CN107840812A - The synthetic method of tosylate derivative - Google Patents

The synthetic method of tosylate derivative Download PDF

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Publication number
CN107840812A
CN107840812A CN201711123956.0A CN201711123956A CN107840812A CN 107840812 A CN107840812 A CN 107840812A CN 201711123956 A CN201711123956 A CN 201711123956A CN 107840812 A CN107840812 A CN 107840812A
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CN
China
Prior art keywords
synthetic method
tosylate derivative
ethylene glycol
reaction
tosylate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN201711123956.0A
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Chinese (zh)
Inventor
闫彩桥
刘鹏
侯荣雪
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SHIJIAZHUANG SHENGTAI CHEMICAL CO Ltd
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SHIJIAZHUANG SHENGTAI CHEMICAL CO Ltd
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Priority to CN201711123956.0A priority Critical patent/CN107840812A/en
Publication of CN107840812A publication Critical patent/CN107840812A/en
Priority to PCT/CN2018/084559 priority patent/WO2019095636A1/en
Priority to JP2018543310A priority patent/JP2021502950A/en
Priority to KR1020187023257A priority patent/KR102144626B1/en
Pending legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
    • C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/42—Separation; Purification; Stabilisation; Use of additives
    • C07C303/44—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/056—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes
    • H01M10/0564—Accumulators with non-aqueous electrolyte characterised by the materials used as electrolytes, e.g. mixed inorganic/organic electrolytes the electrolyte being constituted of organic materials only
    • H01M10/0566—Liquid materials
    • H01M10/0567—Liquid materials characterised by the additives
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/42—Methods or arrangements for servicing or maintenance of secondary cells or secondary half-cells
    • H01M10/4235—Safety or regulating additives or arrangements in electrodes, separators or electrolyte
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries

Abstract

The synthetic method of tosylate derivative, belong to the technical field of compound synthesis, withFor raw material, with ethylene glycol or R2OH reaction generationsOrWherein R1Selected from alkyl, H or F, R2Selected from pi-allyl, propargyl or benzene, concrete operations are, by ethylene glycol or R2OH is added in reactor with dichloromethane, is stirred lower addition organic base, is then cooled to less than 15 DEG C, start to be added dropwiseDrop finishes, and returns to room temperature and continues to stir 0.5 1h, then heating, the 2h of back flow reaction 1, after reaction completely, the processing of ice solution, layering, dries concentration, obtains tosylate derivative product.Synthetic method of the present invention is simple, and course of reaction is gentle, stably, high income, and obtained product purity is high.

