SK158294A3 - Method of preparation of alkanone and/or alkanol - Google Patents

Method of preparation of alkanone and/or alkanol Download PDF

Info

Publication number: SK158294A3
Authority: SK; Slovakia
Prior art keywords: decomposition; catalyst; aqueous phase; mixture; solution
Prior art date: 1993-12-23

Application number

SK1582-94A

Other languages

English (en)

Slovak (sk)

Inventor

Ubaldus F Kragten

Henricus A C Baur

Original Assignee

Dsm Nv

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.)

1993-12-23

Filing date

1994-12-21

Publication date

1995-08-09

1994-12-21 Application filed by Dsm Nv filed Critical Dsm Nv

1995-08-09 Publication of SK158294A3 publication Critical patent/SK158294A3/sk

Links

238000000034 method Methods 0.000 title claims description 199
238000002360 preparation method Methods 0.000 title claims description 27
239000003054 catalyst Substances 0.000 claims abstract description 184
238000000354 decomposition reaction Methods 0.000 claims abstract description 176
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 74
229910052751 metal Inorganic materials 0.000 claims abstract description 34
239000002184 metal Substances 0.000 claims abstract description 34
150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 29
150000001336 alkenes Chemical class 0.000 claims abstract description 28
150000002736 metal compounds Chemical class 0.000 claims abstract description 26
239000012876 carrier material Substances 0.000 claims abstract description 24
230000001590 oxidative effect Effects 0.000 claims abstract description 23
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
229910052802 copper Inorganic materials 0.000 claims abstract description 14
229910052742 iron Inorganic materials 0.000 claims abstract description 14
229910052759 nickel Inorganic materials 0.000 claims abstract description 14
229910052748 manganese Inorganic materials 0.000 claims abstract description 12
229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 10
239000001301 oxygen Substances 0.000 claims abstract description 10
239000000203 mixture Substances 0.000 claims description 130
239000008346 aqueous phase Substances 0.000 claims description 123
230000008569 process Effects 0.000 claims description 116
238000007254 oxidation reaction Methods 0.000 claims description 71
230000003647 oxidation Effects 0.000 claims description 67
239000000243 solution Substances 0.000 claims description 52
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 48
239000010941 cobalt Substances 0.000 claims description 47
229910017052 cobalt Inorganic materials 0.000 claims description 47
239000000463 material Substances 0.000 claims description 47
239000007864 aqueous solution Substances 0.000 claims description 46
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 45
-1 alkyl hydroperoxide Chemical compound 0.000 claims description 44
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 39
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 39
229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 28
150000008041 alkali metal carbonates Chemical class 0.000 claims description 27
239000012071 phase Substances 0.000 claims description 27
239000010949 copper Substances 0.000 claims description 26
229910000029 sodium carbonate Inorganic materials 0.000 claims description 24
239000011572 manganese Substances 0.000 claims description 23
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 16
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 16
229910010413 TiO 2 Inorganic materials 0.000 claims description 15
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 14
239000002245 particle Substances 0.000 claims description 14
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 13
238000006386 neutralization reaction Methods 0.000 claims description 12
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical group [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 11
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 10
238000000926 separation method Methods 0.000 claims description 10
150000001924 cycloalkanes Chemical class 0.000 claims description 8
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 8
239000004408 titanium dioxide Substances 0.000 claims description 8
238000002485 combustion reaction Methods 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
229910000318 alkali metal phosphate Inorganic materials 0.000 claims description 4
230000003134 recirculating effect Effects 0.000 claims description 3
239000012670 alkaline solution Substances 0.000 claims description 2
239000003637 basic solution Substances 0.000 claims description 2
239000003153 chemical reaction reagent Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 abstract description 4
239000011734 sodium Substances 0.000 description 58
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 54
FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 52
238000004448 titration Methods 0.000 description 36
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 28
238000006243 chemical reaction Methods 0.000 description 26
239000011541 reaction mixture Substances 0.000 description 22
SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 description 16
229910044991 metal oxide Inorganic materials 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
GPHZOCJETVZYTP-UHFFFAOYSA-N hydroperoxycyclododecane Chemical compound OOC1CCCCCCCCCCC1 GPHZOCJETVZYTP-UHFFFAOYSA-N 0.000 description 12
150000004706 metal oxides Chemical class 0.000 description 12
239000012074 organic phase Substances 0.000 description 12
239000007858 starting material Substances 0.000 description 12
230000003197 catalytic effect Effects 0.000 description 11
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 10
229910021536 Zeolite Inorganic materials 0.000 description 10
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 10
239000007788 liquid Substances 0.000 description 10
239000010457 zeolite Substances 0.000 description 10
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 8
230000000052 comparative effect Effects 0.000 description 8
150000001875 compounds Chemical class 0.000 description 8
DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 8
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 8
