CN102040559A - Gemini dication based acid ionic liquid and preparation method thereof - Google Patents
Gemini dication based acid ionic liquid and preparation method thereof Download PDFInfo
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- CN102040559A CN102040559A CN2009102065508A CN200910206550A CN102040559A CN 102040559 A CN102040559 A CN 102040559A CN 2009102065508 A CN2009102065508 A CN 2009102065508A CN 200910206550 A CN200910206550 A CN 200910206550A CN 102040559 A CN102040559 A CN 102040559A
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Abstract
The invention discloses Gemini dication based acid ionic liquid and a preparation method thereof. The structure of a cation part of the ionic liquid is represented by a formula I, a formula II, a formula III or a formula IV, wherein in the formula I, the formula II, the formula III or the formula IV, m represents 3 or 4, and n represents an integral number of 1-15; and the structure of an anion part is selected from one of CH3(C6H4)SO<3->, C6H4COO<->, CF3SO<3->, CH3SO<3->, CH3COO<->, CF3COO<->, HSO<4->, BF<4->, PF<6->, H2PO<4->, NO<3-> and Cl<->. The preparation method comprises the following steps of: making Gemini bi-heterocyclic alkane react with alkyl sulfoacid inner ester to generate a sulfoacid inner salt; and then making the sulfoacid inner salt react with acid to obtain the ionic liquid. The ionic liquid can be used as a substitute of a traditional liquid acid catalyst and has industrial application prospect.
Description
Technical field
The present invention relates to a kind of acidic ion liquid based on the twin dication and preparation method thereof.
Background technology
(Ionic Liquids ILs), is to be made up of positively charged ion and negatively charged ion fully and in room temperature or be the salt system that melts of liquid when being bordering on room temperature to ionic liquid.Up to now, though, tend to that generally fusing point is lower than 100 ℃ salt and call ionic liquid at room temperature, be called fused salt and be higher than 100 ℃ salt to the not strict differentiation of ionic liquid at room temperature and fused salt.Ion liquid character makes it become the focus of research as non-volatile, wide liquid journey, strong electrostatic field, favorable conductive and wide electrochemical window, designability etc.Along with the continuous development of ionic liquid at room temperature research and application, ion liquid kind is increasing sharply.Ion liquid theoretically kind can only have hundreds of but up to the present study the ionic liquid at room temperature of reporting up to hundreds of millions kinds.Therefore ionic liquid is that the exploitation of kind or the field of studying all also have boundless space.
In recent years, increasing research focus focuses on the design preparation and the application facet of functionalized ion liquid, utilizes the principle of ionic liquid controllable structure, and its positively charged ion or negatively charged ion are carried out functional modification, can synthesize the ionic liquid with specific function.Ion liquid kind has not only greatly been enriched in the appearance of functionalized ion liquid, and has given its special physicochemical character.The acid functionalization ionic liquid is owing to have the high-density reaction active site of liquid acid catalyst, low volatility, and its structure and acidity has adjustable sex change, and the surrogate that is taken as the traditional industry acid catalyst is widely studied.
Summary of the invention
The object of the present invention is to provide a kind of acidic ion liquid based on the twin dication.
Another object of the present invention is to provide a kind of preparation method of the acidic ion liquid based on the twin dication.
The present invention's design synthesizes a kind of novel acidic ion liquid based on the twin dication, this ionic liquid has two single cation groups that separated by alkyl chain, with two single ion counter ion, have good thermostability and high strength of acid simultaneously, be expected to substitute the inorganic acid catalyst of traditional contaminate environment, have prospects for commercial application.
A kind of acidic ion liquid based on the twin dication, the structure of its cationic moiety is represented with formula I, formula II, formula III or formula IV:
Formula I is to formula IV, and m represents 3 or 4, and n represents the integer of 1-15; The structure of its anionicsite is selected from CH
3(C
6H
4) SO
3 -, C
6H
4COO
-, CF
3SO
3 -, CH
3SO
3 -, CH
3COO
-, CF
3COO
-, HSO
4 -, BF
4 -, PF
6 -, H
2PO
4 -, NO
3 -And Cl
-In a kind of.
The ionic liquid preparation is carried out in two steps:
The first step: two heterocycle alkane of twin and alkylsulphonic acid lactone reaction generate acid inner salt (Zwitterion salt);
Second step: acid inner salt and acid-respons obtain object ion liquid.
