CN109825848A - N, N- dialkyl pyrrolidinium bromide ionic liquid preparation method and applications - Google Patents

N, N- dialkyl pyrrolidinium bromide ionic liquid preparation method and applications Download PDF

Info

Publication number
CN109825848A
CN109825848A CN201910197327.5A CN201910197327A CN109825848A CN 109825848 A CN109825848 A CN 109825848A CN 201910197327 A CN201910197327 A CN 201910197327A CN 109825848 A CN109825848 A CN 109825848A
Authority
CN
China
Prior art keywords
ionic liquid
bromide ionic
preparation
cathode
dialkyl pyrrolidinium
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
CN201910197327.5A
Other languages
Chinese (zh)
Other versions
CN109825848B (en
Inventor
俸颢
梁望
石晓遂
李克
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.)
Shenzhen Million Technology Co Ltd
Original Assignee
Shenzhen Million Technology Co Ltd
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 Shenzhen Million Technology Co Ltd filed Critical Shenzhen Million Technology Co Ltd
Priority to CN201910197327.5A priority Critical patent/CN109825848B/en
Publication of CN109825848A publication Critical patent/CN109825848A/en
Application granted granted Critical
Publication of CN109825848B publication Critical patent/CN109825848B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Landscapes

  • Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)

Abstract

The present invention relates to a kind of N, N- dialkyl pyrrolidinium bromide ionic liquid preparation method and applications, this method is realized using N- alkyl tetrahydro pyrroles and alkylol as raw material by electrolysis mode, is provided with cation-exchange membrane in a cell, electrolytic cell is divided into cathode chamber and anode chamber by cation-exchange membrane, catholyte is taken out after completing electrolysis, isolates and purifies, obtains N, N- dialkyl pyrrolidinium class bromide ionic liquid, the preparation method simple process, mild condition, purity and yield are higher.By N, N- dialkyl pyrrolidinium bromide ionic liquid is as solvent, using the hydrochloride of chloromethylpyridine and ammonium hydroxide as raw material, three picolyl aminated compounds are synthesized, the preparation method yield and purity is high are not necessarily to later separation, it is at low cost, environmentally protective, ionic liquid can be repeatedly circulated, and be suitable for industrialized production.

