CN105085467B - The preparation method of 1,3 propane sultone derivatives - Google Patents
The preparation method of 1,3 propane sultone derivatives Download PDFInfo
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- CN105085467B CN105085467B CN201510534904.7A CN201510534904A CN105085467B CN 105085467 B CN105085467 B CN 105085467B CN 201510534904 A CN201510534904 A CN 201510534904A CN 105085467 B CN105085467 B CN 105085467B
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- reaction
- sultones
- propane
- propene
- fluoro
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- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical class O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 19
- 238000003682 fluorination reaction Methods 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 8
- -1 propene sultones Chemical class 0.000 claims abstract description 5
- 239000002994 raw material Substances 0.000 claims abstract description 4
- RQXXCWHCUOJQGR-UHFFFAOYSA-N 1,1-dichlorohexane Chemical compound CCCCCC(Cl)Cl RQXXCWHCUOJQGR-UHFFFAOYSA-N 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 69
- 238000006243 chemical reaction Methods 0.000 claims description 50
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 25
- 239000001294 propane Substances 0.000 claims description 25
- 230000035484 reaction time Effects 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 6
- IFDLFCDWOFLKEB-UHFFFAOYSA-N 2-methylbutylbenzene Chemical compound CCC(C)CC1=CC=CC=C1 IFDLFCDWOFLKEB-UHFFFAOYSA-N 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 241000255964 Pieridae Species 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000002596 lactones Chemical class 0.000 claims 1
- 239000000654 additive Substances 0.000 abstract description 14
- 230000000996 additive effect Effects 0.000 abstract description 14
- 239000003792 electrolyte Substances 0.000 abstract description 9
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 abstract description 6
- 229910001416 lithium ion Inorganic materials 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 150000002500 ions Chemical class 0.000 abstract description 2
- 239000004094 surface-active agent Substances 0.000 abstract description 2
- 239000007789 gas Substances 0.000 description 11
- 238000005868 electrolysis reaction Methods 0.000 description 3
- 229910001290 LiPF6 Inorganic materials 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910032387 LiCoO2 Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000008053 sultones Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/04—Five-membered rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Secondary Cells (AREA)
Abstract
1, the preparation method of 3 propane sultone derivatives, belong to the technical field of compound preparation, raw materials used this method is 1,3 propene sultones, by 1,3 propene sultones are placed in dichloro hexane, then fluorization agent is added thereto and directly carries out fluorination reaction, obtains 1,3 propane sultone derivatives.The present invention prepare 1,3 propane sultone derivatives, in addition to can be as intermediate, double ion surfactant and sulfonating agent, it is also used as the additive of electrolyte of lithium-ion secondary battery, especially because the presence of F elements, cell voltage can be more improved, lithium ion battery high-voltage field is can be widely applied to.
Description
Technical field
The invention belongs to technical field prepared by compound, it is related to the preparation of 1,3- propane sultone derivatives, has
The preparation method for 1,3- propane sultone derivatives of body.
Background technology
With the development of the electronics and information industry of China, the demand for electrochmical power source is increasing, will to its performance
Seek more and more higher.Due to lithium ion battery have small volume, have a safety feature, lightweight, specific energy is high, voltage is high, long lifespan,
The incomparable advantage of other electrochmical power sources such as pollution-free, at present it have become mobile phone, palm PC, notebook computer,
The main power source of the portable electric appts such as microcam digital camera.In recent years, the basic research of lithium ion battery and
Application and development turns into one of focus.Lithium battery includes positive pole, negative pole, electrolyte and barrier film, still, and battery is in charge and discharge process
In, heat can be discharged, causes battery performance to reduce.And battery can discharge heat in charge and discharge process, battery performance is caused to drop
Low, the poor performance of battery when existing electrolysis additive runs into high-temperature condition in use is damaged seriously, is not added with additive
Battery high-temperature circulate 50 weeks after, serious capacity reduction can be produced, in order to overcome disadvantage mentioned above, it is a kind of that we are directed to research
Electrolysis additive, can effectively improve the performance of battery under high-temperature condition.
In the prior art, a kind of fluoro- 1, the 3- propane sultones of 3- are reported in the A of Patent No. CN 103044384
Preparation method, makes 1,3- propane sultones carry out chlorination, generates chloro- 1, the 3- propane sultones of 3-, then makes 3- chloro-
1,3- propane sultones carry out halogen exchange reaction to obtain in the presence of a phase transfer catalyst with fluorization agent in a solvent
Product.The method needs first to carry out chloro, and pollution is big, and step is long, and yield is not high.
