CN102976896B - The method of tetramethyl ethylene ketone is prepared in a kind of photochemical catalysis dehydrogenation of isopropanol and acetone hydrogenation coupling - Google Patents
The method of tetramethyl ethylene ketone is prepared in a kind of photochemical catalysis dehydrogenation of isopropanol and acetone hydrogenation coupling Download PDFInfo
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Abstract
A kind of method that tetramethyl ethylene ketone is prepared in photochemical catalysis dehydrogenation of isopropanol and acetone hydrogenation coupling is by reaction solution: semiconductor light-catalyst is 100-500ml:0.1-3.5g, semiconductor light-catalyst is joined in the reaction solution of acetone, Virahol and solvent composition, magnetic agitation, under inert atmosphere, illumination carries out photochemical catalysis dehydrogenation of isopropanol and the reaction of tetramethyl ethylene ketone is prepared in acetone hydrogenation coupling, temperature of reaction is between 5-55 DEG C, reaction times is between 0.5-180h, after reaction terminates, separation obtains catalyzer and solution, and solution carries out distillation and obtains product tetramethyl ethylene ketone.It is high that the present invention has transformation efficiency, the advantage that selectivity is good.
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 illumination condition.
Background technology
Tetramethyl ethylene ketone is also known as Pinacol; Anhydrous pineapple alcohol; Gneissic suite; Tetramethylethylene glycol; Pinacol, is a kind of important organic diol, is widely used in the fields such as pesticide synthesis, rubber raw materials, organic synthesis, is the important source material of organic intermediate such as synthesis Pinacolone, dimethylbutadiene etc.
Tetramethyl ethylene ketone is primarily of acetone reduction method and the diolation method synthesis of tetramethyl-ethylene.It is take magnesium amalgam, aluminium amalgam, sodium amalgam catalysis process or electrolysis process obtained that tetramethyl ethylene ketone method is prepared in acetone reduction.On present industrial, the most frequently used tetramethyl ethylene ketone method of preparing is acetone reduction method under magnesium amalgam catalytic condition, and this method needs to add mercury chloride in the benzene solvent of boiling, magnesium, acetone boil 3-12 hour, and then hydrolysis forms the magnesium salts of tetramethyl ethylene ketone.The existence of water can not be had in this reaction system, need to carry out strict drying and distillation to acetone and benzene; Reacted mercury waste residue will carry out carefully processing thoroughly, and containing organomercury compound in the tetramethyl ethylene ketone hydrate that obtains of this method, its steam produced is to the toxic effect of human body; Use a large amount of high carcinogenic benzene to make solvent, grievous injury is produced to the health of operator.Therefore, use this method to prepare its comprehensive cost of tetramethyl ethylene ketone very high, be unfavorable for environmental protection.
The diolation method preparing tetramethyl ethylene ketone of use tetramethyl-ethylene is had: use OsO
4/ oxygenant, oxygenant here comprises the oxide compound and organic oxidation selenium etc. of oxygen, hydrogen peroxide, chloric acid, Trimethylamine 99; After there is again not method with an organic solvent, as used hydrogen persulfate aqueous solutions of potassium to make oxygenant, or make catalyzer with highly acidic resin and hydrogen peroxide uses jointly.But these methods or use poisonous, expensive catalyzer, or use dangerous, explosive oxygenant.After this Carlo Venturello, Noyori etc. report a kind of alkene epoxidation/diolation method efficiently in succession, these methods are all by tungstate/phase-transfer catalyst system, alkene and the hydrogen peroxide that adds are reacted and produces epoxide, but the problem such as ubiquity catalyzer cannot be recycled, yield is low.Chinese patent ZL200410082734.5 provides a kind of method preparing tetramethyl ethylene ketone, and this method adopts raw material tetramethyl-ethylene and hydrogen peroxide in acidity and reacts under the condition of heated and stirred, and catalyzer is the complex catalyst of tungstenic or aluminium.But the method is reacted under strongly-acid and strong oxidizing property condition, easily corrode equipment, also there is safety problem, and tetramethyl-ethylene price is more expensive, it is used to be that the production cost of raw produce is higher.