239000003446 ligand Substances 0.000 description 8
239000000047 product Substances 0.000 description 8
CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 8
238000005201 scrubbing Methods 0.000 description 8
239000007787 solid Substances 0.000 description 8
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 6
239000005751 Copper oxide Substances 0.000 description 6
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 6
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 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
239000011651 chromium Substances 0.000 description 6
229910052804 chromium Inorganic materials 0.000 description 6
229910000431 copper oxide Inorganic materials 0.000 description 6
SFVWPXMPRCIVOK-UHFFFAOYSA-N cyclododecanol Chemical compound OC1CCCCCCCCCCC1 SFVWPXMPRCIVOK-UHFFFAOYSA-N 0.000 description 6
238000000151 deposition Methods 0.000 description 6
239000007789 gas Substances 0.000 description 6
239000011521 glass Substances 0.000 description 6
239000008188 pellet Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
230000000694 effects Effects 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
229910021503 Cobalt(II) hydroxide Inorganic materials 0.000 description 4
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
230000008901 benefit Effects 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
238000006555 catalytic reaction Methods 0.000 description 4
150000001868 cobalt Chemical class 0.000 description 4
ASKVAEGIVYSGNY-UHFFFAOYSA-L cobalt(ii) hydroxide Chemical compound [OH-].[OH-].[Co+2] ASKVAEGIVYSGNY-UHFFFAOYSA-L 0.000 description 4
DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical group C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 4
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 4
239000004914 cyclooctane Substances 0.000 description 4
230000008021 deposition Effects 0.000 description 4
ODLMAHJVESYWTB-UHFFFAOYSA-N ethylmethylbenzene Natural products CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 4
239000008187 granular material Substances 0.000 description 4
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
238000003947 neutron activation analysis Methods 0.000 description 4
238000005191 phase separation Methods 0.000 description 4
239000002002 slurry Substances 0.000 description 4
229910052723 transition metal Inorganic materials 0.000 description 4
150000003624 transition metals Chemical class 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
229920002292 Nylon 6 Polymers 0.000 description 2
229920002302 Nylon 6,6 Polymers 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
229910018557 Si O Inorganic materials 0.000 description 2
229910000831 Steel Inorganic materials 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000009471 action Effects 0.000 description 2
239000001361 adipic acid Substances 0.000 description 2
235000011037 adipic acid Nutrition 0.000 description 2
239000003513 alkali Substances 0.000 description 2
150000001340 alkali metals Chemical class 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
150000001412 amines Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
239000003575 carbonaceous material Substances 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
238000001311 chemical methods and process Methods 0.000 description 2
229910000428 cobalt oxide Inorganic materials 0.000 description 2
IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
JHIVVAPYMSGYDF-PTQBSOBMSA-N cyclohexanone Chemical class O=[13C]1CCCCC1 JHIVVAPYMSGYDF-PTQBSOBMSA-N 0.000 description 2
IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
210000003298 dental enamel Anatomy 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000009826 distribution Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000004677 hydrates Chemical class 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 description 2
230000005660 hydrophilic surface Effects 0.000 description 2
238000005470 impregnation Methods 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
UBUHAZKODAUXCP-UHFFFAOYSA-N iron(2+);oxygen(2-);hydrate Chemical class O.[O-2].[Fe+2] UBUHAZKODAUXCP-UHFFFAOYSA-N 0.000 description 2
235000013847 iso-butane Nutrition 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
JJIJKNKBEFFVIK-UHFFFAOYSA-N manganese(2+);oxygen(2-);hydrate Chemical class O.[O-2].[Mn+2] JJIJKNKBEFFVIK-UHFFFAOYSA-N 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
150000005172 methylbenzenes Chemical class 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
MMUCNHNUAIJJRH-UHFFFAOYSA-N oxonickel hydrate Chemical class [O].O.[Ni] MMUCNHNUAIJJRH-UHFFFAOYSA-N 0.000 description 2
239000011148 porous material Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
238000002203 pretreatment Methods 0.000 description 2
230000001737 promoting effect Effects 0.000 description 2
239000001294 propane Substances 0.000 description 2
230000009467 reduction Effects 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000010959 steel Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000758 substrate Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
150000003623 transition metal compounds Chemical class 0.000 description 2
239000012498 ultrapure water Substances 0.000 description 2
229910052720 vanadium Inorganic materials 0.000 description 2
239000002699 waste material Substances 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 1
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229910001928 zirconium oxide 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
- C07C27/10—Processes involving the simultaneous production of more than one class of oxygen-containing compounds by oxidation of hydrocarbons
- C07C27/12—Processes involving the simultaneous production of more than one class of oxygen-containing compounds by oxidation of hydrocarbons with oxygen
- 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
- 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
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Emergency Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

SK1582-94A 1993-12-23 1994-12-21 Method of preparation of alkanone and/or alkanol SK158294A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
BE9301446A BE1007904A3 (nl)	1993-12-23	1993-12-23	Werkwijze voor de bereiding van een alkanol en/of een alkanon.

Publications (1)

Publication Number	Publication Date
SK158294A3 true SK158294A3 (en)	1995-08-09

Family

ID=3887673

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1582-94A SK158294A3 (en)	1993-12-23	1994-12-21	Method of preparation of alkanone and/or alkanol

Country Status (17)

Country	Link
US (1)	US5859301A (de)
EP (1)	EP0659726B1 (de)
JP (1)	JPH07247230A (de)
KR (1)	KR950017887A (de)
CN (1)	CN1071301C (de)
BE (1)	BE1007904A3 (de)
BR (1)	BR9405216A (de)
CA (1)	CA2138751A1 (de)
CZ (1)	CZ327894A3 (de)
DE (1)	DE69421506T2 (de)
ES (1)	ES2139047T3 (de)
HU (1)	HU218388B (de)
MX (1)	MX9500220A (de)
PL (1)	PL179828B1 (de)
RU (1)	RU94044355A (de)
SK (1)	SK158294A3 (de)
TW (1)	TW358800B (de)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE1009662A3 (nl) *	1995-10-13	1997-06-03	Dsm Nv	Werkwijze voor het ontleden van cycloalkylhydroperoxide.
KR20000070969A (ko) *	1997-02-11	2000-11-25	메리 이. 보울러	히드로과산화물 분해 방법
BE1011041A3 (nl) *	1997-03-12	1999-04-06	Dsm Nv	Werkwijze voor het ontleden van cycloalkylhydroperoxide.
US6160183A (en) *	1998-02-10	2000-12-12	E. I. Du Pont De Nemours And Company	Direct oxidation of cycloalkanes
FR2802526B1 (fr) *	1999-12-17	2003-04-18	Rhodia Polyamide Intermediates	Procede de preparation de melanges alcools/cetones
US6700022B2 (en) *	2002-06-05	2004-03-02	E. I. Du Pont De Nemours And Company	High yield cyclohexyl hydroperoxide decompostition process
US20030228972A1 (en) *	2002-06-05	2003-12-11	Birss Viola	Oxygen reduction catalyst
US20040158103A1 (en) *	2003-02-11	2004-08-12	Solutia Inc.	Cyclohexane oxidation catalysts
US7081552B2 (en) *	2004-08-17	2006-07-25	Solutia Inc.	Catalysts for cycloalkanes oxidation and decomposition of cycloalkyl hydroperoxide
CN101010273B (zh) *	2004-08-24	2010-06-30	因维斯塔技术有限公司	减少含有环己烯酮的有机混合物中的环己烯酮含量的方法
JP2008528528A (ja) *	2005-01-25	2008-07-31	ディーエスエムアイピーアセッツビー．ブイ．	シクロヘキサノンおよびシクロヘキサノールの製造方法
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1993
- 1993-12-23 BE BE9301446A patent/BE1007904A3/nl not_active IP Right Cessation
1994
- 1994-12-13 TW TW083111600A patent/TW358800B/zh active
- 1994-12-19 DE DE69421506T patent/DE69421506T2/de not_active Expired - Fee Related
- 1994-12-19 ES ES94203682T patent/ES2139047T3/es not_active Expired - Lifetime
- 1994-12-19 EP EP94203682A patent/EP0659726B1/de not_active Expired - Lifetime
- 1994-12-21 SK SK1582-94A patent/SK158294A3/sk unknown
- 1994-12-21 JP JP6318840A patent/JPH07247230A/ja active Pending
- 1994-12-21 PL PL94306450A patent/PL179828B1/pl unknown
- 1994-12-21 CA CA002138751A patent/CA2138751A1/en not_active Abandoned
- 1994-12-21 HU HU9403725A patent/HU218388B/hu not_active IP Right Cessation
- 1994-12-22 CZ CZ943278A patent/CZ327894A3/cs unknown
- 1994-12-22 BR BR9405216A patent/BR9405216A/pt not_active IP Right Cessation
- 1994-12-22 CN CN94113210A patent/CN1071301C/zh not_active Expired - Fee Related
- 1994-12-22 RU RU94044355/04A patent/RU94044355A/ru unknown
- 1994-12-23 KR KR1019940036148A patent/KR950017887A/ko not_active Ceased
- 1994-12-23 US US08/363,238 patent/US5859301A/en not_active Expired - Fee Related
1995
- 1995-01-02 MX MX9500220A patent/MX9500220A/es unknown

Also Published As

Publication number	Publication date
RU94044355A (ru)	1996-10-27
ES2139047T3 (es)	2000-02-01
BE1007904A3 (nl)	1995-11-14
HUT69062A (en)	1995-08-28
JPH07247230A (ja)	1995-09-26
KR950017887A (ko)	1995-07-20
BR9405216A (pt)	1995-08-01
HU9403725D0 (en)	1995-03-28
TW358800B (en)	1999-05-21
PL179828B1 (pl)	2000-11-30
PL306450A1 (en)	1995-06-26
HU218388B (hu)	2000-08-28
CA2138751A1 (en)	1995-06-24
US5859301A (en)	1999-01-12
CN1107829A (zh)	1995-09-06
DE69421506D1 (de)	1999-12-09
DE69421506T2 (de)	2000-07-06
MX9500220A (es)	1997-04-30
EP0659726B1 (de)	1999-11-03
CZ327894A3 (en)	1995-10-18
EP0659726A1 (de)	1995-06-28
CN1071301C (zh)	2001-09-19

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