CN103159592B - The production method of two-(2-hydroxyisopropyl) benzene - Google Patents
The production method of two-(2-hydroxyisopropyl) benzene Download PDFInfo
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- CN103159592B CN103159592B CN201110409653.1A CN201110409653A CN103159592B CN 103159592 B CN103159592 B CN 103159592B CN 201110409653 A CN201110409653 A CN 201110409653A CN 103159592 B CN103159592 B CN 103159592B
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Abstract
The present invention relates to a kind of production method of two-(2-hydroxyisopropyl) benzene, mainly solve prior art and there is impurity ethanoyl dimethyl benzyl alcohol in reuse diisopropylbenzene(DIPB) and constantly accumulate, affect the problem of oxidizing reaction speed.The present invention is comprised the following steps by employing: be a) 85 ~ 105 DEG C in temperature of reaction, reaction pressure is under 0.20 ~ 0.35MPa condition, containing the stream I of diisopropylbenzene(DIPB) and air and catalyst exposure, oxidizing reaction 10 ~ 24 hours occurs, obtains stream I I; Wherein, in stream I, the weight content of ethanoyl dimethyl benzyl alcohol is less than 3%; B) be 85 ~ 105 DEG C in temperature of reaction, reaction pressure is under 0.20 ~ 0.35MPa condition, stream I I and reductive agent Na
2there are reduction reaction 5 ~ 7 hours in S, the technical scheme obtaining two-(2-hydroxyisopropyl) benzene solves this problem preferably, can be used in the industrial production of two-(2-hydroxyisopropyl) benzene.
Description
Technical field
The present invention relates to a kind of production method of two-(2-hydroxyisopropyl) benzene.
Background technology
Two-(2-hydroxyisopropyl) benzene are a kind of important chemical industry intermediate raw materials, and be called for short DC, molecular formula is C
12h
18o
2, molecular weight is 194.28.Under normal temperature, DC is a kind of white, needle-shaped crystals solid, and the fusing point of a position isomers is 134 ~ 135 DEG C, contraposition be 140 ~ 141 DEG C.The chemical property of DC is also comparatively active, and as tertiary carbon alcohol, DC (is greater than 120 DEG C) at relatively high temperatures, and dehydration becomes alkene.DC itself can be polymerized, and also can react with tertbutyl peroxide etc. and generate various organic compound.Just based on these character of DC, DC is being the stablizer xenol of synthesis of polyolefins, urethane, is again the important starting raw material of organo-peroxide two (tert-butyl peroxy sec.-propyl) benzene and aromatic hydrocarbons diamines.
The preparation method of two-(2-hydroxyisopropyl) benzene is for raw material with diisopropylbenzene(DIPB) (DIPB), NaOH solution is adopted to make catalyzer, by air, diisopropylbenzene(DIPB) is oxidized to the diisopropylbenzene(DIPB) solution (hereinafter referred to as oxidation solution) of diisopropylbenzene(DIPB) list hydroperoxide (MHP) and diisopropylbenzene(DIPB) dihydro-peroxidase (DHP), the obtained DC of oxidation solution reduction.Wherein, oxidation reaction process is as follows:
main reaction (1)
side reaction (1-1)
side reaction (1-2)
Reduction reaction process is as follows:
main reaction (2)
side reaction (2-1)
side reaction (2-2)
Diisopropylbenzene(DIPB) is the chief component of oxidation solution, needs to repeat reuse again and again in industrial installation, and the isopropyl benzene hexanone (MKT), the CH that produce in reaction process
3oH, ethanoyl isopropyl benzene hydroperoxide (KHP) and ethanoyl dimethyl benzyl alcohol (KC) by product are also accumulated in oxidation solution.In these by products, MKT, KHP and CH
3oH can be dissolved in alkaline solution, is removed by intermittently discharged spent caustic solution.And KC is insoluble to alkaline solution, constantly accumulate in system, affect oxidizing reaction speed.Therefore the KC content controlled in reuse diisopropylbenzene(DIPB) is vital.And the KC that will remove in diisopropylbenzene(DIPB), document GB1441778 disclose with 50 ~ 80% methanol aqueous solutions or aqueous ethanolic solution removal impurity KC, by the test of the present inventor, removal effect is unsatisfactory, and clearance is only 10%; And methyl alcohol, ethanol are dissolved in system, also must be removed by distillation, remove technique more complicated.
Summary of the invention
Technical problem to be solved by this invention there is impurity ethanoyl dimethyl benzyl alcohol in reuse diisopropylbenzene(DIPB) in prior art constantly to accumulate, and affects the problem of oxidizing reaction speed, provides a kind of production method of two-(2-hydroxyisopropyl) benzene newly.The method has the advantages that to improve oxidizing reaction speed.
