CS106491A2 - Method of cycloalkanone and/or cycloalkanole production - Google Patents

Method of cycloalkanone and/or cycloalkanole production Download PDF

Info

Publication number: CS106491A2
Authority: CS; Czechoslovakia
Prior art keywords: hydroperoxide; weight; oxidation; catalyst; metal
Prior art date: 1990-04-14

Application number

CS911064A

Other languages

Czech (cs)

English (en)

Inventor

Henricus Anna Christiaan Baur

Ubaldus Franciscus Kragten

Wilhelmus Petrus Wolvers

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

1991-04-15

Publication date

1991-11-12

1991-04-15 Application filed by Stamicarbon filed Critical Stamicarbon

1991-11-12 Publication of CS106491A2 publication Critical patent/CS106491A2/cs

Links

238000000034 method Methods 0.000 title claims description 26
238000004519 manufacturing process Methods 0.000 title description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 26
238000007254 oxidation reaction Methods 0.000 claims description 22
230000003647 oxidation Effects 0.000 claims description 21
229910052751 metal Inorganic materials 0.000 claims description 19
239000002184 metal Substances 0.000 claims description 19
239000000203 mixture Substances 0.000 claims description 16
125000000753 cycloalkyl group Chemical group 0.000 claims description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
229910017052 cobalt Inorganic materials 0.000 claims description 14
239000010941 cobalt Substances 0.000 claims description 14
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 14
238000000354 decomposition reaction Methods 0.000 claims description 14
229910052742 iron Inorganic materials 0.000 claims description 13
-1 porphyrin metal complex Chemical class 0.000 claims description 13
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
150000002576 ketones Chemical class 0.000 claims description 11
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 9
229910052804 chromium Inorganic materials 0.000 claims description 9
239000011651 chromium Substances 0.000 claims description 9
MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 claims description 8
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 8
150000004696 coordination complex Chemical class 0.000 claims description 4
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 claims description 4
239000000463 material Substances 0.000 claims description 3
239000002002 slurry Substances 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
239000000956 alloy Substances 0.000 claims 1
229910045601 alloy Inorganic materials 0.000 claims 1
239000003054 catalyst Substances 0.000 description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
150000001875 compounds Chemical class 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
150000004032 porphyrins Chemical class 0.000 description 9
239000000047 product Substances 0.000 description 9
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 8
150000002978 peroxides Chemical class 0.000 description 8
125000004435 hydrogen atom Chemical class [H]* 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
239000000377 silicon dioxide Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
125000002524 organometallic group Chemical group 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
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000004821 distillation Methods 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
229910052748 manganese Inorganic materials 0.000 description 4
239000011572 manganese Substances 0.000 description 4
150000002739 metals Chemical class 0.000 description 4
230000001590 oxidative effect Effects 0.000 description 4
229920002223 polystyrene Polymers 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 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
239000004215 Carbon black (E152) Substances 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
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
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
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
239000002245 particle Substances 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
IJGGQBIUSGOOCA-UHFFFAOYSA-N 1,8-Dimethyl-fluoren Natural products C12=CC=CC(C)=C2CC2=C1C=CC=C2C IJGGQBIUSGOOCA-UHFFFAOYSA-N 0.000 description 2
XXPBFNVKTVJZKF-UHFFFAOYSA-N 9,10-dihydrophenanthrene Chemical compound C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 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
125000004429 atom Chemical group 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000012876 carrier material Substances 0.000 description 2
MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical class [Co+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 MPMSMUBQXQALQI-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 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
229910052757 nitrogen Inorganic materials 0.000 description 2
ZQFWLIVWPCXOQT-UHFFFAOYSA-N phenylcycloheptane Chemical compound C1CCCCCC1C1=CC=CC=C1 ZQFWLIVWPCXOQT-UHFFFAOYSA-N 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
