JP2017538717A - ハロゲン化部分フッ素化化合物の製造方法 - Google Patents
ハロゲン化部分フッ素化化合物の製造方法 Download PDFInfo
- Publication number
- JP2017538717A JP2017538717A JP2017531854A JP2017531854A JP2017538717A JP 2017538717 A JP2017538717 A JP 2017538717A JP 2017531854 A JP2017531854 A JP 2017531854A JP 2017531854 A JP2017531854 A JP 2017531854A JP 2017538717 A JP2017538717 A JP 2017538717A
- Authority
- JP
- Japan
- Prior art keywords
- cfh
- compound
- formula
- integer
- iodine
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 60
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 59
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 47
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 27
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000011630 iodine Substances 0.000 claims abstract description 24
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 22
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 19
- 239000007864 aqueous solution Substances 0.000 claims abstract description 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 230000008569 process Effects 0.000 claims abstract description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- -1 tetraalkylammonium halides Chemical class 0.000 claims description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 6
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 6
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000203 mixture Substances 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 230000002051 biphasic effect Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 229910000831 Steel Inorganic materials 0.000 description 4
- 238000007259 addition reaction Methods 0.000 description 4
- 150000001336 alkenes Chemical group 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- LIZZWVXXYAALGG-UHFFFAOYSA-N 1,1,2,3,3-pentafluoro-3-fluorosulfonyloxyprop-1-ene Chemical compound FC(F)=C(F)C(F)(F)OS(F)(=O)=O LIZZWVXXYAALGG-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- SLFKPACCQUVAPG-UHFFFAOYSA-N carbon monoxide;nickel;triphenylphosphane Chemical compound O=C=[Ni]=C=O.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 SLFKPACCQUVAPG-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- IRJLLQVAPGBLNZ-UHFFFAOYSA-N cyclopropane 1,1,1,2,2-pentafluoropropane Chemical compound C1CC1.FC(C(F)(F)F)(C)F IRJLLQVAPGBLNZ-UHFFFAOYSA-N 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/12—Saturated ethers containing halogen
