CN109503328A - The method of 2- phenyl -2- propyl alcohol is prepared at normal temperature - Google Patents
The method of 2- phenyl -2- propyl alcohol is prepared at normal temperature Download PDFInfo
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- CN109503328A CN109503328A CN201811573919.4A CN201811573919A CN109503328A CN 109503328 A CN109503328 A CN 109503328A CN 201811573919 A CN201811573919 A CN 201811573919A CN 109503328 A CN109503328 A CN 109503328A
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
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Abstract
The present invention discloses one kind at normal temperature using isopropylbenzene as raw material, and oxygen is oxidant, and under the irradiation of xenon light, new process of the dibenzothiophenes as the 2- phenyl -2- propyl alcohol synthesis for circulating reduction agent is added.The irradiation of xenon light, which is added, reduces reaction temperature, and improves the selectivity of the reaction, so that the yield of 2- phenyl -2- propyl alcohol improves between 13~23% relative to no xenon light without reducing agent at room temperature；Catalytic life and catalytic activity that dibenzothiophenes is conducive to raising metalloporphyrin as reducing agent is added, and oxidation product Dibenzothiophene sulfoxide deoxidation can generate dibenzothiophenes automatically under photocatalysis, it is recycled, isopropylbenzene conversion ratio is effectively improved, is improved between 4~11% relative to reducing agent is added without.
Description
Technical field
The invention belongs to Minute Organic Synthesis field, a kind of be related to preparing 2- phenyl -2- propyl alcohol under room temperature method.
Background technique
2- phenyl -2- propyl alcohol is a kind of important organic chemical industry's intermediate and fine chemical material, because there is rose fragrance,
Can be used as fragrance, modulation bouquet type composition with cosmetics and other spice materials, mainly for the production of cumyl peroxide.
Cumyl peroxide is a kind of excellent organic peroxide, and the crosslinking agent and high molecular material as rubber and plastics draw
Agent is sent out, rubber, polyolefin, foamed plastics, wire and cable, shoemaking and enamel insulated wire are widely used in.Since peroxidating two is different
The importance of propyl benzene, the preparation of 2- phenyl -2- propyl alcohol also seem more important.
The preparation of 2- phenyl -2- propyl alcohol is mainly using cumyl hydroperoxide as raw material, by inorganic reducing agent reduction, by force
The synthesis of the methods of alkali or heavy metal catalyst degradation, electroreduction and catalytic hydrogenation.It was at present restored by sulfide
The method production of hydrogen oxide isopropylbenzene, due to needing the inorganic salts and peroxide reactions of equivalent, reaction can be generated
A large amount of waste water and cheap inorganic acid salt, cause environmental pollution.Highly basic or heavy metal catalyst degradation technique are to equipment corrosion and ring
Border is seriously polluted, and electrolytic reduction reaction speed is slow, cannot achieve industrialization；And catalytic hydrogenating reduction is a kind of strongly exothermic anti-
It answers, there is very high risk in large-scale production, and atom utilization is low.
2- phenyl -2- propyl alcohol is prepared using polymer-bound tripe amino-acid Schiff base metal complexes catalysis isopropylbenzene
Method, selectivity is high, but reaction temperature is high, and conversion ratio is low；Catalyst preparation is also more complicated simultaneously, at high cost
(CN101450324A).Using nitrating solid carbonaceous material as heterogeneous reaction catalyst, selectively it is up at 40 DEG C
72.6% (CN103058821A).
