CN102503893A - Ionic liquid of alkyl imidazole metal oxysalt and preparation method thereof - Google Patents
Ionic liquid of alkyl imidazole metal oxysalt and preparation method thereof Download PDFInfo
- Publication number
- CN102503893A CN102503893A CN2011103475901A CN201110347590A CN102503893A CN 102503893 A CN102503893 A CN 102503893A CN 2011103475901 A CN2011103475901 A CN 2011103475901A CN 201110347590 A CN201110347590 A CN 201110347590A CN 102503893 A CN102503893 A CN 102503893A
- Authority
- CN
- China
- Prior art keywords
- ion
- ionic liquid
- liquid
- alkyl
- alkyl imidazole
- 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.)
- Pending
Links
Images
Abstract
The invention discloses ionic liquid of alkyl imidazole metal oxysalt and a preparation method thereof, the ionic liquid is prepared by using alkyl imidazole ion as cation and oxometallic acid radical as anion, and performing an ion double decomposition exchange reaction on the chloridized or bromized alkyl imidazole and the metal oxysalt. The preparation method thereof comprises the steps of: dissolving silver tungstate Ag2WO4, silver molybdate Ag2MoO4, silver chromate Ag2CrO4 or sodium dichromate Na2Cr2O7 and the ionic liquid of chloridized or bromized alkyl imidazole in 100 times by mass of deionized water according to a mass ratio of 1:2, reacting for 3-8 h, filtering to remove silver chloride or silver bromide precipitate or separating liquid to remove sodium chloride, rotary evaporating and vacuum drying to remove the moisture to obtain the corresponding ionic liquid of alkyl imidazole and metal oxysalt. The ionic liquid disclosed by the invention is used as a substitute of metal oxysalt, and the ionic liquid can be used as a reactant, a solvent, a template agent or a precursor of a transition metal oxide in the reaction, so that the ionic liquid has a large potential function and an extensive application prospect in such fields as inorganic nanometer material preparation and catalytic oxidation, etc.
Description
Technical field
The present invention relates to organic synthesis and field of inorganic material preparing technology, especially a kind of alkyl imidazole metal oxygen-containing hydrochlorate ionic liquid and preparation method.
Background technology
Ionic liquid be meant fully by bigger organic cation of volume and the less inorganic anion of volume combine under room temperature or low temperature, generally be lower than 100 ℃, the ionic compound that is in a liquid state.Ionic liquid has the temperature range that is in a liquid state is big, soluble end is wide, electrochemical window is wide, good thermostability, " zero " vapour pressure, advantage such as easy to use; Be eco-friendly green solvent; Be suitable for the requirement of current cleaning technique of advocating and Sustainable development, more and more by the extensive recognition and acceptance of people.Ionic liquid has experienced three developmental stage through years of development: water sensitive system (before the 90's of last century), water-fast system (the 90's of last century are to the beginning of this century), functionalization system (this century).Functionalized ion liquid is meant in forming ion liquid positively charged ion or negatively charged ion and contains specific functional group, has one type of ionic liquid of special physico-chemical property.Ion liquid functionalization is divided into: (1) cationic functionalization, main sulfo group functionalization, amino functional, acid amides functionalization, hydroxyl functionalization, ester group functionalization, cyanic acid functionalization and chirality functionization; (2) anionic functionalization comprises fluorochemical anionoid, Lewis acids negatively charged ion, sulfonic acid and sulfuric acid ester negatively charged ion and coordination anion.Along with deepening continuously of ionic liquid theory and application technical research, more and more stronger to ion liquid demand novel, that have specific function.Realize ion liquid functionalization to satisfy specific demand,, advance process of industrialization that very important meaning is arranged the scope of extension ion liquid in practical application.
Summary of the invention
The purpose of this invention is to provide a kind of alkyl imidazole metal oxygen-containing hydrochlorate ionic liquid and preparation method, this ionic liquid has huge potential function and wide application prospect at organic catalysis oxidation and inorganic nano material aspect preparing.
