol, and 0.3 ml of catalyst concentrated sulfuric acid. After reacting for 4 hours, add 2 times the amount of methanol to the reaction solution. Petroleum ether, separate the upper layer material containing long-chain dibasic acid dimethyl ester and petroleum ether and the lower layer material containing long-chain dibasic acid, and finally carry out reflux esterification reaction on the lower layer material, and combine the reaction liquid and the extracting liquid, Wash with 50ml of 2% NaOH solution, then wash with deionized water until neutral, and distill off the solvent under reduced pressure to obtain dimethyl undecanedibasic acid in the form of light yellow liquid;

[0038] The preparation of undecane dibasic acid di(2,2,6,6-tetramethylpiperidinyl) ester:

[0039...

Embodiment 2

[0041] Preparation of undecanedibasic acid diethyl ester:

[0042] In a three-necked flask equipped with a magnetic stirrer, a thermometer, and a reflux condenser, add 0.1 mol of undecanedibasic acid, 50 ml of ethanol, and 0.4 ml of catalyst concentrated sulfuric acid. After reacting for 5 hours, add 2 times the amount of ethanol to the reaction solution Petroleum ether, separate the upper layer material containing long-chain dibasic acid diethyl ester and petroleum ether and the lower layer material containing long-chain dibasic acid, and finally carry out the reflux esterification reaction of the lower layer material for 4 hours, and combine the reaction liquid and the extract , washed with 50ml of 2% NaOH solution, then washed with deionized water until neutral, distilled under reduced pressure, and evaporated the solvent to obtain diethyl undecanedibasic acid in the form of light yellow liquid.

[0043] The preparation of undecane dibasic acid di(2,2,6,6-tetramethylpiperid...

Embodiment 3

[0046] Preparation of Dimethyl Dodecanedibasic Acid

[0047] In a three-necked flask equipped with a magnetic stirrer, a thermometer, and a reflux condenser, add 0.1 mol of dodecanedibasic acid, 40 ml of methanol, and 0.3 ml of catalyst concentrated sulfuric acid. After reacting for 4.5 hours, add an amount equivalent to 4 Double the petroleum ether, separate the upper layer material containing long-chain dibasic acid dimethyl ester and petroleum ether and the lower layer material containing long-chain dibasic acid, and finally carry out the reflux esterification reaction on the lower layer material, and combine the reaction liquid and the extract , wash with 50ml of 2% NaOH solution, then wash with deionized water to neutrality, and distill off the solvent under reduced pressure to obtain light yellow liquid dimethyl dodecanedioic acid;

[0048] Preparation of dodecanedioic acid di(2,2,6,6-tetramethylpiperidinyl) ester:

[0049] A thermometer and a Soxhlet extractor equipped...

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Abstract

The invention relates to the synthesis and the usage of the novel hindered amine light stabilizer undecylenic to pentadecanedioic acid (2, 2, 6, 6-tetramethyl piperidino) diester. The invention utilizes undecylenic acid, dodecanedioic acid, tridecanedioic acid, tetradecanoic acid and pentadecanedioic acid produced through microorganism fermentation paraffinic oil as the raw material, the undecylenic to pentadecanedioic acid diesters are synthesized firstly, then the ester exchange reaction is performed to produce the finished product, secondly, the catalytic agent adopts sodium methoxide, sodium ethoxide or sodium amide which has higher activity, is easy to prepare and segregate, and is suitable for the use in industry, the related reaction condition is bland, the technology is simple, and the invention is easy to realize industrialization. The invention has very good light protection performance, and the addition into lubricating oil hydrogenised base oil can obviously improve the light stability quality. The invention can replace the prior Tinuvin770 sebacic acid (2, 2, 6, 6-tetramethyl piperidino) diester product. The structure formula of the invention is shown in the following (I), wherein, n is equal to 11 or 12 or 13 or 14 or 15.

Description

technical field [0001] The invention relates to a class of hindered amine light stabilizer compounds, which are di(2,2,6,6-tetramethylpiperidinyl) esters of undecyl or twelve or thirteen or fourteen or pentadecane dibasic acids , and the use of this type of hindered amine light stabilizer. Background technique [0002] Hindered amine light stabilizer (hindered amine light stabilizer, referred to as HALS) is a new light stabilizer of piperidine derivatives with steric hindrance effect, which was first developed in Japan in the 1970s. The hindered amine light stabilizer has the ability to capture free radicals and decompose peroxides, and the stabilization effect is 2 to 4 times higher than that of ultraviolet absorbers. Due to its unique and excellent light protection performance, it has been widely valued internationally, widely developed and applied, and has become the fastest-growing and fastest-growing light stabilizer in the world. The general structural formula is: ...

Claims

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Application Information

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IPC IPC(8): C07D211/44C09K15/30C10M133/40C08K5/3435C09D7/12C10N30/10
Inventor 赵文军魏菁晶关建王丽高林
Owner XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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