PL188039B1 - Sposób rozkładu mieszaniny zawierającej wodoronadtlenek cykloalkilu - Google Patents

Sposób rozkładu mieszaniny zawierającej wodoronadtlenek cykloalkilu

Info

Publication number: PL188039B1
Authority: PL; Poland
Prior art keywords: alkali metal; mmol; aqueous phase; chhp; decomposition
Prior art date: 1995-10-13

Application number

PL31649096A

Other languages

English (en)

Polish (pl)

Other versions

PL316490A1 (en

Inventor

Ubaldus Franciscus Kragten

Henricus Anna Christiaan Baur

Johannes Gerardus Hubertus Maria Housmans

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.)

1995-10-13

Filing date

1996-10-11

Publication date

2004-11-30

1996-10-11 Application filed by Dsm Nv filed Critical Dsm Nv

1997-04-14 Publication of PL316490A1 publication Critical patent/PL316490A1/xx

2004-11-30 Publication of PL188039B1 publication Critical patent/PL188039B1/pl

Links

-1 cycloalkyl hydroperoxide Chemical compound 0.000 title claims abstract description 40
238000000034 method Methods 0.000 title claims abstract description 29
239000000203 mixture Substances 0.000 claims abstract description 34
239000008346 aqueous phase Substances 0.000 claims abstract description 31
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 13
150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 12
239000002253 acid Substances 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
150000001735 carboxylic acids Chemical class 0.000 claims abstract description 5
150000007513 acids Chemical class 0.000 claims abstract description 3
229910000288 alkali metal carbonate Inorganic materials 0.000 claims abstract description 3
150000008041 alkali metal carbonates Chemical class 0.000 claims abstract description 3
238000000354 decomposition reaction Methods 0.000 claims description 37
229910052723 transition metal Inorganic materials 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 8
229910052708 sodium Inorganic materials 0.000 claims description 5
239000011734 sodium Substances 0.000 claims description 5
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 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
150000002500 ions Chemical class 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
239000011591 potassium Substances 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
150000001875 compounds Chemical class 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 84
FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 51
238000007254 oxidation reaction Methods 0.000 description 29
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 28
230000003647 oxidation Effects 0.000 description 28
238000006243 chemical reaction Methods 0.000 description 20
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 15
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 14
238000004448 titration Methods 0.000 description 13
230000015556 catabolic process Effects 0.000 description 11
238000006731 degradation reaction Methods 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000011651 chromium Substances 0.000 description 8
150000001924 cycloalkanes Chemical class 0.000 description 8
229910000029 sodium carbonate Inorganic materials 0.000 description 7
235000017550 sodium carbonate Nutrition 0.000 description 7
KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
230000000052 comparative effect Effects 0.000 description 5
150000001991 dicarboxylic acids Chemical class 0.000 description 5
239000000243 solution Substances 0.000 description 5
239000012071 phase Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
229910052804 chromium Inorganic materials 0.000 description 3
229910017052 cobalt Inorganic materials 0.000 description 3
239000010941 cobalt Substances 0.000 description 3
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000011521 glass Substances 0.000 description 3
239000007791 liquid phase Substances 0.000 description 3
150000002763 monocarboxylic acids Chemical class 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000001632 sodium acetate Substances 0.000 description 3
235000017281 sodium acetate Nutrition 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
150000003624 transition metals Chemical class 0.000 description 3
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
229910000831 Steel Inorganic materials 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
239000010959 steel Substances 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
238000005882 aldol condensation reaction Methods 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
239000007864 aqueous solution Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
150000001734 carboxylic acid salts Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
108010073890 crustacean hyperglycemic hormone precursor Proteins 0.000 description 1
DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 description 1
WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
239000004914 cyclooctane Substances 0.000 description 1
210000003298 dental enamel Anatomy 0.000 description 1
238000007865 diluting Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000007701 flash-distillation Methods 0.000 description 1
239000013505 freshwater Substances 0.000 description 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
150000002432 hydroperoxides Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000007788 liquid Substances 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
239000000463 material Substances 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
229910052715 tantalum Inorganic materials 0.000 description 1
GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
229940005605 valeric acid Drugs 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
- 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
- C07C407/00—Preparation of peroxy compounds
- 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
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

Landscapes

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

PL31649096A 1995-10-13 1996-10-11 Sposób rozkładu mieszaniny zawierającej wodoronadtlenek cykloalkilu PL188039B1 (pl)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
BE9500853A BE1009662A3 (nl)	1995-10-13	1995-10-13	Werkwijze voor het ontleden van cycloalkylhydroperoxide.