Description

The synthetic method of tosylate derivative
Technical field
The invention belongs to the technical field of compound synthesis, and in particular to the synthetic method of tosylate derivative, this hair Bright synthetic method is simple, and course of reaction is gentle, stably, high income, and obtained product purity is high.
Background technology
It is increasing for the demand of electrochmical power source with the development of the electronics and information industry in China, will to its performance Seek more and more higher.Due to lithium ion battery have small volume, have a safety feature, in light weight, higher than energy, voltage is high, long lifespan, The advantages of other electrochmical power sources institute such as pollution-free is incomparable, 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, and still, 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 It is low, the poor performance of battery when existing electrolysis additive runs into high-temperature condition in use, it is damaged seriously, is not added with additive Battery high-temperature circulate 50 weeks after, can produce serious capacity reduces, and in order to overcome disadvantage mentioned above, it is a kind of that we are directed to research Electrolysis additive, it can effectively improve the performance of battery under high-temperature condition.
Tosylate derivative is important organic synthesis intermediate, is widely used, and we are it has been investigated that it can be applied In battery electrolyte, but its synthetic method is complicated, there is no a kind of method to be prepared into meeting wanting for battery electrolyte at present Ask.
The content of the invention
It is an object of the invention to provide a kind of benzene sulfonate derivative that can be prepared into and meet for battery electrolyte requirement The synthetic method of thing.The present invention is to realize that the technical scheme that its purpose uses is：
The synthetic method of tosylate derivative,
WithFor raw material, with ethylene glycol or R2- OH reaction generationsWherein R1Selected from alkyl, H or F, R2Choosing From pi-allyl, propargyl or benzene, concrete operations are, by ethylene glycol or R2- OH is added in reactor with dichloromethane, and stirring is lower to be added Enter organic base, the addition of organic base is the 1-5% of material quality, then cools to less than 15 DEG C, starts to be added dropwiseDrop finishes, and returns to room temperature and continues to stir 0.5-1h, then heating, back flow reaction 1-2h, after reaction completely, The processing of ice solution, ice solution is carried out with 5-10 times of frozen water, is layered, and is dried concentration, is obtained tosylate derivative product.
Described organic base is triethylamine or pyridine.
During using ethylene glycol, controlMol ratio with ethylene glycol is (2-2.3)：1；Using R2-OH When, controlWith R2- OH mol ratio is (1-1.3)：1.
Obtained tosylate derivative is recrystallized into (such as DMC), obtains tosylate derivative sterling.
The beneficial effects of the invention are as follows：
Synthetic method of the present invention is simple, efficiently, is adapted to industrialized production, and high income is up to more than 90%, high purity More than 99.9%, by the control of technological parameter, the collocation of process, the processing of three-stage temperature control method and the selection of material, make The moisture of the benzene sulfonic derivative of preparation is few≤50ppm, acid number is low≤50ppm, has established that to strengthen battery after its application high The basis of low-temperature stability.
Brief description of the drawings
Fig. 1 is the 1H NMR spectras of 1- phenyl benzene sulphonic acid esters.
Fig. 2 is the 13C NMR spectras of 1- phenyl benzene sulphonic acid esters.
Fig. 3 is the 1H NMR spectras of benzene sulfonic acid allyl ester.
Fig. 4 is the 13C NMR spectras of benzene sulfonic acid allyl ester.
Fig. 5 is the 1H NMR spectras of Glycol dibenzenesulfonate.
Fig. 6 is the 13C NMR spectras of Glycol dibenzenesulfonate.
Embodiment
With reference to specific embodiment, the present invention is further illustrated.
First, specific embodiment
Embodiment 1
1.0mol phenol and 500ml dichloromethane are added in reaction bulb respectively, lower addition triethylamine is stirred, then cools To less than 15 DEG C, start that benzene sulfonyl chloride 1.1mol is added dropwise, drop finishes, and returns to room temperature and continues to stir 1h, is then warming up to backflow and continues 2h is reacted, after vapor detection reaction completely, the processing of ice solution, layering, concentration is dried, obtains crude product and then be recrystallized to give sterling 222.3g, the yield for calculating product are 95%.Detection purity is 99.93%, moisture 30ppm, acid number 34ppm, is determined Density is 1.277g/cm3, boiling point is 375.4 DEG C of 760mmHg, and its 1H NMR spectra is as shown in figure 1,13CNMR collection of illustrative plates such as Fig. 2 institutes Show.
Synthetic route is：
Embodiment 2
1.0mol allyl alcohols and 500ml dichloromethane are added in reaction bulb respectively, lower addition pyridine is stirred, then cools To less than 15 DEG C, start that benzene sulfonyl chloride 2.1mol is added dropwise, drop finishes, and returns to room temperature and continues to stir 1h, is then warming up to backflow and continues 2h is reacted, after vapor detection reaction completely, the processing of ice solution, layering, concentration is dried, obtains crude product and then be recrystallized to give sterling 189.3g, the yield for calculating product are 95.5%.Detection purity is 99.95%, moisture 30ppm, acid number 40ppm, its 1H NMR spectras are as shown in figure 3,13C NMR spectras are as shown in Figure 4.
Synthetic route is：
Embodiment 3
1.0mol propargyl alcohols and 500ml dichloromethane are added in reaction bulb respectively, lower addition triethylamine is stirred, then drops Temperature to less than 15 DEG C, start be added dropwise benzene sulfonyl chloride 2.1mol, drop finish, return to room temperature continue stir 1h, be then warming up to flow back after Continuous reaction 2h, after vapor detection reaction completely, the processing of ice solution, layering, concentration is dried, obtain crude product and then be recrystallized to give sterling 187.77g calculated yield 95.8%.It is 99.93% to detect purity, moisture 28ppm, acid number 36ppm, and density is 1.244g/mL。
Synthetic route is：
Embodiment 4
1.0mol ethylene glycol and 500ml dichloromethane are added in reaction bulb respectively, lower addition pyridine is stirred, then cools To less than 15 DEG C, start that benzene sulfonyl chloride 2.1mol is added dropwise, drop finishes, and returns to room temperature and continues to stir 1h, is then warming up to backflow and continues 2h is reacted, after vapor detection reaction completely, the processing of ice solution, layering, concentration is dried, obtains crude product and then be recrystallized to give sterling, The yield for calculating product is 94.3%.It is 99.91% to detect purity, moisture 26ppm, acid number 35ppm, and density is 1.387g/cm3, boiling point is 516.1 DEG C, 760mmHg, and its 1H NMR spectra is as shown in figure 5,13C collection of illustrative plates is as shown in Figure 6.
Synthetic route is：
Embodiment 5
1.0mol ethylene glycol and 500ml dichloromethane are added in reaction bulb respectively, lower addition triethylamine is stirred, then drops Temperature starts the trimethylbenzene chloride 2.1mol of dropwise addition 2,4,6- to less than 15 DEG C, and drop finishes, and returns to room temperature and continues to stir 1h, then It is warming up to backflow to continue to react 2h, after vapor detection reaction completely, the processing of ice solution, layering, dries concentration, obtain crude product and then weight Crystallization obtains sterling (CAS 128584-68-9), calculated yield 94.6%.It is 99.9% to detect purity, moisture 38ppm, acid number 45ppm, density 1.239g/cm3, boiling point is 588.8 DEG C, 760mmHg.
Synthetic route is：
Embodiment 6
1.0mol ethylene glycol and 500ml dichloromethane are added in reaction bulb respectively, lower addition pyridine is stirred, then cools To less than 15 DEG C, start the trifluoro benzene sulfonyl chloride 2.1mol of dropwise addition 2,4,6-, drop finishes, and returns to room temperature and continues to stir 1h, then heats up Continue to react 2h to backflow, after vapor detection reaction completely, the processing of ice solution, layering, dry concentration, obtain crude product and then recrystallize Sterling is obtained, the yield for calculating product is 93.8%.It is 99.94% to detect its purity, moisture 35ppm, acid number 42ppm。
Synthetic route is：
2nd, application test
1st, it is the lithium battery added with 1% tosylate derivative of the present invention of electrolyte weight, the lithium battery not added is empty The lithium battery of existing tosylate derivative is compareed, added in vain after 65 DEG C of circulations, is contrasted, with the gained of embodiment 1 Exemplified by product, wherein the purity of tosylate derivative of the present invention is 99.93%, moisture 30ppm, acid number 34ppm；It is existing The purity for having benzene sulfonic derivative control 1 is 99.93%, acid number 150ppm, moisture 138ppm；Existing benzene sulfonic derivative The purity of control 2 is 95%, acid number 150ppm, moisture 138ppm results such as table 1 below：
Table 1
As shown in Table 1, tosylate derivative of the present invention can improve the high temperature cyclic performance of battery.
2nd, battery high-temperature storge quality is evaluated：60 DEG C/30D and 85 DEG C/7D storage performances are tested, and following table 2 is battery warp 60 DEG C of storages are deposited 7 days for 30 days and 85 DEG C again after hand standard discharge and recharge, then measure the capability retention and capacity restoration of battery Rate.
Table 2
As shown in Table 2, tosylate derivative of the present invention can improve the high-temperature storage performance of battery.
3rd, battery low-temperature storage performance evaluation；Table 3 below is that battery is shelved in cryogenic box, and it is -30 to control temperature respectively DEG C or -40 DEG C, shelve time 240min, then measure battery capability retention.
Table 3
As shown in Table 3, tosylate derivative of the present invention can improve the low-temperature storage performance of battery.Above-mentioned performance detection By taking embodiment 1 as an example, the performance of other tosylate derivatives and above-mentioned performance are basically identical, and performance difference is on 2-4% Lower floating, illustrate that purity, acid number and the moisture of tosylate derivative are applied to the presence of the battery performance after battery Critical influence, at the same table 2 and the indirect proof of table 3 tosylate derivative of the present invention can improve battery placement it is steady It is qualitative, improve the service life of battery.