For solving the problems of the technologies described above, the technical solution used in the present invention is as follows: a kind of production method of two-(2-hydroxyisopropyl) benzene, comprises the following steps:
A) be 85 ~ 105 DEG C in temperature of reaction, reaction pressure is under 0.20 ~ 0.35MPa condition, containing the stream I of diisopropylbenzene(DIPB) and air and catalyst exposure, oxidizing reaction 10 ~ 24 hours occurs, obtains stream I I; Wherein, described catalyzer be weight percentage concentration be 10 ~ 20% NaOH solution, the weight ratio of NaOH solution and stream I is (8 ~ 10): 1, and the weight ratio of stream I and air is (2 ~ 3): 1, and in stream I, the weight content of ethanoyl dimethyl benzyl alcohol is less than 3%;
B) be 85 ~ 105 DEG C in temperature of reaction, reaction pressure is under 0.20 ~ 0.35MPa condition, stream I I and reductive agent Na
2there are reduction reaction 5 ~ 7 hours in S, obtains two-(2-hydroxyisopropyl) benzene; Wherein, the consumption of reductive agent and the mol ratio of diisopropylbenzene(DIPB) list hydroperoxide are (4.10 ~ 4.80): 1.
In technique scheme, in stream I, the weight content preferable range of ethanoyl dimethyl benzyl alcohol is 0.01 ~ 2.5%, and more preferably scope is 0.5 ~ 1.5%.
In the inventive method, if the weight content of ethanoyl dimethyl benzyl alcohol KC is not less than 3% in stream I, then stream I can first fully contact with hypochlorite solutions, gets rid of aqueous phase after stratification, the oil phase obtained again with oxygen reaction.Wherein, Contact Temperature is 20 ~ 60 DEG C, and preferable range is 40 ~ 50 DEG C; Duration of contact is 0.5 ~ 10 hour, and preferable range is 1 ~ 4 hour; The weight percent concentration of hypochlorite solutions is 5 ~ 20%; The weight ratio of diisopropylbenzene(DIPB) and hypochlorite solutions is 1: (0.8 ~ 1.5), and preferable range is 1: (0.9 ~ 1).Hypochlorite is selected from least one in clorox, Losantin or potassium hypochlorite, and preferred version is for being selected from clorox.Pass through the method; diisopropylbenzene(DIPB) containing ethanoyl dimethyl benzyl alcohol KC is fully contacted with hypochlorite solutions; the reaction product of ethanoyl dimethyl benzyl alcohol and hypochlorite is water-soluble; water oil two-phase is defined after leaving standstill; after being separated lower floor's aqueous phase; oil phase is the diisopropylbenzene(DIPB) logistics met the demands, and the clearance of ethanoyl dimethyl benzyl alcohol KC can up to 89.5%.
The reaction that impurity ethanoyl dimethyl benzyl alcohol KC and hypochlorite occur is as follows:
The inventive method is less than 3% by the weight content controlling ethanoyl dimethyl benzyl alcohol in reuse diisopropylbenzene(DIPB), and oxidizing reaction speed can improve 3 ~ 5 times, thus improves the speed of whole reaction process, achieves good technique effect.
In the inventive method, oxidation rate judges with MHP content in oxidation solution.MHP content increases faster, illustrates that oxidation rate is faster.
Below by embodiment, the invention will be further elaborated.
Embodiment
[embodiment 1 ~ 7]
Reuse diisopropylbenzene(DIPB) stream I II containing KC is fully contacted with chlorine bleach liquor, gets rid of aqueous phase after stratification, be namely met the diisopropylbenzene(DIPB) stream I of requirement.Wherein, the weight percent concentration of chlorine bleach liquor is 10%.The weight ratio of Contact Temperature, duration of contact, diisopropylbenzene(DIPB) stream I II and hypochlorite solutions, process the content of KC in the first two cumene stream III, and clearance is specifically in table 1.
Table 1
[comparative example 1 ~ 3]
With [embodiment 1 ~ 8], just replace chlorine bleach liquor with 50%NaOH solution, the methanol solution of 50%, the ethanolic soln of 50% respectively, the results are shown in Table 2.
Table 2
[embodiment 8]
The reuse diisopropylbenzene(DIPB) being stripped of KC processed through [embodiment 4] and air are carried out oxidizing reaction, then carries out reduction reaction with reductive agent, obtain two-(2-hydroxyisopropyl) benzene.
Wherein, oxidizing reaction temperature is 100 DEG C, and reaction pressure is 0.25MPa, and the reaction times is 24 hours, and the weight ratio of diisopropylbenzene(DIPB) and air is 3: 1.Reduction reaction temperature is 65 DEG C, and reaction pressure is normal pressure, and the reaction times is 6 hours, and the mol ratio of reductive agent and MHP is 4.60: 1.
