CN102516052A - Method for preparing acetophenone through ethyl benzene oxidation by using microchannel reactor - Google Patents
Method for preparing acetophenone through ethyl benzene oxidation by using microchannel reactor Download PDFInfo
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- CN102516052A CN102516052A CN2011103467873A CN201110346787A CN102516052A CN 102516052 A CN102516052 A CN 102516052A CN 2011103467873 A CN2011103467873 A CN 2011103467873A CN 201110346787 A CN201110346787 A CN 201110346787A CN 102516052 A CN102516052 A CN 102516052A
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Abstract
The invention relates to a method for preparing acetophenone through ethyl benzene oxidation by using a microchannel reactor, and belongs to the technical field of organic synthesis application. The method of the present invention is a new process, wherein ethyl benzene is adopted as a raw material, hydrogen peroxide is adopted as an oxidant, a commonly used solvent is adopted, a cobalt salt is adopted as a catalyst, and the acetophenone is synthesized within a reaction time of tens of seconds to a few minutes in a Corning microchannel reactor. The two reaction materials are pumped into the Corning microchannel reactor through metering pumps, and then are subjected to preheating, and reacting to finally obtain the oxidation product acetophenone. According to the present invention, the operation of the method is simple; the high yield and the continuity production of the acetophenone can be achieved; the environmental pollution of the process is low; the ethyl benzene conversion rate is 20-80%, and the acetophenone selectivity is 90-100%.
Description
Technical field
The invention belongs to the organic synthesis applied technical field; Be specifically related to a kind of method for preparing methyl phenyl ketone with ethylbenzene for the raw material oxidation; In Corning (healthy and free from worry) micro passage reaction of saying so more specifically, utilize hydrogen peroxide oxidation ethylbenzene to prepare the technology of methyl phenyl ketone in high-throughput microchannel even flow.
Background technology
Methyl phenyl ketone is a kind of important chemical material, also is the midbody of synthetic other spices, and mainly as solvent, organic synthesis, olefin polymerization catalysis, dissolving power is similar with pimelinketone.Methyl phenyl ketone mainly as the raw material of pharmacy and other organic syntheses, also is used to prepare spices, perfumed soap and cigarette, also can be used as ether of cellulose, the solvent of cellulose ester and resin etc. and the softening agent of plastics.
At present, the normal ethylbenzene atmospheric oxidation legal system methyl phenyl ketone that adopts in the industry.Methyl phenyl ketone can be made by benzene and Acetyl Chloride 98Min., acetic anhydride or acetic acidreaction under aluminum chloride catalysis.The working method of methyl phenyl ketone has benzene and acetic anhydride acidylate method, benzene and excess acetyl chloride method, ethylbenzene heterogeneous oxidation method.
Up to now; Shang Weijian carries out the research of the synthetic methyl phenyl ketone of ethylbenzene liquid phase catalytic oxidation with the mode of Corning microchannel even flow, and the present invention provides a kind of operational path that in the Corning micro passage reaction, prepares methyl phenyl ketone with the mode oxidation ethylbenzene of even flow.
Carry out synthetic reaction condition when screening in early stage in the Corning micro passage reaction; Need the reactant consumption very little; Not only can reduce the consumption of costliness, poisonous, adverse reaction thing; The environmental pollutant that produce in the reaction process are also few, and the laboratory is pollution-free basically, are the technology platforms of a kind of environmental friendliness, study on the synthesis novel substance.Corning in micro passage reaction, obtain product and modern age analytical instrument; Carry out The matching analysis like GC, GC-MS, HPLC and NMR; Make the modern age analytical instrument can be used for the degree that the direct-on-line monitoring reaction carries out, improved the speed of research synthetic route greatly.
