CN107935828A - A kind of method that aromatic aldehyde is prepared by methylbenzenes high selectivity - Google Patents
A kind of method that aromatic aldehyde is prepared by methylbenzenes high selectivity Download PDFInfo
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- CN107935828A CN107935828A CN201711107229.5A CN201711107229A CN107935828A CN 107935828 A CN107935828 A CN 107935828A CN 201711107229 A CN201711107229 A CN 201711107229A CN 107935828 A CN107935828 A CN 107935828A
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
- C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
- C07C45/36—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in compounds containing six-membered aromatic rings
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Abstract
The invention discloses a kind of method that aromatic aldehyde is prepared by methylbenzenes high selectivity, methylbenzenes, catalyst system and catalyzing are mixed with solvent, react under air or oxygen atmosphere, inhibitor is additionally added in reaction system, the inhibitor is aromatic alcohol compound.The present invention provides a kind of method that aromatic aldehyde is prepared by methylbenzenes high selectivity, by adding inhibitor in the reaction system, effectively inhibits excessive oxidation of the aromatic aldehyde in catalytic oxidation process, significantly improves the selectivity of aromatic aldehyde.
Description
Technical field
The present invention relates to organic synthesis field, and in particular to a kind of to prepare aromatic aldehyde by methylbenzenes high selectivity
Method.
Background technology
Aromatic aldehyde compound is a kind of industrial chemicals with high added value, is widely used in medicine, dyestuff, spices, material
Field, the market demands such as material are huge.Such as, p-t-Butylbenzaldehyde is synthetic convallaria aldehyde (α-methyl-p-tert.-butyl phenylpropionaldehyde)
Raw material, lilial are a kind of fragrances for being widely used in the fragrance such as cloves, lily, the lily of the valley, lilac, celestial visitor, camellia, fragrance
Tenderness, fine and smooth and graceful, dosage accounts for 20% in spices.
And for example, benzaldehyde is commonly called as almond oil, is industrially using one of most important aromatic aldehyde, in medicine, essence perfume
Material, dyestuff, pesticide, Material Field are all widely used, and annual requirement is more than 100,000 tons.Available for producing phenmethylol, aniline, benzene
The products such as ketone, lauryl aldehyde, laurate, plastic additive.Annual requirement increases year by year, particularly without chlorobenzaldehyde, it is domestic into
Mouth demand is big.
For another example, P-methoxybenzal-dehyde is also known as anisic aldehyde, is colourless to weak yellow liquid under room temperature, has similar hawthorn
Smell, be present in fennel oil in nature, in acacia flos, for food and cosmetics, pharmaceutically intermediate etc. synthesizes
Raw material.
The main method for synthesizing above-mentioned aromatic aldehyde has：
Chlorinolysis：Chlorinolysis is the commercial run that tradition prepares benzaldehyde, in illumination condition Toluene and chlorine
Chlorination occurs for gas, and rear hydrolysis prepares benzaldehyde, this method technical maturity, and domestic benzaldehyde produces mainly in this way.
But this technique can generate substantial amounts of chlorine-contained wastewater, big to equipment corrosion, processing is difficult.And there are a certain amount of in product benzaldehyde
Chloride so that application of the benzaldehyde in medicine, food is limited.
Manganese dioxide method：This method is to aoxidize methylbenzenes system as under oxidant in sulfuric acid, manganese dioxide
Standby aromatic aldehyde, such easy excessive oxidation of method to aromatic acid.In addition substantial amounts of spent acid, metal salt, processing can be generated after reacting
Difficulty, effect on environment are big.
Liquid-phase air oxidation since cost is low, it is environmental-friendly the features such as it is of interest by researcher always.Specifically
Using MC (Mid-Century) catalyst, i.e. Co (OAc)2·4H2O,Mn(OAc)2, NaBr/KBr/HBr as catalyst,
Under acetic acid solvent, catalysis oxidation methylbenzenes.But this method is mainly used for industrial production aromatic acid such as benzoic acid, to hexichol
Formic acid a, dibenzoic acid etc..This is because aromatic aldehyde, under Co-Mn-Br catalyst, easy excessive oxidation generates aromatic acid, causes
The selectivity of aromatic aldehyde is relatively low, economical poor.So how to retain aromatic aldehyde with high selectivity in oxidizing process, suppress virtue
Fragrant aldehyde excessive oxidation is into researcher and enterprise's urgent problem to be solved.