MHP initial content is 2%, and oxidizing reaction is after 24 hours, and MHP content is 30.31%.
[comparative example 4]
With [embodiment 8], just diisopropylbenzene(DIPB) does not remove KC, and the content of KC is 7.296%.Oxidizing reaction is after 24 hours, and MHP content is only 7.95%.
As can be seen here, the content that must control KC in reuse diisopropylbenzene(DIPB) is less than 3%.
Claims (3)
1. a production method for two-(2-hydroxyisopropyl) benzene, comprises the following steps:
A) be 85 ~ 105 DEG C in temperature of reaction, reaction pressure is under 0.20 ~ 0.35MPa condition, containing the logistics I of diisopropylbenzene(DIPB) and air and catalyst exposure, oxidizing reaction 10 ~ 24 hours occurs, obtains logistics II; Wherein, described catalyzer be weight percentage concentration be 10 ~ 20% NaOH solution, the weight ratio of NaOH solution and logistics I is (8 ~ 10): 1, logistics I is (2 ~ 3) with the weight ratio of air: 1, and in logistics I, the weight content of ethanoyl dimethyl benzyl alcohol is less than 3%;
B) be 85 ~ 105 DEG C in temperature of reaction, reaction pressure is under 0.20 ~ 0.35MPa condition, logistics II and reductive agent Na
2there are reduction reaction 5 ~ 7 hours in S, obtains two-(2-hydroxyisopropyl) benzene; Wherein, the consumption of reductive agent and the mol ratio of diisopropylbenzene(DIPB) list hydroperoxide are (4.10 ~ 4.80): 1;
Wherein, the treatment process making the weight content of ethanoyl dimethyl benzyl alcohol in logistics I be less than 3% is: logistics I first fully contacts with hypochlorite solutions, gets rid of aqueous phase after stratification, the oil phase obtained again with oxygen reaction; Wherein, Contact Temperature is 20 ~ 60 DEG C, and duration of contact is 0.5 ~ 10 hour; The weight percent concentration of hypochlorite solutions is 5 ~ 20%; The weight ratio of diisopropylbenzene(DIPB) and hypochlorite solutions is 1:(0.8 ~ 1.5); Hypochlorite is selected from least one in clorox, Losantin or potassium hypochlorite.
2. the production method of two-(2-hydroxyisopropyl) benzene according to claim 1, is characterized in that the weight content of ethanoyl dimethyl benzyl alcohol in logistics I is 0.01 ~ 2.5%.
3. the production method of two-(2-hydroxyisopropyl) benzene according to claim 1, is characterized in that the weight content of ethanoyl dimethyl benzyl alcohol in logistics I is 0.5 ~ 1.5%.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103396292B (en) * | 2013-08-09 | 2015-04-01 | 宁波朝日精细化工有限公司 | Method for industrially producing A,A'-dihydroxy-1,3-diisobutylbenzene |
| CN104418706B (en) * | 2013-09-10 | 2016-08-10 | 中国石油化工集团公司 | The process for purification of two (2-hydroxyisopropyl) benzene |
| CN104418782A (en) * | 2013-09-10 | 2015-03-18 | 中国石油化工集团公司 | Method for preparing hydroperoxide mixture through diisopropylbenzene oxidation |
| CN107652164A (en) * | 2017-10-12 | 2018-02-02 | 江苏道明化学有限公司 | A kind of production method of diisopropylbenzene (DIPB) alcohol |
| CN108929257A (en) * | 2018-05-30 | 2018-12-04 | 浙江道明化学有限公司 | A kind of chemical synthesis process of organic peroxide |
| JP7493942B2 (en) * | 2020-01-10 | 2024-06-03 | 住友化学株式会社 | Method for producing bis(2-hydroxy-2-propyl)benzene |
| CN115583904B (en) * | 2021-07-05 | 2024-05-28 | 中国石油化工股份有限公司 | Treatment method and recycling method of m-diisopropylbenzene reduction mother liquor |
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| US4053520A (en) * | 1970-05-04 | 1977-10-11 | The Goodyear Tire & Rubber Company | Production of para-dialkylbenzene dihydroperoxide |
| CN1093352A (en) * | 1993-03-31 | 1994-10-12 | 兰州大学 | The manufacture method of 2-phenyl-2-propyl alcohol |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4053520A (en) * | 1970-05-04 | 1977-10-11 | The Goodyear Tire & Rubber Company | Production of para-dialkylbenzene dihydroperoxide |
| CN1093352A (en) * | 1993-03-31 | 1994-10-12 | 兰州大学 | The manufacture method of 2-phenyl-2-propyl alcohol |
Non-Patent Citations (1)
| Title |
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| 二-(2-羟基异丙基)苯的制备;徐裕 等;《高桥石化》;20010228;第16卷(第1期);第12-14、34页 * |
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