Claims (4)

1. the synthetic method of tosylate derivative, it is characterised in that
WithFor raw material, with ethylene glycol or R2- OH reaction generationsWherein R1Selected from alkyl, H or F, R2Choosing From pi-allyl, propargyl or benzene, concrete operations are, by ethylene glycol or R2- OH is added in reactor with dichloromethane, and stirring is lower to be added Enter organic base, then cool to less than 15 DEG C, start to be added dropwiseDrop finishes, and returns to room temperature and continues to stir 0.5- 1h, then heating, back flow reaction 1-2h, after reaction completely, the processing of ice solution, layering, dry concentration, obtain tosylate derivative Product.
2. the synthetic method of tosylate derivative according to claim 1, it is characterised in that described organic base is three Ethamine or pyridine.
3. the synthetic method of tosylate derivative according to claim 1, it is characterised in that during using ethylene glycol, control SystemMol ratio with ethylene glycol is (2-2.3)：1；Using R2During-OH, controlWith R2- Oh mol ratio is (1-1.3)：1.
4. the synthetic method of tosylate derivative according to claim 1, it is characterised in that the benzene sulfonate that will be obtained Derivative is recrystallized, and obtains tosylate derivative sterling.
CN201711123956.0A 2017-11-14 2017-11-14 The synthetic method of tosylate derivative Pending CN107840812A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CN201711123956.0A CN107840812A (en) 2017-11-14 2017-11-14 The synthetic method of tosylate derivative
PCT/CN2018/084559 WO2019095636A1 (en) 2017-11-14 2018-04-26 Method for synthesizing benzenesulfonate derivative
JP2018543310A JP2021502950A (en) 2017-11-14 2018-04-26 Method for synthesizing benzenesulfonic acid ester derivative
KR1020187023257A KR102144626B1 (en) 2017-11-14 2018-04-26 A method for synthesis of benzene sulfonate derivatives

