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1,1'-dialkyl-3,3'-(2-phosphate-1,3-propylidene)imidazolium compound and preparation method thereof

A technology of alkyl imidazole and alkyl benzimidazole, which is applied in the field of 1,1'-dialkyl-3,3'-imidazole inner salt compound and its preparation, can solve problems such as difficult synthesis, and reduce corrosiveness , The synthesis method is simple, and the water solubility is good.

Inactive Publication Date: 2014-07-30
QIQIHAR UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this type of active agent is difficult to synthesize, and there are few research reports on it, and there are even fewer reports on amphoteric phosphate gemini surfactants. However, the unique structure and properties of amphoteric gemini surfactants determine their good wettability. , washing, emulsifying, low irritation, low toxicity, salt resistance, temperature resistance and acid and alkali advantages

Method used

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  • 1,1'-dialkyl-3,3'-(2-phosphate-1,3-propylidene)imidazolium compound and preparation method thereof
  • 1,1'-dialkyl-3,3'-(2-phosphate-1,3-propylidene)imidazolium compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The first step: the synthesis of 1,3-dichloro-2-propanol

[0038] Add 30.0 g of 36% concentrated HCl to a three-necked flask equipped with a stirrer and a thermometer, and then add 24.5 g of epichlorohydrin dropwise, and the dropwise addition is completed in about half an hour, and the temperature is controlled between 30°C and 40°C. About 7~9 h of reaction. Separation was carried out with a separatory funnel to obtain the organic phase, and the organic phase was separated with anhydrous MgSO 4 Dry for about 4-5 h, filter to remove magnesium sulfate, and distill under normal pressure to collect fractions at 175°C-177°C to obtain 23.9 g of colorless liquid 1,3-dichloro-2-propanol with a yield of 70.0%.

[0039] 1,3-Dichloro-2-propanol 1 H NMR (400 MHz, DMSO-d 6 ) δ H : 3.15 (1H, d, J = 6.4 Hz, -OH), 3.70 (4H, d, J = 5.6 Hz, 2-CH 2 Cl), 4.08 (1H, m, -CH(OH)-).

[0040] The second step: the synthesis of N-octylimidazole

[0041] Add 0.440 g (11.0 mmol) NaO...

Embodiment 2

[0050] The second step: the synthesis of N-decyl imidazole

[0051] Add 0.440 g (11.0 mmol) NaOH, 0.714 g (10.5 mmol) imidazole and 10 mL dimethylsulfoxide (DMSO) into a three-necked flask equipped with a stirrer and a thermometer, and stir at 20°C to 25°C under nitrogen protection until To the transparent solution, 2.21 g (10.0 mmol) of decane bromide was added dropwise, and after about 4~6 h of reaction, the reactant was poured into 10 mL of water, extracted with 3×10 mL of chloroform, and the chloroform layer was washed with water 4~5 times, then use anhydrous MgSO 4 Dry, filter to obtain the filtrate, remove chloroform to obtain 1.84 g of light yellow liquid N-decyl imidazole, yield 88.3%.

[0052] 1 H-NMR (400 MHz, CDCl 3 ) d H : 7.59 (1H, s, imidazole ring 2-CH), 7.07 (1H, s, imidazole ring 4-CH), 6.91 (1H, s, imidazole ring 5-CH), 3.94 (2H, t, J = 7.2 Hz, -CH linked to the imidazole ring 2 -), 1.78 (2H, m, -CH 2 -), 1.28 (10H, m, -(CH 2 ) 7 -), 0.87 (3H, t, ...

Embodiment 3

[0060] The second step: the synthesis of N-dodecyl imidazole

[0061] Add 0.440 g (11.0 mmol) NaOH, 0.714 g (10.5 mmol) imidazole and 10 mL dimethylsulfoxide (DMSO) into a three-necked flask equipped with a stirrer and a thermometer, and stir at 20°C to 25°C under nitrogen protection until To a transparent solution, 2.49 g (10.0 mmol) of dodecane bromide was added dropwise, and after about 4~6 h of reaction, the reactant was poured into 10 mL of water, extracted with 3×10 mL of chloroform, and then washed with chloroform Layer 4~5 times, then use anhydrous MgSO 4 Dry, filter to obtain the filtrate, remove chloroform to obtain 2.08 g of light yellow liquid N-dodecyl imidazole, yield 88.1%.

[0062] 1 H-NMR (400 MHz, CDCl 3 ) d H : 7.70 (1H, s, 2-CH of imidazole ring), 7.09 (1H, s, 4-CH of imidazole ring), 6.93 (1H, s, 5-CH of imidazole ring), 3.96 (2H, t, J = 7.2 Hz, -CH linked to the imidazole ring 2 -), 1.78 (2H, m, -CH 2 -), 1.24-1.28 (10H, m, -(CH 2 ) 9 -), 0.88 ...

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Abstract

The invention relates to a 1,1'-dialkyl-3,3'-(2-phosphate-1,3-propylidene)imidazolium compound and a preparation method thereof. The structural formula of the 1,1'-dialkyl-3,3'-(2-phosphate-1,3-propylidene)imidazolium compound is shown in the specification, wherein n is 6, 8, 10, 12 and 14, and the alkyl imidazole can be replaced with alkyl benzimidazole. The 1,1'-dialkyl-3,3'-(2-phosphate-1,3-propylidene)imidazolium is a amphoteric dimeric surfactant, and a concrete synthesis method comprises the following steps: synthesizing 1, 3-dichloro-2-propanol, synthesizing N-alkyl imidazole, synthesizing 1,1'-dialkyl-3,3'-(2-hydroxyl-1,3-propylidene)imidazole hydrochloride, and synthesizing 1,1'-dialkyl-3,3'-(2-phosphate-1,3-propylidene)imidazolium. The 1,1'-dialkyl-3,3'-(2-phosphate-1,3-propylidene)imidazolium compound and the preparation method are easily available in raw materials, the reaction technology conditions are easy to control, operation is simple, the product is easy to purify, and yield is high. The compound has low critical micelle concentration, and can be used as a wetting agent, an emulsifier, a foaming agent and a foam stabilizer. A molecular structure has macrocyclic cefpimizole group and phosphate ester, and thus the compound has good thermal stability, solubility, salinity resistance, temperature resistance and acid and base resistance.

Description

technical field [0001] The invention relates to the field of fine chemicals, in particular to 1,1'-dialkyl-3,3'-(2-phosphate-1,3-propylene)imidazole inner salt compound and a preparation method thereof. Background technique [0002] Gemini surfactant is an emerging hot research direction in the field of surfactant in recent years. The Gemini surfactant structure usually consists of two or more hydrophilic and hydrophobic groups, and is connected by a spacer group (or linking group) through a chemical bond at or near the hydrophilic group. Among the many different types of gemini surfactants, Gemini zwitterionic and cationic surfactants are the two with the best performance. Amphoteric gemini surfactants mainly refer to gemini surfactants composed of part cations and part anions, which can form internal salts through intramolecular interactions in water. At the same time, some amphoteric gemini active agents can be used in combination with various surfactants in different p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6506B01F17/32B01F17/14C09K23/14C09K23/32
Inventor 王丽艳邓启刚郑永杰霍世超刘佳孙竹
Owner QIQIHAR UNIVERSITY
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