A kind of preparation method of the acidic ion liquid based on the twin dication is characterized in that this method steps is as follows:
A, with two heterocycle alkane, 1,3-propane sultone or 1, the 4-butane sultone, stirring and refluxing reaction is after 48-72 hour in reaction medium, resulting white solid washs with acetonitrile, carries out vacuum-drying then and obtains acid inner salt (Zwitterion salt); Described reaction medium is selected from acetonitrile, toluene or dehydrated alcohol;
B, acid inner salt and acid are placed reaction medium, at 70-90 ℃ of following stirring reaction 6-12 hour, product separated the acidic ion liquid that obtains based on the twin dication with ordinary method; Described reaction medium is selected from acetonitrile, toluene or dehydrated alcohol.
In the A step, the structure of two heterocycle alkane is represented with formula V, formula VI, formula VII or formula VIII:
Wherein n is the integer of 1-15.
In aforesaid method, the structure of acid inner salt is represented with formula IX, formula X, formula XI or formula XII:
Wherein m is 3 or 4, and n is the integer of 1-15.
In the A step, two heterocycle alkane and 1,3-propane sultone or 1, the mol ratio of 4-butane sultone is 1: 1.5-2.5.
In the B step, used acid is selected from a kind of in tosic acid, phenylformic acid, trifluoromethane sulfonic acid, methylsulphonic acid, acetate, trifluoroacetic acid, sulfuric acid, Tetrafluoroboric acid, phosphofluoric acid, phosphoric acid, nitric acid and the hydrochloric acid.
In the B step, acid inner salt is 1 with the mol ratio of acid: 1.5-2.5.
Ionic liquid of the present invention has following advantage:
1, the ionic liquid decomposition temperature is higher than 250 ℃, with single cationic ion liquid phase than having high thermostability;
2, ionic liquid and single cationic ion liquid phase are than having high strength of acid.
Ionic liquid of the present invention can be used as the substitute of traditional liquid acid catalyst, has prospects for commercial application.
Embodiment
Embodiment 1. synthesizes 1, two (N-propane sulfonic acid base imidazoles) the methane trifluoromethyl sulfonic acid ionic liquids of 1-
1) the stirring and refluxing reaction after 48 hours in acetonitrile of two heterocycle alkane 1 of 1mol, 1 of two imidazoles-methane of 1-and 2mol, 3-propane sultone, resulting white solid and are carried out vacuum-drying and are obtained acid inner salt with the acetonitrile washing for several times; (2) trifluoromethane sulfonic acid of 0.5mol acid inner salt and 1mol 80 ℃ of following stirring reactions 8 hours in toluene, the product that obtains washs for several times to remove the nonionic resistates with toluene and ether respectively, remove the laggard capable vacuum-drying of desolvating, make 1, two (N-propane sulfonic acid base imidazoles) the methane trifluoromethyl sulfonic acid ionic liquids of 1-are light yellow transparent liquid under the room temperature.Used two heterocycle alkane 1,1-is two, and imidazoles-the methane molecule structure is as follows:
Used acid inner salt molecular structure is as follows:
Embodiment 2. synthesizes 1, two (N-butane sulfonic group imidazoles) the methane tosilate ionic liquids of 1-
1) the stirring and refluxing reaction after 48 hours in acetonitrile of two heterocycle alkane 1 of 1mol, 1 of two imidazoles-methane of 1-and 2mol, 4-butane sultone, resulting white solid and are carried out vacuum-drying and are obtained acid inner salt with the acetonitrile washing for several times; (2) tosic acid of 0.5mol acid inner salt and 1mol 80 ℃ of following stirring reactions 6 hours in dehydrated alcohol, the product that obtains washs for several times to remove the nonionic resistates with toluene and ether respectively, remove the laggard capable vacuum-drying of desolvating, make 1, two (N-butane sulfonic group imidazoles) the methane tosilate ionic liquids of 1-are colourless transparent liquid under the room temperature.Used acid inner salt molecular structure is as follows:
Embodiment 3. synthesizes 1, two (N-butane sulfonic group imidazoles) the methane hydrosulfate ionic liquids of 1-
Press the acid inner salt 0.5mol of embodiment 2 preparations, with the 1mol vitriol oil 80 ℃ of following stirring reactions 10 hours in toluene, the product that obtains washs for several times to remove the nonionic resistates with toluene and ether respectively, remove the laggard capable vacuum-drying of desolvating, make 1, two (N-butane sulfonic group imidazoles) the methane hydrosulfate ionic liquids of 1-are light yellow transparent liquid under the room temperature.