- C07C43/126—Saturated ethers containing halogen having more than one ether bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/08—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/087—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/208—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being MX
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
- C07C19/16—Acyclic saturated compounds containing halogen atoms containing fluorine and iodine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/20—Preparation of ethers by reactions not forming ether-oxygen bonds by hydrogenation of carbon-to-carbon double or triple bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
(a)式(I)
Rf−CF=CXY
(式中、X及びYは、独立してF及びClから選択され、Rfは、1〜10個の炭素原子を含むフッ素化一価基である。)の構造を有する化合物、を提供する工程と、
(b)上記化合物を、
(i)酸の存在下の、ヨウ素又は臭素含有塩、及び
(ii)HZの水溶液(式中、ZはI及びBrから選択される。)
のうちの少なくとも1つと接触させて、式(II)
R’f−CFH−CXYZ
(式中、X及びYは、独立してF及びClから選択され、ZはI及びBrから選択され、R’fは、1〜10個の炭素原子を含むフッ素化一価基である。)のハロゲン化部分フッ素化化合物を生成する工程と、を含む、部分フッ素化ハロゲン化化合物の製造方法が記載される。
「a」、「an」、及び「the」は互換可能に使用され、1又はそれよりも多くを意味する。
本開示は、式(I)
Rf−CF=CXY (I)
(式中、X及びYは、独立してF及びClから選択され、Rfは1〜10個の炭素原子を含むフッ素化一価基である。)の末端二重結合含有化合物へのヨウ素又は臭素含有化合物付加反応に関する。
[X’−CF2−CF=CF2、CF3−O−CF=CF2、C3F7−O−CF=CF2、CF3CF2CF2−O−CF(CF3)−CF2−O−CF=CF2、X’−(CF2)1−4−CF=CF2、CF3−O−(CF2)3−O−CF=CF2、CF2=CF−O−(CF2)2−4−O−CF=CF2、X’−CF2−CF2−O−(CF2)2−4−O−CF=CF2 CF2=CF−O−(CF2)2−4−O−CF2−CF=CF2、CF2=CF−CF2−O−(CF2)2−4−O−CF2−CF=CF2、X’−CF2−CF2−O−(CF2)2−4−O−CF2CF=CF2、X’−CF2−CF2−O−CF=CF2、X’−CF2−CF2−O−CF2−CF=CF2、X’−CF(CF3)−CF2−O−CF=CF2、X’−CF(CF3)−CF2−O−CF2−CF=CF2、X’−CF2−CF2−(O−CF(CF3)−CF2)1−2−O−CF=CF2、X’−CF2−CF2−(O−CF(CF3)−CF2)1−2−O−CF2−CF=CF2、X’−CF2−CF2−CF2−O−CF=CF2、X’−CF2−CF2−CF2−O−CF2−CF=CF2、X’−CF2−CF2−CF2−(O−CF(CF3)−CF2)1−2−O−CF=CF2、X’−CF2−CF2−CF2−(O−CF(CF3)−CF2)1−2−O−CF2−CF=CF2、X’−CF2−CF2−O−(CF2)2−(O−CF(CF3)CF2)1−2−O−CF2=CF2(式中、X’はBr、I、C(O)X”、及びSO2X”から選択され、X”はF、Cl、OH、及びこれらの塩から選択される。)]。代表的なC(O)OHの塩としては、例えば、アンモニウム塩、アルカリ及びアルカリ土類金属塩、例えば、C(O)ONaが挙げられる。
R’f−CFH−CXYZ (II)
(式中、X及びYは上記と同じであり、ZはI及びBrから選択され、R’fは一価のフッ素化基である。)のハロゲン化部分フッ素化化合物を生成することが発見された。
[X’−CF2−CFH−CF2−Z、CF3−O−CFH−CF2−Z、C3F7−O−CFH−CF2−Z、CF3CF2CF2−O−CF(CF3)−CF2−O−CFH−CF2−Z、X’−(CF2)1−4−CFH−CF2−Z、CF3−O−(CF2)3−O−CFH−CF2−Z、Z−CF2−CFH−O−(CF2)2−4−O−CF=CF2、Z−CF2−CFH−O−(CF2)2−4−O−CFH−CF2−Z、Z−CF2−CFH−O−(CF2)2−4−O−CF2−CF=CF2、Z−CF2−CFH−O−(CF2)2−4−O−CF2−CFH−CF2−Z、CF2=CF−O−(CF2)2−4−O−CF2−CFH−CF2−Z、Z−CF2−CFH−CF2−O−(CF2)2−4−O−CF2−CF=CF2、Z−CF2−CFH−CF2−O−(CF2)2−4−O−CF2−CFH−CF2−Z、X’−CF2−