Bis(1-chloro-N-methylmorpholine onium-2-hydroxy propyl) n-octadecane amine quaternary ammonium salt and preparation method thereof

A technology of n-octadecylamine and methyl morpholinium, which is applied in the field of bis-n-octadecylamine quaternary ammonium salt and its preparation, and can solve the problem of unresearched morpholine inhibition performance, slow release property, single performance, etc. problem, to achieve the effect of low cost, simplified reaction post-processing, and simple operation

Inactive Publication Date: 2017-07-18
SHAANXI UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] There have been many studies on the synthesis and application of diquaternary ammonium salt corrosion inhibitors. In 2007, Popova et al. studied the inhibition of nitrogen-containing heterocyclic quaternary ammonium salts (including pyridine, quinoline, and benzothiazole) on acidic low-carbon steel. performance, by increasing the molecular surface area and changing the position of the substituent to improve the inhibition efficiency, but the inhibition per

Method used

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  • Bis(1-chloro-N-methylmorpholine onium-2-hydroxy propyl) n-octadecane amine quaternary ammonium salt and preparation method thereof
  • Bis(1-chloro-N-methylmorpholine onium-2-hydroxy propyl) n-octadecane amine quaternary ammonium salt and preparation method thereof
  • Bis(1-chloro-N-methylmorpholine onium-2-hydroxy propyl) n-octadecane amine quaternary ammonium salt and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0037] The preparation of two (1-chloro-N-methylmorpholinium-2-hydroxypropyl) n-octadecylamine quaternary ammonium salt comprises the following steps:

[0038] (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.

[0039] (2) Add 22.7 g (0.05 mol) of the intermediate prepared above, 10.1 g (0.1 mol) of N-methylmorpholine and 40 mL of absolute ethanol into another three-necked flask, and react under reflux at 80° C. for 4 h. Ethanol was evaporated, washed with isooctane, left to precipitate crystals, recrystallized with acetone, and dried in vacuum to obtain bis(1-chloro-N-methylmorpholinium-2-hydroxypropyl) n-octadecylamine quaternary ammonium...

Embodiment 2

[0041] The preparation of two (1-chloro-N-methylmorpholinium-2-hydroxypropyl) n-octadecylamine quaternary ammonium salt comprises the following steps:

[0042] (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.

[0043] (2) Add 2.5 g of the intermediate prepared in (1) to another three-necked flask, then add 1.11 g of N-methylmorpholine and 4 ml of absolute ethanol, and heat up to 70° C. for 8 hours. Rotary evaporation to remove ethanol, wash with isooctane, stand to precipitate crystals, recrystallize with acetone, and dry in vacuo to obtain bis(1-chloro-N-methylmorpholinium...

Embodiment 3

[0045]The preparation of two (1-chloro-N-methylmorpholinium-2-hydroxypropyl) n-octadecylamine quaternary ammonium salt comprises the following steps:

[0046] (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 the viscous liquid intermediate bis(1-chloro-2-hydroxypropyl) n-octadecylamine.

[0047] (2) Add 2.5 g of the intermediate prepared in (1) to another three-necked flask, then add 1.11 g of N-methylmorpholine and 4 ml of absolute ethanol, and heat up to 75° C. for 7 h. Rotary evaporation to remove ethanol, wash with isooctane, stand to precipitate crystals, recrystallize with acetone, and dry in vacuo to obtain bis(1-chloro-N-methylmorpholinium-2-h...

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Abstract

The invention discloses a bis(1-chloro-N-methylmorpholine onium-2-hydroxy propyl) n-octadecane amine quaternary ammonium salt and a preparation method thereof. The method comprises the steps of firstly adding octadecylamine and absolute ethyl alcohol to a reactor, dropwise adding epoxy chloropropane and fully stirring for reflux reaction and carrying out reduced pressure distillation and acetone washing to obtain bis(1-chloro-2-hydroxy propyl) n-octadecane amine; and adding the bis(1-chloro-2-hydroxy propyl) n-octadecane amine, N-methylmorpholine and the absolute ethyl alcohol to another reactor, carrying out full reflux reaction, distilling out ethyl alcohol, carrying out isooctane washing, placing precipitated crystal, carrying out recrystallization by using acetone and carrying out vacuum drying to obtain a target product. An intermediate is synthesized from octadecylamine and epoxy chloropropane as initiators and the absolute ethyl alcohol as a solvent, and a symmetric biquaternary ammonium salt compound is obtained through quaternization, so that penetration of a hydrophobic group and a hydrophilic group into a lipoid layer and a protein layer of a somatic cell separately is facilitated to cause enzyme inactivation and protein denaturation, and the bis(1-chloro-N-methylmorpholine onium-2-hydroxy propyl) n-octadecane amine quaternary ammonium salt has relatively high bactericidal ability.

Description

technical field [0001] The invention belongs to the field of fine organic synthesis, and specifically relates to a bis(1-chloro-N-methylmorpholinium-2-hydroxypropyl) n-octadecylamine quaternary ammonium salt and a preparation method thereof. Background technique [0002] Diquaternary ammonium salt compounds, 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. Stronger reduction of oil-water interfacial tension and less irritation to the skin. Because the heterocyclic diquaternary ammonium salt has a quaternary ammonium positive ion, the heterocyclic compound has a strong Π electronic functional group, which enables it to form a Π adsorption o...

Claims

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Application Information

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IPC IPC(8): C07D295/13B01F17/32B01F17/18A01N43/84A01P1/00A01P3/00C23F11/14C09K23/18C09K23/32
CPCA01N43/84C23F11/149C07D295/13C09K23/00
Inventor 郭睿马兰土瑞香宋博王映月李云鹏郭煜韩双
Owner SHAANXI UNIV OF SCI & TECH
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