Description

N, N- dialkyl pyrrolidinium bromide ionic liquid preparation method and applications
Technical field
The present invention relates to a kind of preparation method and applications of pyrrolidines bromide ionic liquid, specifically a kind of N, N- bis- Alkyl pyrrolidine class bromide ionic liquid.
Background technique
Ionic liquid (ionic liquid) is a kind of room temperature being made of organic cation and organic or inorganic anion Fuse salt, have wide liquid journey, low-steam pressure, heat and chemical stability are high, physicochemical property is adjustable, electrochemical window mouth width, well from The special natures such as subconductivity, environmental-friendly.Ionic liquid is widely used to chemical industry as green solvent, functional material, urges The numerous areas such as change, energy environment, life science also show the potential and outlook developed in other application field.
In recent years, ionic liquid due to its liquid temperature it is wide, stability is high simultaneously non-combustible;Solvability is adjusted to nothing by force The dissolubility of machine object, organic matter or polymer, and volatility is extremely low, viscosity is big and fusing point is low;Become to make it have The primary condition of function admirable lubricant, and become the hot subject of lubricant research field.
The synthetic method of conventional ion liquid is usually that halogenated hydrocarbons and reactive tertiary amine is used to generate quaternary ammonium halide, due to halogen Higher for hydrocarbon reaction activity, often there is need largely to be difficult to remove using organic solvent, foreign ion, be produced into for this method The disadvantages of this is higher, seriously constrains the large-scale production of ionic liquid.Therefore, find it is a kind of quick, efficiently prepare ionic liquid The method of body has very important practical significance, will push the industrialization process of ionic liquid significantly.
Since cell construction and diaphragm material are continuously improved, the especially development and utilization of amberplex, significantly The yield of current efficiency and ionic liquid is improved, cell efficiency increases substantially, therefore prepares ion using electrolysis tech The method of liquid has also obtained more and more concerns, especially because electrolysis method prepare ionic liquid with mild condition, at Originally the incomparable advantage of other process routes such as lower, environmentally protective, it has also become the hot spot that various countries competitively develop.
Due to being not that any kind of ionic liquid may be suitable for what electrolytic method produced, how further The ionic liquid type for expanding electrolysis method preparation is the current ultimate challenge that we are faced.
Summary of the invention
Based on presently, there are the problem of, the invention proposes a kind of N, the systems of N- dialkyl pyrrolidinium class bromide ionic liquid Preparation Method, preparation is simple, and mild condition, purity and yield are higher, is suitble to large-scale industrial production.
N, N- dialkyl pyrrolidinium class bromide ionic liquid such as formula (I)
Wherein R1, R2 can be identical or different, are selected from C1-20 linear or branched alkyl group, preferably C1-6 alkyl, such as first Base, ethyl, propyl, isopropyl, butyl, isobutyl group, tert-butyl, amyl, isopentyl, neopentyl, hexyl, 2- hexyl etc.
The preparation method of N proposed by the present invention, N- dialkyl pyrrolidinium class bromide ionic liquid, with N- alkyl tetrahydro pyrroles It is raw material by electrolysis mode realization with alkylol, is provided with cation-exchange membrane in a cell, then by cell reaction For ion exchange to generate N, N- dialkyl pyrrolidinium class bromide ionic liquid, electrolytic cell is divided into cathode chamber by cation-exchange membrane With anode chamber, using PtO2For anode, graphite is cathode, and electrolytic cell sun is added in the glycol water that concentration is 5-8mol/L It is used as anolyte in pole room, the acetonitrile water mixed solution for the KBr that content is 2-5wt% is added in electric tank cathode room and is made It is room temperature to 50 DEG C in electrolysis temperature for catholyte, current density 1-3A/dm2Under conditions of constant-current electrolysis 0.5- 2h takes out catholyte after completing electrolysis, isolates and purifies, obtain N, N- dialkyl pyrrolidinium class bromide ionic liquid.
Wherein R1 and R2 such as formula (I) is defined.
In preparation method of the present invention, R2As raw material betatopic in the anode compartment then nucleophilic occurs for OH alkylol Reaction generates pyrrolidines quaternary ammonium cation, and in electric field action, pyrrolidines quaternary ammonium cation passes through cation-exchange membrane, in cathode chamber N, N- dialkyl pyrrolidinium class bromide ionic liquid are generated with Br ions binding.
Preferably, cation-exchange membrane is Nafion cation-exchange membrane, preferably 902 cation-exchange membrane of Nafion.
Preferably, by filled respectively in two reservoirs concentration be 5-8mol/L glycol water as anode Replenisher, content are the acetonitrile water mixed solution of the KBr of 2-5wt% as cathode replenisher, and pass through two circulating pump difference By electrolyzer anode chamber and a reservoir, electric tank cathode room is connected to another reservoir, and two circulating pumps respectively will be positive Pole electrolyte and catholyte are constantly swapped with anode replenisher and cathode replenisher so that electrolyzer anode chamber and Anolyte and catholyte in cathode chamber keep stable concentration.
Preferably, complete first to obtain extract liquor with xylene extraction after electrolysis takes out catholyte, then with water, be saturated Sodium bicarbonate aqueous solution, water are successively washed, and anhydrous magnesium sulfate is dry, and concentration obtains the N, N- dialkyl pyrrolidinium class Bromide ionic liquid.
The present invention also provides N, N- dialkyl pyrrolidinium class bromide ionic liquid is used to synthesize the purposes of three picolyl amine. Three picolyl amine are widely used in the preparation of synthesizing bionic catalyst as a kind of important chemical intermediate.Three picolyls Amine iron complex can simulate the function of toluene monoxidase, apply to the oxidative degradation of aromatic ring and the epoxidation of the compound containing ethylene linkage The preparation of product.It is newest research shows that three picolyl amine are greater than normal cell to the recognition capability of tumour cell becomes and develop New targeting antitumoral compounds.The synthesis of three picolyl amine is generally original with bipyridine methyl amine and chloromethylpyridine Expect, is reacted 24 hours under room temperature, purifying products need silica gel column chromatography, and yield is only 60-70%.The method reaction time is long, Raw material bipyridine methyl amine value lattice are higher, and purification process, using a large amount of volatile organic solvents, cost high pollution is big.Therefore The green tripyridyl methyl amine synthetic method being simple and efficient is studied, is of great significance and value.
The present invention is with N, and N- dialkyl pyrrolidinium class bromide ionic liquid is solvent, with the hydrochloride and ammonia of chloromethylpyridine Water is raw material, synthesizes three picolyl aminated compounds, the preparation method yield and purity is high, is not necessarily to later separation, at low cost, Environmentally protective, ionic liquid can be repeatedly circulated, and be suitable for industrialized production.
Wherein: one of X1, X2 and X3 are N atom.
Specific reaction step is as follows:
By the hydrochloride and N of chloromethylpyridine, N- dialkyl pyrrolidinium class bromide ionic liquid mixes in reactor, control Then ammonium hydroxide is slowly added dropwise at 40-70 DEG C in system under stiring, after detecting the fully reacting of raw material chloromethylpyridine stop that ammonia is added dropwise Then water is stirred for 1 hour, stop reaction, be down to room temperature, is slowly added to deionized water, Precipitation, filtering, precipitating use Na2CO3Solution, ethanol washing, dry product.
It is preferred that ammonium hydroxide is the ammonium hydroxide that mass percent concentration is 30%;
It is preferred that Na2CO3Solution is the Na that mass percent concentration is 5%2CO3Solution.
Specific embodiment
Embodiments of the present invention are described in detail by the following examples, however, the present invention is not limited thereto.
Embodiment 1
It is equipped with three layers of 902 cation-exchange membrane of Nafion in a cell, electrolytic cell is divided into cathode by cation-exchange membrane Room and anode chamber, using PtO2For anode, graphite is cathode, and electrolytic cell sun is added in the glycol water that concentration is 5mol/L It is used as anolyte in pole room, 10gN- methyl nafoxidine and 7g normal propyl alcohol are added in anode chamber.It is by content The acetonitrile mixed aqueous solution of the KBr of 3wt%, which is added in electric tank cathode room, is used as catholyte.Power on, in electrolysis temperature Degree is 40 DEG C, current density 1.5A/dm2Under conditions of constant-current electrolysis 1h, complete electrolysis after take out catholyte, use 100ml xylene extraction obtains extract liquor, then is successively carried out with 100ml water, 50ml saturated sodium bicarbonate aqueous solution, 100ml water Washing, anhydrous sodium sulfate are dry, concentration, obtain N- methyl, N- propyl pyrrole alkane bromide ionic liquid, and yield 97.2% is pure Degree is 98.8%.
