CN102976896A - Method for preparing pinacol by dehydrogenation of photocatalytic isopropanol dehydrogenation and hydrogenation coupling of acetone - Google Patents
Method for preparing pinacol by dehydrogenation of photocatalytic isopropanol dehydrogenation and hydrogenation coupling of acetone Download PDFInfo
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Abstract
The invention discloses a method for preparing pinacol by dehydrogenation of photocatalytic isopropanol and hydrogenation coupling of acetone, comprising the following steps of: adding a semiconductor photocatalyst in a reaction solution which is composed of acetone, isopropanol and a solvent in a ratio of the reaction solution to the semiconductor photocatalyst of (100 to 500 ml): (0.1 to 3.5 g); magnetically stirring; illuminating at the inert atmosphere to react for 0.5-180 hours at the reaction temperature of 5-55 DEG C by dehydrogenation of photocatalytic isopropanol dehydrogenation and hydrogenation coupling of acetone; after the reaction is concluded, separating to obtain a catalyst and a solution; and distilling the solution to obtain the product, namely, pinacol. The method disclosed by the invention has the advantages of high conversion rate and good selectivity.
Description
Technical field
The present invention is a kind of photocatalytic synthesis method of tetramethyl ethylene ketone, specifically uses semiconductor light-catalyst catalysis dehydrogenation of isopropanol and acetone hydrogenation coupling to prepare the method for tetramethyl ethylene ketone under the illumination condition.
Background technology
Tetramethyl ethylene ketone claims again Pinacol; Anhydrous pineapple alcohol; Sheet alcohol; Tetramethylethylene glycol; Pinacol is a kind of important organic dibasic alcohol, is widely used in the fields such as agricultural chemicals is synthetic, rubber raw materials, organic synthesis, is the important source material of the organic intermediates such as synthetic Pinacolone, dimethylbutadiene.
Tetramethyl ethylene ketone is mainly synthetic by acetone reduction method and tetramethyl-ethylene two alcoholization methods.Acetone reduction preparation tetramethyl ethylene ketone method is to take magnesium amalgam, aluminium amalgam, sodium amalgam catalysis process or electrolysis process to make.Industrial the most frequently used preparation tetramethyl ethylene ketone method is the acetone reduction method under the magnesium amalgam catalytic condition now, and this method need to add mercury chloride, magnesium, acetone in the benzene solvent of boiling boiled 3-12 hour, and then hydrolysis forms the magnesium salts of tetramethyl ethylene ketone.The existence of water can not be arranged in this reaction system, need to carry out strict dry and distillation to acetone and benzene; Reacted mercury waste residue will carefully be processed thoroughly, and contains organomercury compound in the tetramethyl ethylene ketone hydrate that obtains of this method, and the steam of its generation is to the toxic effect of human body; Use a large amount of high carcinogenic benzene to make solvent, to operator's health generation grievous injury.Therefore, it is very high to use this method to prepare its comprehensive cost of tetramethyl ethylene ketone, is unfavorable for environmental protection.
Have for the method for using tetramethyl-ethylene two alcoholization to prepare tetramethyl ethylene ketone: use OsO
4/ oxygenant, the oxygenant here comprise the oxide compound of oxygen, hydrogen peroxide, chloric acid, Trimethylamine 99 and organic oxidation selenium etc.; After with an organic solvent method appears again not, make oxygenant as using the hydrogen persulfate aqueous solutions of potassium, perhaps do catalyzer and the common use of hydrogen peroxide etc. with highly acidic resin.But these methods or use poisonous, expensive catalyzer, or use dangerous, explosive oxygenant.After this Carlo Venturello, Noyori etc. report a kind of efficient alkene epoxidation/two alcoholization methods in succession, these methods all are with tungstate/phase-transfer catalyst system, make the hydrogen peroxide reaction of alkene and adding produce epoxide, but the problem such as the ubiquity catalyzer can't be recycled, yield is low.Chinese patent ZL200410082734.5 provides a kind of method for preparing tetramethyl ethylene ketone, and this method adopts raw material tetramethyl-ethylene and hydrogen peroxide to react under the condition of acidity and heated and stirred, and catalyzer is the complex catalyst of tungstenic or aluminium.But the method is to react under strongly-acid and strong oxidizing property condition, easily to the equipment corrosion, also have safety problem, and the tetramethyl-ethylene price is more expensive, uses its production cost as raw produce; raw products higher.
