NL9000893A - Werkwijze voor de bereiding van een cycloalkanon en/of cycloalkanol. - Google Patents

Werkwijze voor de bereiding van een cycloalkanon en/of cycloalkanol. Download PDF

Info

Publication number: NL9000893A
Authority: NL; Netherlands
Prior art keywords: metal; oxidation; hydroperoxide; cycloal; catalyst
Prior art date: 1990-04-14

Application number

NL9000893A

Other languages

English (en)

Dutch (nl)

Original Assignee

Stamicarbon

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.)

1990-04-14

Filing date

1990-04-14

Publication date

1991-11-01

1990-04-14 Application filed by Stamicarbon filed Critical Stamicarbon

1990-04-14 Priority to NL9000893A priority Critical patent/NL9000893A/nl

1991-04-10 Priority to EP91200831A priority patent/EP0453021A1/fr

1991-04-11 Priority to MX025308A priority patent/MX167121B/es

1991-04-12 Priority to HU911228A priority patent/HUT56807A/hu

1991-04-12 Priority to PT97366A priority patent/PT97366A/pt

1991-04-12 Priority to AU74385/91A priority patent/AU642724B2/en

1991-04-12 Priority to CA002040378A priority patent/CA2040378A1/fr

1991-04-12 Priority to JP3079758A priority patent/JPH04224536A/ja

1991-04-13 Priority to SU914895077A priority patent/RU2002725C1/ru

1991-04-13 Priority to CN91103225A priority patent/CN1056485A/zh

1991-04-15 Priority to KR1019910006007A priority patent/KR920005711A/ko

1991-04-15 Priority to BR919101517A priority patent/BR9101517A/pt

1991-04-15 Priority to CS911064A priority patent/CS106491A2/cs

1991-11-01 Publication of NL9000893A publication Critical patent/NL9000893A/nl

Links

238000004519 manufacturing process Methods 0.000 title 1
238000007254 oxidation reaction Methods 0.000 claims description 27
230000003647 oxidation Effects 0.000 claims description 26
238000000034 method Methods 0.000 claims description 24
229910052751 metal Inorganic materials 0.000 claims description 23
239000002184 metal Substances 0.000 claims description 23
239000000203 mixture Substances 0.000 claims description 17
230000008569 process Effects 0.000 claims description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
125000000753 cycloalkyl group Chemical group 0.000 claims description 15
238000000354 decomposition reaction Methods 0.000 claims description 15
150000002576 ketones Chemical class 0.000 claims description 13
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 11
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 11
229910052742 iron Inorganic materials 0.000 claims description 10
MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 claims description 9
239000000463 material Substances 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 8
229910052748 manganese Inorganic materials 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
229910052804 chromium Inorganic materials 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
-1 porphyrin metal complex Chemical class 0.000 claims description 5
150000004696 coordination complex Chemical class 0.000 claims description 4
239000002002 slurry Substances 0.000 claims description 3
239000003054 catalyst Substances 0.000 description 20
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
150000001875 compounds Chemical class 0.000 description 11
230000008878 coupling Effects 0.000 description 10
238000010168 coupling process Methods 0.000 description 10
238000005859 coupling reaction Methods 0.000 description 10
150000004032 porphyrins Chemical class 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
239000011651 chromium Substances 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 8
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 7
239000001257 hydrogen Substances 0.000 description 7
239000011572 manganese Substances 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
150000002978 peroxides Chemical class 0.000 description 7
239000000377 silicon dioxide Substances 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000012876 carrier material Substances 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 5
229910017052 cobalt Inorganic materials 0.000 description 5
239000010941 cobalt Substances 0.000 description 5
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 5
150000002431 hydrogen Chemical class 0.000 description 5
125000002524 organometallic group Chemical group 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000004793 Polystyrene Substances 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000004821 distillation Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
150000002739 metals Chemical class 0.000 description 4
229920002223 polystyrene Polymers 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 4
230000007306 turnover Effects 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000000969 carrier Substances 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
239000010949 copper Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
229910052720 vanadium Inorganic materials 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
HQLPTNLVIRJYFA-UHFFFAOYSA-N 2-ethyl-7-methylnaphthalene Chemical compound C1=CC(C)=CC2=CC(CC)=CC=C21 HQLPTNLVIRJYFA-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
AFMVESZOYKHDBJ-UHFFFAOYSA-N fluoren-9-ol Chemical compound C1=CC=C2C(O)C3=CC=CC=C3C2=C1 AFMVESZOYKHDBJ-UHFFFAOYSA-N 0.000 description 2
YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
229910001510 metal chloride Inorganic materials 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
229910052723 transition metal Inorganic materials 0.000 description 2
150000003624 transition metals Chemical class 0.000 description 2
AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 2
XXUXKEUDSYKZAS-UHFFFAOYSA-N (2-butylphenyl)cycloheptane Chemical compound CCCCC1=CC=CC=C1C1CCCCCC1 XXUXKEUDSYKZAS-UHFFFAOYSA-N 0.000 description 1
MSNMIHDHQJVLHX-UHFFFAOYSA-N 1-hydroperoxy-2-propan-2-ylnaphthalene Chemical compound C1=CC=CC2=C(OO)C(C(C)C)=CC=C21 MSNMIHDHQJVLHX-UHFFFAOYSA-N 0.000 description 1
XBSRHLANXQMADK-UHFFFAOYSA-N 2-ethyl-1-hydroperoxy-7-methylnaphthalene Chemical compound C1=CC(C)=CC2=C(OO)C(CC)=CC=C21 XBSRHLANXQMADK-UHFFFAOYSA-N 0.000 description 1
XKOSZUFARRMESL-UHFFFAOYSA-N 2-ethyl-7-methylnaphthalen-1-ol Chemical compound C1=CC(C)=CC2=C(O)C(CC)=CC=C21 XKOSZUFARRMESL-UHFFFAOYSA-N 0.000 description 1
ISYHTRCUHPOGCS-UHFFFAOYSA-N 2-propan-2-ylnaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(C(C)C)=CC=C21 ISYHTRCUHPOGCS-UHFFFAOYSA-N 0.000 description 1
TVYVQNHYIHAJTD-UHFFFAOYSA-N 2-propan-2-ylnaphthalene Chemical compound C1=CC=CC2=CC(C(C)C)=CC=C21 TVYVQNHYIHAJTD-UHFFFAOYSA-N 0.000 description 1
SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical group CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
NYIDSUMRGUILGR-UHFFFAOYSA-N 4-(2-trimethoxysilylethyl)benzenesulfonyl chloride Chemical group CO[Si](OC)(OC)CCC1=CC=C(S(Cl)(=O)=O)C=C1 NYIDSUMRGUILGR-UHFFFAOYSA-N 0.000 description 1
BTHAEPAUPDJDIB-UHFFFAOYSA-N 9-hydroperoxy-9h-fluorene Chemical compound C1=CC=C2C(OO)C3=CC=CC=C3C2=C1 BTHAEPAUPDJDIB-UHFFFAOYSA-N 0.000 description 1
CYHOFESITORDDD-UHFFFAOYSA-M C(CCC)O[Cr](=O)(=O)O Chemical group C(CCC)O[Cr](=O)(=O)O CYHOFESITORDDD-UHFFFAOYSA-M 0.000 description 1
HJCNSOVRAZFJLK-UHFFFAOYSA-N C1=CC(C(=O)O)=CC=C1C1=CC2=CC([N]3)=CC=C3C=C(C=C3)NC3=CC([N]3)=CC=C3C=C1N2 Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC2=CC([N]3)=CC=C3C=C(C=C3)NC3=CC([N]3)=CC=C3C=C1N2 HJCNSOVRAZFJLK-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
229940053991 aldehydes and derivative Drugs 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
229940010552 ammonium molybdate Drugs 0.000 description 1
235000018660 ammonium molybdate Nutrition 0.000 description 1
239000011609 ammonium molybdate Substances 0.000 description 1
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
150000004056 anthraquinones Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QOJCIGAMMFVJRS-UHFFFAOYSA-N benzhydrylbenzene;hydrogen peroxide Chemical compound OO.C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 QOJCIGAMMFVJRS-UHFFFAOYSA-N 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000003426 co-catalyst Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
210000003298 dental enamel Anatomy 0.000 description 1
OYFJQPXVCSSHAI-QFPUQLAESA-N enalapril maleate Chemical compound OC(=O)\C=C/C(O)=O.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 OYFJQPXVCSSHAI-QFPUQLAESA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000012634 fragment Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
230000003100 immobilizing effect Effects 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
238000011068 loading method Methods 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
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 1
238000006263 metalation reaction Methods 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
ZQFWLIVWPCXOQT-UHFFFAOYSA-N phenylcycloheptane Chemical compound C1CCCCCC1C1=CC=CC=C1 ZQFWLIVWPCXOQT-UHFFFAOYSA-N 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
229920006391 phthalonitrile polymer Polymers 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
150000003623 transition metal compounds Chemical class 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- 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
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/08—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/14—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom belonging to a ring other than a six-membered aromatic ring
- 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
- 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
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes

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

NL9000893A 1990-04-14 1990-04-14 Werkwijze voor de bereiding van een cycloalkanon en/of cycloalkanol. NL9000893A (nl)

Priority Applications (13)

Application Number	Priority Date	Filing Date	Title
NL9000893A NL9000893A (nl)	1990-04-14	1990-04-14	Werkwijze voor de bereiding van een cycloalkanon en/of cycloalkanol.
EP91200831A EP0453021A1 (fr)	1990-04-14	1991-04-10	Procédé pour la préparation d'une cycloalcanone et/ou d'un cycloalcanol
MX025308A MX167121B (es)	1990-04-14	1991-04-11	Procedimiento para la preparacion de una cetona y un alcohol
HU911228A HUT56807A (en)	1990-04-14	1991-04-12	Process for producing cycloalkanone and/or cycloalkanole
PT97366A PT97366A (pt)	1990-04-14	1991-04-12	Processo de preparacao de uma cetona e/ou um alcool
AU74385/91A AU642724B2 (en)	1990-04-14	1991-04-12	Preparation of ketones and/or alcohols
CA002040378A CA2040378A1 (fr)	1990-04-14	1991-04-12	Methode de preparation d'une cycloalcanone et/ou d'un cycloalcalnol
JP3079758A JPH04224536A (ja)	1990-04-14	1991-04-12	ケトン及び／又はアルコールの製造法
SU914895077A RU2002725C1 (ru)	1990-04-14	1991-04-13	Способ разложени гидроперекиси в процессе получени кетона и/или спирта окислением кислородом циклического углеводорода
CN91103225A CN1056485A (zh)	1990-04-14	1991-04-13	环烷酮和/或环烷醇的制备方法
KR1019910006007A KR920005711A (ko)	1990-04-14	1991-04-15	사이클로 알카논 및/또는 사이클로알카놀의 제조방법
BR919101517A BR9101517A (pt)	1990-04-14	1991-04-15	Processo para preparar uma cetona e/ou um alcool
CS911064A CS106491A2 (en)	1990-04-14	1991-04-15	Method of cycloalkanone and/or cycloalkanole production

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL9000893		1990-04-14
NL9000893A NL9000893A (nl)	1990-04-14	1990-04-14	Werkwijze voor de bereiding van een cycloalkanon en/of cycloalkanol.

Publications (1)

Publication Number	Publication Date
NL9000893A true NL9000893A (nl)	1991-11-01

Family

ID=19856940

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL9000893A NL9000893A (nl)	1990-04-14	1990-04-14	Werkwijze voor de bereiding van een cycloalkanon en/of cycloalkanol.