Embodiment 2
It is equipped with three layers of 902 cation-exchange membrane of Nafion in a cell, electrolytic cell is divided into cathode by cation-exchange membrane Room and anode chamber, using PtO2For anode, graphite is cathode, and electrolytic cell sun is added in the glycol water that concentration is 8mol/L It is used as anolyte in pole room, 10gN- methyl nafoxidine and 8.7g n-butanol are added in anode chamber.It is by content The acetonitrile mixed aqueous solution of the KBr of 5wt%, which is added in electric tank cathode room, is used as catholyte.Power on, in electrolysis temperature Degree is 50 DEG C, current density 3A/dm2Under conditions of constant-current electrolysis 2h, complete electrolysis after take out catholyte, use 100ml xylene extraction obtains extract liquor, then is successively carried out with 100ml water, 50ml saturated sodium bicarbonate aqueous solution, 100ml water Washing, anhydrous sodium sulfate are dry, concentration, obtain N- methyl, N- butyl pyrrolidine bromide ionic liquid, and yield 96.4% is pure Degree is 97.5%.
Embodiment 3
It is equipped with three layers of 902 cation-exchange membrane of Nafion in a cell, electrolytic cell is divided into cathode by cation-exchange membrane Room and anode chamber, using PtO2For anode, graphite is cathode, and electrolytic cell sun is added in the glycol water that concentration is 6mol/L It is used as anolyte in pole room, 10gN- propyl nafoxidine and 5.3g normal propyl alcohol are added in anode chamber.It is by content The acetonitrile mixed aqueous solution of the KBr of 4wt%, which is added in electric tank cathode room, is used as catholyte.Power on, in electrolysis temperature Degree is 40 DEG C, current density 1.5A/dm2Under conditions of constant-current electrolysis 1h, complete electrolysis after take out catholyte, use 100ml xylene extraction obtains extract liquor, then is successively carried out with 100ml water, 50ml saturated sodium bicarbonate aqueous solution, 100ml water Washing, anhydrous sodium sulfate are dry, concentration, obtain N, N- dipropyl pyrrolidines bromide ionic liquid, yield 98.7%, and purity is 98.1%.
Embodiment 4
It is equipped with three layers of 902 cation-exchange membrane of Nafion in a cell, electrolytic cell is divided into cathode by cation-exchange membrane Room and anode chamber, using PtO2For anode, graphite is cathode, and electrolytic cell sun is added in the glycol water that concentration is 7mol/L It is used as anolyte in pole room, 10gN- propyl nafoxidine and 6.5g n-butanol are added in anode chamber.It is by content The acetonitrile mixed aqueous solution of the KBr of 5wt%, which is added in electric tank cathode room, is used as catholyte.Power on, in electrolysis temperature Degree is 50 DEG C, current density 2A/dm2Under conditions of constant-current electrolysis 0.5h, complete electrolysis after take out catholyte, use 100ml xylene extraction obtains extract liquor, then is successively carried out with 100ml water, 50ml saturated sodium bicarbonate aqueous solution, 100ml water Washing, anhydrous sodium sulfate are dry, concentration, obtain N- methyl, N- propyl pyrrole alkane bromide ionic liquid, and yield 95.9% is pure Degree is 96.0%.
Embodiment 5
It is equipped with three layers of 902 cation-exchange membrane of Nafion in a cell, electrolytic cell is divided into cathode by cation-exchange membrane Room and anode chamber, using PtO2For anode, graphite is cathode, and electrolytic cell sun is added in the glycol water that concentration is 8mol/L It is used as anolyte in pole room, 10gN- butyl nafoxidine and 5.8g n-butanol are added in anode chamber.It is by content The acetonitrile mixed aqueous solution of the KBr of 5wt%, which is added in electric tank cathode room, is used as catholyte.Power on, in electrolysis temperature Degree is 50 DEG C, current density 2A/dm2Under conditions of constant-current electrolysis 0.5h, complete electrolysis after take out catholyte, use 100ml xylene extraction obtains extract liquor, then is successively carried out with 100ml water, 50ml saturated sodium bicarbonate aqueous solution, 100ml water Washing, anhydrous sodium sulfate are dry, concentration, obtain N, N- dibutyl pyrrolidines bromide ionic liquid, yield 93.5%, and purity is 96.3%.
Embodiment 6
