CN115784945B - 一种双全氟烷基磺酰亚胺盐的制备方法 - Google Patents
一种双全氟烷基磺酰亚胺盐的制备方法 Download PDFInfo
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- CN115784945B CN115784945B CN202211494340.5A CN202211494340A CN115784945B CN 115784945 B CN115784945 B CN 115784945B CN 202211494340 A CN202211494340 A CN 202211494340A CN 115784945 B CN115784945 B CN 115784945B
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- Prior art keywords
- diperoxy
- sulfonyl imide
- salt
- alkyl sulfonyl
- preparation
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- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 150000003839 salts Chemical class 0.000 title abstract description 31
- 125000004390 alkyl sulfonyl group Chemical group 0.000 title abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000004321 preservation Methods 0.000 claims abstract description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 42
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 8
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims description 7
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052744 lithium Inorganic materials 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 239000012065 filter cake Substances 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 5
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 abstract description 11
- 239000002253 acid Substances 0.000 abstract description 10
- 150000008064 anhydrides Chemical class 0.000 abstract description 10
- 239000011230 binding agent Substances 0.000 abstract description 7
- 239000003960 organic solvent Substances 0.000 abstract description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 abstract description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract description 4
- 125000005463 sulfonylimide group Chemical group 0.000 abstract description 4
- 150000001339 alkali metal compounds Chemical class 0.000 abstract description 3
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000654 additive Substances 0.000 abstract description 2
- 229910001416 lithium ion Inorganic materials 0.000 abstract description 2
- -1 perfluoroalkyl sulfonimide salt Chemical class 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052793 cadmium Inorganic materials 0.000 description 3
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical class C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 3
- 229910052804 chromium Inorganic materials 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000011133 lead Substances 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 239000011733 molybdenum Substances 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- TUSPQEVATCMZOM-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluoro-4-(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyl)butane Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F TUSPQEVATCMZOM-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
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- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
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- 229910052718 tin Inorganic materials 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- QKIHLPFZYGFMDK-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F QKIHLPFZYGFMDK-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
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Abstract
本申请属于锂离子电池添加剂技术领域,公开了一种双全氟烷基磺酰亚胺盐的制备方法。所述制备方法包括:在惰性气氛保护下,将无水氨气通入到有机溶剂中得到氨气溶液;在氨气溶液中加入缚酸剂和全氟烷基磺酸酐,保温反应后得到双全氟烷基磺酰亚胺;将双全氟烷基磺酰亚胺与盐反应,得到双全氟烷基磺酰亚胺盐。本申请的制备方法采用全氟烷基磺酸酸酐与无水氨一步反应得到双全氟烷基磺酰亚胺,再与碱金属化合物反应得到双全氟烷基磺酰亚胺盐。具有路线简单,反应条件温和,反应效率高,三废少,产品纯度高的优点。
Description
技术领域
本申请涉及锂离子电池添加剂技术领域,具体涉及一种双全氟烷基磺酰亚胺盐的制备方法。
背景技术
双全氟烷基磺酰亚胺盐阴离子半径大,电荷分散度高,具有很好的电离能力,其化学稳定性和热稳定性好,常用于电解质材料,离子液体和反应催化剂等领域。
双三氟甲基磺酰亚胺盐(以下简称:MTFSI)是最常见研究最多的全氟烷基磺酰亚胺盐,其制备方法1972年即有报道。专利DE2239817经4步反应,最后经全氟烷基磺酰氟和N-三甲基硅基全氟磺酰胺反应,制备了双全氟烷基磺酰亚胺钠盐。DesMarteau等在1984年由全氟烷基磺酰氟和N-三甲基硅基全氟磺酰胺制备双全氟烷基磺酰亚胺钠盐后,经硫酸等酸化后,可制备双全氟烷基磺酰亚胺,进一步与盐或氧化物反应,可制备不同的双全氟烷基磺酰亚胺金属盐(Foropoulos,J.;DesMarteau,D.D.Inorg.Chem.1984,23,3720-3723)。
MTFSI的另外一种比较普遍的制备方法,是以无水氨,氨水或铵盐为原料,以有机胺或含氮杂环为缚酸剂,和全氟烷基磺酰卤反应,经全氟磺酰胺中间体,或者更进一步反应制备双全氟烷基磺酰亚胺中间体(或双全氟烷基磺酰亚胺铵盐中间体),再经碱性金属盐或者氧化物碱化后,制得相应的双全氟烷基磺酰亚胺盐(参见DE19533711,CN101456832,CN111051278,CN101983960,US5874616,US20010021790,CN103664712等)。专利CN102153493直接采用碱性金属盐作缚酸剂,三氟甲基磺酰卤和无水氨或者铵盐一步反应制备相应的双三氟甲基磺酰亚胺盐。专利CN101747244将全氟烷基磺酰胺先碱化制备全氟磺酰胺的金属盐,以提高其反应活性,然后与全氟烷基磺酰氟反应,在碳酸盐存在下,制备双全氟烷基磺酰亚胺盐。其他的制备MTFSI的方法还包括:美国专利US5072040将全氟烷基磺酰卤和金属氮化物反应,制备双全氟烷基磺酰亚胺盐。
韩国专利KR1673535报道了经3步反应制备N-(三取代硅基)双全氟烷基磺酰亚胺,再经碱性金属盐脱去有机硅后,生成相应的双全氟烷基磺酰亚胺盐。专利CN105949093以苄胺和全氟烷基磺酰卤或者全氟烷基磺酸酐反应,制备N-苄基双全氟烷基磺酰亚胺,经氢化脱去苄基,进一步经碱性金属盐碱化制备双全氟烷基磺酰亚胺盐。RomanArvai等报道了苄胺和全氟烷基磺酸酐反应,制备N-苄基双全氟烷基磺酰亚胺,再经乙醇活化后,和碱性金属盐反应,制备相应的双全氟烷基磺酰亚胺盐(Tetrahedron65(2009)5361-5368)。
中国专利CN109776362公开了一种双三氟磺酰亚胺盐的新工艺,包含如下步骤:S1:以伯胺和三氟甲基磺酸酐,制备相应的N-烷基取代的双三氟甲基磺酰亚胺;S2:将N-烷基取代的双三氟甲基磺酰亚胺与盐反应,得到粗产物;S3:将粗产物结晶,真空干燥,得到双三氟甲基磺酰亚胺盐。该方案的积极进步效果在于:N-烷基取代的双三氟甲基磺酰亚胺性质稳定,整个反应没有产生腐蚀性物质,三废较少。但该方案以伯胺和三氟甲基磺酸酐,所得N-烷基取代的双三氟甲基磺酰亚胺与盐反应的活性较低,往往需要加热回流反应10h以上,合成效率较低。
上述制备方法中,普遍存在原料昂贵或者制备困难,反应时间长,产品纯化困难,操作工序繁琐,环境污染大的缺陷,合成工艺有较大的改进空间。
发明内容
针对以上现有技术存在的缺点和不足之处,本申请的目的在于提供一种双全氟烷基磺酰亚胺盐的制备方法。本申请方法采用全氟烷基磺酸酸酐与无水氨一步反应得到双全氟烷基磺酰亚胺,再与碱金属化合物反应得到双全氟烷基磺酰亚胺盐。具有路线简单,反应条件温和,反应效率高,三废少,产品纯度高的优点。
本申请目的通过以下技术方案实现:
本申请提供一种双全氟烷基磺酰亚胺盐的制备方法,所述制备方法包括:
(1)在惰性气氛保护下,将无水氨气通入到有机溶剂中得到氨气溶液;
(2)在氨气溶液中加入缚酸剂和全氟烷基磺酸酐,保温反应后得到双全氟烷基磺酰亚胺;
(3)将双全氟烷基磺酰亚胺与盐反应,得到双全氟烷基磺酰亚胺盐;
所述双全氟烷基磺酰亚胺盐的结构式如式I所示:
式1中,R1和R2代表碳原子数相同或者不同的全氟烷基;M为铵、钠、钾、铁、钙、锂、铜、锌、镉、铬、铝、铅、镍、钼、钯、锡中的一种。
优选地,所述在惰性气氛保护下,将无水氨气通入到有机溶剂中得到氨气溶液,包括:
在惰性气氛保护下,将有机溶剂冷却到-10~-20℃后,通入无水氨气得到氨气溶液。
优选地,所述有机溶剂选自碳酸二乙酯、碳酸二甲酯、碳酸丙烯酯、碳酸乙烯酯、碳酸甲乙酯、四氢呋喃、甲基四氢呋喃、甲苯、二甲苯、氯苯、二氯苯、三氯苯、四氯苯、乙酸甲酯、乙酸乙酯、乙酸丙酯、乙酸异丙酯、乙酸丁酯、乙腈、乙二醇二甲醚、乙二醇二异***、二乙二醇二甲醚、丙酮、甲基异丁基酮、***、丙醚、丁醚、苯甲醚、二苯醚、1,4-二氧六环、二氯甲烷、三氯甲烷、四氯甲烷、二氯乙烷、三氯乙烷、四氯乙烷、四氯乙烯、γ-丁内酯中任意一种或多种组合。
更优选地,所述有机溶剂选自二氯甲烷或乙二醇二甲醚。
优选地,所述在氨气溶液中加入缚酸剂和全氟烷基磺酸酐,保温反应后得到双全氟烷基磺酰亚胺,包括:
加入全氟烷基磺酸酐时保持体系温度在0℃,加入结束后继续保温反应1~2h,再升温至室温继续反应1~2h。
更优选地,所述无水氨气与全氟烷基磺酸酐的摩尔比为1:2~1:3。
其中,所述缚酸剂选自有机碱或无机碱;
所述有机碱选自三甲胺、三乙胺、吡啶、4-二氨基吡啶、三乙烯二胺、四甲基丙二胺、乙基二异丙胺中的一种或多种组合;
所述无机碱选自钠、钾、铁、钙、锂、铜、锌、镉、铬、铝、铅、镍、钼、钯、锡的氢氧化物。
优选地,所述在氨气溶液中加入缚酸剂和全氟烷基磺酸酐,保温反应后得到双全氟烷基磺酰亚胺,包括:
保温反应结束后减压蒸馏脱除有机溶剂得到双全氟烷基磺酰亚胺。
优选地,所述将双全氟烷基磺酰亚胺与盐反应,得到双全氟烷基磺酰亚胺盐,包括:
将双全氟烷基磺酰亚胺与盐加入二氯甲烷或乙二醇二甲醚中,得到双全氟烷基磺酰亚胺盐。