The type of the special glass functional module of Corning micro passage reaction has the straight channel type, heart type hybrid junctions configuration, have to connect the straight channel type behind one section heart type mixed structure, have connect behind one section kapillary mixed structure the straight channel type etc.The special glass functional module of Corning micro passage reaction has the functional module of two opening for feed list discharge ports and the functional module of single opening for feed and single discharge port.Its safety operation TR of Corning micro passage reaction is-25 ℃ ~ 200 ℃, and the safe working pressure scope is 0 ~ 18bar, and the material pipeline is connected to PFA (perfluoroalkoxy resin) material.European patent WO2010/037012A2; It is the module patent of Corning company special construction design; Write out the structure of the special module of Corning production in the patent in detail; Integrated and the microminiaturized selection that is the chemical process amplification than safety of module has been pointed out in the size of module and arrangement of passage or the like.
Summary of the invention
The purpose of this invention is to provide and a kind ofly in the continuous flow reactor of Corning high-throughput microchannel, carry out ethylbenzene oxidation and prepare methyl phenyl ketone; Compare with existing processes; This technology has reaction conditions accurately to be controlled, and reduces the discharging of organic liquid waste, and the successive mode is produced; And conversion of ethylbenzene is very high in the extremely short time, and the methyl phenyl ketone selectivity improves a lot.
A kind of method of utilizing micro passage reaction oxidation ethylbenzene to prepare methyl phenyl ketone of the present invention, carry out according to following step:
(1) preparation of raw material: at room temperature, with catalyzer, promotor and material ethylbenzene are dissolved in the solvent, under constantly stirring, material ethylbenzene are processed homogeneous phase solution;
(2) the even flow micro passage reaction that is adopted in the reaction process; The homogeneous phase solution of material ethylbenzene and oxygenant are squeezed into micro passage reaction through volume pump according to a certain percentage, and two strands of materials contact in the microchannel and hybrid reaction; After the residence time was 50 seconds, product obtained through overcooling.
Wherein temperature of reaction is 20～140 ℃, preferred 40～130 ℃;
Wherein the volume ratio of solvent and material ethylbenzene is 1:1 ~ 10:1 in the charging, preferred 3:1 ~ 8:1, and Glacial acetic acid min. 99.5 is a solvent;
The mol ratio of ydrogen peroxide 50 and material ethylbenzene is 1:1 ~ 12:1, preferred 1.2:1 ~ 10:1;
Wherein catalyzer is NSC 51149 or Cobaltous diacetate, preferred Cobaltous diacetate; Potassium Bromide is a promotor, and catalyzer and ethylbenzene mol ratio are 3% ~ 15%, preferred 5% ~ 14%; The volumetric concentration scope of ydrogen peroxide 50 is 27% ~ 85%, preferred 30% ~ 85%; The mol ratio of promotor Potassium Bromide is counted 1.0:1 ~ 1.97:1 with Br/Co, preferred 1.5:1 ~ 1.9:1.
To the deficiency of prior art, toxic side effect is big, and environmental pollution is serious, and the methyl phenyl ketone yield is not very high shortcoming.The ethylbenzene oxidation that in the Corning micro passage reaction, carries out even flow provided by the invention prepares the method for methyl phenyl ketone; The present invention is raw material with ethylbenzene; Ydrogen peroxide 50 is an oxygenant, is mixed with two strands of raw materials respectively, squeezes into the Corning micro passage reaction through volume pump.Material ethylbenzene is squeezed into Corning high-throughput microchannel continuous flow reactor through volume pump.Equally; Oxidant hydrogen peroxide is squeezed into Corning high channel microchannel continuous flow reactor through volume pump; The Corning micro passage reaction reaches the required temperature of reaction through the accurate control reaction temperature of interchanger through regulating interchanger, and the actual temperature of reaction records through thermopair.In oxidation reaction process; Through the mol ratio that the flow of regulating volume pump is regulated raw material and oxygenant, raw material is behind process tensimeter, SV, vacuum breaker, and the pressure in the reaction system records through the tensimeter monitoring; The SV guard reactor is continuous production under certain safe pressure; Raw material carries out preheating respectively earlier in micro passage reaction, hybrid reaction is connected to back pressure valve at reactor outlet reactor drum is remained under certain pressure condition then; Through tens seconds to the residence time of several minutes, obtain the oxidation products methyl phenyl ketone at discharge port.
