CN1051541C - Prepn. method for 2-phenyl-2-propanol - Google Patents
Prepn. method for 2-phenyl-2-propanol Download PDFInfo
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- CN1051541C CN1051541C CN93104129A CN93104129A CN1051541C CN 1051541 C CN1051541 C CN 1051541C CN 93104129 A CN93104129 A CN 93104129A CN 93104129 A CN93104129 A CN 93104129A CN 1051541 C CN1051541 C CN 1051541C
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- CN
- China
- Prior art keywords
- reaction
- phenyl
- water
- propanol
- chp
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- 238000000034 method Methods 0.000 title claims description 9
- BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 title abstract 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract description 7
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- -1 2-phenyl-2-propyl Chemical group 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 238000006722 reduction reaction Methods 0.000 abstract description 11
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 230000036632 reaction speed Effects 0.000 abstract description 4
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 abstract description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 abstract 2
- 238000009776 industrial production Methods 0.000 abstract 2
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000010865 sewage Substances 0.000 abstract 1
- 230000002829 reductive effect Effects 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 7
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000002826 coolant Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 235000019600 saltiness Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical class [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明提供一种2－苯基－2－丙醇的制造方法。2－苯基－2－丙醇是工业化生产过氧化二异丙苯(简称DCP)的重要中间体。本发明提供的用硫化物还原异丙苯过氧化氢(CHP)制造2－苯基－2－丙醇的方法具有还原剂价廉易得和消耗量少、还原反应速度快、转化率和收得率高、反应条件易控制、设备简单且利用率，污水中含盐量低等优点，可大大降低生产成本，提高经济效益，减少污染，非常适合工业化生产。The invention provides a production method of 2-phenyl-2-propanol. 2-Phenyl-2-propanol is an important intermediate in the industrial production of dicumyl peroxide (DCP for short). The method for producing 2-phenyl-2-propanol by reducing cumene hydroperoxide (CHP) with sulfide provided by the invention has the advantages of cheap and easy to obtain reducing agent, low consumption, fast reduction reaction speed, high conversion rate and yield. The advantages of high yield, easy control of reaction conditions, simple equipment and high utilization rate, and low salt content in sewage can greatly reduce production costs, improve economic benefits, and reduce pollution. It is very suitable for industrial production.
Description
The invention belongs to organic chemistry compound probability field.
2-phenyl-2-propyl alcohol is the synthetic dicumyl peroxide important source material of (being called for short DCP), and the synthetic method of existing 2-phenyl-2-propyl alcohol is reduced isopropyl benzene hydroperoxide (being called for short CHP) and realized that its reaction equation is as follows with sodium sulfite aqueous solution:
(1)
It is more expensive that this production method exists reductive agent S-WAT price, large usage quantity (1 molecule S-WAT can only reduce 1 molecule CHP), reductive agent solubleness in water is little, the more high shortcoming of saltiness in reduction reaction late phase reaction speed slow (being that the reaction times is longer) and the waste water.
Day disclosure special permission communique clear 59,110,639, clear 61,246, the 160 method reduction CHP that introduce respectively with catalytic hydrogenation make 2-phenyl-2-propyl alcohol or portion C HP are reverted to alcohol without separating directly manufacturing DCP, though these methods have the yield height, pollute advantages such as little, but must use expensive noble metal catalyst and complicated conversion unit and operational condition.
The present invention introduces a kind of method of making 2-phenyl-2-propyl alcohol with water-soluble sulfide reduction CHP, it is cheap and easy to get to have reductive agent, the reductive agent good water solubility, reduction reaction speed is fast, and (late phase reaction speed is also very fast, residual CHP concentration is low in the reduced liquid), transformation efficiency and recovery rate height, advantage such as reducing process and conversion unit are simple.Compare with the S-WAT reduction method, plant factor obviously improves (promptly use same equipment, can improve its productivity greatly).Because the valency of the sulphur in the sulfide reductive agent that is adopted among the present invention is negative divalence, and the valency of the sulphur in its The product sulfur hydrochlorate after oxidized is positive sexavalence, so a part sulfide can reduce four molecule CHP, therefore saltiness is than S-WAT reduction method reduction more than 70% less and in the waste water for the reductive agent consumption, and its blowdown flow rate can significantly reduce.
Reaction equation with sulfide reduction CHP is as follows:
M in the last reaction formula among the MxS can be H, Li, Na, K, Ca, Mg, NH
4, X can be 1 or 2.As use H
2S, NaHS, NH
4HS etc. make reductive agent, because its oxidation products is acid, are the decomposition that prevents CHP and the dehydration reaction of product alcohol, should in reaction system, add alkali in advance or in reaction process, add continuously alkali with the potential of hydrogen that keeps reaction solution neutral or alkaline.
Relevant key points for operation are as follows:
One, the ingredient proportion of reactant: after single still CHP charging capacity is determined, theoretical consumption according to the definite MxS of reaction equation, the actual amount of sulfide should be no less than theoretical consumption, the actual amount of general MxS should surpass 0～200% (weight percent) of theoretical consumption, and is more suitable above 5～35%.
Two, temperature of reaction, pressure and reaction times: correct adjustable clamp jacket water, jacket steam or utilize reaction heat etc. are controlled at 0～150 ℃ with reduction reaction temperature.Pressure is little to this reaction influence, generally is controlled at normal pressure.Reaction times was generally 0.5～8 hour.
Three, aftertreatment: after reduction reaction is finished, with the reactant standing demix, divide the sub-cloud water, organic phase washes with water 1～3 time, finishes aftertreatment when the pH of washing water is 6～8, and suitable pH scope is 7～7.2.After washing was finished, organic phase was delivered to vacuum and is carried workshop sections such as dense and condensation.
