CN1869024A - 1-amido-3-alkyl imidozole ionic liquid and its preparation method - Google Patents

1-amido-3-alkyl imidozole ionic liquid and its preparation method Download PDF

Info

Publication number
CN1869024A
CN1869024A CN 200610035576 CN200610035576A CN1869024A CN 1869024 A CN1869024 A CN 1869024A CN 200610035576 CN200610035576 CN 200610035576 CN 200610035576 A CN200610035576 A CN 200610035576A CN 1869024 A CN1869024 A CN 1869024A
Authority
CN
China
Prior art keywords
amide group
liquid
alkyl
ionic liquid
ion liquid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN 200610035576
Other languages
Chinese (zh)
Other versions
CN1869024B (en
Inventor
李雪辉
张磊
王芙蓉
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
South China University of Technology SCUT
Original Assignee
South China University of Technology SCUT
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by South China University of Technology SCUT filed Critical South China University of Technology SCUT
Priority to CN200610035576A priority Critical patent/CN1869024B/en
Publication of CN1869024A publication Critical patent/CN1869024A/en
Application granted granted Critical
Publication of CN1869024B publication Critical patent/CN1869024B/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Abstract

A 1-amido-3-alkylimidazole ion liquid is prepared through reaction between 1-alkylimidazole and haloester to obtain 1-ester-3-alkylimidazole halide ion liquid, ammonolyzing reaction to obtain 1-amido-3-alkylimidazole halide ion liquid, and ion exchange.