The present invention has following principal feature compared with prior art:
1. the present invention adopts the Corning microchannel continuous flow reactor of even flow, and the reaction times shortened to tens seconds to several minutes from traditional several hours, had significantly improved reaction efficiency.
2. raw material and catalyzer and promotor are mixed splendidly in the microchannel, and temperature is accurately controlled, and reacts no back-mixing.
3. to have adopted ydrogen peroxide 50 be oxygenant in the present invention, in micro passage reaction, improved the selectivity of reaction, and environmentally safe.
Description of drawings
Fig. 1 prepares methyl phenyl ketone reaction process flow process schema for ethylbenzene oxidation of the present invention;
Fig. 2 is Corning micro passage reaction module used in the present invention and structure iron,
1-straight channel functional module wherein, 2-" heart type " structure function module, 3-" heart type " structural representation;
Fig. 3 is a Corning micro passage reaction schematic flow sheet used in the present invention, 1, the 2-head tank, 3, the 4-feedstock pump, 5, the 6-stopping valve, and the 7-tensimeter, the 8-corning microchannel, the 9-raw material is collected.
Embodiment
Through embodiment the present invention is done nearly step explanation below, do not hold but therefore do not limit of the present invention type.
Embodiment
1, preparation of raw material: take by weighing the 10.2Kg Cobaltous diacetate; Be poured in the glacial acetic acid container that 100L is housed, stirring is dissolved it fully, measures 100L ethylbenzene and is poured in the container; Stir; Take by weighing 4.87KgKBr adding less water again and make its dissolving fully earlier, consoluet KBr solution is poured in the mixing solutions, seal after stirring makes solution be homogeneous phase.Measure 1000L30%H again
2O
2Be placed in another container sealing.
2, be that its channel characteristics is of a size of 4mm in the straight type microchannel (shown in Figure 2) of special glass in material.Utilize Fig. 3 setting drawing of the present invention, according to subordinate's step: the glacial acetic acid solution that contains ethylbenzene in (1) head tank 1 gets into micro passage reactions 8 through pump 3, and the oxidant hydrogen peroxide in the head tank 2 gets into micro passage reactions 8 through pump 4.(2) adopt the even flow micro passage reaction in the reaction process, the homogeneous phase solution of material ethylbenzene and oxygenant are squeezed into micro passage reaction 8 according to above ratio through volume pump, are 40 ℃ of following hybrid reactions in the temperature of setting.(3) residence time of controlling reaction mass through the flow of regulating pump is 20s, two strands of materials hybrid reaction in reaction module; (4) coming the pressure of monitoring reaction system through tensimeter 7 on the reaction channel is 4bar, prevents the refluence of material through stopping valve 5 and 6; (5) after through microchannel 8 hybrid reactions, the continuous discharging of oxidation products is collected in the sampling jug 9, and product is analyzed through GC.
3, contain methyl phenyl ketone product and unreacted ethylbenzene in the reaction product.Conversion process transformation efficiency is 30.5% (GC analytical results), methyl phenyl ketone selectivity 90.4 % (GC analytical results).
1, preparation of raw material: take by weighing the 15Kg NSC 51149; Be poured in the glacial acetic acid container that 300L is housed, stirring is dissolved it fully, measures 100L ethylbenzene and is poured in the container; Stir; Take by weighing 8.6KgKBr adding less water again and make its dissolving fully earlier, consoluet KBr solution is poured in the mixing solutions, seal after stirring makes solution be homogeneous phase.Measure 1000L30%H again
2O
2Be placed in another container sealing.