The content of the invention
There is provided preparation side derived from 1,3- of one kind propane sultones to solve defect of the prior art by the present invention
Method.
The present invention is to realize that the technical scheme that its purpose is used is：
The preparation method of 1,3- propane sultone derivative, raw materials used this method is 1,3- propene sulfonic acid esters, by 1,
3- propene sultones are placed in dichloro hexane, and the direct row fluorination reaction of fluorization agent is then added thereto, 1,3- propane is obtained
Sultones derivative.The present invention use dichloromethane for anti-solvent, it is to avoid 1, the 3- propene sultone derivatives generated
Hydrolyze, substantially increase the yield of 1,3- alkene sultones derivatives.
It is 1-10atm that reaction pressure is controlled in the fluorination reaction, and reaction temperature is 10-50 DEG C, is 1-10h between reaction.
In the fluorination reaction, the mol ratio of control fluorization agent and 1,3- propene sultone is 1：(1-1.3), reacts
To the fluoro- 1,3- propane sultones of 2-.
The fluorization agent is HF, and the derivative prepared is fluoro- 1, the 3- propane sultones of 2-.
In the fluorination reaction, the mol ratio of control fluorization agent and 1,3- propene sultone is 1：(2-3), should obtain 1,
The fluoro- 1,3- propane sultones of 2- bis-.
The fluorization agent is fluorine gas, and the derivative prepared is fluoro- 1, the 3- propane sultones of 1,2- bis-.
The amount of dichloromethane used in 1mol 1,3- propene sultones is 200-800ml.
The chemical structural formula of the fluoro- 1,3- propane sultones of 2- is in the present invention：
The chemical structural formula of fluoro- 1, the 3- propane sultones of 1,2- bis- is in the present invention：
The beneficial effects of the invention are as follows：1,3- propane sultone derivatives prepared by the present invention, except can as intermediate,
Outside double ion surfactant and sulfonating agent, the additive of electrolyte of lithium-ion secondary battery is also used as, especially because F
The presence of element, can more improve cell voltage, can be widely applied to lithium ion battery high-voltage field.Meanwhile, 1,2-
Two fluoro- 1,3- propane sultones can also improve the high-temperature cycle of current ternary battery material, can improve battery
Cycle life.
The present invention prepares 1,3- propane sultone derivatives and uses 1,3- propene sultones and fluorization agent single step reaction,
High income, pollutes small.The present invention is by strictly controlling the reaction ratio of 1,3- propene sultones and fluorization agent, reaction pressure and anti-
Temperature is answered, overcomes that the directly reaction of organic matter and fluorization agent is whard to control, the technology prejudice more than side reaction, course of reaction is gentle,
Selectivity is good, it is easy to control, and is raw material using 1,3 propene sultone, and itself has double bond, can carry out addition reaction, instead
Should easily it manipulate.The control of reaction pressure and reaction temperature is the key for realizing this effect, and pressure is low, and the reaction time is long；Pressure is high,
It is dangerous high；Reaction temperature is low, and the reaction time can increase, and reaction temperature is high, easily produces side reaction.Inventor passes through long-term
Summarize, the reaction condition that single step reaction prepares 1,3- propene sultone derivatives has been obtained, wherein the difficulty overcome is difficult to use
Expressed by word, invented eventually through the unremitting effort of inventor and prepared 1,3- third available for the single step reaction of industrialized production
The preparation method of alkene sultones derivative.
Brief description of the drawings
Fig. 1 is battery in embodiment 1 added with the fluoro- 1,3- propane sultones of 1%2- and added without electrolyte
EIS before and after the battery of agent is circulated 50 weeks respectively at 65 DEG C schemes.
Fig. 2 is the battery and the electrolysis of addition basis in embodiment 2 added with fluoro- 1, the 3- propane sultones of 1%1,2- bis-
EIS before and after the battery of solution additive is circulated 50 weeks respectively at 65 DEG C schemes.
Embodiment
The present invention produces 1,3- to solve the defect of the poor performance of battery during high-temperature condition in the prior art there is provided one kind
The method of propane sultone derivative, for the additive of battery electrolyte, makees with reference to specific embodiment to the present invention
Further instruction.
First, the fluoro- 1,3- propane sultones of 2- are prepared
Embodiment 1
Using dichloromethane as reaction dissolvent, 1mol 1,3- propene sultones are added in 200ml dichloromethane,
Then pass to HF gases, control reaction pressure be 1atm, reaction temperature be 10 DEG C of reaction time be 1h, obtain fluoro- 1, the 3- third of 2-
Sultone, calculated yield is that 46.0%, purity is that 99.4%, product moisture is 16PPM.
Embodiment 2
Using dichloromethane as reaction dissolvent, 1mol 1,3- propene sultones are added in 400ml dichloromethane,
Then pass to HF gases, control reaction pressure be 7atm, reaction temperature be 35 DEG C of reaction time be 5h, obtain fluoro- 1, the 3- third of 2-
Sultone, calculated yield is that 74.4%, purity is that 99.6%, product moisture is 17PPM.
Embodiment 3
Using dichloromethane as reaction dissolvent, 1mol 1,3- propene sultones are added in 800ml dichloromethane,
Then pass to HF gases, control reaction pressure be 10atm, reaction temperature be 50 DEG C of reaction time be 10h, obtain 2- fluoro- 1,3-
Propane sultone, calculated yield is that 87.2%, purity is that 99.8%, product moisture is 18PPM.
Embodiment 4
Using dichloromethane as reaction dissolvent, 1mol 1,3- propene sultones are added in 300ml dichloromethane,
Then pass to HF gases, control reaction pressure be 5atm, reaction temperature be 22 DEG C of reaction time be 3h, obtain fluoro- 1, the 3- third of 2-
Sultone, calculated yield is that 68.7%, purity is that 99.48%, product moisture is 16PPM.
Embodiment 5
Using dichloromethane as reaction dissolvent, 1mol 1,3- propene sultones are added in 600ml dichloromethane,
Then pass to HF gases, control reaction pressure be 8.5atm, reaction temperature be 43 DEG C of reaction time be 8h, obtain 2- fluoro- 1,3-
Propane sultone, calculated yield is that 82.6%, purity is that 99.7%, product moisture is 17PPM.
2nd, fluoro- 1, the 3- propane sultones of 1,2- bis- are prepared
Embodiment 6
Using dichloromethane as reaction dissolvent, 1mol 1,3- propene sultones are added in 200ml dichloromethane,
Then pass to fluorine gas, control reaction pressure be 1atm, reaction temperature be 10 DEG C of reaction time be 1h, obtain 1,2- bis- fluoro- 1,3-
Propane sultone, calculated yield is that 56.0%, purity is that 99.4%, product moisture is 16PPM.
Embodiment 7
Using dichloromethane as reaction dissolvent, 1mol 1,3- propene sultones are added in 400ml dichloromethane,
Then pass to fluorine gas, control reaction pressure be 7atm, reaction temperature be 35 DEG C of reaction time be 5h, obtain 1,2- bis- fluoro- 1,3-
Propane sultone, calculated yield is that 89.5%, purity is that 99.6%, product moisture is 18PPM.
Embodiment 8
Using dichloromethane as reaction dissolvent, 1mol 1,3- propene sultones are added in 800ml dichloromethane,
Then pass to fluorine gas, control reaction pressure be 10atm, reaction temperature be 50 DEG C of reaction time be 10h, obtain 1,2- bis- fluoro- 1,
3- propane sultones, calculated yield is that 87.2%, purity is that 99.8%, product moisture is 18PPM.
Embodiment 9
Using dichloromethane as reaction dissolvent, 1mol 1,3- propene sultones are added in 300ml dichloromethane,
Then pass to fluorine gas, control reaction pressure be 5atm, reaction temperature be 22 DEG C of reaction time be 3h, obtain 1,2- bis- fluoro- 1,3-
Propane sultone, calculated yield is that 74.6%, purity is that 99.3%, product moisture is 17PPM.
Embodiment 10
Using dichloromethane as reaction dissolvent, 1mol 1,3- propene sultones are added in 600ml dichloromethane,
Then pass to fluorine gas, control reaction pressure be 8.5atm, reaction temperature be 43 DEG C of reaction time be 8h, obtain 1,2- bis- fluoro- 1,
3- propane sultones, calculated yield is that 88.3%, purity is that 99.7%, product moisture is 17PPM.
