CN103058821B - Synthesis method of 2-phenyl-2-propanol and acetophenone through catalytic oxidation of cumene - Google Patents
Synthesis method of 2-phenyl-2-propanol and acetophenone through catalytic oxidation of cumene Download PDFInfo
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Abstract
The invention discloses a synthesis method of 2-phenyl-2-propanol and acetophenone through catalytic oxidation of cumene, the synthesis method includes that firstly, adding the cumene and a solid catalyst into a reactor, forming a suspension through ultrasonic processing, wherein the solid catalyst is nitrogen-doped carbon material, heating the obtained suspension to 40-100 DEG C, introducing oxygen for reaction at constant pressure; after the reaction is finished, separating the reaction mixture to obtain the solid catalyst and a liquid mixture which contains the 2-phenyl-2-propanol, the acetophenone and cumene hydrogen peroxide; and obtaining target products of the 2-phenyl-2-propanol and the acetophenone through separation and purification. The cumene is oxidized at the constant pressure to generate 2-phenyl-2-propanol and acetophenone, the nitrogen-doped carbon material is used as the heterogeneous reaction catalyst, the oxygen is used as oxidant, an operational process is simple, the nonmetal catalyst is free of corrosion, environment-friendly, low in price and capable of being used repeatedly, the conversion ratio of the cumene is relatively high, and the target products are good in selectivity.
Description
Technical field
The present invention relates to the synthetic method of 2-phenyl-2-propyl alcohol or methyl phenyl ketone, particularly relate to a kind of method that isopropyl benzene catalyzed oxidation synthesizes 2-phenyl-2-propyl alcohol and methyl phenyl ketone simultaneously, belong to organic synthesis applied technical field.
Background technology
2 ?benzene base ?2 ?propyl alcohol have rose fragrance, are the additives of spices and makeup, are also the important intermediate of industrial synthetic dicumyl peroxide.Its synthetic method, mainly taking isopropyl benzene hydroperoxide as raw material, comprises inorganic reducing agent reduction method and shortening method.At present, industrial synthetic 2 ?Ben Ji ?2 ?propyl alcohol adopt inorganic reducing agent reduction method, its building-up process is as follows: air is oxygenant, prepares isopropyl benzene hydroperoxide (CHP) taking alkaline solution as additive catalyzed oxidation isopropyl benzene; Then use Sodium Sulphide (NaS or Na
2sO
3) reduction CHP prepare 2 ?Ben Ji ?2 ?propyl alcohol.This method selectivity is higher, but can produce a large amount of alkalescence or the waste water of sulfur-bearing, and follow-up liquid waste disposal process is loaded down with trivial details, not only uneconomical but also not environmental protection; Taking isopropyl benzene as raw material in two steps synthetic 2 ?Ben Ji ?2 ?propyl alcohol, technique is more loaded down with trivial details.Therefore, find a kind of taking isopropyl benzene as raw material, the catalyzer of the not only efficient but also environmental protection of one-step synthesis 2 ?benzene base ?2 ?propyl alcohol, become the research direction of technique for this reason.
Transition metal can promote the decomposition of CHP generate 2 ?Ben Ji ?2 ?propyl alcohol, thereby accelerate cumene oxidation speed of reaction, be a kind of more feasible catalyzer.Publication number for CN101450324 ?the Chinese invention patent application of A provide a kind of with polymer-bound tripe amino-acid Schiff base metal copper complex catalysis cumene oxidation prepare 2 ?Ben Ji ?2 ?the method of propyl alcohol, selectivity is high, but temperature of reaction is high, low conversion rate; Catalyzer is prepared also more complicated simultaneously, and cost is high, is unfavorable for industrial application.Other taking isopropyl benzene as raw material, one-step synthesis 2 ?Ben Ji ?2 ?the report of propyl alcohol less.
