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The preparation method of n,n'-bis(2,2,6,6-tetramethyl-4-piperidinyl)-1,3-benzenedicarboxamide

A technology of tetramethylpiperidinamine and phthalamide, which is applied in the field of preparation of multifunctional polyamide stabilizers, can solve the problems of three wastes pollution, etc., and achieve the effect of good product purity and high yield

Active Publication Date: 2020-11-10
JIANGSU XINZHOU CHEM SCI & TECH CO LTD
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  • Description
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Problems solved by technology

However, the acylation synthesis method will produce a large amount of waste acid, causing three waste pollution; the transesterification method will produce fatty alcohol and other by-products

Method used

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  • The preparation method of n,n'-bis(2,2,6,6-tetramethyl-4-piperidinyl)-1,3-benzenedicarboxamide
  • The preparation method of n,n'-bis(2,2,6,6-tetramethyl-4-piperidinyl)-1,3-benzenedicarboxamide
  • The preparation method of n,n'-bis(2,2,6,6-tetramethyl-4-piperidinyl)-1,3-benzenedicarboxamide

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[0020] The invention provides a preparation method of N,N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)-1,3-benzenedicarboxamide, comprising the following steps: making 2 ,2,6,6-Tetramethylpiperidinamine, isophthalic acid, water and heteropolyacid are mixed for dehydration reaction to obtain N,N'-bis(2,2,6,6-tetramethyl- 4-piperidinyl)-1,3-benzenedicarboxamide.

[0021] In the present invention, unless otherwise specified, the raw materials used are commercially available products well known in the art.

[0022] In the present invention, the heteropolyacid is preferably one or more of phosphotungstic acid, silicotungstic acid, molybdenum tungstic acid, phosphomolybdic acid and silicomomolybdic acid; There is no special requirement for the proportioning of heteropolyacids, and any proportioning is acceptable. In the present invention, the mass ratio of the isophthalic acid to the heteropolyacid is preferably 1:(0.01~0.2), more preferably 1:(0.05~0.17); the isophthalic acid and the ...

Embodiment 1

[0032] Add 83g of isophthalic acid, 312g of 2,2,6,6-tetramethylpiperidinamine, 16.6g of silicotungstic acid and 120g of distilled water into a 1L reaction vessel equipped with a thermometer, a reflux condenser and a stirrer at 100°C After heating and reacting for 2 hours, change the reflux condensation to a distillation device, heat up to 135°C and continue to react while distilling for 6 hours until no water is distilled out. Add 100g of distilled water when the reaction is stopped and cool to 70°C, slowly cool to room temperature, filter with suction, wash with 20g of water (directly reuse the mother liquor), and obtain N,N'-bis(2,2,6,6-tetramethyl -4-piperidinyl)-1,3-benzenedicarboxamide. The product was dried in a vacuum oven and weighed to obtain a product: 208.1 g, yield: 94.2%, and the purity measured by high performance liquid chromatography was 99.2%.

[0033] The product obtained in Example 1 is characterized by structure, and the results are as follows figure 1 an...

Embodiment 2

[0035]Add 83g of isophthalic acid, 156g of 2,2,6,6-tetramethylpiperidinamine and the mother liquor of Example 1 into a 1L reaction vessel equipped with a thermometer, a reflux condenser and a stirrer, and heat at 100°C for 2h Finally, change the reflux condensation to a distillation device, heat up to 135°C and continue to react while distilling for 6 hours until no water is distilled out. Add 100g of distilled water when the reaction is stopped and cool to 70°C, slowly cool to room temperature, filter with suction, wash with 20g of water (directly reuse the mother liquor), and obtain N,N'-bis(2,2,6,6-tetramethyl -4-piperidinyl)-1,3-benzenedicarboxamide. The product was dried in a vacuum oven and weighed to obtain the product: 213.2 g, yield: 96.5%, and the purity measured by high performance liquid chromatography was 99.1%.

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Abstract

The invention provides a preparation method of N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-1,3-phenyldimethylamide, and belongs to the technical field of preparation of a multifunctional polyamide stabilizer. The provided preparation method comprises the following steps that 2,2,6,6-tetramethyl-piperidyl-amino, isophthalic acid, water and heteropolyacid are mixed for a dehydration reaction to obtainthe N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-1,3-phenyldimethylamide. According to the method, the heteropolyacid is taken as a catalyst for directly performing the dehydration reaction to prepare the N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-1,3-phenyldimethylamide, which has the advantages of high yield, good product purity and the like; the reaction process does not generate any by-products other than water, which is environmentally friendly, and very suitable for industrial production. The catalyst can be directly reused without any treatment after the reaction is completed.

Description

technical field [0001] The invention relates to the technical field of preparation of multifunctional polyamide stabilizers, in particular to a kind of N,N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)-1,3-benzenedi Method for the preparation of formamide. Background technique [0002] N,N′-bis(2,2,6,6-tetramethyl-4-piperidinyl)-1,3-benzenedicarboxamide is an excellent light stabilizer widely used in polyethylene, Acrylic, polyvinyl chloride, polyurethane and other polymer materials. Since the late 1990s, the Swiss Clariant company has used N,N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)-1,3-phthalamide as a special After the stabilizer of the hindered amine structure of amide processing (the trade name is Nylostab SEED), it has become a research hotspot. Nylostab SEED has won the title of multifunctional polyamide stabilizer due to its excellent comprehensive performance in polyamide and other materials. [0003] As an important functional material, the current preparation method...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/58
CPCC07D211/58
Inventor 郑学军柏广明徐春清徐伟明吴爽
Owner JIANGSU XINZHOU CHEM SCI & TECH CO LTD
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