CN106279227A - The preparation method of lithium triethylborohydride tetrahydrofuran solution - Google Patents
The preparation method of lithium triethylborohydride tetrahydrofuran solution Download PDFInfo
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- CN106279227A CN106279227A CN201610583711.5A CN201610583711A CN106279227A CN 106279227 A CN106279227 A CN 106279227A CN 201610583711 A CN201610583711 A CN 201610583711A CN 106279227 A CN106279227 A CN 106279227A
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- tetrahydrofuran solution
- ether
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
Abstract
The preparation method of a kind of lithium triethylborohydride tetrahydrofuran solution, its step includes bromoethane diethyl ether solution preparatory phase, boron triethyl tetrahydrofuran solution preparatory phase, lithium triethylborohydride tetrahydrofuran solution preparatory phase.It provides the benefit that: preparation process is stable, it is ensured that the lithium triethylborohydride tetrahydrofuran solution quality of preparation.
Description
Technical field
The present invention relates to field of inorganic chemical engineering, the preparation of a kind of lithium triethylborohydride.
Background technology
Lithium triethylborohydride is a kind of extremely strong nucleophilic reduction agent, according to streitwiesear ' s nucleophilic power data meter
Calculate, its nucleophilic power is 10,000 times of its parent lithium borohydride, is 40 times of lithium aluminium hydride reduction, in organic synthesis it can reduce aldehyde,
Ketone, ketenes, cyclic ketones and dicyclo ketone, the carboxylic acid derivates such as anhydride, cyclic anhydride and acyl chlorides that can reduce, can reduce primary amide, teritary amide, fat
Fat race nitro compound, ester, lactone, sulfur-containing compound, sulfonic acid, halogenated aryl hydrocarbon, epoxide, it is gone back in region or three-dimensional selection
Show excellent characteristic in former, be described as " super hydride ".
Lithium triethylborohydride, Lithium triethylborohydride, CAS No:22560-16-3 molecular formula Li
(C2H5)3BH, molecular weight: 105.94, boiling point is 92 DEG C, and the chemism of this product is the highest, and therefore, the business form of this product is molten
Solution concentration in oxolane is the solution of 1mol/L, and the density of this product is 0.892g/ml, and flash-point is-17 DEG C, and it is at tetrahydrochysene
In the nitrogen of tetrahydrofuran solution highly stable.
If but be positioned in air or dampness, the rapid moisture absorption is decomposed, and the intermediate product in its preparation process
This problem is there is also with preparing feedstock portions.
Summary of the invention
The invention aims to solve the problems referred to above, devise a kind of lithium triethylborohydride tetrahydrofuran solution
Preparation method.Specific design scheme is:
The preparation method of a kind of lithium triethylborohydride tetrahydrofuran solution, its step includes prepared by bromoethane diethyl ether solution
Stage, boron triethyl tetrahydrofuran solution preparatory phase, lithium triethylborohydride tetrahydrofuran solution preparatory phase,
Described bromoethane diethyl ether solution preparatory phase is physical reactions, it is thus achieved that bromoethane diethyl ether solution；
Reaction equation prepared by described boron triethyl tetrahydrofuran solution is:
BF3.Et2O+3Mg+3C2H5Br→(C2H5)3B+3MgBrF↓
Described boron triethyl tetrahydrofuran solution preparatory phase is prepared raw material and is included ether, boron trifluoride ether solution, gold
Belong to magnesium powder, bromoethane diethyl ether solution and oxolane, prepare boron triethyl tetrahydrofuran solution；
Reaction equation prepared by described lithium triethylborohydride tetrahydrofuran solution is:
Described lithium triethylborohydride tetrahydrofuran solution preparatory phase prepare raw material include oxolane, lithium hydride,
Boron triethyl tetrahydrofuran solution, nitrogen.
In described boron triethyl tetrahydrofuran solution preparatory phase, ether is mixed with metal magnesium powder, is subsequently adding
Boron trifluoride ether solution, then it is added dropwise to bromoethane diethyl ether solution, wherein:
The volume parts of described ether and the boron trifluoride ether solution of addition is than for ether: boron trifluoride ether solution=
1600∶148.8；
The mass fraction ratio of described metal magnesium powder and boron trifluoride ether solution is for metal magnesium powder: boron trifluoride ether solution
=112: 211.8；
The density of described boron trifluoride ether solution is 1.125, and wherein boron trifluoride contains 47%.