Methyl phenyl ketone is a kind of important industrial chemicals, is also the important intermediate of synthetic other spices, and main application has: 1) have the features such as boiling point is high, stable, smell is happy, dissolving power is very strong, makes solvent; 2) make spices, be the blending raw material of the essence such as hawthorn Touch-me-notAction Plant and Syringa oblata Lindl. and be widely used in soap compound and tobacco flavour in; 3) for the synthesis of phenylglycollic acid, Phenylindole and ibuprofen etc.The method of current industrial employing air direct oxidation ethylbenzene methyl phenyl ketone processed, transformation efficiency and selectivity are all low.
In view of the deficiency that above-mentioned all kinds of catalyzer exist, developing a kind of catalytic activity green catalyst good and that be easy to realize industrial application is the emphasis of the existing technique of change.
In recent years, carbon material is carried out to nitrating processing and become a study hotspot of carbon material to change its mechanics, chemistry and chemical property.In liquid phase reaction, nitrating carbon material has better catalytic activity, and as in hexanaphthene liquid phase aerobic oxidation, the catalytic activity of nitrogen doped carbon nanotube is higher than common carbon nanotube, and catalyzer also can recycle simultaneously, thereby reduces costs.Up to the present, also do not see taking nitrating carbon material as heterogeneous catalyst, oxygen or air are oxygenant, catalyzed oxidation isopropyl benzene prepare 2 ?Ben Ji ?2 ?the open report of propyl alcohol and methyl phenyl ketone technique.
Summary of the invention
The object of the present invention is to provide that a kind of flow process is simple, operational safety, eco-friendly isopropyl benzene catalyzed oxidation simultaneously synthetic 2 ?Ben Ji ?2 ?the method of propyl alcohol and methyl phenyl ketone.
Object of the present invention is achieved through the following technical solutions:
Isopropyl benzene catalyzed oxidation synthetic 2 ?Ben Ji ?2 ?the method of propyl alcohol and methyl phenyl ketone, comprise the following steps:
(1) isopropyl benzene and solid catalyst are joined in reactor, supersound process forms suspension; Described solid catalyst is nitrating carbon material, and described nitrating carbon material is nitrogen doped carbon nanotube, nitrating Graphene or nitrating gac; By percentage to the quality, the itrogen content of getter with nitrogen doped of nitrating carbon material is 2～4.0%; Described nitrating carbon material solid catalyst and isopropyl benzene weight ratio are 0.006～0.012:1;
(2) suspension of gained is heated to 40～100 DEG C, passes into oxygen, under normal pressure, react 1～12h; Oxygenant passes in bubbling mode, and by every milliliter of isopropyl benzene, oxygen gas flow rate is 0.5～1.5mL/min;
(3) after the reaction of step (2) finishes, reaction mixture is separated, obtain solid catalyst and contain 2 ?Ben Ji ?2 ?the liquid mixture of propyl alcohol, methyl phenyl ketone and isopropyl benzene hydroperoxide;
(4) by the liquid mixture separating-purifying in step (3), obtain target product 2 ?Ben Ji ?2 ?propyl alcohol and methyl phenyl ketone.
For further realizing the object of the invention, the solid catalyst that step (3) obtains is for step (1), as solid catalyst raw material.
Described solid catalyst and isopropyl benzene weight ratio are preferably 0.008～0.01:1.
By percentage to the quality, the itrogen content of getter with nitrogen doped of nitrating carbon material is preferably 3.3～4.0.
Step (2) suspension is preferably heated to 60～80 DEG C.
Step (2) is preferably reacted 8～12h under normal pressure.
By every milliliter of isopropyl benzene, preferably oxygen gas flow rate is 0.8～1.0mL/min.
The present invention is taking oxygen as oxygenant, the active ingredient using nitrating carbon material as heterogeneous catalyst, catalysis cumene oxidation reaction preparation 2 ?Ben Ji ?2 ?propyl alcohol and methyl phenyl ketone.
Compared with prior art, tool has the following advantages in the present invention:
1) the present invention taking isopropyl benzene as raw material one-step synthesis 2 ?Ben Ji ?2 ?propyl alcohol, technique is simple, cost-saving.
2) the present invention is using nonmetal-nitrating carbon material as catalyzer, and catalyzer can direct filtration separate with product; Simultaneously carbon material has wide material sources, low price, and environmental friendliness, the advantage such as can be recycled.