The report synthesizing vicinal diols about aromatic ketone-Isopropanol Solvent under the effect of photocatalyst is existing a lot, and in this system, Virahol provides Hydrogen Proton to promote aromatic ketone carbon carbon coupling generation vicinal diols, Virahol self oxidized generation by product acetone.And rarely have report about aliphatic ketone carbon carbon coupling synthesis vicinal diols under the effect of light.The scholar's research photolysis of carbonyl compound under the effect of light, namely famous Norrish I type DeR, refer to that light-initiated de-carbonyl reaction occurs saturated carbonyl compound in the gas phase.Light activated result is: the bond rupture adjacent with carbonyl, and form the base pair comprising an alkyl and an acyl group, an exemplary of this kind of reaction is the photodegradation of acetone, produces carbon monoxide in large quantities in reaction, and other products is methane and ethane.Also have scholar to mention about the photoprocess of acetone under isopropanol solvent exists, product only has a small amount of tetramethyl ethylene ketone and 2,5-hexanedione, has a large amount of CO, CH
4by product generates.
Summary of the invention
The object of the present invention is to provide a kind of transformation efficiency high, the method for tetramethyl ethylene ketone is prepared in the photochemical catalysis dehydrogenation of isopropanol that selectivity is good and acetone hydrogenation coupling.
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.Isopropanol oxidation is taken off next Hydrogen Proton in α position by hole, generate Virahol free radical (reaction formula 2), Hydrogen Proton reduction is generated hydrogen atom by electronics, and utilized by acetone original position and also generate Virahol free radical (reaction formula 3), 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 be consumed in time, drastically increases photocatalysis efficiency (transformation efficiency is 50%-90%).Meanwhile, the Hydrogen Proton that Virahol α takes off position can be utilized (reaction formula 5) by acetone original position, realizes atom economy, efficiently avoid the generation (tetramethyl ethylene ketone selectivity is on 75%-99%) of by product.In addition, single, the recoverable of catalyzer composition used in process.Generally speaking, the method cheaper starting materials is easy to get, catalyzer recoverable, and production cost is low, environmental friendliness and speed of reaction fast, and transformation efficiency is high, and selectivity is good, and product is easily separated, is the technology of synthesis tetramethyl ethylene ketone of a kind of green, efficient, atom economy.
The present invention is realized 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, under inert atmosphere, illumination carries out photochemical catalysis dehydrogenation of isopropanol and the reaction of tetramethyl ethylene ketone is prepared in acetone hydrogenation coupling, temperature of reaction is between 5-55 DEG C, and the reaction times, between 0.5-180 h, reacts after terminating, separation obtains catalyzer and solution, and solution carries out distillation and obtains product tetramethyl ethylene ketone.
Semiconductor light-catalyst as above is that semi-conductor heteropolyacid salt is as H
4siW
12o
40, H
3pW
12o
40deng, metal oxide semiconductor is as TiO
2, WO
3, Ta
2o
5deng the salt of, metal oxide semiconductor as NaTiO
3, NaTaO
3, Bi
2wO
6deng, semiconductor sulfide is as CdS or ZnS etc.
The light source of reaction needed illumination condition as above can be ultraviolet lamp, xenon lamp, simulated solar irradiation or true sunlight.
Solvent as above can be the mixture of water, organic solvent or water and organic solvent, and organic solvent is acetonitrile, hexanaphthene or tetrahydrofuran (THF) etc.
Acetone as above and Virahol mol ratio are between 5:1 to 1:5, and reactant and solvent volume are than between 1:0-10.
Separation as above be staticly settle, the method such as centrifugation or vacuum filtration.
The present invention compared with prior art tool has the following advantages:
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 photochemical catalysis organic synthesis is carried out at normal temperatures and pressures, 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 be consumed in time, drastically increases photocatalysis efficiency (transformation efficiency is within the scope of 50%-90%).
3, the Hydrogen Proton that Virahol α takes off position can be utilized by acetone original position, and realize atom economy, efficiently avoid the generation of by product, tetramethyl ethylene ketone product has good selectivity (within the scope of 75%-99%).
4, reactant is acetone cheap and easy to get and Virahol, 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 be separated and reclaim.
Embodiment
Below by example, the present invention will be further described, and its object is only to understand research contents of the present invention better, but not limits the scope of the invention.
