WO2018086379A1 - 氰基乙烯基类磺酸酯及其合成方法 - Google Patents

氰基乙烯基类磺酸酯及其合成方法 Download PDF

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WO2018086379A1
WO2018086379A1 PCT/CN2017/093747 CN2017093747W WO2018086379A1 WO 2018086379 A1 WO2018086379 A1 WO 2018086379A1 CN 2017093747 W CN2017093747 W CN 2017093747W WO 2018086379 A1 WO2018086379 A1 WO 2018086379A1
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cyanovinyl
sulfonate
synthesizing
substituted
sulfonate according
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冯俊敏
付成华
张昌明
周艳
陈培培
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宁德时代新能源科技股份有限公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • 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
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • 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
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C07C309/66—Methanesulfonates
    • 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
    • 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

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  • the invention relates to the field of chemical synthesis, in particular to a cyanovinyl sulfonate and a synthesis method thereof.
  • Sulfonate compounds have a wide range of applications and have high industrial application value.
  • it can be used as a drug treatment reagent; in addition, the sulfonate can also be used as a lithium ion battery electrolyte additive to improve the cycle life of the lithium ion battery.
  • sulfonate compounds are currently used as electrolyte additives to improve the cycle performance of lithium ion batteries.
  • Japanese Patent Application No. 2001-313071A published on Nov. 9, 2001, discloses the addition of a sulfonate compound such as 1,4-butanediol dimesylate or propylene glycol dimesylate to an electrolyte
  • Japanese Patent Application No. 09-245834 published on Sep. 19, 1997, discloses the addition of an alkyl alkanesulfonate to an electrolyte, but the above patents all deteriorate the storage properties of a lithium ion battery.
  • the present application introduces a novel functional group on a common sulfonate structural framework to obtain a cyanovinyl sulfonate, which is expected to solve this problem.
  • an object of the present invention is to provide a cyanovinyl sulfonate and a synthesis method thereof, wherein the cyanovinyl sulfonate is synthesized at a relatively fast speed and is easy to carry out, and the reaction is produced.
  • the rate can reach 70% to 80%.
  • the present invention provides a cyanovinyl sulfonate having the following structural formula:
  • R is selected from substituted or unsubstituted alkyl, substituted or unsubstituted carbon having from 1 to 12 carbon atoms An alkoxy group having 1 to 12 atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; and a substituent selected from one or more of halogens.
  • the invention provides a method for synthesizing a cyanovinyl sulfonate for synthesizing a cyanovinyl sulfonate according to one aspect of the invention, comprising the steps of: (1) The ring-opening of the isoxazole in an alkaline solution to form 2-acrylonitrile-1-alkoxide; (2) mixing R-SO 3 Cl with 2-acrylonitrile-1-alkoxide under anhydrous conditions The reaction gave cyanovinylsulfonate.
  • the synthesis rate of the cyanovinyl sulfonate of the present invention is fast and easy to carry out, and the reaction yield can reach 70% to 80%.
  • Example 1 is a nuclear magnetic resonance spectrum of cyanovinyl methanesulfonate obtained in Example 1;
  • Example 2 is a nuclear magnetic resonance carbon spectrum of the cyanovinyl methanesulfonate obtained in Example 1;
  • Example 3 is a mass spectrum of the cyanovinyl methanesulfonate obtained in Example 1.
  • the structural formula of the cyanovinyl sulfonate is:
  • R is selected from a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 12 carbon atoms, and a substituted or unsubstituted carbon number of 6 to 10;
  • One of the aryl groups; the substituent is selected from one or more of the halogens.
  • substituted means substituted or wholly substituted by one or more of the halogens.
  • the substituent is selected from one or both of F and Cl.
  • the number of carbon atoms is