At present, using methylbenzenes as substrate, in the method that aromatic aldehyde is prepared by liquid-phase air oxidation, generally adopt
With four components systems, including substrate, catalyst system and catalyzing, solvent and oxygen source.To solve the problems, such as aromatic aldehyde excessive oxidation, current solution
Certainly scheme is generally by the special composition of selection, the catalyst system and catalyzing of specific morphology, or the solvent angle that screening is special.
Chinese patent literature such as Publication No. CN 103012028A discloses one kind by methylbenzenes catalysis oxidation
The method for preparing aromatic aldehyde, it uses bromide or simple substance bromine as initiator, the manganese oxide tetrahedron molecule of carried metal component
Sieve as catalyst, using methylbenzenes as substrate, using oxygen or air as oxygen source, it is organic molten that polarity is added in reaction system
Agent.Understanding, it realizes the purpose of raising aromatic aldehyde selective by using the catalyst of special construction, but from embodiment
Data understand, the raising of target product aromatic aldehyde selective is not notable, by taking benzaldehyde as an example, selectivity be 65.1%.
And for example (selective oxidation of methylbenzenes, Hu An armies, Institutes Of Technology Of Nanjing, the doctorate opinion such as Hu An armies
Text, 20071001) it have studied Acetic Acid-Water in the mixed solvent, Co (OAc)2/Mn(OAc)2Parachlorotoluene under/KBr catalysts
Selective oxidation, research finds, within the specific limits, the raising of water content is beneficial to the raising for generating aldehyde selectivity, optimal
Under the reaction condition of change, the selectivity of 4-chloro-benzaldehyde is 66.6%.Although this method can improve generation to a certain extent
The selectivity of aldehyde, but limitation, and the presence of water can slow down the reaction speed of whole reaction system, reduce reaction conversion ratio.
The content of the invention
The present invention provides a kind of method that aromatic aldehyde is prepared by methylbenzenes high selectivity, by existing four
Inhibitor is added in component reaction system, excessive oxidation of the aromatic aldehyde in catalytic oxidation process is effectively inhibited, significantly improves
The selectivity of aromatic aldehyde.
Concrete technical scheme is as follows：
A kind of method that aromatic aldehyde is prepared by methylbenzenes high selectivity, by methylbenzenes, catalyst system and catalyzing with
Solvent mixes, and reacts under air or oxygen atmosphere, and inhibitor is additionally added in reaction system, and the inhibitor is fragrance
Alcohol compound.
Inventor is aoxidizing first by being found after a large number of experiments and a series of deep mechanism study with MC catalysts
In benzene-like compounds oxidizing process, a small amount of aromatic alcohol compound is added, can be effectively so that reacting the chemical combination for resting on aldehyde
On thing, the further substantial amounts of acid of oxidation generation is avoided.After research alcohol in detail is to oxidation of aldehydes Inhibitory Mechanism, it is proposed that
Alcohol suppresses the oxidation of aldehyde by two kinds of approach：
(1) aromatic alcohol is to metallic catalyst Co (OAc)2·4H2O,Mn(OAc)2Coordination ability be better than aromatic aldehyde, fragrance
The addition of alcohol and aromatic aldehyde competitive coordination so that leave metal salt in time after aromatic aldehyde generation, hinder the continuation oxygen of aromatic aldehyde
Change.
(2) carbonyl of aromatic alcohol and aromatic aldehyde forms effective hydrogen bond action so that among the free radical of oxidation of aldehydes formation
Body is unstable, and additionally, due to hydrogen bond, steric hindrance increase is formed, aldehyde continues oxidation and is suppressed.
Preferably, the methylbenzenes in methoxy toluene, p-tert-butyltoluene, toluene at least
It is a kind of.
Preferably, the inhibitor in butyl-benzyl alcohol, P-methoxybenzyl alcohol, phenmethylol at least
It is a kind of.
When preparing corresponding aromatic aldehyde using different substrates, used inhibitor can select then opposite with the substrate
The aromatic alcohol answered, also may be selected the aromatic alcohol of other species, but based on the principle for not introducing impurity, it is more preferably opposite with the substrate
The aromatic alcohol answered.When such as, using to methoxy toluene as substrate, preferable inhibitor is P-methoxybenzyl alcohol.
Found through experiment, above-mentioned preferable aromatic alcohol compound (phenmethylol, to butyl-benzyl alcohol, to methoxybenzene
Methanol) it is stronger to the inhibitory action of aldehyde excessive oxidation.In addition, the corresponding aromatic aldehyde of above-mentioned toluene compounds is widely used, city
Field demand is big, lacks the industrialized process for preparing of high-efficiency cleaning at present.