Embodiment 1
By 1 g TiO
2photocatalyst joins in 55.5 ml acetone-19.1 ml Virahol-125.4 ml water reaction solutions, argon gas is passed under magnetic agitation, after air in eliminating system, open 300W high voltage mercury lamp and carry out the reaction that photochemical catalysis dehydrogenation of isopropanol and acetone hydrogenation coupling prepare tetramethyl ethylene ketone, temperature of reaction 55 DEG C, reaction times 36 h.After reaction terminates, isolate reaction solution by staticly settling, solution carries out distillation and obtains product tetramethyl ethylene ketone.Stratographic analysis shows, acetone conversion 78.1%, iso-propanol conversion rate 63.8%, and tetramethyl ethylene ketone selectivity is 91.2%.
Embodiment 2
By 1 g TiO after 600 DEG C of calcining 8 h
2photocatalyst joins in 18.5 ml acetone-19.1 ml Virahol-120 ml water-42.4ml hexanaphthene reaction solutions, argon gas is passed under magnetic agitation, after air in eliminating system, open 300 W high voltage mercury lamps and carry out photochemical catalysis dehydrogenation of isopropanol and the reaction of tetramethyl ethylene ketone is prepared in acetone hydrogenation coupling, temperature of reaction 50 DEG C, reaction times 24 h.After reaction terminates, isolate reaction solution by staticly settling, stratographic analysis shows, acetone conversion 76.1%, iso-propanol conversion rate 52.8%, and tetramethyl ethylene ketone selectivity is 83.4%.
Embodiment 3
2.5 g sodium tantalate catalyzer hydrothermal method prepared join in 50 ml acetone-50 ml Virahol-80 ml water-20ml hexanaphthene water reaction solutions, argon gas is passed under magnetic agitation, after air in eliminating system, open 500 W high voltage mercury lamps and carry out photochemical catalysis dehydrogenation of isopropanol and the reaction of tetramethyl ethylene ketone is prepared in acetone hydrogenation coupling, temperature of reaction 45 DEG C, reaction times 180 h.After reaction terminates, isolate reaction solution by staticly settling, stratographic analysis shows, acetone conversion 93.5%, iso-propanol conversion rate 90.7%, and tetramethyl ethylene ketone selectivity is 90.8%.
Embodiment 4
3.5 g tungstic oxide catalyzer sol-gel method prepared join in 245 ml acetone-245 ml Virahol-10 ml water reaction solutions, argon gas is passed under magnetic agitation, after air in eliminating system, open 300 W high voltage mercury lamps and carry out photochemical catalysis dehydrogenation of isopropanol and the reaction of tetramethyl ethylene ketone is prepared in acetone hydrogenation coupling, temperature of reaction 30 DEG C, reaction times 48 h.After reaction terminates, isolate reaction solution by staticly settling, stratographic analysis shows, acetone conversion 60.6%, iso-propanol conversion rate 57.2%, and tetramethyl ethylene ketone selectivity is 76.5%.
Embodiment 5
1.5 g pucherite catalyzer hydrothermal method prepared join in 100 ml acetone-100 ml Virahol (solvent-free) reaction solutions, argon gas is passed under magnetic agitation, after air in eliminating system, open 300 W high voltage mercury lamps and carry out photochemical catalysis dehydrogenation of isopropanol and the reaction of tetramethyl ethylene ketone is prepared in acetone hydrogenation coupling, temperature of reaction 35 DEG C, reaction times 120 h.After reaction terminates, isolate reaction solution by staticly settling, stratographic analysis shows, acetone conversion 61.6%, iso-propanol conversion rate 53.4%, and tetramethyl ethylene ketone selectivity is 82.7%.
Embodiment 6
3 g pucherite catalyzer hydrothermal method prepared join in 300 ml acetone-100 ml Virahol-100ml water reaction solutions, argon gas is passed under magnetic agitation, after air in eliminating system, open 300 W high voltage mercury lamps and carry out photochemical catalysis dehydrogenation of isopropanol and the reaction of tetramethyl ethylene ketone is prepared in acetone hydrogenation coupling, temperature of reaction 5 DEG C, reaction times 60 h.After reaction terminates, isolate reaction solution by staticly settling, stratographic analysis shows, acetone conversion 75.2%, iso-propanol conversion rate 60.4%, and tetramethyl ethylene ketone selectivity is 85.6%.