  • the alkyl group of 1 to 12 may be a linear alkyl group or a branched alkyl group.
  • the alkoxy group having 1 to 12 carbon atoms is a linear alkoxy group, and may be a branched alkoxy group.
  • the aryl group having 6 to 10 carbon atoms may be a phenyl group, a phenylalkyl group or an alkylphenyl group.
  • the aryl group having a carbon number of 6 to 10 may be selected from one of a phenyl group, a benzyl group, a p-tolyl group, an o-tolyl group, and an m-tolyl group.
  • R is selected from the group consisting of methyl, ethyl, propyl, phenyl, preferably R is selected from methyl.
  • a method for synthesizing a cyanovinyl sulfonate according to the second aspect of the present invention for synthesizing the cyanovinyl sulfonate according to the first aspect of the present invention comprising the steps of: (1) making isoxazole at Ring-opening to form 2-acrylonitrile-1-alkoxide in an alkaline solution; (2) mixing R-SO 3 Cl with 2-acrylonitrile-1-alkoxide and reacting under anhydrous conditions to obtain cyanoethylene Base sulfonate.
  • R-SO 3 Cl represents an alkylsulfonyl chloride
  • R is selected from a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 12 carbon atoms, and a substitution.
  • one of the unsubstituted aryl groups having 6 to 10 carbon atoms, and the substituent is one or more selected from the group consisting of halogens.
  • the substituent is selected from one or both of F and Cl.
  • the structural formula of alkylsulfonyl chloride is as follows:
  • the cyanovinyl sulfonate cannot be produced by direct esterification reaction of a sulfonic acid with an alcohol, but an alkyl acyl chloride and an alcohol are used.
  • the salt is reacted to obtain a cyanovinyl sulfonate.
  • the superior reactivity of the alkoxide and the good leaving ability of the chlorine group in the alkyl acid chloride make the reaction easier and the yield is higher.
  • the method for synthesizing the cyanovinyl sulfonate of the invention is easy to obtain, low in cost, and easy to realize industrial production.
  • the alkaline solution is one of a sodium methoxide solution and a sodium ethoxide solution.
  • the reaction temperature is -20 ° C to 20 ° C.
  • the isoxazole is added to an alkaline solution, and the progress of the reaction is detected by a TLC thin layer chromatography silica gel plate. After the isoxazole reaction is completed, the solvent in the reaction system is removed by a rotary evaporator under vacuum. It was then dried under vacuum to give 2-acrylonitrile-1-alkoxide.
  • the reaction temperature is -20 ° C to 20 ° C.
  • the molar ratio of R-SO 3 Cl to 2-acrylonitrile-1-alkoxide is (0.1 ⁇ 10): 1.
  • step (2) R-SO 3 Cl and 2-acrylonitrile-1-alkoxide are in anhydrous tetrahydrofuran,
  • the reaction is carried out in water toluene, anhydrous diethyl ether or anhydrous tert-butyl methyl ether.
  • step (2) after the reaction of R-SO 3 Cl with the 2-acrylonitrile-1-alkoxide, suction filtration is employed. The filtrate was taken out, and then distilled under reduced pressure to obtain a cyanovinylsulfonate.
  • the synthesis process of the cyanovinyl sulfonate is carried out under the protection of an inert gas.
  • the inert gas may be nitrogen or argon.
  • the synthesis speed of the cyanovinyl sulfonate is fast and easy to carry out, and the entire synthesis process takes no more than 6 hours.
  • the reaction yield of the cyanovinyl sulfonate is from 70% to 80%.
  • the sodium 2-acrylonitrile-1-ol was dissolved in 50 mL of anhydrous dry tetrahydrofuran, and the reaction system was cooled to 0 ° C, and 5.7 g of methylsulfonyl chloride was slowly added dropwise to the reaction system, and the reaction was continued after the completion of the dropwise addition. One hour.
  • the reaction liquid was suction filtered to give a colorless filtrate, which was evaporated under reduced pressure to give 5.15 g of colorless cyanovinyl methanesulfonate.
  • FIG. 1 is a nuclear magnetic resonance spectrum of the cyanovinyl methanesulfonate obtained in Example 1;
  • FIG. 2 is a nuclear magnetic resonance spectrum of the cyanovinyl methanesulfonate obtained in Example 1;
  • 3 is a mass spectrum of the cyanovinyl methanesulfonate obtained in Example 1.

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Electrochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

一种氰基乙烯基类磺酸酯及其合成方法。所述氰基乙烯基类磺酸酯的结构式如(I)。其中，R选自取代或未取代的碳原子数为1～12的烷基、取代或未取代的碳原子数为1～12的烷氧基、取代或未取代的碳原子数为6～10的芳基中的一种；取代基选自卤素中的一种或几种。氰基乙烯基类磺酸酯的合成速度较快且容易实行，反应产率可达到70％～80％。

Description

氰基乙烯基类磺酸酯及其合成方法 技术领域
本发明涉及化学合成领域，具体涉及一种氰基乙烯基类磺酸酯及其合成方法。
背景技术
磺酸酯化合物具有广泛的应用，有很高的工业应用价值。比如可作为药物治疗试剂使用；另外磺酸酯还能作为锂离子电池电解液添加剂使用，提高锂离子电池的循环寿命。
当前许多磺酸酯化合物作为电解液添加剂以改善锂离子电池的循环性能。例如，2001年11月9日公开的日本专利申请JP2001-313071A公开了在电解液中添加磺酸酯化合物如1,4-丁二醇二甲磺酸酯或丙二醇二甲磺酸酯；又如，1997年9月19日公开的日本专利申请JP09-245834公开了在电解液中加入烷磺酸烷基酯，但是上述专利均会恶化锂离子电池的存储等性能。本申请在普通磺酸酯结构框架上引入新的官能团得到氰基乙烯基类磺酸酯，从而有望解决这一问题。
发明内容
鉴于背景技术中存在的问题，本发明的目的在于提供一种氰基乙烯基类磺酸酯及其合成方法，所述氰基乙烯基类磺酸酯的合成速度较快且容易实行，反应产率可达到70％～80％。
为了达到上述目的，在本发明的一方面，本发明提供了一种氰基乙烯基类磺酸酯，所述氰基乙烯基类磺酸酯的结构式如下：
Figure PCTCN2017093747-appb-000001
其中，R选自取代或未取代的碳原子数为1～12的烷基、取代或未取代的碳 原子数为1～12的烷氧基、取代或未取代的碳原子数为6～10的芳基中的一种；取代基选自卤素中的一种或几种。
在本发明的另一方面，本发明提供了一种氰基乙烯基类磺酸酯的合成方法，用于合成本发明一方面所述的氰基乙烯基类磺酸酯，包括步骤：(1)使异恶唑在碱性溶液环境下开环生成2-丙烯腈-1-醇盐；(2)将R-SO3Cl与2-丙烯腈-1-醇盐混合，在无水条件下反应，得到氰基乙烯基磺酸酯。
相对于现有技术，本发明的有益效果为：
本发明的氰基乙烯基类磺酸酯的合成速度较快且容易实行，反应产率可达到70％～80％。
附图说明
图1是实施例1中得到的氰基乙烯基甲磺酸酯的核磁共振氢谱图；
图2是实施例1中得到的氰基乙烯基甲磺酸酯的核磁共振碳谱图；
图3是实施例1中得到的氰基乙烯基甲磺酸酯的质谱图。
具体实施方式
下面详细说明根据本发明的氰基乙烯基类磺酸酯及其合成方法。
首先说明根据本发明第一方面的氰基乙烯基类磺酸酯。
根据本发明第一方面的氰基乙烯基类磺酸酯，所述氰基乙烯基类磺酸酯的结构式为：
Figure PCTCN2017093747-appb-000002
其中，R选自取代或未取代的碳原子数为1～12的烷基、取代或未取代的碳原子数为1～12的烷氧基、取代或未取代的碳原子数为6～10的芳基中的一种；取代基选自卤素中的一种或几种。其中，“取代”表示被卤素中的一种或几种部分取代或全部取代。优选地，所述取代基选自F、Cl中的一种或两种。
在根据本发明第一方面所述的氰基乙烯基类磺酸酯中，所述碳原子数为 1～12的烷基可为直链烷基，也可为支链烷基。所述碳原子数为1～12的烷氧基为直链烷氧基，也可为支链烷氧基。所述碳原子数为6～10的芳基可为苯基、苯基烷基、烷基苯基。具体地，所述碳原子数可选自6～10的芳基选自苯基、苄基、对甲苯基、邻甲苯基、间甲苯基中的一种。
在根据本发明第一方面所述的氰基乙烯基类磺酸酯中，R选自甲基、乙基、丙基、苯基，优选地，R选自甲基。
其次说明根据本发明第二方面的氰基乙烯基类磺酸酯的合成方法。
根据本发明第二方面的氰基乙烯基类磺酸酯的合成方法，用于合成本发明第一方面所述的氰基乙烯基类磺酸酯，包括步骤：(1)使异恶唑在碱性溶液环境下开环生成2-丙烯腈-1-醇盐；(2)将R-SO3Cl与2-丙烯腈-1-醇盐混合，在无水条件下反应，得到氰基乙烯基类磺酸酯。
其中，R-SO3Cl表示烷基磺酰氯，R选自取代或未取代的碳原子数为1～12的烷基、取代或未取代的碳原子数为1～12的烷氧基、取代或未取代的碳原子数为6～10的芳基中的一种，取代基选自卤素中的一种或几种。优选地，所述取代基选自F、Cl中的一种或两种。烷基磺酰氯的结构式如下：
Figure PCTCN2017093747-appb-000003
在根据本发明第二方面的氰基乙烯基类磺酸酯的合成方法中，氰基乙烯基类磺酸酯无法通过磺酸与醇直接酯化反应来制备，而是采用烷基酰氯与醇盐进行反应得到氰基乙烯基类磺酸酯。利用醇盐优异的反应活性及烷基酰氯中氯基团良好的离去能力使得反应更容易进行，产率更高。
本发明的氰基乙烯基类磺酸酯的合成方法原料易得、成本低、易于实现工业化生产。
在根据本发明第二方面的氰基乙烯基类磺酸酯的合成方法中，在步骤(1)中，碱性溶液为甲醇钠溶液、乙醇钠溶液中的一种。
在根据本发明第二方面的氰基乙烯基类磺酸酯的合成方法中，在步骤(1)中，反应温度为﹣20℃～20℃。
在根据本发明第二方面的氰基乙烯基类磺酸酯的合成方法中，在步骤 (1)中，将异恶唑加入到碱性溶液中后通过TLC薄层层析硅胶板检测反应进程，当异恶唑反应完全后，在真空下通过旋转蒸发仪除去反应体系中的溶剂，然后真空干燥得到2-丙烯腈-1-醇盐。
在根据本发明第二方面的氰基乙烯基类磺酸酯的合成方法中，在步骤(2)中，反应温度为﹣20℃～20℃。
在根据本发明第二方面的氰基乙烯基类磺酸酯的合成方法中，在步骤(2)中，R-SO3Cl与2-丙烯腈-1-醇盐的摩尔比为(0.1～10)：1。
在根据本发明第二方面的氰基乙烯基类磺酸酯的合成方法中，在步骤(2)中，将R-SO3Cl与2-丙烯腈-1-醇盐在无水四氢呋喃、无水甲苯、无水乙醚或无水叔丁基甲醚中进行反应。
在根据本发明第二方面的氰基乙烯基类磺酸酯的合成方法中，在步骤(2)中，R-SO3Cl与2-丙烯腈-1-醇盐反应完毕后，采用抽滤的方法取出滤液，之后经减压蒸馏得到氰基乙烯基类磺酸酯。
在根据本发明第二方面的氰基乙烯基类磺酸酯的合成方法中，所述氰基乙烯基类磺酸酯的合成过程在惰性气体保护下进行。优选地，所述惰性气体可为氮气或氩气。
在根据本发明第二方面的氰基乙烯基类磺酸酯的合成方法中，氰基乙烯基类磺酸酯的合成速度较快且容易实行，整个合成过程的时间不超过6小时。
在根据本发明第二方面的氰基乙烯基类磺酸酯的合成方法中，所述氰基乙烯基类磺酸酯的反应产率为70％～80％。
下面结合实施例，进一步阐述本申请。应理解，这些实施例仅用于说明本申请而不用于限制本申请的范围。
实施例1
将3.57g浓度为5M的甲醇钠的甲醇溶液加入干燥且充满氮气保护的反应瓶中，冷却至0℃，加入3.2mL异恶唑(密度为1.055g/ml)，保持0℃搅拌两小时。通过TLC薄层层析硅胶板监测原料已经消失后，在真空下通过旋转蒸发仪除去反应体系中的溶剂，使用真空油泵干燥残余物得到2-丙烯腈-1-醇钠。
将2-丙烯腈-1-醇钠溶于50mL无水干燥的四氢呋喃中，将反应体系降温至0℃，将5.7g的甲基磺酰氯缓慢滴加至反应体系中，滴加完毕后继续反应一小时。将反应液抽滤得到无色滤液，经过减压蒸馏得到5.15g无色的氰基乙烯基甲磺酸酯，其产率为76.9％。
其中，图1是实施例1中得到的氰基乙烯基甲磺酸酯的核磁共振氢谱图；图2是实施例1中得到的氰基乙烯基甲磺酸酯的核磁共振碳谱图；图3是实施例1中得到的氰基乙烯基甲磺酸酯的质谱图。
上述内容为结合具体实施例对本发明做的详细说明，并不局限于这些说明。对本发明所述领域的技术人员基于本发明思路所做的一些修改和变更都应当在本发明的保护范围内。

