CA1077061A - Procede d'oxydation de cetones .beta.-ethyleniques - Google Patents
Procede d'oxydation de cetones .beta.-ethyleniquesInfo
- Publication number
- CA1077061A CA1077061A CA247,623A CA247623A CA1077061A CA 1077061 A CA1077061 A CA 1077061A CA 247623 A CA247623 A CA 247623A CA 1077061 A CA1077061 A CA 1077061A
- Authority
- CA
- Canada
- Prior art keywords
- isophorone
- chelate
- carbon atoms
- beta
- oxidation
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 27
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 16
- 150000002576 ketones Chemical class 0.000 title claims description 4
- 230000003647 oxidation Effects 0.000 claims abstract description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000013522 chelant Substances 0.000 claims abstract description 13
- 239000011572 manganese Substances 0.000 claims abstract description 13
- 239000001301 oxygen Substances 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 11
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000010941 cobalt Substances 0.000 claims abstract description 9
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 9
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 9
- 239000007788 liquid Substances 0.000 claims abstract description 6
- 239000007789 gas Substances 0.000 claims abstract description 4
- 150000007530 organic bases Chemical class 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- LKOKKQDYMZUSCG-UHFFFAOYSA-N 3,5,5-Trimethyl-3-cyclohexen-1-one Chemical compound CC1=CC(C)(C)CC(=O)C1 LKOKKQDYMZUSCG-UHFFFAOYSA-N 0.000 claims abstract 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- -1 aliphatic alcohols Chemical class 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 150000003973 alkyl amines Chemical group 0.000 claims description 4
- 150000001555 benzenes Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- NUGOTBXFVWXVTE-UHFFFAOYSA-N 2-hydroxy-3-nitrobenzaldehyde Chemical compound OC1=C(C=O)C=CC=C1[N+]([O-])=O NUGOTBXFVWXVTE-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 239000007810 chemical reaction solvent Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 229910052757 nitrogen Chemical group 0.000 claims description 3
- IIFFFBSAXDNJHX-UHFFFAOYSA-N 2-methyl-n,n-bis(2-methylpropyl)propan-1-amine Chemical compound CC(C)CN(CC(C)C)CC(C)C IIFFFBSAXDNJHX-UHFFFAOYSA-N 0.000 claims description 2
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004989 dicarbonyl group Chemical group 0.000 abstract description 2
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 230000001131 transforming effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 12
- 229940095076 benzaldehyde Drugs 0.000 description 11
- VEUMANXWQDHAJV-UHFFFAOYSA-N 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCN=CC1=CC=CC=C1O VEUMANXWQDHAJV-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 4
- 229940086542 triethylamine Drugs 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical group C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000036632 reaction speed Effects 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CHOOCIQDWNAXQQ-UHFFFAOYSA-N 1,5,5-trimethylcyclohexene Chemical compound CC1=CCCC(C)(C)C1 CHOOCIQDWNAXQQ-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- AUFZRCJENRSRLY-UHFFFAOYSA-N 2,3,5-trimethylhydroquinone Chemical compound CC1=CC(O)=C(C)C(C)=C1O AUFZRCJENRSRLY-UHFFFAOYSA-N 0.000 description 1
- HHDPXULKSZZACU-UHFFFAOYSA-N 2-hydroxy-4-nitrobenzaldehyde Chemical compound OC1=CC([N+]([O-])=O)=CC=C1C=O HHDPXULKSZZACU-UHFFFAOYSA-N 0.000 description 1
- IHFRMUGEILMHNU-UHFFFAOYSA-N 2-hydroxy-5-nitrobenzaldehyde Chemical compound OC1=CC=C([N+]([O-])=O)C=C1C=O IHFRMUGEILMHNU-UHFFFAOYSA-N 0.000 description 1
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical compound OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 1
- ZNNXJRURXWWGLN-UHFFFAOYSA-N 3-oxopentanal Chemical compound CCC(=O)CC=O ZNNXJRURXWWGLN-UHFFFAOYSA-N 0.000 description 1