CF2−O−(CF2)2−4−O−CF2CFH−CF2−Z、X’−CF2−CF2−O−CFH−CF2−Z、X’−CF2−CF2−O−CF2−CFH−CF2−Z、X’−CF(CF3)−CF2−O−CFH−CF2−Z、X’−CF(CF3)−CF2−O−CF2−CFH−CF2−Z、X’−CF2−CF2−(O−CF(CF3)−CF2)1−2−O−CFH−CF2−Z、X’−CF2−CF2−(O−CF(CF3)−CF2)1−2−O−CF2−CFH−CF2−Z、X’−CF2−CF2−CF2−O−CFH−CF2−Z、X’−CF2−CF2−CF2−O−CF2−CFH−CF2−Z、X’−CF2−CF2−CF2−(O−CF(CF3)−CF2)1−2−O−CFH−CF2−Z、X’−CF2−CF2−CF2−(O−CF(CF3)−CF2)1−2−O−CF2−CFH−CF2−Z、X’−CF2−CF2−O−(CF2)2−(O−CF(CF3)CF2)1−2−O−CFH−CF2−Z(式中、ZはBr及びIであり、X’はBr、I、C(O)X”、及びSO2X”から選択され、X”はF、Cl、OH、及びこれらの塩から選択される。)]。代表的なC(O)OHの塩としては、例えば、アンモニウム塩、アルカリ及びアルカリ土類金属塩、例えば、C(O)ONaが挙げられる。
R”−CFH−CF2−CH=CH2
(式中、R”はX’−CF2−、CH2=CH−CF2−、CF3O−、CF3CF2CF2−O−、又はCF3−O−(CF2)3−O−から選択され、式中、X’はBr、I、C(O)X”、及びSO2X”から選択され、X”はF、Cl、OH、及びこれらの塩から選択される。)の部分フッ素化化合物を生成し得る。
(a)式(I)
Rf−CF=CXY
(式中、X及びYは、独立してF及びClから選択され、Rfは、1〜10個の炭素原子を含むフッ素化一価基である。)の構造を有する化合物、を提供する工程と、
(b)上記化合物を、
(i)酸の存在下の、ヨウ素又は臭素含有塩、及び
(ii)HZの水溶液(式中、ZはI及びBrから選択される。)
のうちの少なくとも1つと接触させて、式(II)
R’f−CFH−CXYZ
(式中、X及びYは、独立してF及びClから選択され、ZはI及びBrから選択され、R’fは、1〜10個の炭素原子を含むフッ素化一価基である。)のハロゲン化部分フッ素化化合物を生成する工程と、を含む、方法。
X’−CF2−CF=CF2、CF3−O−CF=CF2、C3F7−O−CF=CF2、CF3CF2CF2−O−CF(CF3)−CF2−O−CF=CF2、X’−(CF2)m−CF=CF2、CF3−O−(CF2)3−O−CF=CF2、CF2=CF−O−(CF2)n−O−CF=CF2、X’−CF2−CF2−O−(CF2)n−O−CF=CF2、CF2=CF−O−(CF2)n−O−CF2−CF=CF2、CF2=CF−CF2−O−(CF2)n−O−CF2−CF=CF2、X’−CF2−CF2−O−(CF2)n−O−CF2CF=CF2、X’−CF2−CF2−O−CF=CF2、X’−CF2−CF2−O−CF2−CF=CF2、X’−CF(CF3)−CF2−O−CF=CF2、X’−CF(CF3)−CF2−O−CF2−CF=CF2、X’−CF2−CF2−(O−CF(CF3)−CF2)p−O−CF=CF2、X’−CF2−CF2−(O−CF(CF3)−CF2)p−O−CF2−CF=CF2、X’−CF2−CF2−CF2−O−CF=CF2、X’−CF2−CF2−CF2−O−CF2−CF=CF2、X’−CF2−CF2−CF2−(O−CF(CF3)−CF2)p−O−CF=CF2、X’−CF2−CF2−CF2−(O−CF(CF3)−CF2)p−O−CF2−CF=CF2、及びX’−CF2−CF2−O−(CF2)2−(O−CF(CF3)CF2)p−O−CF2=CF2(式中、X’はBr、I、C(O)X”、及びSO2X”から選択され、X”はF、Cl、OH、及びこれらの塩から選択され、mは1〜4の整数であり、nは2〜4の整数であり、pは1〜2の整数である。)から選択される、実施形態1〜5のいずれか1つに記載の方法。
R”−CFH−CF2−CH=CH2
(式中、R”はX’−CF2−、CH2=CH−CF2−、CF3O−、CF3CF2CF2−O−、及びCF3−O−(CF2)3−O−から選択され、式中、X’はBr、I、C(O)X”、及びSO2X”から選択され、X”はF、Cl、OH、及びこれらの塩から選択される。)の化合物を生成する工程、を更に含む、実施形態13に記載の方法。
Claims (10)
- ハロゲン化部分フッ素化化合物の製造方法であって、
(a)式(I)
Rf−CF=CXY
(式中、X及びYは、独立してF及びClから選択され、Rfは、1〜10個の炭素原子を含むフッ素化一価基である。)の構造を有する化合物、を提供する工程と、
(c)前記化合物を
(iii)酸の存在下の、ヨウ素又は臭素含有塩、及び
(iv)HZの水溶液(式中、ZはI及びBrから選択される。)
のうちの少なくとも1つと接触させて、式(II)
R’f−CFH−CXYZ
(式中、X及びYは、独立してF及びClから選択され、ZはI及びBrから選択され、R’fは、1〜10個の炭素原子を含むフッ素化一価基である。)のハロゲン化部分フッ素化化合物を生成する工程と、を含む、方法。 - Rfが、少なくとも1個の連結された酸素又は硫黄原子を含む、請求項1に記載の方法。
- Rfが、−CF2−O−SO2F、−CF2I、−CF2Br、−O−(CF2)a−F、−O−(CF2)a−I、−O−(CF2)a−Br、−O−(CF2)b−O−CF=XY、(式中、X及びYは、独立してF及びClから選択され、aは1〜10の整数であり、bは2〜4の整数である。)から選択される、請求項1に記載の方法。