Claims (10)

  1. 一种氰基乙烯基类磺酸酯，其特征在于，所述氰基乙烯基类磺酸酯的结构式如下：
    Figure PCTCN2017093747-appb-100001
    其中，R选自取代或未取代的碳原子数为1～12的烷基、取代或未取代的碳原子数为1～12的烷氧基、取代或未取代的碳原子数为6～10的芳基中的一种；
    取代基选自卤素中的一种或几种。
  2. 根据权利要求1所述的氰基乙烯基类磺酸酯，其特征在于，所述取代基选自F、Cl中的一种或两种。
  3. 根据权利要求1所述的氰基乙烯基类磺酸酯，其特征在于，R选自甲基、乙基、丙基、苯基，优选地，R选自甲基。
  4. 一种氰基乙烯基类磺酸酯的合成方法，用于合成权利要求1-3中任一项所述的氰基乙烯基类磺酸酯，其特征在于，包括步骤：
    (1)使异恶唑在碱性溶液环境下开环生成2-丙烯腈-1-醇盐；
    (2)将R-SO3Cl与2-丙烯腈-1-醇盐混合，在无水条件下反应，得到氰基乙烯基类磺酸酯。
  5. 根据权利要求4所述的氰基乙烯基类磺酸酯的合成方法，其特征在于，在步骤(1)中，碱性溶液为甲醇钠溶液、乙醇钠溶液中的一种。
  6. 根据权利要求4所述的氰基乙烯基类磺酸酯的合成方法，其特征在于，在步骤(1)中，反应温度为﹣20℃～20℃。
  7. 根据权利要求4所述的氰基乙烯基类磺酸酯的合成方法，其特征在于，在步骤(2)中，反应温度为﹣20℃～20℃。
  8. 根据权利要求4所述的氰基乙烯基类磺酸酯的合成方法，其特征在于，在步骤(2)中，R-SO3Cl与2-丙烯腈-1-醇盐的摩尔比为(0.1～10)：1。
  9. 根据权利要求4所述的氰基乙烯基类磺酸酯的合成方法，其特征在于，在步骤(2)中，将R-SO3Cl与2-丙烯腈-1-醇盐在无水四氢呋喃、无水甲苯、无水乙醚或无水叔丁基甲醚中进行反应。
  10. 根据权利要求4所述的氰基乙烯基类磺酸酯的合成方法，其特征在于，所述氰基乙烯基类磺酸酯的合成在惰性气体保护下进行。
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CN101548426A (zh) * 2006-10-25 2009-09-30 株式会社Lg化学 非水性电解质以及包含该电解质的电化学装置
CN104393242A (zh) * 2007-06-11 2015-03-04 株式会社Lg化学 非水电解质及包含该非水电解质的二次电池
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Publication number Priority date Publication date Assignee Title
JPH09245834A (ja) * 1996-03-13 1997-09-19 Mitsubishi Chem Corp リチウム二次電池用電解液
CN101548426A (zh) * 2006-10-25 2009-09-30 株式会社Lg化学 非水性电解质以及包含该电解质的电化学装置
CN104393242A (zh) * 2007-06-11 2015-03-04 株式会社Lg化学 非水电解质及包含该非水电解质的二次电池
CN105161753A (zh) * 2014-05-26 2015-12-16 宁德时代新能源科技有限公司 锂离子电池及其电解液

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