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Preparation method of bromized N,N-diallyl piperidine onium salt cationic monomer

A technology of diallyl piperidine and cationic monomers, which is applied in the field of preparation of N,N-diallyl piperidinium bromide salts of cationic monomers, and can solve complicated operations, many side reactions, many steps, etc. problem, to achieve the effect of increasing the reaction speed, improving the utilization rate and increasing the yield

Active Publication Date: 2015-03-25
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This synthetic route has the following problems: (1) there are many steps, at least two steps are required, and after the first allyl group is inserted, the intermediate product needs to be separated and purified, and the operation is cumbersome; (2) there are many side reactions, Especially when the first diallyl group is connected, a base needs to be added as an acid-binding agent to make the halopropene easy to hydrolyze; (3) the yield is low, especially when the second allyl group is connected due to steric hindrance , more difficult
However, the preparation method for obtaining N,N-diallylpiperidinium salt cationic monomer by one-step reaction using diallylamine as raw material has not yet been disclosed in relevant literature.

Method used

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  • Preparation method of bromized N,N-diallyl piperidine onium salt cationic monomer
  • Preparation method of bromized N,N-diallyl piperidine onium salt cationic monomer
  • Preparation method of bromized N,N-diallyl piperidine onium salt cationic monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (1) The molar ratio of diallylamine, 1,5-dibromopentane and alkali is 4:1:1, and 54.2mL of diallyl and 5gK 2 CO 3 Add the solid to a 250mL three-neck flask equipped with a condenser, a constant pressure dropping funnel, and a mechanical stirrer, then add 40.7mL of water, stir evenly, raise the temperature to 60°C and start adding 15mL of 1,5-dibromopentane dropwise for 3 hours. Completed, continue to react for 3h, start to drop 19.2g K 2 CO 3 Saturated solution, after 2h addition, continue to react for 4h;

[0037] (2) The above-mentioned liquid phase was transferred into a separatory funnel, and after standing for 30 minutes, the liquid was separated to obtain 26 mL of the oil phase, which was recovered and entered into the next round of reaction;

[0038] (3) The water phase is evaporated and concentrated to nearly dryness, dissolved by adding absolute ethanol, and filtered to remove insoluble inorganic matter; evaporate the filtrate to a paste that can still flow,...

Embodiment 2

[0045] (1) Mix diallylamine, 1,5-dibromopentane and alkali in a molar ratio of 5:1:1.02, mix 67.8mL diallyl and 5.1g K 2 CO 3 Add the solid to a 250mL three-neck flask equipped with a condenser, a constant pressure dropping funnel and a mechanical stirrer, then add 67.8mL of water, stir evenly, raise the temperature to 65°C and start adding 15mL of 1,5-dibromopentane dropwise for 3.5h After dripping, continue to react for 2.5h, start to drop 19.5g K 2 CO 3 Saturated solution, after 2h addition, continue to react for 4h;

[0046] (2) The above-mentioned liquid phase was transferred into a separatory funnel, and after standing for 30 minutes, the liquid was separated to obtain 38.2 mL of the oil phase, which was recovered and entered into the next round of reaction;

[0047] (3) The water phase is evaporated and concentrated to nearly dryness, dissolved by adding absolute ethanol, and filtered to remove insoluble inorganic matter; evaporate the filtrate to a paste that can st...

Embodiment 3

[0051] (1) Mix diallylamine, 1,5-dibromopentane and alkali in a molar ratio of 6:1:1.05, mix 81.3mL diallyl and 5.24g K 2 CO 3 Add the solid to a 250mL three-necked flask equipped with a condenser, a constant pressure dropping funnel, and a mechanical stirrer, then add 81.3mL of water, stir evenly, raise the temperature to 70°C and start adding 15mL of 1,5-dibromopentane dropwise for 4 hours. Completed, continue to react for 2h, start to drop 20.1g K 2 CO 3 Saturated solution, after 2h addition, continue to react for 4h;

[0052] (2) The above-mentioned liquid phase was transferred into a separatory funnel, and after standing for 30 minutes, the liquid was separated to obtain 51.7 mL of the oil phase, which was recovered and entered into the next round of reaction;

[0053] (3) The water phase is evaporated and concentrated to nearly dryness, dissolved by adding absolute ethanol, and filtered to remove insoluble inorganic matter; evaporate the filtrate to a paste that can s...

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Abstract

The invention discloses a preparation method of a bromized N,N-diallyl piperidine onium salt cationic monomer. The preparation method comprises the following steps: performing a nucleophilic substitution reaction under an alkaline condition by taking diallyl amine and 1,5-dibromopentane as raw materials to prepare bromized N,N-diallyl piperidine onium salt by one step; subsequently skimming; recycling an oil phase; evaporating and concentrating a water phase; dissolving by using ethanol and then filtering; concentrating the filtrate into a viscous fluid; pouring acetone; crystalizing at a temperature below 5 DEG C; filtering; washing a filter cake by the acetone; and purifying to obtain high-purity bromized N,N-diallyl piperidine onium salt. The preparation method disclosed by the invention is simple in technical route, simple and convenient to operate, high in yield and low in cost; all the used solvents are recyclable; the generated inorganic bromine salt is recycled; few three wastes are generated; and the preparation method is environment-friendly in technological process and easy to industrialize. A product prepared by the method disclosed by the invention can be used as a high-molecular synthesized cationic monomer and can also be used as an organic synthesized midbody.

Description

technical field [0001] The invention belongs to the field of fine chemical industry and water treatment agent, and in particular relates to a preparation method of cationic monomer bromide N,N-diallylpiperidinium salt synthesized by polymer. Background technique [0002] Since the end of the 1940s to the beginning of the 1950s, American scholars Butler G B and Ingley F L first developed diallyl quaternary ammonium salt polymers. These polymers have good water solubility, high positive charge density, It has the advantages of low price, high efficiency, non-toxicity and bactericidal properties, and has been widely used in water treatment, oil exploration, daily chemical industry, textile printing and dyeing and other fields. After decades of development, p-dimethyldienyl ammonium chloride (DMDAAC) and its combination with alkenyl monomers (acrylamide, acrylic acid, sodium p-styrenesulfonate, etc.), SO 2 The R&D of copolymers such as Co., Ltd. has been carried out in depth, t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/06
CPCY02P20/582C07D211/02C07D211/06
Inventor 刘立华杨刚刚王易峰周智华唐安平
Owner HUNAN UNIV OF SCI & TECH
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