Preferably, with the gauge of the material of the methylbenzenes, the addition of the inhibitor for 2~
10%.Further preferably, addition is 4~8%.
Preferably, the catalyst system and catalyzing includes metallic catalyst and radical initiator；
The metallic catalyst is selected from least one of cobalt acetate, manganese acetate, acetic acid zirconium；
The radical initiator is simple substance bromine or bromide, the bromide include KBr, NaBr, HBr,
Br2CHCHBr2At least one of.
Further preferably, the metallic catalyst is cobalt acetate and manganese acetate, wherein, with the methylbenzenes
Material gauge, cobalt acetate molar percentage be 2~8%；Manganese acetate molar percentage is 1~4%.
The radical initiator is selected from KBr or NaBr, free with the gauge of the material of the methylbenzenes
The molar percentage of base initiator is 0.5~2%.
Preferably, the solvent is selected from acetic acid or ethyl acetate.
Further, the method that aromatic aldehyde is prepared by methylbenzenes high selectivity, is specially：
Catalyst is added into reaction kettle, substrate, solvent, under air or oxygen atmosphere, is pressurized to 0.1MPa-
0.5MPa, is heated to 40-70 DEG C, heat-insulation pressure keeping stirring reaction 0.5-4h.After reaction, wait reaction solution to be cooled to room temperature, put
Gas.Reaction solution removes solvent, filters out catalyst, dry recovery by vacuum distillation.Further according to the aromatic acid of generation
Amount adds a certain amount of NaOH so that aromatic acid reaction generation salt, washing remove, and rectifying obtains aromatic alcohol, aldehyde, ester.Aromatic alcohol returns
Receipts continue to apply mechanically.
Compared with prior art, the invention has the advantages that：
The present invention prepares aromatic aldehyde using liquid phase air oxidation methylbenzenes, and operating procedure is simple, air or oxygen
As oxidant, cost is low, and substrate reactions accessory substance is seldom, and effect on environment is small, and recycling is simple；
The present invention by adding a small amount of inhibitor in the reaction system, under the conditions of same conversion, the selection of aromatic aldehyde
Property can improve 15~30%, reach 80~95%, have significant industrial applications value.
Catalyst recovery of the present invention 6 times, reaction yield does not change, the unconverted recycling second of raw material
Secondary response adds primary quantity, and catalyst, solvent recovery, continues to apply mechanically reaction.
Embodiment
Below in conjunction with embodiment to further description of the present invention, but protection scope of the present invention is not limited in
This.
Embodiment 1
4.00g Co (OAc) are added into reaction kettle2·4H2O,1.39g Mn(OAc)2, 0.56g KBr, 3.94g is to uncle
Butyl phenmethylol, 59.30g p-tert-butyltoluenes, 40.00g acetic acid, is passed through air, is pressurized to 0.2Mpa, with oxygen pressurize, temperature
Degree is increased to 50 DEG C, and stirring starts clock reaction, and stir speed (S.S.) 1000r/min, after reacting 2h, stops reaction, wait reaction solution
After cooling, GC internal standard methods analysis, p-tert-butyltoluene conversion ratio is 25%, and p-t-Butylbenzaldehyde is selectively 93%, to uncle
Butylbenzoic acid is selectively 4%, and p-tert-butyl benzoic acid ethyl ester is selectively 2%.Reaction solution vacuum distillation recycling acetic acid, obtains
To 38.65g acetic acid.Filtration catalytic agent, the common 4.15g of recycling catalyst.What elemental analysis showed loss is the crystallization water of catalyst
And KBr.0.18g NaOH powder is added, is sufficiently mixed 30 minutes, is washed, separation water phase (containing sodium benzoate), organic phase (contain first
Benzene, phenmethylol, benzaldehyde, ethyl benzoate).Organic phase obtains 42.03g p-tert-butyltoluenes by rectifying, and 15.066g is to uncle
Butyl benzaldehyde, 4.13g is to butyl-benzyl alcohol, 0.41g p-tert-butyl benzoic acid ethyl esters.