The present invention has an embodiment as follows:
1.33 kilograms of industrial sodium sulfides (content 〉=60%) are dissolved in 10 liters of hot water, then above-mentioned solution is dropped in the stainless steel cauldron of 30 liters of strap clamp covers and stirrer, open the chuck water coolant, stir down with in 15 kilogram 34.65% CHP (all the other are isopropyl benzene) the solution input reactor, react and stop water coolant after 5 minutes, after making reaction carry out 0.5 hour between 30～35 ℃, the logical small amount of steam of chuck slowly rose to 70 ℃ with thing in the still in 0.5 hour, then 70 ± 1 ℃ of following insulation reaction 2 hours, the logical water coolant of chuck makes that material is cooled to about 30 ℃ in the still, stop stirring, behind the standing demix, separate lower floor's water and a small amount of membranoid substance, organic phase is washed 2 times with 10 premium on currency at every turn, and aqueous pH values was 7 after washing was finished for the second time.At last 14 kilograms of water white organic liquids.When CHP feeds intake 2 hours and 3 hours (finishing reaction) in the organic phase content of CHP be respectively 0.71% and 0.385% (iodimetric analysis).2-phenyl in the product-2-propyl alcohol content is 30.23% (high pressure lipuid chromatography (HPLC) analysis).
Claims (1)
- The method of a kind of industrial Synthetic 2-phenyl-2-propyl alcohol is characterized in that wherein: the M among the described water-soluble MxS represents H, Li, Na, K, Ca, Mg or NH with water-soluble sulfide M xS and isopropyl benzene hydroperoxide reaction 4 +, when M is H, Li, Na, K or NH 4 +The time x equal 2, x equals 1 when M is Ca or Mg, the usage quantity of MxS is for pressing Ms and the determined theoretical consumption of isopropyl benzene hydroperoxide reaction equation to 200% of theoretical consumption in the method, temperature of reaction is 0～150 ℃, reaction times is 0.5～8 hour, the back standing demix is finished in reaction, branch sub-cloud water, and the pH value that organic phase is washed with water to water is product during for 16-8.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN93104129A CN1051541C (en) | 1993-03-31 | 1993-03-31 | Prepn. method for 2-phenyl-2-propanol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN93104129A CN1051541C (en) | 1993-03-31 | 1993-03-31 | Prepn. method for 2-phenyl-2-propanol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1093352A CN1093352A (en) | 1994-10-12 |
| CN1051541C true CN1051541C (en) | 2000-04-19 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN93104129A Expired - Fee Related CN1051541C (en) | 1993-03-31 | 1993-03-31 | Prepn. method for 2-phenyl-2-propanol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1051541C (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102911014B (en) * | 2011-08-04 | 2015-04-08 | 中国石油化工股份有限公司 | Di-(2-hydroxyl isopropyl) benzene production method |
| CN102911015B (en) * | 2011-08-04 | 2015-04-29 | 中国石油化工股份有限公司 | Di-(2-hydroxyl isopropyl) benzene production method |
| CN103159592B (en) * | 2011-12-09 | 2015-12-16 | 中国石油化工集团公司 | The production method of two-(2-hydroxyisopropyl) benzene |
| CN103771578B (en) * | 2012-10-19 | 2015-03-25 | 中国石油化工集团公司 | Hydroperoxide reduction production technology |
| CN103772141B (en) * | 2012-10-19 | 2015-08-26 | 中国石油化工集团公司 | Hydroperoxide reduction reaction technique |
| CN104211628A (en) * | 2013-05-30 | 2014-12-17 | 中国石油化工集团公司 | Production equipment for reduction reaction for producing dicumyl peroxide and production method |
| CN104909991B (en) * | 2015-05-07 | 2017-07-21 | 中石化上海工程有限公司 | The method of continuous production cumyl peroxide DCP intermediate products |
| 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 |
| 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 |
| CN110066234A (en) * | 2019-04-01 | 2019-07-30 | 江苏道明化学有限公司 | A kind of DCP reduction reaction process |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5916843A (en) * | 1982-07-20 | 1984-01-28 | Mitsui Toatsu Chem Inc | Continuous preparation of aromatic alcohol |
| JPS59110639A (en) * | 1982-12-17 | 1984-06-26 | Mitsui Toatsu Chem Inc | Production of aromatic alcohol |
| JPS60174737A (en) * | 1984-02-22 | 1985-09-09 | Mitsui Petrochem Ind Ltd | Preparation of aromatic alcohol |
| JPS6429331A (en) * | 1987-07-23 | 1989-01-31 | Nippon Oils & Fats Co Ltd | Production of aromatic alcohol |
| JPH01242539A (en) * | 1988-03-22 | 1989-09-27 | Mitsubishi Petrochem Co Ltd | Method for producing cumyl alcohol |
-
1993
- 1993-03-31 CN CN93104129A patent/CN1051541C/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5916843A (en) * | 1982-07-20 | 1984-01-28 | Mitsui Toatsu Chem Inc | Continuous preparation of aromatic alcohol |
| JPS59110639A (en) * | 1982-12-17 | 1984-06-26 | Mitsui Toatsu Chem Inc | Production of aromatic alcohol |
| JPS60174737A (en) * | 1984-02-22 | 1985-09-09 | Mitsui Petrochem Ind Ltd | Preparation of aromatic alcohol |
| JPS6429331A (en) * | 1987-07-23 | 1989-01-31 | Nippon Oils & Fats Co Ltd | Production of aromatic alcohol |
| JPH01242539A (en) * | 1988-03-22 | 1989-09-27 | Mitsubishi Petrochem Co Ltd | Method for producing cumyl alcohol |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1093352A (en) | 1994-10-12 |
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