CN108793104A - A kind of nitric oxide phase transfer catalyzed methods - Google Patents
A kind of nitric oxide phase transfer catalyzed methods Download PDFInfo
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- CN108793104A CN108793104A CN201710298725.7A CN201710298725A CN108793104A CN 108793104 A CN108793104 A CN 108793104A CN 201710298725 A CN201710298725 A CN 201710298725A CN 108793104 A CN108793104 A CN 108793104A
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- nitric oxide
- phase
- phase transfer
- branch
- straight chains
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- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 title claims abstract description 79
- 238000000034 method Methods 0.000 title claims abstract description 25
- 238000012546 transfer Methods 0.000 title claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000012071 phase Substances 0.000 claims description 22
- 238000006555 catalytic reaction Methods 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000003444 phase transfer catalyst Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000011017 operating method Methods 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 230000001133 acceleration Effects 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 3
- 230000001737 promoting effect Effects 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 13
- 235000003891 ferrous sulphate Nutrition 0.000 description 11
- 239000011790 ferrous sulphate Substances 0.000 description 11
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 11
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 11
- 230000008569 process Effects 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000003408 phase transfer catalysis Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 210000002464 muscle smooth vascular Anatomy 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B21/00—Nitrogen; Compounds thereof
- C01B21/082—Compounds containing nitrogen and non-metals and optionally metals
- C01B21/087—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms
- C01B21/093—Compounds containing nitrogen and non-metals and optionally metals containing one or more hydrogen atoms containing also one or more sulfur atoms
Abstract
The present invention relates to a kind of phase transfer catalyzed methods for promoting nitric oxide mass-transfer progress, and the phase transfer catalyzed methods of water phase are specifically entered using nitric oxide in catalyst acceleration gas phase.The efficiency that gas phase nitric oxide enters water phase can significantly be improved using this method, and easy to operate, cost is relatively low, has wide range of applications.
Description
Technical field
The present invention relates to a kind of phase transfer catalyzed methods for promoting nitric oxide mass-transfer progress, specifically use
Nitric oxide enters the phase transfer catalyzed methods of water phase in catalyst acceleration gas phase, and this method belongs to catalytic field.
Background technology
Nitric oxide is the important non-organic chemical molecules for having physiological action, because it is found that its expand vascular smooth muscle to
Vasodilation, three scholars is set to obtain Nobel Prize in Physiology or Medicine in 1998.Therefore, it is obtained in biological and medical field
Extensive research, research finds that nitric oxide can reside in the various of people and serves as messenger molecule, to heart and brain blood
Pipe, nervous system, immune system have an impact.Its clinical medical application can feed back to the field of chemical synthesis.
In chemical field, nitric oxide can with a variety of magnesium-yttrium-transition metals formed nitrosyl complex, and the latter mostly by
As the homogeneous catalyst in all kinds of chemical reactions.
It is said from synthetic degree of angle, nitric oxide production nitrosyl complex is very similar with carbonyls, but the latter is often logical
Made of crossing carbon monoxide and complex under the conditions of high-temperature high-voltage reaction, and nitric oxide is due to its thermodynamic instability
Property, it can be disproportionated and decompose at this temperature and pressure, most nitrosyl complexs are coordinated by pre-existing NO
Object changes and is made.Another difficulty is that nitric oxide is not soluble in water, and at normal temperatures and pressures, nitric oxide enters liquid phase
Resistance is very big, and all nitric oxides that are related to enter that the reaction rate of aqueous phase system is all extremely slow, and reaction efficiency is poor.
In view of the above-mentioned problems, we have proposed a kind of phase transfer catalyzed methods, the purpose is to accelerate nitric oxide to enter water
The rate of phase, since nitric oxide production alternate migration and diffusion are the ratedeterming step of overall reaction, so passing through improvement out-phase mass transfer
Process can greatly improve the reaction efficiency of gas phase nitric oxide and reactant in liquid phase.
Invention content
The present invention relates to a kind of phase transfer catalyzed methods for promoting nitric oxide mass-transfer progress, specifically use
Nitric oxide enters the phase transfer catalyzed methods of water phase in catalyst acceleration gas phase, including following operating procedure：
Phase transfer catalyst is added in the aqueous phase solution containing reactant, addition mass concentration is generally no greater than 1%,
It is reacted with gas phase nitric oxide using the solution.