The objective of the invention is to realize like this:
A kind of alkyl imidazole metal oxygen-containing hydrochlorate ionic liquid, it is characterized in that this ionic liquid be with the alkyl imidazole ion be positively charged ion, with containing metal oxygen acid group as negatively charged ion, get through the preparation of ion metathesis exchange reaction by chlorination or bromination alkyl imidazole and metal oxygen-containing hydrochlorate; Wherein: the alkyl imidazole ion is 1-ethyl-3-NSC 158165 ion [Emim]
+, 1-methyl-3-NSC 158165 ion [Bmim]
+, 1-methyl-3-hexyl imidazol ion [Hmim]
+, 1-methyl-3-octyl group imidazol ion [Omim]
+Or 1-methyl-3-decyl imidazol ion [Dmim]
+Said containing metal oxygen acid group is wolframate radical [WO
4]
2-, molybdic acid is with [MoO
4]
2-, chromate [CrO
4]
2-Or dichromate ion [Cr
2O
7]
2-
Above-mentioned preparation method of ionic liquid comprises following concrete steps:
With wolframic acid silver Ag
2WO
4, silver molybdate Ag
2MoO
4Or silver chromate Ag
2CrO
4Be dissolved in the deionized water of 100 times of amount of substances in 1: 2 ratio of amount of substance with chlorination or bromination alkyl imidazo ion liquid; Reacted 3～8 hours; Remove by filter Silver monochloride or Silver monobromide deposition; Revolve steaming through 50～70 ℃, moisture is removed in 60～80 ℃ of vacuum-dryings, obtains corresponding alkyl imidazole metal oxygen-containing hydrochlorate ionic liquid; Wherein: the alkyl carbon chain length of chlorination or bromination alkyl imidazo ion liquid is C
2n, n=1～4;
Perhaps
With sodium dichromate 99 Na
2Cr
2O
7Be dissolved in the deionized water of 100 amount of substances in 1: 2 ratio of amount of substance with chlorination or bromination alkyl imidazo ion liquid; Reacted 3～8 hours; Separatory is obtained layer oily matter; Take off layer oily matter through 50～70 ℃ of vacuum-dryings after repeatedly washing separatory, remove moisture, obtain corresponding alkyl imidazole metal oxygen-containing hydrochlorate ionic liquid; Wherein: the alkyl carbon chain length of chlorination or bromination alkyl imidazo ion liquid is C
2n, n=3～5.
Compared with prior art, the present invention has following remarkable advantage:
⑴, developed the new kind of functionalized ion liquid;
⑵, utilize the IX replacement(metathesis)reaction, processing ease, equipment is simple, is suitable for scale operation;
⑶, prepared ionic liquid, the alternative article as the metal oxygen-containing hydrochlorate in reaction, can be used as reactant, solvent, masterplate agent;
⑷, prepared ionic liquid, as the presoma of transition metal oxide, in inorganic nano material preparation, and there are huge function of potential and wide application prospect in field such as catalyzed oxidation.
Description of drawings
The ion liquid infared spectrum that Fig. 1 makes for the embodiment of the invention 4;
The ion liquid nuclear magnetic spectrum that Fig. 2 makes for the embodiment of the invention 4;
The ion liquid infared spectrum that Fig. 3 makes for the embodiment of the invention 8;
The ion liquid nuclear magnetic spectrum that Fig. 4 makes for the embodiment of the invention 8;
The ion liquid infared spectrum that Fig. 5 makes for the embodiment of the invention 16;
The ion liquid nuclear magnetic spectrum that Fig. 6 makes for the embodiment of the invention 16.
Embodiment
[Emim]
2[WO
4] preparation
With 0.05mol Ag
2WO
4Place the 90ml deionized water, stir 30min, add 0.1mol [Emim] Cl then, continue reaction 4h, remove by filter the AgCl deposition.With the liquid of gained, 70 ℃ revolve steaming, and 80 ℃ of vacuum-drying 12h obtain ionic liquid [Emim]
2[WO
4].
