CN1712093A - Organic substance extraction in water with ionic liquid as extractant - Google Patents

Organic substance extraction in water with ionic liquid as extractant Download PDF

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Publication number
CN1712093A
CN1712093A CN 200410049612 CN200410049612A CN1712093A CN 1712093 A CN1712093 A CN 1712093A CN 200410049612 CN200410049612 CN 200410049612 CN 200410049612 A CN200410049612 A CN 200410049612A CN 1712093 A CN1712093 A CN 1712093A
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ionic liquid
extraction
alkyl
charged ion
aqueous solution
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CN100345608C (en
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张锁江
李闲
张建敏
陈玉焕
张延强
孙宁
张香平
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Institute of Process Engineering of CAS
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Institute of Process Engineering of CAS
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Extraction Or Liquid Replacement (AREA)

Abstract

An application of the novel ionic liquid as extractant for extracting organic substance from water is disclosed. Its advantages are high effect and no loss of extractant.

Description

Novel ion liquid is as organism in the extraction agent extraction water
Technical field:
The present invention relates to a kind of being used for from the novel ion liquid of aqueous solution extraction organic substance.
Background technology:
Ionic liquid (Ionic liquids) is found in 1914, but up to 1992, Wikes leader's research group synthesized low melting point, anti-hydrolysis, stable strong 1-ethyl-3-methyl imidazolium tetrafluoroborate ionic liquid ([emim] BF 4), developed the ionic liquid of a series of excellent propertys subsequently again, just make ionic liquid research develop rapidly.Ionic liquid is compared with ionogen with traditional organic solvent, and have a series of outstanding advantages: (1) does not almost have vapour pressure, and is non-volatile; Colourless, odorless; (2) has bigger equilibrium temperature scope, the electrochemical stability potential window of better chemical stability and broad; (3) have the good solubility energy, with inorganic substance good solute effect is arranged all much organic.(4) ion liquid character has controllability, by changing ion liquid zwitterion collocation, can obtain the ionic liquid of different effect of extracting.
Existing a lot of ionic liquids are used for the report of extracting and separating both at home and abroad.Rogers etc. have measured several aromatics at water and ionic liquid 1-butyl-3-Methylimidazole hexafluorophosphate ([bmim] PF 6) in partition ratio, propose ionic liquid and be expected to substitute traditional easy volatile organic solvent and be used for extracting and separating.Wei Guor-Tzol etc. use [bmim] PF 6From aqueous phase extraction Ag +Deng metal ion, obtained extraordinary effect of extracting.At present be applied to used ionic liquid in the isolating report of liquid-liquid extraction and mostly be common hydrophobic ionic liquid as [bmim] PF at ionic liquid 6Deng, such ionic liquid has the raw materials cost height, the complicated and shortcomings such as hydrolysis easily, poor heat stability of synthesis step, and the research and development that therefore is used for the isolating novel ion liquid of liquid-liquid extraction is an important directions of present ionic liquid research.Employed ionic liquid is recent synthetic novel ion liquid among the present invention, and the research that is applied to extracting and separating is not seen in report as yet.
Summary of the invention:
The present invention proposes a kind of novel ion liquid as organic substance in the extraction agent extraction water.
This ionic liquid has that raw materials cost is low, synthesis step is simple, productive rate is high, stable in properties, advantage such as facile hydrolysis not, for the effect of extracting of organic substance in the water than [bmim] PF 6Better etc. conventional ion liquid.
Employed ionic liquid is the ionic compound that is made of a kind of negatively charged ion and a kind of positively charged ion among the present invention, and wherein positively charged ion is the season phosphonium salt or quaternary ammonium salt that alkyl replaces, and the chain length of alkyl is C 1-C 20, negatively charged ion is the benzene sulfonamide acid group, the chain length of alkyl is C 1-C 20
The novel ion liquid that the present invention proposes is used for the extraction water organic substance, and wherein organism is alkane, alkene, alkynes, alcohol, aldehyde, ketone, ether, ester, aromatics, aminated compounds, halohydrocarbon etc.Organic aqueous solution is any concentration, and extraction temperature is an arbitrary temp, and ionic liquid is any ratio with aqueous solution volume ratio, and the extraction time is unrestricted.
Embodiment:
The present invention illustrates with following embodiment, but the present invention is not limited to following embodiment, in the scope of described aim, changes and implements to be included in the technical scope of the present invention before and after not breaking away from.
Embodiment 1
Ionic liquid (P as extraction agent 666,14LABS) structure is as follows:
With above-mentioned ionic liquid and concentration is that the phenol solution of 0.01mol/L mixes and carries out the single-stage extraction test, and extraction temperature is 20 ℃, and the volume ratio of ionic liquid and phenol solution is 1: 1, extracts time 30min.
The single-stage extraction rate of phenol can reach 94%.
Embodiment 2
Ionic liquid (P as extraction agent 666,14LABS) structure is as follows:
With above-mentioned ionic liquid and concentration is that the phenol solution of 0.1mol/L mixes and carries out the single-stage extraction test, and extraction temperature is 20 ℃, and the volume ratio of ionic liquid and phenol solution is 1: 1, extracts time 30min.
The single-stage extraction rate of phenol can reach 94%.
Embodiment 3
Ionic liquid (P as extraction agent 666,14LABS) structure is as follows:
With above-mentioned ionic liquid and concentration is that the phenol solution of 0.01mol/L mixes and carries out the single-stage extraction test, and extraction temperature is 50 ℃, and the volume ratio of ionic liquid and phenol solution is 1: 10, extracts time 1h.
The single-stage extraction rate of phenol can reach 94%.
Embodiment 4
Ionic liquid (P as extraction agent 666,14LABS) structure is as follows:
With above-mentioned ionic liquid and concentration is that the ortho-cresol aqueous solution of 0.01mol/L is carried out the single-stage extraction test, and extraction temperature is 20 ℃, and the volume ratio of ionic liquid and the ortho-cresol aqueous solution is 1: 1, extracts time 30min.
The single-stage extraction rate of ortho-cresol can reach 99%.
Embodiment 5
Ionic liquid (P as extraction agent 666,14LABS) structure is as follows:
With above-mentioned ionic liquid and concentration is that the pyrocatechol aqueous solution of 0.01mol/L is carried out the single-stage extraction test, and extraction temperature is 20 ℃, and the volume ratio of ionic liquid and the pyrocatechol aqueous solution is 1: 1, extracts time 30min.
The single-stage extraction rate of pyrocatechol can reach 82%.
Embodiment 6
Ionic liquid (P as extraction agent 444,14LABS) structure is as follows:
With above-mentioned ionic liquid and concentration is that the phenol solution of 0.01mol/L mixes and carries out the single-stage extraction test, and extraction temperature is 20 ℃, and the volume ratio of ionic liquid and phenol solution is 1: 10, extracts time 30min.
The single-stage extraction rate of phenol can reach 91%.