更优选地,将双全氟烷基磺酰亚胺与盐加入乙二醇二甲醚中,室温反应2~3小时,过滤,滤液减压浓缩至浓稠状,滴加二氯甲烷,搅拌1~3小时后过滤,用二氯甲烷洗涤,滤饼在真空80~90℃干燥得到双全氟烷基磺酰亚胺盐。
优选地,所述盐为铵、钠、钾、铁、钙、锂、铜、锌、镉、铬、铝、铅、镍、钼、钯或锡的硼酸盐、碳酸盐、碳酸氢盐、硅酸盐、硝酸盐、亚硝酸盐、磷酸盐、磷酸氢盐、砷酸盐、硫酸盐、硫酸氢盐、硒酸盐、碲酸盐、氟盐、氯盐、溴盐、碘盐、砹盐中的任意一种。
与现有技术相比,本申请的有益效果是:
本申请方法采用全氟烷基磺酸酸酐与无水氨一步反应得到双全氟烷基磺酰亚胺,再与碱金属化合物反应得到双全氟烷基磺酰亚胺盐。具有路线简单,反应条件温和(常温条件下即可),反应效率高(与盐反应只需2~4h,收率可达90%以上),三废少,产品纯度高的优点。
附图说明
图1为本发明实施例3中所得产物双三氟甲基磺酰亚胺锂的离子色谱图。
具体实施方式
下面结合实施例及附图对本申请作进一步详细的描述,但本申请的实施方式不限于此。
实施例1
(1)在氮气保护下,将200g干燥二氯甲烷冷却到-15℃,通入3.4g氨气配制氨气溶液。加入40.47g三乙胺,滴加112.85g三氟甲基磺酸酐,滴加时间约2小时,保持体系温度在0℃,滴加结束后继续保温2小时,再缓慢升温1小时左右至室温,继续室温反应1小时。脱去溶剂后减压蒸馏,得到双三氟甲基磺酰亚胺50.61g。
(2)取8.48g无水氯化锂和双三氟甲基磺酰亚胺50.61g,加入到100g乙二醇二甲醚中,室温反应2小时,过滤,滤液减压浓缩至浓稠状,滴加二氯甲烷200g,20℃搅拌2小时后过滤,用二氯甲烷洗涤,滤饼真空80℃干燥得到双三氟甲基磺酰亚胺锂52.09g,收率为90.71%,水分小于100ppm,酸值小于150ppm,氯离子小于5ppm。
实施例2
(1)在氮气保护下,将200g干燥二氯甲烷冷却到-15℃,通入3.4g氨气配制氨气溶液。加入40.47g三乙胺,滴加232.87g全氟丁基磺酸酐,滴加时间约3小时,保持体系温度在0℃,滴加结束后继续保温2小时,再缓慢升温1小时左右至室温,继续室温反应1小时。脱去溶剂后减压蒸馏,得到双全氟丁基磺酰亚胺55.04g。
(2)取8.48g无水氯化锂和双全氟丁基磺酰亚胺55.04g,加入到100g乙二醇二甲醚中,室温反应2小时,过滤,滤液减压浓缩至浓稠状,滴加二氯甲烷200g,20℃搅拌2小时后过滤,用二氯甲烷洗涤,滤饼真空80℃干燥得到得到双全氟丁基磺酰亚胺锂54.49g,收率为89%,水分小于100ppm,酸值小于100ppm,氯离子小于5ppm。
实施例3
(1)在氮气保护下,200g干燥乙二醇二甲醚冷却到-15℃,通入3.4g氨气配制氨气溶液。加入55.28g碳酸钾,滴加112.85g三氟甲基磺酸酐,滴加时间约2小时,保持体系温度在0℃,滴加结束后继续保温2小时,再缓慢升温1小时左右至室温,继续室温反应1小时。过滤除去不溶物,得到双三氟甲基磺酰亚胺乙二醇二甲醚溶液。离子色谱测定浓度为20.81%。
(2)在上述230g乙二醇二甲醚溶液加入7.36g无水氯化锂室温反应2小时,过滤,滤液减压浓缩至浓稠状,滴加二氯甲烷200g,20℃搅拌2小时后过滤,用二氯甲烷洗涤,滤饼真空80℃干燥得到双三氟甲基磺酰亚胺锂44.48g,产物的离子色谱图如图1所示,收率为91%,水分小于110ppm,酸值小于100ppm,氯离子小于5ppm。
通过以上实施例结果可见,本申请采用无水氨进行反应,与现有技术中以伯胺和三氟甲基磺酸酐,制得N-烷基取代的双三氟甲基磺酰亚胺相比,其于后续双全氟烷基磺酰亚胺与盐反应效率更高。
上述实施例为本申请较佳的实施方式,但本申请的实施方式并不受上述实施例的限制,其它的任何未背离本申请的精神实质与原理下所作的改变、修饰、替代、组合、简化,均应为等效的置换方式,都包含在本申请的保护范围之内。
Claims (1)
1.一种双全氟烷基磺酰亚胺盐的制备方法,其特征在于,所述制备方法包括:
(1)在氮气保护下,200g干燥乙二醇二甲醚冷却到-15℃,通入3.4g氨气配制氨气溶液,加入55.28g碳酸钾,滴加112.85g三氟甲基磺酸酐,滴加时间2小时,保持体系温度在0℃,滴加结束后继续保温2小时,再缓慢升温1小时至室温,继续室温反应1小时,过滤除去不溶物,得到双三氟甲基磺酰亚胺乙二醇二甲醚溶液;
(2)在230g步骤(1)所得双三氟甲基磺酰亚胺乙二醇二甲醚溶液加入7.36g无水氯化锂室温反应2小时,过滤,滤液减压浓缩至浓稠状,滴加二氯甲烷200g,20℃搅拌2小时后过滤,用二氯甲烷洗涤,滤饼真空80℃干燥得到双三氟甲基磺酰亚胺锂44.48g。
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