Embodiment 4. synthesizes 1, two (N-butane sulfonic group imidazoles) the hexane trifluoromethyl sulfonic acid ionic liquids of 6-
1) the stirring and refluxing reaction after 72 hours in acetonitrile of two heterocycle alkane 1 of 1mol, 1 of two imidazoles-hexanes of 6-and 2mol, 4-butane sultone, resulting white solid and are carried out vacuum-drying and are obtained acid inner salt with the acetonitrile washing for several times; (2) trifluoromethane sulfonic acid of 0.5mol acid inner salt and 1mol 80 ℃ of following stirring reactions 12 hours in toluene, the product that obtains washs for several times to remove the nonionic resistates with toluene and ether respectively, remove the laggard capable vacuum-drying of desolvating, make 1, two (N-butane sulfonic group imidazoles) the hexane trifluoromethyl sulfonic acid ionic liquids of 6-are light yellow transparent liquid under the room temperature.Used two heterocycle alkane 1,6-is two, and imidazoles-the hexane molecular structure is as follows:
Used acid inner salt molecular structure is as follows:
Embodiment 5. synthesizes 1, two (N-butane sulfonic group imidazoles) the hexane tosilate ionic liquids of 6-
Press the acid inner salt 0.5mol of embodiment 4 preparations, with 1mol tosic acid 80 ℃ of following stirring reactions 10 hours in dehydrated alcohol, the product that obtains washs for several times to remove the nonionic resistates with toluene and ether respectively, remove the laggard capable vacuum-drying of desolvating, make 1, two (N-butane sulfonic group imidazoles) the hexane tosilate ionic liquids of 6-are light yellow transparent liquid under the room temperature.
Embodiment 6. synthesizes 1, two (N-butane sulfonic group imidazoles) the hexane benzoate ionic liquids of 6-
Press the acid inner salt 0.5mol of embodiment 4 preparations, with 1mol phenylformic acid 80 ℃ of following stirring reactions 10 hours in dehydrated alcohol, the product that obtains washs for several times to remove the nonionic resistates with toluene and ether respectively, remove the laggard capable vacuum-drying of desolvating, make 1, two (N-butane sulfonic group imidazoles) the hexane benzoate ionic liquids of 6-are light yellow transparent liquid under the room temperature.
Embodiment 7. synthesizes 1, two (N-butane sulfonic group imidazoles) the hexane metilsulfate ionic liquids of 6-
Press the acid inner salt 0.5mol of embodiment 4 preparations, with 1mol methylsulphonic acid 80 ℃ of following stirring reactions 10 hours in toluene, the product that obtains washs for several times to remove the nonionic resistates with toluene and ether respectively, remove the laggard capable vacuum-drying of desolvating, make 1, two (N-butane sulfonic group imidazoles) the hexane metilsulfate ionic liquids of 6-are light yellow transparent liquid under the room temperature.
Embodiment 8. synthesizes 1, two (N-butane sulfonic group imidazoles) the hexane acetic acid salt ion liquid of 6-
Press the acid inner salt 0.5mol of embodiment 4 preparations, with 1mol glacial acetic acid 80 ℃ of following stirring reactions 12 hours in dehydrated alcohol, the product that obtains washs for several times to remove the nonionic resistates with toluene and ether respectively, remove the laggard capable vacuum-drying of desolvating, make 1, two (N-butane sulfonic group imidazoles) the hexane acetic acid salt ion liquid of 6-are light yellow transparent liquid under the room temperature.
Embodiment 9. synthesizes 1, two (N-butane sulfonic group imidazoles) the hexane trifluoroacetate ionic liquids of 6-
Press the acid inner salt 0.5mol of embodiment 4 preparations, with 1mol trifluoroacetic acid 80 ℃ of following stirring reactions 12 hours in dehydrated alcohol, the product that obtains washs for several times to remove the nonionic resistates with toluene and ether respectively, remove the laggard capable vacuum-drying of desolvating, make 1, two (N-butane sulfonic group imidazoles) the hexane trifluoroacetate ionic liquids of 6-are light yellow transparent liquid under the room temperature.
