CN108793104B - Nitric oxide phase transfer catalysis method - Google Patents
Nitric oxide phase transfer catalysis method Download PDFInfo
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- CN108793104B CN108793104B CN201710298725.7A CN201710298725A CN108793104B CN 108793104 B CN108793104 B CN 108793104B CN 201710298725 A CN201710298725 A CN 201710298725A CN 108793104 B CN108793104 B CN 108793104B
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- nitric oxide
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- phase transfer
- gas
- catalysis method
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- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 title claims abstract description 81
- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000003408 phase transfer catalysis Methods 0.000 title claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 239000003444 phase transfer catalyst Substances 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 claims description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000007789 gas Substances 0.000 abstract description 18
- 239000007788 liquid Substances 0.000 abstract description 5
- 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 14
- 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
- 239000012071 phase Substances 0.000 description 11
- 230000003197 catalytic effect Effects 0.000 description 9
- 239000000126 substance Substances 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical group 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003701 histiocyte Anatomy 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000002464 muscle smooth vascular Anatomy 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- VZQAQPGIOPQBGU-UHFFFAOYSA-N oxidoiminoiron(1+) Chemical compound [Fe]N=O VZQAQPGIOPQBGU-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000007704 transition 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a phase transfer catalysis method for promoting a nitrogen monoxide gas liquid mass transfer process, in particular to a phase transfer catalysis method for accelerating nitrogen monoxide in a gas phase to enter a water phase by using a catalyst. The method can obviously improve the efficiency of the gas-phase nitric oxide entering the water phase, and has the advantages of simple operation, lower cost and wide application range.
Description
Technical Field
The invention relates to a phase transfer catalysis method for promoting a nitrogen monoxide gas liquid mass transfer process, in particular to a phase transfer catalysis method for accelerating nitrogen monoxide in a gas phase to enter a water phase by using a catalyst, and belongs to the field of catalysis.
Background
Nitric oxide is an important inorganic chemical molecule with physiological effects, and three scholars have acquired the prize of nobel's biomedicine in 1998 because it was found to dilate vascular smooth muscle and thereby dilate blood vessels. Therefore, it has been extensively studied in the fields of biology and medicine, and found that nitric oxide can be present in various human histiocytes to act as messenger molecules, which have effects on cardiovascular and cerebrovascular systems, nervous system, and immune system. Its clinical medical applications will be fed back into the field of chemical synthesis.
In the chemical field, nitric oxide can form nitrosyl complexes with a variety of transition group metals, which are used as homogeneous catalysts in a variety of chemical reactions.
From a synthetic point of view, nitrosyl complexes of nitric oxide are very similar to carbonyl compounds, but the latter are often prepared by reacting carbon monoxide with the complex under high temperature and pressure conditions, at which nitrogen monoxide disproportionates and decomposes due to its thermodynamic instability, most nitrosyl complexes being prepared by conversion of a pre-existing NO complex. The other difficulty is that nitric oxide is insoluble in water, and the resistance of nitric oxide entering a liquid phase is extremely high at normal temperature and normal pressure, so that the reaction rate of nitric oxide entering a water phase system is extremely low, and the reaction efficiency is poor.
In view of the above problems, we propose a phase transfer catalysis method, which aims to accelerate the rate of nitric oxide entering the water phase, and since the phase transfer and diffusion of nitric oxide are the rate control steps of the overall reaction, the reaction efficiency of gas phase nitric oxide and reactants in the liquid phase can be greatly improved by improving the heterogeneous mass transfer process.
Disclosure of Invention
The invention relates to a phase transfer catalysis method for promoting a nitrogen monoxide liquid mass transfer process, in particular to a phase transfer catalysis method for accelerating nitrogen monoxide in a gas phase to enter a water phase by using a catalyst, which comprises the following operation steps:
adding a phase transfer catalyst into an aqueous phase solution containing reactants, wherein the addition amount mass concentration is generally not more than 1%, and reacting the solution with gas-phase nitric oxide.
The phase transfer catalyst employs a substance or mixture of substances having the following structure:
(1)R1OH
(2)R2(OH)n
(3)R3OR4
(4)R5(O)R6(OH)n
(5)A(OH)n
wherein R is1And R2Is one of C1-C6 straight chain or alkyl containing a branched chain, C2-C6 straight chain or alkenyl containing a branched chain and C5-C6 naphthenic base or cycloalkenyl;
R3and R4Is one of C1-C3 linear chain or branched chain-containing alkyl, C2-C4 linear chain or branched chain-containing alkenyl;
R5and R6Is one of C1-C3 linear chain or branched chain-containing alkyl, C2-C6 linear chain or branched chain-containing alkenyl;
a is an oxygen-containing cyclic ether group of C3-C6, and n is a positive integer less than 6.
The invention has the advantages of
The phase transfer catalysis method provided by the invention is suitable for the condition that nitric oxide can exist stably, namely the temperature is not too high and the pressure is not too high. On the premise, the method provided by the invention is suitable for the reaction of all gas-phase nitric oxide and reactants existing in the aqueous solution, and has a wide application range.