The report of relevant aromatic ketone-Isopropanol Solvent synthetic vicinal diols under the effect of photocatalyst is existing a lot, and in this system, Virahol provides the hydrogen proton to promote the coupling of aromatic ketone carbon carbon to generate vicinal diols, the oxidized generation by product of Virahol self acetone.And rarely have report about the synthetic vicinal diols of aliphatic ketone carbon carbon coupling under the effect of light.Scholar's research the photolysis of carbonyl compound under the effect of light, namely famous Norrish I type DeR refers to that light-initiated de-carbonyl reaction occurs saturated carbonyl compound in gas phase.Light activated result is: the bond rupture adjacent with carbonyl, and formation comprises the basic right of an alkyl and an acyl group, and a photodegradation that exemplary is acetone of this class reaction produces carbon monoxide in large quantities in the reaction, and other products is methane and ethane.Also have the scholar to mention about the photoprocess of acetone in the presence of isopropanol solvent, product only has a small amount of tetramethyl ethylene ketone and 2,5-hexanedione, and a large amount of CO, CH are arranged
4By product generates.
Summary of the invention
The object of the present invention is to provide a kind of transformation efficiency high, the photochemical catalysis dehydrogenation of isopropanol that selectivity is good and acetone hydrogenation coupling prepare the method for tetramethyl ethylene ketone.
Reaction mechanism of the present invention is: semiconductor catalyst is under the driving of light, and valence band produces the hole with oxidisability, and conduction band produces the electronics (reaction formula 1) with reductibility.Next hydrogen proton is taken off with isopropanol oxidation in the hole in the α position, generate Virahol free radical (reaction formula 2), electronics generates hydrogen atom with the reduction of hydrogen proton, is also generated Virahol free radical (reaction formula 3) by the utilization of acetone original position, and the coupling of Virahol free radical carbon carbon generates tetramethyl ethylene ketone (reaction formula 4).In this reaction system, the reduction hydrogenation of the dehydrogenation of photochemical catalysis isopropanol oxidation and acetone is effectively worked in coordination with, and light induced electron and hole can in time be consumed, and has greatly improved photocatalysis efficiency (transformation efficiency is 50%-90%).Simultaneously, the hydrogen proton that Virahol α takes off the position can be utilized (reaction formula 5) by the acetone original position, realizes atom economy, has effectively avoided the generation (the tetramethyl ethylene ketone selectivity is on the 75%-99%) of by product.In addition, employed catalyzer forms single, recoverable in the process.Generally speaking, the method raw material is cheap and easy to get, the catalyzer recoverable, and production cost is low, environmental friendliness and speed of reaction are fast, and transformation efficiency is high, and selectivity is good, and product is easily separated, is the technology of the synthetic tetramethyl ethylene ketone of a kind of green, efficient, atom economy.
The present invention realizes by following technology:
By reaction solution: semiconductor light-catalyst is 100-500 ml:0.1-3.5 g, semiconductor light-catalyst is joined in the reaction solution of acetone, Virahol and solvent composition, magnetic agitation, the reaction of photochemical catalysis dehydrogenation of isopropanol and acetone hydrogenation coupling preparation tetramethyl ethylene ketone is carried out in illumination under the inert atmosphere, temperature of reaction is between 5-55 ℃, and the reaction times is between 0.5-180 h, after reaction finishes, separate obtaining catalyzer and solution, solution distills and obtains the product tetramethyl ethylene ketone.
