JP2012532870A - ポリフルオロスルホンアミドアミンおよび中間体 - Google Patents
ポリフルオロスルホンアミドアミンおよび中間体 Download PDFInfo
- Publication number
- JP2012532870A JP2012532870A JP2012519594A JP2012519594A JP2012532870A JP 2012532870 A JP2012532870 A JP 2012532870A JP 2012519594 A JP2012519594 A JP 2012519594A JP 2012519594 A JP2012519594 A JP 2012519594A JP 2012532870 A JP2012532870 A JP 2012532870A
- Authority
- JP
- Japan
- Prior art keywords
- product
- formula
- sulfonamide
- polyfluorosulfonamidoamine
- bis
- 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.)
- Withdrawn
Links
- 239000000543 intermediate Substances 0.000 title description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 31
- 150000004985 diamines Chemical class 0.000 claims abstract description 19
- 229940124530 sulfonamide Drugs 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 15
- 150000002148 esters Chemical class 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 238000005947 deacylation reaction Methods 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 230000020176 deacylation Effects 0.000 claims description 12
- -1 sulfonamide amide Chemical class 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000013067 intermediate product Substances 0.000 claims description 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 3
- 239000006260 foam Substances 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 239000006227 byproduct Substances 0.000 abstract description 26
- 239000000047 product Substances 0.000 abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 11
- 230000015572 biosynthetic process Effects 0.000 abstract description 10
- 229910052731 fluorine Inorganic materials 0.000 abstract description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 abstract description 5
- 239000011737 fluorine Substances 0.000 abstract description 5
- 239000000376 reactant Substances 0.000 abstract description 5
- 239000007858 starting material Substances 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 239000012535 impurity Substances 0.000 abstract description 2
- 230000000704 physical effect Effects 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 150000003460 sulfonic acids Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 238000004817 gas chromatography Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000010926 purge Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- IUFSPJKPPQWECZ-UHFFFAOYSA-N N-[3-[1,1,2,2,2-pentafluoroethylsulfonyl(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)amino]propyl]acetamide Chemical compound C(C)(=O)NCCCN(S(=O)(=O)C(C(F)(F)F)(F)F)C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F IUFSPJKPPQWECZ-UHFFFAOYSA-N 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZUDDFQJTUVAEGR-UHFFFAOYSA-N acetamide;propane-1,3-diamine Chemical compound CC(N)=O.CC(N)=O.NCCCN ZUDDFQJTUVAEGR-UHFFFAOYSA-N 0.000 description 3
- TYKPMMIFXVBTDJ-UHFFFAOYSA-N acetamide;propane-1,3-diamine Chemical compound CC(N)=O.NCCCN TYKPMMIFXVBTDJ-UHFFFAOYSA-N 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- MTTJUCUTTQQNCG-UHFFFAOYSA-N 1,1,1,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-2-sulfonyl chloride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(C(F)(F)F)S(Cl)(=O)=O MTTJUCUTTQQNCG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- SOHFOIUQOCUZOO-UHFFFAOYSA-N acetamide;propane-1,3-diamine;hydrochloride Chemical compound Cl.CC(N)=O.NCCCN SOHFOIUQOCUZOO-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropyl acetate Chemical compound CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- NUKZAGXMHTUAFE-UHFFFAOYSA-N methyl hexanoate Chemical compound CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 2
- SCZVXVGZMZRGRU-UHFFFAOYSA-N n'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- UDEWPOVQBGFNGE-UHFFFAOYSA-N propyl benzoate Chemical compound CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KFNNIILCVOLYIR-UHFFFAOYSA-N Propyl formate Chemical compound CCCOC=O KFNNIILCVOLYIR-UHFFFAOYSA-N 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- BCQSKNWLNHYIFN-UHFFFAOYSA-N acetamide propane-1,3-diamine Chemical compound C(C)(=O)N.NCCCN.C(C)(=O)N.NCCCN BCQSKNWLNHYIFN-UHFFFAOYSA-N 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- CFNHVUGPXZUTRR-UHFFFAOYSA-N n'-propylethane-1,2-diamine Chemical compound CCCNCCN CFNHVUGPXZUTRR-UHFFFAOYSA-N 0.000 description 1