3) the present invention's nitrating carbon material used is higher to cumene oxidation catalytic reaction activity, and selectivity is better.
Brief description of the drawings
Fig. 1～5 be respectively acetonitrile, toluene, isopropyl benzene, methyl phenyl ketone and 2 ?Ben Ji ?2 ?the gas chromatogram of propyl alcohol standard specimen;
Fig. 6 is the gas chromatogram of embodiment 2.
Embodiment
Below in conjunction with embodiment and accompanying drawing, the present invention will be further described, but the scope of protection of present invention is not limited to the scope of embodiment statement.
In embodiment about isopropyl benzene transformation efficiency (%) and 2 ?Ben Ji ?2 ?the measurement and calculation method (normalization method) of propyl alcohol, methyl phenyl ketone and CHP selectivity (%) as follows:
(1) separate rear gained liquid mixture, take two parts (each 0.8g).The content of iodometric determination CHP for a copy of it: add m in iodine flask
1g(0.8g) reaction gained liquid mixture, adds 20mL glacial acetic acid solution, then adds 2gNaHCO
3pressed powder, gently shake make pressed powder and liquid mixing even; Then add the saturated KI solution of 10mL, immerse in 60 DEG C of oil baths and react while extremely substantially no longer producing bubble, taking-up water cooling, adds 100mL distilled water; With concentration be c
1the standard Na of mol/L (0.15mol/L)
2s
2o
3standardization of solution to solution is light yellow, adds 2mL Starch Indicator (massfraction is 5%), continues to be titrated to solution and becomes oyster white from blueness, is titration end point, writes down the standard Na of consumption
2s
2o
3liquor capacity is V mL.
Claim in addition a liquid mixture, quality is m
2g(0.8g), add m
3g(0.4g) toluene is marked in doing, after shaking up, add slightly excessive triphenylphosphine reduction, add again 2mL dilution in acetonitrile, then use chromatography of gases (150 DEG C of column temperatures, sampler and detector temperature are 280 DEG C) measure isopropyl benzene in every gram of liquid mixture, 2 ?Ben Ji ?2 ?the amount of substance of propyl alcohol and methyl phenyl ketone be respectively n
1, n
2and n
3(mol).
In every gram of liquid mixture of iodometric determination, the amount of substance of CHP is:
n
CHP（mol）=c
1×V×0.5/(m
1×1000)
Transformation efficiency (%)=100 × (n of isopropyl benzene
2+ n
3)/(n
1+n
2+ n
3)
Selectivity (%)=100 × n of CHP
cHP/ (n
2+ n
3)
Selectivity (%)=100 × n of methyl phenyl ketone
3/ (n
2+ n
3)
2 ?Ben Ji ?2 ?selectivity (%)=100 × (n of propyl alcohol
2?n
cHP)/(n
2+ n
3).
By the nitrogen doped carbon nanotube of 10.00mL isopropyl benzene (density is 0.84g/mL) and 100mg different nitrogen contents, (catalyzer and isopropyl benzene weight ratio are 0.012:1, nitrogen content is in table 1, nitrogen content in table is mass content) join in there-necked flask, ultrasonic 2min(frequency 40kHz, 30 DEG C), form mixing suspension.Then under magnetic agitation, this mixed solution is placed in to oil bath and is heated to 80 DEG C, then pass into oxygen with 10mL/min speed, under normal pressure, react 8h.After reaction finishes, gained mixed solution can obtain after filtration solid catalyst and contain 2 ?Ben Ji ?2 ?the liquid mixture of propyl alcohol, methyl phenyl ketone and CHP.Fig. 6 is the gas chromatogram of embodiment 2, the gas chromatogram of acetonitrile, toluene, isopropyl benzene, methyl phenyl ketone and 2-phenyl-2-propyl alcohol standard specimen of comparison diagram 1～5, known, the product after triphenylphosphine reduction be 2 ?Ben Ji ?2 ?propyl alcohol and methyl phenyl ketone, the amount of CHP is recorded by iodometry.
