Method for preparing bis(1-alkoxy-2,2,6,6-tetramethyl piperidine-4-yl) sebate

A technology of tetramethylpiperidine and tetramethylpiperidinol, applied in bis(1-alkoxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate In the field of preparation, it can solve the problems of by-products that are difficult to handle, difficult to handle, and pollute the environment

Pending Publication Date: 2019-05-03
山东兄弟科技股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But this reaction has the following problems: the esterification reaction produces a large amount of by-product-hydrochloric acid, in order to make the reaction normally, need to consume a large amount of acid-binding agent-triethylamine, the by-product of formation is difficult to handle, pollutes environment; It is prepared from sebacic acid and thionyl chloride as raw materials. During the preparation process, a large amount of hydrogen chloride and sulfur dioxide are produced, which is difficult to handle and seriously pollutes the environment. Sebacoyl chloride has high activity and is easy to hydrolyze. It must be anhydrous du...

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  • Method for preparing bis(1-alkoxy-2,2,6,6-tetramethyl piperidine-4-yl) sebate
  • Method for preparing bis(1-alkoxy-2,2,6,6-tetramethyl piperidine-4-yl) sebate
  • Method for preparing bis(1-alkoxy-2,2,6,6-tetramethyl piperidine-4-yl) sebate

Examples

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Embodiment 1

[0059] A preparation method of bis(1-methoxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, comprising the steps of:

[0060] (1) Synthesis: 0.11mol (20.60g) of 1-methoxy-4-hydroxyl-2,2,6,6-tetramethylpiperidinol, 0.05mol (11.51g) of dimethyl sebacate and Add 100g of n-heptane into a 250mL three-necked flask with mechanical stirring, water separator and condenser, add ground 0.09mol (2.20g) lithium hydroxide and 0.003mol (1g) tetrabutylammonium bromide, and heat up To the reflux state (about 98°C), the methanol was continuously refluxed to separate, and the reaction was stopped when no methanol was separated after reflux (about 5h).

[0061] (2) Purification: After the reaction, cool down to room temperature, add 40mL×3 deionized water to wash 3 times, distill off the solvent and unreacted 1-methoxy-2,2,6,6-tetramethyl under reduced pressure Piperidinol obtained 27.47g of crude product, added the crude product into 55g m (methanol): m (water) = 0.8:1 mixed solvent, stirred for ...

Embodiment 2

[0070] A preparation method of bis(1-ethoxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, comprising the steps of:

[0071] (1) Synthesis: 0.11mol (22.11g) of 1-ethoxy-4-hydroxyl-2,2,6,6-tetramethylpiperidinol, 0.05mol (11.51g) of dimethyl sebacate and Add 100g of n-heptane into a 250mL three-necked flask equipped with a mechanical stirrer, a water separator, and a condenser, and add 0.09mol (2.20g) of lithium hydroxide and 0.003mol (about 1g) of tetrabutylammonium bromide after grinding, Raise the temperature to the reflux state (about 98°C), continuously reflux to separate methanol, and stop the reaction when no methanol is separated after reflux (about 5h).

[0072] (2) Purification: After the reaction, cool down to room temperature, add 40mL×3 deionized water to wash, and distill off the solvent and unreacted 1-ethoxy-2,2,6,6-tetramethylpiperidine under reduced pressure Alcohol yielded 26.95g of the crude product. Add the crude product to 55g of m (methanol): m (water) = 0...

Embodiment 3

[0080] A preparation method of bis(1-propoxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, comprising the steps of:

[0081] (1) Synthesis: 0.11mol (23.65g) of 1-propoxy-4-hydroxyl-2,2,6,6-tetramethylpiperidinol, 0.05mol (11.51g) of dimethyl sebacate and 100g of n-heptane was added to a 250mL three-necked flask equipped with a mechanical stirrer, a water separator and a condenser, and 0.09mol (2.20g) of lithium hydroxide and 0.003mol (about 1g) of tetrabutylammonium bromide were added into the ground, Raise the temperature to the reflux state (about 98°C), continuously reflux to separate methanol, and stop the reaction when no methanol is separated after reflux (about 5h).

[0082] (2) Purification: After the reaction, cool down to room temperature, add 40mL×3 deionized water to wash, and distill off the solvent and unreacted 1-propoxy-2,2,6,6-tetramethylpiperidine under reduced pressure The crude product was 30.65g, and the crude product was added to 60g m (methanol): m (wate...

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Abstract

The invention discloses a method for synthesizing bis(1-alkoxy-2,2,6,6-tetramethyl piperidine-4-yl) sebate. The bis(1-alkoxy-2,2,6,6-tetramethyl piperidine-4-yl) sebate is synthesized through transesterification by using dimethyl sebate and 1-alkoxy-2,2,6,6-tetramethylpipradrol as raw materials. According to the method, lithium hydroxide is adopted as a catalyst, a quaternary ammonium salt is adopted as a phase transfer catalyst, n-heptane is adopted as a methanol-carrying solvent, and methanol is separated continuously from the reaction system through a water knockout vessel. The process comprises the steps: adding dimethyl sebate, 1-alkoxy-2,2,6,6-tetramethylpipradrol, lithium hydroxide, the phase transfer catalyst and n-heptane to a reaction kettle with the water knockout vessel, performing heating to a reflux state so as to separate methanol continuously, stopping the reaction (about 5 hours later) until no separation of methanol, performing cooling to room temperature, performingwashing with deionized water, performing reduced pressure distillation on the oil phase so as to isolate the solvent and unreacted 1-alkoxy-2,2,6,6-tetramethylpipradrol and obtain a crude product, washing the crude product three times with a mixed solvent of methanol and water, and then performing distillation so as to isolate the solvent and obtain the final product. The method has the advantagesthat the process and the devices are simple, the catalyst has safe use, the product has easy separation, the product has high yield and high purity, and emission of three wastes is little.

Description

technical field [0001] The present invention relates to a preparation method of bis(1-alkoxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, specifically a sebacate Acid dimethyl ester and 1-alkoxy-2,2,6,6-tetramethylpiperidinol are raw materials, lithium hydroxide is a catalyst, quaternary ammonium salt is a phase transfer catalyst, and n-heptane is a methanol solvent. The invention discloses a transesterification method in which methanol is continuously separated from a reaction system by using a water separator, and belongs to the field of fine chemical industry and macromolecule material additives. Background technique [0002] Bis(1-alkoxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate is a novel light stabilizer (Papaspyrides C D, Kiliaris P .Polymer Green Flame Retardants[M].Amsterdam:Elsevier Science Ltd edited,2014:267-288), its general chemical structure is as follows: [0003] [0004] In the formula, R=alkane group, cycloalkane group and aromatic hydrocarbon group...

Claims

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Application Information

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IPC IPC(8): C07D211/94
Inventor 吴鸿志杨喜生赵震徐基海唐林生
Owner 山东兄弟科技股份有限公司
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