CN102558230A - Quaternary phosphor salt acidic ionic liquid and application thereof in synthesizing benzyltoluene - Google Patents
Quaternary phosphor salt acidic ionic liquid and application thereof in synthesizing benzyltoluene Download PDFInfo
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- CN102558230A CN102558230A CN2010105989267A CN201010598926A CN102558230A CN 102558230 A CN102558230 A CN 102558230A CN 2010105989267 A CN2010105989267 A CN 2010105989267A CN 201010598926 A CN201010598926 A CN 201010598926A CN 102558230 A CN102558230 A CN 102558230A
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- ionic liquid
- liquid
- acidic ion
- lewis acidic
- quaternary
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- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical compound C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 239000011831 acidic ionic liquid Substances 0.000 title abstract description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title abstract 3
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- 239000007788 liquid Substances 0.000 claims abstract description 38
- -1 zinc halide Chemical class 0.000 claims abstract description 10
- 239000011701 zinc Substances 0.000 claims abstract description 9
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 239000003990 capacitor Substances 0.000 claims abstract description 6
- 230000002378 acidificating effect Effects 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 19
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims description 3
- 239000002608 ionic liquid Substances 0.000 abstract description 25
- 239000002994 raw material Substances 0.000 abstract description 3
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 150000002500 ions Chemical class 0.000 description 22
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 19
- 239000000460 chlorine Substances 0.000 description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 8
- 230000009466 transformation Effects 0.000 description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000010792 warming Methods 0.000 description 7
- 239000011973 solid acid Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000005660 chlorination reaction Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 235000005074 zinc chloride Nutrition 0.000 description 4
- 239000011592 zinc chloride Substances 0.000 description 4
- 238000007171 acid catalysis Methods 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical class Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 3
- 239000007848 Bronsted acid Substances 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a quaternary phosphor salt acidic ionic liquid and application thereof in synthesizing benzyltoluene, belonging to the field of preparation and application of ionic liquids. The general formula of the vapor-insensitive quaternary phosphor salt Lewis acidic ionic liquid is Bu3P<+>RB<->/ZnX2, wherein R is C12-16 aliphatic alkyl group, B- is one of Cl<->, Br<-> or PF6<->, and X is Cl<-> or Br<->. The preparation method comprises the following steps: adding a certain proportion of zinc halide into the Bu3P<+>RB-, and reacting under certain temperature to generate a transparent liquid. The ionic liquid can be used for catalytically preparing power capacitor insulating oil benzyltoluene. Compared with the prior art, the invention has the advantages of accessible raw materials, simple after-treatment and environment friendliness, can be recycled, and is insensitive to vapor.
Description
Technical field
The present invention relates to ionic liquid preparation and Application Areas, further say so about a kind of the insensitive quaternary phosphine salt of steam Lewis acidic ion liquid and method for making and the application in the synthetic power capacitor transformer oil benzyl toluene of catalysis.
Background technology
Under acid catalysis, carrying out Friedel-Crafts reaction through toluene and benzyl chlorine as the benzyl toluene of power capacitor transformer oil prepares.Shortcoming with sulphuric acid catalysis is large usage quantity and can not recycles and produce a large amount of spent acid, difficult treatment, etching apparatus.In addition; Though the environment amenable solid acid catalysis method of exploitation has been used to the production of benzyl toluene type transformer oil in recent years; But the solid acid catalyst complicated process of preparation, cost an arm and a leg and need frequent regeneration in process of production; Make the production cost of benzyl toluene can not be in any more, limited promoting the use of of benzyl toluene.Research shows and can carry out acid catalyzed reaction (petrochemical complex, 33 (4), 297-302,2004 with having alternative traditional liquid bronsted acid catalyst and the solid acid catalyst of Lewis tart ionic liquid; Sanming College's journal, 26 (2), 19-193,2009).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, otherwise catalytic activity and selectivity have obvious decline, therefore seek the insensitive high stability acidic ion liquid of steam very necessary.
We know that ionic liquid is made up of zwitterion; In positively charged ion to researchs such as quaternary ammonium salt, pyroles, imidazoles with report that more Er quaternary phosphine positively charged ion also is one type of important ionic liquid positively charged ion; For the building-up reactions of quaternary alkylphosphonium salt study also comparatively ripe (CN200310100174); Particularly (14,16) Phosphonium are as sterilant commercialization, but utilize it less as the research of functionalized acidic ionic liquid, and the catalyzer that the conduct of especially preparing high stability by it prepares power capacitor transformer oil benzyl toluene does not appear in the newspapers for halogenation tributyl 12.
Summary of the invention
The object of the invention is exactly to traditional liquid acid, solid acid and the ion liquid deficiency of chlorine aluminic acid type, provides a kind of and has a quaternary phosphine salt Lewis acidic ion liquid that high stability and raw material are easy to get to steam is insensitive.And this quaternary phosphine salt Lewis acidic ion liquid is applied to catalytic preparation power capacitor transformer oil benzyl toluene.
Technical scheme of the present invention is following:
It is a kind of to the insensitive quaternary phosphine salt of steam Lewis acidic ion liquid that the present invention provides, and its general formula is: Bu
3P
+RB
-/ ZnX
2, wherein R is the aliphatic alkyl of C12~16, B
-Be Cl
-, Br
-, PF
6 -In a kind of, X is Cl
-Or Br
-
The invention provides the method for making of above-mentioned Lewis acidic ion liquid, step is: quaternary alkylphosphonium salt Bu
3P
+RB
-The a certain proportion of zinc halide of middle adding is reacted into transparent liquid at a certain temperature and just gets the Lewis acidic ion liquid.
R in the said quaternary alkylphosphonium salt is the aliphatic alkyl of C12~16, and the ratio of said adding zinc halide is X=0.6~0.8 (an X=zinc halide mole number/zinc halide mole number+quaternary alkylphosphonium salt mole numbers), and said temperature of reaction is 100~150 ℃.Reaction times is 1~5 hour.
Above-mentioned Lewis acidic ion liquid is applied to the catalytic preparation benzyl toluene, and method is: toluene is mixed with benzyl chlorine according to a certain percentage, add a certain amount of above-mentioned quaternary phosphine salt Lewis acidic ion liquid, back flow reaction.
Said toluene and benzyl chlorine blending ratio are 2: 1~10: 1.Reaction times is 2~8 hours.
With existing liquid bronsted acid catalyst, solid acid catalyst and chloro-aluminate type ionic-liquid catalyst compared with techniques, aftertreatment of the present invention is simple, only needs to divide liquid catalyst just can to separate with product and recycle, and has reduced cost.The present invention is environmentally friendly, and is to steam and air-stable, easy and simple to handle simultaneously, is fit to suitability for industrialized production.In addition, utilize commercial quaternary alkylphosphonium salt to prepare acidic ion liquid and have more the advantage that raw material is easy to get.
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 40.7 gram (0.1mol) chlorination tributyls, 14 alkane base Phosphonium in the 250mL round-bottomed flask, add 40.8 gram (0.3mol) zinc chloride under 40 ℃ of stirrings in batches, be warming up to 120 ℃ of reactions 2 hours, become transparent liquid to be quaternary phosphine salt Lewis acidic ion liquid.Other gets the 250mL round-bottomed bottle, adds 64.4 gram (0.7mol) toluene and 8.9 gram (0.07mol) benzyl chlorine, adds the above-mentioned Bu of 8.2 grams again
3P
+(CH
2)
13CH
3Cl
-/ ZnCl
2Ionic liquid, back flow reaction 2 hours leaves standstill, separatory, the transformation efficiency that upper strata GC analyzes benzyl chlorine is 100%, productive rate is 95%.The ionic liquid of lower floor can be recycled.
Embodiment 2
Get the 250mL round-bottomed bottle, add 64.4 gram (0.7mol) toluene and 8.9 gram (0.07mol) benzyl chlorine, add the Bu that separatory reclaims among the embodiment 1 again
3P
+(CH
2)
13CH
3Cl
-/ ZnCl
2Ionic liquid, back flow reaction 2 hours leaves standstill, separatory, the transformation efficiency that upper strata GC analyzes benzyl chlorine is 100%, productive rate is 96%.The ionic liquid of lower floor can be recycled.
Embodiment 3
Add 42.3 gram (0.1mol) bromination tributyls, 12 alkane base Phosphonium in the 250mL round-bottomed flask, add 27.2 gram (0.2mol) zinc chloride under 40 ℃ of stirrings in batches, be warming up to 100 ℃ of reactions 3 hours, become transparent liquid to be quaternary phosphine salt Lewis acidic ion liquid.Other gets the 250mL round-bottomed bottle, adds 64.4 gram (0.7mol) toluene and 8.9 gram (0.07mol) benzyl chlorine, adds the above-mentioned Bu of 8.6 grams again
3P
+(CH
2)
11CH
3Br
-/ ZnCl
2Ionic liquid, back flow reaction 4 hours leaves standstill, separatory, the transformation efficiency that upper strata GC analyzes benzyl chlorine is 100%, productive rate is 95%.The ionic liquid of lower floor can be recycled.
Embodiment 4
Add 37.9 gram (0.1mol) chlorination tributyls, 12 alkane base Phosphonium in the 250mL round-bottomed flask, add 13.6 gram (0.3mol) zinc chloride under 40 ℃ of stirrings in batches, be warming up to 120 ℃ of reactions 4 hours, become transparent liquid to be quaternary phosphine salt Lewis acidic ion liquid.Other gets the 250mL round-bottomed bottle, adds 19.3 gram (0.21mol) toluene and 8.9 gram (0.07mol) benzyl chlorine, adds the above-mentioned Bu of 6.8 grams again
3P
+(CH
2)
11CH
3Cl
-/ ZnCl
2Ionic liquid, back flow reaction 4 hours leaves standstill, separatory, the transformation efficiency that upper strata GC analyzes benzyl chlorine is 100%, productive rate is 94%.The ionic liquid of lower floor can be recycled.
Embodiment 5
Add 51.7 gram (0.1mol) phosphofluoric acid tributyls, 14 alkane base Phosphonium in the 250mL round-bottomed flask, add 54.4 gram (0.4mol) zinc chloride under 40 ℃ of stirrings in batches, be warming up to 150 ℃ of reactions 2 hours, become transparent liquid to be quaternary phosphine salt Lewis acidic ion liquid.Other gets the 250mL round-bottomed bottle, adds 41.1 gram (0.45mol) toluene and 8.9 gram (0.07mol) benzyl chlorine, adds the above-mentioned Bu of 10.6 grams again
3P
+(CH
2)
13CH
3PF
6 -/ ZnCl
2Ionic liquid, back flow reaction 4 hours leaves standstill, separatory, the transformation efficiency that upper strata GC analyzes benzyl chlorine is 100%, productive rate is 97%.The ionic liquid of lower floor can be recycled.
Embodiment 6
Add 40.7 gram (0.1mol) chlorination tributyls, 14 alkane base Phosphonium in the 250mL round-bottomed flask, add 67.5 gram (0.3mol) zinc bromides under 40 ℃ of stirrings in batches, be warming up to 120 ℃ of reactions 5 hours, become transparent liquid to be quaternary phosphine salt Lewis acidic ion liquid.Other gets the 250mL round-bottomed bottle, adds 64.4 gram (0.7mol) toluene and 44.5 gram (0.35mol) benzyl chlorine, adds the above-mentioned Bu of 10.9 grams again
3P
+(CH
2)
13CH
3Cl
-/ ZnBr
2Ionic liquid, back flow reaction 8 hours leaves standstill, separatory, the transformation efficiency that upper strata GC analyzes benzyl chlorine is 100%, productive rate is 94%.The ionic liquid of lower floor can be recycled.
Embodiment 7
Add 43.5 gram (0.1mol) chlorination tributyls, 16 alkane base Phosphonium in the 250mL round-bottomed flask, add 67.5 gram (0.3mol) zinc bromides under 40 ℃ of stirrings in batches, be warming up to 120 ℃ of reactions 3 hours, become transparent liquid to be quaternary phosphine salt Lewis acidic ion liquid.Other gets the 250mL round-bottomed bottle, adds 64.4 gram (0.7mol) toluene and 8.9 gram (0.07mol) benzyl chlorine, adds the above-mentioned Bu of 12.5 grams again
3P
+(CH
2)
15CH
3Cl
-/ ZnBr
2Ionic liquid, back flow reaction 6 hours leaves standstill, separatory, the transformation efficiency that upper strata GC analyzes benzyl chlorine is 100%, productive rate is 95%.The ionic liquid of lower floor can be recycled.
Embodiment 8
Add 47.9 gram (0.1mol) bromination tributyls, 16 alkane base Phosphonium in the 250mL round-bottomed flask, add 67.5 gram (0.3mol) zinc bromides under 40 ℃ of stirrings in batches, be warming up to 100 ℃ of reactions 3 hours, become transparent liquid to be quaternary phosphine salt Lewis acidic ion liquid.Other gets the 250mL round-bottomed bottle, adds 64.4 gram (0.7mol) toluene and 8.9 gram (0.07mol) benzyl chlorine, adds the above-mentioned Bu of 11.3 grams again
3P
+(CH
2)
15CH
3Br
-/ ZnBr
2Ionic liquid, back flow reaction 5 hours leaves standstill, separatory, the transformation efficiency that upper strata GC analyzes benzyl chlorine is 100%, productive rate is 96%.The ionic liquid of lower floor can be recycled.
Claims (5)
1. one kind to the insensitive quaternary phosphine salt of steam Lewis acidic ion liquid, and its general formula is: Bu
3P
+RB
-/ ZnX
2
2. according to the Lewis acidic ion liquid of claim 1, it is characterized in that R is the aliphatic alkyl of C12~16, B
-Be Cl
-, Br
-, PF
6 -In a kind of, X is Cl
-Or Br
-
3. the preparation method of the described Lewis acidic ion liquid of claim 1 is: quaternary alkylphosphonium salt Bu
3P
+RX
-The a certain proportion of zinc halide of middle adding is reacted into transparent liquid at a certain temperature and just gets the Lewis acidic ion liquid.
4. according to the method for making of claim 3; It is characterized in that said quaternary alkylphosphonium salt R is the aliphatic alkyl of C12~16; The ratio of said adding zinc halide is X=0.6~0.8 (an X=zinc halide mole number/zinc halide mole number+quaternary alkylphosphonium salt mole numbers); Said temperature of reaction is 60~150 ℃, and the reaction times is 1~5 hour.
5. according to the described Lewis acidic ion liquid of claim 1, it is characterized in that can be used as the catalyzer of preparation power capacitor transformer oil benzyl toluene.
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Cited By (8)
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CN103319297A (en) * | 2013-06-26 | 2013-09-25 | 四川东材科技集团股份有限公司 | Method for preparing phenyl ethylbenzene ethane capacitor insulating oil through catalysis of acidic ionic liquid |
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 |
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 |
CN103805307A (en) * | 2012-11-09 | 2014-05-21 | 中化化工科学技术研究总院 | Preparation method for capacitor insulating oil |
CN103804111A (en) * | 2012-11-09 | 2014-05-21 | 中化化工科学技术研究总院 | Preparation method of heat conduction oil |
CN103833509A (en) * | 2012-11-23 | 2014-06-04 | 中国石油天然气股份有限公司 | Method for synthesizing benzyltoluene under catalysis of solid acid catalyst |
CN103833508A (en) * | 2012-11-23 | 2014-06-04 | 中国石油天然气股份有限公司 | Method for catalytically synthesizing dibenzyltoluene by using solid acid catalyst |
CN105017144A (en) * | 2014-04-25 | 2015-11-04 | 江苏圣奥化学科技有限公司 | Rubber aging inhibitor RD and preparation method for same |
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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 |
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 |
CN103805307A (en) * | 2012-11-09 | 2014-05-21 | 中化化工科学技术研究总院 | Preparation method for capacitor insulating oil |
CN103804111A (en) * | 2012-11-09 | 2014-05-21 | 中化化工科学技术研究总院 | Preparation method of heat conduction oil |
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 |
CN103804111B (en) * | 2012-11-09 | 2015-07-15 | 中化化工科学技术研究总院 | Preparation method of heat conduction oil |
CN103833508A (en) * | 2012-11-23 | 2014-06-04 | 中国石油天然气股份有限公司 | Method for catalytically synthesizing dibenzyltoluene by using solid acid catalyst |
CN103833509A (en) * | 2012-11-23 | 2014-06-04 | 中国石油天然气股份有限公司 | Method for synthesizing benzyltoluene under catalysis of solid acid catalyst |
CN103319297A (en) * | 2013-06-26 | 2013-09-25 | 四川东材科技集团股份有限公司 | Method for preparing phenyl ethylbenzene ethane capacitor insulating oil through catalysis of acidic ionic liquid |
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CN105017144B (en) * | 2014-04-25 | 2019-05-28 | 圣奥化学科技有限公司 | A kind of rubber antiager RD and preparation method thereof |
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