CN103159585A - Method for removing acetyl dimethyl-benzyl alcohol from diisopropylbenzene - Google Patents
Method for removing acetyl dimethyl-benzyl alcohol from diisopropylbenzene Download PDFInfo
- Publication number
- CN103159585A CN103159585A CN2011104096480A CN201110409648A CN103159585A CN 103159585 A CN103159585 A CN 103159585A CN 2011104096480 A CN2011104096480 A CN 2011104096480A CN 201110409648 A CN201110409648 A CN 201110409648A CN 103159585 A CN103159585 A CN 103159585A
- Authority
- CN
- China
- Prior art keywords
- diisopropylbenzene
- benzyl alcohol
- dipb
- dimethyl benzyl
- stream
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 title claims abstract description 62
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 title claims abstract description 42
- -1 acetyl dimethyl-benzyl Chemical group 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 22
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims abstract description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 28
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 4
- SATVIFGJTRRDQU-UHFFFAOYSA-N potassium hypochlorite Chemical compound [K+].Cl[O-] SATVIFGJTRRDQU-UHFFFAOYSA-N 0.000 claims description 2
- 101000648997 Homo sapiens Tripartite motif-containing protein 44 Proteins 0.000 claims 13
- 102100028017 Tripartite motif-containing protein 44 Human genes 0.000 claims 13
- 239000012535 impurity Substances 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract 4
- 238000009776 industrial production Methods 0.000 abstract 1
- 238000013517 stratification Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007844 bleaching agent Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YKTNISGZEGZHIS-UHFFFAOYSA-N 2-$l^{1}-oxidanyloxy-2-methylpropane Chemical group CC(C)(C)O[O] YKTNISGZEGZHIS-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- GTZAKYBBIKAFOY-UHFFFAOYSA-N hydrogen peroxide 1-(2-propan-2-ylphenyl)ethanone Chemical compound OO.CC(C)C1=CC=CC=C1C(C)=O GTZAKYBBIKAFOY-UHFFFAOYSA-N 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for removing acetyl dimethyl-benzyl alcohol from diisopropylbenzene, and mainly solves the problem of low removal rate of impurity acetyl dimethyl-benzyl alcohol in diisopropylbenzene in the prior art. The problem is relatively well solved by a technical solution comprising the steps of fully contacting a diisopropylbenzene material flow I containing the acetyl dimethyl-benzyl alcohol with a hypochlorite solution at a temperature of 20-60 DEG C, standing, removing a water phase after stratification to obtain a diisopropylbenzene material flow II, wherein the weight content of the acetyl dimethyl-benzyl alcohol in the material flow I is smaller than 3%; a weight percentage concentration of the hypochlorite solution is 5-20%; and a weight ratio of the diisopropylbenzene material flow I to the hypochlorite solution is 1 : (0.8-1.5). The method can be applied in industrial production for removing acetyl dimethyl-benzyl alcohol from reused diisopropylbenzene.
Description
Technical field
The present invention relates to a kind of method that removes ethanoyl dimethyl benzyl alcohol in diisopropylbenzene(DIPB).
Background technology
Two-(2-hydroxyl sec.-propyl) benzene are a kind of important chemical industry intermediate raw materials, are called for short DC, and 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 ℃, contraposition be 140～141 ℃.The chemical property of DC is also comparatively active, and as tertiary carbon alcohol, DC (greater than 120 ℃) dehydration under comparatively high temps becomes alkene.DC itself can polymerization, also can generate various organic compound with the reaction such as tertbutyl peroxide.Just based on these character of DC, DC is 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-hydroxyl sec.-propyl) benzene is take diisopropylbenzene(DIPB) (DIPB) as raw material, by air, diisopropylbenzene(DIPB) is oxidized to the diisopropylbenzene(DIPB) solution (hereinafter to be referred as oxidation solution) of diisopropylbenzene(DIPB) list hydroperoxide (MHP) and diisopropylbenzene(DIPB) dihydro-peroxidase (DHP), the oxidation solution reduction makes DC.Wherein, oxidation reaction process is as follows:
Main reaction (1)
The reduction reaction process is as follows:
Side reaction (2-2)
Diisopropylbenzene(DIPB) is the chief component of oxidation solution, needs to repeat again and again reuse 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 also are accumulated in oxidation solution.In these by products, MKT, KHP and CH
3OH can be dissolved in alkaline solution, removes by the intermittently discharged spent caustic solution; And KC is insoluble to alkaline solution, and constantly accumulation, affect oxidizing reaction speed in system.Document GB1441778 discloses with 50～80% methanol aqueous solutions or aqueous ethanolic solution and has removed impurity ethanoyl dimethyl benzyl alcohol, and by human experimentation of the present invention, removal effect is unsatisfactory, and clearance is only 10%; And methyl alcohol, ethanol are dissolved in system, also must remove by distillation, remove technique more complicated.