- GMRGZEZAZUUZDQ-UHFFFAOYSA-N 5-methylcyclohex-2-ene-1,4-dione Chemical compound CC1CC(=O)C=CC1=O GMRGZEZAZUUZDQ-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- 235000014066 European mistletoe Nutrition 0.000 description 1
- 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 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
- 240000007673 Origanum vulgare Species 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 235000012300 Rhipsalis cassutha Nutrition 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000221012 Viscum Species 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229960005335 propanol Drugs 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000008096 xylene 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/2243—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
-
- 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
- C07C45/34—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 in unsaturated 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
- B01J2531/0241—Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
- B01J2531/0252—Salen ligands or analogues, e.g. derived from ethylenediamine and salicylaldehyde
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/70—Complexes comprising metals of Group VII (VIIB) as the central metal
- B01J2531/72—Manganese
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/845—Cobalt
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7507557A FR2303785A1 (fr) | 1975-03-11 | 1975-03-11 | Procede d'oxydation de cetones b-ethyleniques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1077061A true CA1077061A (fr) | 1980-05-06 |
Family
ID=9152405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA247,623A Expired CA1077061A (fr) | 1975-03-11 | 1976-03-09 | Procede d'oxydation de cetones .beta.-ethyleniques |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4026947A (enExample) |
| JP (1) | JPS51125316A (enExample) |
| BE (1) | BE839403A (enExample) |
| CA (1) | CA1077061A (enExample) |
| CH (1) | CH605519A5 (enExample) |
| DE (1) | DE2610254C2 (enExample) |
| FR (1) | FR2303785A1 (enExample) |
| GB (1) | GB1543255A (enExample) |
| IT (1) | IT1062086B (enExample) |
| NL (1) | NL7602512A (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2335487A1 (fr) * | 1975-12-19 | 1977-07-15 | Rhone Poulenc Ind | Procede de preparation de trimethyl-3,5,5 cyclohexene-2 dione-1,4 |
| US4195039A (en) * | 1976-09-30 | 1980-03-25 | Institut Francais Du Petrole | Heterogeneous phase oxidation of olefins to ketones |
| FR2368458A1 (fr) * | 1976-10-25 | 1978-05-19 | Rhone Poulenc Ind | Procede de preparation d'hydroxy-4 alcoyl-4 cyclohexadiene-2,5 one-1 |
| US4322562A (en) * | 1978-07-24 | 1982-03-30 | Allied Corporation | Oxidation process using metal nitro or nitrosyl complex |
| US4191696A (en) * | 1978-07-24 | 1980-03-04 | Allied Chemical Corporation | Oxidation process using metal nitro complex |
| JPH0819030B2 (ja) * | 1987-10-06 | 1996-02-28 | 曽田香料株式会社 | ３，５，５−トリメチルシクロヘキサ−２−エン−１，４−ジオンの製造方法 |
| DE3842547A1 (de) * | 1988-12-17 | 1990-06-21 | Huels Chemische Werke Ag | Verfahren zur herstellung von 2,6,6-trimethyl-cyclohex-2-en-1,4-dion |
| US5153161A (en) * | 1991-11-26 | 1992-10-06 | Lever Brothers Company, Division Of Conopco, Inc. | Synthesis of manganese oxidation catalyst |
| DE19619570A1 (de) * | 1996-05-15 | 1997-11-20 | Degussa | Verfahren zur Herstellung von Ketoisophoron |
| JPH11342340A (ja) * | 1998-06-01 | 1999-12-14 | Daicel Chem Ind Ltd | 酸化触媒系及びそれを用いたケトイソホロンの製造方法 |
| JPH11342342A (ja) | 1998-06-01 | 1999-12-14 | Daicel Chem Ind Ltd | 酸化触媒及びそれを用いた酸化方法 |
| JP2000034255A (ja) | 1998-07-16 | 2000-02-02 | Daicel Chem Ind Ltd | ケトイソホロンの製造方法および製造装置 |
| DE19929367A1 (de) * | 1999-06-25 | 2000-12-28 | Basf Ag | Verfahren zur Herstellung von Oxoisophoron |
| DE19929362A1 (de) | 1999-06-25 | 2000-12-28 | Basf Ag | Verfahren zur Herstellung von Oxoisophoron unter Verwendung von Additiven |
| JP5124959B2 (ja) * | 2006-03-07 | 2013-01-23 | 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 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2992272A (en) * | 1957-02-25 | 1961-07-11 | Gen Electric | Preparation of carbonyl olefins |
