Perfluorohexyl sulfonyloxy benzyl cation surfactant as well as preparation method and application thereof

A technology of sulfonyloxybenzyl cation and surfactant, which is applied in the field of perfluorohexylsulfonyloxybenzyl cationic surfactant and its preparation, can solve the problem of great environmental hazards and unsatisfactory fire extinguishing effect, etc. problem, to achieve the effect of excellent fire extinguishing performance, fast water film spreading speed and excellent surface activity

Inactive Publication Date: 2013-12-25
HUAZHONG NORMAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the foam fire extinguishing agents currently used contain PFOA/PFOS fluorine-containing surfactants. Although

Method used

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  • Perfluorohexyl sulfonyloxy benzyl cation surfactant as well as preparation method and application thereof
  • Perfluorohexyl sulfonyloxy benzyl cation surfactant as well as preparation method and application thereof
  • Perfluorohexyl sulfonyloxy benzyl cation surfactant as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1 intermediate (M 1 ) preparation

[0032] Add 12.4g (0.1mol) p-hydroxybenzyl alcohol, 17.9g (0.13mol) potassium carbonate, 200mL acetonitrile into a dry 250mL flask, heat to reflux, slowly add 65.3g (0.13mol) perfluorohexylsulfonyl fluoride dropwise, continue The reaction was carried out for 0.5 h, and the end point of the reaction was monitored by TLC. Add 150mL ethyl acetate to the reaction solution, wash 3 times with saturated sodium chloride solution, dry the organic layer with anhydrous sodium sulfate, and remove the solvent to obtain the colorless liquid intermediate perfluorohexylsulfonic acid-4-(hydroxymethyl ) phenyl ester (M 1 ), 44.53g, and the yield was 84%. 1 H NMR (400MHz, CDCl 3 ):δ2.50(s,1H,-OH),4.61(s,2H,-CH 2 -),6.89(d,2H,J=7.8Hz,phH),7.33(d,2H,J=7.8Hz,phH); 19 F NMR (376MHz, CDCl 3 ):δ-126.494(2F),-123.057(2F),-122.182(2F),-120.690(2F),-112.682(2F),-81.136(3F);MS(EI):506.03(M + ) (calculated value: 505.99).

Embodiment 2

[0033] Embodiment 2 intermediate (M 2 ) preparation

[0034] Add 55.6g (0.11mol) perfluorohexylsulfonate-4-(hydroxymethyl)phenyl ester (M 1 ), 200mL of 1,4-dioxane, slowly add 19.47g (0.165mol) of thionyl chloride dropwise under an ice bath, react for 30min after the drop is complete, raise the temperature to 60°C and continue the reaction for 1.0h, and monitor the end of the reaction by TLC. Slowly poured into ice water, added 200mL ethyl acetate, washed three times with saturated sodium chloride solution, dried the organic layer with anhydrous sodium sulfate, and precipitated to obtain a colorless liquid intermediate perfluorohexylsulfonic acid-4-(chloromethyl base) phenyl ester (M 2 ) 45.0g, the yield is 78%. 1 H NMR (400MHz, CDCl 3 ):δ3.42(s,2H,-CH 2 -),7.22(d,2H,J=3.9Hz,phH),7.41(d,2H,J=4.2Hz,phH); 19 F NMR (376MHz, CDCl 3 ):δ-126.494(2F),-123.057(2F),-122.182(2F),-120.690(2F),-112.682(2F),-81.136(3F); MS(EI):524.02(M + ) (calculated value: 523.95).

Embodiment 3

[0035] Embodiment 3 intermediate (M 3 ~ M 5 ) preparation

[0036] Add 6.36g (0.015mol) perfluorohexylsulfonate-4-(chloromethyl)phenyl ester (M 2 ), 8.4g (0.06mol) of potassium carbonate, 1.46g (0.018mol) of dimethylamine hydrochloride, 100mL of acetonitrile, reacted at 70-80°C for 2.0h, monitored by TLC, and the reaction was completed. Add 200mL ethyl acetate to the reaction solution, wash with saturated sodium chloride solution three times, dry the organic layer with anhydrous sodium sulfate, and remove the solvent to obtain the colorless liquid intermediate perfluorohexylsulfonic acid-4-(N,N- Dimethylaminomethyl) phenyl ester (M 3 ) 5.85g, the yield is 75%. 1 H NMR (400MHz, CDCl 3 ):δ3.07(s,6H,CH 3 ),4.66(s,2H,CH 2 ),7.69(d,2H,J=8.8Hz,phH),7.79(d,2H,J=8.8Hz,phH); 19 FNMR (376MHz, CDCl 3 ):δ-126.494(2F),-123.057(2F),-122.182(2F),-120.690(2F),-112.682(2F),-81.136(3F); MS(EI):533.04(M + ) (calculated value: 533.03).

[0037] Add 6.36g (0.015mol) perfluorohexylsulfon...

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Abstract

The invention discloses a perfluorohexyl sulfonyloxy benzyl cation surfactant as well as a preparation method and application thereof. The surfactant has the general structural formula which is shown as a formula I, wherein R1 and R2 are -CH3, -CH2CH3 or -CH2CH2OH; R3 is -H, -CH3, -CH2CH3, -CH2COOC2H5 or -CH2COOC4H9; X is an anion. The cation surfactant disclosed by the invention is obtained by taking perflurohexane sulphonyl fluoride as a precursor material, performing sulfonic acid esterification with p-hydroxyphenyl methanol, performing halogenation with a halogenating agent, performing ammoniation with secondary amine, and performing quaternization with halogen hydride or halohydrocarbon. The cation surfactant disclosed by the invention does not contain perfluorooctyl groups with persistent organic pollutant characteristics; the surface activity is high; the critical micelle concentration is low; an aqueous film forming foam extinguishing agent obtained by compounding the perfluorohexyl sulfonyloxy benzyl cation surfactant has high aqueous film-forming spreading speed, and excellent extinguishing performance.

Description

technical field [0001] The invention relates to surfactants, in particular to a class of perfluorohexylsulfonyloxybenzyl cationic surfactants and a preparation method and application thereof. Background technique [0002] Compared with ordinary surfactants, fluorine-containing surfactants have outstanding properties of "three highs and two phobias", that is, high surface activity, high heat resistance stability and chemical inertness, that is, water and oil repellency, and fluorine-containing surface activity Due to its unique properties, the agent has a wide range of uses in the fields of petroleum, fire protection, sterilization, papermaking, textiles, and cleaning agents. For example, in oil exploration, fluorine-containing surfactants can improve oil displacement efficiency due to their low surface tension; in fire protection, fluorine-containing surfactants are added to ordinary foam fire extinguishing agents, and the fire extinguishing speed can be increased by 3-4 tim...

Claims

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Application Information

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IPC IPC(8): B01F17/18C07C309/65C07C303/30A62D1/02C09K23/18
Inventor 张爱东王乾有杨磊涂海洋王珊魏玉敏周烈平
Owner HUAZHONG NORMAL UNIV
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