In the catalytic method provided by the invention, the phase transfer catalyst is simple and easy to obtain, the cost is lower, but the catalytic effect is obvious, and the reaction efficiency of nitric oxide and a liquid-phase reactant is greatly improved.
DETAILED DESCRIPTION OF EMBODIMENT (S) OF INVENTION
The invention is further illustrated by the following specific examples:
the phase transfer catalytic effect provided by the present invention is obviously affected by different pressures, different temperatures, and different concentrations of reactants, and this example is only an illustration, and obviously, the implementation conditions of the present invention are not limited to the description of the example.
At normal temperature and normal pressure, nitric oxide gas is continuously introduced into ferrous sulfate solution, and nitrosyl iron [ Fe (H) is generated in the reaction2O)5NO]2+The substance is brown, and since the speed of nitric oxide breaking through the liquid film is slow, the liquid will change color after a period of gas introduction.
The experiment shows the effect of the catalytic method by comparing the method of adding the phase transfer catalyst with a blank sample.
Example 1
The solution was initially discolored after approximately 10 seconds by a constant introduction of 10% nitric oxide gas into a solution containing 5000ppm of ferrous sulfate.
After 2000ppm of diethylene glycol and 1000ppm of glycerol were added to a ferrous sulfate solution containing 5000ppm, 10% nitric oxide gas was continuously introduced in the same amount, and the solution was discolored for 4 seconds.
Under the condition, the catalytic method improves the total reaction efficiency by 150 percent.
Example 2
The solution was initially discolored after approximately 10 seconds by a constant introduction of 10% nitric oxide gas into a solution containing 5000ppm of ferrous sulfate.
After 2000ppm tetrahydrofurfuryl alcohol was added to the ferrous sulfate solution containing 5000ppm, 10% nitric oxide gas was also continuously introduced quantitatively, and the solution discolored for 3 seconds first.
Under the condition, the catalytic method improves the total reaction efficiency by 230 percent.
Example 3
The solution was initially discolored after approximately 10 seconds by a constant introduction of 10% nitric oxide gas into a solution containing 5000ppm of ferrous sulfate.
After 2000ppm of ethylene glycol was added to the ferrous sulfate solution containing 5000ppm, 10% nitric oxide gas was continuously introduced in the same amount, and the solution was discolored for 3 seconds.
Under the condition, the catalytic method improves the total reaction efficiency by 230 percent.
Example 4
The solution was initially discolored after approximately 10 seconds by a constant introduction of 10% nitric oxide gas into a solution containing 5000ppm of ferrous sulfate.
After 1000ppm of tetrahydrofuran, 1000ppm of diethylene glycol ethyl ether and 1000ppm of propylene glycol were added to a solution containing 5000ppm of ferrous sulfate, 10% of nitric oxide gas was continuously introduced in the same amount, and the solution was discolored for 3 seconds.
Under the condition, the catalytic method improves the total reaction efficiency by 230 percent.
Example 5
The solution was initially discolored after approximately 10 seconds by a constant introduction of 10% nitric oxide gas into a solution containing 5000ppm of ferrous sulfate.
1000ppm of n-pentanol and 1000ppm of triethylene glycol are added to a ferrous sulfate solution containing 5000ppm, 10% of nitric oxide gas is continuously introduced in the same quantitative manner, and the solution is discolored for the first time after 4 s.
Under the condition, the catalytic method improves the total reaction efficiency by 150 percent.
Claims (1)
1. A phase transfer catalysis method for nitric oxide is characterized in that the phase transfer catalysis method is applied to catalytically accelerate nitric oxide in a gas phase to enter a water phase and comprises the following operation steps:
adding a phase transfer catalyst into a water phase solution containing reactants, wherein the addition amount mass concentration is not more than 1%, and reacting the solution with gas-phase nitric oxide;
the phase transfer catalyst is diethylene glycol and glycerol or tetrahydrofurfuryl alcohol or ethylene glycol or tetrahydrofuran, diethylene glycol ethyl ether and propylene glycol or n-amyl alcohol and triethylene glycol.
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| CN201710298725.7A CN108793104B (en) | 2017-04-28 | 2017-04-28 | Nitric oxide phase transfer catalysis method |
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| CN201710298725.7A CN108793104B (en) | 2017-04-28 | 2017-04-28 | Nitric oxide phase transfer catalysis method |
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| Publication Number | Publication Date |
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| CN108793104A CN108793104A (en) | 2018-11-13 |
| CN108793104B true CN108793104B (en) | 2021-01-08 |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6844464B2 (en) * | 2002-03-18 | 2005-01-18 | Ube Industries, Ltd. | Process for producing alkyl nitrite |
| CN102973948B (en) * | 2012-12-03 | 2014-08-20 | 上海交通大学 | Method for preparing drug carrier based on magnetic carbon quantum dot/chitosan composite microsphere |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 (2)
| Title |
|---|
| Metal complex and phase transfer catalysed nitric oxide reactions;Slavomir Falicky et al.;《Journal of the Chemical Society, Chemical Communications》;19870101(第13期);1039-1041 * |
| Slavomir Falicky et al..Metal complex and phase transfer catalysed nitric oxide reactions.《Journal of the Chemical Society, Chemical Communications》.1987,(第13期), * |
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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 |