- UQUPIHHYKUEXQD-UHFFFAOYSA-N n,n′-dimethyl-1,3-propanediamine Chemical compound CNCCCNC UQUPIHHYKUEXQD-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- AOCUKGFDRUSDQH-PIKKTMSISA-N ocrf Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H]1N(CCC1)C(=O)[C@H]1N(CCC1)C(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CO)[C@@H](C)CC)C(C)CC)[C@@H](C)O)C(C)C)C(C)O)C1=CNC=N1 AOCUKGFDRUSDQH-PIKKTMSISA-N 0.000 description 1
- 150000003901 oxalic acid esters Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- HTUIWRWYYVBCFT-UHFFFAOYSA-N propyl hexanoate Chemical compound CCCCCC(=O)OCCC HTUIWRWYYVBCFT-UHFFFAOYSA-N 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003503 terephthalic acid derivatives Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/09—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by at least two halogen atoms
-
- 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
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/38—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides 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
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/500,817 | 2009-07-10 | ||
| US12/500,817 US8258341B2 (en) | 2009-07-10 | 2009-07-10 | Polyfluorosulfonamido amine and intermediate |
| PCT/US2010/040728 WO2011005642A1 (en) | 2009-07-10 | 2010-07-01 | Polyfluorosulfonamido amides useful as intermediates in the synthesis of polyfluorosulfonamido amines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012532870A true JP2012532870A (ja) | 2012-12-20 |
| JP2012532870A5 JP2012532870A5 (enExample) | 2013-08-15 |
Family
ID=42793397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012519594A Withdrawn JP2012532870A (ja) | 2009-07-10 | 2010-07-01 | ポリフルオロスルホンアミドアミンおよび中間体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8258341B2 (enExample) |
| EP (1) | EP2451777A1 (enExample) |
| JP (1) | JP2012532870A (enExample) |
| KR (1) | KR20120034227A (enExample) |
| CN (1) | CN102482206A (enExample) |
| CA (1) | CA2764427A1 (enExample) |
| WO (1) | WO2011005642A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013523646A (ja) * | 2010-03-25 | 2013-06-17 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ポリフルオロアルキルスルホンアミドアルキルアミンの混合物 |
| JP2013523644A (ja) * | 2010-03-25 | 2013-06-17 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ポリフルオロアルキルスルホンアミドアルキルアミンによる界面活性剤組成物 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20130067093A1 (en) * | 2010-03-16 | 2013-03-14 | Optimi Corporation | Determining Essential Resources in a Wireless Network |
| JP5522501B2 (ja) * | 2012-05-18 | 2014-06-18 | Ｄｉｃ株式会社 | フッ素化脂肪族基を含むスルホニルアミド化合物の製造方法及びアニオン性親水基含有界面活性剤の製造方法 |
| JP5920024B2 (ja) * | 2012-05-25 | 2016-05-18 | Dic株式会社 | フッ素化脂肪族基を含むスルホニルアミド化合物の製造方法及びアニオン性親水基含有界面活性剤の製造方法 |
| CN105519067B (zh) * | 2013-09-18 | 2020-04-03 | 华为技术有限公司 | 传输信令的方法、装置和计算机可读介质 |
| EP4175310A1 (en) | 2021-10-28 | 2023-05-03 | Koninklijke Philips N.V. | Checking locality of devices |
| WO2023036523A1 (en) | 2021-09-09 | 2023-03-16 | Koninklijke Philips N.V. | Checking locality of devices |
Family Cites Families (55)
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| DE1259333B (de) * | 1964-03-09 | 1968-01-25 | Minnesota Mining & Mfg | Verfahren zur Herstellung von N-Alkyl-perfluoralkansulfon-amidoalkyl-arylsulfonsaeureestern |
| FR2029262A5 (enExample) | 1969-01-22 | 1970-10-16 | Ugine Kuhlmann | |
| FR2034142B1 (enExample) | 1969-02-11 | 1975-07-04 | Ugine Kuhlmann | |
| NL7103340A (enExample) | 1970-03-19 | 1971-09-21 | ||
| FR2088594A5 (enExample) | 1970-04-17 | 1972-01-07 | Ugine Kuhlmann | |
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| FR2308674A1 (fr) | 1975-04-25 | 1976-11-19 | Ugine Kuhlmann | Nouvelles compositions extinctrices |
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| EP0004919B1 (de) | 1978-04-14 | 1981-06-10 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von N,N,N',N'-Tetraacetyl-ethylendiamin |
| JPS5838570Y2 (ja) | 1979-03-27 | 1983-09-01 | アルプス電気株式会社 | 小型可変抵抗器 |
| FR2477144A1 (fr) | 1980-02-29 | 1981-09-04 | Ugine Kuhlmann | Nouveaux oxydes d'amines a groupement perfluoroalkyle et utilisation de ces produits dans des compositions extinctrices |
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| JPS5838569B2 (ja) | 1980-12-09 | 1983-08-24 | 嘉平衛 下村 | 地盤固結工法 |
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| JPS6019257B2 (ja) | 1981-09-02 | 1985-05-15 | 大日本インキ化学工業株式会社 | 消火剤 |
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| JPS59230566A (ja) | 1983-05-31 | 1984-12-25 | 大日本インキ化学工業株式会社 | 消火薬剤 |