[Bmim]
2[WO
4] preparation
With 0.05mol Ag
2WO
4Place the 90ml deionized water, stir 30min, add 0.1mol [Bmim] Cl then, continue reaction 6h, remove by filter the AgCl deposition.With the liquid of gained, 70 ℃ revolve steaming, and 80 ℃ of vacuum-drying 12h obtain ionic liquid [Bmim]
2[WO
4].
Embodiment 3
[Hmim]
2[WO
4] preparation
With 0.05mol Ag
2WO
4Place the 90ml deionized water, stir 30min, add 0.1mol [Hmim] Br then, continue reaction 5h, remove by filter the AgBr deposition.With the liquid of gained, 60 ℃ revolve steaming, and 70 ℃ of vacuum-drying 12h obtain ionic liquid [Hmim]
2[WO
4].
[Omim]
2[WO
4] preparation
With 0.05mol Ag
2WO
4Place the 90ml deionized water, stir 30min, add 0.1mol [Omim] Br then, continue reaction 6h, remove by filter the AgBr deposition.With the liquid of gained, 50 ℃ revolve steaming, and 60 ℃ of vacuum-drying 12h obtain ionic liquid [Omim]
2[WO
4].
Consult Fig. 1,3369 cm
-1That corresponding is H
2Among the O-and the stretching vibration of OH, explain that ionic liquid contains a spot of water.The vibrational band of positively charged ion characteristic group: at ionic liquid [Omim]
2[WO
4] in, 3151 cm
-1About key band be that stretching vibration by C-H on the imidazole ring causes; 2967 cm
-1, 2864 cm
-1With 1384 cm
-1Key band belong to the antisymmetric stretching vibration of C-H, symmetrical stretching vibration and flexural vibration on the methylene radical on the imidazole ring respectively; 1167 cm
-1, 1006 cm
-1Key band ownership be the flexural vibration of imidazoles H-C-C; 712 cm
-1, 620 cm
-1Key band ownership be the flexural vibration of imidazoles C-N-C.The vibrational band of negatively charged ion characteristic group: 826 cm
-1The stretching vibration bands of a spectrum of corresponding W-O.
Consult Fig. 2, owing to do not contain Wasserstoffatoms in the ionic liquid negatively charged ion, so all hydrogen spectrum signals all derive from glyoxaline cation, concrete shift value signal ownership is listed in the table below:
Positively charged ion imidazoles ring hydrogen is because deshielding effect all appears at low, and the hydrogen that is connected on first carbon of alkyl substituent on the imidazole ring appears at low slightly position, and the hydrogen on other carbon of alkyl substituent appears at High-Field.Prove and contain N-methyl and two substituent imidazole ring structures of N-alkyl in the ion liquid positively charged ion.
[Omim]
2[WO
4] ultimate analysis
With determination of elemental analysis C, H, N content, and measured the content of W with ICP.Can know that by last diagram data experiment test value and theoretical value are very approaching, explain that the content of various elements in the synthetic product is described consistent with molecular formula.
[Omim]
2[WO
4] solvability
Institute's synthetic ionic liquid [Omim]
2[WO
4] except that being insoluble to ether, toluene, can be dissolved in common most of solvents, have good solubility.
[Emim]
2[MoO
4] preparation
With 0.05mol Ag
2MoO
4Place the 90ml deionized water, stir 30min, add 0.1mol [Emim] Cl then, continue reaction 4h, remove by filter the AgCl deposition.With the liquid of gained, 70 ℃ revolve steaming, and 80 ℃ of vacuum-drying 12h obtain ionic liquid [Emim]
2[MoO
4].
Embodiment 6
[Bmim]
2[MoO
4] preparation
With 0.05mol Ag
2MoO
4Place the 90ml deionized water, stir 30min, add 0.1mol [Bmim] Br then, continue reaction 4h, remove by filter the AgBr deposition.With the liquid of gained, 70 ℃ revolve steaming, and 80 ℃ of vacuum-drying 12h obtain ionic liquid [Bmim]
2[MoO
4].
