Bi(1-chlorine-N-hydroxyethyl morpholinium-3-hydroxy propyl group)n-octadecylamine quaternary ammonium salt and preparation method thereof

A technology of hydroxyethyl morpholinium and n-octadecylamine, which is applied in the field of di-n-octadecylamine quaternary ammonium salt and its preparation, can solve the problem of poor slow release performance, single synthetic substance performance, and poor water solubility of metronidazole and other problems, to achieve the effect of simplifying the post-reaction treatment, optimizing the reaction conditions, and improving the corrosion inhibition effect.

Inactive Publication Date: 2017-04-05
SHAANXI UNIV OF SCI & TECH
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Problems solved by technology

[0005] There have been many studies on the synthesis and application of diquaternary ammonium fungicides. In 2014, Wang Yanping synthesized bis(1- Chloride-N-methylmorpholinium-2-hydroxypropyl) n-dodecylamine quaternary ammonium salt, its slow-release performance is poor; in 2014 Qin Shuang used epichlorohydrin, didecyldimethyl Ammonium chloride, metronidazole, acetic acid and hydrochloric acid were used as raw materials to synthesize a nitroimidazoline modified double-chain quaternary ammonium salt in one step, but metronidazole has poor water solubility and no surface activity, so it cannot kill SRB; Zhu Xun et al. used tetradecylamine, formaldehyde and formic acid as raw materials to synthesize dichloro-bis(N,N-dimethyl-N-tetradecyl) through methylation reaction and quaternization two-step method -2-Hydroxy-1,3-propanediamine quaternary ammonium salt, this synthetic substance has single performance and does not have sustained release

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  • Bi(1-chlorine-N-hydroxyethyl morpholinium-3-hydroxy propyl group)n-octadecylamine quaternary ammonium salt and preparation method thereof
  • Bi(1-chlorine-N-hydroxyethyl morpholinium-3-hydroxy propyl group)n-octadecylamine quaternary ammonium salt and preparation method thereof
  • Bi(1-chlorine-N-hydroxyethyl morpholinium-3-hydroxy propyl group)n-octadecylamine quaternary ammonium salt and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0043] The preparation of two (1-chloro-N-hydroxyethylmorpholinium-2-hydroxypropyl) n-octadecylamine quaternary ammonium salt may further comprise the steps:

[0044] (1) First add 10.70g (0.05mol) of octadecylamine and 40mL of absolute ethanol to the three-necked flask, stir continuously at 300r / min, raise the temperature to 40°C, add 9.25g (0.1mol) of epichlorohydrin dropwise, and reflux the reaction 12h. Distilled under reduced pressure and washed with acetone to obtain bis(1-chloro-2-hydroxypropyl) n-octadecylamine as a viscous liquid intermediate.

[0045] (2) Add 18.5 g (0.05 mol) of the intermediate prepared above, 13.1 g (0.1 mol) of N-hydroxyethylmorpholine and 40 mL of absolute ethanol into another three-necked flask, and react under reflux at 80° C. for 3 h. Ethanol is distilled off, washed with isooctane, placed to precipitate crystals, washed with acetone and purified, and dried in vacuum to obtain bis(1-chloro-N-hydroxyethylmorpholinium-2-hydroxypropyl) n-octade...

Embodiment 2

[0047] The preparation of two (1-chloro-N-hydroxyethylmorpholinium-2-hydroxypropyl) n-octadecylamine quaternary ammonium salt may further comprise the steps:

[0048] (1) First add 3g of octadecylamine to the three-necked flask, then add 10ml of absolute ethanol to dissolve it, then heat up to 50°C, stir and add 2.07g of epichlorohydrin (the drop rate is 30 drops / min), Reflux reaction 8h. After the reaction, the ethanol was distilled off under reduced pressure, washed with acetone, and the acetone was removed by rotary evaporation to obtain bis(1-chloro-2-hydroxypropyl) n-octadecylamine, a viscous liquid intermediate.

[0049] (2) Add 2.5 g of the intermediate prepared in (1) to another three-necked flask, then add 1.31 g of N-hydroxyethylmorpholine and 4 ml of absolute ethanol, and heat up to 50° C. for 8 hours. Rotary evaporation to remove ethanol, wash with isooctane, stand to precipitate crystals, wash with acetone and purify, and dry in vacuum to obtain bis(1-chloro-N-hy...

Embodiment 3

[0051]The preparation of two (1-chloro-N-hydroxyethylmorpholinium-2-hydroxypropyl) n-octadecylamine quaternary ammonium salt may further comprise the steps:

[0052] (1) First add 3g of octadecylamine to the three-necked flask, then add 10ml of absolute ethanol to dissolve it, then heat up to 60°C, stir and add 2.07g of epichlorohydrin (the drop rate is 30 drops / min), Reflux reaction 8h. After the reaction, the ethanol was distilled off under reduced pressure, washed with acetone, and the acetone was removed by rotary evaporation to obtain bis(1-chloro-2-hydroxypropyl) n-octadecylamine, a viscous liquid intermediate.

[0053] (2) Add 2.5 g of the intermediate prepared in (1) to another three-necked flask, then add 1.31 g of N-hydroxyethylmorpholine and 4 ml of absolute ethanol, and heat up to 60° C. for 7 hours. Rotary evaporation to remove ethanol, wash with isooctane, stand to precipitate crystals, wash with acetone for purification, and vacuum dry to obtain bis(1-chloro-N-...

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Abstract

The invention discloses a bi(1-chlorine-N-hydroxyethyl morpholinium-3-hydroxy propyl group)n-octadecylamine quaternary ammonium salt and a preparation method thereof. The method comprises the following steps: octadecylamine and absolute ethyl alcohol are added in a 3-mouth flask, continuously stirred, heated, and chloropropylene oxide is added, and the materials are fully reacted to obtain an intermediate bi(1-chlorine-2-hydroxy propyl group) n-octadecylamine, the above intermediate, N-hydroxyethyl morpholine and absolute ethyl alcohol are added in another flask, are subjected to a full backflow reaction to obtain a bi(1-chlorine-N-hydroxyethyl morpholinium-3-hydroxy propyl group)n-octadecylamine quaternary ammonium salt compound. The compound has sterilization performance and corrosion inhibition performance, and the preparation method has the advantages of simple operation, optimization of the reaction conditions, simplification of reaction post-processing, and low cost.

Description

[0001] 【Technical field】 [0002] The invention belongs to the field of fine organic synthesis, and in particular relates to a bis(1-chloro-N-hydroxyethylmorpholinium-2-hydroxypropyl) n-octadecylamine quaternary ammonium salt and a preparation method thereof. [0003] 【Background technique】 [0004] Diquaternary ammonium fungicides, also known as Gemini-type Gemini surfactants, are a type of special surfactants with 2 hydrophilic groups and 2 lipophilic groups. Compared with traditional surfactants, gemini surfactants have high surface activity, low critical micelle concentration and Krafft point, better water solubility, and can be combined with most traditional surfactants to produce stronger synergistic effects. It has the advantages of lowering the interfacial tension of oil and water and less irritation to the skin, so its application field continues to expand. [0005] There have been many studies on the synthesis and application of diquaternary ammonium fungicides. In 2...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/13C02F1/50
CPCC07D295/13C02F1/50C02F2303/04C02F2303/08
Inventor 郭睿马兰宋博郭煜土瑞香王映月李云鹏王宁
Owner SHAANXI UNIV OF SCI & TECH
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