Aforesaid semiconductor light-catalyst is semi-conductor heteropolyacid salt such as H
4SiW
12O
40, H
3PW
12O
40Deng, metal oxide semiconductor such as TiO
2, WO
3, Ta
2O
5Deng, the salt of metal oxide semiconductor such as NaTiO
3, NaTaO
3, Bi
2WO
6Deng, chalcogenide semiconductor compound such as CdS or ZnS etc.
The light source of aforesaid reaction needed illumination condition can be ultraviolet lamp, xenon lamp, simulated solar irradiation or true sunlight.
Aforesaid solvent can be the mixture of water, organic solvent or water and organic solvent, and organic solvent is acetonitrile, hexanaphthene or tetrahydrofuran (THF) etc.
To between the 1:5, reactant and solvent volume are than between 1:0-10 at 5:1 for aforesaid acetone and Virahol mole proportioning.
Aforesaid separation be staticly settle, the method such as centrifugation or vacuum filtration.
The present invention compared with prior art has following advantage:
1, adopt the method for photochemical catalysis alcohol ketone dehydrogenation hydrogenation coupling to prepare tetramethyl ethylene ketone, photochemical catalysis is a kind of synthetic route of green, and the photochemical catalysis organic synthesis is carried out at normal temperatures and pressures, and is easy to operate, generally can not produce secondary pollution.
2, in this reaction system, the reduction hydrogenation of the dehydrogenation of photochemical catalysis isopropanol oxidation and acetone is effectively worked in coordination with, and light induced electron and hole can in time be consumed, and has greatly improved photocatalysis efficiency (transformation efficiency is in the 50%-90% scope).
3, the hydrogen proton taken off the position of Virahol α can be utilized by the acetone original position, realizes atom economy, has effectively avoided the generation of by product, and the tetramethyl ethylene ketone product has good selectivity (in the 75%-99% scope).
4, reactant is acetone and Virahol cheap and easy to get, can obtain the tetramethyl ethylene ketone product of high added value.
5, do not need to support the noble metal promoted agent such as Pt, catalyst component is single, is easy to separate and reclaim.
Embodiment
The present invention will be further described below by example, and its purpose only is to understand better research contents of the present invention, and unrestricted protection scope of the present invention.
Embodiment 1
With 1 g TiO
2Photocatalyst joins in the 55.5 ml acetone-19.1 ml Virahol-125.4 ml water reaction solutions, pass into argon gas under the magnetic agitation, behind the air in the eliminating system, open the 300W high voltage mercury lamp and carry out the reaction of photochemical catalysis dehydrogenation of isopropanol and acetone hydrogenation coupling preparation tetramethyl ethylene ketone, 55 ℃ of temperature of reaction, reaction times 36 h.Reaction is isolated reaction solution by staticly settling after finishing, and solution distills and obtains the product tetramethyl ethylene ketone.Stratographic analysis shows, acetone conversion 78.1%, and iso-propanol conversion rate 63.8%, tetramethyl ethylene ketone selectivity are 91.2%.
Embodiment 2
Will be through 1 g TiO behind 600 ℃ of calcining 8 h
2Photocatalyst joins in 18.5 ml acetone-19.1 ml Virahol-120 ml water-42.4ml hexanaphthene reaction solutions, pass into argon gas under the magnetic agitation, behind the air in the eliminating system, open 300 W high voltage mercury lamps and carry out the reaction of photochemical catalysis dehydrogenation of isopropanol and acetone hydrogenation coupling preparation tetramethyl ethylene ketone, 50 ℃ of temperature of reaction, reaction times 24 h.Reaction is isolated reaction solution by staticly settling after finishing, and stratographic analysis shows, acetone conversion 76.1%, and iso-propanol conversion rate 52.8%, tetramethyl ethylene ketone selectivity are 83.4%.
