CN114349734A - Preparation method of electrolyte additive of 2, 2-difluoro-1, 3-propyl sulfinic acid lactone and derivatives thereof - Google Patents

Preparation method of electrolyte additive of 2, 2-difluoro-1, 3-propyl sulfinic acid lactone and derivatives thereof Download PDF

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CN114349734A
CN114349734A CN202210088041.5A CN202210088041A CN114349734A CN 114349734 A CN114349734 A CN 114349734A CN 202210088041 A CN202210088041 A CN 202210088041A CN 114349734 A CN114349734 A CN 114349734A
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difluoro
derivative
solvent
electrolyte additive
sulfinic acid
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吴红松
邵永亮
贾晓旭
齐贺军
李江潮
贾晓茹
郅雅琴
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Hebei Songchen Pharmaceutical Technology Co ltd
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    • 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
    • C07D327/10—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms two oxygen atoms and one sulfur atom, e.g. cyclic sulfates
    • 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
    • H01M10/052—Li-accumulators
    • H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
    • 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

Abstract

The invention relates to a preparation method of an electrolyte additive of 2, 2-difluoro-1, 3-propyl sulfinic acid lactone and derivatives thereof, under the protection of nitrogen, adding a solvent and a compound A2, 2-difluoro-1, 3-propanediol or derivatives thereof into a dry and anhydrous reactor, adding a cyclization agent in batches at room temperature, heating the mixture to 20-80 ℃, refluxing and preserving heat for reaction for 2-4h, and confirming the reaction completion by a thin layer chromatography; then washing and concentrating to obtain the product. Compared with the common battery electrolyte additive, the additive has the advantages of improving the voltage and ionic conductivity of the battery and improving the low-temperature performance of the battery.