[Hmim]
2[MoO
4] preparation
With 0.05mol Ag
2MoO
4Place the 90ml deionized water, stir 30min, add 0.1mol [Hmim] Br then, continue reaction 5h, remove by filter the AgBr deposition.With the liquid of gained, 60 ℃ revolve steaming, and 70 ℃ of vacuum-drying 12h obtain ionic liquid [Hmim]
2[MoO
4].
Embodiment 8
[Omim]
2[MoO
4] preparation
With 0.05mol Ag
2MoO
4Place the 90ml deionized water, stir 30min, add 0.1mol [Omim] Br then, continue reaction 6h, remove by filter the AgBr deposition.With the liquid of gained, 50 ℃ revolve steaming, and 60 ℃ of vacuum-drying 12h obtain ionic liquid [Omim]
2[MoO
4].
Consult Fig. 3,3400 cm
-1That corresponding is H
2Among the O-and the stretching vibration of OH, explain that ionic liquid contains a spot of water.The vibrational band of positively charged ion characteristic group: in containing the ionic liquid of glyoxaline cation, 3139 cm
-1Key band be that stretching vibration by C-H on the imidazole ring causes; 2927,2856 and 1384 cm
-1Key band belong to the antisymmetric stretching vibration of C-H, symmetrical stretching vibration and flexural vibration on the methylene radical on the imidazole ring respectively; 1167 cm
-1About key band ownership be the flexural vibration of imidazoles H-C-C; 759 cm
-1, 621 cm
-1Key band ownership be the flexural vibration of imidazoles C-N-C.The vibrational band of negatively charged ion characteristic group: 825 cm
-1The stretching vibration bands of a spectrum of corresponding Mo-O.
Consult Fig. 4, owing to do not contain Wasserstoffatoms in the ionic liquid negatively charged ion, so all hydrogen spectrum signals all derive from glyoxaline cation, concrete shift value signal ownership is listed in the table below:
Positively charged ion imidazoles ring hydrogen is because deshielding effect all appears at low, and the hydrogen that is connected on first carbon of alkyl substituent on the imidazole ring appears at low slightly position, and the hydrogen on other carbon of alkyl substituent appears at High-Field.Prove and contain N-methyl and two substituent imidazole ring structures of N-alkyl in the ion liquid positively charged ion.
[Omim]
2[MoO
4] ultimate analysis
With determination of elemental analysis C, H, N content, and measured the content of Mo with ICP.Can know that by last diagram data experiment test value and theoretical value are very approaching, explain that the content of various elements in the synthetic product is described consistent with molecular formula.
[Omim]
2[MoO
4] solvability
Ionic liquid [Omim]
2[MoO
4] except that water insoluble, ether, toluene, can be dissolved in most of common solvents, have good solubility.
Embodiment 9
[Emim]
2[CrO
4] preparation
With 0.05mol Ag
2CrO
4Place the 90ml deionized water, stir 30min, add 0.1mol [Emim] Cl then, continue reaction 4h, remove by filter the AgCl deposition.With the liquid of gained, 70 ℃ revolve steaming, and 80 ℃ of vacuum-drying 12h obtain ionic liquid [Emim]
2[CrO
4].
[Bmim]
2[CrO
4] preparation
With 0.05mol Ag
2CrO
4Place the 90ml deionized water, stir 30min, add 0.1mol [Bmim] Cl then, continue reaction 6h, remove by filter the AgCl deposition.With the liquid of gained, 70 ℃ revolve steaming, and 80 ℃ of vacuum-drying 12h obtain ionic liquid [Bmim]
2[CrO
4].
Embodiment 11
[Hmim]
2[CrO
4] preparation
With 0.05mol Ag
2CrO
4Place the 90ml deionized water, stir 30min, add 0.1mol [Hmim] Br then, continue reaction 5h, remove by filter the AgBr deposition.With the liquid of gained, 60 ℃ revolve steaming, and 70 ℃ of vacuum-drying 12h obtain ionic liquid [Hmim]
2[CrO
4].
Embodiment 12
[Omim]
2[CrO
4] preparation
With 0.05mol Ag
2CrO
4Place the 90ml deionized water, stir 30min, add 0.1mol [Omim] Br then, continue reaction 6h, remove by filter the AgBr deposition.With the liquid of gained, 50 ℃ revolve steaming, and 60 ℃ of vacuum-drying 12h obtain ionic liquid [Omim]
2[CrO
4].