It is equipped with three layers of 902 cation-exchange membrane of Nafion in a cell, electrolytic cell is divided into cathode by cation-exchange membrane Room and anode chamber, using PtO2For anode, graphite is cathode, and electrolytic cell sun is added in the glycol water that concentration is 5mol/L It is used as anolyte in pole room, 10gN- methyl nafoxidine and 12g n-hexyl alcohol are added in anode chamber.It is by content The acetonitrile mixed aqueous solution of the KBr of 3wt%, which is added in electric tank cathode room, is used as catholyte.Power on, in electrolysis temperature Degree is 50 DEG C, current density 2A/dm2Under conditions of constant-current electrolysis 0.5h, complete electrolysis after take out catholyte, use 100ml xylene extraction obtains extract liquor, then is successively carried out with 100ml water, 50ml saturated sodium bicarbonate aqueous solution, 100ml water Washing, anhydrous sodium sulfate are dry, concentration, obtain N- methyl, N- hexyl pyrrolidines bromide ionic liquid, and yield 94.7% is pure Degree is 98.9%.
Embodiment 7
It is equipped with three layers of 902 cation-exchange membrane of Nafion in a cell, electrolytic cell is divided into cathode by cation-exchange membrane Room and anode chamber, using PtO2For anode, graphite is cathode, and electrolytic cell sun is added in the glycol water that concentration is 5mol/L It is used as anolyte in pole room, 10gN- propyl nafoxidine and 9.0g n-hexyl alcohol are added in anode chamber.It is by content The acetonitrile mixed aqueous solution of the KBr of 3wt%, which is added in electric tank cathode room, is used as catholyte.Power on, in electrolysis temperature Degree is 50 DEG C, current density 2A/dm2Under conditions of constant-current electrolysis 0.5h, complete electrolysis after take out catholyte, use 100ml xylene extraction obtains extract liquor, then is successively carried out with 100ml water, 50ml saturated sodium bicarbonate aqueous solution, 100ml water Washing, anhydrous sodium sulfate are dry, concentration, obtain N- propyl, N- hexyl pyrrolidines bromide ionic liquid, and yield 95.1% is pure Degree is 97.6%.
Embodiment 8
It is equipped with three layers of 902 cation-exchange membrane of Nafion in a cell, electrolytic cell is divided into cathode by cation-exchange membrane Room and anode chamber, using PtO2For anode, graphite is cathode, and electrolytic cell sun is added in the glycol water that concentration is 5mol/L It is used as anolyte in pole room, 10gN- butyl nafoxidine and 8.0g n-hexyl alcohol are added in anode chamber.It is by content The acetonitrile mixed aqueous solution of the KBr of 3wt%, which is added in electric tank cathode room, is used as catholyte.Power on, in electrolysis temperature Degree is 50 DEG C, current density 2A/dm2Under conditions of constant-current electrolysis 0.5h, complete electrolysis after take out catholyte, use 100ml xylene extraction obtains extract liquor, then is successively carried out with 100ml water, 50ml saturated sodium bicarbonate aqueous solution, 100ml water Washing, anhydrous sodium sulfate are dry, concentration, obtain N- butyl, N- hexyl pyrrolidines bromide ionic liquid, and yield 92.9% is pure Degree is 98.2%.
Embodiment 9
10g2- chloromethylpyridine is placed in tri- mouthfuls of reaction flasks of 100ml, ionic liquid 30ml prepared by embodiment 1 is added, It is slowly added dropwise 30%wt ammonium hydroxide at 40 DEG C, after TLC monitoring reaction 2- chloromethylpyridine has been reacted, is further continued for being stirred to react 1 small When.Stop reaction, be down to room temperature, be slowly added to deionized water, until precipitating is no longer precipitated, filters, precipitating uses 5wt%Na2CO3 Solution, ethanol washing, dry three (pyridine -2- methyl) amine 5.7g, yield 97.3%, purity 98.6%.
Embodiment 10-18
According to the identical method of embodiment 9, ionic liquid is changed to the ionic liquid of embodiment 2-8, yield and purity It is as follows:
Embodiment Raw material Ionic liquid Yield Purity
10 2- chloromethylpyridine Ionic liquid 2 96.6% 97.3%
11 3- chloromethylpyridine Ionic liquid 3 97.6% 99.1%
12 4- chloromethylpyridine Ionic liquid 4 95.8% 98.9%
13 2- chloromethylpyridine Ionic liquid 5 98.3% 99.5%
14 2- chloromethylpyridine Ionic liquid 6 96.1% 97.9%
15 3- chloromethylpyridine Ionic liquid 7 98.9% 98.2%
16 4- chloromethylpyridine Ionic liquid 8 98.5% 97.4%
17 2- chloromethylpyridine Ionic liquid 3 94.7% 98.2%
18 2- chloromethylpyridine Ionic liquid 7 97.1% 98.3%
The above is only specific embodiments of the present invention, but technical characteristic of the invention is not limited thereto.It is any with this hair Based on bright, to solve essentially identical technical problem, essentially identical technical effect is realized, made simple change, etc. With replacement or modification etc., all it is covered by among protection scope of the present invention.