Summary of the invention
Technical problem to be solved by this invention is to have the low problem of impurity ethanoyl dimethyl benzyl alcohol KC clearance in the reuse diisopropylbenzene(DIPB) in prior art, and a kind of new method that removes ethanoyl dimethyl benzyl alcohol in the reuse diisopropylbenzene(DIPB) is provided.The method has the high characteristics of impurity ethanoyl dimethyl benzyl alcohol clearance.
For solving the problems of the technologies described above, the technical solution used in the present invention is as follows: a kind of method that removes ethanoyl dimethyl benzyl alcohol in diisopropylbenzene(DIPB), be under 20～60 ℃ of conditions in temperature, the diisopropylbenzene(DIPB) stream I that contains the ethanoyl dimethyl benzyl alcohol is fully contacted with hypochlorite solutions, get rid of water after standing demix and obtain diisopropylbenzene(DIPB) stream I I, in stream I I, the weight content of ethanoyl dimethyl benzyl alcohol is less than 3%; Wherein, the weight percent concentration of hypochlorite solutions is 5～20%, and the weight ratio of diisopropylbenzene(DIPB) stream I and hypochlorite solutions is 1: (0.8～1.5).
In technique scheme, in the diisopropylbenzene(DIPB) stream I, the weight content of ethanoyl dimethyl benzyl alcohol is 5～10%.The weight ratio preferable range of diisopropylbenzene(DIPB) stream I and hypochlorite is 1: (0.9～1).Described temperature preferable range is 40～50 ℃.Duration of contact, preferable range was 0.5～10 hour, and more preferably scope is 1～4 hour.Hypochlorite is selected from least a in clorox, Losantin or potassium hypochlorite, and preferred version is for being selected from clorox.
Adopt the inventive method; the diisopropylbenzene(DIPB) that contains ethanoyl dimethyl benzyl alcohol KC is fully contacted with hypochlorite solutions; the reaction product of ethanoyl dimethyl benzyl alcohol and hypochlorite is water-soluble; formed water oil two-phase after standing; after separating lower floor's water; oil phase is the diisopropylbenzene(DIPB) stream I I that meets the demands, and the clearance of ethanoyl dimethyl benzyl alcohol KC can up to 89.5%, have been obtained technique effect preferably.
The reaction that impurity ethanoyl dimethyl benzyl alcohol KC and hypochlorite occur is as follows:
The invention will be further elaborated below by embodiment.
Embodiment
[embodiment 1～8]
The diisopropylbenzene(DIPB) stream I that contains ethanoyl dimethyl benzyl alcohol KC is fully contacted with the chlorine bleach liquor, get rid of water after standing demix, namely be met the diisopropylbenzene(DIPB) stream I I of requirement.Wherein, chlorine bleach liquor's weight percent concentration is 10%.The content of ethanoyl dimethyl benzyl alcohol in the diisopropylbenzene(DIPB) stream I before the weight ratio of Contact Temperature, duration of contact, diisopropylbenzene(DIPB) stream I and hypochlorite solutions, processing, and clearance specifically sees Table 1.
Table 1
[comparative example 1～3]
With [embodiment 1～8], just replace the chlorine bleach liquor with 50%NaOH solution, 50% methanol solution, 50% ethanolic soln respectively, the results are shown in Table 1.
Claims (8)
1. method that removes ethanoyl dimethyl benzyl alcohol in diisopropylbenzene(DIPB), be under 20～60 ℃ of conditions in temperature, the diisopropylbenzene(DIPB) stream I that contains the ethanoyl dimethyl benzyl alcohol is fully contacted with hypochlorite solutions, get rid of water after standing demix and obtain diisopropylbenzene(DIPB) stream I I, in stream I I, the weight content of ethanoyl dimethyl benzyl alcohol is less than 3%; Wherein, the weight percent concentration of hypochlorite solutions is 5～20%, and the weight ratio of diisopropylbenzene(DIPB) stream I and hypochlorite solutions is 1: (0.8～1.5).
2. the method that removes ethanoyl dimethyl benzyl alcohol in diisopropylbenzene(DIPB) according to claim 1, the weight content that it is characterized in that ethanoyl dimethyl benzyl alcohol in the diisopropylbenzene(DIPB) stream I is 5～10%.
3. the method that removes ethanoyl dimethyl benzyl alcohol in diisopropylbenzene(DIPB) according to claim 1, the weight ratio that it is characterized in that diisopropylbenzene(DIPB) stream I and hypochlorite is 1: (0.9～1).
4. the method that removes ethanoyl dimethyl benzyl alcohol in diisopropylbenzene(DIPB) according to claim 1, is characterized in that described temperature is 40～50 ℃.
5. the method that removes ethanoyl dimethyl benzyl alcohol in diisopropylbenzene(DIPB) according to claim 1, is characterized in that be 0.5～10 hour duration of contact.
6. the method that removes ethanoyl dimethyl benzyl alcohol in diisopropylbenzene(DIPB) according to claim 5, is characterized in that be 1～4 hour duration of contact.
7. the method that removes ethanoyl dimethyl benzyl alcohol in diisopropylbenzene(DIPB) according to claim 1 is characterized in that hypochlorite is selected from least a in clorox, Losantin or potassium hypochlorite.
