CN1326835C - 有磺酰氟端基的全氟化乙烯基醚的制备 - Google Patents
有磺酰氟端基的全氟化乙烯基醚的制备 Download PDFInfo
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- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 title claims abstract description 14
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical group FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 title abstract description 3
- 238000002360 preparation method Methods 0.000 title description 7
- 238000000034 method Methods 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 238000003682 fluorination reaction Methods 0.000 claims abstract description 4
- QQFGOTHONVYTNR-UHFFFAOYSA-N CC1OC1.F.F.F.F.F.F Chemical compound CC1OC1.F.F.F.F.F.F QQFGOTHONVYTNR-UHFFFAOYSA-N 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 150000001457 metallic cations Chemical class 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 5
- 238000005336 cracking Methods 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- 239000002798 polar solvent Substances 0.000 claims description 2
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 abstract description 9
- 229910052751 metal Inorganic materials 0.000 abstract description 4
- 239000002184 metal Substances 0.000 abstract description 4
- 150000001768 cations Chemical class 0.000 abstract 1
- 238000004227 thermal cracking Methods 0.000 abstract 1
- 239000011734 sodium Substances 0.000 description 5
- OIUVUINPJBFCCD-UHFFFAOYSA-N 2,2,3,3,4,4-hexafluoro-4-fluorosulfonylbutanoyl fluoride Chemical compound FC(=O)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O OIUVUINPJBFCCD-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 3
- HANHEAJUUCXXRG-UHFFFAOYSA-N 3-butoxypropanoyl fluoride Chemical compound CCCCOCCC(F)=O HANHEAJUUCXXRG-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- -1 aliphatic ether carbonyl fluoride compound Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- JAAGVIUFBAHDMA-UHFFFAOYSA-M rubidium bromide Chemical compound [Br-].[Rb+] JAAGVIUFBAHDMA-UHFFFAOYSA-M 0.000 description 2
- WFUBYPSJBBQSOU-UHFFFAOYSA-M rubidium iodide Chemical compound [Rb+].[I-] WFUBYPSJBBQSOU-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000008053 sultones Chemical class 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- LYQFWZFBNBDLEO-UHFFFAOYSA-M caesium bromide Chemical compound [Br-].[Cs+] LYQFWZFBNBDLEO-UHFFFAOYSA-M 0.000 description 1
- XQPRBTXUXXVTKB-UHFFFAOYSA-M caesium iodide Chemical compound [I-].[Cs+] XQPRBTXUXXVTKB-UHFFFAOYSA-M 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 150000002222 fluorine compounds Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 1
- 235000007715 potassium iodide Nutrition 0.000 description 1
- 229960004839 potassium iodide Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
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- 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
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/78—Halides of sulfonic acids
- C07C309/79—Halides of sulfonic acids having halosulfonyl groups bound to acyclic carbon atoms
- C07C309/82—Halides of sulfonic acids having halosulfonyl groups bound to acyclic carbon atoms of a carbon skeleton substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
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- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/27—Halogenation
- C25B3/28—Fluorination
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Abstract
提供一种制备化学式FSO2-(CF2)n-O-CF＝CF2的有磺酰氟端基的全氟化乙烯基醚的方法，式中n为2-5，该方法包括下列步骤：a)使下述化学式氟化，形成FSO2-(CF2)(n-1)-COF；b)使FSO2-(CF2)(n-1)-COF与六氟环氧丙烷(HFPO)反应，形成FSO2-(CF2)(n)-O-CF(CF3)-COF；c)使FSO2-(CF2)(n)-O-CF(CF3)-COF与金属阳离子M+P盐反应形成(FSO2-(CF2)(n)-O-CF(CF3)-COO-)pM+P，其中p是M的价数；和d)使(FSO2-(CF2)(n)-O-CF(CF3)-COO-)pM+P热裂解，形成FSO2-(CF2)(n)-O-CF＝CF2。
Description
发明领域
本发明涉及四步法制备化学式FSO2-(CF2)n-O-CF＝CF2的有磺酰氟端基的全氟化乙烯基醚的方法，式中n为2-5，有磺酰氟端基的全氟化乙烯基醚是合成离子交换树脂中的一类重要的单体。
发明背景
US 4,749,526公开一种制备含氟脂族醚碳酰氟化合物的方法，即使氟化羰基化合物与六氟环氧丙烷在至少一种选自下列的催化剂存在下反应：碘化钾，溴化钾，碘化铯，溴化铯，碘化铷和溴化铷。
US 5,902,908公开一种制备氟化乙烯基醚的方法，该方法为使氟化酰基卤与金属化合物在低于相应金属盐的分解温度下，没有溶剂下反应，然后将产生的相应金属盐温度升高至高于分解温度。
US 6,255,536公开一种制备化学式CF2＝CF-O-Rf全氟化乙烯基醚的方法，式中Rf是可含有氧原子的直链，支链或环状的全氟化脂族基团，从而能形成另外的醚键。
发明概述
简短地，本发明提供一种制备化学式FSO2-(CF2)n-O-CF＝CF2的有磺酰氟端基的全氟化乙烯基醚的方法，式中n为2-5，该方法包括下列步骤：a)使
氟化，形成FSO2-(CF2)(n-1)-COF；b)使FSO2-(CF2)(n-1)-COF与六氟环氧丙烷(HFPO)反应，形成FSO2-(CF2)(n)-O-CF(CF3)-COF；c)使FSO2-(CF2)(n)-O-CF(CF3)-COF与金属阳离子M+P盐反应形成(FSO2-(CF2)(n)-O-CF(CF3)-COO-)pM+p，其中p是M的价数；和d)使(FSO2-(CF2)(n)-O-CF(CF3)-COO-)pM+p热裂解，形成FSO2-(CF2)(n)-O-CF＝CF2。
本发明的优点是提供一种制备化学式FSO2-(CF2)n-O-CF＝CF2的有磺酰氟端基的全氟化乙烯基醚的方便和有效的方法，该方法特别适用于n为2-5的情况，尤其是n为4的情况，这些物质是合成离子交换树脂的重要单体。本发明另一优点是提供一种制备化学式FSO2-(CF2)n-O-CF＝CF2的有磺酰氟端基的全氟化乙烯基醚的方法，式中n为2-5，该方法不需要使用四氟乙烯(TFE)，而使用四氟乙烯有危险和困难。
优选实施方式的详细说明
简短地，本发明提供一种制备化学式FSO2-(CF2)n-O-CF＝CF2的有磺酰氟端基的全氟化乙烯基醚的方法，式中n为2-5，该方法包括下列步骤：
a)使
氟化，形成FSO2-(CF2)(n-1)-COF；b)使FSO2-(CF2)(n-1)-COF与六氟环氧丙烷(HFPO)反应，形成FSO2-(CF2)(n)-O-CF(CF3)-COF；c)使FSO2-(CF2)(n)-O-CF(CF3)-COF与金属阳离子M+p盐反应形成(FSO2-(CF2)(n)-O-CF(CF3)-COO-)pM+p，其中p是M的价数；和d)使(FSO2-(CF2)(n)-O-CF(CF3)-COO-)pM+P热裂解，形成FSO2-(CF2)(n)-O-CF＝CF2。n值为2-5，典型为3-4，最典型是4。p值典型为1或2，最典型是1。金属阳离子M+p的盐最典型是Na2CO3。
步骤a)涉及使磺内酯氟化形成FSO2-(CF2)(n-1)-COF，磺内酯为下面化学式的4-7元环：
式中，n为2-5。该氟化可采用任何合适的方式进行，但最典型的是通过U.S.2,732,398中所述的电化学氟化进行。
步骤b)涉及使FSO2-(CF2)(n-1)-COF与六氟环氧丙烷(HFPO)反应，形成FSO2-(CF2)(n)-O-CF(CF3)-COF。步骤b)可采用任何合适的方式进行，但典型的是，将HFPO加到FSO2-(CF2)(n-1)-COF在合适极性溶剂如二甘醇二甲醚的溶液中进行。通常，存在一种催化剂。催化剂通常是氟化物催化剂，最典型的是KF。该反应在除氟化物催化剂外没有其它催化剂存在下进行。通常，HFPO加入的摩尔量不超过存在的FSO2-(CF2)(n-1)-COF的摩尔量。更典型地，FSO2-(CF2)(n-1)-COF摩尔量保持超过HFPO摩尔量至少10％，更典型20％，最典型30％。步骤b)可采用与本申请同日提交的待审美国专利申请10/322,254(代理号57659US002)公开的方法进行。
步骤c)涉及FSO2-(CF2)(n)-O-CF(CF3)-COF与金属阳离子M+p盐反应形成(FSO2-(CF2)(n)-O-CF(CF3)-COO-)pM+p，其中p是M的价数。P可以是任何值，但典型是1或2，最典型是1。M可以是任何合适金属，但典型的选自Na，K，Rb和Cs，最典型是Na。盐阴离子可以是任何合适的阴离子，但典型的不是碱性的，以从磺酰氟官能团除去氟。金属阳离子M+P的盐最典型是Na2CO3。步骤c)通常在极性溶剂中进行，如甘醇二甲醚，二甘醇二甲醚等。步骤c)通常在升高温度，通常是40-100℃下进行。
步骤d)涉及除去溶剂后，使(FSO2-(CF2)(n)-O-CF(CF3)-COO-)pM+p热裂解，形成FSO2-(CF2)(n)-O-CF＝CF2。可使用任何足以将(FSO2-(CF2)(n)-O-CF(CF3)-COO-)pM+p温度升高至其分解温度的热源。分解温度随反应物而不同，但通常在160-210℃范围。通常，在热裂解之前通常通过应用真空或减压除去所有残留的溶剂。然后收集产物，并通过任何合适的方式分离和纯化。
会理解，在本发明方法的一个或多个步骤后宜分离和纯化反应产物。
本发明对合成有磺酰氟端基的全氟化乙烯基醚有用，全氟化乙烯基醚是合成离子交换树脂的一类重要单体。
由下面实施例进一步说明本发明的目的和优点，但是在这些实施例中列举的具体物质及其用量，以及其它条件和细节不应视为对本发明的限制。
实施例
除非是有说明，所有的反应试剂都可从Aldrich Chemical Co.，Milwaukee，WI获得，或可通过已知方法合成。
按照U.S.No.2,732,398所述，1，4-丁烷磺内酯(6900g，50.7m)用HF电化学氟化，得到4-(氟磺酰基)六氟丁酰氟，FSO2(CF2)3COF(4000g，14.3m，产率28％)。
B.FSO2-CF2CF2CF2-COF+CF3CFOCF2+KF→
FSO2-CF2CF2CF2CF2-O-CF(CF3)-COF
2162g(7.7m)4-(氟磺酰基)六氟丁酰氟，FSO2(CF2)3COF，与等摩尔量的六氟环氧丙烷(HFPO)(1281g，7.7m)在2L二甘醇二甲醚中与114g氟化钾反应，得到全氟-4-(氟磺酰基)丁氧基丙酰氟(2250g，5.1m，产率65％)和675g含有另外的六氟环氧丙烷单元的高沸点副产物。
C.FSO2-CF2CF2CF2CF2-O-CF(CF3)-COF+Na2CO3+热量→
FSO2-CF2CF2CF2CF2-O-CF＝CF2
1108g(2.5m)全氟-4-(氟磺酰基)丁氧基丙酰氟然后与碳酸钠(603g，5.7m)在甘醇二甲醚中于70℃反应，产生该酸的钠盐。然后真空下除去溶剂，干盐加热至165℃，真空下分解而有二氧化碳副产物，继续加热最高至182℃，分离全氟-4-(氟磺酰基)丁氧基乙烯基醚(703g，1.9m，产率74％)。
