CN114315907A - Porous methyl rhenium trioxide and application method thereof - Google Patents
Porous methyl rhenium trioxide and application method thereof Download PDFInfo
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- CN114315907A CN114315907A CN202111473206.2A CN202111473206A CN114315907A CN 114315907 A CN114315907 A CN 114315907A CN 202111473206 A CN202111473206 A CN 202111473206A CN 114315907 A CN114315907 A CN 114315907A
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- porous
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- methyltrioxorhenium
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- ionic liquid
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- VZSXFJPZOCRDPW-UHFFFAOYSA-N carbanide;trioxorhenium Chemical compound [CH3-].O=[Re](=O)=O VZSXFJPZOCRDPW-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title description 7
- 239000002608 ionic liquid Substances 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 238000003756 stirring Methods 0.000 claims abstract description 18
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 10
- 238000001816 cooling Methods 0.000 claims abstract description 9
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 238000002156 mixing Methods 0.000 claims abstract description 9
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 8
- 239000011591 potassium Substances 0.000 claims abstract description 8
- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000005051 trimethylchlorosilane Substances 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 6
- 230000035484 reaction time Effects 0.000 claims abstract description 6
- 238000005406 washing Methods 0.000 claims abstract description 6
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 238000001308 synthesis method Methods 0.000 claims abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 230000008859 change Effects 0.000 claims description 5
- IKWLASUDSGDILR-UHFFFAOYSA-N 1-heptyl-3-methyl-1,2-dihydroimidazol-1-ium;chloride Chemical compound [Cl-].CCCCCCC[NH+]1CN(C)C=C1 IKWLASUDSGDILR-UHFFFAOYSA-N 0.000 claims description 3
- 238000006392 deoxygenation reaction Methods 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 230000003197 catalytic effect Effects 0.000 abstract description 5
- 239000007809 chemical reaction catalyst Substances 0.000 abstract description 2
- 150000002736 metal compounds Chemical class 0.000 abstract description 2
- 229910052702 rhenium Inorganic materials 0.000 abstract description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 abstract description 2
- 238000006555 catalytic reaction Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229940031723 1,2-octanediol Drugs 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical compound CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000002604 ultrasonography Methods 0.000 description 3
- LTUJTQNLFHRCMU-UHFFFAOYSA-M 1-heptyl-3-methylimidazol-3-ium;chloride Chemical compound [Cl-].CCCCCCC[N+]=1C=CN(C)C=1 LTUJTQNLFHRCMU-UHFFFAOYSA-M 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000005486 organic electrolyte Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
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Abstract
The invention belongs to the field of organic metal compound synthesis, and particularly relates to porous methyl rhenium trioxide, which is prepared by adding a proper amount of ionic liquid, water and an auxiliary agent into a reaction kettle, stirring and mixing uniformly at the temperature of 20-40 ℃ under normal pressure, then adding potassium perrhenate into a system, stirring for 1-2 hours, then adding trimethylchlorosilane and tetramethyltin, heating, properly prolonging the reaction time by controlling the end point according to color, cooling, stopping stirring, and filtering, washing, distilling and recrystallizing after the reaction is finished to obtain the porous methyl rhenium trioxide; the porous methyl rhenium trioxide is applied to alcohol deoxidation and dehydration reaction, and shows good catalytic activity. The porous rhenium catalyst has the advantages of simple synthesis method, green reaction and no pollution, can be recycled as the alcohol deoxidation and dehydration reaction catalyst, protects the environment, and greatly reduces the catalysis cost.
Description
Technical Field
The invention belongs to the field of synthesis of organic metal compounds, and particularly relates to porous methyl rhenium trioxide and an application method thereof.