Metalloporphyrin class catalyst is using a variety of oxidants such as peroxide, air and oxygen etc. as oxygen source, catalytic machine
It manages similar to enzyme system catalysis and is used as bionic catalyst, with catalytic activity is high, regioselectivity is good, itself can voluntarily be dropped
The advantages that solution, while catalyst amount is few, reduces certain production cost and energy consumption because catalyst is without separation, thus quilt
Extensive concern.But when being reacted with catalysis of metalloporphyrin isopropylbenzene, since 2- phenyl -2- propyl alcohol is to cumyl hydroperoxide
Decomposition has a strong inhibiting effect, and the cumyl hydroperoxide of high concentration and and its alkoxy free group that generates to metal porphin
Quinoline is damaged to a certain extent effect.When therefore, with catalysis of metalloporphyrin cumin synthesis 2- phenyl -2- propyl alcohol, due to metal porphin
The service life of quinoline and the inhibiting effect of 2- phenyl -2- propyl alcohol, so that when using metalloporphyrin as catalyst, the conversion ratio of reaction
It is not high, so that the degree that the oxidation reaction of isopropylbenzene carries out is relatively low.
Summary of the invention
In view of the above-mentioned prior art the problem of synthesizing 2- phenyl -2- propyl alcohol, it is an object of the present invention to mention
For a kind of guard catalyst service life, the 2- benzene for increasing reaction conversion ratio and occurring that the reaction at room temperature
The preparation method of base -2- propyl alcohol.
Above-mentioned purpose of the invention adopts the following technical scheme that realize.
A kind of preparation method of 2- phenyl -2- propyl alcohol, which is characterized in that isopropylbenzene and oxygen are in the presence of a catalyst through urging
2- phenyl -2- propyl alcohol is made in oxidation, wherein the catalyst is porphyrin catalyst, in the catalytic oxidation
Dibenzothiophenes is added to be used as recycled material.
In the above-mentioned technical solutions, the reaction temperature of the catalytic oxidation be 20-120 DEG C, preferably 70~100
DEG C, more preferably 80~90 DEG C, the reaction time is 5~17h, preferably 5~10h.
In the above-mentioned technical solutions, 2- is made through catalytic oxidation in the presence of illumination, catalyst in isopropylbenzene and oxygen
Phenyl -2- propyl alcohol, wherein the illumination is xenon light, and the catalyst is porphyrin catalyst, is added in the catalytic oxidation
Enter dibenzothiophenes to be used as recycled material.Wherein, the reaction temperature of the catalytic oxidation is 20~80 DEG C, preferably
20~35 DEG C of reaction time are 5~17h.
In the above-mentioned technical solutions, the porphyrin catalyst and isopropylbenzene mass ratio are 0.2~0.5mg:1g.
In the above-mentioned technical solutions, the dibenzothiophenes and isopropylbenzene mass ratio are 3~20mg:1g.
In the above-mentioned technical solutions, it is 2~20mL/min, preferably 10~15mL/min that rate, which is added, in the oxygen.
The oxygen supply device of this field routine, such as oxygen tank, oxygen cylinder etc. can be used in oxygen supply.Easy device can also be used,
If oxygen balloon, oxygen bag are as oxygen supply device.
In the above-mentioned technical solutions, the intensity of the xenon light is 200~500W, preferably 300W.The irradiation of xenon light can adopt
It is realized with the device of transmitting xenon light, xenon lamp such as can be used.
In the above-mentioned technical solutions, the porphyrin catalyst is metalloporphyrin.The metal of this field routine can be used
Porphyrin, such as PORPHYRIN IRON, Manganese Porphyrin, to chlorine PORPHYRIN IRON.
In preparation method of the invention, round-bottomed flask is can be used in the catalytic oxidation or three neck round bottom flask carries out,
Oxygen is supplied by oxygen tank, and agitating mode is magneton stirring, since reaction is that gas-liquid two-phase reacts, using liquid phase agitating paddle
Mixing effect more preferably.
In the present invention, the catalyst that catalytic oxidation uses is metalloporphyrin class catalyst, since metalloporphyrin is being urged
During change, high valence transition state will form, there is strong oxidizing property, it may occur that the oxidation of itself, and dibenzo thiophene is added in the present invention
Pheno carrys out the guard catalyst service life as reducing agent, enhances the function and effect of catalyst.On the other hand, in catalysis oxidation of the present invention
Dibenzothiophenes is oxidized into Dibenzothiophene sulfoxide in reaction.At room temperature, isopropylbenzene and oxygen urging in metalloporphyrin
It is very low to change lower reaction yield, is irradiated using xenon light, so that 2- phenyl -2- propyl alcohol yield greatly improves at room temperature for reaction, also,
Under the irradiation of xenon light, the Dibenzothiophene sulfoxide generated in reaction can be using deoxidation and reduction as dibenzothiophenes, so that dibenzo thiophene
Pheno can be recycled, and the elemental oxygen that Dibenzothiophene sulfoxide deoxidation is formed can also further aoxidize isopropylbenzene, favorably
In the conversion ratio for improving isopropylbenzene.