Phase transfer catalyst uses the mixture of the substance or substance that have following structure：
(1)R1OH
(2)R2(OH)n
(3)R3OR4
(4)R5(O)R6(OH)n
(5)A(OH)n
Wherein, R1And R2For C1-C6 straight chains or contain the alkyl of branch, C2-C6 straight chains or the alkenyl containing branch and C5-
The naphthenic base or cycloalkenyl group one of which of C6；
R3And R4For C1-C3 straight chains or the alkenyl one of which containing the alkyl of branch, C2-C4 straight chains or containing branch；
R5And R6For C1-C3 straight chains or the alkenyl one of which containing the alkyl of branch, C2-C6 straight chains or containing branch；
A is the ether ring ether of C3-C6, and n is the positive integer less than 6.
Beneficial effects of the present invention
Phase transfer catalyzed methods provided by the invention are suitable in the case that nitric oxide can be stabilized, i.e., temperature is not
It is too high, in the case that pressure is less big.Under the premise of herein, method provided by the invention is suitable for all gas phase nitric oxides and deposits
It is that the reaction that the reactant in aqueous solution occurs, the scope of application are wider.
In catalysis process provided by the invention, phase transfer catalyst is simple and easy to get and cost is relatively low, but catalytic effect is apparent,
Greatly improve the reaction efficiency of nitric oxide and liquid phase reactor object.
Specific embodiment
It is following that invention is further detailed by some specific examples：
Phase transfer catalysis (PTC) effect provided by the invention will obviously by different pressures, different temperatures and various concentration
The influence of reactant, the merely illustrative explanation of the present embodiment, it is clear that implementation condition of the invention is not limited to the explanation of embodiment.
Under normal temperature and pressure, nitric oxide gas is continually fed into containing ferrous sulfate solution, which can generate nitrous
Acyl closes iron [Fe (H2O)5NO]2+, which is in brown, since the speed that nitric oxide breaks through liquid film is slower, is being passed through gas one
After the section time, liquid can just change colour.
Experiment is compared using the method that phase transfer catalyst is added with blank sample, to illustrate the effect of this catalysis process
Fruit.
Embodiment 1
Quantitative continuous is passed through 10% nitric oxide gas in the ferrous sulfate solution containing 5000ppm, after general 10s
Solution changes colour for the first time.
The diethylene glycol of 2000ppm and the glycerine of 1000ppm are added in the ferrous sulfate solution containing 5000ppm
Afterwards, same quantitative continuous is passed through 10% nitric oxide gas, and solution changes colour for the first time after 4s.
Under this condition, this catalysis process makes overall reaction efficiency improve 150%.
Embodiment 2
Quantitative continuous is passed through 10% nitric oxide gas in the ferrous sulfate solution containing 5000ppm, after general 10s
Solution changes colour for the first time.
After the tetrahydrofurfuryl alcohol of 2000ppm is added in the ferrous sulfate solution containing 5000ppm, same quantitative continuous is passed through
10% nitric oxide gas, solution changes colour for the first time after 3s.
Under this condition, this catalysis process makes overall reaction efficiency improve 230%.
Embodiment 3
Quantitative continuous is passed through 10% nitric oxide gas in the ferrous sulfate solution containing 5000ppm, after general 10s
Solution changes colour for the first time.
After the ethylene glycol of 2000ppm is added in the ferrous sulfate solution containing 5000ppm, same quantitative continuous is passed through
10% nitric oxide gas, solution changes colour for the first time after 3s.
Under this condition, this catalysis process makes overall reaction efficiency improve 230%.
Embodiment 4
Quantitative continuous is passed through 10% nitric oxide gas in the ferrous sulfate solution containing 5000ppm, after general 10s
Solution changes colour for the first time.
The tetrahydrofuran of 1000ppm, the diethylene glycol of 1000ppm are added in the ferrous sulfate solution containing 5000ppm
After the propylene glycol of ether and 1000ppm, same quantitative continuous is passed through 10% nitric oxide gas, and solution changes colour for the first time after 3s.
Under this condition, this catalysis process makes overall reaction efficiency improve 230%.
Embodiment 5
Quantitative continuous is passed through 10% nitric oxide gas in the ferrous sulfate solution containing 5000ppm, after general 10s
Solution changes colour for the first time.
The n-amyl alcohol of 1000ppm, the triethylene glycol of 1000ppm are added in the ferrous sulfate solution containing 5000ppm, together
Sample quantitative continuous is passed through 10% nitric oxide gas, and solution changes colour for the first time after 4s.