Background
The ionic liquid is a room-temperature molten salt which consists of anions and cations and has a melting point lower than 100 ℃, and is one of research hotspots for over ten years. Research shows that the ionic liquid has many unique physical and chemical properties, such as low vapor pressure (almost zero), non-flammability, good thermal stability, high conductivity, wide electrochemical window, large heat capacity, wide liquid path, strong dissolving capacity and the like. In addition, the ionic liquid has the advantages of ordered local structure, adjustable property from hydrophilicity to hydrophobicity, repeated cyclic utilization and the like. More importantly, the ionic liquid has designability, and the ionic liquid with special functions can be prepared by changing the types of anions and cations or introducing specific functional groups according to experimental needs. The ionic liquid as a novel green solvent replaces the traditional organic solvent and electrolyte, and shows good characteristics and wide application prospects in the aspects of chemical reaction, extraction separation, gas absorption, material science, electrochemistry and the like. The ionic liquid system has strong interaction such as charge action, hydrogen bond action, hydrophobic action and the like, and has strong solubility, so the ionic liquid system has very wide application in the aspect of material synthesis.
Rhenium methyltrioxide, abbreviated as MTO, is a transition metal organic catalyst that has emerged in recent years and is increasingly recognized as having high efficiency and high selectivity for catalyzing organic synthesis reactions such as the oxidation of unsaturated hydrocarbons, the oxidation of aromatic compounds, and the oxidation of heteroatom-containing organic compounds. The currently synthesized MTO is non-porous, the catalytic activity needs to be further improved when the synthesized MTO is used as a catalyst, and when the MTO is endowed with a pore channel structure, the specific surface area can be increased so as to improve the catalytic performance, so that the development of the porous methyl rhenium trioxide is particularly important.
Disclosure of Invention
In order to solve the problems, the invention provides porous methyl rhenium trioxide, which adopts the following technical scheme: a porous methyl rhenium trioxide is synthesized by the following steps: adding a proper amount of ionic liquid, water and an auxiliary agent into a reaction kettle, stirring and mixing uniformly at the temperature of 20-40 ℃ under normal pressure, then adding potassium perrhenate into the system, stirring for 1-2 hours, then adding trimethylchlorosilane and tetramethyltin, heating, taking the color change of the initial solution as the reaction end point when the color is not changed, prolonging the reaction time for 0.5-2 hours, cooling, stopping stirring, and after the reaction is finished, filtering, washing, distilling and recrystallizing to obtain white powdery porous methyl rhenium trioxide.
In the porous methyltrioxorhenium, the ionic liquid is preferably 1-heptyl-3-methylimidazolium chloride (C)7mimBr)。
Further, the mass ratio of the ionic liquid to the water is (5-1): 1.
The above porous methyl rhenium trioxide is preferably prepared by using dichloromethane as the auxiliary agent.
The porous methyltrioxorhenium is preferably added in an amount of 10 to 50%.
Preferably, when porous methyl rhenium trioxide is synthesized, the mass ratio of the ionic liquid, the potassium perrhenate, the trimethylchlorosilane to the tetramethyltin is 50: (1.5-1): (1.4-1): (1.2-1).
The invention also provides an application method of the porous methyl rhenium trioxide, and the porous methyl rhenium trioxide is added into an alcohol deoxidation and dehydration reaction to be used as an alcohol deoxidation and dehydration reaction catalyst, so that good catalytic activity is shown.
The invention has the beneficial effects that: the invention synthesizes porous methyl rhenium trioxide by inducing an ionic liquid aqueous solution to form a gel mixture through a solvent dichloromethane. The method has the advantages of simple process, mild conditions, greenness and controllability, and universality, and the obtained porous methyl rhenium trioxide has stable performance and controllable pore diameter. The methyl rhenium trioxide prepared by the invention is used as a catalyst for alcohol deoxidation and dehydration reaction, the catalytic activity is good, and the yield is up to more than 99%.
Detailed Description
The present invention is further illustrated by the following specific examples, which should not be construed as limiting the invention, but rather as embodying the invention in its scope by modifying or substituting the methods, steps or conditions of the present invention without departing from the spirit and substance of the invention.
