JPS61122260A

JPS61122260A - 新規なペルフルオロジアルキルカルバモイルフルオリド及びその製造方法

新規なペルフルオロジアルキルカルバモイルフルオリド及びその製造方法

Info

Publication number: JPS61122260A
Authority: JP; Japan
Prior art keywords: fluoride; perfluoro; formula; perfluorodialkylcarbamoyl; methylamine
Prior art date: 1984-11-16
Legal status : Granted

Application number

JP24279284A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6156223B2 (enExample

Inventor

Takashi Abe

隆阿部

Eiji Hayashi

林　永二

Current Assignee

National Institute of Advanced Industrial Science and Technology AIST

Original Assignee

Agency of Industrial Science and Technology

Priority date

1984-11-16

Filing date

1984-11-16

Publication date

1986-06-10

1984-11-16 Application filed by Agency of Industrial Science and Technology filed Critical Agency of Industrial Science and Technology

1984-11-16 Priority to JP24279284A priority Critical patent/JPS61122260A/ja

1986-06-10 Publication of JPS61122260A publication Critical patent/JPS61122260A/ja

1986-12-01 Publication of JPS6156223B2 publication Critical patent/JPS6156223B2/ja

Status Granted legal-status Critical Current

Links

KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 title claims description 27
238000002360 preparation method Methods 0.000 title abstract 2
150000001875 compounds Chemical class 0.000 claims abstract description 9
HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims abstract description 7
-1 dialkylcarbamoyl fluoride Chemical compound 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 7
150000003512 tertiary amines Chemical class 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 abstract description 7
239000003054 catalyst Substances 0.000 abstract description 5
238000003682 fluorination reaction Methods 0.000 abstract description 5
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 abstract description 4
239000011737 fluorine Substances 0.000 abstract description 4
229910052731 fluorine Inorganic materials 0.000 abstract description 4
239000003905 agrochemical Substances 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 3
239000000975 dye Substances 0.000 abstract description 3
KMPITNDOTGKQSE-UHFFFAOYSA-N perfluoromethyldiethylamine Chemical compound FC(F)(F)C(F)(F)N(C(F)(F)F)C(F)(F)C(F)(F)F KMPITNDOTGKQSE-UHFFFAOYSA-N 0.000 abstract description 3
239000004094 surface-active agent Substances 0.000 abstract description 3
125000001931 aliphatic group Chemical group 0.000 abstract 1
238000010438 heat treatment Methods 0.000 abstract 1
239000000463 material Substances 0.000 abstract 1
VHDCQXZUGLTOHS-UHFFFAOYSA-N n,n-diethylcarbamoyl fluoride Chemical compound CCN(CC)C(F)=O VHDCQXZUGLTOHS-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
239000000047 product Substances 0.000 description 9
238000000034 method Methods 0.000 description 8
239000002994 raw material Substances 0.000 description 8
238000009835 boiling Methods 0.000 description 5
GICWIDZXWJGTCI-UHFFFAOYSA-I molybdenum pentachloride Chemical compound Cl[Mo](Cl)(Cl)(Cl)Cl GICWIDZXWJGTCI-UHFFFAOYSA-I 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
DHRZPDVVADNSCB-UHFFFAOYSA-N 1,1,2,2,3,3,3-heptafluoro-n,n-bis(trifluoromethyl)propan-1-amine Chemical compound FC(F)(F)N(C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)F DHRZPDVVADNSCB-UHFFFAOYSA-N 0.000 description 2
XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
PVXRCPDNJSFYBV-UHFFFAOYSA-N carbamoyl fluoride Chemical compound NC(F)=O PVXRCPDNJSFYBV-UHFFFAOYSA-N 0.000 description 2
IYRWEQXVUNLMAY-UHFFFAOYSA-N carbonyl fluoride Chemical group FC(F)=O IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
239000010931 gold Substances 0.000 description 2
229910052737 gold Inorganic materials 0.000 description 2
150000004812 organic fluorine compounds Chemical class 0.000 description 2
239000002904 solvent Substances 0.000 description 2
GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-N 0.000 description 1
CGYSGEFXYQMNJM-UHFFFAOYSA-N 1,1,2,2,2-pentafluoro-n,n-bis(trifluoromethyl)ethanamine Chemical compound FC(F)(F)N(C(F)(F)F)C(F)(F)C(F)(F)F CGYSGEFXYQMNJM-UHFFFAOYSA-N 0.000 description 1
QHIZNPLBQIHUJR-UHFFFAOYSA-N 1,1,2,2,3,3,3-heptafluoro-N-(1,1,2,2,3,3,3-heptafluoropropyl)-N-(trifluoromethyl)propan-1-amine Chemical compound FC(F)(F)N(C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)F QHIZNPLBQIHUJR-UHFFFAOYSA-N 0.000 description 1
CKWDXIIKKRRLCW-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluoro-N,N-bis(trifluoromethyl)butan-1-amine Chemical compound FC(F)(F)N(C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CKWDXIIKKRRLCW-UHFFFAOYSA-N 0.000 description 1
WHRDMJSLIKCSRL-UHFFFAOYSA-N 1,1-difluoro-n-(trifluoromethyl)methanimine Chemical compound FC(F)=NC(F)(F)F WHRDMJSLIKCSRL-UHFFFAOYSA-N 0.000 description 1
DOBUSJIVSSJEDA-UHFFFAOYSA-L 1,3-dioxa-2$l^{6}-thia-4-mercuracyclobutane 2,2-dioxide Chemical compound [Hg+2].[O-]S([O-])(=O)=O DOBUSJIVSSJEDA-UHFFFAOYSA-L 0.000 description 1
238000004293 19F NMR spectroscopy Methods 0.000 description 1
SYNPRNNJJLRHTI-UHFFFAOYSA-N 2-(hydroxymethyl)butane-1,4-diol Chemical compound OCCC(CO)CO SYNPRNNJJLRHTI-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical group F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
241000256011 Sphingidae Species 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000003708 ampul Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
230000000694 effects Effects 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229920001973 fluoroelastomer Polymers 0.000 description 1
NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
229940074994 mercuric sulfate Drugs 0.000 description 1
229910000372 mercury(II) sulfate Inorganic materials 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
CUIPDDJPSUECRB-UHFFFAOYSA-N n-methyl-n-propylbutan-1-amine Chemical compound CCCCN(C)CCC CUIPDDJPSUECRB-UHFFFAOYSA-N 0.000 description 1
GSLCHHWHMUKPDX-UHFFFAOYSA-N n-methyl-n-propylcarbamoyl fluoride Chemical compound CCCN(C)C(F)=O GSLCHHWHMUKPDX-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
125000005010 perfluoroalkyl group Chemical group 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000005297 pyrex Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1