Embodiment 13
[Hmim]
2[Cr
2O
7] preparation
With 0.05mol Na
2Cr
2O
7Place the 90ml deionized water, stir 30min, add 0.1mol [Hmim] Cl then, continue reaction 8h, separatory takes off a layer oily matter, takes off a layer oily matter after repeatedly washing separatory, and 80 ℃ of vacuum-drying 12h obtain ionic liquid [Hmim]
2[Cr
2O
7].
Embodiment 14
[Omim]
2[Cr
2O
7] preparation
With 0.05mol Na
2Cr
2O
7Place the 90ml deionized water, stir 30min, add 0.1mol [Omim] Cl then, continue reaction 8h, separatory takes off a layer oily matter, takes off a layer oily matter after repeatedly washing separatory, and 70 ℃ of vacuum-drying 12h obtain ionic liquid [Omim]
2[Cr
2O
7]
Embodiment 15
[Dmim]
2[Cr
2O
7] preparation
With 0.05mol Na
2Cr
2O
7Place the 90ml deionized water, stir 30min, add 0.1mol [Dmim] Br then, continue reaction 3h, separatory takes off a layer oily matter, takes off a layer oily matter after repeatedly washing separatory, and 60 ℃ of vacuum-drying 12h obtain ionic liquid [Dmim]
2[Cr
2O
7].
Embodiment 16
[Omim]
2[Cr
2O
7] preparation
With 0.05mol Na
2Cr
2O
7Place the 90ml deionized water, stir 30min, add 0.1mol [Omim] Br then, continue reaction 6h, separatory takes off a layer oily matter, takes off a layer oily matter after repeatedly washing separatory, and 50 ℃ of vacuum-drying 12h obtain ionic liquid [Omim]
2[Cr
2O
7].
Consult Fig. 5,3418 cm
-1That corresponding is H
2Among the O-and the stretching vibration of OH, explain that ionic liquid contains a spot of water.The vibrational band of positively charged ion characteristic group: in containing the ionic liquid of glyoxaline cation, 3139 cm
-1Key band be that stretching vibration by C-H on the imidazole ring causes; 2960,2856 and 1384 cm
-1About key band belong to the antisymmetric stretching vibration of C-H, symmetrical stretching vibration and flexural vibration on the methylene radical on the imidazole ring respectively; 1167 cm
-1About key band ownership be the flexural vibration of imidazoles H-C-C; 763 cm
-1, 622 cm
-1Key band ownership be the flexural vibration of imidazoles C-N-C.The vibrational band of negatively charged ion characteristic group: 947 cm
-1The stretching vibration bands of a spectrum of corresponding Cr-O.
Consult Fig. 6, owing to do not contain Wasserstoffatoms in the ionic liquid negatively charged ion, so all hydrogen spectrum signals all derive from glyoxaline cation, concrete shift value signal ownership is listed in the table below:
Positively charged ion imidazoles ring hydrogen is because deshielding effect all appears at low, and the hydrogen that is connected on first carbon of alkyl substituent on the imidazole ring appears at low slightly position, and the hydrogen on other carbon of alkyl substituent appears at High-Field.Prove and contain N-methyl and two substituent imidazole ring structures of N-alkyl in the ion liquid positively charged ion.
[Omim]
2[Cr
2O
7] ultimate analysis
With determination of elemental analysis C, H, N content, and measured the content of Cr with ICP.Can know that by last diagram data experiment test value and theoretical value are very approaching, explain that the content of various elements in the synthetic product is described consistent with molecular formula.
[Omim]
2[Cr
2O
7] solvability
Institute's synthetic ionic liquid [Omim]
2[Cr
2O
7] except that water insoluble, ether, toluene, can be dissolved in common most of solvents, have good solubility.