在不偏离本发明范围和原理下，本发明的各种修改和变动对本领域技术人员是显而易见，应理解本发明不限于在此列出的说明性实施方式。
Claims (9)
1.一种制备化学式FSO2-(CF2)n-O-CF＝CF2的有磺酰氟端基的全氟化乙烯基醚的方法，式中n为2-5，该方法包括下列步骤：a)使
氟化，形成FSO2-(CF2)(n-1)-COF；
b)使FSO2-(CF2)(n-1)-COF与六氟环氧丙烷反应，形成FSO2-(CF2)(n)-O-CF(CF3)-COF，
FSO2-(CF2)(n-1)-COF摩尔量保持超过六氟环氧丙烷摩尔量至少10％；
c)使FSO2-(CF2)(n)-O-CF(CF3)-COF与金属阳离子M+p盐反应形成(FSO2-(CF2)(n)-O-CF(CF3)-COO-)pM+p，其中p是M的价数；和
d)使(FSO2-(CF2)(n)-O-CF(CF3)-COO-)pM+p热裂解，形成FSO2-(CF2)(n)-O-CF＝CF2。
2.如权利要求1所述的方法，其特征在于，n＝4。
3.如权利要求1所述的方法，其特征在于，步骤c)在极性溶剂中进行。
4.如权利要求1所述的方法，其特征在于，所述金属阳离子的盐是Na2CO3。
5.如权利要求1-4中任一项所述的方法，其特征在于，所述步骤b)在氟化物催化剂存在下进行。
6.如权利要求1-4中任一项所述的方法，其特征在于，所述步骤b)在除氟化物催化剂外没有其他催化剂存在下进行。
7.如权利要求5所述的方法，其特征在于，所述氟化物催化剂是KF。
8.如权利要求6所述的方法，其特征在于，所述氟化物催化剂是KF。
9.如权利要求1-4中任一项所述的方法，其特征在于，所述步骤a)包括电化学氟化。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/322,226 | 2002-12-17 | ||
| US10/322,226 US6624328B1 (en) | 2002-12-17 | 2002-12-17 | Preparation of perfluorinated vinyl ethers having a sulfonyl fluoride end-group |
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| Publication Number | Publication Date |
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| CN1726186A CN1726186A (zh) | 2006-01-25 |
| CN1326835C true CN1326835C (zh) | 2007-07-18 |
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| CNB2003801059303A Expired - Fee Related CN1326835C (zh) | 2002-12-17 | 2003-11-04 | 有磺酰氟端基的全氟化乙烯基醚的制备 |
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|---|---|
| US (1) | US6624328B1 (zh) |
| EP (1) | EP1572633A1 (zh) |
| JP (1) | JP4473139B2 (zh) |
| KR (1) | KR20050085696A (zh) |
| CN (1) | CN1326835C (zh) |
| AU (1) | AU2003290576A1 (zh) |
| CA (1) | CA2506456A1 (zh) |
| WO (1) | WO2004060857A1 (zh) |
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Also Published As
| Publication number | Publication date |
|---|---|
| WO2004060857A1 (en) | 2004-07-22 |
| AU2003290576A1 (en) | 2004-07-29 |
| JP4473139B2 (ja) | 2010-06-02 |
| US6624328B1 (en) | 2003-09-23 |
| EP1572633A1 (en) | 2005-09-14 |
| CN1726186A (zh) | 2006-01-25 |
| CA2506456A1 (en) | 2004-07-22 |
| KR20050085696A (ko) | 2005-08-29 |
| JP2006510720A (ja) | 2006-03-30 |
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