Liquid mixture is analyzed, measured the transformation efficiency of isopropyl benzene and the selectivity of product the results are shown in Table 1.In analytical table 1, data are known, and when nitrogen content is lower, along with nitrogen content is higher, the catalytic activity of nitrogen doped carbon nanotube is better, simultaneously target product methyl phenyl ketone and 2 ?Ben Ji ?2 ?the selectivity of propyl alcohol higher; Nitrogen content is 2.1%～4.0% time.Target product overall selectivity has reached more than 70%, when nitrogen content is 3.3%～4.0%, increases nitrogen content little to activity influence.
The impact of the nitrogen doped carbon nanotube of table 1 different nitrogen contents on isopropyl benzene catalytic oxidation activity
| |
1 | 2 | 3 | 4 |
| Nitrogen content (%, quality) | 0 | 2.1 | 3.3 | 4.0 |
| Isopropyl benzene transformation efficiency (%) | 16.1 | 40.8 | 73.9 | 72.1 |
| Methyl phenyl ketone selectivity (%) | 1.6 | 19.1 | 39.7 | 40.5 |
| 2 ?Ben Ji ?2 ?propyl alcohol selectivity (%) | 8.4 | 54.4 | 57 | 56.2 |
| CHP selectivity (%) | 90.0 | 26.5 | 3.3 | 3.3 |
| Target product overall selectivity (%) | 10.0 | 73.5 | 96.7 | 96.7 |
By 10.00mL isopropyl benzene (density is 0.84g/mL) and 100mg solid nitrating carbon material, (catalyzer and isopropyl benzene weight ratio are 0.012:1, solid nitrating carbon material kind is in table 2), join in there-necked flask ultrasonic 2min(frequency 40kHz, 30 DEG C), form mixing suspension.Then under magnetic agitation, this mixed solution is placed in to oil bath and is heated to 80 DEG C, then pass into oxygen with 10mL/min speed, under normal pressure, react 8h.After reaction finishes, gained mixed solution can obtain solid catalyst and liquid mixture after filtration.Liquid mixture is analyzed, measured the selectivity of transformation efficiency and the product of isopropyl benzene, the results are shown in Table 2.In analytical table 1,2, data are known, and in isopropyl benzene liquid-phase catalytic oxidation, nitrogen doped carbon nanotube has better catalytic activity and target product selectivity.With nitrating carbon compositing catalyst, although target product overall selectivity only has 23.0%, target product overall selectivity has also exceeded 20%, and isopropyl benzene transformation efficiency reaches 25.7%, CHP selectivity and reach 77.0%, can be used for synthetic CHP.
The activity of the different nitrating carbon materials of table 2 in cumene oxidation reaction
| |
5 | 6 |
| Catalyzer | Nitrating gac | Nitrating Graphene |
| Isopropyl benzene transformation efficiency (%) | 25.7 | 27.4 |
| Methyl phenyl ketone selectivity (%) | 17.8 | 12.3 |
| 2 ?Ben Ji ?2 ?propyl alcohol selectivity (%) | 5.2 | 51.2 |
| CHP selectivity (%) | 77.0 | 36.5 |
| Target product overall selectivity (%) | 23.0 | 63.5 |
By 10.00mL isopropyl benzene (density is 0.84g/mL) and 100mg nitrogen doped carbon nanotube, (nitrogen content is identical with embodiment 3, catalyzer and isopropyl benzene weight ratio are 0.012:1) join in there-necked flask, ultrasonic 2min(frequency 40kHz, 30 DEG C, also can ultrasonic 5min), form mixing suspension.Then under magnetic agitation, this mixing suspension is placed in to oil bath and is heated to, after predetermined temperature of reaction (as table 3), under normal pressure, pass into oxygen with 10mL/min speed, reaction 8h.After reaction finishes, gained mixed solution can obtain solid catalyst and liquid mixture after filtration.Liquid mixture is analyzed, measure the transformation efficiency of isopropyl benzene and methyl phenyl ketone, 2 ?Ben Ji ?2 ?the selectivity of propyl alcohol the results are shown in Table 3.Comparing embodiment 7,8,3 and 9, can find out, temperature raises and is conducive to the oxidation of isopropyl benzene, also make target product methyl phenyl ketone and 2 ?Ben Ji ?2 ?the overall selectivity of propyl alcohol increase.In addition, along with the rising of temperature of reaction, also there is change in the mol ratio of alcohol, ketone, can regulate and control by changing temperature the mol ratio of alcohol, ketone.
