EA002422B1 - Способ разложения гидропероксида - Google Patents
Способ разложения гидропероксида Download PDFInfo
- Publication number
- EA002422B1 EA002422B1 EA199900737A EA199900737A EA002422B1 EA 002422 B1 EA002422 B1 EA 002422B1 EA 199900737 A EA199900737 A EA 199900737A EA 199900737 A EA199900737 A EA 199900737A EA 002422 B1 EA002422 B1 EA 002422B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- solution
- process according
- catalyst
- gold
- chhp
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 70
- 238000000354 decomposition reaction Methods 0.000 title claims abstract description 48
- 230000008569 process Effects 0.000 title claims abstract description 31
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 title claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 81
- 239000010931 gold Substances 0.000 claims abstract description 68
- 229910052737 gold Inorganic materials 0.000 claims abstract description 55
- 239000003054 catalyst Substances 0.000 claims abstract description 48
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims abstract description 26
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims abstract description 19
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 15
- 230000003197 catalytic effect Effects 0.000 claims abstract description 9
- 239000011541 reaction mixture Substances 0.000 claims abstract description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000002576 ketones Chemical class 0.000 claims abstract description 6
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 229910052709 silver Inorganic materials 0.000 claims abstract description 4
- 239000004332 silver Substances 0.000 claims abstract description 4
- FYLJKQFMQFOLSZ-UHFFFAOYSA-N cyclohexylperoxycyclohexane Chemical compound C1CCCCC1OOC1CCCCC1 FYLJKQFMQFOLSZ-UHFFFAOYSA-N 0.000 claims abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 239000001301 oxygen Substances 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 20
- 239000002638 heterogeneous catalyst Substances 0.000 claims description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical group O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 1
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical group OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 abstract description 63
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 23
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical group [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract description 13
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 abstract description 10
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract description 10
- 239000000377 silicon dioxide Substances 0.000 abstract description 9
- 230000006872 improvement Effects 0.000 abstract description 5
- 229910052681 coesite Inorganic materials 0.000 abstract 1
- 229910052906 cristobalite Inorganic materials 0.000 abstract 1
- 235000012239 silicon dioxide Nutrition 0.000 abstract 1
- 229910052682 stishovite Inorganic materials 0.000 abstract 1
- 229910052905 tridymite Inorganic materials 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 87
- 238000002474 experimental method Methods 0.000 description 45
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 239000000126 substance Substances 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- PBKONEOXTCPAFI-UHFFFAOYSA-N TCB Natural products ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 17
- 239000011651 chromium Substances 0.000 description 16
- 239000000725 suspension Substances 0.000 description 16
- 239000007787 solid Substances 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 14
- 239000012298 atmosphere Substances 0.000 description 13
- FVQGNKROUPZXBL-UHFFFAOYSA-L chromium(2+);acetate;hydroxide Chemical compound [OH-].[Cr+2].CC([O-])=O FVQGNKROUPZXBL-UHFFFAOYSA-L 0.000 description 13
- 239000000499 gel Substances 0.000 description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 229910003803 Gold(III) chloride Inorganic materials 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- RJHLTVSLYWWTEF-UHFFFAOYSA-K gold trichloride Chemical compound Cl[Au](Cl)Cl RJHLTVSLYWWTEF-UHFFFAOYSA-K 0.000 description 10
- 229940076131 gold trichloride Drugs 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- 239000003708 ampul Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 239000001307 helium Substances 0.000 description 6
- 229910052734 helium Inorganic materials 0.000 description 6
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 6
- 229960005336 magnesium citrate Drugs 0.000 description 6
- 239000004337 magnesium citrate Substances 0.000 description 6
- 235000002538 magnesium citrate Nutrition 0.000 description 6
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 239000001509 sodium citrate Substances 0.000 description 6
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 6
- 239000012265 solid product Substances 0.000 description 6
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 6
- PLSARIKBYIPYPF-UHFFFAOYSA-H trimagnesium dicitrate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O PLSARIKBYIPYPF-UHFFFAOYSA-H 0.000 description 6
- 229910052726 zirconium Inorganic materials 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000001879 gelation Methods 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 239000011148 porous material Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- 229910052719 titanium Inorganic materials 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000000395 magnesium oxide Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000004408 titanium dioxide Substances 0.000 description 4
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 3
- -1 aromatic hydroperoxides Chemical class 0.000 description 3
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 3
- 238000009776 industrial production Methods 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000470755 Aistus Species 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 229910000906 Bronze Inorganic materials 0.000 description 1
- KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical compound COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-UHFFFAOYSA-N 0.000 description 1
- 229910020599 Co 3 O 4 Inorganic materials 0.000 description 1
- 229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 1
- 102100021009 Cytochrome b-c1 complex subunit Rieske, mitochondrial Human genes 0.000 description 1
- 108050007001 Cytochrome b6-f complex iron-sulfur subunit Proteins 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000010974 bronze Substances 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000003421 catalytic decomposition reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000011208 chromatographic data Methods 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- MJBAMTOPQZQBAK-UHFFFAOYSA-N chromium(3+);pentane-2,4-dione Chemical compound [Cr+3].CC(=O)CC(C)=O MJBAMTOPQZQBAK-UHFFFAOYSA-N 0.000 description 1
- MJSNUBOCVAKFIJ-LNTINUHCSA-N chromium;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Cr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MJSNUBOCVAKFIJ-LNTINUHCSA-N 0.000 description 1
- XEHUIDSUOAGHBW-UHFFFAOYSA-N chromium;pentane-2,4-dione Chemical compound [Cr].CC(=O)CC(C)=O.CC(=O)CC(C)=O.CC(=O)CC(C)=O XEHUIDSUOAGHBW-UHFFFAOYSA-N 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- QAEKNCDIHIGLFI-UHFFFAOYSA-L cobalt(2+);2-ethylhexanoate Chemical compound [Co+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O QAEKNCDIHIGLFI-UHFFFAOYSA-L 0.000 description 1
- 238000001246 colloidal dispersion Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- WLPSNBGDESCKIL-UHFFFAOYSA-N ethanol;titanium Chemical compound [Ti].CCO WLPSNBGDESCKIL-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002432 hydroperoxides Chemical group 0.000 description 1
- GPHZOCJETVZYTP-UHFFFAOYSA-N hydroperoxycyclododecane Chemical compound OOC1CCCCCCCCCCC1 GPHZOCJETVZYTP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000006651 lactation Effects 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- QLNWXBAGRTUKKI-UHFFFAOYSA-N metacetamol Chemical compound CC(=O)NC1=CC=CC(O)=C1 QLNWXBAGRTUKKI-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- BSMBZDDPUMOQPJ-UHFFFAOYSA-N n-pyridin-2-yl-3-pyridin-2-yliminoisoindol-1-amine Chemical class C=1C=CC=NC=1NC(C1=CC=CC=C11)=NC1=NC1=CC=CC=N1 BSMBZDDPUMOQPJ-UHFFFAOYSA-N 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- ZSGPXUGYQIQEOF-UHFFFAOYSA-H trimagnesium;2-hydroxypropane-1,2,3-tricarboxylate;pentahydrate Chemical compound O.O.O.O.O.[Mg+2].[Mg+2].[Mg+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O ZSGPXUGYQIQEOF-UHFFFAOYSA-H 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3756497P | 1997-02-11 | 1997-02-11 | |
| US4516597P | 1997-04-30 | 1997-04-30 | |
| PCT/US1998/002926 WO1998034894A2 (en) | 1997-02-11 | 1998-02-10 | Hydroperoxide decomposition process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA199900737A1 EA199900737A1 (ru) | 2000-02-28 |
| EA002422B1 true EA002422B1 (ru) | 2002-04-25 |
Family
ID=26714254
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA199900737A EA002422B1 (ru) | 1997-02-11 | 1998-02-10 | Способ разложения гидропероксида |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6284927B1 (enExample) |
| EP (1) | EP1012130B9 (enExample) |
| JP (1) | JP3976793B2 (enExample) |
| KR (1) | KR20000070969A (enExample) |
| CN (1) | CN1102923C (enExample) |
| AU (1) | AU6167498A (enExample) |
| BR (1) | BR9815441B1 (enExample) |
| CA (1) | CA2279493A1 (enExample) |
| CZ (1) | CZ295000B6 (enExample) |
| DE (1) | DE69810944T2 (enExample) |
| EA (1) | EA002422B1 (enExample) |
| ID (1) | ID22219A (enExample) |
| PL (1) | PL336762A1 (enExample) |
| SK (1) | SK105899A3 (enExample) |
| WO (1) | WO1998034894A2 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6160183A (en) * | 1998-02-10 | 2000-12-12 | E. I. Du Pont De Nemours And Company | Direct oxidation of cycloalkanes |
| JP2002523488A (ja) * | 1998-08-26 | 2002-07-30 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ヒドロパーオキサイド分解方法 |
| KR20020018999A (ko) * | 1999-03-10 | 2002-03-09 | 메리 이. 보울러 | 히드로퍼옥시드 분해 방법 |
| US6169215B1 (en) * | 1999-03-25 | 2001-01-02 | Mobil Oil Corporation | Production of phenol |
| US6806390B1 (en) | 2000-08-18 | 2004-10-19 | Inuista North America S.àr.l. | Hydroperoxide decomposition catalyst |
| FR2823745A1 (fr) * | 2001-04-20 | 2002-10-25 | Rhodia Polyamide Intermediates | Procede de decomposition catalytique des hydroperoxydes organiques |
| US6984761B2 (en) * | 2002-12-16 | 2006-01-10 | Exxonmobil Chemical Patents Inc. | Co-production of phenol, acetone, α-methylstyrene and propylene oxide, and catalyst therefor |
| US7081552B2 (en) * | 2004-08-17 | 2006-07-25 | Solutia Inc. | Catalysts for cycloalkanes oxidation and decomposition of cycloalkyl hydroperoxide |
| CN100364663C (zh) * | 2006-04-07 | 2008-01-30 | 浙江大学 | 负载型纳米金催化剂及制备方法 |
| US8026398B2 (en) * | 2006-05-16 | 2011-09-27 | Narayana Mysore | Catalysts comprising a combination of oxidized metals and a method for cleaving phenylalkyl hydroperoxides using the catalysts |
| US7417003B2 (en) * | 2006-12-29 | 2008-08-26 | Uop Llc | Solid acid catalyst and process for decomposition of cumene hydroperoxide |
| JP4955440B2 (ja) * | 2007-03-29 | 2012-06-20 | Ｊｘ日鉱日石エネルギー株式会社 | ジヒドロキシ芳香族化合物の製造方法 |
| CN102177121B (zh) * | 2008-10-10 | 2015-05-13 | 埃克森美孚化学专利公司 | 生产苯酚的方法 |
| JP5486010B2 (ja) * | 2008-10-10 | 2014-05-07 | エクソンモービル・ケミカル・パテンツ・インク | フェノールの製造方法 |
| WO2010098916A2 (en) | 2009-02-26 | 2010-09-02 | Exxonmobil Chemical Patents Inc. | Process for producing phenol |
| US9061974B2 (en) | 2010-01-25 | 2015-06-23 | Exxonmobil Chemical Patents Inc. | Process for producing phenol |
| US9321710B2 (en) | 2010-01-25 | 2016-04-26 | Exxonmobil Chemical Patents Inc. | Process for producing phenol |
| WO2012036824A1 (en) | 2010-09-14 | 2012-03-22 | Exxonmobil Chemical Patents Inc. | Oxidation of alkylbenzenes and cycloalkylbenzenes |
| CN102161526B (zh) * | 2011-03-04 | 2012-12-12 | 北京化工大学 | 氧化镁负载钴铁金属磁性纳米材料在降解废水中橙黄ⅱ的应用 |
| US9388102B2 (en) | 2011-04-19 | 2016-07-12 | Exxonmobil Chemical Patents Inc. | Process for producing phenol |
| WO2013052217A2 (en) | 2011-10-07 | 2013-04-11 | Exxonmobil Chemical Patents Inc. | Mixed metal oxide catalysts and use thereof |
| CN104326870A (zh) * | 2014-09-16 | 2015-02-04 | 上海洪鲁化工技术有限公司 | 一种环己基过氧化氢的加氢分解方法 |
| JP6628800B2 (ja) * | 2014-11-28 | 2020-01-15 | ロディア オペレーションズＲｈｏｄｉａ Ｏｐｅｒａｔｉｏｎｓ | アルコール及び／又はケトンの製造方法 |
| CN106268847A (zh) * | 2015-06-08 | 2017-01-04 | 中国石油化工股份有限公司 | 一种环己烷氧化液分解催化剂的制备及分解工艺 |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2851496A (en) * | 1954-07-27 | 1958-09-09 | Du Pont | Preparation of oxidation products of cyclohexane |
| GB1333129A (en) * | 1970-12-30 | 1973-10-10 | Shell Int Research | Process for the decomposition of organic peroxy compounds |
| US3941845A (en) * | 1972-10-21 | 1976-03-02 | Stamicarbon, B.V. | Process for preparing cycloalkanones and cycloalkanols |
| EP0453021A1 (en) * | 1990-04-14 | 1991-10-23 | Dsm N.V. | Process for preparing a cycloalkanone and/or cycloalkanol |
| WO1992016487A1 (en) * | 1991-03-25 | 1992-10-01 | Dsm N.V. | Process for preparing an alkanone and/or alkanol |
| WO1994008932A1 (en) * | 1992-10-09 | 1994-04-28 | Technische Universiteit Delft | Method for the catalyzed decomposition of organic hydroperoxides |
| EP0659726A1 (en) * | 1993-12-23 | 1995-06-28 | Dsm N.V. | Process for preparing an alkanone and/or an alkanol |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3093686A (en) | 1963-06-11 | Production of cyclic alcohols | ||
| US2609395A (en) | 1949-12-16 | 1952-09-02 | Phillips Petroleum Co | Oxidation of hydrocarbons |
| US2675407A (en) | 1952-04-10 | 1954-04-13 | Standard Oil Dev Co | Air oxidation of cycloalkanes |
| US2854487A (en) * | 1955-04-12 | 1958-09-30 | Distillers Co Yeast Ltd | Process for the manufacture of carbinols |
| US3530185A (en) | 1966-08-08 | 1970-09-22 | Du Pont | Oxidation process |
| FR1547427A (fr) | 1967-05-26 | 1968-11-29 | Rhone Poulenc Sa | Perfectionnement à la préparation de mélanges cycloalcanols/cycloalcanones |
| US3598869A (en) | 1967-12-05 | 1971-08-10 | Celanese Corp | Oxidation of cyclohexane to nylon precursors |
| US3927105A (en) | 1968-04-08 | 1975-12-16 | Rhone Poulenc Sa | Process for the preparation of mixtures of cycloalkanols and cycloalkanones |
| FR2087365A5 (enExample) | 1970-05-15 | 1971-12-31 | Rhone Poulenc Sa | |
| GB1347913A (en) | 1970-06-09 | 1974-02-27 | Basf Ag | Production of cycloalkanols and cycloalkanones |
| US3957876A (en) | 1970-07-31 | 1976-05-18 | E. I. Du Pont De Nemours And Company | Process for the oxidation of cyclohexane |
| NL174343C (nl) | 1973-10-09 | 1984-06-01 | Stamicarbon | Werkwijze voor het bereiden van cycloalkanonen en cycloalkanolen door omzetting van een cycloalkylhydroperoxide. |
| US3987100A (en) | 1974-04-11 | 1976-10-19 | E. I. Du Pont De Nemours And Company | Cyclohexane oxidation in the presence of binary catalysts |
| GB1502767A (en) | 1974-05-06 | 1978-03-01 | Burmah Oil Trading Ltd | Production of phenols |
| US4326084A (en) | 1979-10-11 | 1982-04-20 | E. I. Du Pont De Nemours And Company | Process for producing a mixture containing cyclohexanol and cyclohexanone from cyclohexane |
| GB8303574D0 (en) * | 1983-02-09 | 1983-03-16 | Ici Plc | Hydrocarbon conversion processes |
| US4503257A (en) | 1983-05-18 | 1985-03-05 | E. I. Du Pont De Nemours And Company | Cyclohexyl hydroperoxide decomposition process |
| US4783557A (en) | 1986-09-12 | 1988-11-08 | Mitsui Petrochemical Industries, Ltd. | Processes for preparing hydroxynaphthalenes |
| NL8802592A (nl) | 1988-10-21 | 1990-05-16 | Stamicarbon | Werkwijze voor de bereiding van een k/a-mengsel. |
| US5023383A (en) | 1989-01-13 | 1991-06-11 | Mitsubishi Petrochemical Co., Ltd. | Method for producing aromatic alcohol |
| US5399794A (en) | 1993-11-12 | 1995-03-21 | Texaco Chemical Inc. | Use of supported palladium/gold catalysts in the preparation of tertiary butyl alcohol from tertiary butyl hydroperoxide |
| US5414163A (en) | 1993-11-12 | 1995-05-09 | Texaco Chemical Inc. | Use of titania or zirconia in the preparation of tertiary butyl alcohol from tertiary butyl hydroperoxide |
| US5414141A (en) | 1993-11-12 | 1995-05-09 | Texaco Chemical Inc. | Use of supported palladium catalysts in the preparation of tertiary butyl alcohol from tertiary butyl hydroperoxide |
| US5401889A (en) | 1993-11-12 | 1995-03-28 | Texaco Chemical Inc. | Preparation of tertiary butyl alcohol by catalytic decomposition of tertiary butyl hydroperoxide |
| US5364988A (en) | 1993-11-12 | 1994-11-15 | Texaco Chemical Company | Use of supported chromium catalyst in the preparation of tertiary butyl alcohol from tertiary butyl hydroperoxide |
| JPH07278152A (ja) | 1994-04-04 | 1995-10-24 | Sun Co Inc R & M | アルカンの酸化及び有機ヒドロペルオキシド類の分解用の金属リガンド触媒 |
| EP0931044B1 (en) | 1996-09-03 | 2002-11-20 | E.I. Du Pont De Nemours And Company | Hydroperoxide decomposition processes |
-
1998
- 1998-02-10 CA CA002279493A patent/CA2279493A1/en not_active Abandoned
- 1998-02-10 BR BRPI9815441-9A patent/BR9815441B1/pt not_active IP Right Cessation
- 1998-02-10 CN CN98802426A patent/CN1102923C/zh not_active Expired - Fee Related
- 1998-02-10 SK SK1058-99A patent/SK105899A3/sk unknown
- 1998-02-10 DE DE69810944T patent/DE69810944T2/de not_active Expired - Lifetime
- 1998-02-10 JP JP53508798A patent/JP3976793B2/ja not_active Expired - Fee Related
- 1998-02-10 EP EP98906452A patent/EP1012130B9/en not_active Expired - Lifetime
- 1998-02-10 PL PL98336762A patent/PL336762A1/xx unknown
- 1998-02-10 ID IDW990848A patent/ID22219A/id unknown
- 1998-02-10 EA EA199900737A patent/EA002422B1/ru unknown
- 1998-02-10 WO PCT/US1998/002926 patent/WO1998034894A2/en not_active Ceased
- 1998-02-10 CZ CZ19992832A patent/CZ295000B6/cs not_active IP Right Cessation
- 1998-02-10 KR KR19997007235A patent/KR20000070969A/ko not_active Ceased
- 1998-02-10 AU AU61674/98A patent/AU6167498A/en not_active Abandoned
-
2000
- 2000-02-02 US US09/496,328 patent/US6284927B1/en not_active Expired - Lifetime
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2851496A (en) * | 1954-07-27 | 1958-09-09 | Du Pont | Preparation of oxidation products of cyclohexane |
| GB1333129A (en) * | 1970-12-30 | 1973-10-10 | Shell Int Research | Process for the decomposition of organic peroxy compounds |
| US3941845A (en) * | 1972-10-21 | 1976-03-02 | Stamicarbon, B.V. | Process for preparing cycloalkanones and cycloalkanols |
| EP0453021A1 (en) * | 1990-04-14 | 1991-10-23 | Dsm N.V. | Process for preparing a cycloalkanone and/or cycloalkanol |
| WO1992016487A1 (en) * | 1991-03-25 | 1992-10-01 | Dsm N.V. | Process for preparing an alkanone and/or alkanol |
| WO1994008932A1 (en) * | 1992-10-09 | 1994-04-28 | Technische Universiteit Delft | Method for the catalyzed decomposition of organic hydroperoxides |
| EP0659726A1 (en) * | 1993-12-23 | 1995-06-28 | Dsm N.V. | Process for preparing an alkanone and/or an alkanol |
Also Published As
| Publication number | Publication date |
|---|---|
| AU6167498A (en) | 1998-08-26 |
| EP1012130A2 (en) | 2000-06-28 |
| US6284927B1 (en) | 2001-09-04 |
| CA2279493A1 (en) | 1998-08-13 |
| SK105899A3 (en) | 2000-07-11 |
| EP1012130B9 (en) | 2003-05-02 |
| MX9907212A (enExample) | 2000-02-28 |
| BR9815441B1 (pt) | 2009-12-01 |
| JP3976793B2 (ja) | 2007-09-19 |
| DE69810944T2 (de) | 2003-11-13 |
| EA199900737A1 (ru) | 2000-02-28 |
| KR20000070969A (ko) | 2000-11-25 |
| MX219178B (enExample) | 2004-02-16 |
| WO1998034894A2 (en) | 1998-08-13 |
| WO1998034894A3 (en) | 1999-01-21 |
| EP1012130B1 (en) | 2003-01-22 |
| CZ295000B6 (cs) | 2005-05-18 |
| ID22219A (id) | 1999-09-16 |
| PL336762A1 (en) | 2000-07-17 |
| BR9815441A (pt) | 2001-10-23 |
| CZ283299A3 (cs) | 2000-05-17 |
| HK1027554A1 (en) | 2001-01-19 |
| JP2001511787A (ja) | 2001-08-14 |
| CN1102923C (zh) | 2003-03-12 |
| DE69810944D1 (en) | 2003-02-27 |
| CN1246841A (zh) | 2000-03-08 |
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| PC4A | Registration of transfer of a eurasian patent by assignment |