JP4836352B2 - 非プロトン性溶媒中での過酸化ジアシルの合成 - Google Patents
非プロトン性溶媒中での過酸化ジアシルの合成 Download PDFInfo
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- JP4836352B2 JP4836352B2 JP2001157553A JP2001157553A JP4836352B2 JP 4836352 B2 JP4836352 B2 JP 4836352B2 JP 2001157553 A JP2001157553 A JP 2001157553A JP 2001157553 A JP2001157553 A JP 2001157553A JP 4836352 B2 JP4836352 B2 JP 4836352B2
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- peroxide
- diacyl
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- organic
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- 239000012933 diacyl peroxide Substances 0.000 title claims description 93
- 230000015572 biosynthetic process Effects 0.000 title claims description 53
- 238000003786 synthesis reaction Methods 0.000 title claims description 48
- 239000000010 aprotic solvent Substances 0.000 title claims description 33
- 150000002978 peroxides Chemical class 0.000 claims description 88
- 238000000034 method Methods 0.000 claims description 55
- 150000001266 acyl halides Chemical class 0.000 claims description 50
- 238000006243 chemical reaction Methods 0.000 claims description 49
- -1 halocarbon ethers Chemical class 0.000 claims description 47
- 239000000047 product Substances 0.000 claims description 41
- 239000002904 solvent Substances 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 18
- 150000008282 halocarbons Chemical class 0.000 claims description 9
- 150000001451 organic peroxides Chemical class 0.000 claims description 7
- 239000003463 adsorbent Substances 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 75
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 63
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 229910002092 carbon dioxide Inorganic materials 0.000 description 32
- 239000001569 carbon dioxide Substances 0.000 description 29
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 26
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 26
- 239000004202 carbamide Substances 0.000 description 26
- 239000002253 acid Substances 0.000 description 25
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 25
- 238000006116 polymerization reaction Methods 0.000 description 22
- VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 description 19
- 229940045872 sodium percarbonate Drugs 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- 239000007788 liquid Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 14
- 238000012546 transfer Methods 0.000 description 11
- 239000003999 initiator Substances 0.000 description 10
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 10
- 229910001220 stainless steel Inorganic materials 0.000 description 10
- 239000010935 stainless steel Substances 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 9
- 150000002430 hydrocarbons Chemical group 0.000 description 9
- 238000004448 titration Methods 0.000 description 9
- 239000004215 Carbon black (E152) Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 229960001922 sodium perborate Drugs 0.000 description 8
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 8
- 239000002131 composite material Substances 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 235000011089 carbon dioxide Nutrition 0.000 description 5
- 239000011491 glass wool Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 150000004965 peroxy acids Chemical class 0.000 description 5
- 239000007790 solid phase Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000005303 weighing Methods 0.000 description 5
- RPBWMJBZQXCSFW-UHFFFAOYSA-N 2-methylpropanoyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(=O)C(C)C RPBWMJBZQXCSFW-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000010924 continuous production Methods 0.000 description 4
- 125000001033 ether group Chemical group 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910021645 metal ion Inorganic materials 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000012418 sodium perborate tetrahydrate Substances 0.000 description 4
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 4
- IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- AVIPLHGOOORCDN-UHFFFAOYSA-N (2,2-difluoro-2-fluorosulfonylacetyl) 2,2-difluoro-2-fluorosulfonylethaneperoxoate Chemical compound FS(=O)(=O)C(F)(F)C(=O)OOC(=O)C(F)(F)S(F)(=O)=O AVIPLHGOOORCDN-UHFFFAOYSA-N 0.000 description 3