The impact of table 3 temperature of reaction on isopropyl benzene peroxidation
| |
7 | 8 | 9 |
| Temperature of reaction (DEG C) | 40 | 60 | 100 |
| Isopropyl benzene transformation efficiency (%) | 30.1 | 61.1 | 76.5 |
| Methyl phenyl ketone selectivity (%) | 13.2 | 28.4 | 48.9 |
| 2 ?Ben Ji ?2 ?propyl alcohol selectivity (%) | 72.6 | 67.3 | 49.9 |
| Target product overall selectivity (%) | 85.8 | 95.7 | 98.8 |
| Alcohol, ketone mol ratio | 5.5 | 2.4 | 1.0 |
Embodiment 10～13
By 10.0mL isopropyl benzene (density is 0.84g/mL) and 100mg nitrogen doped carbon nanotube, (nitrogen content is identical with embodiment 3; Catalyzer and isopropyl benzene weight ratio are 0.012:1) join in there-necked flask, under magnetic agitation, this mixed solution is placed in to oil bath and is heated to 80 DEG C of temperature of reaction, then pass into oxygen with 10mL/min speed, under normal pressure, react certain hour (in table 4).After reaction finishes, gained mixed solution can obtain solid catalyst and liquid mixture after filtration.Liquid mixture is analyzed, measure the transformation efficiency of isopropyl benzene and methyl phenyl ketone, 2 ?Ben Ji ?2 ?the selectivity of propyl alcohol, the results are shown in Table 4.In analytical table, data are known, and along with the increase in reaction times, the transformation efficiency of isopropyl benzene constantly increases, target product methyl phenyl ketone and 2 ?Ben Ji ?2 ?the overall selectivity of propyl alcohol more than 85%.
The impact of table 4 reaction times on cumene oxidation reaction
| Embodiment | 10 | 11 | 12 | 13 |
| Reaction times (h) | 1 | 2 | 4 | 12 |
| Isopropyl benzene transformation efficiency (%) | 21.0 | 31.5 | 55.9 | 79.8 |
| Methyl phenyl ketone selectivity (%) | 30.7 | 25.6 | 38.6 | 41.2 |
| 2 ?Ben Ji ?2 ?propyl alcohol selectivity (%) | 68.3 | 59.5 | 57.6 | 56.6 |
| Target product overall selectivity (%) | 99.0 | 85.1 | 96.2 | 97.8 |
Embodiment 14～15
By 10.00mL isopropyl benzene (density is 0.84g/mL) and the nitrogen doped carbon nanotube of certain mass, (nitrogen content is identical with embodiment 3; Catalyst levels is in table 5) join in there-necked flask ultrasonic 2min(frequency 40kHz, 30 DEG C), form mixing suspension.Then under magnetic agitation, this mixed solution is placed in to oil bath and is heated to 80 DEG C of temperature of reaction, then pass into oxygen with 10mL/min speed, under normal pressure, react 8h.After reaction finishes, gained mixed solution can obtain solid catalyst and liquid mixture after filtration.Liquid mixture is analyzed, measure the transformation efficiency of isopropyl benzene and methyl phenyl ketone, 2 ?Ben Ji ?2 ?the selectivity of propyl alcohol, the results are shown in Table 5.Comparing embodiment 14,15,3, can find out that reaction has good catalytic activity to nitrogen doped carbon nanotube to cumene oxidation, and catalyzer and isopropyl benzene weight ratio are in the time of 0.006～0.012:1, little on transformation efficiency impact.