Claims (10)

1. the preparation method of a kind of N, N- dialkyl pyrrolidinium class bromide ionic liquid, it is characterised in that this method is with N- alkyl four Hydrogen pyrroles and alkylol are that raw material is realized by electrolysis mode, are provided with cation-exchange membrane, cation exchange in a cell Electrolytic cell is divided into cathode chamber and anode chamber by film, is taken out catholyte after completing electrolysis, is isolated and purified, obtain N, N- dialkyl group Pyrrolidines bromide ionic liquid, reaction equation are as follows:
Wherein R1, R2 can be identical or different, are selected from C1-20 linear or branched alkyl group.
2. the preparation method of a kind of N as described in claim 1, N- dialkyl pyrrolidinium class bromide ionic liquid, feature exist C1-6 alkyl is selected from R1 and R2.
3. the preparation method of a kind of N as described in claim 1, N- dialkyl pyrrolidinium class bromide ionic liquid, feature exist PtO is used in electrolytic cell2For anode, graphite is cathode.
4. the preparation method of a kind of N as described in claim 1, N- dialkyl pyrrolidinium class bromide ionic liquid, feature exist It is used as anolyte in the glycol water that concentration is 5-8mol/L to be added in electrolyzer anode chamber, is 2- by content The acetonitrile water mixed solution of the KBr of 5wt%, which is added in electric tank cathode room, is used as catholyte.
5. the preparation method of a kind of N as described in claim 1, N- dialkyl pyrrolidinium class bromide ionic liquid, feature exist In electrolysis temperature be room temperature to 50 DEG C, current density 1-3A/dm2Under conditions of constant-current electrolysis 0.5-2h.
6. the preparation method of a kind of N as described in claim 1, N- dialkyl pyrrolidinium class bromide ionic liquid, feature exist In cation-exchange membrane be Nafion cation-exchange membrane, preferably 902 cation-exchange membrane of Nafion.
7. the preparation method of a kind of N as described in claim 1, N- dialkyl pyrrolidinium class bromide ionic liquid, feature exist In by filled respectively in two reservoirs concentration be 5-8mol/L glycol water as anode replenisher, content is The acetonitrile water mixed solution of the KBr of 2-5wt% passes through two circulating pumps respectively by electrolyzer anode chamber as cathode replenisher With a reservoir, electric tank cathode room is connected to another reservoir, and two circulating pumps are respectively by anolyte and cathode Electrolyte is constantly swapped with anode replenisher and cathode replenisher, so that the anode in electrolyzer anode chamber and cathode chamber Electrolyte and catholyte keep stable concentration.
8. the preparation method of a kind of N as described in claim 1, N- dialkyl pyrrolidinium class bromide ionic liquid, feature exist After completing to be electrolysed taking-up catholyte, extract liquor first is obtained with xylene extraction, then molten with water, saturated sodium bicarbonate water Liquid, water are successively washed, and anhydrous magnesium sulfate is dry, and concentration obtains the N, N- dialkyl pyrrolidinium class bromide ionic liquid.
9. the purposes of a kind of N as described in claim 1, N- dialkyl pyrrolidinium class bromide ionic liquid, it is characterised in that With N, N- dialkyl pyrrolidinium class bromide ionic liquid is solvent, using the hydrochloride of chloromethylpyridine and ammonium hydroxide as raw material, synthesis Three picolyl aminated compounds, as follows for specific reaction step:
Wherein: one of X1, X2 and X3 are N atom;
By the hydrochloride and N of chloromethylpyridine, N- dialkyl pyrrolidinium class bromide ionic liquid mixes in reactor, and control exists 40-70 DEG C, ammonium hydroxide is then slowly added dropwise under stiring, after detecting the fully reacting of raw material chloromethylpyridine stops that ammonium hydroxide is added dropwise, so After be stirred for 1 hour, stop reaction, be down to room temperature, be slowly added to deionized water, Precipitation, filtering, precipitating uses Na2CO3It is molten Liquid, ethanol washing, dry product.
10. a kind of purposes as claimed in claim 9, it is characterised in that ammonium hydroxide is the ammonium hydroxide that mass percent concentration is 30%; Na2CO3Solution is the Na that mass percent concentration is 5%2CO3Solution.
CN201910197327.5A 2019-03-15 2019-03-15 N, N- dialkyl pyrrolidinium bromide ionic liquid preparation method and applications Active CN109825848B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201910197327.5A CN109825848B (en) 2019-03-15 2019-03-15 N, N- dialkyl pyrrolidinium bromide ionic liquid preparation method and applications