Description

Preparation method of electrolyte additive of 2, 2-difluoro-1, 3-propyl sulfinic acid lactone and derivatives thereof
Technical Field
The invention relates to the technical field of battery electrolyte, in particular to an electrolyte additive of 2, 2-difluoro-1, 3-propyl sulfinic acid lactone and derivatives thereof and a synthetic method thereof.
Background
With the improvement of environmental awareness of people, the trend of social development is that clean energy replaces fossil energy, and electric vehicles and hybrid vehicles are widely concerned by research and development personnel. The lithium battery has the advantages of high energy density, high voltage, multiple cycle times, long storage time and the like, and is widely applied to various aspects such as electric automobiles, energy storage power stations, unmanned aerial vehicles, portable equipment and the like.
The electrolyte solution receives increasing attention as one of the most important raw materials of the lithium ion battery, and its main research is focused on the use of various additives. A small amount of certain substances are added into the electrolyte, so that the conductivity, the anode and cathode matching performance, the battery capacity, the cycle life, the reversible capacity and the safety performance of the electrolyte with certain performances of the battery can be obviously improved.
German patent DE19829030C1 proposes compounds containing lithium as starting material, such as LiOH or Li2CO3A method for preparing LiBOB from oxalic acid or oxalate, boric acid or boron oxide. The preparation method is simple and feasible, and the raw materials are cheap and easy to obtain. However, since the whole reaction process is accompanied by the existence of a large amount of water, and the water has great negative influence on the LiBOB used as the electrolyte of the lithium ion battery, how to ensure that the product is anhydrous becomes the key for preparing the LiBOB by the method. In addition, the LiBOB product prepared by the method easily contains unreacted raw material substances such as oxalic acid and the like, and the product purity is low.
Chinese patent CN109776487A discloses a method for synthesizing an additive for lithium batteries, but in this application, hydrogen chloride gas is generated during the reaction process, and although water is used for absorption, the problem of pollution still cannot be avoided.
Disclosure of Invention
The invention aims to provide an electrolyte additive for improving the voltage and the ionic conductivity of a battery and improving the low-temperature performance of the battery, namely 2, 2-difluoro-1, 3-propyl sulfinic acid lactone and derivatives thereof, and a synthesis method thereof.
The technical scheme of the invention is as follows:
a synthetic method of an electrolyte additive of 2, 2-difluoro-1, 3-propyl sulfinic acid lactone and derivatives thereof comprises the following chemical reaction formula:
Figure BDA0003487929740000021
the chemical reaction formula of the derivative is as follows:
Figure BDA0003487929740000022
wherein R is1And R2Each independently is hydrogen, halogen, C1-3Alkyl radical, C1-3Haloalkyl, cyano, C3-6Cycloalkyl or C3-6Spirocycloalkyl, wherein n is an integer of 2 or 3, and includes stereoisomers thereof.
Preferably, the method comprises the following steps:
(1) adding a solvent and a compound A2, 2-difluoro-1, 3-propanediol or a derivative thereof into a dry anhydrous reactor under the protection of nitrogen, adding a cyclization agent in batches at room temperature, heating the mixture to 20-80 ℃, refluxing and preserving heat for reaction for 2-4h, and confirming the completion of the reaction by thin chromatography;
(2) cooling to 5 ℃, and adding a quenching agent into the system to quench the reaction;
(3) separating liquid, extracting the water phase with organic solvent until no product is produced, combining the organic phases, washing with water, washing with saturated sodium chloride solution once, drying with anhydrous sodium sulfate, filtering, and concentrating the filtrate under reduced pressure until no solvent is produced to obtain a crude product.
Preferably, the molar ratio of the starting material A2, 2-difluoro-1, 3-propanediol or the starting material I to the cyclizing agent in the reaction of step (1) is 1:0.9 to 1: 2.0; the batch is not less than 2 batches.
The molar ratio of the starting material A2, 2-difluoro-1, 3-propanediol or the starting material I to the solvent is from 1:10 to 1: 18.
Preferably, the cyclization reagent in step (1) is N, N' -thionyl diimidazole.
Preferably, the volume ratio of the quenching agent in the step (2) to the solvent added in the step (1) is as follows: 1:1.5-1:3.
Preferably, the quenching agent is cold water, an ammonium chloride aqueous solution or a dilute acid solution, the water temperature of the cold water is less than 10 ℃, the mass fraction of the ammonium chloride aqueous solution is 5-40%, the dilute acid solution is dilute sulfuric acid or dilute hydrochloric acid, and the mass fraction of the dilute sulfuric acid or dilute hydrochloric acid is 5-35%.
Preferably, the solvent used in step (1) and step (3) is a non-polar solvent comprising: one or more of dichloromethane, dichloroethane, pentane, hexane, cyclohexane, benzene, toluene, xylene, 1, 4-dioxane, chloroform, diethyl ether and methyl tert-butyl ether are combined, and the solvents used in the step (1) and the step (3) are the same in type.
Preferably, the crude product in the step (3) is pulped by n-hexane and filtered to obtain a pure product of 2, 2-difluoro-1, 3-propyl sulfinic acid lactone or a derivative thereof, wherein the mass ratio of the n-hexane to the crude product is 2:1-4: 1.
The room temperature described herein is 10-28 ℃.
The invention has the beneficial effects that:
the invention improves the voltage and ionic conductivity of the battery and improves the low-temperature performance of the battery; the method has the advantages of less three wastes, environmental protection, continuous production and industrialized synthesis.
In the aspect of synthesis route, the invention adopts the traditional easily available raw materials, reduces the production cost, avoids high-risk reactions such as fluorination and the like, reduces the quantity of three wastes, and has green and friendly product route.
3, the cyclization reagent adopted by the method is N, N' -thionyl diimidazole, and compared with thionyl chloride used traditionally, the method is safer, more green, free of stimulation, higher in conversion efficiency and easier in industrial production.
Detailed Description
Example 1
Figure BDA0003487929740000041
Preparation of DFTSI: adding 3.6L of dichloroethane, 400g of compound A (2, 2-difluoro-1, 3-propanediol), 3.57mol of N, N' -thionyldiimidazole 715.3g and 3.925mol into a dry and anhydrous 10L reaction bottle under the protection of nitrogen in batches at room temperature of 20 ℃, heating the mixture to 55-60 ℃, keeping the temperature for reaction for 4h, confirming the reaction is complete by TLC, cooling to 5 ℃, adding 2L of 2mol/L HCl aqueous solution into the system, quenching the reaction, separating the liquid, extracting the aqueous phase by dichloroethane until no product is produced (2 times multiplied by 500ml), combining the organic phases, washing the organic phases by 1 time multiplied by 500ml by saturated sodium chloride solution once multiplied by 500ml, drying anhydrous sodium sulfate, carrying out suction filtration, concentrating the filtrate under reduced pressure (the vacuum degree of-0.098 MPa) until no solvent is produced to obtain a crude product, carrying out suction filtration by normal hexane to obtain a pure product DFTSI 472g as a white solid, yield 76%, GC: 99.6%, 1HNMR (500MHz, CDCl)3)δ:4.773-4.862(m,2H)，4.053-4.101(m,2H),m/z＝157.98。
Test number A SIDI(eq.) Temperature of Solvent(s) Yield of
Comparative example 1 50g 1.1 20-60℃ Dichloroethane 75.2％
Comparative example 2 2000g 1.1 20-60℃ Dichloroethane 78％
Note: "a" means 2, 2-difluoro-1, 3-propanediol, "SIDI" means N, N' -thionyldiimidazole, "eq." means molar equivalent ratio to 1mol of 2, 2-difluoro-1, 3-propanediol, "temperature" means reaction temperature, "solvent" means nonpolar solvent for the reaction, "yield" means molar yield calculated from the product of the reaction.
Comparative examples 1-2 in the above table are comparative tests to example 1, and the conditions were the same as in example 1 except that the amount of 2, 2-difluoro-1, 3-propanediol was varied, and it can be seen from the table that the yield gradually increased with the increase in the amount of 2, 2-difluoro-1, 3-propanediol and was at most 78% when the amount of 2, 2-difluoro-1, 3-propanediol was 2000 g.
Example 2
Figure BDA0003487929740000051
Preparation of DFTSI: under the protection of nitrogen, adding 90mL of dichloroethane, 10g and 89.2mmol of compound A (2, 2-difluoro-1, 3-propanediol), 17.88g and 98.1mmol of N, N' -sulfinyl diimidazole at room temperature of 20 ℃ in batches into a dry and anhydrous 250mL reaction bottle, heating the mixture to 55-60 ℃, keeping the temperature for reaction for 4 hours, confirming the reaction is complete by TLC, cooling to 5 ℃, adding 50mL of water into the system, quenching the reaction, separating liquid, extracting the aqueous phase with dichloroethane until no product is produced (2 times by 30mL), combining the organic phase, washing with 1 time by 30mL of water, saturating with 1 time by 30mL of saturated sodium chloride, and anhydrous sulfuric acidSodium drying, suction filtering, concentrating the filtrate under reduced pressure (vacuum degree-0.098 MPa) until no solvent is available to obtain crude product, pulping with n-hexane, suction filtering to obtain pure product DFTSI 10.5g as white solid with yield of 74.4%, GC: 99.0%, 1HNMR (500MHz, CDCl)3)δ:4.773-4.862(m,2H)，4.053-4.101(m,2H),m/z＝157.98。
Test number A SIDI(eq.) Temperature of Solvent(s) Yield of
Comparative example 3 10g 1.0 20-60℃ Dichloroethane 70.5％
Comparative example 4 10g 1.5 20-60℃ Dichloroethane 75％
Comparative example 5 10g 2.0 20-60℃ Dichloroethane 73％
Note: "a" means 2, 2-difluoro-1, 3-propanediol, "SIDI" means N, N' -thionyldiimidazole, "eq." means molar equivalent ratio to 1mol of 2, 2-difluoro-1, 3-propanediol, "temperature" means reaction temperature, "solvent" means nonpolar solvent for the reaction, "yield" means molar yield calculated from the product of the reaction.
Comparative examples 3 to 5 in the above table are comparative tests for example 2, and the conditions are the same as in example 2 except that the amount of the cyclizing agent is different, and we can see that the yield is increased and then decreased with the increase of the cyclizing agent N, N '-thionyldiimidazole, and that the yield is 75% at the maximum when the molar ratio of N, N' -thionyldiimidazole to 2, 2-difluoro-1, 3-propanediol is 1.5.
Example 3
Figure BDA0003487929740000061