8. the method that removes ethanoyl dimethyl benzyl alcohol in diisopropylbenzene(DIPB) according to claim 7, is characterized in that hypochlorite is selected from clorox.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110409648.0A CN103159585B (en) | 2011-12-09 | 2011-12-09 | Remove the method for ethanoyl dimethyl benzyl alcohol in diisopropylbenzene(DIPB) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110409648.0A CN103159585B (en) | 2011-12-09 | 2011-12-09 | Remove the method for ethanoyl dimethyl benzyl alcohol in diisopropylbenzene(DIPB) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103159585A true CN103159585A (en) | 2013-06-19 |
| CN103159585B CN103159585B (en) | 2015-12-16 |
Family
ID=48583157
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110409648.0A Active CN103159585B (en) | 2011-12-09 | 2011-12-09 | Remove the method for ethanoyl dimethyl benzyl alcohol in diisopropylbenzene(DIPB) |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103159585B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115583904A (en) * | 2021-07-05 | 2023-01-10 | 中国石油化工股份有限公司 | Treatment method and recycling method of m-diisopropylbenzene reduction mother liquor |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1441778A (en) * | 1972-11-21 | 1976-07-07 | Sumitomo Chemical Co | Process for removing impurities from a mixture produced by the molecular oxygen oxidation of diisopropylbenzene to its dihydroperoxide |
| US3993696A (en) * | 1973-05-02 | 1976-11-23 | Sumitomo Chemical Company, Limited | Method for recovering hydroperoxide |
| CN101918343A (en) * | 2008-01-09 | 2010-12-15 | 环球油品公司 | Process for separating diisopropylbenzene (DIPB) and triisopropylbenzene (TIPB) from a feed comprising DIPB, TIPB, and polyalkylate heavies |
-
2011
- 2011-12-09 CN CN201110409648.0A patent/CN103159585B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1441778A (en) * | 1972-11-21 | 1976-07-07 | Sumitomo Chemical Co | Process for removing impurities from a mixture produced by the molecular oxygen oxidation of diisopropylbenzene to its dihydroperoxide |
| US3993696A (en) * | 1973-05-02 | 1976-11-23 | Sumitomo Chemical Company, Limited | Method for recovering hydroperoxide |
| CN101918343A (en) * | 2008-01-09 | 2010-12-15 | 环球油品公司 | Process for separating diisopropylbenzene (DIPB) and triisopropylbenzene (TIPB) from a feed comprising DIPB, TIPB, and polyalkylate heavies |
Non-Patent Citations (1)
| Title |
|---|
| 杨兆娟、张宏: "过氧化二异丙苯生产水洗工艺比较实验", 《青海大学学报》, vol. 21, no. 6, 31 December 2003 (2003-12-31), pages 38 - 39 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115583904A (en) * | 2021-07-05 | 2023-01-10 | 中国石油化工股份有限公司 | Treatment method and recycling method of m-diisopropylbenzene reduction mother liquor |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103159585B (en) | 2015-12-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103159592B (en) | The production method of two-(2-hydroxyisopropyl) benzene | |
| CN106397366B (en) | The purification process of propylene oxide | |
| WO2009080342A1 (en) | Purification of cumene | |
| EP2247535B1 (en) | Process for recovery of organic compounds from a wastewater stream | |
| CN106397361B (en) | The method for purifying 1,2- epoxy butane | |
| CN107286119A (en) | The process for purification of expoxy propane | |
| CN115583905B (en) | Preparation method of m-di-tert-butyl dicumyl peroxide | |
| CN103159585B (en) | Remove the method for ethanoyl dimethyl benzyl alcohol in diisopropylbenzene(DIPB) | |
| CN111601784A (en) | Method for decomposing phenolic by-products | |
| JP2016530264A (en) | Method for producing p-cymene | |
| RU2655160C2 (en) | Improvements relating to alkylene oxide production | |
| US10130896B2 (en) | Process for purifying hydrocarbons | |
| EP1367042B1 (en) | Process for the recovery of phenol and biphenols | |
| JP2016538263A (en) | Use of alkanesulfonic acids to prepare phenolic alcohols | |
| CN106518810B (en) | Method for purifying propylene oxide | |
| JP4996861B2 (en) | Method for purifying recovered phenols | |
| CN107286118A (en) | The refining plant of expoxy propane | |
| RU2619117C2 (en) | Method for producing alpha-methylstyrene from cumene | |
| US7763755B2 (en) | Method for producing dialkylhydroperoxybenzenes | |
| CN115583904B (en) | Treatment method and recycling method of m-diisopropylbenzene reduction mother liquor | |
| JP4545248B2 (en) | Method for producing phenols | |
| JP2005162710A (en) | Method for producing diisopropyl hydroperoxybenzene | |
| CN115583906A (en) | Treatment method and recycling method of m-diisopropylbenzene oxidation liquid and production method of resorcinol | |
| JP6616530B2 (en) | Method for purifying phenol | |
| JP4018307B2 (en) | Extraction and purification method of hydroperoxides |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |