CN102603451A - Method for preparing diphenylethane catalyzed by mixed liquid of concentrated sulfuric acid and ion liquid - Google Patents
Method for preparing diphenylethane catalyzed by mixed liquid of concentrated sulfuric acid and ion liquid Download PDFInfo
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- CN102603451A CN102603451A CN2012100458754A CN201210045875A CN102603451A CN 102603451 A CN102603451 A CN 102603451A CN 2012100458754 A CN2012100458754 A CN 2012100458754A CN 201210045875 A CN201210045875 A CN 201210045875A CN 102603451 A CN102603451 A CN 102603451A
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Abstract
The invention provides a method for preparing diphenylethane, and relates to the field of preparing diphenylethane by acid catalysis. The invention aims at solving defects of the traditional acid catalysts and provides a mixed liquid of concentrated sulfuric acid and an ion liquid as an acid catalyst for catalyzing a Friedel-Crafts alkylation reaction of dimethylbenzene (or ethane) and styrene. Compared with the prior art, the method for preparing diphenylethane provided by the invention is mild in reaction, few in side reaction, simple in post processing, recyclable in catalyst, so that the method is low in acid consumption, low in cost, and is more suitable for industrial production.
Description
Technical field
The present invention relates to diarylethane and make the field, particularly relate to the acid catalysis Friedel-Crafts reaction and prepare the diarylethane field.
Background technology
The power capacitor transformer oil is a main raw of producing power capacitor, and its performance quality directly influences the performance of power capacitor.Along with high performance all-film power capacitor progressively replaces film paper recombiner condenser comprehensively, the diarylethane type (comprising PXE and PEPE) that the korenyl type transformer oil that is suitable for impregnated membranes paper recombiner condenser also is suitable for flooding all-film power capacitor comprehensively replaces with benzyl toluene type transformer oil.At present, be about 5.5 ten thousand tons/year as the diarylethane type (comprising PXE and PEPE) of power capacitor transformer oil and the national ultimate production of benzyl toluene (MBT/DBT) type transformer oil.Wherein, under acid catalysis, carrying out Friedel-Crafts reaction through YLENE (or ethylbenzene) and vinylbenzene as the diarylethane of power capacitor transformer oil prepares.
YLENE (or ethylbenzene) and cinnamic reaction are directly to utilize the vitriol oil as acid catalyst traditionally.Advantage with the vitriol oil is that it is cheap and easy to get, and is acid strong.And the shortcoming of sulphuric acid catalysis is corrodibility and oxidisability that it is strong, large usage quantity and can not recycle and produce a large amount of spent acid, difficult treatment, etching apparatus.
Though the environment amenable solid acid catalysis method of exploitation has been used to catalytic synthesis of diaryl ethane (chemical reagent in recent years; 10 (2); 85-86; 1988), but the solid acid catalyst complicated process of preparation, cost an arm and a leg and need frequent regeneration in process of production, this has just hindered its further industrialization.
Increasing research shows and can carry out catalysis Friedel-Crafts reaction (chemical industry and engineering, 27 (3), 1-3,2006) with having the alternative traditional liquid bronsted acid catalyst of Lewis tart ionic liquid.Yet; In the laboratory, be applied to catalyzed reaction though study more chloro-aluminate type ionic liquid with high catalytic activity; But this ionic liquid is very responsive to airborne steam, need under absolute anhydrous condition, use, thereby also be unfavorable for suitability for industrialized production.
Summary of the invention
The object of the invention is exactly that to provide a kind of be the method for catalyzer synthesis of diaryl ethane with the vitriol oil and ion liquid mixed solution for deficiency to above acid catalyst.
The method steps of synthetic power capacitor transformer oil diarylethane provided by the invention is: the vitriol oil and ionic liquid are mixed and made into the acidic ion liquid mixed solution according to a certain percentage; With this acidic ion liquid mixed solution is catalyzer, is raw material with YLENE (or ethylbenzene) and vinylbenzene, carries out alkylated reaction at a certain temperature; Reaction is left standstill after finishing, layering; Divide and remove catalyzer, can get product through underpressure distillation, catalyzer is not treated can directly to be used for catalyzed reaction next time.