Embodiment 10. synthesizes 1, two (N-butane sulfonic group imidazoles) the hexane tetrafluoroborate ion liquids of 6-
Press the acid inner salt 0.5mol of embodiment 4 preparations, with 1mol Tetrafluoroboric acid 80 ℃ of following stirring reactions 12 hours in toluene, the product that obtains washs for several times to remove the nonionic resistates with toluene and ether respectively, remove the laggard capable vacuum-drying of desolvating, make 1, two (N-butane sulfonic group imidazoles) the hexane tetrafluoroborate ion liquids of 6-are light yellow transparent liquid under the room temperature.
Embodiment 11. synthesizes 1, two (N-butane sulfonic group imidazoles) the hexane hexafluorophosphate ionic liquids of 6-
Press the acid inner salt 0.5mol of embodiment 4 preparations, with 1mol phosphofluoric acid 80 ℃ of following stirring reactions 12 hours in toluene, the product that obtains washs for several times to remove the nonionic resistates with toluene and ether respectively, remove the laggard capable vacuum-drying of desolvating, make 1, two (N-butane sulfonic group imidazoles) the hexane hexafluorophosphate ionic liquids of 6-are light yellow transparent liquid under the room temperature.
Embodiment 12. synthesizes 1, two (N-butane sulfonic group imidazoles) the hexane dihydrogen phosphate ionic liquids of 6-
Press the acid inner salt 0.5mol of embodiment 4 preparations, with 1mol phosphoric acid 80 ℃ of following stirring reactions 12 hours in toluene, the product that obtains washs for several times to remove the nonionic resistates with toluene and ether respectively, remove the laggard capable vacuum-drying of desolvating, make 1, two (N-butane sulfonic group imidazoles) the hexane dihydrogen phosphate ionic liquids of 6-are light yellow transparent liquid under the room temperature.
Embodiment 13. synthesizes 1, two (N-butane sulfonic group imidazoles) the hexane nitrate ion liquid of 6-
Press the acid inner salt 0.5mol of embodiment 4 preparations, with 1mol nitric acid 80 ℃ of following stirring reactions 12 hours in toluene, the product that obtains washs for several times to remove the nonionic resistates with toluene and ether respectively, remove the laggard capable vacuum-drying of desolvating, make 1, two (N-butane sulfonic group imidazoles) the hexane nitrate ion liquid of 6-are light yellow transparent liquid under the room temperature.
Embodiment 14. synthesizes 1, two (N-butane sulfonic group imidazoles) the hexane hydrochloride salt ion liquid of 6-
Press the acid inner salt 0.5mol of embodiment 4 preparations, with 1mol hydrochloric acid 80 ℃ of following stirring reactions 12 hours in toluene, the product that obtains washs for several times to remove the nonionic resistates with toluene and ether respectively, remove the laggard capable vacuum-drying of desolvating, make 1, two (N-butane sulfonic group imidazoles) the hexane hydrochloride salt ion liquid of 6-are light yellow transparent liquid under the room temperature.
Embodiment 15. synthesizes 1, two (N-butane sulfonic group imidazoles) the decane trifluoromethyl sulfonic acid ionic liquids of 10-
1) the stirring and refluxing reaction after 72 hours in acetonitrile of two heterocycle alkane 1 of 1mol, 1 of two imidazoles-decane of 10-and 2mol, 4-butane sultone, resulting white solid and are carried out vacuum-drying and are obtained acid inner salt with the acetonitrile washing for several times; (2) trifluoromethane sulfonic acid of 0.5mol acid inner salt and 1mol 80 ℃ of following stirring reactions 12 hours in toluene, the product that obtains washs for several times to remove the nonionic resistates with toluene and ether respectively, remove the laggard capable vacuum-drying of desolvating, make 1, two (N-butane sulfonic group imidazoles) the decane trifluoromethyl sulfonic acid ionic liquids of 10-are light yellow transparent liquid under the room temperature.Used two heterocycle alkane 1,10-is two, and imidazoles-the decane molecular structure is as follows:
Used acid inner salt molecular structure is as follows:
Embodiment 16. synthesizes 1, two (N-butane sulfonic group pyrroles) the hexane trifluoromethyl sulfonic acid ionic liquids of 6-