Country Status (13)

Country	Link
EP (1)	EP0453021A1 (fr)
JP (1)	JPH04224536A (fr)
KR (1)	KR920005711A (fr)
CN (1)	CN1056485A (fr)
AU (1)	AU642724B2 (fr)
BR (1)	BR9101517A (fr)
CA (1)	CA2040378A1 (fr)
CS (1)	CS106491A2 (fr)
HU (1)	HUT56807A (fr)
MX (1)	MX167121B (fr)
NL (1)	NL9000893A (fr)
PT (1)	PT97366A (fr)
RU (1)	RU2002725C1 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5302709A (en) *	1992-11-25	1994-04-12	Board Of Trustees Operating Michigan State University	Polyaryl-metallic complex intercalated layered double hydroxides
US5345008A (en) *	1993-06-09	1994-09-06	Sun Company, Inc. (R&M)	Decomposition of organic hydroperoxides with nitrated porphyrin complexes
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
FR2802526B1 (fr) *	1999-12-17	2003-04-18	Rhodia Polyamide Intermediates	Procede de preparation de melanges alcools/cetones
JP4736368B2 (ja) *	2004-07-22	2011-07-27	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
CN101940948B (zh) *	2010-07-13	2012-07-04	中北大学	交联聚苯乙烯微球固载金属卟啉的方法
RU2470030C1 (ru) *	2011-11-21	2012-12-20	Федеральное государственное унитарное предприятие "Государственный научный центр "Научно-исследовательский институт органических полупродуктов и красителей" (ФГУП "ГНЦ "НИОПИК")	Катализатор и способ валентной изомеризации квадрициклана в норборнадиен

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1530986A (fr) *	1966-07-11	1968-06-28	Ici Ltd	Procédé d'oxydation d'hydrocarbures
US3816548A (en) *	1971-04-27	1974-06-11	Mobil Oil Corp	Catalytic oxidation process for isoparaffin hydrocarbons
NL8802592A (nl) *	1988-10-21	1990-05-16	Stamicarbon	Werkwijze voor de bereiding van een k/a-mengsel.

1990
- 1990-04-14 NL NL9000893A patent/NL9000893A/nl not_active Application Discontinuation
1991
- 1991-04-10 EP EP91200831A patent/EP0453021A1/fr not_active Withdrawn
- 1991-04-11 MX MX025308A patent/MX167121B/es unknown
- 1991-04-12 JP JP3079758A patent/JPH04224536A/ja active Pending
- 1991-04-12 AU AU74385/91A patent/AU642724B2/en not_active Expired - Fee Related
- 1991-04-12 CA CA002040378A patent/CA2040378A1/fr not_active Abandoned
- 1991-04-12 HU HU911228A patent/HUT56807A/hu unknown
- 1991-04-12 PT PT97366A patent/PT97366A/pt not_active Application Discontinuation
- 1991-04-13 CN CN91103225A patent/CN1056485A/zh active Pending
- 1991-04-13 RU SU914895077A patent/RU2002725C1/ru active
- 1991-04-15 KR KR1019910006007A patent/KR920005711A/ko not_active Withdrawn
- 1991-04-15 BR BR919101517A patent/BR9101517A/pt unknown
- 1991-04-15 CS CS911064A patent/CS106491A2/cs unknown

Also Published As

Publication number	Publication date
CS106491A2 (en)	1991-11-12
PT97366A (pt)	1992-01-31
AU642724B2 (en)	1993-10-28
JPH04224536A (ja)	1992-08-13
HUT56807A (en)	1991-10-28
KR920005711A (ko)	1992-04-03
CN1056485A (zh)	1991-11-27
EP0453021A1 (fr)	1991-10-23
BR9101517A (pt)	1991-12-03
MX167121B (es)	1993-03-04
AU7438591A (en)	1991-10-17
RU2002725C1 (ru)	1993-11-15
CA2040378A1 (fr)	1991-10-15

Legal Events

Date	Code	Title	Description
1991-11-01	A1B	A search report has been drawn up
1992-12-01	BV	The patent application has lapsed

Publication	Publication Date	Title
NL8802592A (nl)	1990-05-16	Werkwijze voor de bereiding van een k/a-mengsel.
EP0532327B1 (fr)	1996-04-17	Cyano- et polycyanométalloporphyrines comme catalyseurs pour l'oxydation d'alcanes
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Chisem et al.	1998	Catalytic oxidation of alkyl aromatics using a novel silica supported Schiff base complex
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