Claims (2)
1. alkyl imidazole metal oxygen-containing hydrochlorate ionic liquid, it is characterized in that this ionic liquid be with the alkyl imidazole ion be positively charged ion, with containing metal oxygen acid group as negatively charged ion, get through the preparation of ion metathesis exchange reaction by chlorination or bromination alkyl imidazole and metal oxygen-containing hydrochlorate; Wherein: the alkyl imidazole ion is 1-ethyl-3-NSC 158165 ion [Emim]
+, 1-methyl-3-NSC 158165 ion [Bmim]
+, 1-methyl-3-hexyl imidazol ion [Hmim]
+, 1-methyl-3-octyl group imidazol ion [Omim]
+Or 1-methyl-3-decyl imidazol ion [Dmim]
+Said containing metal oxygen acid group is wolframate radical [WO
4]
2-, molybdic acid is with [MoO
4]
2-, chromate [CrO
4]
2-Or dichromate ion [Cr
2O
7]
2-
2. said preparation method of ionic liquid of claim 1 is characterized in that this method comprises following concrete steps:
With wolframic acid silver Ag
2WO
4, silver molybdate Ag
2MoO
4Or silver chromate Ag
2CrO
4Be dissolved in the deionized water of 100 times of amount of substances in 1: 2 ratio of amount of substance with chlorination or bromination alkyl imidazo ion liquid; Reacted 3～8 hours; Remove by filter Silver monochloride or Silver monobromide deposition; Revolve steaming through 50～70 ℃, moisture is removed in 60～80 ℃ of vacuum-dryings, obtains corresponding alkyl imidazole metal oxygen-containing hydrochlorate ionic liquid; Wherein: the alkyl carbon chain length of chlorination or bromination alkyl imidazo ion liquid does
C 2n , n=1～4;
Perhaps
With sodium dichromate 99 Na
2Cr
2O
7Be dissolved in the deionized water of 100 times of amount of substances in 1: 2 ratio of amount of substance with chlorination or bromination alkyl imidazo ion liquid; Reacted 3～8 hours; Separatory is obtained layer oily matter; Take off layer oily matter through 50～80 ℃ of vacuum-dryings after repeatedly washing separatory, remove moisture, obtain corresponding alkyl imidazole metal oxygen-containing hydrochlorate ionic liquid; Wherein: the alkyl carbon chain length of chlorination or bromination alkyl imidazo ion liquid does
C 2n , n=3～5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011103475901A CN102503893A (en) | 2011-11-07 | 2011-11-07 | Ionic liquid of alkyl imidazole metal oxysalt and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011103475901A CN102503893A (en) | 2011-11-07 | 2011-11-07 | Ionic liquid of alkyl imidazole metal oxysalt and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102503893A true CN102503893A (en) | 2012-06-20 |
Family
ID=46216042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011103475901A Pending CN102503893A (en) | 2011-11-07 | 2011-11-07 | Ionic liquid of alkyl imidazole metal oxysalt and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102503893A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103977839A (en) * | 2014-06-05 | 2014-08-13 | 江南大学 | Ionic organic metal tungstate epoxidation catalyst and preparation method thereof |
| CN104232244A (en) * | 2013-06-07 | 2014-12-24 | 中国石油化工股份有限公司 | Application of imidazole ionic liquid in lubricating oil additive |
| CN105439856A (en) * | 2015-11-04 | 2016-03-30 | 江西师范大学 | Method for preparing didodecyl carbonate by taking oxometallate ion liquid as catalyst |
| CN107740078A (en) * | 2017-11-01 | 2018-02-27 | 合肥工业大学 | Magnesium lithium alloy ionic liquid chemical conversion solution and the method for forming conductive oxide film |
| CN111333582A (en) * | 2020-04-08 | 2020-06-26 | 辽宁大学 | Imidazolyl organic molybdenum ionic liquid and preparation method thereof |
| CN111349047A (en) * | 2020-03-03 | 2020-06-30 | 扬州大学 | Carbon paste ion selective electrode and preparation method and application thereof |