| JPS6099272A (ja) | 1983-11-04 | 1985-06-03 | 大日本インキ化学工業株式会社 | 泡消火薬剤 |
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| DE3708316A1 (de) | 1987-03-14 | 1988-09-22 | Bayer Ag | Fluorierte alkylamidosulfonate, deren herstellung, deren verwendung als flammschutzmittel und sie enthaltende polycarbonatformmassen |
| WO1990003956A1 (en) | 1988-10-06 | 1990-04-19 | Benchmark Structural Ceramics Corporation | Process for making a silicon carbide composition |
| JPH05235705A (ja) | 1992-02-17 | 1993-09-10 | Fujitsu Ltd | Ｒｓフリップフロップ回路 |
| JP3217116B2 (ja) | 1992-03-06 | 2001-10-09 | 日産化学工業株式会社 | 低表面張力洗浄用組成物 |
| JPH05275406A (ja) | 1992-03-24 | 1993-10-22 | Mitsubishi Kasei Corp | 硫酸組成物 |
| JPH05275407A (ja) | 1992-03-24 | 1993-10-22 | Mitsubishi Kasei Corp | 硫酸組成物 |
| US6201122B1 (en) | 1992-12-08 | 2001-03-13 | 3M Innovative Properties Company | Fluoroaliphatic radical-containing anionic sulfonamido compounds |
| DE4325485A1 (de) | 1993-07-29 | 1995-02-02 | Bayer Ag | Verfahren zur Herstellung flüssiger Aminaddukte fluorgruppenhaltiger Amide |
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| WO1999029373A1 (en) | 1997-12-10 | 1999-06-17 | Minnesota Mining And Manufacturing Company | Fire-fighting agents containing adsorbable fluorocarbon surfactants |
| DE19800531A1 (de) * | 1998-01-09 | 1999-07-15 | Bayer Ag | Verfahren zur Herstellung von N-(3-Amino-4-fluor-phenyl)-sulfonsäureamiden, N-(3-Amino-4-fluor-phenyl)-carbonsäureamiden und N-(3-Amino-4-fluor-phenyl)-carbamaten |
| FR2778836B1 (fr) | 1998-05-25 | 2000-06-30 | Maurice Granger | Tambour de distribution de materiau d'essuyage dans un appareil distributeur avec reglage du format et de la longueur du materiau debite |
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| JP4701470B2 (ja) | 2000-01-17 | 2011-06-15 | Ｄｉｃ株式会社 | 消火薬剤 |
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| KR100446659B1 (ko) | 2001-05-09 | 2004-09-04 | 주식회사 엘지화학 | 비이온성 계면활성제를 포함하는 전해액과 이를 이용하는리튬이온 전지 |
| WO2005001979A2 (en) | 2003-06-27 | 2005-01-06 | E.I. Dupont De Nemours And Company | Fluorinated sulfonamide compounds and polymer electrolyte membranes pepared therefrom for use in electrochemical cells |
| CN1291764C (zh) | 2003-10-09 | 2006-12-27 | 西南石油学院 | 一种油类快速灭火剂 |
| US7541492B2 (en) | 2005-10-26 | 2009-06-02 | Toyota Jidosha Kabushiki Kaisha | Perfluoroalkanesulfonamide compounds |
| JP5239238B2 (ja) | 2006-07-26 | 2013-07-17 | セントラル硝子株式会社 | フルオロアルカンスルホンアミド誘導体の製造方法 |
| CN101589076B (zh) | 2007-01-19 | 2012-05-23 | 3M创新有限公司 | 氟化表面活性剂及其使用方法 |
| US7728163B2 (en) * | 2007-08-06 | 2010-06-01 | E.I. Du Pont De Nemours And Company | Mixed fluoroalkyl-alkyl surfactants |
| US20090137831A1 (en) | 2007-11-28 | 2009-05-28 | E. I. Du Pont De Nemours And Company | Fluorinated Alkanesulfonic Acid Esters and Amides and Processes for Making and Using the Same |
| US8058463B2 (en) | 2007-12-04 | 2011-11-15 | E. I. Du Pont De Nemours And Compnay | Fluorosilanes |
| US8153834B2 (en) * | 2007-12-05 | 2012-04-10 | E.I. Dupont De Nemours And Company | Surface modified inorganic particles |
| US8858813B2 (en) | 2008-12-11 | 2014-10-14 | 3M Innovative Properties Company | Patterning process |
-
2009
- 2009-07-10 US US12/500,817 patent/US8258341B2/en not_active Expired - Fee Related
-
2010
- 2010-07-01 CA CA2764427A patent/CA2764427A1/en not_active Abandoned
- 2010-07-01 KR KR1020127003468A patent/KR20120034227A/ko not_active Withdrawn
- 2010-07-01 JP JP2012519594A patent/JP2012532870A/ja not_active Withdrawn
- 2010-07-01 WO PCT/US2010/040728 patent/WO2011005642A1/en not_active Ceased
- 2010-07-01 EP EP10730955A patent/EP2451777A1/en not_active Withdrawn
- 2010-07-01 CN CN201080030765XA patent/CN102482206A/zh active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013523646A (ja) * | 2010-03-25 | 2013-06-17 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ポリフルオロアルキルスルホンアミドアルキルアミンの混合物 |
| JP2013523644A (ja) * | 2010-03-25 | 2013-06-17 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ポリフルオロアルキルスルホンアミドアルキルアミンによる界面活性剤組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| US8258341B2 (en) | 2012-09-04 |
| CN102482206A (zh) | 2012-05-30 |
| WO2011005642A1 (en) | 2011-01-13 |
| KR20120034227A (ko) | 2012-04-10 |
| EP2451777A1 (en) | 2012-05-16 |
| US20110009668A1 (en) | 2011-01-13 |
| CA2764427A1 (en) | 2011-01-13 |
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