Embodiment 3
2.5 g sodium tantalate catalyzer of hydrothermal method preparation are joined in 50 ml acetone-50 ml Virahol-80 ml water-20ml hexanaphthene water reaction solutions, pass into argon gas under the magnetic agitation, behind the air in the eliminating system, open 500 W high voltage mercury lamps and carry out the reaction of photochemical catalysis dehydrogenation of isopropanol and acetone hydrogenation coupling preparation tetramethyl ethylene ketone, 45 ℃ of temperature of reaction, reaction times 180 h.Reaction is isolated reaction solution by staticly settling after finishing, and stratographic analysis shows, acetone conversion 93.5%, and iso-propanol conversion rate 90.7%, tetramethyl ethylene ketone selectivity are 90.8%.
Embodiment 4
3.5 g tungstic oxide catalyzer of sol-gel method preparation are joined in the 245 ml acetone-245 ml Virahol-10 ml water reaction solutions, pass into argon gas under the magnetic agitation, behind the air in the eliminating system, open 300 W high voltage mercury lamps and carry out the reaction of photochemical catalysis dehydrogenation of isopropanol and acetone hydrogenation coupling preparation tetramethyl ethylene ketone, 30 ℃ of temperature of reaction, reaction times 48 h.Reaction is isolated reaction solution by staticly settling after finishing, and stratographic analysis shows, acetone conversion 60.6%, and iso-propanol conversion rate 57.2%, tetramethyl ethylene ketone selectivity are 76.5%.
Embodiment 5
1.5 g pucherite catalyzer of hydrothermal method preparation are joined in 100 ml acetone-100 ml Virahol (solvent-free) reaction solutions, pass into argon gas under the magnetic agitation, behind the air in the eliminating system, open 300 W high voltage mercury lamps and carry out the reaction of photochemical catalysis dehydrogenation of isopropanol and acetone hydrogenation coupling preparation tetramethyl ethylene ketone, 35 ℃ of temperature of reaction, reaction times 120 h.Reaction is isolated reaction solution by staticly settling after finishing, and stratographic analysis shows, acetone conversion 61.6%, and iso-propanol conversion rate 53.4%, tetramethyl ethylene ketone selectivity are 82.7%.
Embodiment 6
3 g pucherite catalyzer of hydrothermal method preparation are joined in 300 ml acetone-100 ml Virahol-100ml water reaction solutions, pass into argon gas under the magnetic agitation, behind the air in the eliminating system, open 300 W high voltage mercury lamps and carry out the reaction of photochemical catalysis dehydrogenation of isopropanol and acetone hydrogenation coupling preparation tetramethyl ethylene ketone, 5 ℃ of temperature of reaction, reaction times 60 h.Reaction is isolated reaction solution by staticly settling after finishing, and stratographic analysis shows, acetone conversion 75.2%, and iso-propanol conversion rate 60.4%, tetramethyl ethylene ketone selectivity are 85.6%.
Embodiment 7
2 g bismuth tungstate catalyzer of hydrothermal method preparation are joined in 20 ml acetone-40 ml Virahol-120ml water-20ml acetonitrile reaction liquid, pass into argon gas under the magnetic agitation, behind the air in the eliminating system, open 500 W xenon lamps and carry out the reaction of photochemical catalysis dehydrogenation of isopropanol and acetone hydrogenation coupling preparation tetramethyl ethylene ketone, 25 ℃ of temperature of reaction, reaction times 120 h.Reaction is isolated reaction solution by staticly settling after finishing, and stratographic analysis shows, acetone conversion 61.2%, and iso-propanol conversion rate 50.3%, tetramethyl ethylene ketone selectivity are 83.4%.
Embodiment 8
2.5 g Cadmium Sulfide catalyzer of hydrothermal method preparation are joined in 60ml acetone-40 ml Virahol-100ml water reaction solution, pass into argon gas under the magnetic agitation, behind the air in the eliminating system, open 300 W xenon lamps and carry out the reaction of photochemical catalysis dehydrogenation of isopropanol and acetone hydrogenation coupling preparation tetramethyl ethylene ketone, 40 ℃ of temperature of reaction, reaction times 60 h.Reaction is isolated reaction solution by staticly settling after finishing, and stratographic analysis shows, acetone conversion 65.6%, and iso-propanol conversion rate 53.8%, tetramethyl ethylene ketone selectivity are 88.9%.