Description

1-amide group-3-alkyl imidazo ion liquid and preparation method thereof
Technical field
The present invention relates to a kind of novel ionic liquid, specifically refer to a kind of novel 1-amide group-3-alkyl imidazo ion liquid and preparation method thereof, belong to new chemical material and preparing technical field thereof.
Background technology
Ionic liquid is subjected to the extensive concern of domestic and international academia and industry member as a kind of green solvent and environment-friendly catalyst, becomes the forward position and the research focus of chemistry in the present age.Western countries and each big chemical company have dropped into great amount of manpower and material resources and have developed research, " ionic liquid " have been decided to be the novel process that promotes and transform existing " Coal Chemical Industry ", the important Chemicals of exploitation as South Africa SASOL company; NATO group big area is invested and is developed ionic liquid etc.Ionic liquid is by an organic cation and a compounds inorganic or that organic anion is formed, have unique character: the electrochemical window of adjustable Lewis acidity, good electrical conductivity, broad, non-volatile, the solvent ability is strong etc., has been widely used in every field such as electrochemistry, organic synthesis, separation, analysis, life science, functional materials and clean energy.
In recent years, continue to bring out with the various new function ionic liquids that contain functional group that " cutting " has special or single-minded purposes by original ionic liquid being carried out molecular designing: Chinese invention patent CN1635063 has synthesized the glyoxaline ion liquid that a kind of substituted alkyl contains phosphonic acid ester functional group; Chinese invention patent CN1385243A has synthesized diacetone acrylic amide type ionic liquid; Chinese invention patent CN1594280 has synthesized pyridine-sulfonic acid salt ion liquid; CN1583726 has synthesized chirality alkyl tetrafluoroborate ionic liquid etc.But do not see bibliographical information for functionalized ion liquid of introducing amide group in the glyoxaline cation in the present invention and preparation method thereof.
Summary of the invention
The object of the present invention is to provide a kind of novel 1-amide group-3-alkyl imidazo ion liquid that can be used as the Lewis alkaline catalysts.
Another object of the present invention is to provide the preparation method of 1-amide group-3-alkyl imidazo ion liquid.
Purpose of the present invention can be achieved through the following technical solutions:
A kind of 1-amide group-3-alkyl imidazo ion liquid has following chemical structure of general formula:
Figure A20061003557600051
Wherein n is 1～10, and y is 0～19 integer, X -Negatively charged ion for following structure: Cl -, Br -, I -, BF 4 -, PF 6 -, CF 3COO -, CF 3SO 3 -, CF 3OSO 3 -, C (CF 3SO 2) 3 -, CH 3OSO 3 -, ClSO 3 -, C 6H 5SO 3 -, N (CF 3SO 2) 2 -, SbF 6 -, SCN -, HSO 4 -, HCO 3 -, H 2PO 4 -, NO 3 -, C mH 2m+1COO -Or C mH 2m+1SO 3 -(m is 1～10 natural number).
The preparation method of described 1-amide group-3-alkyl imidazo ion liquid: 0.010mol 1-ester group-3-alkyl imidazole halide ions liquid is dissolved in 100ml～200ml dehydrated alcohol, feed the exsiccant ammonia, stirring reaction 3h～5h at room temperature, there is precipitation to separate out, stopped reaction filters, and uses the absolute ethanol washing post precipitation, to precipitate vacuum-drying 1h～3h, obtain 1-amide group-3-alkyl imidazole halide ions liquid; The ester group of described 1-ester group-3-alkyl imidazole halide ions liquid has following structure:
Wherein a is 1～16, and y is 0～19 integer.
The another kind of preparation method of described 1-amide group-3-alkyl imidazo ion liquid: 1-amide group-3-alkyl imidazole halide ions liquid is mixed with the dichloromethane solution that contains anionic sodium salt or sylvite, the mol ratio of 1-amide group-3-alkyl imidazole halide ions liquid and anionic sodium salt or sylvite is 1: 1, stirring reaction 4h～6h, solution is filtered, use the washed with dichloromethane post precipitation, to precipitate dry and solvent will be steamed, can obtain serial 1-amide group-3-alkyl imidazo ion liquid; Described negatively charged ion is BF 4 -, PF 6 -, CF 3COO -, CF 3SO 3 -, CF 3OSO 3 -, C (CF 3SO 2) 3 -, CH 3OSO 3 -, ClSO 3 -, C 6H 5SO 3 -, N (CF 3SO 2) 2 -, SbF 6 -, SCN -, HSO 4 -, HCO 3 -, H 2PO 4 -, NO 3 -, C mH 2m+1COO -Or C mH 2m+1SO 3 -(m is 1～10 natural number).
1-amide group provided by the invention-3-alkyl imidazo ion liquid and technology of preparing thereof have following characteristics:
1,1-amide group provided by the present invention-3-alkyl imidazo ion liquid is a kind of novel ion liquid, by preparation method of the present invention with amide group substituted imidazole ionic liquid N-ester group, improve ion liquid polarity of original ester group and physical and chemical performances such as the solvability that has changed it, fusing point greatly, developed the ionic liquid new variety.
2, ionic liquid provided by the invention can be used as the Lewis alkaline catalysts;
3, of the present invention preparation is simple, and reaction is fast, and the productive rate height just can reach very high purity through simple purification, and suitable large-scale industrial production.
Embodiment
The present invention is further illustrated below in conjunction with embodiment, but the scope of protection of present invention is not limited to the scope that embodiment expresses.
