CN102911014A - Di-(2-hydroxyl isopropyl) benzene production method - Google Patents
Di-(2-hydroxyl isopropyl) benzene production method Download PDFInfo
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- CN102911014A CN102911014A CN2011102214872A CN201110221487A CN102911014A CN 102911014 A CN102911014 A CN 102911014A CN 2011102214872 A CN2011102214872 A CN 2011102214872A CN 201110221487 A CN201110221487 A CN 201110221487A CN 102911014 A CN102911014 A CN 102911014A
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- CN
- China
- Prior art keywords
- benzene
- propyl
- sec
- hydrogen peroxide
- hydroxyl
- 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.)
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title claims abstract description 153
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Substances OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 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 claims abstract description 10
- DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 6
- FGRVOLIFQGXPCT-UHFFFAOYSA-L dipotassium;dioxido-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound [K+].[K+].[O-]S([O-])(=O)=S FGRVOLIFQGXPCT-UHFFFAOYSA-L 0.000 claims abstract description 4
- ZOCLAPYLSUCOGI-UHFFFAOYSA-M potassium hydrosulfide Chemical compound [SH-].[K+] ZOCLAPYLSUCOGI-UHFFFAOYSA-M 0.000 claims abstract description 4
- 230000002829 reductive effect Effects 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 101000648997 Homo sapiens Tripartite motif-containing protein 44 Proteins 0.000 claims description 9
- 102100028017 Tripartite motif-containing protein 44 Human genes 0.000 claims description 9
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 6
- PODWXQQNRWNDGD-UHFFFAOYSA-L sodium thiosulfate pentahydrate Chemical compound O.O.O.O.O.[Na+].[Na+].[O-]S([S-])(=O)=O PODWXQQNRWNDGD-UHFFFAOYSA-L 0.000 claims description 6
- IHYNKGRWCDKNEG-UHFFFAOYSA-N n-(4-bromophenyl)-2,6-dihydroxybenzamide Chemical compound OC1=CC=CC(O)=C1C(=O)NC1=CC=C(Br)C=C1 IHYNKGRWCDKNEG-UHFFFAOYSA-N 0.000 claims description 3
- 235000010265 sodium sulphite Nutrition 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 abstract 3
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 abstract 1
- 229910052979 sodium sulfide Inorganic materials 0.000 abstract 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 abstract 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 abstract 1
- 235000019345 sodium thiosulphate Nutrition 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 8
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 8
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 8
- 238000006722 reduction reaction Methods 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000010977 unit operation Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a di-(2-hydroxyl isopropyl) benzene production method which mainly solves the problems of long technical process and excessive public project consumption in the prior art. The technical scheme for better solving the problems includes that diisopropylbenzene oxidant solution containing di-(hydrogen peroxide isopropyl) benzene is used as a raw material to obtain the di-(2-hydroxyl isopropyl) benzene by means of reaction of the di-(hydrogen peroxide isopropyl) benzene and reducing agent, wherein the reaction temperature is 40-200 DEG C, the reaction pressure is 0.2-1.0MPa, the reducing agent is selected from at least one of sodium thiosulfate , potassium thiosulfate, potassium sulfide, potassium hydrosulfide, sodium sulfide or sodium hydrosulfide, and the weight ratio of the di-(hydrogen peroxide isopropyl) benzene to the reducing agent is (1-30):(1-20). The di-(2-hydroxyl isopropyl) benzene production method can be used for industrial production of di-(2-hydroxyl isopropyl) benzene.
Description
Technical field
The present invention relates to a kind of method of production two-(2-hydroxyl sec.-propyl) benzene.
Background technology
Two-(2-hydroxyl sec.-propyl) benzene (DC) are the intermediates of producing two-(tert-butyl peroxy sec.-propyl) benzene (BIPB).Document US 7557252 " Process for Producing Dihydroxybenzene and Diisopropylbenzenedicarbinol " discloses the diisopropylbenzene(DIPB) oxidation solution of-(hydrogen peroxide sec.-propyl) benzene (DHP) two to contain as raw material, extract two-(hydrogen peroxide sec.-propyl) benzene with methyl iso-butyl ketone (MIBK), then carry out decomposition reaction, carry out hydrogenation reduction, crystallization makes two-(2-hydroxyl sec.-propyl) benzene in methyl iso-butyl ketone (MIBK) at last again.
