CA2362261A1 - Hydroperoxide decomposition process - Google Patents

Hydroperoxide decomposition process Download PDF

Info

Publication number: CA2362261A1
Authority: CA; Canada
Prior art keywords: chhp; gold; process according; hydroperoxide; catalyst
Prior art date: 1999-03-10
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

Application number

CA002362261A

Other languages

English (en)

French (fr)

Inventor

Joe Douglas Druliner

Norman Herron

Stephen Paul Jordan

Samuel Livingston Lane

Leo Ernest Manzer

Nicholas Edward Kob Iii

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

INVISTA TECHNOLOGIES Sarl

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

1999-03-10

Filing date

1999-03-10

Publication date

2000-09-14

1999-03-10 Application filed by Individual filed Critical Individual

2000-09-14 Publication of CA2362261A1 publication Critical patent/CA2362261A1/en

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 58
230000008569 process Effects 0.000 title claims abstract description 49
238000000354 decomposition reaction Methods 0.000 title claims abstract description 33
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 title claims abstract description 15
239000010931 gold Substances 0.000 claims abstract description 62
239000003054 catalyst Substances 0.000 claims abstract description 60
229910052737 gold Inorganic materials 0.000 claims abstract description 58
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 40
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims abstract description 25
229910052681 coesite Inorganic materials 0.000 claims abstract description 17
229910052906 cristobalite Inorganic materials 0.000 claims abstract description 17
229910052682 stishovite Inorganic materials 0.000 claims abstract description 17
229910052905 tridymite Inorganic materials 0.000 claims abstract description 17
229910052751 metal Inorganic materials 0.000 claims abstract description 15
239000002184 metal Substances 0.000 claims abstract description 15
229910052799 carbon Inorganic materials 0.000 claims abstract description 14
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 13
239000011541 reaction mixture Substances 0.000 claims abstract description 13
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims abstract description 11
239000000377 silicon dioxide Substances 0.000 claims abstract description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
230000006872 improvement Effects 0.000 claims abstract description 7
150000002576 ketones Chemical class 0.000 claims abstract description 7
150000002739 metals Chemical class 0.000 claims abstract description 7
235000012239 silicon dioxide Nutrition 0.000 claims abstract 2
FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical group OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 claims description 73
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 20
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 13
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 11
230000003197 catalytic effect Effects 0.000 claims description 10
229910052697 platinum Inorganic materials 0.000 claims description 8
239000002245 particle Substances 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000002638 heterogeneous catalyst Substances 0.000 claims description 4
229910052759 nickel Inorganic materials 0.000 claims description 3
229910052707 ruthenium Inorganic materials 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
239000001301 oxygen Substances 0.000 claims 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract description 15
-1 zirconi a Chemical compound 0.000 abstract description 6
230000000737 periodic effect Effects 0.000 abstract description 4
125000000217 alkyl group Chemical group 0.000 abstract description 3
125000003118 aryl group Chemical group 0.000 abstract 1
229910052593 corundum Inorganic materials 0.000 abstract 1
229910001845 yogo sapphire Inorganic materials 0.000 abstract 1
239000000243 solution Substances 0.000 description 29
239000007787 solid Substances 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
238000002474 experimental method Methods 0.000 description 19
239000000203 mixture Substances 0.000 description 19
PBKONEOXTCPAFI-UHFFFAOYSA-N TCB Natural products ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
229910052763 palladium Inorganic materials 0.000 description 16
239000002002 slurry Substances 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000000499 gel Substances 0.000 description 9
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 9
229910003803 Gold(III) chloride Inorganic materials 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
239000010949 copper Substances 0.000 description 8
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
RJHLTVSLYWWTEF-UHFFFAOYSA-K gold trichloride Chemical compound Cl[Au](Cl)Cl RJHLTVSLYWWTEF-UHFFFAOYSA-K 0.000 description 8
229940076131 gold trichloride Drugs 0.000 description 8
239000000463 material Substances 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 7
239000001509 sodium citrate Substances 0.000 description 7
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 7
239000002904 solvent Substances 0.000 description 7
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 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
238000001914 filtration Methods 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
230000003647 oxidation Effects 0.000 description 6
238000007254 oxidation reaction Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
NJXPYZHXZZCTNI-UHFFFAOYSA-N 3-aminobenzonitrile Chemical compound NC1=CC=CC(C#N)=C1 NJXPYZHXZZCTNI-UHFFFAOYSA-N 0.000 description 5
229910052802 copper Inorganic materials 0.000 description 5
238000004519 manufacturing process Methods 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
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
239000001361 adipic acid Substances 0.000 description 4
235000011037 adipic acid Nutrition 0.000 description 4
230000008901 benefit Effects 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 4
239000007789 gas Substances 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
229910052709 silver Inorganic materials 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000012535 impurity Substances 0.000 description 3
239000007791 liquid phase Substances 0.000 description 3
239000000395 magnesium oxide Substances 0.000 description 3
239000002243 precursor Substances 0.000 description 3
239000000376 reactant Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000010944 silver (metal) Substances 0.000 description 3
229910000906 Bronze Inorganic materials 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
239000004964 aerogel Substances 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
239000010974 bronze Substances 0.000 description 2
238000006555 catalytic reaction Methods 0.000 description 2
KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 2
239000012530 fluid Substances 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000011068 loading method Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000011550 stock solution Substances 0.000 description 2
XQMTUIZTZJXUFM-UHFFFAOYSA-N tetraethoxy silicate Chemical group CCOO[Si](OOCC)(OOCC)OOCC XQMTUIZTZJXUFM-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
NYHNVHGFPZAZGA-UHFFFAOYSA-N 2-hydroxyhexanoic acid Chemical compound CCCCC(O)C(O)=O NYHNVHGFPZAZGA-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
241000167854 Bourreria succulenta Species 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
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000012482 calibration solution Substances 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
235000019693 cherries Nutrition 0.000 description 1
239000003426 co-catalyst Substances 0.000 description 1
238000000576 coating method Methods 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
239000000084 colloidal system Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000000470 constituent Substances 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
238000004132 cross linking Methods 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
238000000151 deposition Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
229910001882 dioxygen Inorganic materials 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000009826 distribution Methods 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
235000019253 formic acid Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
FDWREHZXQUYJFJ-UHFFFAOYSA-M gold monochloride Chemical compound [Cl-].[Au+] FDWREHZXQUYJFJ-UHFFFAOYSA-M 0.000 description 1
229940111120 gold preparations Drugs 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229910052735 hafnium Inorganic materials 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
GPHZOCJETVZYTP-UHFFFAOYSA-N hydroperoxycyclododecane Chemical compound OOC1CCCCCCCCCCC1 GPHZOCJETVZYTP-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000003446 ligand Substances 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 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
229910052762 osmium Inorganic materials 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000004033 plastic Substances 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
230000009467 reduction Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910052719 titanium Inorganic materials 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
239000011882 ultra-fine particle Substances 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C27/00—Processes involving the simultaneous production of more than one class of oxygen-containing compounds
- 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
- C07C29/132—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)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA002362261A 1999-03-10 1999-03-10 Hydroperoxide decomposition process Abandoned CA2362261A1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PCT/US1999/005228 WO2000053550A1 (en)	1999-03-10	1999-03-10	Hydroperoxide decomposition process

Publications (1)

Publication Number	Publication Date
CA2362261A1 true CA2362261A1 (en)	2000-09-14

Family

ID=22272330

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002362261A Abandoned CA2362261A1 (en)	1999-03-10	1999-03-10	Hydroperoxide decomposition process

Country Status (12)

Country	Link
EP (1)	EP1159240A1 (cs)
JP (1)	JP2002539097A (cs)
KR (1)	KR20020018999A (cs)
CN (1)	CN1337930A (cs)
AU (1)	AU2903199A (cs)
BR (1)	BR9917285A (cs)
CA (1)	CA2362261A1 (cs)
CZ (1)	CZ20013106A3 (cs)
MX (1)	MXPA01009075A (cs)
PL (1)	PL357043A1 (cs)
SK (1)	SK12312001A3 (cs)
WO (1)	WO2000053550A1 (cs)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10244996A1 (de) *	2002-09-26	2004-04-01	Basf Ag	Katalysator für die katalytische Chlorwasserstoff-Oxidation
JP2004181358A (ja) *	2002-12-03	2004-07-02	Nippon Shokubai Co Ltd	液相反応用金担持触媒及びカルボン酸エステルの製造方法
JP4578820B2 (ja) *	2004-02-19	2010-11-10	トヨタ自動車株式会社	金触媒の製造方法およびその使用方法
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
PT104862A (pt)	2009-12-07	2011-06-07	Univ Tras Os Montes E Alto Douro	Catalisadores híbridos de vanádio e sua utilização em processos de oxidação selectiva de cicloalcanos
CN103562168B (zh) *	2011-07-15	2016-08-17	Lg化学株式会社	异丙苯醇的制备方法和苯酚、丙酮及α-甲基苯乙烯的制备方法
US11572330B2 (en) *	2018-01-30	2023-02-07	Basf Se	Method for oxidation of cycloalkanes

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL9100521A (nl) *	1991-03-25	1992-10-16	Stamicarbon	Werkwijze voor de bereiding van een alkanon en/of alkanol.
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
KR20000070969A (ko) *	1997-02-11	2000-11-25	메리 이. 보울러	히드로과산화물 분해 방법

1999
- 1999-03-10 CA CA002362261A patent/CA2362261A1/en not_active Abandoned
- 1999-03-10 CZ CZ20013106A patent/CZ20013106A3/cs unknown
- 1999-03-10 CN CN99816427A patent/CN1337930A/zh active Pending
- 1999-03-10 AU AU29031/99A patent/AU2903199A/en not_active Abandoned
- 1999-03-10 PL PL99357043A patent/PL357043A1/xx unknown
- 1999-03-10 BR BR9917285-2A patent/BR9917285A/pt not_active Application Discontinuation
- 1999-03-10 WO PCT/US1999/005228 patent/WO2000053550A1/en not_active Ceased
- 1999-03-10 EP EP99909950A patent/EP1159240A1/en not_active Withdrawn
- 1999-03-10 MX MXPA01009075A patent/MXPA01009075A/es unknown
- 1999-03-10 SK SK1231-2001A patent/SK12312001A3/sk not_active Application Discontinuation
- 1999-03-10 JP JP2000603993A patent/JP2002539097A/ja active Pending
- 1999-03-10 KR KR1020017011432A patent/KR20020018999A/ko not_active Ceased

Also Published As

Publication number	Publication date
PL357043A1 (en)	2004-07-12
BR9917285A (pt)	2001-12-26
SK12312001A3 (sk)	2002-02-05
MXPA01009075A (es)	2002-03-27
CN1337930A (zh)	2002-02-27
JP2002539097A (ja)	2002-11-19
AU2903199A (en)	2000-09-28
WO2000053550A1 (en)	2000-09-14
KR20020018999A (ko)	2002-03-09
CZ20013106A3 (cs)	2002-05-15
EP1159240A1 (en)	2001-12-05

Legal Events

Date	Code	Title	Description
2003-12-18	EEER	Examination request
2010-09-09	FZDE	Dead

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