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109004279A (en) * 2018-07-18 2018-12-14 石家庄圣泰化工有限公司 Application of the cyclic silicate ester compounds in battery electrolyte
CN109456235A (en) * 2018-12-17 2019-03-12 苏州华道生物药业股份有限公司 A kind of green synthesis method of benzene sulfonic acid alkynes propyl ester
WO2019095636A1 (en) * 2017-11-14 2019-05-23 石家庄圣泰化工有限公司 Method for synthesizing benzenesulfonate derivative
CN112939820A (en) * 2021-02-26 2021-06-11 石家庄圣泰化工有限公司 Synthetic method of benzene sulfonate derivative
CN114409574A (en) * 2021-12-14 2022-04-29 寿光诺盟化工有限公司 Preparation method of allyl benzenesulfonate

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113851711B (en) * 2020-06-28 2023-06-30 深圳市研一新材料有限责任公司 Battery electrolyte and preparation method of benzenesulfonate compound therein

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102226281A (en) * 2011-06-14 2011-10-26 北京科技大学 Non-aldehyde acidification corrosion inhibitor and preparation method thereof
CN103936789A (en) * 2014-04-25 2014-07-23 上海交通大学 Quaternary phosphonium sulfonate fire retardant and synthesis method and use thereof

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS59122455A (en) * 1982-12-29 1984-07-14 Nippon Synthetic Chem Ind Co Ltd:The Preparation of p-toluenesulfonic acid (meth)allyl ester
JPH0336086A (en) * 1989-07-04 1991-02-15 Nippon Kayaku Co Ltd Thermal recording material
US5340489A (en) * 1992-06-05 1994-08-23 The Dow Chemical Company Aryl arenesulfonates and a method of lubrication using the aryl arenesulfonates
US5284944A (en) * 1992-06-30 1994-02-08 Lever Brothers Company, Division Of Conopco, Inc. Improved synthesis of 1,4,7-triazacyclononane
EP1138669A4 (en) 1998-11-13 2002-01-23 Mitsui Chemicals Inc Benzenesulfonic acid derivative compounds, process for producing the same, and use thereof
JP3445515B2 (en) * 1999-01-29 2003-09-08 陽 田辺 Method for sulfonylation of alcohol
JP5125379B2 (en) * 2007-10-04 2013-01-23 宇部興産株式会社 Electrolytic solution for lithium secondary battery containing benzenesulfonic acid ester, and lithium secondary battery using the same
JP2011238373A (en) * 2010-05-06 2011-11-24 Sony Corp Secondary battery, electrolytic solution for secondary battery, electric tool, electric vehicle, and power storage system
CN106588705B (en) * 2016-12-11 2018-02-27 盐城市胜达化工有限公司 A kind of technique by nano solid base catalyst synthesizing glycol DAADBSA ester
CN106631911A (en) * 2016-12-25 2017-05-10 西北大学 Method for synthesizing cis-tritosylate
CN107840812A (en) * 2017-11-14 2018-03-27 石家庄圣泰化工有限公司 The synthetic method of tosylate derivative

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102226281A (en) * 2011-06-14 2011-10-26 北京科技大学 Non-aldehyde acidification corrosion inhibitor and preparation method thereof
CN103936789A (en) * 2014-04-25 2014-07-23 上海交通大学 Quaternary phosphonium sulfonate fire retardant and synthesis method and use thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
刘淑芬等: "聚合物假冠醚研究（I）单体乙二醇二苯醚的合成与表征", 《离子交换与吸附》 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019095636A1 (en) * 2017-11-14 2019-05-23 石家庄圣泰化工有限公司 Method for synthesizing benzenesulfonate derivative
KR20190105493A (en) * 2017-11-14 2019-09-17 스자좡 에스에이엔 타이 케미컬 컴퍼니 리미티드 A method for synthesis of benzene sulfonate derivatives
KR102144626B1 (en) 2017-11-14 2020-08-28 스자좡 에스에이엔 타이 케미컬 컴퍼니 리미티드 A method for synthesis of benzene sulfonate derivatives
CN109004279A (en) * 2018-07-18 2018-12-14 石家庄圣泰化工有限公司 Application of the cyclic silicate ester compounds in battery electrolyte
CN109456235A (en) * 2018-12-17 2019-03-12 苏州华道生物药业股份有限公司 A kind of green synthesis method of benzene sulfonic acid alkynes propyl ester
CN112939820A (en) * 2021-02-26 2021-06-11 石家庄圣泰化工有限公司 Synthetic method of benzene sulfonate derivative
CN114409574A (en) * 2021-12-14 2022-04-29 寿光诺盟化工有限公司 Preparation method of allyl benzenesulfonate

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Application publication date: 20180327