JPH0559123B2 - - Google Patents
Info
- Publication number
- JPH0559123B2 JPH0559123B2 JP50180483A JP50180483A JPH0559123B2 JP H0559123 B2 JPH0559123 B2 JP H0559123B2 JP 50180483 A JP50180483 A JP 50180483A JP 50180483 A JP50180483 A JP 50180483A JP H0559123 B2 JPH0559123 B2 JP H0559123B2
- Authority
- JP
- Japan
- Prior art keywords
- dioxolane
- trifluoromethyl
- bis
- dioxole
- dichloro
- 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.)
- Expired - Lifetime
Links
- 238000004821 distillation Methods 0.000 description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000009835 boiling Methods 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 229920001577 copolymer Polymers 0.000 description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 13
- 229920001519 homopolymer Polymers 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- -1 and X' is H Inorganic materials 0.000 description 11
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 11
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical class C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 description 10
- IHFHXHCEXDIKMG-UHFFFAOYSA-N 4,4,5,5-tetrachloro-2,2-difluoro-1,3-dioxolane Chemical compound FC1(F)OC(Cl)(Cl)C(Cl)(Cl)O1 IHFHXHCEXDIKMG-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
- 235000011089 carbon dioxide Nutrition 0.000 description 9
- 238000006298 dechlorination reaction Methods 0.000 description 9
- 238000004817 gas chromatography Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 150000004862 dioxolanes Chemical class 0.000 description 8
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 7
- WKHOARALBWDJOC-UHFFFAOYSA-N 4-fluoro-2,2-bis(trifluoromethyl)-1,3-dioxole Chemical compound FC1=COC(C(F)(F)F)(C(F)(F)F)O1 WKHOARALBWDJOC-UHFFFAOYSA-N 0.000 description 7
- SNQXJPARXFUULZ-UHFFFAOYSA-N dioxolane Chemical class C1COOC1 SNQXJPARXFUULZ-UHFFFAOYSA-N 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 229910052749 magnesium Inorganic materials 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- YTHONYYQHMOSPD-UHFFFAOYSA-N 4,5-dichloro-2,2-difluoro-1,3-dioxolane Chemical compound FC1(F)OC(Cl)C(Cl)O1 YTHONYYQHMOSPD-UHFFFAOYSA-N 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 239000011630 iodine Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- MLTGZMHSEZRESX-UHFFFAOYSA-N 2,2,4-trifluoro-1,3-dioxole Chemical compound FC1=COC(F)(F)O1 MLTGZMHSEZRESX-UHFFFAOYSA-N 0.000 description 5
- CVPPQHSUWAKLPN-UHFFFAOYSA-N 4,4,5-trichloro-5-fluoro-2,2-bis(trifluoromethyl)-1,3-dioxolane Chemical compound FC(F)(F)C1(C(F)(F)F)OC(F)(Cl)C(Cl)(Cl)O1 CVPPQHSUWAKLPN-UHFFFAOYSA-N 0.000 description 5
- PCIFXCOMENTWDU-UHFFFAOYSA-N 4,5-dichloro-2,2,4-trifluoro-1,3-dioxolane Chemical compound FC1(F)OC(Cl)C(F)(Cl)O1 PCIFXCOMENTWDU-UHFFFAOYSA-N 0.000 description 5
- VBGNSWPPSZTBIY-UHFFFAOYSA-N 4-chloro-2,2-bis(trifluoromethyl)-1,3-dioxole Chemical compound FC(F)(F)C1(C(F)(F)F)OC=C(Cl)O1 VBGNSWPPSZTBIY-UHFFFAOYSA-N 0.000 description 5
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 229960002523 mercuric chloride Drugs 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 5
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 5
- 239000011592 zinc chloride Substances 0.000 description 5
- 235000005074 zinc chloride Nutrition 0.000 description 5