The impact of table 5 catalyst levels on cumene oxidation reaction
| Embodiment | 14 | 15 |
| Catalyzer and isopropyl benzene weight ratio | 0 | 0.006 |
| Isopropyl benzene transformation efficiency (%) | 2.7 | 68.9 |
| Methyl phenyl ketone selectivity (%) | 0 | 35.5 |
| 2 ?Ben Ji ?2 ?propyl alcohol selectivity (%) | 0 | 56.8 |
| Target product overall selectivity (%) | 0 | 94.3 |
Embodiment 16～17
10.00mL isopropyl benzene (density is 0.84g/mL) and 100mg nitrogen doped carbon nanotube (nitrogen content is identical with embodiment 3) are joined in there-necked flask to ultrasonic 2min(frequency 40kHz, 30 DEG C), form mixing suspension.Then under magnetic agitation, this mixed solution is placed in to oil bath and is heated to 80 DEG C of temperature of reaction, then pass into oxygen with certain flow rate (in table 6), under normal pressure, react 8h.After reaction finishes, gained mixed solution can obtain solid catalyst and liquid mixture after filtration.Liquid mixture is analyzed, measure the transformation efficiency of isopropyl benzene and methyl phenyl ketone, 2 ?Ben Ji ?2 ?the selectivity of propyl alcohol, the results are shown in Table 6.Comparing embodiment 16,3,17, in the scope of research, oxygen flow is little on the catalytic activity impact of cumene oxidation reaction.
The impact of table 6 oxygen gas flow rate on cumene oxidation reaction
| Embodiment | 16 | 17 |
| Oxygen gas flow rate (mL/min) | 5 | 15 |
| Isopropyl benzene transformation efficiency (%) | 68.5 | 72.4 |
| Methyl phenyl ketone selectivity (%) | 36.0 | 38.5 |
| 2 ?Ben Ji ?2 ?propyl alcohol selectivity (%) | 55.0 | 58.3 |
| Target product overall selectivity (%) | 91.0 | 96.8 |
Embodiment 18
(1) by 10.00mL isopropyl benzene (density is 0.84g/mL) and 100mg nitrogen doped carbon nanotube, (nitrogen content is identical with embodiment 3; Catalyzer and isopropyl benzene weight ratio are 0.012:1) join in there-necked flask ultrasonic 2min(frequency 40kHz, 30 DEG C), form mixing suspension.Then under magnetic agitation, this mixed solution is placed in to oil bath and is heated to 80 DEG C of temperature of reaction, then pass into oxygen with 10mL/min speed, under normal pressure, react 8h.After reaction finishes, gained mixed solution can obtain solid catalyst and liquid mixture after filtration.Liquid mixture is analyzed, measure the transformation efficiency of isopropyl benzene and methyl phenyl ketone, 2 ?Ben Ji ?2 ?the selectivity of propyl alcohol; Gained solid catalyst is dry 12h at 110 DEG C.
(2) using the dried carbon nanotube of step (1) as catalyzer, under the condition identical with step (1), react, by identical method mensuration transformation efficiency and selectivity.So this catalyst recirculation is used four times, measuredly the results are shown in Table 7.Reuse four times, transformation efficiency and selectivity change little, illustrate that nitrogen doped carbon nanotube is reused, thereby reduce catalyzer cost.
Table 7 catalyst stability experimental result
| |
1 | 2 | 3 | 4 |
| Isopropyl benzene transformation efficiency (%) | 64.3 | 72.1 | 63.6 | 63.8 |
| Methyl phenyl ketone selectivity (%) | 34.6 | 36.1 | 27.5 | 24.7 |
| 2 ?Ben Ji ?2 ?propyl alcohol selectivity (%) | 61.6 | 57.2 | 60.9 | 63.6 |
| Target product selectivity (%) | 96.2 | 93.3 | 88.4 | 88.3 |
Claims (6)
1. a method for the synthetic 2-phenyl-2-propyl alcohol of isopropyl benzene catalyzed oxidation and methyl phenyl ketone, is characterized in that comprising the following steps:
(1) isopropyl benzene and solid catalyst are joined in reactor, supersound process forms suspension; Described solid catalyst is nitrating carbon material, and described nitrating carbon material is nitrogen doped carbon nanotube, nitrating Graphene or nitrating gac; By percentage to the quality, the itrogen content of getter with nitrogen doped of nitrating carbon material is 2～4.0%; Described nitrating carbon material solid catalyst and isopropyl benzene weight ratio are 0.006～0.012: 1;
(2) suspension of gained is heated to 40～100 DEG C, passes into oxygen, under normal pressure, react 1～12h; Oxygenant passes in bubbling mode, and by every milliliter of isopropyl benzene, oxygen gas flow rate is 0.5～1.5m L/min;
(3) after the reaction of step (2) finishes, reaction mixture is separated, obtain solid catalyst and contain the liquid mixture of 2-phenyl-2-propyl alcohol, methyl phenyl ketone and isopropyl benzene hydroperoxide;
(4), by the liquid mixture separating-purifying in step (3), obtain target product 2-phenyl-2-propyl alcohol and methyl phenyl ketone.