Beneficial effects of the present invention:
The present invention provides one kind using isopropylbenzene as raw material, and oxygen is oxidant, and under the irradiation of xenon light, dibenzothiophenes is added
New process as the 2- phenyl -2- propyl alcohol synthesis for circulating reduction agent.Reaction temperature is reduced using the irradiation of xenon light, and is mentioned
The selectivity of the high reaction is added dibenzothiophenes as reducing agent and is conducive to protect the catalytic life of metalloporphyrin and is catalyzed live
Property, and oxidation product Dibenzothiophene sulfoxide deoxidation can generate dibenzothiophenes automatically under photocatalysis, be recycled, and improve
The conversion ratio of isopropylbenzene.The results show that cumene oxidation reaction carries out under the irradiation of xenon light, so that at room temperature (20~35
DEG C) yield of 2- phenyl -2- propyl alcohol improves between 13~23% relative to no xenon light without reducing agent.Dibenzothiophenes conduct is added
Reducing agent and recycled material effectively improve isopropylbenzene conversion ratio, improve between 4~11% relative to reducing agent is added without.
The preparation of 2- phenyl -2- propyl alcohol is mainly using cumyl hydroperoxide as raw material, and cumyl hydroperoxide is at present
It is reacted and is obtained by cumene oxidation, since the reaction is radical reaction, reaction selectivity is poor, and peroxide easily decomposes,
Condition of storage is harsh.The present invention is selected using isopropylbenzene as raw material, generates 2- phenyl -2- propyl alcohol by dioxygen oxidation single step reaction,
The synthesis of intermediate product cumyl hydroperoxide is omitted, the simple process, it is convenient, safe and have certain economy.
Detailed description of the invention
Fig. 1 is the schematic device for preparing 2- phenyl -2- propyl alcohol that present invention implementation uses.
Symbol mark: 1, liquid inlet opening, 2, oxygen supply device, 3, liquid outlet opening, 4, three mouthfuls of light reaction round bottoms are burnt
Bottle, 5, heating water bath pot, 6, xenon lamp.
Specific embodiment
Following non-limiting embodiments can make those skilled in the art that the present invention be more completely understood, but not with
Any mode limits the present invention.In following embodiments, unless otherwise specified, used experimental method is conventional method, institute
It can be bought from biological or chemical company with material, reagent etc..
The new process of 2- phenyl -2- propyl alcohol is prepared under a kind of room temperature, isopropylbenzene and oxygen are urged in the presence of illumination, catalyst
Change to aoxidize and 2- phenyl -2- propyl alcohol is made, wherein the light source is xenon light, and the catalyst is metalloporphyrin class catalyst, described
Catalytic oxidation is added dibenzothiophenes reducing agent and is used as recycled material, and oxidation product Dibenzothiophene sulfoxide is urged in light
Automatic deoxidation and reduction is dibenzothiophenes under change, achievees the purpose that circulation technology.
Following embodiments provide the specific implementation that a kind of isopropylbenzene provided by the invention prepares the technique of 2- phenyl -2- propyl alcohol
Mode.Cumene oxidation reaction carries out in three mouthfuls of round-bottomed bottles.As shown in Figure 1, three neck round bottom flask is placed in heating water bath pot
In, heating water bath and temperature control are put into magneton in flask for magnetic agitation, and the isopropylbenzene dissolved with catalysis of metalloporphyrin agent is molten
Liquid is added to three neck round bottom flask, and dibenzothiophenes is added, and is passed through oxygen with the rate of 10mL/min, opens stirring, water-bath into
Row heating, opens xenon radiant, and reaction starts, and the catalytic oxidation of isopropylbenzene is carried out in the case where setting reaction temperature.