Comparative example 1
4.00g Co (OAc) are added into reaction kettle2·4H2O,1.39g Mn(OAc)2, 0.56g KBr, 59.30g is to uncle
Butyl toluene, 40.00g acetic acid, is passed through air, is pressurized to 0.2Mpa, and with oxygen pressurize, temperature is increased to 50 DEG C, and stirring starts
Clock reaction, stir speed (S.S.) 1000r/min, after reacting 2h, stops reaction, and after waiting reaction solution to cool down, the analysis of GC internal standard methods is right
T-butyltoluene conversion ratio is 22%, and p-t-Butylbenzaldehyde is selectively 71%, and p-tert-butyl benzoic acid is selectively 18%,
P-tert-butyl benzoic acid ethyl ester is selectively 6%.
Contrast and embodiment 1, add substrate mole percent 6% to butyl-benzyl alcohol, after reaction, to tertiary fourth
The selectivity of benzaldehyde rises to 93% from 71%.
Embodiment 2
Catalyst recovery, the 4.15g catalyst that embodiment 1 recycles is added into reaction kettle, is supplemented addition 0.56g
Potassium bromide, 1.16g H2O.3.94g is added to butyl-benzyl alcohol, 59.30g p-tert-butyltoluenes, 40.00g acetic acid, is passed through sky
Gas, is pressurized to 0.2Mpa, and with oxygen pressurize, temperature is increased to 50 DEG C, and stirring starts clock reaction, stir speed (S.S.) 1000r/
Min, after reacting 2h, stops reaction, and after waiting reaction solution to cool down, GC internal standard methods analysis, p-tert-butyltoluene conversion ratio is 23%, right
Tert-butyl benzene formaldehyde is selectively 90%, and p-tert-butyl benzoic acid is selectively 5%, and p-tert-butyl benzoic acid ethyl ester is selectively
3%.Reaction solution vacuum distillation recycling acetic acid, obtains 38.05g acetic acid.Filtration catalytic agent, the common 4.17g of recycling catalyst.Add
0.18gNaOH powder, is sufficiently mixed 30 minutes, washing, separation water phase (containing sodium benzoate), organic phase (contain toluene, phenmethylol,
Benzaldehyde, ethyl benzoate).Organic phase obtains 44.98g p-tert-butyltoluenes by rectifying, 12.15g p-t-Butylbenzaldehydes,
4.02g is to butyl-benzyl alcohol, 0.57g p-tert-butyl benzoic acid ethyl esters.
Embodiment 3
3.00g Co (OAc) are added into reaction kettle2·4H2O,1.39g Mn(OAc)2, 0.41g NaBr, 3.31g is to first
Epoxide phenmethylol, 48.87g is to methoxy toluene, and 40.00g acetic acid, is passed through air, is pressurized to 0.2Mpa, with oxygen pressurize, temperature
Degree is increased to 50 DEG C, and stirring starts clock reaction, and stir speed (S.S.) 1000r/min, after reacting 1.5h, stops reaction, wait reaction
After liquid cooling, the analysis of GC internal standard methods, is 42% to methoxy toluene conversion ratio, and P-methoxybenzal-dehyde is selectively 85%, right
Methoxy benzoic acid is selectively 9%, and ethyl anisate is selectively 4%.Reaction solution vacuum distillation recycling acetic acid,
Obtain 38.72g acetic acid.Filtration catalytic agent, the common 2.78g of recycling catalyst.0.65gNaOH powder is added, is sufficiently mixed 30 minutes,
Washing, separation water phase (containing sodium benzoate), organic phase (containing toluene, phenmethylol, benzaldehyde, ethyl benzoate).Organic phase passes through
Rectifying obtains 27.87g to methoxy toluene, 19.42g P-methoxybenzal-dehyde, and 3.12g is to methoxyl group base phenmethylol, 1.21g pairs
Methoxy ethylbenzoate.
Comparative example 3
3.00g Co (OAc) are added into reaction kettle2·4H2O,1.39g Mn(OAc)2, 0.412g NaBr, 48.87g pairs
Methoxy toluene, 40.00g acetic acid, is passed through air, is pressurized to 0.2Mpa, and with oxygen pressurize, temperature is increased to 50 DEG C, and stirring is opened
Beginning clock reaction, stir speed (S.S.) 1000r/min, after reacting 1.5h, stops reaction, after waiting reaction solution to cool down, GC internal standard methods point
Analysis, is 40% to methoxy toluene conversion ratio, and P-methoxybenzal-dehyde is selectively 62%, and P-methoxybenzoic acid is selectively
23%, ethyl anisate is selectively 8%.
Comparative example 3, adds the P-methoxybenzyl alcohol of substrate mole percent 6%, can effectively suppress in reaction
The excessive oxidation of P-methoxybenzal-dehyde, the selectivity of P-methoxybenzal-dehyde rise to 85% by 62%.