Synthesizing of embodiment 1:1-formamido--3-Methylimidazole chloride ion liquid
1-methyl-formiate base-3-Methylimidazole chloride ion liquid 0.010mol is dissolved in the 100ml dehydrated alcohol, feed the exsiccant ammonia, stirring reaction 3h at room temperature, there is precipitation to separate out, stopped reaction filters, and uses the absolute ethanol washing post precipitation, to precipitate vacuum-drying 2h, obtain 1-formamido--3-Methylimidazole chloride ion liquid 0.0082mol.Reaction equation is:
Figure A20061003557600071
Embodiment 2:1-acetamido-3-decyl imidazolium bromide is ion liquid synthetic
1-octyl acetate base-3-decyl imidazolium bromide ionic liquid 0.010mol is dissolved in the 200ml dehydrated alcohol, feeds the exsiccant ammonia, at room temperature stirring reaction 4h has precipitation to separate out.Stopped reaction filters, and uses the absolute ethanol washing post precipitation, will precipitate vacuum-drying 1h, obtains 1-acetamido-3-decyl imidazolium bromide ionic liquid 0.0081mol.Reaction equation is:
Embodiment 3:1-20 amide group-3-decyl imidazolium chloride is ion liquid synthetic
1-20 sour hexadecyl ester bases-3-decyl imidazolium chloride ionic liquid 0.010mol is dissolved in the 100ml dehydrated alcohol, feeds the exsiccant ammonia, at room temperature stirring reaction 5h has precipitation to separate out.Stopped reaction filters, and uses the absolute ethanol washing post precipitation, will precipitate vacuum-drying 3h, obtains 1-20 amide group-3-decyl imidazolium chloride ionic liquid 0.0080mol.Reaction equation is:
Embodiment 4:1-caprinoyl amido-3-amyl group imidazolium bromide is ion liquid synthetic
1-n-decyl decylate base-3-amyl group imidazolium bromide ionic liquid 0.010mol is dissolved in the 150ml dehydrated alcohol, feeds the exsiccant ammonia, at room temperature stirring reaction 3h has precipitation to separate out.Stopped reaction filters, and uses the absolute ethanol washing post precipitation, will precipitate vacuum-drying 2h, obtains 1-caprinoyl amido-3-amyl group imidazolium bromide ionic liquid 0.0079mol.Reaction equation is:
Embodiment 5:1-formamido--3-Methylimidazole hexafluorophosphate is ion liquid synthetic
Getting among the embodiment 1 0.1 mole of the 1-formamido-of preparation-3-Methylimidazole chloride ion liquid mixes with the methylene dichloride that contains 0.1 mole of sodium hexafluoro phosphate, stirring reaction 5h, solution is filtered, use the washed with dichloromethane post precipitation, to precipitate dry and solvent will be steamed, obtain 1-formamido--3-Methylimidazole hexafluorophosphate ionic liquid 0.092mol.
Embodiment 6:1-acetamido-3-decyl imidazole nitrate is ion liquid synthetic
Getting among the embodiment 2 0.1 mole of the 1-acetamido of preparation-3-decyl imidazolium bromide ionic liquid mixes with the methylene dichloride that contains 0.1 mole of SODIUMNITRATE, stirring reaction 4h, solution is filtered, use the washed with dichloromethane post precipitation, to precipitate dry and solvent will be steamed, obtain 1-acetamido-3-decyl imidazole nitrate ionic liquid 0.093mol.
Embodiment 7:1-20 amide group-3-decyl tetrafluoroborate is ion liquid synthetic
Getting among the embodiment 3 0.1 mole of 1-20 amide group of preparation-3-decyl imidazolium chloride ionic liquid mixes with the methylene dichloride that contains 0.1 mole of sodium tetrafluoroborate, stirring reaction 6h, solution is filtered, use the washed with dichloromethane post precipitation, to precipitate dry and solvent will be steamed, obtain 1-20 amide group-3-decyl tetrafluoroborate ionic liquid 0.091mol.
Embodiment 8:1-caprinoyl amido-3-amyl group imidazoles fluoroform sulphonate is ion liquid synthetic
Getting among the embodiment 4 0.1 mole of the 1-caprinoyl amido of preparation-3-amyl group imidazolium bromide ionic liquid mixes with the methylene dichloride that contains 0.1 mole of trifluoromethanesulfonic acid potassium, stirring reaction 5h, solution is filtered, use the washed with dichloromethane post precipitation, to precipitate dry and solvent will be steamed, obtain 1-caprinoyl amido-3-amyl group imidazoles fluoroform sulphonate ionic liquid 0.096mol.
Embodiment 9:1-formamido--3-Methylimidazole formate is ion liquid synthetic
Getting among the embodiment 1 0.1 mole of the 1-formamido-of preparation-3-Methylimidazole chloride ion liquid mixes with the methylene dichloride that contains 0.1 mole of potassium formiate, stirring reaction 6h, solution is filtered, use the washed with dichloromethane post precipitation, to precipitate dry and solvent will be steamed, obtain 1-formamido--3-Methylimidazole formate ionic liquid 0.090mol.
Embodiment 10:1-acetamido-3-decyl imidazoles valerate is ion liquid synthetic
Getting among the embodiment 2 methylene dichloride that 0.1 mole of the 1-acetamido of preparation-3-decyl imidazole ion liquid and natrium valericum contain 0.1 mole mixes, stirring reaction 5h, solution is filtered, use the washed with dichloromethane post precipitation, to precipitate dry and solvent will be steamed, obtain 1-acetamido-3-decyl imidazoles valerate ionic liquid 0.093mol.
Embodiment 11:1-20 amide group-3-decyl imidazoles caprate is ion liquid synthetic
Getting among the embodiment 3 0.1 mole of 1-20 amide group of preparation-3-decyl imidazolium chloride ionic liquid mixes with the methylene dichloride that contains 0.1 mole of Sodium decanoic acid, stirring reaction 4h, solution is filtered, use the washed with dichloromethane post precipitation, to precipitate dry and solvent will be steamed, obtain 1-20 amide group-3-decyl imidazoles caprate ionic liquid 0.092mol.