Example 1:
synthesis of porous methyl rhenium trioxide:
adding 7 parts of ionic liquid 1-heptyl-3-methylimidazolium chloride, 3 parts of water and 15% dichloromethane into a reaction kettle, stirring and mixing uniformly at 25 ℃ under normal pressure, then adding 0.15 part of potassium perrhenate into the system, stirring for 1 hour, then adding 0.15 part of trimethylchlorosilane and 0.15 part of tetramethyltin, heating, controlling the reaction end point to change the color of the initial solution to be unchanged, prolonging the reaction time for 1 hour, cooling, stopping stirring, filtering, washing, distilling and recrystallizing to obtain white powdery porous methylrhenium trioxide. In specific implementation, the amount of each component is added according to the mass unit and the parts according to the amount of a product to be prepared.
The application in alcohol deoxidation and dehydration reaction is as follows:
mixing 1 part of the synthesized porous methyl rhenium trioxide, 30 parts of toluene and 3 parts of 1, 2-octanediol in a reactor, connecting a condensing reflux device, reacting in ultrasound, heating to 40 ℃, reacting for 6 hours, stopping the reaction, cooling the system to room temperature, performing solid-liquid separation, and performing gas chromatography to obtain a reaction product with the yield of 99.0%.
Example 2:
synthesis of porous methyl rhenium trioxide:
adding 7 parts of ionic liquid 1-heptyl-3-methylimidazolium chloride salt, 2 parts of water and 20% dichloromethane into a reaction kettle, stirring and mixing uniformly at 25 ℃ under normal pressure, then adding 0.2 part of potassium perrhenate into the system, stirring for 1 hour, then adding 0.2 part of trimethylchlorosilane and 0.18 part of tetramethyltin, heating, controlling the reaction end point to change the color of the initial solution to be unchanged, prolonging the reaction time for 2 hours, cooling, stopping stirring, filtering, washing, distilling and recrystallizing to obtain white powdery porous methylrhenium trioxide.
The application in alcohol deoxidation and dehydration reaction is as follows:
mixing 1 part of the synthesized porous methyl rhenium trioxide, 30 parts of toluene and 4 parts of 1, 2-octanediol in a reactor, connecting a condensing reflux device, reacting in ultrasound, heating to 50 ℃, reacting for 5 hours, stopping the reaction, cooling the system temperature to room temperature, performing solid-liquid separation, and performing gas chromatography to obtain the reaction product with the yield of 99.5 percent.
Example 3:
synthesis of porous methyl rhenium trioxide:
adding 8 parts of ionic liquid 1-heptyl-3-methylimidazolium chloride salt, 3 parts of water and 25% dichloromethane into a reaction kettle, stirring and mixing uniformly at 25 ℃ under normal pressure, then adding 0.2 part of potassium perrhenate into the system, stirring for 1 hour, then adding 0.18 part of trimethylchlorosilane and 0.18 part of tetramethyltin, heating, controlling the reaction end point to change the color of the initial solution to be unchanged, prolonging the reaction time for 0.5 hour, cooling, stopping stirring, filtering, washing, distilling and recrystallizing to obtain white powdery porous methylrhenium trioxide.
The application in alcohol deoxidation and dehydration reaction is as follows:
mixing 1 part of the synthesized porous methyl rhenium trioxide, 30 parts of toluene and 4 parts of 1, 2-octanediol with a reactor, connecting a condensing reflux device, reacting in ultrasound, heating to 45 ℃, reacting for 4 hours, stopping the reaction, cooling to room temperature, performing solid-liquid separation, and performing gas chromatography to obtain a reaction product with the yield of 99.8%.
The present invention is not described in detail in the prior art.
Claims (7)
1. The porous methyl rhenium trioxide is characterized in that the synthesis method is as follows: adding ionic liquid, water and an auxiliary agent into a reaction kettle, stirring and mixing uniformly at the temperature of 20-40 ℃ under normal pressure, then adding potassium perrhenate into the system, stirring for 1-2 hours, then adding trimethylchlorosilane and tetramethyltin, heating, taking the color change of an initial solution as a reaction end point when the color is not changed, prolonging the reaction time for 0.5-2 hours, cooling, stopping stirring, and after the reaction is finished, filtering, washing, distilling and recrystallizing to obtain white powdery porous methyl rhenium trioxide.
2. The porous methyltrioxorhenium according to claim 1, wherein the ionic liquid is 1-heptyl-3-methylimidazolium chloride.