After a certain period of time, sampling is dissolved in hplc grade methanol for reaction, tests content using liquid chromatogram after filtering, monitoring is anti-
Answer process.The hypo solution titration that sample is demarcated after separately taking a part to react, detects by-product hydrogen peroxide isopropyl
The mass content of benzene.
After oxidation reaction, collect liquid phase substance, with liquid chromatogram by acetophenone in internal mark method determination reaction solution,
Isopropylbenzene, 2- phenyl -2- propyl alcohol substance amount, contained with the quality of cumyl hydroperoxide after indirect iodometric processes drop reaction
It measures, and the isopropylbenzene conversion ratio of oxidation reaction, 2- phenyl -2- propyl alcohol yield and 2- benzene is calculated according to obtained data
Base -2- propyl alcohol selectivity.
Following embodiments are all made of reaction unit progress catalytic oxidation as shown in Figure 1 and 2- phenyl -2- are prepared
Propyl alcohol, only provide in embodiment corresponding material additional amount and each technological parameter, repeat no more above-mentioned concrete operation step.
The xenon lamp that following embodiments use is voltage rating 220V, rated power 300W, a length of 190mm of real arcs, work
Make voltage 100V, the U-shaped xenon long-arc lamp of operating current 3A.
Embodiment 1
(1) by 30mL isopropylbenzene, 12mg is added in three neck round bottom flask chlorine PORPHYRIN IRON, 500mg dibenzothiophenes, with
The rate of 10mL/min is passed through oxygen, opens xenon source irradiation, sets reaction temperature as 35 DEG C, reaction time 10h.
(2) with the content of each substance after indirect iodometric processes and liquid chromatogram measuring reaction.
The reaction, isopropylbenzene conversion ratio are that the selectivity of 31.97%, 2- phenyl -2- propyl alcohol is 87.01%, and yield is
27.82%.
Embodiment 2
(1) by 30mL isopropylbenzene, 12mg is added in three neck round bottom flask chlorine PORPHYRIN IRON, logical with the rate of 10mL/min
Enter oxygen, sets reaction temperature as 35 DEG C, reaction time 10h.
(2) with the content of each substance after indirect iodometric processes and liquid chromatogram measuring reaction.
The reaction, isopropylbenzene conversion ratio are that the selectivity of 8.75%, 2- phenyl -2- propyl alcohol is 57.25%, and yield is
5.01%.
Embodiment 3
(1) by 30mL isopropylbenzene, 12mg is added in three neck round bottom flask chlorine PORPHYRIN IRON, logical with the rate of 10mL/min
Enter oxygen, open xenon source irradiation, sets reaction temperature as 35 DEG C, reaction time 10h.
(2) with the content of each substance after indirect iodometric processes and liquid chromatogram measuring reaction.
The reaction, isopropylbenzene conversion ratio are that the selectivity of 27.91%, 2- phenyl -2- propyl alcohol is 86.20%, and yield is
24.06%.
Embodiment 4
(1) by 30mL isopropylbenzene, 12mg is added in three neck round bottom flask chlorine PORPHYRIN IRON, 500mg dibenzothiophenes, with
The rate of 10mL/min is passed through oxygen, opens xenon source irradiation, sets reaction temperature as 80 DEG C, reaction time 10h.
(2) with the content of each substance after indirect iodometric processes and liquid chromatogram measuring reaction.
The reaction, isopropylbenzene conversion ratio are that the selectivity of 34.15%, 2- phenyl -2- propyl alcohol is 40.27%, and yield is
13.75%.
Embodiment 5
(1) by 30mL isopropylbenzene, 12mg PORPHYRIN IRON, 100mg dibenzothiophenes is added in three neck round bottom flask, with
The rate of 10mL/min is passed through oxygen, opens xenon source irradiation, sets reaction temperature as 20 DEG C, reaction time 6h.