- 前記式(I)の化合物が、
X’−CF2−CF=CF2、CF3−O−CF=CF2、C3F7−O−CF=CF2、CF3CF2CF2−O−CF(CF3)−CF2−O−CF=CF2、X’−(CF2)m−CF=CF2、CF3−O−(CF2)3−O−CF=CF2、CF2=CF−O−(CF2)n−O−CF=CF2、X’−CF2−CF2−O−(CF2)n−O−CF=CF2、CF2=CF−O−(CF2)n−O−CF2−CF=CF2、CF2=CF−CF2−O−(CF2)n−O−CF2−CF=CF2、X’−CF2−CF2−O−(CF2)n−O−CF2CF=CF2、X’−CF2−CF2−O−CF=CF2、X’−CF2−CF2−O−CF2−CF=CF2、X’−CF(CF3)−CF2−O−CF=CF2、X’−CF(CF3)−CF2−O−CF2−CF=CF2、X’−CF2−CF2−(O−CF(CF3)−CF2)p−O−CF=CF2、X’−CF2−CF2−(O−CF(CF3)−CF2)p−O−CF2−CF=CF2、X’−CF2−CF2−CF2−O−CF=CF2、X’−CF2−CF2−CF2−O−CF2−CF=CF2、X’−CF2−CF2−CF2−(O−CF(CF3)−CF2)p−O−CF=CF2、X’−CF2−CF2−CF2−(O−CF(CF3)−CF2)p−O−CF2−CF=CF2、及びX’−CF2−CF2−O−(CF2)2−(O−CF(CF3)CF2)p−O−CF2=CF2(式中、X’はBr、I、C(O)X”、及びSO2X”から選択され、X”はF、Cl、OH、及びこれらの塩から選択され、mは1〜4の整数であり、nは2〜4の整数であり、pは1〜2の整数である。)から選択される、請求項1に記載の方法。 - 前記ヨウ素又は臭素含有塩が、ハロゲン化アルカリ、ハロゲン化アルカリ土類、及びハロゲン化テトラアルキルアンモニウムから選択される、請求項1に記載の方法。
- 前記酸のpKaが、大きくとも4.8である、請求項1に記載の方法。
- 前記式(I)の化合物を前記ヨウ素又は臭素含有塩と前記接触させる工程が、溶媒の存在下で起こり、前記溶媒が、任意に、アセトニトリル、ジグリム、モノグリム、プロピオニトリル、テトラグリム、トリグリム、テトラヒドロフラン、及び水から選択される、請求項1に記載の方法。
- 前記化合物を前記ヨウ素若しくは臭素含有塩又は前記HZの水溶液と前記接触させる工程が、1〜20barの圧力及び20〜200℃の温度で実施される、請求項1に記載の方法。
- (c)前記式(II)のハロゲン化部分フッ素化化合物を(末端)炭化水素オレフィンと反応させて、前記ハロゲン化部分フッ素化化合物を伸長する工程、を更に含む、請求項1に記載の方法。
- 次の構造を有する化合物[Br−CF2−CFH−CF2−I、CF3−O−CFH−CF2−I、C3F7−O−CFH−CF2−Z、CF3−CF2−CF2−O−CF(CF3)−CF2−O−CFH−CF2−Z、I−(CF2)n−CFH−CF2−I、I−(CF2)m−CFH−CF2−Br、Br−(CF2)m−CFH−CF2−I、Br−(CF2)q−CFH−CF2−Br、CF3−O−(CF2)3−O−CFH−CF2−Z、Z−CF2−CFH−O−(CF2)n−O−CF=CF2、Z−CF2−CFH−O−(CF2)n−O−CFH−CF2−Z、Z−CF2−CFH−O−(CF2)n−O−CF2−CF=CF2、Z−CF2−CFH−O−(CF2)n−O−CF2−CFH−CF2−Z、CF2=CF−O−(CF2)n−O−CF2−CFH−CF2−Z、Z−CF2−CFH−CF2−O−(CF2)n−O−CF2−CF=CF2、Z−CF2−CFH−CF2−O−(CF2)n−O−CF2−CFH−CF2−Z、X’−CF2−CF2−O−(CF2)n−O−CF2CFH−CF2−Z、X’−CF2−CF2−O−CFH−CF2−Z、X’−CF2−CF2−O−CF2−CFH−CF2−Z、X’−CF(CF3)−CF2−O−CFH−CF2−Z、X’−CF(CF3)−CF2−O−CF2−CFH−CF2−Z、X’−CF2−CF2−(O−CF(CF3)−CF2)p−O−CFH−CF2−Z、X’−CF2−CF2−(O−CF(CF3)−CF2)p−O−CF2−CFH−CF2−Z、X’−CF2−CF2−CF2−O−CFH−CF2−Z、X’−CF2−CF2−CF2−O−CF2−CFH−CF2−Z、X’−CF2−CF2−CF2−(O−CF(CF3)−CF2)p−O−CFH−CF2−Z、X’−CF2−CF2−CF2−(O−CF(CF3)−CF2)p−O−CF2−CFH−CF2−Z、X’−CF2−CF2−O−(CF2)2−(O−CF(CF3)CF2)p−O−CFH−CF2−Z(式中、ZはBr、Iであり、X’はBr、I、C(O)X”、及びSO2X”から選択され、X”はF、Cl、OH、及びこれらの塩から選択され、mは1〜4の整数であり、nは2〜4の整数であり、pは1又は2であり、qは3又は4である。)]。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201462095300P | 2014-12-22 | 2014-12-22 | |
US62/095,300 | 2014-12-22 | ||