2. the method that isopropyl benzene catalyzed oxidation synthesizes 2-phenyl-2-propyl alcohol and methyl phenyl ketone according to claim 1, is characterized in that: the solid catalyst that step (3) obtains is for step (1), as solid catalyst raw material.
3. the method that isopropyl benzene catalyzed oxidation synthesizes 2-phenyl-2-propyl alcohol and methyl phenyl ketone according to claim 1, is characterized in that: described solid catalyst and isopropyl benzene weight ratio are 0.008～0.01: 1.
4. the method that isopropyl benzene catalyzed oxidation synthesizes 2-phenyl-2-propyl alcohol and methyl phenyl ketone according to claim 1, is characterized in that: most 60～80 DEG C of step (2) suspension heating.
5. the method that isopropyl benzene catalyzed oxidation synthesizes 2-phenyl-2-propyl alcohol and methyl phenyl ketone according to claim 1, is characterized in that: under step (2) normal pressure, react 8～12h.
6. the method that isopropyl benzene catalyzed oxidation synthesizes 2-phenyl-2-propyl alcohol and methyl phenyl ketone according to claim 1, is characterized in that: by every milliliter of isopropyl benzene, oxygen gas flow rate is 0.8～1.0mL/min.
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| CN104402789B (en) * | 2014-11-21 | 2017-01-04 | 华南理工大学 | The method of a kind of structuring carbon nano-tube catalyst catalysis cumene oxidation and reactor |
| CN105116089B (en) * | 2015-08-24 | 2017-08-01 | 山东出入境检验检疫局检验检疫技术中心 | The assay method of the propyl alcohol total amount of 2 phenyl 2 in plastics and plastic products |
| CN109503328B (en) * | 2018-12-21 | 2020-09-29 | 大连理工大学 | Method for preparing 2-phenyl-2-propanol at normal temperature |
| CN110423185B (en) * | 2019-08-28 | 2022-03-18 | 浙江工业大学 | Method for selectively oxidizing cumene compound |
| CN110759818B (en) * | 2019-10-30 | 2021-12-21 | 华南理工大学 | Method for preparing acetophenone by catalytic oxidation of ethylbenzene by nitrogen-doped carbon nano tube |
| CN111269087B (en) * | 2020-02-29 | 2021-11-23 | 华南理工大学 | Method for catalyzing cumene oxidation by trace copper-promoted carbon nano tube |
| CN111675599A (en) * | 2020-04-27 | 2020-09-18 | 浙江工业大学 | Method for catalyzing and oxidizing aromatic benzyl tertiary C-H bond into tertiary alcohol by metalloporphyrin |
| CN114073983B (en) * | 2020-08-17 | 2023-05-30 | 万华化学集团股份有限公司 | Diisopropylbenzene oxidation catalyst and preparation method thereof, and method for preparing diisopropylbenzene dibenzyl alcohol by using diisopropylbenzene oxidation catalyst |
| CN113735699B (en) * | 2021-09-17 | 2024-01-23 | 黑龙江立科新材料有限公司 | Preparation method of acetophenone |
| CN114685243B (en) * | 2022-04-01 | 2023-02-07 | 大连理工大学 | Green and efficient preparation method of 2-phenyl-2-propanol series compounds |
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