Embodiment 4
2.00g Co (OAc) are added into reaction kettle2·4H2O,1.39g Mn(OAc)2, 0.28g KBr, 3.14g benzene first
Alcohol, 36.80g toluene, 40.00g acetic acid, is passed through air, is pressurized to 0.2Mpa, and with oxygen pressurize, temperature is increased to 50 DEG C, stirring
Start clock reaction, stir speed (S.S.) 1000r/min, after reacting 2h, stops reaction, after waiting reaction solution to cool down, be evaporated under reduced pressure back
Acetic acid is received, obtains 38.72g acetic acid.Filtration catalytic agent, recycles the common 2.77g of catalyst, have lost 0.9g.Add 0.78gNaOH powder
End, is sufficiently mixed 30 minutes, and washing, separation water phase (containing sodium benzoate), organic phase (contain toluene, phenmethylol, benzaldehyde, benzene first
Acetoacetic ester).24.13g toluene, 9.89g benzaldehydes, 3.17g phenmethylols, 1.26g ethyl benzoates are obtained by rectifying.Conversion ratio
For 38%, benzaldehyde selectivity 71%, benzoic acid selectivity 19%, ethyl benzoate selectivity 4%.
Comparative example 4
2.00g Co (OAc) are added into reaction kettle2·4H2O,1.39g Mn(OAc)2, 0.28g KBr, 36.80g first
Benzene, 40.00g acetic acid, is passed through air, is pressurized to 0.2Mpa, and with oxygen pressurize, temperature is increased to 50 DEG C, and it is anti-that stirring starts timing
Should, stir speed (S.S.) 1000r/min, after reacting 2h, stops reaction, it is 41% that GC internal standard methods, which measure toluene conversion, benzaldehyde
Selectivity is 23%, and benzoic acid is selectively 61%, and ethyl benzoate is selectively 5%.
Compared with implementation column 4, after the phenmethylol for adding molar fraction 7.5%, toluene conversion is basically unchanged, benzaldehyde choosing
Selecting property brings up to 71% from 23%.Illustrate that phenmethylol can effectively inhibit benzaldehyde excessive oxidation in the reaction.
Embodiment 5
8.00g Co (OAc) are added into reaction kettle2·4H2O, 2.78g Mn (OAc)2, 0.56g KBr, 2.27g is to chlorine
Phenmethylol, 50.40g parachlorotoluenes, 40.00g acetic acid, is passed through air, is pressurized to 0.2Mpa, and with oxygen pressurize, temperature is increased to
50 DEG C, stirring starts clock reaction, and stir speed (S.S.) 1000r/min, after reacting 2h, stops reaction, after waiting reaction solution to cool down, subtract
Pressure is distilled to recover acetic acid, obtains 37.98g acetic acid.Filtration catalytic agent, recycles the common 8.41g of catalyst, have lost 2.93g.Add
0.08g NaOH powder, is sufficiently mixed 30 minutes, washing, and separation water phase (containing Sodium P-Chlorobenzoate), organic phase (contain to chloromethane
Benzene, to chlorobenzene methanol, 4-chloro-benzaldehyde, Ethoforme).43.11g parachlorotoluenes are obtained by rectifying, 6.12g is to chlorine
Benzaldehyde, 2.23g is to chlorobenzene methanol, 0.34g Ethoformes.Conversion ratio is 12%, 4-chloro-benzaldehyde selectivity 91%,
Parachlorobenzoic-acid selectivity 4%, Ethoforme selectivity 4%.
Comparative example 5
8.00g Co (OAc) are added into reaction kettle2·4H2O, 2.78g Mn (OAc)2, 0.56g KBr, 50.40g is to chlorine
Toluene, 40.00g acetic acid, is passed through air, is pressurized to 0.2Mpa, and with oxygen pressurize, temperature is increased to 50 DEG C, and stirring starts timing
Reaction, stir speed (S.S.) 1000r/min, after reacting 2h, stops reaction, after waiting reaction solution to cool down, GC detection parachlorotoluene conversions
Rate is 14%, and 4-chloro-benzaldehyde is selectively 81%, and parachlorobenzoic-acid is selectively 9%, the selectivity of Ethoforme
5%.