Synthesizing of embodiment 12:1-caprinoyl amido-3-amyl group imidazoles thiocyanate ion liquid
Getting among the embodiment 4 0.1 mole of the 1-caprinoyl amido of preparation-3-amyl group imidazolium bromide ionic liquid mixes with the methylene dichloride that contains 0.1 molar sulphur Zassol, stirring reaction 4h, solution is filtered, use the washed with dichloromethane post precipitation, to precipitate dry and solvent will be steamed, reaction obtains 1-caprinoyl amido-3-amyl group imidazoles thiocyanate ion liquid 0.091mol.
Synthesizing of embodiment 13:1-formamido--3-Methylimidazole sulfonate ion in last of the ten Heavenly stems liquid
Getting among the embodiment 1 0.1 mole of the 1-formamido-of preparation-3-Methylimidazole chloride ion liquid mixes with the methylene dichloride that contains 0.1 mole of sodium decylsulfonate, stirring reaction 6h, solution is filtered, use the washed with dichloromethane post precipitation, to precipitate dry and solvent will be steamed, obtain 1-formamido--3-Methylimidazole sulfonate ion in last of the ten Heavenly stems liquid 0.087mol.
Embodiment 14:1-acetamido-3-decyl imidazoles chlorsulfonic acid hydrochlorate is ion liquid synthetic
Getting among the embodiment 2 0.1 mole of the 1-acetamido of preparation-3-decyl imidazolium bromide ionic liquid mixes with the methylene dichloride that contains 0.1 mole of chlorsulfonic acid sodium, stirring reaction 5h, solution is filtered, use the washed with dichloromethane post precipitation, to precipitate dry and solvent will be steamed, obtain 1-acetamido-3-decyl imidazoles chlorosulfonate ionic liquid 0.089mol.
Embodiment 15:1-20 amide group-3-decyl imidazoles mesylate is ion liquid synthetic
Getting among the embodiment 3 0.1 mole of 1-20 amide group of preparation-3-decyl imidazolium chloride ionic liquid mixes with the methylene dichloride that contains 0.1 mole of methanesulfonic sodium, stirring reaction 4h, solution is filtered, use the washed with dichloromethane post precipitation, to precipitate dry and solvent will be steamed, obtain 1-20 amide group-3-decyl imidazoles mesylate ionic liquid 0.091mol.
Embodiment 16:1-caprinoyl amido-3-amyl group imidazoles benzene sulfonate is ion liquid synthetic
Getting among the embodiment 4 0.1 mole of the 1-caprinoyl amido of preparation-3-amyl group imidazolium bromide ionic liquid mixes with the methylene dichloride that contains 0.1 mole of benzene sulfonic acid sodium salt, stirring reaction 5h, solution is filtered, use the washed with dichloromethane post precipitation, to precipitate dry and solvent will be steamed, obtain 1-caprinoyl amido-3-amyl group imidazoles benzene sulfonate ionic liquid 0.090mol.
Synthesizing of embodiment 17:1-formamido--3-Methylimidazole bicarbonate ion liquid
Getting among the embodiment 1 0.1 mole of the 1-formamido-of preparation-3-Methylimidazole chloride ion liquid mixes with the methylene dichloride that contains 0.1 mole of sodium bicarbonate, stirring reaction 4h, solution is filtered, use the washed with dichloromethane post precipitation, to precipitate dry and solvent will be steamed, obtain 1-formamido--3-Methylimidazole bicarbonate ion liquid 0.091mol.
Embodiment 18:1-acetamido-3-decyl imidazole bisulfate is ion liquid synthetic
Getting among the embodiment 2 0.1 mole of the 1-acetamido of preparation-3-decyl imidazolium bromide ionic liquid mixes with the methylene dichloride that contains 0.1 mol sulfuric acid hydrogen sodium, stirring reaction 6h, solution is filtered, use the washed with dichloromethane post precipitation, to precipitate dry and solvent will be steamed, obtain 1-acetamido-3-decyl imidazole bisulfate ionic liquid, productive rate is 0.093mol.
Embodiment 19:1-20 amide group-3-decyl imidazoles hydrophosphate is ion liquid synthetic
Getting among the embodiment 3 0.1 mole of 1-20 amide group of preparation-3-decyl imidazolium chloride ionic liquid mixes with the methylene dichloride that contains 0.1 mole of phosphoric acid hydrogen potassium, stirring reaction 5h, solution is filtered, use the washed with dichloromethane post precipitation, to precipitate dry and solvent will be steamed, obtain 1-20 amide group-3-decyl imidazoles hydrophosphate ionic liquid 0.092mol.
Application Example: 1-acetamido-3-Methylimidazole muriate is applied in the base catalyzed reactions
At vinyl cyanide, 1-acetamido-3-Methylimidazole muriate and CCl 4(1.0: 0.07: 0.8 mol ratios) feeding mol ratio is 1.1 Cl in the system 2Carry out the chlorination addition reaction of vinyl cyanide, 5 ℃ of temperature of reaction, reaction times 5h, after reaction finished, underpressure distillation obtained 2, and 3-two chloroethyl nitriles, the transformation efficiency of vinyl cyanide are 97.28%, 2, and the yield of 3-two chloroethyl nitriles is 95.57%.Use ionic liquid as green solvent and eco-friendly catalyzer in this reaction system, ionic liquid reclaims easily, and is reusable more than 10 times, still has good catalytic activity.Traditional 2, use the disagreeableness catalyst systems of environment such as dimethyl formamide, phosphoric acid salt, alkaline carbonate, salt of wormwood and polyvinyl pyridine in the 3-two chloroethyl nitrile addition reactions, though 2, the yield of 3-two chloroethyl nitriles can reach more than 90%, but exists catalyzer to stack difficulty, be difficult to reclaim and problem such as poisonous.