Said ionic liquid positively charged ion can be quaternary ammonium salt
The quaternary phosphine salt
Imidazole salt
The pyridine salt
(wherein R1 can be C1～C4 alkyl; R2 can be H or C1～C16 alkyl; R3 can be C1～C4 alkyl; R4 can be C1～C16 alkyl; R5 can be C1～C4 alkyl; R6 can be C1～C4 alkyl; R7 can be C1～C4 alkyl) etc. in one or both and above mixture, negatively charged ion can be Cl
-, HSO
4 -, PF
6 -, BF
4 -Deng in one or both and above mixture, and zwitterion all is not limited to above several types.
Said certain proportion is the vitriol oil: ionic liquid=2: 1～10: 1 (mol ratio), preferred proportion are 3: 1～6: 1.
The mol ratio of the vitriol oil is 1: 1～20: 1 in the vinylbenzene of said adding and the catalyzer, and preferred proportion is 2: 1～10: 1.
Said YLENE (or ethylbenzene) and cinnamic raw material ratio are 3: 1～30: 1, preferably than being 8: 1～20: 1.
Said alkylated reaction temperature is 50～140 ℃, and preferable reaction temperature is 70～100 ℃.
The said alkylated reaction time is 3～15 hours, and the preferred reaction time is 5～8 hours.
Provided by the present invention is catalyzer with the vitriol oil and ionic liquid mixed solution; The method of catalytic synthesis of diaryl ethane and existing concentrated sulfuric acid catalyst, solid acid catalyst and chlorine aluminic acid type ionic-liquid catalyst compared with techniques; Aftertreatment of the present invention is simple; Only need to divide liquid catalyst just can use, reduced cost with the product partitioning cycle; Reaction process of the present invention is gentle, and it is few to generate side reaction product, and the acid consumption is few, pollutes lowly, to steam and air-stable, easy and simple to handle simultaneously, thereby is more suitable in suitability for industrialized production.
Embodiment
Following embodiment can make those skilled in the art more fully understand the present invention, but does not limit the present invention in any way.
Embodiment 1
Add 3.4 gram chlorination tributyl Shi Si Wan Ji Phosphonium in the 250mL round-bottomed flask, stir the vitriol oil that slowly drips 2.4 gram 96-98% down, mix and promptly get acid catalyst.Add 90 gram YLENE in the catalyzer, under 80 ℃ of stirrings, drip 37.2 gram YLENE and the cinnamic mixed solution of 6.2 grams, dripped off in two hours, continue reaction 4 hours.Leave standstill, layering divides sub-cloud ionic-liquid catalyst (recovery), and first normal pressure boils off YLENE, and decompression steams product again, gets 11.6 gram diarylethanes, productive rate 92.8%.
Embodiment 2
Add above recovered acid catalyzer in the 250mL round-bottomed flask, add 90 gram YLENE again, under 80 ℃ of stirrings, drip 37.2 gram YLENE and the cinnamic mixed solution of 9.4 grams, dripped off in two hours, continue reaction 4 hours.Leave standstill, layering divides sub-cloud ionic-liquid catalyst (recovery), and first normal pressure boils off YLENE, and decompression steams product again, gets 16.3 gram diarylethanes, productive rate 85.8%.
Embodiment 3
Add above recovered acid catalyzer in the 250mL round-bottomed flask, add 90 gram YLENE again, under 80 ℃ of stirrings, drip 37.2 gram YLENE and the cinnamic mixed solution of 12.4 grams, dripped off in two hours, continue reaction 3 hours.Leave standstill, layering divides sub-cloud ionic-liquid catalyst (recovery), and first normal pressure boils off YLENE, and decompression steams product again, gets 20.9 gram diarylethanes, productive rate 83.6%.
Embodiment 4
Add above recovered acid catalyzer in the 250mL round-bottomed flask, add 90 gram YLENE again, under 70 ℃ of stirrings, drip 37.2 gram YLENE and the cinnamic mixed solution of 6.2 grams, dripped off in two hours, continue reaction 5 hours.Leave standstill, layering divides sub-cloud ionic-liquid catalyst (recovery), and first normal pressure boils off YLENE, and decompression steams product again, gets 11.1 gram diarylethanes, productive rate 88.8%.
Embodiment 5
Add above recovered acid catalyzer in the 250mL round-bottomed flask, add 90 gram YLENE again, under 100 ℃ of stirrings, drip 37.2 gram YLENE and the cinnamic mixed solution of 6.2 grams, dripped off in two hours, continue reaction 4 hours.Leave standstill, layering divides sub-cloud ionic-liquid catalyst (recovery), and first normal pressure boils off YLENE, and decompression steams product again, gets 10.9 gram diarylethanes, productive rate 87.2%.