Embodiment 9
1.5 g sodium tantalate catalyzer of hydrothermal method preparation are joined in the 50 ml acetone-50 ml Virahol-80 ml water-20 ml acetonitrile reaction liquid, pass into argon gas under the magnetic agitation, behind the air in the eliminating system, open 300 W high voltage mercury lamps and carry out the reaction of photochemical catalysis dehydrogenation of isopropanol and acetone hydrogenation coupling preparation tetramethyl ethylene ketone, 10 ℃ of temperature of reaction, reaction times 24 h.Reaction is isolated reaction solution by staticly settling after finishing, and stratographic analysis shows, acetone conversion 89.2%, and iso-propanol conversion rate 81.8%, tetramethyl ethylene ketone selectivity are 92.2%.Embodiment 10
With 2.0 g H
3PW
12O
40Photocatalyst joins in 10 ml acetone-20 ml Virahol-160 ml water-10ml hexanaphthene reaction solutions, pass into argon gas under the magnetic agitation, behind the air in the eliminating system, open 300 W high voltage mercury lamps and carry out the reaction of photochemical catalysis dehydrogenation of isopropanol and acetone hydrogenation coupling preparation tetramethyl ethylene ketone, 20 ℃ of temperature of reaction, reaction times 36 h.Reaction is isolated reaction solution by staticly settling after finishing, and stratographic analysis shows, acetone conversion 70.2%, and iso-propanol conversion rate 51.8%, tetramethyl ethylene ketone selectivity are 80.3%.
Claims (10)
1. the coupling of a photochemical catalysis dehydrogenation of isopropanol and acetone hydrogenation prepares the method for tetramethyl ethylene ketone, it is characterized in that comprising the steps:
By reaction solution: semiconductor light-catalyst is 100-500 ml:0.1-3.5 g, semiconductor light-catalyst is joined in the reaction solution of acetone, Virahol and solvent composition, magnetic agitation, the reaction of photochemical catalysis dehydrogenation of isopropanol and acetone hydrogenation coupling preparation tetramethyl ethylene ketone is carried out in illumination under the inert atmosphere, temperature of reaction is between 5-55 ℃, and the reaction times is between 0.5-180 h, after reaction finishes, separate obtaining catalyzer and solution, solution distills and obtains the product tetramethyl ethylene ketone.
2. the coupling of a kind of photochemical catalysis dehydrogenation of isopropanol as claimed in claim 1 and acetone hydrogenation prepares the method for tetramethyl ethylene ketone, it is characterized in that described semiconductor light-catalyst is the semi-conductor heteropolyacid salt, metal oxide semiconductor
The salt of metal oxide semiconductor or chalcogenide semiconductor compound.
3. the coupling of a kind of photochemical catalysis dehydrogenation of isopropanol as claimed in claim 2 and acetone hydrogenation prepares the method for tetramethyl ethylene ketone, it is characterized in that described semi-conductor heteropolyacid salt is H
4SiW
12O
40Or H
3PW
12O
40
4. the coupling of a kind of photochemical catalysis dehydrogenation of isopropanol as claimed in claim 2 and acetone hydrogenation prepares the method for tetramethyl ethylene ketone, it is characterized in that described metal oxide semiconductor is TiO
2, WO
3Or Ta
2O
5
5. the coupling of a kind of photochemical catalysis dehydrogenation of isopropanol as claimed in claim 2 and acetone hydrogenation prepares the method for tetramethyl ethylene ketone, and the salt that it is characterized in that described metal oxide semiconductor is NaTiO
3, NaTaO
3Or Bi
2WO
6
6. the coupling of a kind of photochemical catalysis dehydrogenation of isopropanol as claimed in claim 2 and acetone hydrogenation prepares the method for tetramethyl ethylene ketone, it is characterized in that described chalcogenide semiconductor compound is CdS or ZnS.