Claims (3)

1, use novel alkyl benzene sulphonate (ABS) season phosphonium salt and alkyl benzene sulphonate (ABS) quaternary ammonium salt ionic liquid from the aqueous solution, extract organism as extraction agent, employed ionic liquid is the ionic compound that is made of a kind of negatively charged ion and a kind of positively charged ion, wherein positively charged ion is the season phosphonium salt or quaternary ammonium salt that alkyl replaces, and the chain length of alkyl is C 1-C 20, negatively charged ion is the benzene sulfonamide acid group, the chain length of alkyl is C 1-C 20
2, according to right 1 described method, wherein organism can be alkane, alkene, alkynes, alcohol, aldehyde, ketone, ether, ester, aromatics, organic acid, amine, halohydrocarbon etc., but is not limited to above-mentioned organism.
3, according to right 1 described method, organic aqueous solution is any concentration, and extraction temperature is an arbitrary temp, and ionic liquid and aqueous solution volume ratio are arbitrary proportion, and the extraction time is unrestricted, and extraction process and equipment do not have special restriction.
CNB2004100496126A 2004-06-22 2004-06-22 Organic substance extraction in water with ionic liquid as extractant Active CN100345608C (en)

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CN100345608C CN100345608C (en) 2007-10-31

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101058552B (en) * 2006-04-18 2010-12-08 上海师范大学 Double-functional group ionic liquid and preparation method
CN103073588A (en) * 2012-12-11 2013-05-01 宁波豪城合成革有限公司 Functional ionic liquid and its application
CN103420802A (en) * 2012-05-24 2013-12-04 北京化工大学 Novel method for separating phenolic compound from oil
CN104084593A (en) * 2014-07-03 2014-10-08 北京工业大学 Method for extracting nano-silver in ionic liquid separation and enrichment liquid
CN107382675A (en) * 2017-08-08 2017-11-24 东莞理工学院 A kind of extracting process of hydroxytyrosol
CN107399779A (en) * 2017-08-09 2017-11-28 北京盖雅环境科技有限公司 A kind of processing method of phenol wastewater

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100861916B1 (en) * 2001-03-26 2008-10-09 닛신보세키 가부시키 가이샤 Ionic liquid, electrolyte salt for storage device, electrolytic solution for storage device, electric double layer capacitor, and secondary battery
DE10206808A1 (en) * 2002-02-19 2003-08-28 Oxeno Olefinchemie Gmbh Separation of organic compounds, e.g. of 4C mixtures, involves liquid-liquid or liquid-gas extraction using an ionic liquid-containing phase
CN100424259C (en) * 2002-12-12 2008-10-08 中国科学院化学研究所 Room temperature ionic liquid containing unsaturated double bond and its prepn and application
CN1425657A (en) * 2002-12-30 2003-06-25 中国科学院兰州化学物理研究所 Olefine epoxidation method in ionic liquid

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101058552B (en) * 2006-04-18 2010-12-08 上海师范大学 Double-functional group ionic liquid and preparation method
CN103420802A (en) * 2012-05-24 2013-12-04 北京化工大学 Novel method for separating phenolic compound from oil
CN103420802B (en) * 2012-05-24 2016-04-13 北京化工大学 A kind of method of novel separating phenols compounds from oil
CN103073588A (en) * 2012-12-11 2013-05-01 宁波豪城合成革有限公司 Functional ionic liquid and its application
CN103073588B (en) * 2012-12-11 2015-04-15 宁波豪城合成革有限公司 Functional ionic liquid and its application
CN104084593A (en) * 2014-07-03 2014-10-08 北京工业大学 Method for extracting nano-silver in ionic liquid separation and enrichment liquid
CN107382675A (en) * 2017-08-08 2017-11-24 东莞理工学院 A kind of extracting process of hydroxytyrosol
CN107382675B (en) * 2017-08-08 2020-12-08 东莞理工学院 Method for extracting hydroxytyrosol
CN107399779A (en) * 2017-08-09 2017-11-28 北京盖雅环境科技有限公司 A kind of processing method of phenol wastewater

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