(2) with the content of each substance after indirect iodometric processes and liquid chromatogram measuring reaction.
The reaction, isopropylbenzene conversion ratio are that the selectivity of 23.80%, 2- phenyl -2- propyl alcohol is 90.96%, and yield is
21.65%.
Embodiment 6
(1) by 30mL isopropylbenzene, 12mg PORPHYRIN IRON is added in three neck round bottom flask, is passed through oxygen with the rate of 10mL/min
Gas, sets reaction temperature as 20 DEG C, reaction time 6h.
(2) with the content of each substance after indirect iodometric processes and liquid chromatogram measuring reaction.
The reaction, isopropylbenzene conversion ratio are that the selectivity of 10.24%, 2- phenyl -2- propyl alcohol is 89.23%, and yield is
9.13%.
Embodiment 7
(1) by 30mL isopropylbenzene, 12mg PORPHYRIN IRON, 100mg dibenzothiophenes is added in three neck round bottom flask, with
The rate of 10mL/min is passed through oxygen, opens xenon source irradiation, sets reaction temperature as 20 DEG C, reaction time 10h.
(2) with the content of each substance after indirect iodometric processes and liquid chromatogram measuring reaction.
The reaction, isopropylbenzene conversion ratio are that the selectivity of 30.26%, 2- phenyl -2- propyl alcohol is 89.79%, and yield is
27.20%.
Embodiment 8
(1) by 30mL isopropylbenzene, 12mg PORPHYRIN IRON is added in three neck round bottom flask, is passed through oxygen with the rate of 10mL/min
Gas, sets reaction temperature as 20 DEG C, reaction time 10h.
(2) with the content of each substance after indirect iodometric processes and liquid chromatogram measuring reaction.
The reaction, isopropylbenzene conversion ratio are that the selectivity of 14.65%, 2- phenyl -2- propyl alcohol is 90.61%, and yield is
13.27%.
Embodiment 9
(1) by 30mL isopropylbenzene, 12mg is added in three neck round bottom flask chlorine PORPHYRIN IRON, 100mg dibenzothiophenes, with
The rate of 10mL/min is passed through oxygen, and reaction temperature is 80 DEG C, reaction time 10h.
(2) with the content of each substance after indirect iodometric processes and liquid chromatogram measuring reaction.
The reaction, isopropylbenzene conversion ratio are that the selectivity of 40.08%, 2- phenyl -2- propyl alcohol is 86.24%, and yield is
34.57%.
Embodiment 10
(1) by 30mL isopropylbenzene, 12mg is added in three neck round bottom flask chlorine PORPHYRIN IRON, logical with the rate of 10mL/min
Enter oxygen, reaction temperature is 80 DEG C, reaction time 10h.
(2) with the content of each substance after indirect iodometric processes and liquid chromatogram measuring reaction.
The reaction, isopropylbenzene conversion ratio are that the selectivity of 29.51%, 2- phenyl -2- propyl alcohol is 87.13%, and yield is
25.72%.
Embodiment 11
(1) by 30mL isopropylbenzene, 12mg is added in three neck round bottom flask chlorine PORPHYRIN IRON, 100mg dibenzothiophenes, with
The rate of 10mL/min is passed through oxygen, and reaction temperature is 80 DEG C, reaction time 5h.
(2) with the content of each substance after indirect iodometric processes and liquid chromatogram measuring reaction.
The reaction, isopropylbenzene conversion ratio are that the selectivity of 24.40%, 2- phenyl -2- propyl alcohol is 78.99%, and yield is
16.90%.
Embodiment 12
(1) by 30mL isopropylbenzene, 12mg is added in three neck round bottom flask chlorine PORPHYRIN IRON, logical with the rate of 10mL/min
Enter oxygen, reaction temperature is 80 DEG C, reaction time 5h.
(2) with the content of each substance after indirect iodometric processes and liquid chromatogram measuring reaction.
The reaction, isopropylbenzene conversion ratio are that the selectivity of 15.51%, 2- phenyl -2- propyl alcohol is 80.56%, and yield is
12.49%.