PCT/US2015/063947 WO2016105907A1 (en) | 2014-12-22 | 2015-12-04 | Methods of making halogenated partially fluorinated compounds |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2017538717A true JP2017538717A (ja) | 2017-12-28 |
JP2017538717A5 JP2017538717A5 (ja) | 2018-11-22 |
JP6758781B2 JP6758781B2 (ja) | 2020-09-23 |
Family
ID=56151391
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017531854A Expired - Fee Related JP6758781B2 (ja) | 2014-12-22 | 2015-12-04 | ハロゲン化部分フッ素化化合物の製造方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US10099982B2 (ja) |
EP (1) | EP3237367B1 (ja) |
JP (1) | JP6758781B2 (ja) |
CN (1) | CN107108421B (ja) |
RU (1) | RU2017121034A (ja) |
WO (1) | WO2016105907A1 (ja) |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1150665B (de) * | 1961-07-15 | 1963-06-27 | Hoechst Ag | Verfahren zur Herstellung von Fluorbromalkanen oder Fluorbromchloralkanen |
RU2064915C1 (ru) | 1993-12-14 | 1996-08-10 | Российский научный центр "Прикладная химия" | Способ получения йодфторалканов |
US5504248A (en) | 1994-07-28 | 1996-04-02 | E. I. Du Pont De Nemours And Company | Preparation of halogenated compounds |
JP4106520B2 (ja) * | 2001-12-19 | 2008-06-25 | ダイキン工業株式会社 | 含フッ素アルキルアイオダイドの製造方法 |
US7691282B2 (en) * | 2005-09-08 | 2010-04-06 | 3M Innovative Properties Company | Hydrofluoroether compounds and processes for their preparation and use |
EP2192100B1 (en) * | 2007-09-12 | 2016-02-24 | Unimatec Co., Ltd. | Terminally iodized polyfluoroalkane and method for producing the same |
GB0823120D0 (en) * | 2008-12-19 | 2009-01-28 | 3M Innovative Properties Co | Method of making fluorinated alkoxy carboxylic acids and precursors thereof |
WO2014062469A1 (en) * | 2012-10-18 | 2014-04-24 | 3M Innovative Properties Company | Fluoroiodo compounds for fluoropolymers |
-
2015
- 2015-12-04 CN CN201580070324.5A patent/CN107108421B/zh not_active Expired - Fee Related
- 2015-12-04 US US15/529,116 patent/US10099982B2/en active Active
- 2015-12-04 JP JP2017531854A patent/JP6758781B2/ja not_active Expired - Fee Related
- 2015-12-04 RU RU2017121034A patent/RU2017121034A/ru not_active Application Discontinuation
- 2015-12-04 WO PCT/US2015/063947 patent/WO2016105907A1/en active Application Filing
- 2015-12-04 EP EP15874088.6A patent/EP3237367B1/en active Active
Also Published As
Publication number | Publication date |
---|---|
US10099982B2 (en) | 2018-10-16 |
CN107108421A (zh) | 2017-08-29 |
RU2017121034A (ru) | 2019-01-25 |
EP3237367A1 (en) | 2017-11-01 |