In described bromoethane diethyl ether solution preparatory phase, bromoethane described in described bromoethane diethyl ether solution and the body of ether
Long-pending portion rate is bromoethane: ether=335: 200.
In described boron triethyl tetrahydrofuran solution preparatory phase, ether is mixed with metal magnesium powder, is subsequently adding
Boron trifluoride ether solution, then it is added dropwise to bromoethane diethyl ether solution, start stirring after adding boron trifluoride ether solution, stirred
Journey drips bromoethane diethyl ether solution, during dropping bromoethane diethyl ether solution, need to first heat to aether backflow temperature
Lower dropping is the most continuously stirred, continues stirring after dropping at a temperature of aether backflow, and mixing time need to be more than 0.5h, it is thus achieved that three
Ethyl borate ether turbid solution.
Being stood at normal temperatures by described boron triethyl ether turbid solution, time of repose need to be more than 12h, it is thus achieved that supernatant, heavy
Fall thing, washs precipitum ether, and reclaims cleaning mixture, supernatant is heated to 45 DEG C, is steamed back by ether
Receive, then supernatant is warming up to 150 DEG C, steam acquisition boron triethyl, when no liquid distillates and emerge Bai Yanshi, and boron triethyl steams
Go out, stopped heating, boron triethyl is imported in oxolane, obtain boron triethyl tetrahydrofuran solution.
Described lithium triethylborohydride tetrahydrofuran solution preparatory phase need to be carried out in ice-water bath,
Being added in described oxolane by described lithium hydride, and be stirred, mixing time is more than 10min, configures dense
Degree is the lithium hydride tetrahydrofuran solution of 0.02g/ml；
In described lithium hydride tetrahydrofuran solution, drip described boron triethyl tetrahydrofuran solution, and be stirred, stir
When mixing, need to be warming up to oxolane reflux temperature with oil bath, described oxolane reflux temperature is 65 DEG C, and mixing time is more than
12h；Then stand 12h, be passed through nitrogen, be filtrated to get filtering residue, unreacted lithium hydride and lithium triethylborohydride oxolane
Solution, distills lithium triethylborohydride tetrahydrofuran solution, it is thus achieved that concentration is the lithium triethylborohydride four of 1mol/L
Hydrogen tetrahydrofuran solution.
The concentration of described boron triethyl tetrahydrofuran solution is 98g/300ml, described lithium hydride tetrahydrofuran solution with drip
Add the volume parts of boron triethyl tetrahydrofuran solution than for lithium hydride tetrahydrofuran solution: boron triethyl tetrahydrofuran solution=
2∶1。
By the preparation method of the lithium triethylborohydride tetrahydrofuran solution that the technique scheme of the present invention obtains, its
Provide the benefit that:
Preparation process is stable, it is ensured that the lithium triethylborohydride tetrahydrofuran solution quality of preparation.
Detailed description of the invention
Below the present invention is specifically described.
The preparation method of a kind of lithium triethylborohydride tetrahydrofuran solution, its step includes prepared by bromoethane diethyl ether solution
Stage, boron triethyl tetrahydrofuran solution preparatory phase, lithium triethylborohydride tetrahydrofuran solution preparatory phase,
Described bromoethane diethyl ether solution preparatory phase is physical reactions, it is thus achieved that bromoethane diethyl ether solution；
Reaction equation prepared by described boron triethyl tetrahydrofuran solution is:
3C2H5Br+3Mg+BF3.Et2O→(C2H5)3B+3MgBrF
Described boron triethyl tetrahydrofuran solution preparatory phase is prepared raw material and is included ether, boron trifluoride ether solution, gold
Belong to magnesium powder, bromoethane diethyl ether solution and oxolane, after distilling out the ether of less than 40 DEG C, be 90-92 DEG C receiving boiling point
Boron triethyl, flows directly in oxolane.Prepare boron triethyl tetrahydrofuran solution；
Reaction equation prepared by described lithium triethylborohydride tetrahydrofuran solution is:
Described lithium triethylborohydride tetrahydrofuran solution preparatory phase prepare raw material include oxolane, lithium hydride,
Boron triethyl tetrahydrofuran solution, nitrogen.
In described boron triethyl tetrahydrofuran solution preparatory phase, ether is mixed with metal magnesium powder, is subsequently adding
Boron trifluoride ether solution, then it is added dropwise to bromoethane diethyl ether solution, wherein:
The volume parts of described ether and the boron trifluoride ether solution of addition is than for ether: boron trifluoride ether solution=
1600∶148.8；
The mass fraction ratio of described metal magnesium powder and boron trifluoride ether solution is for metal magnesium powder: boron trifluoride ether solution
=112: 211.8；
The density of described boron trifluoride ether solution is 1.125, wherein containing boron trifluoride 47%.