- JPLNAQJTXYXDAV-UHFFFAOYSA-N 4,4,5-trichloro-1,3-dioxolan-2-one Chemical compound ClC1OC(=O)OC1(Cl)Cl JPLNAQJTXYXDAV-UHFFFAOYSA-N 0.000 description 4
- NNQCMPWKGDDQEL-UHFFFAOYSA-N 4,4,5-trichloro-2,2,5-trifluoro-1,3-dioxolane Chemical compound FC1(F)OC(F)(Cl)C(Cl)(Cl)O1 NNQCMPWKGDDQEL-UHFFFAOYSA-N 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000012258 stirred mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- UWFOOHXUXMRPQQ-UHFFFAOYSA-N 2,2-bis(trifluoromethyl)-1,3-dioxole Chemical compound FC(F)(F)C1(C(F)(F)F)OC=CO1 UWFOOHXUXMRPQQ-UHFFFAOYSA-N 0.000 description 3
- BBDNRCSHYHULBK-UHFFFAOYSA-N 2,2-difluoro-1,3-dioxole Chemical compound FC1(F)OC=CO1 BBDNRCSHYHULBK-UHFFFAOYSA-N 0.000 description 3
- QIMFRZPDPFVAOT-UHFFFAOYSA-N 4,5-dichloro-2,2,4,5-tetrafluoro-1,3-dioxolane Chemical compound FC1(F)OC(F)(Cl)C(F)(Cl)O1 QIMFRZPDPFVAOT-UHFFFAOYSA-N 0.000 description 3
- SQZATTZYZHORKR-UHFFFAOYSA-N 4,5-dichloro-2,2-bis(trifluoromethyl)-1,3-dioxolane Chemical compound FC(F)(F)C1(C(F)(F)F)OC(Cl)C(Cl)O1 SQZATTZYZHORKR-UHFFFAOYSA-N 0.000 description 3
- SYLBJJIKMUZFRO-UHFFFAOYSA-N 4-chloro-5-fluoro-2,2-bis(trifluoromethyl)-1,3-dioxole Chemical compound FC1=C(Cl)OC(C(F)(F)F)(C(F)(F)F)O1 SYLBJJIKMUZFRO-UHFFFAOYSA-N 0.000 description 3
- 229910000497 Amalgam Inorganic materials 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 229940008718 metallic mercury Drugs 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 2
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 2
- HFNSTEOEZJBXIF-UHFFFAOYSA-N 2,2,4,5-tetrafluoro-1,3-dioxole Chemical compound FC1=C(F)OC(F)(F)O1 HFNSTEOEZJBXIF-UHFFFAOYSA-N 0.000 description 2
- PQNNUQKDERZMPQ-UHFFFAOYSA-N 2,2-bis(trifluoromethyl)-1,3-dioxolane Chemical compound FC(F)(F)C1(C(F)(F)F)OCCO1 PQNNUQKDERZMPQ-UHFFFAOYSA-N 0.000 description 2
- 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
- TXQPIYKVIOKFAB-UHFFFAOYSA-N 4,4,5,5-tetrachloro-1,3-dioxolan-2-one Chemical compound ClC1(Cl)OC(=O)OC1(Cl)Cl TXQPIYKVIOKFAB-UHFFFAOYSA-N 0.000 description 2
- RSNKMTZZWVFGES-UHFFFAOYSA-N 4,4,5,5-tetrachloro-2,2-bis(trifluoromethyl)-1,3-dioxolane Chemical compound FC(F)(F)C1(C(F)(F)F)OC(Cl)(Cl)C(Cl)(Cl)O1 RSNKMTZZWVFGES-UHFFFAOYSA-N 0.000 description 2
- BETICXVUVYXEJX-UHFFFAOYSA-N 4,5-Dichloro-1,3-dioxolan-2-one Chemical compound ClC1OC(=O)OC1Cl BETICXVUVYXEJX-UHFFFAOYSA-N 0.000 description 2
- GKMVELUKVFTOIL-UHFFFAOYSA-N 4,5-dichloro-2,2-bis(trifluoromethyl)-1,3-dioxole Chemical compound FC(F)(F)C1(C(F)(F)F)OC(Cl)=C(Cl)O1 GKMVELUKVFTOIL-UHFFFAOYSA-N 0.000 description 2
- LGSGGSYMPMQKQG-UHFFFAOYSA-N 4-chloro-2,2-difluoro-1,3-dioxole Chemical compound FC1(F)OC=C(Cl)O1 LGSGGSYMPMQKQG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- ORMNPSYMZOGSSV-UHFFFAOYSA-N dinitrooxymercury Chemical compound [Hg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ORMNPSYMZOGSSV-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910000856 hastalloy Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 150000002730 mercury Chemical class 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- NAMWHBVZXKMYJL-UHFFFAOYSA-N 2,2-dichloro-1,3-dioxolane Chemical class ClC1(Cl)OCCO1 NAMWHBVZXKMYJL-UHFFFAOYSA-N 0.000 description 1
- BYWCSUJYWJRIIY-UHFFFAOYSA-N 2-chloro-1,3-dioxolane Chemical compound ClC1OCCO1 BYWCSUJYWJRIIY-UHFFFAOYSA-N 0.000 description 1
- FEKJRSSKHNBSFT-UHFFFAOYSA-N 2-fluoro-1,3-dioxole Chemical compound FC1OC=CO1 FEKJRSSKHNBSFT-UHFFFAOYSA-N 0.000 description 1
- VEZYFJLULMBCCV-UHFFFAOYSA-N 4,4,5,5-tetrachloro-1,3-dioxolane Chemical class ClC1(Cl)OCOC1(Cl)Cl VEZYFJLULMBCCV-UHFFFAOYSA-N 0.000 description 1
- HYCPIMCKRSTQCQ-UHFFFAOYSA-N 4,4,5-trichloro-2,2-bis(trifluoromethyl)-1,3-dioxolane Chemical compound FC(F)(F)C1(C(F)(F)F)OC(Cl)C(Cl)(Cl)O1 HYCPIMCKRSTQCQ-UHFFFAOYSA-N 0.000 description 1
- MBYFPPFOTKUBQD-UHFFFAOYSA-N 4,4,5-trichloro-2,2-difluoro-1,3-dioxolane Chemical compound FC1(F)OC(Cl)C(Cl)(Cl)O1 MBYFPPFOTKUBQD-UHFFFAOYSA-N 0.000 description 1
- FSXIQVVWOCLXGI-UHFFFAOYSA-N 4,5-dichloro-1,3-dioxolane Chemical class ClC1OCOC1Cl FSXIQVVWOCLXGI-UHFFFAOYSA-N 0.000 description 1
- PQTSJAIWJYMBOX-UHFFFAOYSA-N 4,5-dichloro-4,5-difluoro-2,2-bis(trifluoromethyl)-1,3-dioxolane Chemical compound FC(F)(F)C1(C(F)(F)F)OC(F)(Cl)C(F)(Cl)O1 PQTSJAIWJYMBOX-UHFFFAOYSA-N 0.000 description 1
- JDVFUAXVBAFSKH-UHFFFAOYSA-N 4,5-difluoro-1,3-dioxole Chemical compound FC1=C(F)OCO1 JDVFUAXVBAFSKH-UHFFFAOYSA-N 0.000 description 1
- OYOKPDLAMOMTEE-UHFFFAOYSA-N 4-chloro-1,3-dioxolan-2-one Chemical compound ClC1COC(=O)O1 OYOKPDLAMOMTEE-UHFFFAOYSA-N 0.000 description 1
- JLIHYCHHJICNSS-UHFFFAOYSA-N 4-chloro-2,2,5-trifluoro-1,3-dioxolane Chemical compound FC1OC(F)(F)OC1Cl JLIHYCHHJICNSS-UHFFFAOYSA-N 0.000 description 1
- LLLDLQNCQASROM-UHFFFAOYSA-N 4-chloro-2,2,5-trifluoro-1,3-dioxole Chemical compound FC1=C(Cl)OC(F)(F)O1 LLLDLQNCQASROM-UHFFFAOYSA-N 0.000 description 1
- GNLPFSPLJQKLPU-UHFFFAOYSA-N 4-chloro-5-fluoro-1,3-dioxole Chemical compound ClC=1OCOC=1F GNLPFSPLJQKLPU-UHFFFAOYSA-N 0.000 description 1
- 229920001774 Perfluoroether Polymers 0.000 description 1
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 1
- 229920006127 amorphous resin Polymers 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000000382 dechlorinating effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical compound FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 1
- RVZRBWKZFJCCIB-UHFFFAOYSA-N perfluorotributylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RVZRBWKZFJCCIB-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 229940038570 terrell Drugs 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US375468DEEDK | 1982-05-06 | ||
| PCT/US1983/000569 WO1983004032A1 (en) | 1982-05-06 | 1983-04-20 | Novel fluorodioxoles and fluorodioxole polymers |
Related Child Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2412116A Division JPH0735378B2 (ja) | 1982-05-06 | 1990-12-19 | 新規なフルオロジオキソール類およびその製造方法 |
| JP4054146A Division JPH066630B2 (ja) | 1982-05-06 | 1992-02-06 | フルオロジオキソールのポリマーの自己支持性フイルム |
| JP4229367A Division JPH05331239A (ja) | 1982-05-06 | 1992-08-05 | フルオロジオキソールのコポリマーまたはターポリマー |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59500769A JPS59500769A (ja) | 1984-05-04 |
| JPH0559123B2 true JPH0559123B2 (it) | 1993-08-30 |
Family
ID=22175023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50180483A Granted JPS59500769A (ja) | 1982-05-06 | 1983-04-20 | 新規なフルオロジオキソ−ル類およびフルオロジオキソ−ルのポリマ−類 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59500769A (it) |
-
1983
- 1983-04-20 JP JP50180483A patent/JPS59500769A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59500769A (ja) | 1984-05-04 |
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