1) the stirring and refluxing reaction after 48 hours in acetonitrile of two heterocycle alkane 1 of 1mol, 1 of two pyrroles-hexanes of 6-and 2mol, 4-butane sultone, resulting white solid and are carried out vacuum-drying and are obtained acid inner salt with the acetonitrile washing for several times; (2) trifluoromethane sulfonic acid of 0.5mol acid inner salt and 1mol 80 ℃ of following stirring reactions 10 hours in toluene, the product that obtains washs for several times to remove the nonionic resistates with toluene and ether respectively, remove the laggard capable vacuum-drying of desolvating, make 1, two (N-butane sulfonic group pyrroles) the hexane trifluoromethyl sulfonic acid ionic liquids of 6-are light yellow transparent liquid under the room temperature.Used two heterocycle alkane 1,6-is two, and the pyrroles-the hexane molecular structure is as follows:
Used acid inner salt molecular structure is as follows:
Embodiment 17. synthesizes 1, two (N-butane sulfonic group pyrroles) the decane trifluoromethyl sulfonic acid ionic liquids of 10-
1) the stirring and refluxing reaction after 72 hours in acetonitrile of two heterocycle alkane 1 of 1mol, 1 of two pyrroles-decane of 10-and 2mol, 4-butane sultone, resulting white solid and are carried out vacuum-drying and are obtained acid inner salt with the acetonitrile washing for several times; (2) trifluoromethane sulfonic acid of 0.5mol acid inner salt and 1mol 80 ℃ of following stirring reactions 12 hours in toluene, the product that obtains washs for several times to remove the nonionic resistates with toluene and ether respectively, remove the laggard capable vacuum-drying of desolvating, make 1, two (N-butane sulfonic group pyrroles) the decane trifluoromethyl sulfonic acid ionic liquids of 10-are light yellow transparent liquid under the room temperature.Used two heterocycle alkane 1,10-is two, and the pyrroles-the decane molecular structure is as follows:
Used acid inner salt molecular structure is as follows:
Embodiment 18. synthesizes 1, two (N-butane sulfonic group morpholine) the hexane trifluoromethyl sulfonic acid ionic liquids of 6-
1) the stirring and refluxing reaction after 72 hours in acetonitrile of two heterocycle alkane 1 of 1mol, 1 of two morpholine-hexanes of 6-and 2mol, 4-butane sultone, resulting white solid and are carried out vacuum-drying and are obtained acid inner salt with the acetonitrile washing for several times; (2) trifluoromethane sulfonic acid of 0.5mol acid inner salt and 1mol 80 ℃ of following stirring reactions 12 hours in toluene, the product that obtains washs for several times to remove the nonionic resistates with toluene and ether respectively, remove the laggard capable vacuum-drying of desolvating, make 1, two (N-butane sulfonic group morpholine) the hexane trifluoromethyl sulfonic acid ionic liquids of 6-are light yellow transparent liquid under the room temperature.Used two heterocycle alkane 1,6-is two, and morpholine-the hexane molecular structure is as follows:
Used acid inner salt molecular structure is as follows:
Embodiment 19. synthesizes 1, two (N-butane sulfonic group piperidines) the hexane trifluoromethyl sulfonic acid ionic liquids of 6-
1) the stirring and refluxing reaction after 72 hours in acetonitrile of two heterocycle alkane 1 of 1mol, 1 of two piperidines-hexanes of 6-and 2mol, 4-butane sultone, resulting white solid and are carried out vacuum-drying and are obtained acid inner salt with the acetonitrile washing for several times; (2) trifluoromethane sulfonic acid of 0.5mol acid inner salt and 1mol 80 ℃ of following stirring reactions 12 hours in toluene, the product that obtains washs for several times to remove the nonionic resistates with toluene and ether respectively, remove the laggard capable vacuum-drying of desolvating, make 1, two (N-butane sulfonic group piperidines) the hexane trifluoromethyl sulfonic acid ionic liquids of 6-are light yellow transparent liquid under the room temperature.Used two heterocycle alkane 1,6-is two, and piperidines-the hexane molecular structure is as follows:
Used acid inner salt molecular structure is as follows:
Claims (7)
1. acidic ion liquid based on the twin dication, the structure of its cationic moiety is represented with formula I, formula II, formula III or formula IV:
Formula I is to formula IV, and m represents 3 or 4, and n represents the integer of 1-15; The structure of its anionicsite is selected from CH
3(C
6H
4) SO
3 -, C
6H
4COO
-, CF
3SO
3 -, CH
3SO
3 -, CH
3COO
-, CF
3COO
-, HSO
4 -, BF
4 -, PF
6 -, H
2PO
4 -, NO
3 -And Cl
-In a kind of.