Preparation of DFTSI: adding 90mL of 1, 4-dioxane, 10g of compound A (2, 2-difluoro-1, 3-propanediol) and 89.2mmol into a dry and anhydrous 250mL reaction bottle under the protection of nitrogen, adding 17.88g of N, N' -thionyl diimidazole and 98.1mmol in batches at room temperature of 20 ℃, heating the mixture to 80 ℃, keeping the temperature for reaction for 4 hours, confirming the reaction is complete through TLC, cooling to 5 ℃, adding 50mL of 4mol/L ammonium chloride aqueous solution into the system, quenching, separating liquid, extracting an aqueous phase by dichloroethane until no product (2 times multiplied by 30mL) exists, combining the organic phases, washing 1 time multiplied by 30mL by water, washing 1 time multiplied by 30mL by saturated sodium chloride solution, drying anhydrous sodium sulfate, carrying out suction filtration, concentrating a filtrate under reduced vacuum degree (vacuum degree-0.098 MPa) until no solvent exists to obtain a crude product, carrying out suction filtration by using N-hexane to obtain 9.4g of pure TSDFI as a white solid, yield 67%, GC: 99.0 percent.
Test number A SIDI(eq.) Temperature of Solvent(s) Yield of
Comparative example 6 10g 1.1 20-40℃ Methylene dichloride 62％
Comparative example 7 10g 1.1 20-80℃ Toluene 65％
Comparative example 8 10g 1.1 20-30℃ Ether (A) 61％
Note: "a" means 2, 2-difluoro-1, 3-propanediol, "SIDI" means N, N' -thionyldiimidazole, "eq." means molar equivalent ratio to 1mol of 2, 2-difluoro-1, 3-propanediol, "temperature" means reaction temperature, "solvent" means nonpolar solvent for the reaction, "yield" means molar yield calculated from the product of the reaction.
In the above table, comparative examples 6 to 8 are comparative tests on example 3, and different from example 3, the reaction temperature and the solvent are set according to the boiling point of the solvent, and it can be seen from the table that the yield is not much different when dichloromethane, toluene and diethyl ether are selected as the solvent, while the yield of 1, 4-dioxane is 67% at most selected as the solvent in example 3.
Example 4
Figure BDA0003487929740000071
Preparation of DFTSI: adding 250mL of N-hexane, 10g and 89.2mmol of compound A (2, 2-difluoro-1, 3-propanediol), 17.88g and 98.1mmol of N, N' -sulfinyldiimidazole into a dry and anhydrous 500mL reaction bottle under the protection of nitrogen in batches at room temperature of 20 ℃, heating the mixture to 70 ℃, keeping the temperature for reaction for 8h, confirming the reaction is complete through TLC, cooling to 5 ℃, adding 50mL of 2mol/L HCl aqueous solution into the system, quenching, separating, extracting an aqueous phase with dichloroethane until no product (2 times by 30mL), washing combined organic phases with 1 time by 30mL of water, washing with saturated sodium chloride solution for 1 time by 30mL, drying with anhydrous sodium sulfate, carrying out suction filtration, concentrating a filtrate under reduced pressure (vacuum degree-0.098 MPa) until no solvent is obtained to obtain a crude product, pulping and carrying out suction filtration with N-hexane to obtain 6.63g of pure TSDFI as a white solid with the yield of 47%, GC: 99.0 percent.
Example 5
Figure BDA0003487929740000072
Preparation of DFTSI derivatives: in thatUnder the protection of nitrogen, 90mL of chloroform and 10.4g and 100mmol of compound A (2, 2-dimethyl-1, 3-propanediol) are added into a dry and anhydrous 250mL reaction bottle, 17.88g and 98.1mmol of N, N' -sulfinyl diimidazole are added in batches at room temperature of 20 ℃, the mixture is heated to 55-60 ℃ and is kept for reaction for 4 hours, the reaction is confirmed to be complete by TLC, the temperature is reduced to 5 ℃, and 2mol/LH is added into the system2SO4Quenching reaction of 50mL of aqueous solution, separating liquid, extracting an aqueous phase by dichloroethane until no product is produced (2 times multiplied by 30mL), combining organic phases, washing by water for 1 time multiplied by 30mL, washing by saturated sodium chloride solution for one time, drying by anhydrous sodium sulfate, filtering, concentrating a filtrate under reduced pressure (vacuum degree-0.098 MPa) until no solvent is produced to obtain a crude product, pulping by normal hexane, filtering to obtain 10.74g of a pure DFTSI derivative as a white solid, wherein the yield is 71.6%, and GC: 99.2 percent.
Example 6
Figure BDA0003487929740000081
Preparation of DFTSI derivatives: under the protection of nitrogen, adding 90mL of dichloroethane, 11.05g and 100mmol of compound A (2-chloro-1, 3-propanediol), adding 17.88g and 98.1mmol of N, N' -thionyl diimidazole in batches at room temperature of 20 ℃, heating the mixture to 55-60 ℃, keeping the temperature for reaction for 4 hours, confirming the reaction is complete by TLC, cooling to 5 ℃, adding 50mL of 4mol/L ammonium chloride aqueous solution into the system, quenching, separating, extracting an aqueous phase by dichloroethane until no product (2 times by 30mL) exists, combining an organic phase, washing 1 time by 30mL by water, washing 1 time by 30mL by saturated sodium chloride solution, drying by anhydrous sodium sulfate, carrying out suction filtration, concentrating a filtrate under reduced pressure (vacuum degree of-0.098 MPa) until no solvent exists, obtaining a crude product, carrying out suction filtration by normal hexane to obtain 10.64g of a pure DFTSI derivative as a white solid, yield 68%, GC: 99.5 percent.
Although the present invention has been described with reference to the preferred embodiments, it should be understood that various changes, substitutions and alterations can be made herein without departing from the spirit and scope of the invention as defined by the appended claims.