| CN111454551A (en) * | 2020-04-08 | 2020-07-28 | 辽宁大学 | Application of imidazolyl molybdate ionic liquid in preparation of P LL A/I L s blend |
| CN112916041A (en) * | 2021-01-29 | 2021-06-08 | 福州大学化肥催化剂国家工程研究中心 | Oil-soluble molybdenum-based ionic liquid catalyst and preparation method and application thereof |
| CN114832854A (en) * | 2021-02-01 | 2022-08-02 | 中国科学院化学研究所 | Tungstate ionic liquid, preparation method thereof and application of tungstate ionic liquid in catalytic oxidation degradation of phenol and derivatives thereof in wastewater |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2378701A (en) * | 2001-07-04 | 2003-02-19 | Shell Int Research | Process for the preparation of alkylene glycols |
| CN101851215A (en) * | 2010-01-22 | 2010-10-06 | 西安近代化学研究所 | Method for catalyzing and synthesizing 3,4-dinitrofurazan by utilizing1-butyl-3-methylimidazole tungstate |
-
2011
- 2011-11-07 CN CN2011103475901A patent/CN102503893A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2378701A (en) * | 2001-07-04 | 2003-02-19 | Shell Int Research | Process for the preparation of alkylene glycols |
| CN101851215A (en) * | 2010-01-22 | 2010-10-06 | 西安近代化学研究所 | Method for catalyzing and synthesizing 3,4-dinitrofurazan by utilizing1-butyl-3-methylimidazole tungstate |
Non-Patent Citations (1)
| Title |
|---|
| YUNXIANG QIAO ET AL.: "Physicochemical Properties of Tungstate-Based Room-Temperature Ionic Liquids", 《JOURNAL OF THE ELECTROCHEMICAL SOCIETY》 * |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104232244B (en) * | 2013-06-07 | 2016-12-28 | 中国石油化工股份有限公司 | The application in lube oil additive of a kind of glyoxaline ion liquid |
| CN104232244A (en) * | 2013-06-07 | 2014-12-24 | 中国石油化工股份有限公司 | Application of imidazole ionic liquid in lubricating oil additive |
| CN103977839B (en) * | 2014-06-05 | 2016-03-30 | 江南大学 | A kind of ionic organic metal tungstates epoxidation catalyst and preparation method thereof |
| CN103977839A (en) * | 2014-06-05 | 2014-08-13 | 江南大学 | Ionic organic metal tungstate epoxidation catalyst and preparation method thereof |
| CN105439856B (en) * | 2015-11-04 | 2019-02-19 | 江西师范大学 | A method of using oxometallic acid ionic liquid as catalyst preparation didodecyl carbonate |
| CN105439856A (en) * | 2015-11-04 | 2016-03-30 | 江西师范大学 | Method for preparing didodecyl carbonate by taking oxometallate ion liquid as catalyst |
| CN107740078A (en) * | 2017-11-01 | 2018-02-27 | 合肥工业大学 | Magnesium lithium alloy ionic liquid chemical conversion solution and the method for forming conductive oxide film |
| CN111349047A (en) * | 2020-03-03 | 2020-06-30 | 扬州大学 | Carbon paste ion selective electrode and preparation method and application thereof |
| CN111349047B (en) * | 2020-03-03 | 2022-06-14 | 扬州大学 | Carbon paste ion selective electrode and preparation method and application thereof |
| CN111333582A (en) * | 2020-04-08 | 2020-06-26 | 辽宁大学 | Imidazolyl organic molybdenum ionic liquid and preparation method thereof |
| CN111454551A (en) * | 2020-04-08 | 2020-07-28 | 辽宁大学 | Application of imidazolyl molybdate ionic liquid in preparation of P LL A/I L s blend |
| CN112916041A (en) * | 2021-01-29 | 2021-06-08 | 福州大学化肥催化剂国家工程研究中心 | Oil-soluble molybdenum-based ionic liquid catalyst and preparation method and application thereof |
| CN112916041B (en) * | 2021-01-29 | 2023-08-04 | 福州大学化肥催化剂国家工程研究中心 | Oil-soluble molybdenum-based ionic liquid catalyst and preparation method and application thereof |
| CN114832854A (en) * | 2021-02-01 | 2022-08-02 | 中国科学院化学研究所 | Tungstate ionic liquid, preparation method thereof and application of tungstate ionic liquid in catalytic oxidation degradation of phenol and derivatives thereof in wastewater |