Claims (3)

1, a kind of 1-amide group-3-alkyl imidazo ion liquid is characterized in that having following chemical structure of general formula:
Figure A2006100355760002C1
Wherein n is 1～10, and y is 0～19 integer, X -Negatively charged ion for following structure: Cl -, Br -, I -, BF 4 -, PF 6 -, CF 3COO -, CF 3SO 3 -, CF 3OSO 3 -, C (CF 3SO 2) 3 -, CH 3OSO 3 -, ClSO 3 -, C 6H 5SO 3 -, N (CF 3SO 2) 2 -, SbF 6 -, SCN -, HSO 4 -, HCO 3 -, H 2PO 4 -, NO 3 -, C mH2 M+1COO -Or C mH 2m+1SO 3 -(m is 1～10 natural number).
2, the method for preparing the described 1-amide group of claim 1-3-alkyl imidazo ion liquid, it is characterized in that: 0.010mol 1-ester group-3-alkyl imidazole halide ions liquid is dissolved in 100ml～200ml dehydrated alcohol, feed the exsiccant ammonia, at room temperature stirring reaction 3h～5h has precipitation to separate out stopped reaction, filter, use the absolute ethanol washing post precipitation, will precipitate vacuum-drying 1h～3h, obtain 1-amide group-3-alkyl imidazole halide ions liquid; The ester group of described 1-ester group-3-alkyl imidazole halide ions liquid has following structure:
Figure A2006100355760002C2
Wherein a is 1～16, and y is 0～19 integer.
3, the method for preparing the described 1-amide group of claim 1-3-alkyl imidazo ion liquid, it is characterized in that: 1-amide group-3-alkyl imidazole halide ions liquid is mixed with the dichloromethane solution that contains anionic sodium salt or sylvite, the mol ratio of 1-amide group-3-alkyl imidazole halide ions liquid and anionic sodium salt or sylvite is 1: 1, stirring reaction 4h～6h, solution is filtered, use the washed with dichloromethane post precipitation, to precipitate dry and solvent will be steamed, can obtain serial 1-amide group-3-alkyl imidazo ion liquid; Described negatively charged ion is BF 4 -, PF 6 -, CF 3COO -, CF 3SO 3 -, CF 3OSO 3 -, C (CF 3SO 2) 3 -, CH 3OSO 3 -, ClSO 3 -, C 6H 5SO 3 -, N (CF 3SO 2) 2 -, SbF 6 -, SCN -, HSO 4 -, HCO 3 -, H 2PO 4 -, NO 3 -, C mH 2m+1COO -Or C mH 2m+1SO 3 -(m is 1～10 natural number).
CN200610035576A 2006-05-23 2006-05-23 1-amido-3-alkyl imidozole ionic liquid and its preparation method Expired - Fee Related CN1869024B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN200610035576A CN1869024B (en) 2006-05-23 2006-05-23 1-amido-3-alkyl imidozole ionic liquid and its preparation method