Claims (8)

1. A synthetic method of an electrolyte additive of 2, 2-difluoro-1, 3-propyl sulfinic acid lactone and derivatives thereof is characterized in that the chemical reaction formula is as follows:
Figure FDA0003487929730000011
the chemical reaction formula of the derivative is as follows:
Figure FDA0003487929730000012
wherein R is1And R2Each independently is hydrogen, halogen, C1-3Alkyl radical, C1-3Haloalkyl, cyano, C3-6Cycloalkyl or C3-6Spirocycloalkyl, wherein n is an integer of 2 or 3, and includes stereoisomers thereof.
2. The method for synthesizing the electrolyte additive of 2, 2-difluoro-1, 3-propyl sulfinic acid lactone and the derivative thereof according to claim 1, is characterized by comprising the following steps:
(1) adding a solvent and a compound A2, 2-difluoro-1, 3-propanediol or a derivative thereof into a dry anhydrous reactor under the protection of nitrogen, adding a cyclization agent in batches at room temperature, heating the mixture to 20-80 ℃, refluxing and preserving heat for reaction for 2-4h, and confirming the completion of the reaction by thin chromatography;
(2) cooling to 5 ℃, and adding a quenching agent into the system to quench the reaction;
(3) separating liquid, extracting the water phase with organic solvent until no product is produced, combining the organic phases, washing with water, washing with saturated sodium chloride solution once, drying with anhydrous sodium sulfate, filtering, and concentrating the filtrate under reduced pressure until no solvent is produced to obtain a crude product.
3. The method for synthesizing the electrolyte additive of 2, 2-difluoro-1, 3-propyl sulfinic acid lactone and the derivative thereof according to claim 2, characterized in that in the step (1), the molar ratio of the starting material A2, 2-difluoro-1, 3-propanediol or the starting material I to the cyclizing agent is 1:0.9-1: 2.0; the batches are not less than 2 batches;
the molar ratio of the starting material A2, 2-difluoro-1, 3-propanediol or starting material I to the solvent is from 1:10 to 1: 18.
4. The method for synthesizing the electrolyte additive of 2, 2-difluoro-1, 3-propyl sulfinic acid lactone and the derivative thereof according to claim 2, wherein the cyclizing reagent in the step (1) is N, N' -sulfinyl diimidazole.
5. The method for synthesizing the electrolyte additive of 2, 2-difluoro-1, 3-propyl sulfinic acid lactone and the derivative thereof according to claim 2, wherein the volume ratio of the quenching agent in the step (2) to the solvent added in the step (1) is as follows: 1:1.5-1:3.
6. The method for synthesizing the electrolyte additive of 2, 2-difluoro-1, 3-propyl sulfinic acid lactone and the derivative thereof according to claim 2, wherein the quenching agent is cold water, an aqueous ammonium chloride solution or a dilute acid solution, the water temperature of the cold water is less than 10 ℃, the mass fraction of the aqueous ammonium chloride solution is 5-40%, the dilute acid solution is dilute sulfuric acid or dilute hydrochloric acid, and the mass fraction of the dilute sulfuric acid or dilute hydrochloric acid is 5-35%.
7. The method for synthesizing the electrolyte additive of 2, 2-difluoro-1, 3-propyl sulfinic acid lactone and the derivative thereof according to claim 2, wherein the solvent used in the step (1) and the step (3) is a non-polar solvent, and comprises the following steps: one or more of dichloromethane, dichloroethane, pentane, hexane, cyclohexane, benzene, toluene, xylene, 1, 4-dioxane, chloroform, diethyl ether and methyl tert-butyl ether are combined, and the solvents used in the step (1) and the step (3) are the same in type.
8. The method for synthesizing the electrolyte additive of 2, 2-difluoro-1, 3-propyl sulfinic acid lactone and the derivative thereof according to claim 2, wherein the crude product in the step (3) is pulped by n-hexane and filtered to obtain a pure product of 2, 2-difluoro-1, 3-propyl sulfinic acid lactone or the derivative thereof, and the mass ratio of the n-hexane to the crude product is 2:1-4: 1.
CN202210088041.5A 2022-01-25 2022-01-25 Preparation method of electrolyte additive of 2, 2-difluoro-1, 3-propyl sulfinic acid lactone and derivatives thereof Pending CN114349734A (en)

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