| CN114832854B (en) * | 2021-02-01 | 2023-04-28 | 中国科学院化学研究所 | Tungstic acid radical ionic liquid, preparation method thereof and application of tungstic acid radical ionic liquid in catalytic oxidative degradation of phenol and derivatives thereof in wastewater |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102503893A (en) | Ionic liquid of alkyl imidazole metal oxysalt and preparation method thereof | |
| Liu et al. | Multi-functional fluorescent responses of cobalt complexes derived from functionalized amide-bridged ligand | |
| Bai et al. | BiOBrxI1− x/BiOBr heterostructure engineering for efficient molecular oxygen activation | |
| Ilhan et al. | Synthesis, structural characterization and electrochemical studies of new macrocyclic Schiff base containing pyridine head and its metal complexes | |
| US9067957B2 (en) | Metal nickel-imidazolate chiral nano clathrate complex and preparation method thereof | |
| Kumar et al. | Synthesis of CuO and Cu 2 O nano/microparticles from a single precursor: Effect of temperature on CuO/Cu 2 O formation and morphology dependent nitroarene reduction | |
| Zhang et al. | Anderson-type polyoxometalate-based complexes constructed from a new ‘V’-like bis-pyridine–bis-amide ligand for selective adsorption of organic dyes and detection of Cr (VI) and Fe (III) ions | |
| Pang et al. | An active metal-organic anion framework with highly exposed SO42− on {001} facets for the enhanced electrochemical detection of trace Fe3+ | |
| Milja et al. | Synthesis, characterization and application of uranyl ion imprinted polymers of aniline and 8-hydroxy quinoline functionalized aniline | |
| Yang et al. | Ba-MOFs with tetrazole-based acetic acids: unusual configuration, novel topology and high proton conductivity | |
| Xu et al. | Fabrication of ZIF-8 based on lignin with high yield for dye removal from water | |
| Chen et al. | Constructing redox-active 3D covalent organic frameworks with high-affinity hexameric binding sites for enhanced uranium capture | |
| Liu et al. | Conductive MOFs for electrocatalysis and electrochemical sensor | |
| CN104829813B (en) | A kind of ionomeric polymer containing phosphine, preparation method and anion-exchange membrane | |
| Dube et al. | Structure and properties of an eight-coordinate Mn (ii) complex that demonstrates a high water relaxivity | |
| Zhao et al. | Microporous Cd-MOF as multifunctional material for rapid and visual luminescence sensing of Fe3+, MnO4− and TNP in water and efficient CO2 catalytic conversion | |
| CN108559097B (en) | 3,3',5,5' -azoxybenzenetetracarboxylic acid europium (III) metal coordination polymer and synthetic method and application thereof | |
| CN111807970A (en) | Method for preparing N-benzylaniline by catalytic oxidation of aniline with polyoxometallate | |
| CN104341456B (en) | (R, R)-1,2-diphenyl ethylene diamine nitrine nickel complex and preparation method thereof | |
| Lawrence et al. | Synthesis, X-ray crystallographic, electrochemical, and spectroscopic studies of Bis-(1, 10-phenanthroline)(2, 2′-bipyridine) cobalt (III) Hexafluorophosphate | |
| CN105481025A (en) | Porous cobalt hydroxide material, and preparation method and applications thereof | |
| Qiao et al. | Physicochemical properties of tungstate-based room-temperature ionic liquids | |
| Lee et al. | Facile fabrication of flower-like Ni-Co-Mn based LDHs and their superior catalytic performance for atenolol, nitrite and methanol | |
| Tunçel et al. | Synthesis, characterization, and histological activity of novel polydentate azo ligands and their cobalt (II), copper (II) and nickel (II) complexes | |
| Doss et al. | High-pressure temperature-jump evidence for an Ia mechanism for substitution reactions of manganese (II) in aqueous solution |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20120620 |