Under this condition, this catalysis process makes overall reaction efficiency improve 150%.
Claims (2)
1. one kind be used for nitric oxide production phase transfer catalyzed methods, it is characterized in that applied to catalysis accelerate gas phase in nitric oxide into
Enter the phase transfer catalyzed methods of water phase, including following operating procedure：
Phase transfer catalyst is added in the aqueous phase solution containing reactant, addition mass concentration is molten using this no more than 1%
Liquid is reacted with gas phase nitric oxide.
2. one kind being used for nitric oxide production phase transfer catalyzed methods, it is characterized in that using the operating procedure described in claim 1,
Phase transfer catalyst uses the mixture of the substance or substance that have following structure simultaneously：
(1)R1OH
(2)R2(OH)n
(3)R3OR4
(4)R5(O)R6(OH)n
(5)A(OH)n
Wherein, R1And R2For C1-C6 straight chains or the alkenyl containing the alkyl of branch, C2-C6 straight chains or containing branch and C5-C6
Naphthenic base or cycloalkenyl group one of which；
R3And R4For C1-C3 straight chains or the alkenyl one of which containing the alkyl of branch, C2-C4 straight chains or containing branch；
R5And R6For C1-C3 straight chains or the alkenyl one of which containing the alkyl of branch, C2-C6 straight chains or containing branch；
A is the ether ring ether of C3-C6, and n is the positive integer less than 6.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710298725.7A CN108793104B (en) | 2017-04-28 | 2017-04-28 | Nitric oxide phase transfer catalysis method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710298725.7A CN108793104B (en) | 2017-04-28 | 2017-04-28 | Nitric oxide phase transfer catalysis method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108793104A true CN108793104A (en) | 2018-11-13 |
| CN108793104B CN108793104B (en) | 2021-01-08 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710298725.7A Active CN108793104B (en) | 2017-04-28 | 2017-04-28 | Nitric oxide phase transfer catalysis method |
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| Country | Link |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1445208A (en) * | 2002-03-18 | 2003-10-01 | 宇部兴产株式会社 | Method for producing arrcostab nitrite |
| CN102973948A (en) * | 2012-12-03 | 2013-03-20 | 上海交通大学 | Method for preparing drug carrier based on magnetic carbon quantum dot/chitosan composite microsphere |
| CN103012074A (en) * | 2012-12-31 | 2013-04-03 | 大连百傲化学股份有限公司 | Method for preparing aromatic methyl ether compound |
| CN103463970A (en) * | 2013-09-05 | 2013-12-25 | 南昌大学 | New method for treating nitrogen oxide waste gas |
| CN104548904A (en) * | 2013-10-16 | 2015-04-29 | 北京化工大学 | Technology for liquid-phase complexing absorption of NO with iron-based chelate |
-
2017
- 2017-04-28 CN CN201710298725.7A patent/CN108793104B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1445208A (en) * | 2002-03-18 | 2003-10-01 | 宇部兴产株式会社 | Method for producing arrcostab nitrite |
| CN102973948A (en) * | 2012-12-03 | 2013-03-20 | 上海交通大学 | Method for preparing drug carrier based on magnetic carbon quantum dot/chitosan composite microsphere |
| CN103012074A (en) * | 2012-12-31 | 2013-04-03 | 大连百傲化学股份有限公司 | Method for preparing aromatic methyl ether compound |
| CN103463970A (en) * | 2013-09-05 | 2013-12-25 | 南昌大学 | New method for treating nitrogen oxide waste gas |
| CN104548904A (en) * | 2013-10-16 | 2015-04-29 | 北京化工大学 | Technology for liquid-phase complexing absorption of NO with iron-based chelate |
Non-Patent Citations (1)
| Title |
|---|
| SLAVOMIR FALICKY ET AL.: "Metal complex and phase transfer catalysed nitric oxide reactions", 《JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS》 * |
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| CN108793104B (en) | 2021-01-08 |
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Effective date of registration: 20240228 Address after: No. 212, Building 34, Yuqiao Nanli, Tongzhou District, Beijing, 101100 Patentee after: Wei Yusheng Country or region after: China Address before: 102218 814, 8th floor, building 43, tiantongzhongyuan 2nd District, Tiantongyuan North Street, Changping District, Beijing Patentee before: BEIJING SUN-SILVER SCIENCE & TECHNOLOGY Co.,Ltd. Country or region before: China |