3rd, by the battery and the battery without additive of the additive added with the fluoro- 1,3- propane sultones of 1%2-
After 65 DEG C circulate 50 weeks, contrasted, comparing result is referring to Fig. 1, from figure 1 it appears that added with 1% present invention
Battery after the circulation 50 weeks of 65 DEG C of high temperature, capacity remains more than 90%, and be not added with additive of the present invention in high temperature 65
DEG C circulation 50 weeks after, capacity only be left 78%, illustrate that additive high temperature cyclic performance of the present invention is superior.
4th, by the battery added with the additive of fluoro- 1, the 3- propane sultones of 1%1,2- bis- and addition basic electrolyte
Battery respectively at 65 DEG C circulation 50 weeks after, contrasted, the positive pole of wherein battery is：4.35V LiCoO2, negative pole behaviour
Make graphite；The electrolyte of battery of wherein addition basic electrolyte is：DC/EMC=1/3, LiPF6：1.1M, FEC PST；Addition
The battery electrolyte of 1,2- bis- fluoro- 1,3- propane sultones is：DC/EMC=1/3, LiPF6：1.1M, FEC 1,2- bis- is fluoro-
1,3- propane sultone comparing results are referring to Fig. 2.
From figure 2 it can be seen that the battery added with 1% present invention is after the circulation 50 weeks of 65 DEG C of high temperature, capacity is remained
More than 80%, and be not added with additive of the present invention after the circulation 50 weeks of 65 DEG C of high temperature, capacity is only left 61%, illustrates the present invention
Additive high temperature cyclic performance is superior.
Claims (2)
- The preparation method of 1.1,3- propane sultone derivatives, it is characterised in that：Raw materials used this method is 1,3- propylene sulphurs Acid lactone, 1,3- propene sultones are placed in dichloro hexane, and fluorization agent is then added thereto and directly carries out fluorination reaction, Obtain controlling reaction pressure to be 7-10atm in 1,3- propane sultone derivatives, the fluorination reaction, reaction temperature is 35- 50 DEG C, the reaction time is 1-10h, and the fluorization agent is HF or fluorine gas, when fluorization agent is HF, in the fluorination reaction, control The mol ratio of fluorization agent and 1,3- propene sultones is 1：(1-1.3), reaction obtains fluoro- 1, the 3- propane sultones of 2-；When When fluorization agent is fluorine gas, in the fluorination reaction, the mol ratio of control fluorization agent and 1,3- propene sultone is 1：(2-3), Reaction obtains the fluoro- 1,3- propane sultones of 1,2- bis-.
- 2. a kind of preparation method of 1,3- propane sultones derivative according to claim 1, it is characterised in that：1mol 1,3- propene sultones used in dichloromethane amount be 200-800ml.
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| CN105481825A (en) * | 2015-12-31 | 2016-04-13 | 石家庄圣泰化工有限公司 | Preparation method of prop-1-ene-1,3-sultone derivatives |
| CN110777402B (en) * | 2019-11-21 | 2021-03-23 | 武汉奥邦表面技术有限公司 | Preparation method of acidic zinc-plated carrier |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103044384A (en) * | 2011-10-17 | 2013-04-17 | 张家港市国泰华荣化工新材料有限公司 | Preparation method of 3-fluorine-1, 3-propane sulfonic acid lactone |
| CN104662716A (en) * | 2012-06-06 | 2015-05-27 | 约翰逊控制技术公司 | Electrolyte formulation for high voltage and wide temperature lithium-ion cells |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103044384A (en) * | 2011-10-17 | 2013-04-17 | 张家港市国泰华荣化工新材料有限公司 | Preparation method of 3-fluorine-1, 3-propane sulfonic acid lactone |
| CN104662716A (en) * | 2012-06-06 | 2015-05-27 | 约翰逊控制技术公司 | Electrolyte formulation for high voltage and wide temperature lithium-ion cells |
Non-Patent Citations (1)
| Title |
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| 碳碳不饱和键氟化加成反应的研究进展;陈新兵，等，;《有机化学》;20021231;第22卷(第10期);第694-701页 * |
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Address after: 051430 douyu Industrial Zone, Shijiazhuang City, Hebei Province Patentee after: Hebei Shengtai Materials Co., Ltd. Address before: 051430 douyu Industrial Zone, Shijiazhuang City, Hebei Province Patentee before: SHIJIAZHUANG SHENGTAI CHEMICAL Co.,Ltd. |