In described bromoethane diethyl ether solution preparatory phase, the volume parts ratio of described bromoethane and ether is for bromoethane: second
Ether=335: 200.
In described boron triethyl tetrahydrofuran solution preparatory phase, ether is mixed with metal magnesium powder, is subsequently adding
Boron trifluoride ether solution, then it is added dropwise to bromoethane diethyl ether solution, start stirring after adding boron trifluoride ether solution, stirred
Journey drips bromoethane diethyl ether solution, during dropping bromoethane diethyl ether solution, need to first heat to aether backflow temperature
Lower dropping is the most continuously stirred, continues stirring after dropping at a temperature of aether backflow, and mixing time need to be more than 8h, it is thus achieved that three second
Base borate ether turbid solution.
Being stood at normal temperatures by described boron triethyl ether turbid solution, time of repose need to be more than 12h, it is thus achieved that supernatant, heavy
Fall thing, washs precipitum ether, and reclaims cleaning mixture, supernatant is heated to 45 DEG C, is steamed back by ether
Receive, then supernatant is warming up to 150 DEG C, steam acquisition boron triethyl, when no liquid distillates and emerge Bai Yanshi, and boron triethyl steams
Go out, stopped heating, boron triethyl is imported in oxolane, obtain boron triethyl tetrahydrofuran solution.
Described lithium triethylborohydride tetrahydrofuran solution preparatory phase need to be carried out in ice-water bath,
Being added in described oxolane by described lithium hydride, and be stirred, mixing time is more than 10min, configures dense
Degree is the lithium hydride tetrahydrofuran solution of 0.02g/ml；
In described lithium hydride tetrahydrofuran solution, drip described boron triethyl tetrahydrofuran solution, and be stirred, stir
When mixing, need to be warming up to oxolane reflux temperature with oil bath, described oxolane reflux temperature is 65 DEG C, and mixing time is more than
12h；Then stand 12h, be passed through nitrogen, be filtrated to get filtering residue, unreacted lithium hydride and lithium triethylborohydride oxolane
Solution, distills lithium triethylborohydride tetrahydrofuran solution, it is thus achieved that concentration is the lithium triethylborohydride four of 1mol/L
Hydrogen tetrahydrofuran solution.
The concentration of described boron triethyl tetrahydrofuran solution is 98g/300ml, described lithium hydride tetrahydrofuran solution with drip
Add the volume parts of boron triethyl tetrahydrofuran solution than for lithium hydride tetrahydrofuran solution: boron triethyl tetrahydrofuran solution=
2∶1。
Embodiment 1
The boiling point of boron triethyl 95 DEG C, relative density: 5.0, flash-point :-35.56 DEG C, this product is colourless transparent liquid, at sky
Can be natural in gas, to meet water or oxidant vigorous reaction, 100 DEG C of decomposition, be dissolved in ether, oxolane and ethanol, it is to prepare
The raw material of lithium triethylborohydride tetrahydrofuran solution.
Equipped with stirring, in the 3000ml there-necked flask of 100ml constant pressure funnel and reflux condensing tube, add ether
1600ml, adds metal magnesium powder 112g, adds boron trifluoride ether solution 148.8ml (closing 211.8g), starts stirring, simultaneously handle
The bromoethane diethyl ether solution that configured in advance is good is slowly dropped in the material of above-mentioned there-necked flask.
The collocation method of bromoethane diethyl ether solution is that 335ml (closing 488g) bromoethane and 200ml ether are thoroughly mixed i.e.
Can.
Dripping under aether backflow, the time is about 6 hours.After dropping, it is warmed up to, at a temperature of aether backflow, continue
Continuous stirring 2 hours.Stop heating, stop stirring, stand more than 12 hours.
The supernatant of reactant is poured out, and with pure ether secondary washing precipitum, cleaning mixture reclaims.
Supernatant heat temperature raising, collecting less than 45 DEG C and steam thing, this thing is ether, recycling, continues to be warmed up to 150
DEG C, in there-necked flask, no liquid distillates and emits white cigarette in a small amount.Stop heating.The thing that steams of more than 90 DEG C is boron triethyl, due to
Boron triethyl chemism is the highest, in atmosphere can spontaneous combustion.Distillates must be flowed directly in oxolane, oxolane pair
Boron triethyl shields.