But the technological process for preparing two-(2-hydroxyl sec.-propyl) benzene in the above-mentioned document adopts four unit operation steps such as extraction, decomposition, reduction, crystallization, has the problem that technical process is long, general facilities consumption is many.
Summary of the invention
Technical problem to be solved by this invention is that prior art exists the problem that technical process is long, general facilities consumption is many, and the method for a kind of new production two-(2-hydroxyl sec.-propyl) benzene is provided.It is simple that the method has technical process, and general facilities consumes low characteristics.
For solving the problems of the technologies described above, the technical solution used in the present invention is as follows: a kind of method of production two-(2-hydroxyl sec.-propyl) benzene, the diisopropylbenzene(DIPB) oxidation solution of-(hydrogen peroxide sec.-propyl) benzene two to contain is as raw material, 40～200 ℃ of temperature of reaction, under reaction pressure 0.2～1.0MPa condition, two-(hydrogen peroxide sec.-propyl) benzene and reductive agent reaction obtain two-(2-hydroxyl sec.-propyl) benzene; Wherein said reductive agent be selected from Sulfothiorine, Potassium Thiosulphate, potassium sulphide, potassium hydrogen sulfide, sodium sulphite or the sodium bisulfide at least a, two-weight ratio of (hydrogen peroxide sec.-propyl) benzene and reductive agent is (1～30): (1～20).
In the technique scheme, the temperature of reaction preferable range is 120～180 ℃, and the reaction pressure preferable range is 0.7～0.8MPa.The weight ratio of two-(hydrogen peroxide sec.-propyl) benzene and reductive agent is that preferable range is (7～20): (5～15).Described reductive agent preferred version is to be selected from least a in Sulfothiorine or the potassium sulphide.Contain in the diisopropylbenzene(DIPB) oxidation solution of two-(hydrogen peroxide sec.-propyl) benzene, the content of two-(hydrogen peroxide sec.-propyl) benzene is 10～20 % by weight.
In the inventive method, described reaction pressure all refers to gauge pressure.
The inventive method need not to extract and decomposition course, be selected from least a for reductive agent in Sulfothiorine, Potassium Thiosulphate, potassium sulphide, potassium hydrogen sulfide, sodium sulphite or the sodium bisulfide by employing, diisopropylbenzene(DIPB) oxidation solution and the reductive agent generation reduction reaction that directly will contain two-(hydrogen peroxide sec.-propyl) benzene, just can obtain two-(2-hydroxyl sec.-propyl) benzene, simplify technical process, reduced the consumption of general facilities.Adopt the inventive method, the refrigerated water consumption of producing 1 ton two-(2-hydroxyl sec.-propyl) benzene DC drops to 40 tons of the present invention by 50 tons of prior art, recirculated water consumption drops to 280 tons of the present invention by 350 tons of prior art, steam consumption drops to 3.1 tons of the present invention by 4.0 tons of prior art, power consumption drops to 375kWh of the present invention by the 450kWh of prior art, has obtained preferably technique effect.
The present invention is further elaborated below by embodiment.
Embodiment
[embodiment 1]
Take contain 15.33 % by weight two-the diisopropylbenzene(DIPB) oxidation solution of (hydrogen peroxide sec.-propyl) benzene DHP is as raw material, 180 ℃ of temperature of reaction, under the reaction pressure 0.8MPa condition, two-(hydrogen peroxide sec.-propyl) benzene and reductive agent reaction obtain two-(2-hydroxyl sec.-propyl) benzene; Wherein, the weight ratio of two-(hydrogen peroxide sec.-propyl) benzene and reductive agent Sulfothiorine is 10: 7.