7. the coupling of a kind of photochemical catalysis dehydrogenation of isopropanol as claimed in claim 1 and acetone hydrogenation prepares the method for tetramethyl ethylene ketone, and the light source that it is characterized in that described reaction needed illumination condition is ultraviolet lamp, xenon lamp, simulated solar irradiation or true sunlight.
8. the coupling of a kind of photochemical catalysis dehydrogenation of isopropanol as claimed in claim 1 and acetone hydrogenation prepares the method for tetramethyl ethylene ketone, it is characterized in that described solvent is the mixture of water, organic solvent or water and organic solvent.
9. the coupling of a kind of photochemical catalysis dehydrogenation of isopropanol as claimed in claim 8 and acetone hydrogenation prepares the method for tetramethyl ethylene ketone, it is characterized in that described organic solvent is acetonitrile, hexanaphthene or tetrahydrofuran (THF).
10. the coupling of a kind of photochemical catalysis dehydrogenation of isopropanol as claimed in claim 1 and acetone hydrogenation prepare the method for tetramethyl ethylene ketone, it is characterized in that described acetone and Virahol mole proportioning at 5:1 between the 1:5, reactant and solvent volume compare between 1:0-10.
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Cited By (6)
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| CN104478656B (en) * | 2014-11-26 | 2016-02-10 | 广西大学 | A kind of method of carbon dioxide reduction |
| CN110078579A (en) * | 2019-04-29 | 2019-08-02 | 淮北师范大学 | It is a kind of to use CO2The method for restoring difunctional photocatalysis coupled reaction preparation renewable carbon hydrogen compound |
| CN110627619A (en) * | 2019-09-30 | 2019-12-31 | 山西大学 | Preparation method of pinacol |
| CN110773169A (en) * | 2019-11-04 | 2020-02-11 | 中国科学院山西煤炭化学研究所 | Shell-like CoTiO 3Nano semiconductor photocatalyst and preparation method and application thereof |
| CN111205174A (en) * | 2020-01-22 | 2020-05-29 | 天津赫普菲乐新材料有限公司 | Photochemical reaction-based asymmetric ketone synthesis method |
| CN114618526A (en) * | 2022-02-16 | 2022-06-14 | 复旦大学 | Cadmium sulfide/platinum/sodium tantalate nanocube composite photocatalyst and preparation method and application thereof |
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| CN104478656B (en) * | 2014-11-26 | 2016-02-10 | 广西大学 | A kind of method of carbon dioxide reduction |
| CN110078579A (en) * | 2019-04-29 | 2019-08-02 | 淮北师范大学 | It is a kind of to use CO2The method for restoring difunctional photocatalysis coupled reaction preparation renewable carbon hydrogen compound |
| CN110078579B (en) * | 2019-04-29 | 2022-01-11 | 淮北师范大学 | By using CO2Method for preparing renewable hydrocarbon compound by reduction bifunctional photocatalytic coupling reaction |
| CN110627619A (en) * | 2019-09-30 | 2019-12-31 | 山西大学 | Preparation method of pinacol |
| CN110627619B (en) * | 2019-09-30 | 2021-11-19 | 山西大学 | Preparation method of pinacol |
| CN110773169A (en) * | 2019-11-04 | 2020-02-11 | 中国科学院山西煤炭化学研究所 | Shell-like CoTiO 3Nano semiconductor photocatalyst and preparation method and application thereof |
| CN110773169B (en) * | 2019-11-04 | 2021-11-19 | 中国科学院山西煤炭化学研究所 | Shell-like CoTiO3Nano semiconductor photocatalyst and preparation method and application thereof |
| CN111205174A (en) * | 2020-01-22 | 2020-05-29 | 天津赫普菲乐新材料有限公司 | Photochemical reaction-based asymmetric ketone synthesis method |
| CN114618526A (en) * | 2022-02-16 | 2022-06-14 | 复旦大学 | Cadmium sulfide/platinum/sodium tantalate nanocube composite photocatalyst and preparation method and application thereof |
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