2, be that its channel characteristics is of a size of 4mm in the type microchannel (shown in Figure 2) of special glass in material.With reference to Fig. 1 technical process of the present invention; Utilize the setting drawing of Fig. 3; According to subordinate's step: the glacial acetic acid solution of the ethylbenzene in (1) head tank 1 gets into micro passage reactions 8 through pump 3, and the oxidant hydrogen peroxide in the head tank 2 gets into micro passage reactions 8 through pump 4.(2) adopt the even flow micro passage reaction in the reaction process, the homogeneous phase solution of material ethylbenzene and oxygenant are squeezed into micro passage reaction 8 according to above ratio through volume pump, are 60 ℃ of following hybrid reactions in the temperature of setting.(3) residence time of controlling reaction mass through the flow of regulating pump is 30s, two strands of materials hybrid reaction in reaction module; (4) coming the pressure of monitoring reaction system through tensimeter 7 on the reaction channel is 3bar, prevents the refluence of material through stopping valve 5 and 6; (5) after through microchannel 8 hybrid reactions, the continuous discharging of oxidation products is collected in the sampling jug 9, and product is analyzed through GC.
3, contain methyl phenyl ketone product and unreacted ethylbenzene in the reaction product.Conversion process transformation efficiency is 47% (GC analytical results), methyl phenyl ketone selectivity 89.1 % (GC analytical results).
1, preparation of raw material: take by weighing the 15Kg Cobaltous diacetate; Be poured in the glacial acetic acid container that 500L is housed, stirring is dissolved it fully, measures 100L ethylbenzene and is poured in the container; Stir; Take by weighing 10.03KgNaBr adding less water again and make its dissolving fully earlier, consoluet NaBr solution is poured in the mixing solutions, seal after stirring makes solution be homogeneous phase.Measure 1000L30%H again
2O
2Be placed in another container sealing.
2, be (shown in Figure 2) in the ceramic core microchannel in material, its channel characteristics is of a size of 8mm.With reference to Fig. 1 technical process of the present invention; Utilize the setting drawing of Fig. 3; According to subordinate's step: the glacial acetic acid solution of the ethylbenzene in (1) head tank 1 gets into micro passage reactions 8 through pump 3, and the oxidant hydrogen peroxide in the head tank 2 gets into micro passage reactions 8 through pump 4.(2) adopt the even flow micro passage reaction in the reaction process, the homogeneous phase solution of material ethylbenzene and oxygenant are squeezed into micro passage reaction 8 according to above ratio through volume pump, are 80 ℃ of following hybrid reactions in the temperature of setting.(3) residence time of controlling reaction mass through the flow of regulating pump is 50s, two strands of materials hybrid reaction in reaction module; (4) coming the pressure of monitoring reaction system through tensimeter 7 on the reaction channel is 5bar, prevents the refluence of material through stopping valve 5 and 6; (5) after through microchannel 8 hybrid reactions, the continuous discharging of oxidation products is collected in the sampling jug 9, and product is analyzed through GC.
3, contain methyl phenyl ketone product and unreacted ethylbenzene in the reaction product.Conversion process transformation efficiency is 55% (GC analytical results), methyl phenyl ketone selectivity 94.5 % (GC analytical results).
Embodiment 4
1, preparation of raw material: take by weighing the 15Kg NSC 51149; Be poured in the glacial acetic acid container that 700L is housed, stirring is dissolved it fully, measures 100L ethylbenzene and is poured in the container; Stir; Take by weighing 11.46KgKBr adding less water again and make its dissolving fully earlier, consoluet KBr solution is poured in the mixing solutions, seal after stirring makes solution be homogeneous phase.Measure 1000L30%H again
2O
2Be placed in another container sealing.
2, be that its channel characteristics is of a size of 0.2mm in the heart type microchannel (shown in Figure 2) of special glass in material.With reference to Fig. 3 technical process of the present invention; Utilize the setting drawing of Fig. 3; According to subordinate's step: the glacial acetic acid solution of the ethylbenzene in (1) head tank 1 gets into micro passage reactions 8 through pump 3, and the oxidant hydrogen peroxide in the head tank 2 gets into micro passage reactions 8 through pump 4.(2) adopt the even flow micro passage reaction in the reaction process, the homogeneous phase solution of material ethylbenzene and oxygenant are squeezed into micro passage reaction 8 according to above ratio through volume pump, are 100 ℃ of following hybrid reactions in the temperature of setting.(3) residence time of controlling reaction mass through the flow of regulating pump is 70s, two strands of materials hybrid reaction in reaction module; (4) coming the pressure of monitoring reaction system through tensimeter 7 on the reaction channel is 6bar, prevents the refluence of material through stopping valve 5 and 6; (5) after through microchannel 8 hybrid reactions, the continuous discharging of oxidation products is collected in the sampling jug 9, and product is analyzed through GC.