General facilities consumption is: refrigerated water consumes 40 tons of/ton DC, and recirculated water consumes 280 tons of/ton DC, 3.1 tons of/ton DC of steam consumption, power consumption 375kWh/ ton DC.
[embodiment 2]
With [embodiment 1], just reductive agent is potassium sulphide, and the weight ratio of two-(hydrogen peroxide sec.-propyl) benzene and potassium sulphide is 10: 8.
General facilities consumption is: refrigerated water consumes 39 tons of/ton DC, and recirculated water consumes 275 tons of/ton DC, 3.0 tons of/ton DC of steam consumption, power consumption 365kWh/ ton DC.
[embodiment 3]
With [embodiment 1], just temperature of reaction is 120 ℃, reaction pressure 0.7MPa.
General facilities consumption is: refrigerated water consumes 41 tons of/ton DC, and recirculated water consumes 287 tons of/ton DC, 3.2 tons of/ton DC of steam consumption, power consumption 388kWh/ ton DC.
[comparative example 1]
Produce two-(2-hydroxyl sec.-propyl) benzene according to document US 7557252 disclosed methods, its technological process adopts four unit operation steps such as extraction, decomposition, reduction, crystallization.
Take the oxidation solution of pure position diisopropylbenzene(DIPB) or pure contraposition diisopropylbenzene(DIPB) as raw material, at first extract two-(hydrogen peroxide sec.-propyl) benzene with methyl iso-butyl ketone (MIBK); Next two-(hydrogen peroxide sec.-propyl) benzene decomposes under acidic conditions and generation reduction reaction generation two-(2-hydroxyl sec.-propyl) benzene under the effect of reductive agent hydrogen, the temperature of its reduction reaction is 280 ℃, pressure is 3.0MPa, and hydrogen is 200: 1 with the volume ratio of two-(hydrogen peroxide sec.-propyl) benzene; Go out two-(2-hydroxyl sec.-propyl) benzene with the methyl iso-butyl ketone (MIBK) crystallization at last.
General facilities consumption is: refrigerated water consumes 50 tons of/ton DC, and recirculated water consumes 350 tons of/ton DC, 4.0 tons of/ton DC of steam consumption, power consumption 450kWh/ ton DC.
Claims (5)
1. method of producing two-(2-hydroxyl sec.-propyl) benzene, the diisopropylbenzene(DIPB) oxidation solution of-(hydrogen peroxide sec.-propyl) benzene two to contain is as raw material, 40～200 ℃ of temperature of reaction, under reaction pressure 0.2～1.0MPa condition, two-(hydrogen peroxide sec.-propyl) benzene and reductive agent reaction obtain two-(2-hydroxyl sec.-propyl) benzene; Wherein said reductive agent be selected from Sulfothiorine, Potassium Thiosulphate, potassium sulphide, potassium hydrogen sulfide, sodium sulphite or the sodium bisulfide at least a, two-weight ratio of (hydrogen peroxide sec.-propyl) benzene and reductive agent is (1～30): (1～20).
2. the method for according to claim 1 described production two-(2-hydroxyl sec.-propyl) benzene is characterized in that 120～180 ℃ of temperature of reaction, reaction pressure 0.7～0.8MPa.
3. the method for according to claim 1 described production two-(2-hydroxyl sec.-propyl) benzene is characterized in that the weight ratio of two-(hydrogen peroxide sec.-propyl) benzene and reductive agent is (7～20): (5～15).
4. the method for according to claim 1 described production two-(2-hydroxyl sec.-propyl) benzene is characterized in that described reductive agent is selected from least a in Sulfothiorine or the potassium sulphide.