The operating procedure of this process is, a 1000ml there-necked flask is weighed title, is simultaneously introduced 100ml oxolane also
Weighed title, record this secondary weight, this there-necked flask is connected to alembic, the boron triethyl steamed is fed directly to four
In hydrogen furan, at the end of distillation, there-necked flask is carried out scale and claims, calculate the accurate weight of the boron triethyl of collection.
The compound experiment of table 1 boron triethyl
If ether addition is less, then liquid becomes the most thick, it is impossible to continue stirring.As tested 3 and testing 4.
The there-necked flask of 2 1000ml of embodiment is placed in ice-water bath, adds oxolane 600ml, adds from hydrogen manufacturing
Change lithium (purity 97.56%) 12g, load onto stirring and start, at this moment owing to just adding lithium hydride meeting heat release in THF, therefore use ice
After water-bath cooling and stirring 10 minutes, being positioned over boron triethyl oxolane 300ml in constant pressure funnel (wherein containing boron triethyl
98g) it is slowly added dropwise in there-necked flask, uses oil bath heat temperature raising, (65 DEG C) stirring reaction 12 hours under oxolane refluxes,
After cooling stands 12 hours, being passed through nitrogen, through being filtrated to get a colourless transparent liquid, filtering residue reclaims, and uses for next group reaction again.
Obtain certain density lithium triethylborohydride after testing.
Embodiment 3
Steam certified products
Calculate the quantity of the oxolane that need to steam, steam unnecessary THF, obtain three second that concentration is 1mol/L
Base lithium borohydride solution
Technique scheme only embodies the optimal technical scheme of technical solution of the present invention, those skilled in the art
Some variations may made some of which part all embody the principle of the present invention, belong to protection scope of the present invention it
In.
Claims (7)
1. a preparation method for lithium triethylborohydride tetrahydrofuran solution, its step includes that bromoethane diethyl ether solution prepares rank
Section, boron triethyl tetrahydrofuran solution preparatory phase, lithium triethylborohydride tetrahydrofuran solution preparatory phase, its feature exists
In,
Described bromoethane diethyl ether solution preparatory phase is physical reactions, it is thus achieved that bromoethane diethyl ether solution；
Reaction equation prepared by described boron triethyl tetrahydrofuran solution is:
Described boron triethyl tetrahydrofuran solution preparatory phase is prepared raw material and is included ether, boron trifluoride ether solution, magnesium metal
Powder, bromoethane diethyl ether solution, through distilling out ether, then receive the boron triethyl that boiling point is 90-92 DEG C, flow directly into oxolane
In.Prepare boron triethyl tetrahydrofuran solution；
Reaction equation prepared by described lithium triethylborohydride tetrahydrofuran solution is:
The raw material of preparing of described lithium triethylborohydride tetrahydrofuran solution preparatory phase includes oxolane, lithium hydride, three second
Base boron tetrahydrofuran solution, nitrogen.
2. according to the preparation method of the lithium triethylborohydride tetrahydrofuran solution described in claim 1, it is characterised in that institute
State in boron triethyl tetrahydrofuran solution preparatory phase, ether is mixed with metal magnesium powder, be subsequently adding boron trifluoride second
Ethereal solution, then it is added dropwise to bromoethane diethyl ether solution, wherein:
The volume parts of described ether and the boron trifluoride ether solution of addition is than for ether: boron trifluoride ether solution=1600
∶148.8；
The mass fraction of described metal magnesium powder and boron trifluoride ether solution is than for metal magnesium powder: boron trifluoride ether solution=
112∶211.8；
The density of described boron trifluoride ether solution is 1.125, wherein containing boron trifluoride 47%.
3. according to the preparation method of the lithium triethylborohydride tetrahydrofuran solution described in claim 1, it is characterised in that institute
Stating in bromoethane diethyl ether solution preparatory phase, bromoethane described in described bromoethane diethyl ether solution with the volume parts ratio of ether is
Bromoethane: ether=335: 200.
4. according to the preparation method of the lithium triethylborohydride tetrahydrofuran solution described in claim 1, it is characterised in that institute
State in boron triethyl tetrahydrofuran solution preparatory phase, ether is mixed with metal magnesium powder, be subsequently adding boron trifluoride second
Ethereal solution, then it is added dropwise to bromoethane diethyl ether solution, start stirring after adding boron trifluoride ether solution, whipping process is added dropwise to
Bromoethane diethyl ether solution, during dropping bromoethane diethyl ether solution, need to drip also at a temperature of first heating to aether backflow
Continuously stirred, at a temperature of aether backflow, continue stirring after dropping, mixing time need to be more than 0.5h, it is thus achieved that boron triethyl second
Ether turbid solution.