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN200610035576A CN1869024B (en) 2006-05-23 2006-05-23 1-amido-3-alkyl imidozole ionic liquid and its preparation method

Publications (2)

Publication Number Publication Date
CN1869024A true CN1869024A (en) 2006-11-29
CN1869024B CN1869024B (en) 2010-05-12

Family

ID=37442822

Family Applications (1)

Application Number Title Priority Date Filing Date
CN200610035576A Expired - Fee Related CN1869024B (en) 2006-05-23 2006-05-23 1-amido-3-alkyl imidozole ionic liquid and its preparation method

Country Status (1)

Country Link
CN (1) CN1869024B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101993418B (en) * 2009-08-21 2013-08-07 北京师范大学 (Methyl) acrylamido carboxylate ionic liquid and preparation method thereof
CN109985611A (en) * 2019-04-28 2019-07-09 中国科学院兰州化学物理研究所 A kind of catalyst and preparation method thereof, a kind of preparation method of N- alkyl imidazole compound
CN113933431A (en) * 2021-10-22 2022-01-14 中国烟草总公司郑州烟草研究院 Method for measuring alkaloid in cigarette mainstream smoke

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100486968C (en) * 2005-10-25 2009-05-13 河北科技大学 Imidazole type functional ion liquid having N-substituted amide structure fragment, and its preparation method

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101993418B (en) * 2009-08-21 2013-08-07 北京师范大学 (Methyl) acrylamido carboxylate ionic liquid and preparation method thereof
CN109985611A (en) * 2019-04-28 2019-07-09 中国科学院兰州化学物理研究所 A kind of catalyst and preparation method thereof, a kind of preparation method of N- alkyl imidazole compound
CN113933431A (en) * 2021-10-22 2022-01-14 中国烟草总公司郑州烟草研究院 Method for measuring alkaloid in cigarette mainstream smoke
CN113933431B (en) * 2021-10-22 2023-09-01 中国烟草总公司郑州烟草研究院 Method for determining alkaloid in main stream smoke of cigarettes

Also Published As

Publication number Publication date
CN1869024B (en) 2010-05-12

Similar Documents

Publication Publication Date Title
CN1090600C (en) Process for producing alkylene glycol
CN1948268A (en) Synthesis method of quaternary ammonium salt
CN108084120A (en) It is used to prepare difunctional solid catalyst of soda acid of 5 hydroxymethyl furfural and its preparation method and application
CN101050205A (en) Compound containing cation radical of piperazidine, synthetic method, and application
CN101058552A (en) Double-functional group ionic liquid and preparation method
CN105543886A (en) Electrochemical catalytic synthesis method of aromaticnitrile
CN106854195A (en) A kind of preparation method of fluoro ethylene carbonate with high purity
CN104292114A (en) Preparation method of onium hydroxide
CN1869024A (en) 1-amido-3-alkyl imidozole ionic liquid and its preparation method
CN110512224A (en) A kind of method that electrochemistry oxygen metaplasia nitrogen simultaneously restores fixed nitrogen ammonification simultaneously
CN1306959A (en) Prep. of sulfuryl imine compound
CN1903419A (en) Polyoxyethylene chain three cation quaternary ammonium salt type surfactant and its sysnthesis method
CN102716767B (en) Preparation method of high-acid-content carbon-based solid acid
CN110407724A (en) A kind of double ion is to ionic liquid and preparation method thereof
CN1850802A (en) N-amido pyridine ion liquid, and its preparing method
CN1891807A (en) Guerbet anion surfactant, and its preparing method and use
CN101050196A (en) Bronsted acidic compound of containing L- proline radical, preparation method, and application
CN100532359C (en) Method of synthesizing ion liquid at room temperature
CN102408339B (en) Clean nitration reaction of aromatic hydrocarbon of heteropolyacid pyridinium ionic liquid catalyst
CN102069010B (en) Montmorillonite catalyst used in preparation of cyclic carbonate
CN1148338C (en) Fluorine-containing trifluorostyrene monomer and its synthesis and use
CN101560187A (en) Binary eutectic ionic liquid and preparation method thereof
CN110204731B (en) Nano phosphazene microsphere containing ionic liquid and preparation method and application thereof
CN1931856A (en) Crown ether condensed thiosemicarbazide as anion recognizing receptor and its prepn and application
CN103274977A (en) Preparation method of thiocarbamate compound

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20100512

Termination date: 20150523

EXPY Termination of patent right or utility model