5. the method for according to claim 1 described production two-(2-hydroxyl sec.-propyl) benzene is characterized in that containing in the diisopropylbenzene(DIPB) oxidation solution of two-(hydrogen peroxide sec.-propyl) benzene, and the content of two-(hydrogen peroxide sec.-propyl) benzene is 10～20 % by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110221487.2A CN102911014B (en) | 2011-08-04 | 2011-08-04 | Di-(2-hydroxyl isopropyl) benzene production method |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110221487.2A CN102911014B (en) | 2011-08-04 | 2011-08-04 | Di-(2-hydroxyl isopropyl) benzene production method |
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| Publication Number | Publication Date |
|---|---|
| CN102911014A true CN102911014A (en) | 2013-02-06 |
| CN102911014B CN102911014B (en) | 2015-04-08 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201110221487.2A Active CN102911014B (en) | 2011-08-04 | 2011-08-04 | Di-(2-hydroxyl isopropyl) benzene production method |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104909990A (en) * | 2015-05-07 | 2015-09-16 | 中石化上海工程有限公司 | Method for efficiently producing dicumyl peroxide (DCP) intermediate product |
| CN104909991A (en) * | 2015-05-07 | 2015-09-16 | 中石化上海工程有限公司 | Method for continuously producing dicumyl peroxide (DCP) intermediate product |
| CN112679317A (en) * | 2019-10-18 | 2021-04-20 | 中国石油化工股份有限公司 | Method for separating m-di- (2-hydroxyisopropyl) benzene and p-di- (2-hydroxyisopropyl) benzene |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3923908A (en) * | 1972-11-21 | 1975-12-02 | Sumitomo Chemical Co | Process for the preparation of hydroquinone and/or resorcinol by the cleavage of dihydroperoxides |
| US4322567A (en) * | 1979-06-18 | 1982-03-30 | Mitsui Petrochemical Industries Ltd. | Process for production of aromatic alcohols |
| JPS60174737A (en) * | 1984-02-22 | 1985-09-09 | Mitsui Petrochem Ind Ltd | Preparation of aromatic alcohol |
| CN1093352A (en) * | 1993-03-31 | 1994-10-12 | 兰州大学 | The manufacture method of 2-phenyl-2-propyl alcohol |
| US7557252B2 (en) * | 2006-02-17 | 2009-07-07 | Sumitomo Chemical Company, Limited | Process for producing dihydroxybenzene and diisopropylbenzendicarbinol |
-
2011
- 2011-08-04 CN CN201110221487.2A patent/CN102911014B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3923908A (en) * | 1972-11-21 | 1975-12-02 | Sumitomo Chemical Co | Process for the preparation of hydroquinone and/or resorcinol by the cleavage of dihydroperoxides |
| US4322567A (en) * | 1979-06-18 | 1982-03-30 | Mitsui Petrochemical Industries Ltd. | Process for production of aromatic alcohols |
| JPS60174737A (en) * | 1984-02-22 | 1985-09-09 | Mitsui Petrochem Ind Ltd | Preparation of aromatic alcohol |
| CN1093352A (en) * | 1993-03-31 | 1994-10-12 | 兰州大学 | The manufacture method of 2-phenyl-2-propyl alcohol |
| US7557252B2 (en) * | 2006-02-17 | 2009-07-07 | Sumitomo Chemical Company, Limited | Process for producing dihydroxybenzene and diisopropylbenzendicarbinol |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104909990A (en) * | 2015-05-07 | 2015-09-16 | 中石化上海工程有限公司 | Method for efficiently producing dicumyl peroxide (DCP) intermediate product |
| CN104909991A (en) * | 2015-05-07 | 2015-09-16 | 中石化上海工程有限公司 | Method for continuously producing dicumyl peroxide (DCP) intermediate product |
| CN104909990B (en) * | 2015-05-07 | 2016-08-24 | 中石化上海工程有限公司 | The method efficiently producing cumyl peroxide DCP intermediate products |
| CN112679317A (en) * | 2019-10-18 | 2021-04-20 | 中国石油化工股份有限公司 | Method for separating m-di- (2-hydroxyisopropyl) benzene and p-di- (2-hydroxyisopropyl) benzene |
| CN112679317B (en) * | 2019-10-18 | 2023-01-24 | 中国石油化工股份有限公司 | Method for separating m-di- (2-hydroxyisopropyl) benzene and p-di- (2-hydroxyisopropyl) benzene |
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| CN102911014B (en) | 2015-04-08 |
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