239000007787 solid Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000004408 titanium dioxide Substances 0.000 description 2
ZYFTVCJVNRKBCC-UHFFFAOYSA-N 1-(2-methylpropyl)naphthalene Chemical compound C1=CC=C2C(CC(C)C)=CC=CC2=C1 ZYFTVCJVNRKBCC-UHFFFAOYSA-N 0.000 description 1
GKEUODMJRFDLJY-UHFFFAOYSA-N 1-Methylfluorene Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2C GKEUODMJRFDLJY-UHFFFAOYSA-N 0.000 description 1
PCMIWASLPQNSCD-UHFFFAOYSA-N 1-cyclohexyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C1CCCCC1 PCMIWASLPQNSCD-UHFFFAOYSA-N 0.000 description 1
DLMYHUARHITGIJ-UHFFFAOYSA-N 1-ethyl-2-phenylbenzene Chemical group CCC1=CC=CC=C1C1=CC=CC=C1 DLMYHUARHITGIJ-UHFFFAOYSA-N 0.000 description 1
HUXKTWJQSHBZIV-UHFFFAOYSA-N 1-ethyl-3-phenylbenzene Chemical group CCC1=CC=CC(C=2C=CC=CC=2)=C1 HUXKTWJQSHBZIV-UHFFFAOYSA-N 0.000 description 1
YDVWQCIKLMZJOV-UHFFFAOYSA-N 1-ethyl-4-methylnaphthalene Chemical compound C1=CC=C2C(CC)=CC=C(C)C2=C1 YDVWQCIKLMZJOV-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
HKTCLPBBJDIBGF-UHFFFAOYSA-N 1-phenyl-2-propan-2-ylbenzene Chemical group CC(C)C1=CC=CC=C1C1=CC=CC=C1 HKTCLPBBJDIBGF-UHFFFAOYSA-N 0.000 description 1
BSZXAFXFTLXUFV-UHFFFAOYSA-N 1-phenylethylbenzene Chemical compound C=1C=CC=CC=1C(C)C1=CC=CC=C1 BSZXAFXFTLXUFV-UHFFFAOYSA-N 0.000 description 1
KMHSUNDEGHRBNV-UHFFFAOYSA-N 2,4-dichloropyrimidine-5-carbonitrile Chemical class ClC1=NC=C(C#N)C(Cl)=N1 KMHSUNDEGHRBNV-UHFFFAOYSA-N 0.000 description 1
OHLHYHRZBBMYPE-UHFFFAOYSA-N 2-(2-methylpropyl)naphthalene Chemical compound C1=CC=CC2=CC(CC(C)C)=CC=C21 OHLHYHRZBBMYPE-UHFFFAOYSA-N 0.000 description 1
IBLVSWYGUFGDMF-UHFFFAOYSA-N 2-cyclohexylethylcyclohexane Chemical compound C1CCCCC1CCC1CCCCC1 IBLVSWYGUFGDMF-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
HQLPTNLVIRJYFA-UHFFFAOYSA-N 2-ethyl-7-methylnaphthalene Chemical compound C1=CC(C)=CC2=CC(CC)=CC=C21 HQLPTNLVIRJYFA-UHFFFAOYSA-N 0.000 description 1
QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-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
LQBNOHAXLHRIQW-UHFFFAOYSA-N 2-propylnaphthalene Chemical compound C1=CC=CC2=CC(CCC)=CC=C21 LQBNOHAXLHRIQW-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
OHCIGDABVRPEJW-UHFFFAOYSA-N 6-phenyl-1,2,3,4-tetrahydronaphthalene Chemical compound C=1C=C2CCCCC2=CC=1C1=CC=CC=C1 OHCIGDABVRPEJW-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
238000004438 BET method Methods 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
239000004698 Polyethylene Substances 0.000 description 1
229910000831 Steel Inorganic materials 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
QRSFFHRCBYCWBS-UHFFFAOYSA-N [O].[O] Chemical compound [O].[O] QRSFFHRCBYCWBS-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 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
125000003277 amino group Chemical group 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
150000008064 anhydrides Chemical class 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
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 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
238000009835 boiling Methods 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
239000007795 chemical reaction product 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
238000001816 cooling Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
150000003997 cyclic ketones Chemical class 0.000 description 1
125000002993 cycloalkylene group Chemical group 0.000 description 1
XXKOQQBKBHUATC-UHFFFAOYSA-N cyclohexylmethylcyclohexane Chemical compound C1CCCCC1CC1CCCCC1 XXKOQQBKBHUATC-UHFFFAOYSA-N 0.000 description 1
210000003298 dental enamel Anatomy 0.000 description 1
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000005038 ethylene vinyl acetate Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000002349 favourable effect Effects 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
RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 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
229910001510 metal chloride Inorganic materials 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
NKFNKCQNUBQGQP-UHFFFAOYSA-N phenylcyclododecane Chemical compound C1CCCCCCCCCCC1C1=CC=CC=C1 NKFNKCQNUBQGQP-UHFFFAOYSA-N 0.000 description 1
NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical compound NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-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
229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000010959 steel Substances 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003623 transition metal compounds Chemical class 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
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 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

Landscapes

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)

CS911064A 1990-04-14 1991-04-15 Method of cycloalkanone and/or cycloalkanole production CS106491A2 (en)

Applications Claiming Priority (1)

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.

Publications (1)

Publication Number	Publication Date
CS106491A2 true CS106491A2 (en)	1991-11-12

Family

ID=19856940

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS911064A CS106491A2 (en)	1990-04-14	1991-04-15	Method of cycloalkanone and/or cycloalkanole production

Country Status (13)

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

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
EP1012130B9 (en) *	1997-02-11	2003-05-02	E.I. Du Pont De Nemours And Company	Hydroperoxide decomposition process
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/en not_active Withdrawn
- 1991-04-11 MX MX025308A patent/MX167121B/es unknown
- 1991-04-12 PT PT97366A patent/PT97366A/pt not_active Application Discontinuation
- 1991-04-12 CA CA002040378A patent/CA2040378A1/en not_active Abandoned
- 1991-04-12 JP JP3079758A patent/JPH04224536A/ja active Pending
- 1991-04-12 HU HU911228A patent/HUT56807A/hu unknown
- 1991-04-12 AU AU74385/91A patent/AU642724B2/en not_active Expired - Fee Related
- 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 CS CS911064A patent/CS106491A2/cs unknown
- 1991-04-15 BR BR919101517A patent/BR9101517A/pt unknown

Also Published As

Publication number	Publication date
NL9000893A (nl)	1991-11-01
CA2040378A1 (en)	1991-10-15
HUT56807A (en)	1991-10-28
CN1056485A (zh)	1991-11-27
MX167121B (es)	1993-03-04
EP0453021A1 (en)	1991-10-23
KR920005711A (ko)	1992-04-03
BR9101517A (pt)	1991-12-03
AU642724B2 (en)	1993-10-28
JPH04224536A (ja)	1992-08-13
AU7438591A (en)	1991-10-17
PT97366A (pt)	1992-01-31
RU2002725C1 (ru)	1993-11-15

Publication	Publication Date	Title
Salavati-Niasari et al.	2003	Alumina-supported Mn (II), Co (II), Ni (II) and Cu (II) bis (2-hydroxyanil) acetylacetone complexes as catalysts for the oxidation of cyclohexene with tert-butylhydroperoxide
Rafelt et al.	2000	Recent advances in the partial oxidation of organic molecules using heterogeneous catalysis
JP3386827B2 (ja)	2003-03-17	アルカノンおよび／またはアルカノール含有混合物の製造方法
US5004837A (en)	1991-04-02	Process for preparing a cycloalkanone and/or cycloalkanol
NL1004636C2 (nl)	1998-03-20	Werkwijze voor het voortbrengen van propeenoxyde.
Becerra et al.	2016	Kinetic study of α-pinene allylic oxidation over FePcCl16-NH2-SiO2 catalyst
Chisem et al.	1998	Catalytic oxidation of alkyl aromatics using a novel silica supported Schiff base complex
Abbo et al.	2009	Di-, tri-and tetra-valent ion-exchanged NaY zeolite: Active heterogeneous catalysts for hydroxylation of benzene and phenol
CS106491A2 (en)	1991-11-12	Method of cycloalkanone and/or cycloalkanole production
Li et al.	2013	Encapsulation of tetraazamacrocyclic complexes of cobalt (II), copper (II) and oxovanadium (IV) in zeolite-Y and their use as catalysts for the oxidation of styrene
CN101626835B (zh)	2013-04-24	环状酰亚胺固定化催化剂、及用该催化剂的有机化合物氧化方法
CN114787114A (zh)	2022-07-22	使用co2的甲醇光催化氢羧基化以生产乙酸的改进工艺
Mehta et al.	2017	Synthesis, characterization and catalytic activity of zeolite-Y immobilized oxovanadium complex on Bayer-Villiger oxidation
AU683622B2 (en)	1997-11-20	Peracid compounds
US7994330B2 (en)	2011-08-09	Method for producing organic compound and method for decomposing compound having dicarboximide skeleton
Hamid	2004	Comparative Study of Iron Porphyrin Supported on Mesoporous Al-MCM-41 and Poly (methacrylic acid)(PMAA): Characterization and Their Catalytic Activities
EP1870394A1 (en)	2007-12-26	Method for producing organic compound and method for decomposing compound having dicarboxyimide skeleton
JP2006273722A (ja)	2006-10-12	有機化合物の製造方法