5. according to the preparation method of the lithium triethylborohydride tetrahydrofuran solution described in claim 4, it is characterised in that will
Described boron triethyl ether turbid solution stands at normal temperatures, and time of repose need to be more than 12h, it is thus achieved that supernatant, precipitum, will sedimentation
Thing ether washs, and reclaims cleaning mixture, and supernatant is heated to 45 DEG C, and ether steams recovery, then by supernatant
Liquid is warming up to 150 DEG C, steams acquisition boron triethyl, when no liquid distillates and emerge Bai Yanshi, and boron triethyl has steamed, stops
Heating, imports boron triethyl in oxolane, obtains boron triethyl tetrahydrofuran solution.
6. according to the preparation method of the lithium triethylborohydride tetrahydrofuran solution described in claim 1, it is characterised in that institute
State lithium triethylborohydride tetrahydrofuran solution preparatory phase to carry out in ice-water bath,
Being added in described oxolane by described lithium hydride, and be stirred, mixing time is more than 10min, and configuring concentration is
The lithium hydride tetrahydrofuran solution of 0.02g/ml；
In described lithium hydride tetrahydrofuran solution, drip described boron triethyl tetrahydrofuran solution, and be stirred, during stirring,
Need to be warming up to oxolane reflux temperature with oil bath, described oxolane reflux temperature is 65 DEG C, and mixing time is more than 12h；So
Rear standing 12h, is passed through nitrogen, is filtrated to get filtering residue, unreacted lithium hydride and lithium triethylborohydride tetrahydrofuran solution, will
Lithium triethylborohydride tetrahydrofuran solution distills, it is thus achieved that concentration is that the lithium triethylborohydride oxolane of 1mol/L is molten
Liquid.
7. according to the preparation method of the lithium triethylborohydride tetrahydrofuran solution described in claim 6, it is characterised in that institute
The concentration stating boron triethyl tetrahydrofuran solution is 98g/300ml, described lithium hydride tetrahydrofuran solution and dropping boron triethyl
The volume parts of tetrahydrofuran solution is than for lithium hydride tetrahydrofuran solution: boron triethyl tetrahydrofuran solution=2: 1.
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Cited By (5)
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| CN106947072A (en) * | 2017-04-20 | 2017-07-14 | 宁波浙铁大风化工有限公司 | A kind of preparation technology of makrolon |
| CN110187050A (en) * | 2018-02-23 | 2019-08-30 | 山西燕京啤酒有限公司 | The detection method of a set of judgement tetrahydro misery quality for being applicable in beer enterprise |
| CN113527344A (en) * | 2021-07-02 | 2021-10-22 | 广东天诚生物降解材料有限公司 | Preparation method of alkyl boron tetrahydrofuran solution |
| CN114394987A (en) * | 2022-01-27 | 2022-04-26 | 沧州临港星辰化工有限公司 | Preparation method of trialkyl lithium borohydride |
| CN115894540A (en) * | 2022-04-08 | 2023-04-04 | 安徽泽升科技有限公司 | Preparation method of lithium tri-sec-butyl borohydride |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106947072A (en) * | 2017-04-20 | 2017-07-14 | 宁波浙铁大风化工有限公司 | A kind of preparation technology of makrolon |
| CN110187050A (en) * | 2018-02-23 | 2019-08-30 | 山西燕京啤酒有限公司 | The detection method of a set of judgement tetrahydro misery quality for being applicable in beer enterprise |
| CN110187050B (en) * | 2018-02-23 | 2023-04-11 | 山西燕京啤酒有限公司 | Detection method for judging quality of tetrahydrochysene bitter water suitable for beer enterprises |
| CN113527344A (en) * | 2021-07-02 | 2021-10-22 | 广东天诚生物降解材料有限公司 | Preparation method of alkyl boron tetrahydrofuran solution |
| CN114394987A (en) * | 2022-01-27 | 2022-04-26 | 沧州临港星辰化工有限公司 | Preparation method of trialkyl lithium borohydride |
| CN114394987B (en) * | 2022-01-27 | 2022-08-05 | 沧州临港星辰化工有限公司 | Preparation method of trialkyl lithium borohydride |
| CN115894540A (en) * | 2022-04-08 | 2023-04-04 | 安徽泽升科技有限公司 | Preparation method of lithium tri-sec-butyl borohydride |
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