Embodiment 7
2 g bismuth tungstate catalyzer hydrothermal method prepared join in 20 ml acetone-40 ml Virahol-120ml water-20ml acetonitrile reaction liquid, argon gas is passed under magnetic agitation, after air in eliminating system, open 500 W xenon lamps and carry out photochemical catalysis dehydrogenation of isopropanol and the reaction of tetramethyl ethylene ketone is prepared in acetone hydrogenation coupling, temperature of reaction 25 DEG C, reaction times 120 h.After reaction terminates, isolate reaction solution by staticly settling, stratographic analysis shows, acetone conversion 61.2%, iso-propanol conversion rate 50.3%, and tetramethyl ethylene ketone selectivity is 83.4%.
Embodiment 8
2.5 g Cadmium Sulfide catalyzer hydrothermal method prepared join in 60ml acetone-40 ml Virahol-100ml water reaction solution, argon gas is passed under magnetic agitation, after air in eliminating system, open 300 W xenon lamps and carry out photochemical catalysis dehydrogenation of isopropanol and the reaction of tetramethyl ethylene ketone is prepared in acetone hydrogenation coupling, temperature of reaction 40 DEG C, reaction times 60 h.After reaction terminates, isolate reaction solution by staticly settling, stratographic analysis shows, acetone conversion 65.6%, iso-propanol conversion rate 53.8%, and tetramethyl ethylene ketone selectivity is 88.9%.
Embodiment 9
1.5 g sodium tantalate catalyzer hydrothermal method prepared join in 50 ml acetone-50 ml Virahol-80 ml water-20 ml acetonitrile reaction liquid, argon gas is passed under magnetic agitation, after air in eliminating system, open 300 W high voltage mercury lamps and carry out photochemical catalysis dehydrogenation of isopropanol and the reaction of tetramethyl ethylene ketone is prepared in acetone hydrogenation coupling, temperature of reaction 10 DEG C, reaction times 24 h.After reaction terminates, isolate reaction solution by staticly settling, stratographic analysis shows, acetone conversion 89.2%, iso-propanol conversion rate 81.8%, and tetramethyl ethylene ketone selectivity is 92.2%.Embodiment 10
By 2.0 g H
3pW
12o
40photocatalyst joins in 10 ml acetone-20 ml Virahol-160 ml water-10ml hexanaphthene reaction solutions, argon gas is passed under magnetic agitation, after air in eliminating system, open 300 W high voltage mercury lamps and carry out photochemical catalysis dehydrogenation of isopropanol and the reaction of tetramethyl ethylene ketone is prepared in acetone hydrogenation coupling, temperature of reaction 20 DEG C, reaction times 36 h.After reaction terminates, isolate reaction solution by staticly settling, stratographic analysis shows, acetone conversion 70.2%, iso-propanol conversion rate 51.8%, and tetramethyl ethylene ketone selectivity is 80.3%.
Claims (2)
1. a method for tetramethyl ethylene ketone is prepared in photochemical catalysis dehydrogenation of isopropanol and acetone hydrogenation coupling, 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, under inert atmosphere, illumination carries out photochemical catalysis dehydrogenation of isopropanol and the reaction of tetramethyl ethylene ketone is prepared in acetone hydrogenation coupling, temperature of reaction is between 5-55 DEG C, and the reaction times, between 0.5-180 h, reacts after terminating, separation obtains catalyzer and solution, and solution carries out distillation and obtains product tetramethyl ethylene ketone;
Described semiconductor light-catalyst is H
3pW
12o
40, TiO
2, WO
3, NaTiO
3, Bi
2wO
6or CdS;
Described acetone and Virahol mol ratio are between 5:1 to 1:5, and reactant and solvent volume, than between 1:0-10, do not comprise 0 point;
Described solvent is the mixture of water, organic solvent or water and organic solvent;
Described organic solvent is acetonitrile, hexanaphthene or tetrahydrofuran (THF).
2. the method for tetramethyl ethylene ketone is prepared in a kind of photochemical catalysis dehydrogenation of isopropanol as claimed in claim 1 and acetone hydrogenation coupling, it is characterized in that the light source of described reaction needed illumination condition is ultraviolet lamp, xenon lamp, simulated solar irradiation or true sunlight.
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| CN110627619B (en) * | 2019-09-30 | 2021-11-19 | 山西大学 | Preparation method of pinacol |
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| 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 |
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| Photochemical Reactions of Benzophenone in Alcohols;J. N. PITTSJ, et al.;《J. Am. Chem. Soc.》;19590305;第81卷;第1068-1077页 * |
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