WO2016105907A1 (en) | 2016-06-30 |
EP3237367A4 (en) | 2018-07-25 |
CN107108421B (zh) | 2021-04-27 |
JP6758781B2 (ja) | 2020-09-23 |
EP3237367B1 (en) | 2020-05-20 |
US20170283351A1 (en) | 2017-10-05 |
RU2017121034A3 (ja) | 2019-01-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US9353052B2 (en) | Fluorinated oligomers having pendant bromine-containing moieties | |
JP2014504293A (ja) | 高度フッ素化スルフィン酸のオリゴマー及びコオリゴマー並びにその塩類 | |
US9187416B2 (en) | Partially fluorinated sulfinic acid monomers and their salts | |
JP6758781B2 (ja) | ハロゲン化部分フッ素化化合物の製造方法 | |
JP2017226617A (ja) | 酸フルオリド及びパーフルオロアルキルビニルエーテルの製造方法 | |
JP2014528910A (ja) | 新規なフッ化不飽和化合物及び該化合物から得られるポリマー | |
JP2003522743A (ja) | 二重結合の官能化方法 | |
JP6860032B2 (ja) | パーフルオロアルキン化合物の製造方法 | |
JP2006335699A (ja) | モノマー中間体の製造方法 | |
JP2012171884A (ja) | 含水素フルオロジエン化合物の製造方法 | |
US10717693B2 (en) | Method for producing diol | |
JP7337759B2 (ja) | パーフルオロアルカジエン化合物の製造方法 | |
JP2508763B2 (ja) | フッ素含有カルボン酸エステルの製造方法 | |
JP2012131727A (ja) | 含フッ素ヨウ素化合物の製造方法 | |
JPWO2013084860A1 (ja) | ペンタフルオロスルファニル安息香酸の製造方法 | |
JP2018070601A (ja) | ハロゲン化合物の製造方法 | |
JP2017538717A5 (ja) | ||
JPH07179373A (ja) | 1−ブロモ−2−フルオロエタンの製造方法 | |
JPH0977702A (ja) | 新規な含フッ素オレフィンおよびその製造法 | |
JP2009040708A (ja) | 含フッ素カルボン酸類の製造方法 | |
JP2003221354A (ja) | 1−(tert−ブトキシフェニル)−ω−ハロアルカン | |
JP2001026570A (ja) | 含フッ素カルボン酸ビニルエステル | |
JPS6316379B2 (ja) | ||
JPS6310742A (ja) | 含フツ素脂肪族モノ及びジカルボン酸の製法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20181010 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20181010 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20190620 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20190625 |
|
RD03 | Notification of appointment of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7423 Effective date: 20190704 |
|
RD04 | Notification of resignation of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7424 Effective date: 20190709 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190919 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20200225 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20200525 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20200722 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20200804 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20200901 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6758781 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
LAPS | Cancellation because of no payment of annual fees |