3, contain methyl phenyl ketone product and unreacted ethylbenzene in the reaction product.Conversion process transformation efficiency is 67% (GC analytical results), methyl phenyl ketone selectivity 92.4 % (GC analytical results).
Embodiment 5
1, preparation of raw material: take by weighing the 18Kg Cobaltous diacetate; Be poured in the glacial acetic acid container that 800L is housed, stirring is dissolved it fully, measures 100L ethylbenzene and is poured in the container; Stir; Take by weighing 12.89KgNaBr adding less water again and make its dissolving fully earlier, consoluet NaBr solution is poured in the mixing solutions, seal after stirring makes solution be homogeneous phase.Measure 1000L30%H again
2O
2Be placed in another container sealing.
2, be that its channel characteristics is of a size of 0.2mm in the heart type microchannel (shown in Figure 2) of special glass in material.With reference to Fig. 3 technical process of the present invention; Utilize the setting drawing of Fig. 3; According to subordinate's step: the glacial acetic acid solution of the ethylbenzene in (1) head tank 1 gets into micro passage reactions 8 through pump 3, and the oxidant hydrogen peroxide in the head tank 2 gets into micro passage reactions 8 through pump 4.(2) adopt the even flow micro passage reaction in the reaction process, the homogeneous phase solution of material ethylbenzene and oxygenant are squeezed into micro passage reaction 8 according to above ratio through volume pump, are 110 ℃ of following hybrid reactions in the temperature of setting.(3) residence time of controlling reaction mass through the flow of regulating pump is 80s, two strands of materials hybrid reaction in reaction module; (4) coming the pressure of monitoring reaction system through tensimeter 7 on the reaction channel is 7bar, prevents the refluence of material through stopping valve 5 and 6; (5) after through microchannel 8 hybrid reactions, the continuous discharging of oxidation products is collected in the sampling jug 9, and product is analyzed through GC.
3, contain methyl phenyl ketone product and unreacted ethylbenzene in the reaction product.Conversion process transformation efficiency is 78% (GC analytical results), methyl phenyl ketone selectivity 98.3 % (GC analytical results).
Embodiment 6
1, preparation of raw material: take by weighing the 23Kg Cobaltous diacetate; Be poured in the glacial acetic acid container that 1000L is housed, stirring is dissolved it fully, measures 100L ethylbenzene and is poured in the container; Stir; Take by weighing 20.9KgKBr adding less water again and make its dissolving fully earlier, consoluet KBr solution is poured in the mixing solutions, seal after stirring makes solution be homogeneous phase.Measure 1000L30%H again
2O
2Be placed in another container sealing.
2, be that its channel characteristics is of a size of 0.2mm in the heart type microchannel (shown in Figure 2) of special glass in material.With reference to Fig. 3 technical process of the present invention; Utilize the setting drawing of Fig. 3; According to subordinate's step: the glacial acetic acid solution of the ethylbenzene in (1) head tank 1 gets into micro passage reactions 8 through pump 3, and the oxidant hydrogen peroxide in the head tank 2 gets into micro passage reactions 8 through pump 4.(2) adopt the even flow micro passage reaction in the reaction process, the homogeneous phase solution of material ethylbenzene and oxygenant are squeezed into micro passage reaction 8 according to above ratio through volume pump, are 130 ℃ of following hybrid reactions in the temperature of setting.(3) residence time of controlling reaction mass through the flow of regulating pump is 90s, two strands of materials hybrid reaction in reaction module; (4) coming the pressure of monitoring reaction system through tensimeter 7 on the reaction channel is 7bar, prevents the refluence of material through stopping valve 5 and 6; (5) after through microchannel 8 hybrid reactions, the continuous discharging of oxidation products is collected in the sampling jug 9, and product is analyzed through GC.