Embodiment 6
Add above recovered acid catalyzer in the 250mL round-bottomed flask, add 90 gram ethylbenzene again, under 80 ℃ of stirrings, drip 37.2 gram ethylbenzene and the cinnamic mixed solution of 6.2 grams, dripped off in two hours, continue reaction 4 hours.Leave standstill, layering divides sub-cloud ionic-liquid catalyst (recovery), and first normal pressure boils off ethylbenzene, and decompression steams product again, gets 10.3 gram diarylethanes, productive rate 82.4%.
Embodiment 7
Add 4.4 gram phosphofluoric acid tributyl Shi Si Wan Ji Phosphonium in the 250mL round-bottomed flask, stir the vitriol oil that slowly drips 4.0 gram 96-98% down, mix and promptly get acid catalyst.Add 90 gram YLENE in the catalyzer, under 80 ℃ of stirrings, drip 37.2 gram YLENE and the cinnamic mixed solution of 6.2 grams, dripped off in two hours, continue reaction 4 hours.Leave standstill, layering divides sub-cloud ionic-liquid catalyst (recovery), and first normal pressure boils off YLENE, and decompression steams product again, gets 11.3 gram diarylethanes, productive rate 90.4%.
Embodiment 8
Add 2.9 gram Tetrafluoroboric acid tributyl Shi Si Wan Ji Phosphonium in the 500mL round-bottomed flask, stir the vitriol oil that slowly drips 2.4 gram 96-98% down, mix and promptly get acid catalyst.Add 180 gram YLENE in the catalyzer, under 80 ℃ of stirrings, drip 74.4 gram YLENE and the cinnamic mixed solution of 12.4 grams, dripped off in two hours, continue reaction 6 hours.Leave standstill, layering divides sub-cloud ionic-liquid catalyst (recovery), and first normal pressure boils off YLENE, and decompression steams product again, gets 21.2 gram diarylethanes, productive rate 84.8%.
Embodiment 9
Add 1.6 gram triethylamine vitriol in the 250mL round-bottomed flask, stir the vitriol oil that slowly drips 2.4 gram 96-98% down, mix and promptly get acid catalyst.Add 90 gram YLENE in the catalyzer, under 80 ℃ of stirrings, drip 37.2 gram YLENE and the cinnamic mixed solution of 6.2 grams, dripped off in two hours, continue reaction 4 hours.Leave standstill, layering divides sub-cloud ionic-liquid catalyst (recovery), and first normal pressure boils off YLENE, and decompression steams product again, gets 10.9 gram diarylethanes, productive rate 87.2%.
Embodiment 10
Add 1.3 gram chloridization 1-methyl-3-butyl imidazoles in the 250mL round-bottomed flask, stir the vitriol oil that slowly drips 2.4 gram 96-98% down, mix and promptly get acid catalyst.Add 90 gram YLENE in the catalyzer, under 100 ℃ of stirrings, drip 37.2 gram YLENE and the cinnamic mixed solution of 6.2 grams, dripped off in two hours, continue reaction 4 hours.Leave standstill, layering divides sub-cloud ionic-liquid catalyst (recovery), and first normal pressure boils off YLENE, and decompression steams product again, gets 11.04 gram diarylethanes, productive rate 88.3%.
Embodiment 11
Add 1.3 gram chlorination 1-butyl-pyridinium in the 250mL round-bottomed flask, stir the vitriol oil that slowly drips 2.4 gram 96-98% down, mix and promptly get acid catalyst.Add 90 gram YLENE in the catalyzer, under 100 ℃ of stirrings, drip 37.2 gram YLENE and the cinnamic mixed solution of 6.2 grams, dripped off in two hours, continue reaction 4 hours.Leave standstill, layering divides sub-cloud ionic-liquid catalyst (recovery), and first normal pressure boils off YLENE, and decompression steams product again, gets 11.2 gram diarylethanes, productive rate 89.6%.
Claims (7)
1. method for preparing diarylethane; It is characterized in that with the vitriol oil and ionic liquid mixed solution be an acidic catalyst, is that raw material carries out alkylated reaction with YLENE (or ethylbenzene) and vinylbenzene, and reaction finishes the back branch and removes catalyzer; Can get product through underpressure distillation, catalyzer is reusable.
2. according to the method for claim 1, it is characterized in that said ionic liquid positively charged ion can be quaternary ammonium salt
The quaternary phosphine salt
Imidazole salt
The pyridine salt
(wherein R1 can be C1～C4 alkyl; R2 can be H or C1～C16 alkyl; R3 can be C1～C4 alkyl; R4 can be C1～C16 alkyl; R5 can be C1～C4 alkyl; R6 can be C1～C4 alkyl; R7 can be C1～C4 alkyl) etc. in one or both and above mixture, negatively charged ion can be Cl
-, HSO
4 -, PF
6 -, BF
4 -Deng in one or both and above mixture, and zwitterion all is not limited to above several types.
3. according to the method for claim 1, it is characterized in that said certain proportion is the vitriol oil: ionic liquid=2: 1～10: 1 (mol ratio).
4. according to the method for claim 1, it is characterized in that the mol ratio of the vitriol oil in vinylbenzene and the catalyzer of said adding is 1: 1～20: 1.
5. according to the method for claim 1, it is characterized in that said YLENE (or ethylbenzene) and cinnamic raw material ratio are 3: 1～30: 1.
6. according to the method for claim 1, it is characterized in that said alkylated reaction temperature is 50～140 ℃.
7. according to the method for claim 1, it is characterized in that the said alkylated reaction time is 3～15 hours.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103801402A (en) * | 2012-11-09 | 2014-05-21 | 中化化工科学技术研究总院 | Quaternary phosphonium salt ionic liquid composite catalyst, preparation method and application thereof |
| CN103804118A (en) * | 2012-11-09 | 2014-05-21 | 中化化工科学技术研究总院 | Friedel-Crafts alkylation reaction method |
| CN104926590A (en) * | 2015-05-28 | 2015-09-23 | 江西永通科技股份有限公司 | Synthesis process of p-tart-butyltoluene |
| CN106673936A (en) * | 2016-12-14 | 2017-05-17 | 郑文亚 | Preparation method of bibenzyl |
| CN107297222A (en) * | 2017-06-14 | 2017-10-27 | 东南大学 | A kind of preparation of poly ion liquid solid acid catalyst and its application process |
| CN109395776A (en) * | 2017-08-17 | 2019-03-01 | 华东理工大学 | A kind of alkylated reaction catalyst system and its preparation method and application |
| CN109970501A (en) * | 2019-04-17 | 2019-07-05 | 三峡大学 | A kind of new preparation process of 1,2- diphenylethane |
| CN111617711A (en) * | 2020-06-15 | 2020-09-04 | 辽宁石化职业技术学院 | Microreactor and diarylethane preparation method based on microreactor |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103801402A (en) * | 2012-11-09 | 2014-05-21 | 中化化工科学技术研究总院 | Quaternary phosphonium salt ionic liquid composite catalyst, preparation method and application thereof |
| CN103804118A (en) * | 2012-11-09 | 2014-05-21 | 中化化工科学技术研究总院 | Friedel-Crafts alkylation reaction method |
| CN103801402B (en) * | 2012-11-09 | 2016-03-09 | 中化化工科学技术研究总院 | A kind of quaternary phosphonium salt ionic liquid composite catalyst and its preparation method and application |
| CN103804118B (en) * | 2012-11-09 | 2016-03-09 | 中化化工科学技术研究总院 | A kind of Friedel-Crafts reaction method |
| CN104926590A (en) * | 2015-05-28 | 2015-09-23 | 江西永通科技股份有限公司 | Synthesis process of p-tart-butyltoluene |
| CN106673936A (en) * | 2016-12-14 | 2017-05-17 | 郑文亚 | Preparation method of bibenzyl |
| CN107297222A (en) * | 2017-06-14 | 2017-10-27 | 东南大学 | A kind of preparation of poly ion liquid solid acid catalyst and its application process |
| CN107297222B (en) * | 2017-06-14 | 2020-03-31 | 东南大学 | Preparation and application method of polyion liquid solid acid catalyst |
| CN109395776A (en) * | 2017-08-17 | 2019-03-01 | 华东理工大学 | A kind of alkylated reaction catalyst system and its preparation method and application |
| CN109970501A (en) * | 2019-04-17 | 2019-07-05 | 三峡大学 | A kind of new preparation process of 1,2- diphenylethane |
| CN111617711A (en) * | 2020-06-15 | 2020-09-04 | 辽宁石化职业技术学院 | Microreactor and diarylethane preparation method based on microreactor |
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Application publication date: 20120725 |