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 PDFInfo
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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
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.
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| 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 |
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