3, contain methyl phenyl ketone product and unreacted ethylbenzene in the reaction product.Conversion process transformation efficiency is 80.7% (GC analytical results), methyl phenyl ketone selectivity 100 % (GC analytical results).
Claims (3)
1. method of utilizing micro passage reaction oxidation ethylbenzene to prepare methyl phenyl ketone is characterized in that carrying out according to following step:
(1) preparation of raw material: at room temperature, with catalyzer, promotor and material ethylbenzene are dissolved in the solvent, under constantly stirring, material ethylbenzene are processed homogeneous phase solution;
(2) the even flow micro passage reaction that is adopted in the reaction process; The homogeneous phase solution of material ethylbenzene and oxygenant are squeezed into micro passage reaction through volume pump according to a certain percentage, and two strands of materials carry out oxidizing reaction through after the preheating respectively; After the residence time was 50 seconds, product obtained through overcooling.
2. a kind of method of utilizing micro passage reaction oxidation ethylbenzene to prepare methyl phenyl ketone according to claim 1 is characterized in that wherein temperature of reaction is 20～140 ℃,
Wherein the volume ratio of solvent and material ethylbenzene is 1:1 ~ 10:1 in the charging,
Glacial acetic acid min. 99.5 is a solvent;
The mol ratio of ydrogen peroxide 50 and material ethylbenzene is 1:1 ~ 12:1,
Wherein catalyzer is NSC 51149 or Cobaltous diacetate, and Potassium Bromide is a promotor, and catalyzer and ethylbenzene mol ratio are 3% ~ 15%, and the volumetric concentration scope of ydrogen peroxide 50 is 27% ~ 85%, and the mol ratio of promotor Potassium Bromide is counted 1.0:1 ~ 1.97:1 with Br/Co.
3. a kind of method of utilizing micro passage reaction oxidation ethylbenzene to prepare methyl phenyl ketone according to claim 2 is characterized in that wherein temperature of reaction is 40～130 ℃;
Wherein the volume ratio of solvent and material ethylbenzene is 3:1 ~ 8:1 in the charging, and the mol ratio of ydrogen peroxide 50 and material ethylbenzene is 1 1.2:1 ~ 10:1;
Wherein catalyzer is a Cobaltous diacetate; Catalyzer and ethylbenzene mol ratio are 5% ~ 14%; The volumetric concentration scope of ydrogen peroxide 50 is 30% ~ 85%; The mol ratio of promotor Potassium Bromide is counted 1.5:1 ~ 1.9:1 with Br/Co.
