Gemini perfluoroalkylsulfonyloxybenzyl cationic surfactant as well as preparation and application thereof

A technology of perfluoroalkylsulfonyloxybenzylcation and perfluorobutylsulfonyloxy, which is applied in the field of surfactants, can solve the problems of high environmental hazards and unsatisfactory fire extinguishing effect, and achieve fire extinguishing performance Excellent, water-forming film-forming effect with fast spreading speed

Inactive Publication Date: 2013-12-18
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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  • Gemini perfluoroalkylsulfonyloxybenzyl cationic surfactant as well as preparation and application thereof
  • Gemini perfluoroalkylsulfonyloxybenzyl cationic surfactant as well as preparation and application thereof
  • Gemini perfluoroalkylsulfonyloxybenzyl cationic surfactant as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1 intermediate (M 1 , M 2 ) preparation

[0032] Add 12.4g (0.1mol) p-hydroxybenzyl alcohol, 17.9g (0.13mol) potassium carbonate, 200mL acetonitrile into a dry 1000mL flask, heat to reflux, slowly add 52.26g (0.13mol) perfluorobutylsulfonyl fluoride dropwise, The reaction was continued for 2.5 h, and the end point of the reaction was monitored by TCL. Add 150mL ethyl acetate to the reaction solution, wash 3 times with saturated sodium chloride solution, the organic layer is dried over anhydrous sodium sulfate, and solvent removal is obtained to obtain the colorless transparent liquid intermediate perfluorobutanesulfonic acid-4-(hydroxy Methyl) phenyl ester (M 1 ), 35.7g, the yield is 88%. 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-128.827(2F),-123.802(2F),-111.125(2F),-84.248(3F); MS(EI):406(M + ) (calculated value: 405.99).

[0033] Add 12.4g (0.1mol) p-hydro...

Embodiment 2

[0034] Embodiment 2 intermediate (M 3 , M 4 ) preparation

[0035] Add 44.66g (0.11mol) perfluorobutanesulfonic acid-4-(hydroxymethyl)phenyl ester (M 1 ), 200mL of 1,4-dioxane, slowly add 38.6g (0.22mol) of thionyl chloride dropwise under ice bath, react for 30min after the drop, raise the temperature to 60°C and continue the reaction for 1h, and monitor the end point 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 over anhydrous sodium sulfate, and precipitated to obtain a colorless liquid intermediate perfluorobutanesulfonic acid-4-(chloro Methyl) phenyl ester (M 3 ), 37.7g, the yield is 81%. 1 H NMR (400MHz, CDCl 3 ):δ4.56(s,2H,CH 2 ),6.90(d,2H,J=3.9Hz,phH),7.40(d,2H,J=4.2Hz,phH); 19 F NMR (376MHz, CDCl 3 ):δ-128.827(2F),-123.802(2F),-111.125(2F),-84.248(3F); MS(EI):424(M + ) (calculated value: 423.95).

[0036] Add 55.6g (0.11mol) perfluorohexylsul...

Embodiment 3

[0037] Example 3N, N, N'N'-tetramethyl-N, N'-bis((4-perfluorobutylsulfonyloxy)benzyl)ethane-1,2-diammonium salt (A 1 )Synthesis

[0038] Add 6.36g (0.015mol) perfluorobutanesulfonic acid-4-(chloromethyl)phenyl ester (M 3 ), 0.8g (7mmol) tetramethylethylenediamine, 150mL anhydrous acetonitrile, reflux reaction overnight, suction filtration, the obtained solid was washed three times with ether, and finally a white solid was obtained as the target compound (A 1 ), 6.41g, the yield is 95%. 1 H NMR(600MHz,DMSO):δ3.18(s,12H,N(CH 3 ) 2 ),4.096(s,4H,CH 2 ),4.762(s,4H,CH 2 ),7.71(d,4H,J=7.8Hz,phH),7.85(d,4H,J=12.0Hz,phH); 19 F NMR (376MHz, DMSO): δ-128.827 (2F), -123.802 (2F), -111.125 (2F), -84.248 (3F); HPLC / MS (ESI): 931.1 (M + ) (calculated value: 930.09).

[0039]

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Abstract

The invention discloses a gemini perfluoroalkylsulfonyloxybenzyl cationic surfactant as well as preparation and application thereof. The structural general formula of the surfactant is as shown in a formula I, wherein Rf is perfluorobutylsulfonyl or perfluorohexylsulfonyl; n is 2, 3, 4 or 6; X is a counter anion. The perfluorobutylsulfonyl or the perfluorohexylsulfonyl is a fluorine-containing precursor material; the gemini perfluoroalkylsulfonyloxybenzyl cationic surfactant is obtained through the sulfonation of the fluorine-containing precursor material with p-hydroxybenzylalcohol, chlorination with a halogenating reagent and quaternization with tetramethyl alkyl diamine. The gemini cationic surfactant provided by the invention is free of a perfluorooctyl group with a lasting organic pollutant characteristic, high in surface activity and low in critical micelle concentration; an aqueous film-forming foam fire extinguishing agent obtained by compounding the gemini cationic surfactant with additives is quick in aqueous film-forming spreading speed and excellent in fire extinguishing performance.

Description

technical field [0001] The invention relates to surfactants, in particular to a class of gemini-type perfluoroalkylsulfonyloxybenzyl cationic surfactants and their preparation and application. 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 ti...

Claims

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Application Information

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IPC IPC(8): B01F17/18B01F17/00C07C303/28C07C309/65A62D1/02C09K23/18C09K23/00
Inventor 涂海洋王乾有杨磊张爱东王珊魏玉敏周烈平
Owner HUAZHONG NORMAL UNIV
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