2. according to claim 1 based on the preparation method of the acidic ion liquid of twin dication, it is characterized in that this method steps is as follows:
A, with two heterocycle alkane, 1,3-propane sultone or 1, the 4-butane sultone, stirring and refluxing reaction is after 48-72 hour in reaction medium, resulting white solid washs with acetonitrile, carries out vacuum-drying then and obtains acid inner salt; Described reaction medium is selected from acetonitrile, toluene or dehydrated alcohol;
B, acid inner salt and acid are placed reaction medium, at 70-90 ℃ of following stirring reaction 6-12 hour, product separated the acidic ion liquid that obtains based on the twin dication with ordinary method; Described reaction medium is selected from acetonitrile, toluene or dehydrated alcohol.
3. method as claimed in claim 2 is characterized in that: in the A step, the structure of two heterocycle alkane is represented with formula V, formula VI, formula VII or formula VIII:
Wherein n is the integer of 1-15.
4. method as claimed in claim 2 is characterized in that the structure of acid inner salt is represented with formula IX, formula X, formula XI or formula XII:
Wherein m is 3 or 4, and n is the integer of 1-15.
5. method as claimed in claim 2 is characterized in that: in the A step, and two heterocycle alkane and 1,3-propane sultone or 1, the mol ratio of 4-butane sultone is 1: 1.5-2.5.
6. method as claimed in claim 2, it is characterized in that: in the B step, used acid is selected from a kind of in tosic acid, phenylformic acid, trifluoromethane sulfonic acid, methylsulphonic acid, acetate, trifluoroacetic acid, sulfuric acid, Tetrafluoroboric acid, phosphofluoric acid, phosphoric acid, nitric acid and the hydrochloric acid.
7. method as claimed in claim 2 is characterized in that: in the B step, acid inner salt is 1 with the mol ratio of acid: 1.5-2.5.
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| CN102614913A (en) * | 2012-02-29 | 2012-08-01 | 昆明理工大学 | Imidazole high-acidity ionic liquid catalyst and application thereof |
| CN102614912A (en) * | 2012-02-29 | 2012-08-01 | 昆明理工大学 | Pyrazole strongly acidic ionic liquid catalyst and application thereof |
| CN103073372A (en) * | 2011-10-25 | 2013-05-01 | 中国科学院兰州化学物理研究所 | Method for synthesizing amine compound catalyzed by functionalized ionic liquid |
| CN105132187A (en) * | 2015-07-28 | 2015-12-09 | 辽宁石油化工大学 | Method for catalytic preparation of biodiesel by binuclear sulfonic-functionalized ionic liquid |
| CN108314610A (en) * | 2018-03-25 | 2018-07-24 | 王强 | A kind of method that catalysis prepares fenxizisu |
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2009
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103073372A (en) * | 2011-10-25 | 2013-05-01 | 中国科学院兰州化学物理研究所 | Method for synthesizing amine compound catalyzed by functionalized ionic liquid |
| CN103073372B (en) * | 2011-10-25 | 2016-03-02 | 中国科学院兰州化学物理研究所 | The method of functionalized ion liquid catalytically synthesizing aminated compounds |
| CN102614913A (en) * | 2012-02-29 | 2012-08-01 | 昆明理工大学 | Imidazole high-acidity ionic liquid catalyst and application thereof |
| CN102614912A (en) * | 2012-02-29 | 2012-08-01 | 昆明理工大学 | Pyrazole strongly acidic ionic liquid catalyst and application thereof |
| CN102614912B (en) * | 2012-02-29 | 2014-07-30 | 昆明理工大学 | Pyrazole strongly acidic ionic liquid catalyst and application thereof |
| CN105132187A (en) * | 2015-07-28 | 2015-12-09 | 辽宁石油化工大学 | Method for catalytic preparation of biodiesel by binuclear sulfonic-functionalized ionic liquid |
| CN108314610A (en) * | 2018-03-25 | 2018-07-24 | 王强 | A kind of method that catalysis prepares fenxizisu |
| CN108314610B (en) * | 2018-03-25 | 2021-10-08 | 佛山市安你心香精香料有限公司 | Method for preparing hyacinth by catalysis |
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Application publication date: 20110504 |