| US3232957A (en) * | 1963-11-18 | 1966-02-01 | Monsanto Co | Process for the preparation of olefin oxides |
| NL6410417A (enExample) * | 1964-09-08 | 1966-03-09 | ||
| CH559156A5 (enExample) * | 1972-11-16 | 1975-02-28 | Firmenich & Cie | |
| JPS4930330A (enExample) * | 1973-03-23 | 1974-03-18 | ||
| CH586173A5 (enExample) * | 1973-12-07 | 1977-03-31 | Firmenich & Cie | |
| CH605535A5 (enExample) * | 1974-04-11 | 1978-09-29 | Hoffmann La Roche | |
| CH611590A5 (en) * | 1974-06-28 | 1979-06-15 | Hoffmann La Roche | Process for the preparation of a diketo compound |
| CH599917A5 (enExample) * | 1974-07-10 | 1978-06-15 | Firmenich & Cie |
-
1975
- 1975-03-11 FR FR7507557A patent/FR2303785A1/fr active Granted
-
1976
- 1976-02-23 US US05/660,721 patent/US4026947A/en not_active Expired - Lifetime
- 1976-03-09 JP JP51025507A patent/JPS51125316A/ja active Granted
- 1976-03-09 CA CA247,623A patent/CA1077061A/fr not_active Expired
- 1976-03-10 NL NL7602512A patent/NL7602512A/xx not_active Application Discontinuation
- 1976-03-10 GB GB9621/76A patent/GB1543255A/en not_active Expired
- 1976-03-10 BE BE165025A patent/BE839403A/xx not_active IP Right Cessation
- 1976-03-10 CH CH299176A patent/CH605519A5/xx not_active IP Right Cessation
- 1976-03-11 IT IT21081/76A patent/IT1062086B/it active
- 1976-03-11 DE DE2610254A patent/DE2610254C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH605519A5 (enExample) | 1978-09-29 |
| DE2610254C2 (de) | 1985-03-07 |
| US4026947A (en) | 1977-05-31 |
| NL7602512A (nl) | 1976-09-14 |
| JPS51125316A (en) | 1976-11-01 |
| GB1543255A (en) | 1979-03-28 |
| JPS6149296B2 (enExample) | 1986-10-29 |
| DE2610254A1 (de) | 1976-09-23 |
| FR2303785A1 (fr) | 1976-10-08 |
| FR2303785B1 (enExample) | 1977-11-18 |
| BE839403A (fr) | 1976-09-10 |
| IT1062086B (it) | 1983-06-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1077061A (fr) | Procede d'oxydation de cetones .beta.-ethyleniques | |
| EP2097431B1 (fr) | Complexes catalytiques a base de ruthenium et utilisation de tels complexes pour la metathese d'olefines | |
| Mao et al. | Novel Schiff base complexes as catalysts in aerobic selective oxidation of β-isophorone | |
| JPS6045621B2 (ja) | ブタノン誘導体の製造方法 | |
| FR3058140A1 (fr) | Catalyseurs supportes cycliques | |
| CH642342A5 (fr) | Procede pour la preparation de muscone. | |
| EP0091851B1 (fr) | Procédé de préparation d'éthers d'aryle portant des substituants différents sur les deux noyaux aromatiques | |
| CN109232529B (zh) | 一种Rh(III)催化具有氮杂环骨架的化合物的制备方法 | |
| CA1312625C (fr) | Procede de production d'aldehydes aromatiques | |
| EP0087347B1 (fr) | Procédé de préparation de benzoxazolone-2 et dérivés à partir d'orthonitrophénols et de monoxyde de carbone | |
| EP0625146B1 (fr) | Nouveaux anhydrides d'acides, leur preparation et leur emploi | |
| JP2005008633A (ja) | フッ素含有アセトフェノンの製造方法およびその使用 | |
| CN109776297B (zh) | 一种烷氧基取代的3,4-二氢化萘类化合物的合成方法 | |
| EP0708754B1 (fr) | Procede de preparation de n-carbonylarylimines utiles dans la synthese de taxoides therapeutiquement actifs | |
| EP0685473B1 (fr) | Composés benzohétérocycliques, en tant qu'antioxydants | |
| CH643226A5 (fr) | Procede de fabrication de composes carbonyles par oxydation de composes olefiniques. | |
| JPH04149160A (ja) | １―アミノ―４―アルコキシベンゼン類の製造方法 | |
| CH651545A5 (fr) | Sulfones aromatiques et leur preparation. | |
| CN117069602B (zh) | 一种γ-胺基醇类化合物的合成方法 | |
| EP0117186B1 (fr) | Procédé de préparation de dérivés du cyclopropane | |
| FR2797443A1 (fr) | Procede de prepartion de quinoleine-5,8-diones | |
| JP2003299962A (ja) | キラルジルコニウム触媒とアンチ選択性非対称アルドール反応方法 | |
| EP0012390A2 (fr) | Procédé pour la préparation de la muscone et composés pyranniques intermédiaires | |
| CN116102562A (zh) | 一种萘并[2,1-b]吲哚并[2,3-d]环辛内酯衍生物及其制备方法 | |
| EP0376824A1 (fr) | Procédé de préparaton de dérivés du chromanne et intermédiaires de synthèse |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |