CA2318788A1 - Direct oxidation of cycloalkanes - Google Patents
Direct oxidation of cycloalkanes Download PDFInfo
- Publication number
- CA2318788A1 CA2318788A1 CA002318788A CA2318788A CA2318788A1 CA 2318788 A1 CA2318788 A1 CA 2318788A1 CA 002318788 A CA002318788 A CA 002318788A CA 2318788 A CA2318788 A CA 2318788A CA 2318788 A1 CA2318788 A1 CA 2318788A1
- Authority
- CA
- Canada
- Prior art keywords
- process according
- catalyst
- gold
- sol
- solution
- 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.)
- Abandoned
Links
- 150000001924 cycloalkanes Chemical class 0.000 title claims abstract description 9
- 230000003647 oxidation Effects 0.000 title description 15
- 238000007254 oxidation reaction Methods 0.000 title description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 53
- 239000010931 gold Substances 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 39
- 230000008569 process Effects 0.000 claims abstract description 30
- 229910052737 gold Inorganic materials 0.000 claims abstract description 29
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 10
- 239000001301 oxygen Substances 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 230000001590 oxidative effect Effects 0.000 claims abstract description 9
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 9
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 8
- 229910052715 tantalum Inorganic materials 0.000 claims abstract description 8
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 8
- 230000003197 catalytic effect Effects 0.000 claims abstract description 7
- 150000002576 ketones Chemical class 0.000 claims abstract description 7
- 239000011159 matrix material Substances 0.000 claims abstract description 7
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 7
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 6
- 229910052758 niobium Inorganic materials 0.000 claims abstract description 6
- 150000004679 hydroxides Chemical class 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000002245 particle Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 7
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical group CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 5
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052593 corundum Inorganic materials 0.000 claims 1
- 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 230000000063 preceeding effect Effects 0.000 claims 1
- 229910001845 yogo sapphire Inorganic materials 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 abstract description 11
- 239000002184 metal Substances 0.000 abstract description 11
- 150000002739 metals Chemical class 0.000 abstract description 9
- 239000002638 heterogeneous catalyst Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 39
- 238000002474 experimental method Methods 0.000 description 21
- 239000000463 material Substances 0.000 description 20
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 150000004703 alkoxides Chemical class 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 11
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 10
- 239000011651 chromium Substances 0.000 description 9
- -1 A12O3 Inorganic materials 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000010936 titanium Substances 0.000 description 7
- 229910003803 Gold(III) chloride Inorganic materials 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- FVQGNKROUPZXBL-UHFFFAOYSA-L chromium(2+);acetate;hydroxide Chemical compound [OH-].[Cr+2].CC([O-])=O FVQGNKROUPZXBL-UHFFFAOYSA-L 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- RJHLTVSLYWWTEF-UHFFFAOYSA-K gold trichloride Chemical compound Cl[Au](Cl)Cl RJHLTVSLYWWTEF-UHFFFAOYSA-K 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 5
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229960005336 magnesium citrate Drugs 0.000 description 5
- 239000004337 magnesium citrate Substances 0.000 description 5
- 235000002538 magnesium citrate Nutrition 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 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 5
- 230000032683 aging Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XQMTUIZTZJXUFM-UHFFFAOYSA-N tetraethoxy silicate Chemical compound CCOO[Si](OOCC)(OOCC)OOCC XQMTUIZTZJXUFM-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- XCOBLONWWXQEBS-KPKJPENVSA-N N,O-bis(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)O\C(C(F)(F)F)=N\[Si](C)(C)C XCOBLONWWXQEBS-KPKJPENVSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004964 aerogel Substances 0.000 description 2
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 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
- XPGAWFIWCWKDDL-UHFFFAOYSA-N propan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCC[O-].CCC[O-].CCC[O-].CCC[O-] XPGAWFIWCWKDDL-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- RZYHXKLKJRGJGP-UHFFFAOYSA-N 2,2,2-trifluoro-n,n-bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)N([Si](C)(C)C)C(=O)C(F)(F)F RZYHXKLKJRGJGP-UHFFFAOYSA-N 0.000 description 1
- NGCRLFIYVFOUMZ-UHFFFAOYSA-N 2,3-dichloroquinoxaline-6-carbonyl chloride Chemical compound N1=C(Cl)C(Cl)=NC2=CC(C(=O)Cl)=CC=C21 NGCRLFIYVFOUMZ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910000906 Bronze Inorganic materials 0.000 description 1
- 102100033868 Cannabinoid receptor 1 Human genes 0.000 description 1
- 101710187010 Cannabinoid receptor 1 Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 101000800807 Homo sapiens Tumor necrosis factor alpha-induced protein 8 Proteins 0.000 description 1
- 241001606330 Paralia sol Species 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
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 102100033649 Tumor necrosis factor alpha-induced protein 8 Human genes 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 239000012482 calibration solution Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- 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
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229940076131 gold trichloride Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 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
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- 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 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/48—Silver or gold
- B01J23/52—Gold
-
- 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
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7425998P | 1998-02-10 | 1998-02-10 | |
| US60/074,259 | 1998-02-10 | ||
| US09/245,754 US6160183A (en) | 1998-02-10 | 1999-02-05 | Direct oxidation of cycloalkanes |
| US09/245,754 | 1999-02-05 | ||
| PCT/US1999/002477 WO1999040055A1 (en) | 1998-02-10 | 1999-02-09 | Direct oxidation of cycloalkanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2318788A1 true CA2318788A1 (en) | 1999-08-12 |
Family
ID=26755431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002318788A Abandoned CA2318788A1 (en) | 1998-02-10 | 1999-02-09 | Direct oxidation of cycloalkanes |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6160183A (https=) |
| EP (1) | EP1054854B1 (https=) |
| JP (1) | JP2003524579A (https=) |
| KR (1) | KR100611269B1 (https=) |
| CN (1) | CN1295547A (https=) |
| BR (1) | BR9908036A (https=) |
| CA (1) | CA2318788A1 (https=) |
| DE (1) | DE69907146T2 (https=) |
| PL (1) | PL342319A1 (https=) |
| SK (1) | SK283854B6 (https=) |
| TW (1) | TW470738B (https=) |
| WO (1) | WO1999040055A1 (https=) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2802526B1 (fr) * | 1999-12-17 | 2003-04-18 | Rhodia Polyamide Intermediates | Procede de preparation de melanges alcools/cetones |
| JP4580546B2 (ja) * | 2000-12-22 | 2010-11-17 | 丸善石油化学株式会社 | ２−ブタノン及び２−ブタノールの製造方法 |
| TWI329630B (en) * | 2002-04-03 | 2010-09-01 | Sumitomo Chemical Co | Method for oxidizing cycloalkane compound |
| US7081552B2 (en) * | 2004-08-17 | 2006-07-25 | Solutia Inc. | Catalysts for cycloalkanes oxidation and decomposition of cycloalkyl hydroperoxide |
| JP4635571B2 (ja) * | 2004-11-09 | 2011-02-23 | 住友化学株式会社 | 脂肪族環式炭化水素類の酸化反応に用いる触媒及びそれを用いる酸化方法 |
| CN1305829C (zh) * | 2004-11-12 | 2007-03-21 | 中国科学院兰州化学物理研究所 | 环己烷选择氧化制环己酮的方法 |
| JP4765371B2 (ja) * | 2005-03-30 | 2011-09-07 | 住友化学株式会社 | シクロヘキサノール及び／又はシクロヘキサノンの製造方法 |
| US7358401B2 (en) | 2005-03-31 | 2008-04-15 | Sumitomo Chemical Company, Limited | Method for manufacturing cycloalkanol and/or cycloalkanone |
| JP2007223992A (ja) * | 2006-02-27 | 2007-09-06 | Sumitomo Chemical Co Ltd | シクロアルカノール及び／又はシクロアルカノンの製造方法 |
| 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 |
| CN100435944C (zh) * | 2007-03-13 | 2008-11-26 | 浙江大学 | 一种负载型纳米金催化剂及制备方法 |
| JP5176426B2 (ja) * | 2007-03-16 | 2013-04-03 | 住友化学株式会社 | シクロアルカノール及び／又はシクロアルカノンの製造方法 |
| JP2009035519A (ja) | 2007-08-03 | 2009-02-19 | Sumitomo Chemical Co Ltd | シクロアルカノール及び／又はシクロアルカノンの製造方法 |
| JP5136017B2 (ja) | 2007-11-21 | 2013-02-06 | 住友化学株式会社 | シクロアルカノール及び／又はシクロアルカノンの製造方法 |
| CN101862660B (zh) * | 2010-06-04 | 2012-06-06 | 浙江大学 | 一种用于环己烷氧化的纳米金催化剂及其制备方法 |
| GB201201866D0 (en) * | 2012-02-03 | 2012-03-21 | Invista Tech Sarl | Oxidation reaction-I |
| CN102701905B (zh) * | 2012-05-04 | 2015-03-18 | 华东理工大学 | 一种环己烷选择性氧化制备环己酮和环己醇的方法 |
| ES3035113T3 (en) * | 2015-02-27 | 2025-08-28 | Gcp Applied Tech Inc | Modifying cementitious compositions using ketone alcohol oil waste |
| CN109806863A (zh) * | 2017-11-20 | 2019-05-28 | 中国科学院大连化学物理研究所 | 金催化剂的制备及其在环己烷氧化脱氢反应中的应用 |
| RU2020128668A (ru) * | 2018-01-30 | 2022-02-28 | Басф Се | Способ окисления циклоалканов |
| CN118871410A (zh) * | 2022-04-06 | 2024-10-29 | 切弗朗菲利浦化学公司 | 紫外光存在下铬催化的一氧化碳与烃的反应 |
| KR20250070912A (ko) * | 2023-11-14 | 2025-05-21 | 에스케이이노베이션 주식회사 | 암모니아 산화 촉매, 촉매 시스템 및 암모니아 산화 촉매의 제조방법 |
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| US2851496A (en) * | 1954-07-27 | 1958-09-09 | Du Pont | Preparation of oxidation products of cyclohexane |
| US3530185A (en) * | 1966-08-08 | 1970-09-22 | Du Pont | Oxidation process |
| NL174343C (nl) * | 1973-10-09 | 1984-06-01 | Stamicarbon | Werkwijze voor het bereiden van cycloalkanonen en cycloalkanolen door omzetting van een cycloalkylhydroperoxide. |
| US4042630A (en) * | 1973-10-19 | 1977-08-16 | Stamicarbon B.V. | Process for the preparation of cycloalkanones and cycloalkanols |
| 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 |
| JPH01294646A (ja) * | 1987-11-27 | 1989-11-28 | Mitsubishi Kasei Corp | シクロヘキサノール及びシクロヘキサノンの製造方法 |
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| NL9100521A (nl) * | 1991-03-25 | 1992-10-16 | Stamicarbon | Werkwijze voor de bereiding van een alkanon en/of alkanol. |
| GB9113343D0 (en) * | 1991-06-20 | 1991-08-07 | Shell Int Research | Catalytic oxidation of hydrocarbons |
| KR950010785B1 (ko) * | 1992-03-13 | 1995-09-23 | 재단법인한국화학연구소 | 시클로헥산올 및 시클로헥산온의 제조방법과 그에 사용되는 촉매 |
| BE1007904A3 (nl) * | 1993-12-23 | 1995-11-14 | Dsm Nv | Werkwijze voor de bereiding van een alkanol en/of een alkanon. |
| JPH07309793A (ja) * | 1994-03-22 | 1995-11-28 | Mitsubishi Chem Corp | 炭化水素類の酸化方法 |
| JP2615432B2 (ja) * | 1994-10-28 | 1997-05-28 | 工業技術院長 | 金−酸化チタン含有触媒による炭化水素の部分酸化方法 |
| JP3777437B2 (ja) * | 1996-03-21 | 2006-05-24 | 独立行政法人産業技術総合研究所 | 炭化水素の部分酸化方法および部分酸化用触媒 |
| KR100255480B1 (ko) * | 1996-03-21 | 2000-05-01 | 사또 다께오 | 탄화수소의 부분산화용촉매 및 탄화수소의 부분산화방법 |
| CN1102923C (zh) * | 1997-02-11 | 2003-03-12 | 纳幕尔杜邦公司 | 氢过氧化物的分解方法 |
| JP4000392B2 (ja) * | 1997-11-05 | 2007-10-31 | 独立行政法人産業技術総合研究所 | 炭化水素の部分酸化用触媒及び含酸素有機化合物の製法 |
-
1999
- 1999-02-05 US US09/245,754 patent/US6160183A/en not_active Expired - Fee Related
- 1999-02-09 KR KR1020007008613A patent/KR100611269B1/ko not_active Expired - Fee Related
- 1999-02-09 BR BR9908036-2A patent/BR9908036A/pt not_active IP Right Cessation
- 1999-02-09 CN CN99802838A patent/CN1295547A/zh active Pending
- 1999-02-09 SK SK1171-2000A patent/SK283854B6/sk unknown
- 1999-02-09 JP JP2000530487A patent/JP2003524579A/ja active Pending
- 1999-02-09 WO PCT/US1999/002477 patent/WO1999040055A1/en not_active Ceased
- 1999-02-09 DE DE69907146T patent/DE69907146T2/de not_active Expired - Lifetime
- 1999-02-09 EP EP99906746A patent/EP1054854B1/en not_active Expired - Lifetime
- 1999-02-09 PL PL99342319A patent/PL342319A1/xx unknown
- 1999-02-09 CA CA002318788A patent/CA2318788A1/en not_active Abandoned
- 1999-03-01 TW TW088102060A patent/TW470738B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| BR9908036A (pt) | 2000-11-28 |
| DE69907146T2 (de) | 2004-01-29 |
| JP2003524579A (ja) | 2003-08-19 |
| EP1054854A1 (en) | 2000-11-29 |
| SK11712000A3 (sk) | 2001-11-06 |
| KR20010040729A (ko) | 2001-05-15 |
| TW470738B (en) | 2002-01-01 |
| PL342319A1 (en) | 2001-06-04 |
| EP1054854B1 (en) | 2003-04-23 |
| US6160183A (en) | 2000-12-12 |
| CN1295547A (zh) | 2001-05-16 |
| SK283854B6 (sk) | 2004-03-02 |
| WO1999040055A1 (en) | 1999-08-12 |
| KR100611269B1 (ko) | 2006-08-10 |
| DE69907146D1 (de) | 2003-05-28 |
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