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106631727A (en) * | 2016-11-07 | 2017-05-10 | 常州大学 | Method for preparing 2,5-difluorobenzaldehyde through continuous oxidation of 2,5-difluorotoluene |
| CN106631728A (en) * | 2016-11-07 | 2017-05-10 | 常州大学 | Method for preparing 3,5-difluorobenzaldehyde by 3,5-difluorotoluene continuous oxidation |
| CN106699526A (en) * | 2016-11-07 | 2017-05-24 | 常州大学 | Method of preparing 2,4-dichlorobenzaldehyde through continuous oxidation of 2,4-dichlorotoluene |
| CN106699525A (en) * | 2016-11-07 | 2017-05-24 | 常州大学 | Method for preparing 2,3-dichlorobenzaldehyde through continuous oxidization of 2,3-dichlorotoluene |
| CN106748685A (en) * | 2016-11-07 | 2017-05-31 | 常州大学 | A kind of method that parachlorotoluene continuous oxidation prepares 4-chloro-benzaldehyde |
| CN106748684A (en) * | 2016-11-07 | 2017-05-31 | 常州大学 | A kind of method of fluorobenzaldehyde between m-fluorotoluene continuous oxidation preparation |
| CN106854142A (en) * | 2016-11-07 | 2017-06-16 | 常州大学 | A kind of method that 2,5 dichlorotoleune continuous oxidation prepares 2,5 dichlorobenzaldehydes |
| CN108623453A (en) * | 2018-06-22 | 2018-10-09 | 杭州陶瑞生物科技有限公司 | A method of preparing aryl formate compound using microchannel continuous flow reactor |
| CN110938008A (en) * | 2019-12-09 | 2020-03-31 | 南京杰运医药科技有限公司 | Preparation method of o-aminoacetophenone |
| CN113979845A (en) * | 2021-11-18 | 2022-01-28 | 山东键兴新材料科技有限公司 | Production process method for preparing acetophenone by oxidizing ethylbenzene |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101293810A (en) * | 2007-04-28 | 2008-10-29 | 中国石油化工股份有限公司 | Liquid-phase oxidation method for cyclohexane |
| CN101426752A (en) * | 2006-03-23 | 2009-05-06 | 万罗赛斯公司 | Process for making styrene using microchannel process technology |
-
2011
- 2011-11-07 CN CN2011103467873A patent/CN102516052A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101426752A (en) * | 2006-03-23 | 2009-05-06 | 万罗赛斯公司 | Process for making styrene using microchannel process technology |
| CN101293810A (en) * | 2007-04-28 | 2008-10-29 | 中国石油化工股份有限公司 | Liquid-phase oxidation method for cyclohexane |
Non-Patent Citations (2)
| Title |
|---|
| 王园园: "乙苯液相催化氧化合成苯乙酮的研究", 《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》, no. 04, 30 April 2010 (2010-04-30), pages 014 - 105 * |
| 穆金霞 等: "微通道反应器在合成反应中的应用", 《化学进展》, vol. 20, no. 1, 31 January 2008 (2008-01-31), pages 60 - 75 * |
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| CN106631727A (en) * | 2016-11-07 | 2017-05-10 | 常州大学 | Method for preparing 2,5-difluorobenzaldehyde through continuous oxidation of 2,5-difluorotoluene |
| CN106631728A (en) * | 2016-11-07 | 2017-05-10 | 常州大学 | Method for preparing 3,5-difluorobenzaldehyde by 3,5-difluorotoluene continuous oxidation |
| CN106699526A (en) * | 2016-11-07 | 2017-05-24 | 常州大学 | Method of preparing 2,4-dichlorobenzaldehyde through continuous oxidation of 2,4-dichlorotoluene |
| CN106699525A (en) * | 2016-11-07 | 2017-05-24 | 常州大学 | Method for preparing 2,3-dichlorobenzaldehyde through continuous oxidization of 2,3-dichlorotoluene |
| CN106748685A (en) * | 2016-11-07 | 2017-05-31 | 常州大学 | A kind of method that parachlorotoluene continuous oxidation prepares 4-chloro-benzaldehyde |
| CN106748684A (en) * | 2016-11-07 | 2017-05-31 | 常州大学 | A kind of method of fluorobenzaldehyde between m-fluorotoluene continuous oxidation preparation |
| CN106854142A (en) * | 2016-11-07 | 2017-06-16 | 常州大学 | A kind of method that 2,5 dichlorotoleune continuous oxidation prepares 2,5 dichlorobenzaldehydes |
| CN108623453A (en) * | 2018-06-22 | 2018-10-09 | 杭州陶瑞生物科技有限公司 | A method of preparing aryl formate compound using microchannel continuous flow reactor |
| CN110938008A (en) * | 2019-12-09 | 2020-03-31 | 南京杰运医药科技有限公司 | Preparation method of o-aminoacetophenone |
| CN113979845A (en) * | 2021-11-18 | 2022-01-28 | 山东键兴新材料科技有限公司 | Production process method for preparing acetophenone by oxidizing ethylbenzene |
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Application publication date: 20120627 |