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Preparation method of 1,1'-dialkyl-3,3'-(2-phosphate-1,3-propylene) imidazole inner salt compound

A technology of alkylimidazole and dialkyl, which is applied in the field of preparation of 1,1'-dialkyl-3,3'-imidazole internal salt compound, can solve problems such as difficult synthesis, and achieve reduced corrosion and low interface Tension, the effect of cheap and easy-to-obtain raw materials

Inactive Publication Date: 2016-05-18
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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  • Preparation method of 1,1'-dialkyl-3,3'-(2-phosphate-1,3-propylene) imidazole inner salt compound
  • Preparation method of 1,1'-dialkyl-3,3'-(2-phosphate-1,3-propylene) imidazole inner salt compound
  • Preparation method of 1,1'-dialkyl-3,3'-(2-phosphate-1,3-propylene) imidazole inner salt compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The first step: the synthesis of 1,3-dichloro-2-propanol

[0037] Add 30.0g of 36% concentrated HCl to a three-neck flask equipped with a stirrer and a thermometer, and then add 24.5g of epichlorohydrin dropwise, and the dropwise addition is completed in about half an hour. The temperature is controlled between 30°C and 40°C, about Reaction 7~9h. 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 hours, remove magnesium sulfate by filtration, and collect fractions at 175°C~177°C by atmospheric distillation to obtain 23.9g of colorless liquid 1,3-dichloro-2-propanol, with a yield of 70.0%.

[0038] 1,3-Dichloro-2-propanol 1 HNMR (400MHz, DMSO-d 6 )δ H :3.15(1H,d,J=6.4Hz,-OH), 3.70(4H,d,J=5.6Hz,2-CH 2 Cl), 4.08 (1H,m,-CH(OH)-).

[0039] The second step: the synthesis of N-octylimidazole

[0040] Add 0.440g (11.0mmol) NaOH, 0.714g (10.5mmol) imidazole and 10mL d...

Embodiment 2

[0049] The second step: the synthesis of N-decyl imidazole

[0050] Add 0.440g (11.0mmol) NaOH, 0.714g (10.5mmol) imidazole and 10mL dimethyl sulfoxide (DMSO) to a three-neck flask equipped with a stirrer and a thermometer, and stir until transparent under nitrogen protection at 20°C~25°C Solution, add 2.21g (10.0mmol) of decane bromide dropwise, after about 4~6h of reaction, pour the reactant into 10mL water, extract 3×10mL with chloroform, and wash the chloroform layer with water 4~5 times , then with 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%.

[0051] 1 H-NMR (400MHz, CDCl 3 ) d H :7.59(1H, s, 2-CH of imidazole ring), 7.07(1H, s, 4-CH of imidazole ring), 6.91(1H, s, 5-CH of imidazole ring), 3.94(2H, t, J =7.2Hz, -CH connected to the imidazole ring 2 -),1.78(2H,m,-CH 2 -),1.28(10H,m,-(CH 2 ) 7 -),0.87(3H,t,J=7.2Hz,-CH 3 ).

[0052] The third step: Synthesis of 1,1'-...

Embodiment 3

[0059] The second step: the synthesis of N-dodecyl imidazole

[0060] Add 0.440g (11.0mmol) NaOH, 0.714g (10.5mmol) imidazole and 10mL dimethyl sulfoxide (DMSO) to a three-neck flask equipped with a stirrer and a thermometer, and stir until transparent under nitrogen protection at 20°C~25°C solution, add 2.49g (10.0mmol) of dodecane bromide dropwise, react for about 4~6h, pour the reactant into 10mL water, extract 3×10mL with chloroform, and wash the chloroform layer with water for 4~5 times, and then with 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%.

[0061] 1 H-NMR (400MHz, CDCl 3 ) d H :7.70(1H,s, imidazole ring 2-CH), 7.09(1H,s, imidazole ring 4-CH), 6.93(1H,s, imidazole ring 5-CH), 3.96(2H,t,J =7.2Hz, -CH connected to the imidazole ring 2 -),1.78(2H,m,-CH 2 -),1.24-1.28(10H,m,-(CH 2 ) 9 -),0.88(3H,t,J=7.2Hz,-CH 3 ).

[0062] Step 3: Synthesis of 1,1′-bis(dodecyl)...

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Abstract

The invention relates to a preparation method of 1,1'-dialkyl-3,3'-(2-phosphate-1,3-propylene) imidazole inner salt compound. The 1,1'-dialkyl) 3,3'-(2-phosphate-1,3-propylene) imidazole inner salt compound of the present invention is an amphoteric gemini surfactant, and the specific synthesis method includes 1, Synthesis of 3-dichloro-2-propanol, synthesis of N-alkylimidazole, 1,1'-dialkyl-3,3'-(2-hydroxy-1,3-propylene)imidazole hydrochloride The synthesis of the salt and the synthesis of the 1,1'-dialkyl-3,3'-(2-phosphate-1,3-propylene) imidazole inner salt are four steps. The 1,1'-dialkyl-3,3'-(2-phosphate-1,3-propylene) imidazolium internal salt of the present invention and the preparation method thereof have easy-to-obtain raw materials, easy-to-control reaction process conditions, and easy operation. Simple, the product is easy to purify, and the yield is high. The substance has a low critical micelle concentration and is useful as a wetting agent, emulsifier, foaming and foam stabilizer. The macrocyclic imidazole head group and phosphate group in the molecular structure make it have good thermal stability, solubility, salt resistance, temperature resistance and acid and alkali resistance.

Description

technical field [0001] The invention relates to the field of fine chemical industry, in particular to a preparation method of 1,1'-dialkyl-3,3'-(2-phosphate-1,3-propylene) imidazole inner salt compound. Background technique [0002] Gemini surfactants have become a hot research direction in the field of surfactants 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) at or near the hydrophilic group through a chemical bond. Among the many different types of gemini surfactants, Gemini zwitterionic and cationic surfactants are the two types 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 medi...

Claims

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Application Information

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Patent Type & Authority Patents(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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