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201910197327.5A CN109825848B (en) 2019-03-15 2019-03-15 N, N- dialkyl pyrrolidinium bromide ionic liquid preparation method and applications

Publications (2)

Publication Number Publication Date
CN109825848A true CN109825848A (en) 2019-05-31
CN109825848B CN109825848B (en) 2019-10-18

Family

ID=66870207

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201910197327.5A Active CN109825848B (en) 2019-03-15 2019-03-15 N, N- dialkyl pyrrolidinium bromide ionic liquid preparation method and applications

Country Status (1)

Country Link
CN (1) CN109825848B (en)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4083851A (en) * 1974-01-07 1978-04-11 Diamond Shamrock Corporation Cis-2,5-dialkylpyrrolidine process
CN101412694A (en) * 2008-11-28 2009-04-22 江苏大学 Preparation of efficient green tripyridyl methyl amine compounds
CN105568312A (en) * 2016-01-06 2016-05-11 中山大学 Method for synthesizing 2-arylpyrrole-compound through indirect electro-catalysis
CN109082680A (en) * 2018-09-04 2018-12-25 安庆师范大学 A kind of preparation method of bipyridines ionic liquid

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4083851A (en) * 1974-01-07 1978-04-11 Diamond Shamrock Corporation Cis-2,5-dialkylpyrrolidine process
CN101412694A (en) * 2008-11-28 2009-04-22 江苏大学 Preparation of efficient green tripyridyl methyl amine compounds
CN105568312A (en) * 2016-01-06 2016-05-11 中山大学 Method for synthesizing 2-arylpyrrole-compound through indirect electro-catalysis
CN109082680A (en) * 2018-09-04 2018-12-25 安庆师范大学 A kind of preparation method of bipyridines ionic liquid

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WILLIAM H. PEARSON 等: "Formation and cycloaddition of nonstabilized N-unsubstituted azomethine ylides from (2-azaallyl)stannanes and (2-azaallyl)silanes", 《TETRAHEDRON LETTERS》 *

Also Published As

Publication number Publication date
CN109825848B (en) 2019-10-18

Similar Documents

Publication Publication Date Title
US4435256A (en) Process for making potassium ferrate [Fe(VI)] by the electrochemical formation of sodium ferrate
ES2657763T3 (en) Redox flow stack for the storage of electrical energy and its use
KR840006830A (en) Electrolytic Manufacturing Method Of Organic Compound And Electrolyzer
CN101486661A (en) Method for preparing tetraalkyl quaternary ammonium type amino acid ion liquid
CN105887128A (en) Method for electrical-catalytic and selective hydrogenating and dechlorinating of pentachloropyridine
CA1163598A (en) Electrochemical production of metal alkoxides in membrane cell
CN115304487B (en) Synthesis method of dimethyl diallyl ammonium chloride
CN110745795B (en) Method for synthesizing lithium bis (fluorosulfonyl) imide by using electrochemistry
WO1990015170A1 (en) Production of quaternary ammonium and quaternary phosphonium borohydrides
CN102050788A (en) Method for synthesizing halogen-free imidazole ionic liquid
CN109825848B (en) N, N- dialkyl pyrrolidinium bromide ionic liquid preparation method and applications
JP2010520150A (en) Ultra high purity zinc bromide and quaternary ammonium bromide for use in zinc-bromine batteries
CN103276403A (en) Method for preparing long-chain alkyl ammonium hydroxide
NO153614B (en) PROCEDURE AND ELECTROLYCLE CELLS FOR THE PREPARATION OF ALKANDIOLS.
CN107417588A (en) A kind of novel ion liquid and the method using its electrolytic preparation nano aluminum
JP2007077046A (en) Method for producing spiro compound
CN105696017B (en) A kind of new technique method of iron reduction nitrobenzene
US6274114B1 (en) Process for on-site production of ultra-high-purity hydrogen peroxide for the electronics industry
CN110699700A (en) Preparation method of adamantyl trimethyl ammonium hydroxide
CN114000169B (en) Electrochemical preparation method of allicin compound
US20240209520A1 (en) Apparatus for manufacturing nitrogen-containing compound and method for manufacturing nitrogen-containing compound
CN109082680A (en) A kind of preparation method of bipyridines ionic liquid
CN105862072B (en) A kind of new technique method of zinc reduction nitrobenzene
CN102021604B (en) Method for preparing succinic acid based on alloy wire mesh-bipolar film combined electrode technology
AU2175602A (en) Process for improving the purity of quaternary ammonium hydroxides by electrolysis

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant