CN103374033B - Quaternary phosphonium salt ionic liquid of a kind of organic phosphine functionalization and preparation method thereof - Google Patents
Quaternary phosphonium salt ionic liquid of a kind of organic phosphine functionalization and preparation method thereof Download PDFInfo
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Abstract
The present invention relates to quaternary phosphonium salt ionic liquid of a kind of organic phosphine functionalization and preparation method thereof, while it is characterized in that preparing by triphenylphosphine and bromo alkyl diphenyl phosphine oxide, bromo alkyl phenyl-phosphonic acid ethyl ester or bromo alkyl diethyl phosphonate are 1: 1～1.2 mixing in molar ratio, add organic solvent, be positioned in microwave reaction device, be 350W～500W at microwave power, reaction temperature is 80 DEG C～110 DEG C, reaction time is stirring reaction under the condition of 60min～150min, obtain crude product, remove unreacting material, obtain described triphenylphosphine class ionic liquid. the invention provides a kind of triphenylphosphine class ionic liquid of novel organic phosphine functionalization, adopt the synthetic ionic liquid of heating using microwave greatly to shorten the reaction time simultaneously, improve reaction rate, and raw material availability is higher, no coupling product, the ionic liquid synthesizing is more easily purified, and has efficient, quick, cheap feature.
Description
Technical field
The present invention relates to a kind of triphenylphosphine class ionic liquid and preparation method thereof, specifically three of a kind of organic phosphine functionalizationPhenylphosphine class ionic liquid and preparation method thereof.
Background technology
Ionic liquid is the one salt that (100 DEG C of <) is in a liquid state at low temperatures. Thisly can keep at low temperatures liquid saltDifferent from traditional organic solvent, it has many advantageous properties: steam forces down, non-volatile, nontoxic, nonflammable explosive,Not oxidizable, there is higher heat endurance, mix etc. with multiple organic solvent. Ionic liquid extensive use nearly ten yearsIn the research and development of the aspects such as organic synthesis, electrochemistry, chemical separating and Polymer materialspreparation.
The research of ionic liquid is a relatively new research field. At present, ionic liquid preparation adopts traditional heating moreMethod. Often need tens hours with the synthetic ionic liquid of the method for traditional heating, even when the reaction of tens hoursBetween, also have excessive mol ratio between reactant. The longer reaction time is not only consuming time, easily produces too much by-product simultaneouslyThing brings very large difficulty to separation and purifying, and excessive mol ratio brings very large difficulty also to separation and the purification of productDegree, has also increased cost simultaneously.
The people such as NikolaosTsoureas in 2003 have reported the conventional synthetic method [Nikolaos of similar ionic liquidTsoureas，AndreasA.Danopoulos，etal.(Diphenylphosphino)alkyl-FunctionalizedNucleophilicCarbeneComolexesofPalladium.Organometallics2 003,22,4750-4758]. They adoptReact and obtain a corresponding ionic liquid in by traditional heating method, the reaction time is long, and energy consumption is high. Adopt microwave methodSynthetic ionic liquid Reaction time shorten, now also has report. For example, the patent No. (application number) is 201110219519.5Chinese invention patent the method for the synthetic quaternary ammonium salt ionic liquid of carry out microwave radiation heating is disclosed, shortened the reaction time; SpeciallyThe profit Chinese invention patent that number (application number) is 200910218249.9 disclose under a kind of microwave condition, prepare imidazoles fromThe method of sub-liquid and technique thereof, also shortened the reaction time. But to the triphenylphosphine class ionic liquid of organic phosphine functionalizationSynthesizing of body but do not have report.
Summary of the invention
The quaternary phosphonium salt that first technical problem to be solved by this invention is to provide a kind of novel organic phosphine functionalization fromSub-liquid, it can be applicable to the research of the aspects such as organic synthesis, electrochemistry, chemical separating and Polymer materialspreparation.
Second technical problem to be solved by this invention is to provide a kind of quaternary phosphonium salt ionic liquid of organic phosphine functionalizationPreparation method, adopt heating using microwave synthesize, there is simple, efficient, economic feature, compared with conventional methodCan greatly improve reaction rate and products collection efficiency.
The present invention solves the technical scheme that above-mentioned first technical problem adopts: a kind of quaternary alkylphosphonium salt of organic phosphine functionalizationClass ionic liquid, is characterized in that triphenylphosphine class ionic liquid has following molecular structure:
Wherein, n is 2,3,4,5 or 6; R1For phenyl or ethyoxyl; R2For phenyl or ethyoxyl.
The present invention solves the technical scheme that above-mentioned second technical problem adopt: a kind of quaternary alkylphosphonium salt of organic phosphine functionalizationThe preparation method of class ionic liquid, is characterized in that step is: by triphenylphosphine and bromo alkyl diphenyl phosphine oxide, bromineSubstituted alkyl phenyl-phosphonic acid ethyl ester or bromo alkyl diethyl phosphonate are 1: 1～1.2 mixing in molar ratio,, add organic solvent,Being positioned in microwave reaction device, is 350W～500W at microwave power, and reaction temperature is 80 DEG C～110 DEG C, when reactionBetween be stirring reaction under the condition of 60min～150min, obtain crude product, remove unreacting material, obtain described triphenBase phosphine class ionic liquid.
As preferably, described organic solvent is toluene or dimethylbenzene.
As improvement, described crude product adopts toluene or dimethylbenzene to wash four to five times to remove unreacted raw material, then75～85 DEG C of vacuum drying 2～4h, obtain described triphenylphosphine class ionic liquid.
As preferably, described triphenylphosphine and bromo alkyl diphenyl phosphine oxide, bromo alkyl phenyl-phosphonic acid ethyl ester or bromoThe mol ratio of alkyl phosphonic acid diethylester is 1: 1～1.1.
Preferred again, described microwave power is 400W～480W, and reaction temperature is 90 DEG C～110 DEG C, and the reaction time is80min～120min。
Finally, described microwave power is preferably 450W, and reaction temperature is preferably 100 DEG C, and the reaction time is preferably 100min.
Compared with prior art, the invention has the advantages that: the triphenylphosphine that a kind of novel organic phosphine functionalization is providedClass ionic liquid, because be the compound that contains phosphonate ester or phosphoryl functional group, can be used as fire retardant, and plasticizer is rareSoil ion extractuin agent etc. Phosphonate ester or phosphoryl functional group are bonded on ionic liquid to the functionalized ion liquid of acquisitionWith the characteristic of phosphonate ester and ionic liquid, in field of polymer technology, Rare Earth Separation field and lithium ion battery field have goodGood application prospect; Adopt the synthetic ionic liquid of heating using microwave greatly to shorten the reaction time simultaneously, improved reaction rate,And raw material availability is higher, no coupling product, the ionic liquid synthesizing is more easily purified, and has efficient, quick, cheapFeature, the triphenylphosphine class ionic liquid purity of preparation is high, can be applicable to organic synthesis, electrochemistry, chemical separating andThe research of the aspects such as Polymer materialspreparation.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described in further detail.
Embodiment 1
Get respectively triphenylphosphine (26.2g, 0.1mol), 2-bromoethyl diphenyl phosphine oxide (34.0g, 0.11mol), successivelyAdd in two neck round-bottomed flasks, add 180mL toluene, put into microwave reactor, magnetic agitation, Temperature Setting is100 DEG C, power is 450W, microwave continuous radioreaction 100min, and condensing reflux in course of reaction, after reaction finishesWith toluene wash product four to five times, to remove unreacted raw material, then 80 DEG C of vacuum drying 3h, obtain white solid(2-diphenyl phosphine oxide) ethyltriphenylphosphonium bromide 44.6g, productive rate 78%.
Embodiment 2
Get respectively triphenylphosphine (26.2g, 0.1mol), 2-bromoethyl phenyl phosphinic acid ethyl ester (30.5g, 0.11mol), successivelyAdd in two neck round-bottomed flasks, add 180mL toluene, put into microwave reactor, magnetic agitation, Temperature Setting is100 DEG C, power is 450W, microwave continuous radioreaction 100min, and condensing reflux in course of reaction, after reaction finishesWith toluene wash product four to five times, to remove unreacted raw material, then 80 DEG C of vacuum drying 3h, obtain white solid(2-ethoxyl phenenyl phosphine oxide) ethyltriphenylphosphonium bromide 60.9g, productive rate 76%.
Embodiment 3
Get respectively triphenylphosphine (26.2g, 0.1mol), 2-bromoethyl diphenyl phosphine oxide (34.0g, 0.11mol), successivelyAdd in two neck round-bottomed flasks, add 180mL toluene, put into microwave reactor, magnetic agitation, Temperature Setting is80 DEG C, power is 350W, microwave continuous radioreaction 60min, and condensing reflux in course of reaction, reaction finishes rear useToluene wash product four to five times is to remove unreacted raw material, and then 80 DEG C of vacuum drying 3h, obtain white solid (2-Diphenyl phosphine oxide) ethyltriphenylphosphonium bromide 34.3g, productive rate 60%.
Embodiment 4
Get respectively triphenylphosphine (26.2g, 0.1mol), 2-bromoethyl phenyl phosphinic acid ethyl ester (30.5g, 0.11mol), successivelyAdd in two neck round-bottomed flasks, add 180mL toluene, put into microwave reactor, magnetic agitation, Temperature Setting is90 DEG C, power is 480W, microwave continuous radioreaction 120min, and condensing reflux in course of reaction, reaction finishes rear useToluene wash product four to five times is to remove unreacted raw material, and then 80 DEG C of vacuum drying 3h, obtain white solid (2-Ethoxyl phenenyl phosphine oxide) ethyltriphenylphosphonium bromide 64.1g, productive rate 80%.
Embodiment 5
Get respectively triphenylphosphine (26.2g, 0.1mol), 2-bromoethyl diphenyl phosphine oxide (34.0g, 0.11mol), successivelyAdd in two neck round-bottomed flasks, add 180mL toluene, put into microwave reactor, magnetic agitation, Temperature Setting is110 DEG C, power is 500W, microwave continuous radioreaction 150min, and condensing reflux in course of reaction, after reaction finishesWith toluene wash product four to five times, to remove unreacted raw material, then 80 DEG C of vacuum drying 3h, obtain white solid(2-diphenyl phosphine oxide) ethyltriphenylphosphonium bromide 46.3g, productive rate 81%.
Embodiment 6
Get respectively triphenylphosphine (26.2g, 0.1mol), 3-bromo propyl group diphenyl phosphine oxide (35.5g, 0.11mol), successivelyAdd in two neck round-bottomed flasks, add 180mL toluene, put into microwave reactor, magnetic agitation, Temperature Setting is100 DEG C, power is 450W, microwave continuous radioreaction 100min, and condensing reflux in course of reaction, after reaction finishesWith toluene wash product four to five times, to remove unreacted raw material, then 80 DEG C of vacuum drying 3h, obtain white solid(3-diphenyl phosphine oxide) propyl group triphenyl bromide phosphine 45.0g, productive rate 77%.
Embodiment 7
Get respectively triphenylphosphine (26.2g, 0.1mol), 3-bromo propyl group phenyl phosphinic acid ethyl ester (32.0g, 0.11mol), successivelyAdd in two neck round-bottomed flasks, add 180mL toluene, put into microwave reactor, magnetic agitation, Temperature Setting is100 DEG C, power is 450W, microwave continuous radioreaction 100min, and condensing reflux in course of reaction, after reaction finishesWith toluene wash product four to five times, to remove unreacted raw material, then 80 DEG C of vacuum drying 3h, obtain white solid(3-ethoxyl phenenyl phosphine oxide) propyl group triphenyl bromide phosphine 43.2g, productive rate 78%.
Embodiment 8
Get respectively triphenylphosphine (26.2g, 0.1mol), 3-bromo propyl group diphenyl phosphine oxide (35.5g, 0.11mol), successivelyAdd in two neck round-bottomed flasks, add 180mL toluene, put into microwave reactor, magnetic agitation, Temperature Setting is80 DEG C, power is 350W, microwave continuous radioreaction 60min, and condensing reflux in course of reaction, reaction finishes rear useToluene wash product four to five times is to remove unreacted raw material, and then 80 DEG C of vacuum drying 3h, obtain white solid (3-Diphenyl phosphine oxide) propyl group triphenyl bromide phosphine 34.5g, productive rate 59%.
Embodiment 9
Get respectively triphenylphosphine (26.2g, 0.1mol), 3-bromo propyl group phenyl phosphinic acid ethyl ester (32.0g, 0.11mol), successivelyAdd in two neck round-bottomed flasks, add 180mL toluene, put into microwave reactor, magnetic agitation, Temperature Setting is90 DEG C, power is 480W, microwave continuous radioreaction 120min, and condensing reflux in course of reaction, reaction finishes rear useToluene wash product four to five times is to remove unreacted raw material, and then 80 DEG C of vacuum drying 3h, obtain white solid (3-Ethoxyl phenenyl phosphine oxide) propyl group triphenyl bromide phosphine 44.9g, productive rate 81%.
Embodiment 10
Get respectively triphenylphosphine (26.2g, 0.1mol), 3-bromo propyl group diphenyl phosphine oxide (35.5g, 0.11mol), successivelyAdd in two neck round-bottomed flasks, add 180mL toluene, put into microwave reactor, magnetic agitation, Temperature Setting is110 DEG C, power is 500W, microwave continuous radioreaction 150min, and condensing reflux in course of reaction, after reaction finishesWith toluene wash product four to five times, to remove unreacted raw material, then 80 DEG C of vacuum drying 3h, obtain white solid(3-diphenyl phosphine oxide) propyl group triphenyl bromide phosphine 48.0g, productive rate 82%.
Embodiment 11
Get respectively triphenylphosphine (26.2g, 0.1mol), 5-bromo amyl group diphenyl phosphine oxide (38.6g, 0.11mol), successivelyAdd in two neck round-bottomed flasks, add 180mL toluene, put into microwave reactor, magnetic agitation, Temperature Setting is100 DEG C, power is 450W, microwave continuous radioreaction 100min, and condensing reflux in course of reaction, after reaction finishesWith toluene wash product four to five times, to remove unreacted raw material, then 80 DEG C of vacuum drying 3h, obtain white solid(5-diphenyl phosphine oxide) amyl group triphenyl bromide phosphine 48.4g, productive rate 79%.
Embodiment 12
Get respectively triphenylphosphine (26.2g, 0.1mol), 5-bromo amyl group phenyl phosphinic acid ethyl ester (35.1g, 0.11mol), successivelyAdd in two neck round-bottomed flasks, add 180mL toluene, put into microwave reactor, magnetic agitation, Temperature Setting is100 DEG C, power is 450W, microwave continuous radioreaction 100min, and condensing reflux in course of reaction, after reaction finishesWith toluene wash product four to five times, to remove unreacted raw material, then 80 DEG C of vacuum drying 3h, obtain white solid(5-ethoxyl phenenyl phosphine oxide) amyl group triphenyl bromide phosphine 45.3g, productive rate 78%.
Embodiment 13
Get respectively triphenylphosphine (26.2g, 0.1mol), 5-bromo amyl group diphenyl phosphine oxide (38.6g, 0.11mol), successivelyAdd in two neck round-bottomed flasks, add 180mL toluene, put into microwave reactor, magnetic agitation, Temperature Setting is80 DEG C, power is 350W, microwave continuous radioreaction 60min, and condensing reflux in course of reaction, reaction finishes rear useToluene wash product four to five times is to remove unreacted raw material, and then 80 DEG C of vacuum drying 3h, obtain white solid (5-Diphenyl phosphine oxide) amyl group triphenyl bromide phosphine 36.1g, productive rate 59%.
Embodiment 14
Get respectively triphenylphosphine (26.2g, 0.1mol), 5-bromo amyl group phenyl phosphinic acid ethyl ester (35.1g, 0.11mol), complies withInferior adding in two neck round-bottomed flasks, adds 180mL toluene, puts into microwave reactor, magnetic agitation, Temperature SettingBe 90 DEG C, power is 480W, microwave continuous radioreaction 120min, and condensing reflux in course of reaction, after reaction finishesWith toluene wash product four to five times, to remove unreacted raw material, then 80 DEG C of vacuum drying 3h, obtain white solid(5-ethoxyl phenenyl phosphine oxide) amyl group triphenyl bromide phosphine 40.6g, productive rate 70%.
Embodiment 15
Get respectively triphenylphosphine (26.2g, 0.1mol), 5-bromo amyl group diphenyl phosphine oxide (38.6g, 0.11mol), successivelyAdd in two neck round-bottomed flasks, add 180mL toluene, put into microwave reactor, magnetic agitation, Temperature Setting is110 DEG C, power is 500W, microwave continuous radioreaction 150min, and condensing reflux in course of reaction, after reaction finishesWith toluene wash product four to five times, to remove unreacted raw material, then 80 DEG C of vacuum drying 3h, obtain white solid(5-diphenyl phosphine oxide) amyl group triphenyl bromide phosphine 46.5g, productive rate 76%.
Embodiment 16
Get respectively triphenylphosphine (26.2g, 0.1mol), 2-bromoethyl diethyl phosphonate (27.0g, 0.11mol), successivelyAdd in two neck round-bottomed flasks, add 180mL toluene, put into microwave reactor, magnetic agitation, Temperature Setting is100 DEG C, power is 450W, microwave continuous radioreaction 100min, and condensing reflux in course of reaction, after reaction finishesWith toluene wash product four to five times, to remove unreacted raw material, then 80 DEG C of vacuum drying 3h, obtain colourless thicknessLiquid (2-diethyl phosphonate) ethyltriphenylphosphonium bromide 35.5g, productive rate 70%.
Embodiment 17
Get respectively triphenylphosphine (26.2g, 0.1mol), 2-bromoethyl diethyl phosphonate (27.0g, 0.11mol), successivelyAdd in two neck round-bottomed flasks, add 180mL toluene, put into microwave reactor, magnetic agitation, Temperature Setting is80 DEG C, power is 350W, microwave continuous radioreaction 60min, and condensing reflux in course of reaction, reaction finishes rear useToluene wash product four to five times is to remove unreacted raw material, and then 80 DEG C of vacuum drying 3h, obtain colourless viscous fluidBody (2-diethyl phosphonate) ethyltriphenylphosphonium bromide 29.5g, productive rate 58%.
Embodiment 18
Get respectively triphenylphosphine (26.2g, 0.1mol), 3-bromo propyl phosphonous acid diethylester (28.5g, 0.11mol), adds successivelyEnter in two neck round-bottomed flasks, add 180mL toluene, put into microwave reactor, magnetic agitation, Temperature Setting is 90DEG C, power is 480W, microwave continuous radioreaction 120min, and condensing reflux in course of reaction, uses first after reaction finishesBenzene washed product four to five times is to remove unreacted raw material, and then 80 DEG C of vacuum drying 3h, obtain colourless viscous liquid(3-diethyl phosphonate) propyl group triphenyl bromide phosphine 37.0g, productive rate 71%.
Embodiment 19
Get respectively triphenylphosphine (26.2g, 0.1mol), 3-bromo propyl phosphonous acid diethylester (28.5g, 0.11mol), adds successivelyEnter in two neck round-bottomed flasks, add 180mL toluene, put into microwave reactor, magnetic agitation, Temperature Setting is 110DEG C, power is 500W, microwave continuous radioreaction 150min, and condensing reflux in course of reaction, uses first after reaction finishesBenzene washed product four to five times is to remove unreacted raw material, and then 80 DEG C of vacuum drying 3h, obtain colourless viscous liquid(3-diethyl phosphonate) propyl group triphenyl bromide phosphine 42.7g, productive rate 82%.
Embodiment 20
Get respectively triphenylphosphine (26.2g, 0.1mol), 5-bromo amyl group diethyl phosphonate (31.6g, 0.11mol), adds successivelyEnter in two neck round-bottomed flasks, add 180mL toluene, put into microwave reactor, magnetic agitation, Temperature Setting is 80DEG C, power is 350W, microwave continuous radioreaction 60min, and condensing reflux in course of reaction, uses first after reaction finishesBenzene washed product four to five times is to remove unreacted raw material, and then 80 DEG C of vacuum drying 3h, obtain white solid (5-Diethyl phosphonate) amyl group triphenyl bromide phosphine 30.7g, productive rate 56%.
Embodiment 21
Get respectively triphenylphosphine (26.2g, 0.1mol), 5-bromo amyl group diethyl phosphonate (31.6g, 0.11mol), adds successivelyEnter in two neck round-bottomed flasks, add 180mL toluene, put into microwave reactor, magnetic agitation, Temperature Setting is 90 DEG C,Power is 480W, microwave continuous radioreaction 120min, and condensing reflux in course of reaction, reaction finishes to wash with toluene afterwardsWash product four to five times to remove unreacted raw material, then 80 DEG C of vacuum drying 3h, obtain white solid (5-phosphonic acidsDiethylester) amyl group triphenyl bromide phosphine 37.4g, productive rate 68%.
Embodiment 22
Get respectively triphenylphosphine (26.2g, 0.1mol), 5-bromo amyl group diethyl phosphonate (31.6g, 0.11mol), adds successivelyEnter in two neck round-bottomed flasks, add 180mL dimethylbenzene, put into microwave reactor, magnetic agitation, Temperature Setting is110 DEG C, power is 500W, microwave continuous radioreaction 150min, and condensing reflux in course of reaction, after reaction finishesBy dimethylbenzene washed product four to five times, to remove unreacted raw material, then 80 DEG C of vacuum drying 3h, obtain white solidBody (5-diethyl phosphonate) amyl group triphenyl bromide phosphine 43.9g, productive rate 80%.
Claims (6)
1. a preparation method for the quaternary phosphonium salt ionic liquid of organic phosphine functionalization, is characterized in that step is: by threePhenylphosphine mixes for 1:1～1.2 in molar ratio with bromo alkyl diphenyl phosphine oxide or bromo alkyl phenyl-phosphonic acid ethyl ester,Adding organic solvent, be positioned in microwave reaction device, is 350W～500W at microwave power, and reaction temperature is80 DEG C～110 DEG C, stirring reaction under the condition that the reaction time is 60min～150min, obtains crude product, removes unreactedRaw material, obtains triphenylphosphine class ionic liquid, and the triphenylphosphine class ionic liquid making has following molecular structure:
Wherein, n is 3,4,5 or 6; R1、R2Select phenyl or ethyoxyl, and R1、R2At least one is phenyl.
2. preparation method according to claim 1, is characterized in that described organic solvent is toluene or dimethylbenzene.
3. preparation method according to claim 1, is characterized in that described crude product adopts toluene or dimethylbenzene to washWash four to five times to remove unreacted raw material, then 75～85 DEG C of vacuum drying 2～4h, obtain described triphenylphosphine class fromSub-liquid.
4. preparation method according to claim 1, is characterized in that described triphenylphosphine and bromo alkyl diphenylThe mol ratio of phosphine oxide or bromo alkyl phenyl-phosphonic acid ethyl ester is 1:1～1.1.
5. preparation method according to claim 1, is characterized in that described microwave power is 400W～480W, anti-Answering temperature is 90 DEG C～110 DEG C, and the reaction time is 80min～120min.
6. preparation method according to claim 5, is characterized in that described microwave power is 450W, reaction temperatureBe 100 DEG C, the reaction time is 100min.
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| CN104087750B (en) * | 2014-07-14 | 2016-12-07 | 厦门稀土材料研究所 | A kind of extraction separating method of rare earth |
| CN104926869B (en) * | 2015-06-30 | 2018-04-27 | 宁波大学 | A kind of bidentate difunctionalization imidazole type ion liquid and preparation method thereof |
| CN105837627B (en) * | 2015-06-30 | 2018-06-29 | 宁波大学 | A kind of difunctionalization quaternary ammonium salt ionic liquid and preparation method thereof |
| CN105837628B (en) * | 2015-06-30 | 2018-05-29 | 宁波大学 | A kind of difunctionalization quaternary phosphonium ionic liquid and preparation method thereof |
| CN105017320B (en) * | 2015-07-02 | 2017-03-01 | 武汉理工大学 | The method preparing the double salt of two fluoro ethyl salt/1,2 vinyls under condition of no solvent |
| CN109134539A (en) * | 2018-11-01 | 2019-01-04 | 江西肯特化学有限公司 | A kind of method and apparatus preparing tri-phenyl-ethyl phosphonium bromide |
| CN114058020A (en) * | 2021-11-20 | 2022-02-18 | 江苏康爱特环境工程集团有限公司 | Preparation method and application of quaternary phosphonium salt |
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| CN101037449A (en) * | 2007-04-09 | 2007-09-19 | 广州巨元生化有限公司 | New quaternary phosphonium salt and synthesizing method applied for carotenoids |
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| CN101037449A (en) * | 2007-04-09 | 2007-09-19 | 广州巨元生化有限公司 | New quaternary phosphonium salt and synthesizing method applied for carotenoids |
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