Embodiment 13
(1) by 30mL isopropylbenzene, 12mg is added in three neck round bottom flask chlorine Manganese Porphyrin, 100mg dibenzothiophenes, with
The rate of 10mL/min is passed through oxygen, and reaction temperature is 80 DEG C, reaction time 12h.
(2) with the content of each substance after indirect iodometric processes and liquid chromatogram measuring reaction.
The reaction, isopropylbenzene conversion ratio are that the selectivity of 41.67%, 2- phenyl -2- propyl alcohol is 84.65%, and yield is
35.28%.
Embodiment 14
(1) by 30mL isopropylbenzene, 12mg is added in three neck round bottom flask chlorine Manganese Porphyrin, logical with the rate of 10mL/min
Enter oxygen, reaction temperature is 80 DEG C, reaction time 12h.
(2) with the content of each substance after indirect iodometric processes and liquid chromatogram measuring reaction.
The reaction, isopropylbenzene conversion ratio are that the selectivity of 35.20%, 2- phenyl -2- propyl alcohol is 85.11%, and yield is
29.96%.
Embodiment 15
By 30mL methanol, 30mg Dibenzothiophene sulfoxide is added in three neck round bottom flask, 30 DEG C of reaction temperature, opens xenon
Lamp, reaction time 2h.
The amount of each substance after being reacted with liquid chromatogram measuring
The reaction, the conversion ratio of Dibenzothiophene sulfoxide are 99%, and the yield of dibenzothiophenes is 95%.
Claims (9)
1. a kind of preparation method of 2- phenyl -2- propyl alcohol, which is characterized in that isopropylbenzene and oxygen are in the presence of a catalyst through being catalyzed
2- phenyl -2- propyl alcohol is made in oxidation reaction, wherein the catalyst is porphyrin catalyst, is added in the catalytic oxidation
Enter dibenzothiophenes to be used as recycled material.
2. preparation method according to claim 1, which is characterized in that isopropylbenzene and oxygen are in the presence of illumination, catalyst
2- phenyl -2- propyl alcohol is made through catalytic oxidation, wherein the illumination is xenon light, and the catalyst is porphyrin catalyst,
Dibenzothiophenes is added in the catalytic oxidation to be used as recycled material.
3. preparation method according to claim 2, which is characterized in that the reaction temperature of the catalytic oxidation be 20~
80 DEG C, the reaction time is 5~17h.
4. preparation method according to claim 1, which is characterized in that the reaction temperature of the catalytic oxidation be 20~
120 DEG C, the reaction time is 5~17h.
5. preparation method according to claim 1 or 2, which is characterized in that the porphyrin catalyst and isopropylbenzene quality
Than for 0.2~0.5mg:1g.
6. preparation method according to claim 1 or 2, which is characterized in that the dibenzothiophenes and isopropylbenzene mass ratio
For 3~20mg:1g.
7. preparation method according to claim 1 or 2, which is characterized in that the addition rate of the oxygen be 2~
20mL/min。
8. preparation method according to claim 1 or 2, which is characterized in that the intensity of the xenon light is 200~500W.
9. preparation method according to claim 1 or 2, which is characterized in that the porphyrin catalyst is metalloporphyrin.
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| CN110423185A (en) * | 2019-08-28 | 2019-11-08 | 浙江工业大学 | A kind of method of isopropyl benzene-like compounds selective oxidation |
| 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 |
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| CN101301627A (en) * | 2008-06-13 | 2008-11-12 | 大连理工大学 | Method for bionically catalyzing and oxidizing thiophen compounds |
| CN103058821A (en) * | 2012-12-20 | 2013-04-24 | 华南理工大学 | Synthesis method of 2-phenyl-2-propanol and acetophenone through catalytic oxidation of cumene |
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| CN110423185A (en) * | 2019-08-28 | 2019-11-08 | 浙江工业大学 | A kind of method of isopropyl benzene-like compounds selective oxidation |
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| 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 |
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