- PYSYKOPZHYNYSZ-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)-3-(1,2,2,2-tetrafluoroethoxy)propane Chemical compound FC(F)(F)C(F)OC(F)(F)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)C(F)(F)F PYSYKOPZHYNYSZ-UHFFFAOYSA-N 0.000 description 3
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 3
- SGNZYJXNUURYCH-UHFFFAOYSA-N 5,6-dihydroxyindole Chemical compound C1=C(O)C(O)=CC2=C1NC=C2 SGNZYJXNUURYCH-UHFFFAOYSA-N 0.000 description 3
- XSVSPKKXQGNHMD-UHFFFAOYSA-N 5-bromo-3-methyl-1,2-thiazole Chemical compound CC=1C=C(Br)SN=1 XSVSPKKXQGNHMD-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 150000001265 acyl fluorides Chemical class 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 229940093915 gynecological organic acid Drugs 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 150000002484 inorganic compounds Chemical class 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 3
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- JUTIIYKOQPDNEV-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluorobutanoyl 2,2,3,3,4,4,4-heptafluorobutaneperoxoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(=O)OOC(=O)C(F)(F)C(F)(F)C(F)(F)F JUTIIYKOQPDNEV-UHFFFAOYSA-N 0.000 description 2
- BCLQALQSEBVVAD-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propanoyl fluoride Chemical compound FC(=O)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)C(F)(F)F BCLQALQSEBVVAD-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229910005143 FSO2 Inorganic materials 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910006095 SO2F Inorganic materials 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- GUBGYTABKSRVRQ-ASMJPISFSA-N alpha-maltose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-ASMJPISFSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 229920002313 fluoropolymer Polymers 0.000 description 2
- 239000004811 fluoropolymer Substances 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- GVGCUCJTUSOZKP-UHFFFAOYSA-N nitrogen trifluoride Chemical group FN(F)F GVGCUCJTUSOZKP-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical group 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 150000004684 trihydrates Chemical group 0.000 description 2
- RIQRGMUSBYGDBL-UHFFFAOYSA-N 1,1,1,2,2,3,4,5,5,5-decafluoropentane Chemical compound FC(F)(F)C(F)C(F)C(F)(F)C(F)(F)F RIQRGMUSBYGDBL-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- YIHXQSQQJBEAKK-UHFFFAOYSA-N 2,2-difluoro-2-fluorosulfonylacetyl fluoride Chemical compound FC(=O)C(F)(F)S(F)(=O)=O YIHXQSQQJBEAKK-UHFFFAOYSA-N 0.000 description 1
- PYIMQPQWCZJYNU-UHFFFAOYSA-N 2-propoxypropanoyl fluoride Chemical compound CCCOC(C)C(F)=O PYIMQPQWCZJYNU-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000012425 OXONE® Substances 0.000 description 1
- 229920001774 Perfluoroether Polymers 0.000 description 1
- 241001315609 Pittosporum crassifolium Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229940095564 anhydrous calcium sulfate Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000010945 base-catalyzed hydrolysis reactiony Methods 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- HJKYXKSLRZKNSI-UHFFFAOYSA-I pentapotassium;hydrogen sulfate;oxido sulfate;sulfuric acid Chemical compound [K+].[K+].[K+].[K+].[K+].OS([O-])(=O)=O.[O-]S([O-])(=O)=O.OS(=O)(=O)O[O-].OS(=O)(=O)O[O-] HJKYXKSLRZKNSI-UHFFFAOYSA-I 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- LMFJKKGDLAICPF-UHFFFAOYSA-N phenanthrene-9-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC3=CC=CC=C3C2=C1 LMFJKKGDLAICPF-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical group FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229940045136 urea Drugs 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20700500P | 2000-05-25 | 2000-05-25 | |
| US60/207005 | 2000-05-25 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002003469A JP2002003469A (ja) | 2002-01-09 |
| JP2002003469A5 JP2002003469A5 (enExample) | 2008-07-03 |
| JP4836352B2 true JP4836352B2 (ja) | 2011-12-14 |
Family
ID=22768821
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001157553A Expired - Fee Related JP4836352B2 (ja) | 2000-05-25 | 2001-05-25 | 非プロトン性溶媒中での過酸化ジアシルの合成 |
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| Country | Link |
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| US (2) | US20020026011A1 (enExample) |
| EP (1) | EP1164130B1 (enExample) |
| JP (1) | JP4836352B2 (enExample) |
| CN (1) | CN1239481C (enExample) |
| DE (1) | DE60108556T2 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6395937B2 (en) * | 2000-05-25 | 2002-05-28 | E.I. Du Pont De Nemours And Company | Synthesis of diacyl peroxide in carbon dioxide |
| RU2241700C2 (ru) * | 2002-03-07 | 2004-12-10 | Открытое акционерное общество "Кирово-Чепецкий химический комбинат им. Б.П. Константинова" | Способ получения перфтор-2-метил-3-оксагексаноилпероксида |
| RU2213730C1 (ru) * | 2002-03-07 | 2003-10-10 | Открытое акционерное общество "Кирово-Чепецкий химический комбинат им. Б.П. Константинова" | Способ получения перфтор-2-метил-3-оксагексаноилпероксида |
| CA2651957A1 (en) * | 2006-05-15 | 2007-11-22 | Virginia Commonwealth University | Methods and compositions for controlled and sustained production and delivery of peroxides and/or oxygen for biological and industrial applications |
| JP5724874B2 (ja) * | 2009-04-08 | 2015-05-27 | 旭硝子株式会社 | ペルフルオロ有機過酸化物の製造方法 |
| CN108794367A (zh) * | 2017-05-04 | 2018-11-13 | 中国科学院上海有机化学研究所 | 全氟酰基过氧化物的制备 |
| KR101946249B1 (ko) | 2018-03-06 | 2019-02-11 | 아주대학교산학협력단 | 대칭형 폴리올레핀 블록 공중합체 및 이의 제조 방법 |
| CN113260639A (zh) * | 2018-12-20 | 2021-08-13 | 索尔维特殊聚合物意大利有限公司 | 用于制备全卤酰基过氧化物的方法 |
| HUE063678T2 (hu) | 2019-06-12 | 2024-01-28 | Nouryon Chemicals Int Bv | Eljárás peroxiészterek elõállítására |
| WO2020249691A1 (en) | 2019-06-12 | 2020-12-17 | Nouryon Chemicals International B.V. | Process for the production of diacyl peroxides |
| WO2020249690A1 (en) | 2019-06-12 | 2020-12-17 | Nouryon Chemicals International B.V. | Process for the production of diacyl peroxides |
| CN114127045B (zh) * | 2019-06-12 | 2023-10-13 | 诺力昂化学品国际有限公司 | 用于生产过氧化二酰的方法 |
| ES2963357T3 (es) | 2019-06-12 | 2024-03-26 | Nouryon Chemicals Int Bv | Proceso para la producción de peróxidos de diacilo |
| US11905350B2 (en) | 2019-09-09 | 2024-02-20 | Compact Membrane Systems, Inc. | Gas permeable fluoropolymers and ionomers |
| CN116730890A (zh) * | 2022-03-02 | 2023-09-12 | 西湖大学 | 一种光学活性三氟甲磺酰基过氧化物衍生物及其制备方法 |
| CN120923395A (zh) * | 2025-10-14 | 2025-11-11 | 淄博正华助剂股份有限公司 | 含有羰基的过氧化物的制备方法及应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2792423A (en) * | 1951-05-17 | 1957-05-14 | Union Carbide & Carbon Corp | Production of bis (perfluoroacyl) peroxides |
| US3860568A (en) * | 1966-05-13 | 1975-01-14 | Rhone Poulenc Sa | Novel polymerization initiator and process for polymerization using the same |
| US3502701A (en) * | 1967-05-18 | 1970-03-24 | Argus Chem | Unsymmetrical diacyl peroxides |
| US3936506A (en) * | 1971-10-29 | 1976-02-03 | Union Carbide Corporation | Preparation of unsymmetrical halogen-substituted diacyl peroxides |
| JPS61152653A (ja) | 1984-12-26 | 1986-07-11 | Daikin Ind Ltd | 含フツ素ジアシルパ−オキサイドおよびその用途 |
| FR2604435B1 (fr) * | 1986-09-30 | 1988-12-02 | Oreal | Peroxydes aromatiques insatures et leur utilisation en therapeutique et cosmetique |
| US5021516A (en) | 1989-06-26 | 1991-06-04 | E. I. Du Pont De Nemours And Company | Poly(perfluoroether)acyl peroxides |
| US5820841A (en) | 1996-09-19 | 1998-10-13 | Ethicon, Inc. | Hydrogen peroxide complexes of inorganic salts and synthesis thereof |
| US6395937B2 (en) * | 2000-05-25 | 2002-05-28 | E.I. Du Pont De Nemours And Company | Synthesis of diacyl peroxide in carbon dioxide |
-
2001
- 2001-05-07 US US09/850,546 patent/US20020026011A1/en not_active Abandoned
- 2001-05-21 EP EP01304444A patent/EP1164130B1/en not_active Expired - Lifetime
- 2001-05-21 DE DE60108556T patent/DE60108556T2/de not_active Expired - Lifetime
- 2001-05-25 CN CN01122073.2A patent/CN1239481C/zh not_active Expired - Fee Related
- 2001-05-25 JP JP2001157553A patent/JP4836352B2/ja not_active Expired - Fee Related
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2004
- 2004-05-14 US US10/846,793 patent/US7112314B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1164130A3 (en) | 2002-04-17 |
| DE60108556T2 (de) | 2006-01-12 |
| US20040213723A1 (en) | 2004-10-28 |
| CN1342647A (zh) | 2002-04-03 |
| JP2002003469A (ja) | 2002-01-09 |
| EP1164130B1 (en) | 2005-01-26 |
| US20020026011A1 (en) | 2002-02-28 |
| EP1164130A2 (en) | 2001-12-19 |
| US7112314B2 (en) | 2006-09-26 |
| CN1239481C (zh) | 2006-02-01 |
| DE60108556D1 (de) | 2005-03-03 |
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