3. The porous methyltrioxorhenium according to claim 2, characterized in that the mass ratio of the ionic liquid to the water is (5-1): 1.
4. The porous methyltrioxorhenium according to claim 1, wherein the auxiliary agent is dichloromethane.
5. The porous methyltrioxorhenium according to claim 4, characterized in that the additive amount of the aid is 10-50%.
6. The porous methyltrioxorhenium according to claim 1, wherein the mass ratio of the ionic liquid, the potassium perrhenate, the trimethylchlorosilane to the tetramethyltin is 50: (1.5-1): (1.4-1): (1.2-1).
7. The porous methyltrioxorhenium according to claim 1, wherein the porous methyltrioxorhenium is added to an alcohol deoxygenation and dehydration reaction and is used as a catalyst for the alcohol deoxygenation and dehydration reaction.
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| CN202111473206.2A CN114315907A (en) | 2021-12-06 | 2021-12-06 | Porous methyl rhenium trioxide and application method thereof |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5929298A (en) * | 1998-07-13 | 1999-07-27 | Eastman Chemical Company | Process for preparing conjugated dienes using substituted rhenium trioxide |
| CN1733781A (en) * | 2005-09-01 | 2006-02-15 | 辽宁大学 | Methyl rhenium trioxide synthesis method |
| CN103464200A (en) * | 2013-09-22 | 2013-12-25 | 辽宁石油化工大学 | Supported perrhenate ionic liquid as well as preparation method thereof |
| CN111003713A (en) * | 2019-12-20 | 2020-04-14 | 辽宁大学 | Method for preparing inorganic porous material based on ionic liquid ternary system |
| CN111253200A (en) * | 2018-11-30 | 2020-06-09 | 中国科学院大连化学物理研究所 | Method for preparing olefin by deoxidizing and dehydrating polyhydroxy compound by using alcohol as reducing agent |
| CN111410595A (en) * | 2020-04-07 | 2020-07-14 | 辽宁大学 | Application of rhenium ionic liquid in alcohol deoxidation and dehydration reaction |
-
2021
- 2021-12-06 CN CN202111473206.2A patent/CN114315907A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5929298A (en) * | 1998-07-13 | 1999-07-27 | Eastman Chemical Company | Process for preparing conjugated dienes using substituted rhenium trioxide |
| CN1733781A (en) * | 2005-09-01 | 2006-02-15 | 辽宁大学 | Methyl rhenium trioxide synthesis method |
| CN103464200A (en) * | 2013-09-22 | 2013-12-25 | 辽宁石油化工大学 | Supported perrhenate ionic liquid as well as preparation method thereof |
| CN111253200A (en) * | 2018-11-30 | 2020-06-09 | 中国科学院大连化学物理研究所 | Method for preparing olefin by deoxidizing and dehydrating polyhydroxy compound by using alcohol as reducing agent |
| CN111003713A (en) * | 2019-12-20 | 2020-04-14 | 辽宁大学 | Method for preparing inorganic porous material based on ionic liquid ternary system |
| CN111410595A (en) * | 2020-04-07 | 2020-07-14 | 辽宁大学 | Application of rhenium ionic liquid in alcohol deoxidation and dehydration reaction |
Non-Patent Citations (3)
| Title |
|---|
| CAMILLE BOUCHER-JACOBS ET AL.: "Oxo-Rhenium-Catalyzed Deoxydehydration of Polyols with Hydroaromatic Reductants", 《ORGANOMETALLICS》, vol. 34, pages 1985 - 1990, XP093128189, DOI: 10.1021/acs.organomet.5b00226 * |
| IRSHAD AHMAD ET AL.: "Sulfite-Driven, Oxorhenium-Catalyzed Deoxydehydration of Glycols", 《ORGANOMETALLICS》, vol. 30, pages 2810 - 2818, XP055243127, DOI: 10.1021/om2001662 * |
| SAIDI VKUTURI ET AL.: "Rhenium-Catalyzed Deoxydehydration of Glycols by Sulfite", 《INORG. CHEM.》, vol. 49, pages 4744 - 4746 * |
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