Compared with implementation column 5, addition molar fraction 0.4% to chlorobenzene methanol after, parachlorotoluene is in a slight decrease, to chlorobenzene
Formaldehyde selectivity brings up to 91% from 81%.Illustrate that chlorobenzene methanol can be effectively inhibited benzaldehyde excessive oxygen in the reaction
Change.Yet with parachlorotoluene, 4-chloro-benzaldehyde oxidation rate is slower, adds and is not so good as embodiment 1-4 to chlorobenzene methanol effect.
Claims (9)
1. a kind of method that aromatic aldehyde is prepared by methylbenzenes high selectivity, by methylbenzenes, catalyst system and catalyzing with it is molten
Agent mixes, and reacts under air or oxygen atmosphere, it is characterised in that inhibitor, the suppression are additionally added in reaction system
Preparation is aromatic alcohol compound.
2. the method according to claim 1 that aromatic aldehyde is prepared by methylbenzenes high selectivity, it is characterised in that institute
The methylbenzenes stated are selected at least one of methoxy toluene, p-tert-butyltoluene, toluene.
3. the method according to claim 1 or 2 that aromatic aldehyde is prepared by methylbenzenes high selectivity, its feature exist
In the inhibitor is selected at least one of butyl-benzyl alcohol, P-methoxybenzyl alcohol, phenmethylol.
4. the method according to claim 3 that aromatic aldehyde is prepared by methylbenzenes high selectivity, it is characterised in that with
The gauge of the material of the methylbenzenes, the molar percentage of inhibitor is 2~10%.
5. the method according to claim 1 that aromatic aldehyde is prepared by methylbenzenes high selectivity, it is characterised in that institute
The catalyst system and catalyzing stated includes metallic catalyst and radical initiator；
The metallic catalyst is selected from least one of cobalt acetate, manganese acetate, acetic acid zirconium；
The radical initiator is simple substance bromine or bromide.
6. the method according to claim 5 that aromatic aldehyde is prepared by methylbenzenes high selectivity, it is characterised in that institute
The metallic catalyst stated is cobalt acetate and manganese acetate, and radical initiator is selected from KBr, NaBr, HBr or tetrabromoethane；
With the gauge of the material of methylbenzenes, cobalt acetate molar percentage is 2~8%；Manganese acetate molar percentage for 1~
4%；Initiator molar percentage is 0.5~2%.
7. the method according to claim 1 that aromatic aldehyde is prepared by methylbenzenes high selectivity, it is characterised in that institute
The solvent stated is selected from acetic acid or ethyl acetate.
8. the method according to claim 1 that aromatic aldehyde is prepared by methylbenzenes high selectivity, it is characterised in that institute
The reaction stated, pressure are 0.1~0.5MPa, and temperature is 40~80 DEG C.
9. the method according to claim 1 that aromatic aldehyde is prepared by methylbenzenes high selectivity, it is characterised in that anti-
Post-treated again, isolated aromatic aldehyde, aromatic alcohol and catalyst after answering；
The aromatic alcohol and catalyst can be applied mechanically.
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| CN112047822A (en) * | 2020-07-27 | 2020-12-08 | 南京延长反应技术研究院有限公司 | Reaction system and method for preparing halogenated benzaldehyde by oxidizing halogenated toluene |
| CN114621064A (en) * | 2020-12-10 | 2022-06-14 | 中国科学院大连化学物理研究所 | Method for preparing aromatic aldehyde |
| CN116283518A (en) * | 2023-03-07 | 2023-06-23 | 中国石油大学(华东) | Method for preparing aldehyde ketone compound by one-step dichlorination and hydrolysis |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112047823A (en) * | 2020-07-27 | 2020-12-08 | 南京延长反应技术研究院有限公司 | Preparation system and method of halogenated benzaldehyde |
| CN112047822A (en) * | 2020-07-27 | 2020-12-08 | 南京延长反应技术研究院有限公司 | Reaction system and method for preparing halogenated benzaldehyde by oxidizing halogenated toluene |
| CN114621064A (en) * | 2020-12-10 | 2022-06-14 | 中国科学院大连化学物理研究所 | Method for preparing aromatic aldehyde |
| CN114621064B (en) * | 2020-12-10 | 2023-04-07 | 中国科学院大连化学物理研究所 | Method for preparing aromatic aldehyde |
| CN116283518A (en) * | 2023-03-07 | 2023-06-23 | 中国石油大学(华东) | Method for preparing aldehyde ketone compound by one-step dichlorination and hydrolysis |
| CN116283518B (en) * | 2023-03-07 | 2024-06-04 | 中国石油大学(华东) | Method for preparing aldehyde ketone compound by one-step dichlorination and hydrolysis |
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