Publications (2)

Publication Number	Publication Date
PL316490A1 PL316490A1 (en)	1997-04-14
PL188039B1 true PL188039B1 (pl)	2004-11-30

Family

ID=3889235

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PL31649096A PL188039B1 (pl)	1995-10-13	1996-10-11	Sposób rozkładu mieszaniny zawierającej wodoronadtlenek cykloalkilu

Country Status (22)

Country	Link
US (1)	US5905173A (2)
EP (1)	EP0768292B1 (2)
JP (1)	JP3897384B2 (2)
KR (1)	KR100446374B1 (2)
CN (1)	CN1062259C (2)
AR (1)	AR003877A1 (2)
AU (1)	AU700696B2 (2)
BE (1)	BE1009662A3 (2)
BR (1)	BR9605132A (2)
CA (1)	CA2187709C (2)
CO (1)	CO4560461A1 (2)
CZ (1)	CZ296696A3 (2)
DE (1)	DE69606128T2 (2)
ES (1)	ES2143714T3 (2)
HU (1)	HU216540B (2)
IL (1)	IL119410A (2)
MX (1)	MX9604783A (2)
PL (1)	PL188039B1 (2)
RU (1)	RU2185366C2 (2)
SK (1)	SK282415B6 (2)
TW (1)	TW338762B (2)
ZA (1)	ZA968565B (2)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE1011041A3 (nl) *	1997-03-12	1999-04-06	Dsm Nv	Werkwijze voor het ontleden van cycloalkylhydroperoxide.
CA2406001A1 (en) *	2000-04-14	2001-10-25	American Express Travel Related Services Company, Inc.	A system and method for using loyalty points
US6700022B2 (en) *	2002-06-05	2004-03-02	E. I. Du Pont De Nemours And Company	High yield cyclohexyl hydroperoxide decompostition process
WO2006033740A1 (en) *	2004-08-24	2006-03-30	Invista Technologies S.A.R.L.	Method for reducing cyclohexenone content of a cyclohexenone-containing organic mixture
EP1841720B1 (en) *	2005-01-25	2009-03-25	DSMIP Assets B.V.	Process for preparing cyclohexanone and cyclohexanol
US8376224B2 (en)	2006-05-25	2013-02-19	Sean I. Mcghie	Self-service stations for utilizing non-negotiable credits earned from a game of chance
EP2096097B1 (en) *	2006-12-05	2012-08-22	Daicel Chemical Industries, Ltd.	Method for producing oxidation product of cycloalkane
CN103372462B (zh) *	2012-04-26	2016-03-23	中国科学院大连化学物理研究所	一种分解环烷基过氧化氢水溶性催化剂体系及应用
CN105339332B (zh) *	2013-04-18	2018-04-10	罗地亚经营管理公司	环烷烃氧化催化剂以及生产醇和酮的方法
JP6565926B2 (ja)	2014-10-31	2019-09-04	宇部興産株式会社	ケトン及び／又はアルコールの製造方法及びそのシステム
WO2017099072A1 (ja)	2015-12-07	2017-06-15	宇部興産株式会社	ケトン及び／又はアルコールの製造方法及びそのシステム

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2127520A1 (de) *	1971-06-03	1972-12-14	Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen	Verfahren zur Herstellung von Cycloalkanol- und Cycloalkanon-Gemischen
US4163027A (en) *	1976-11-06	1979-07-31	Basf Aktiengesellschaft	Working-up of reaction mixtures containing cyclohexanol and cyclohexanone
NL7802125A (nl) *	1978-02-25	1979-08-28	Stamicarbon	Werkwijze voor het bereiden van cycloalkanolen en cycloalkanonen.
JPS5738735A (en) *	1980-08-19	1982-03-03	Mitsui Petrochem Ind Ltd	Method for treating hydroperoxide mixture
NL8201695A (nl) *	1982-04-23	1983-11-16	Stamicarbon	Werkwijze voor de bereiding van cyclohexanol en cyclohexanon.
US5206441A (en) *	1992-04-06	1993-04-27	E. I. Du Pont De Nemours And Company	High rate process for preparation of cyclohexanol and cyclohexanone
BE1007904A3 (nl) *	1993-12-23	1995-11-14	Dsm Nv	Werkwijze voor de bereiding van een alkanol en/of een alkanon.

1995
- 1995-10-13 BE BE9500853A patent/BE1009662A3/nl not_active IP Right Cessation
1996
- 1996-10-03 DE DE69606128T patent/DE69606128T2/de not_active Expired - Lifetime
- 1996-10-03 EP EP96202754A patent/EP0768292B1/en not_active Expired - Lifetime
- 1996-10-03 ES ES96202754T patent/ES2143714T3/es not_active Expired - Lifetime
- 1996-10-09 CO CO96053676A patent/CO4560461A1/es unknown
- 1996-10-09 SK SK1290-96A patent/SK282415B6/sk not_active IP Right Cessation
- 1996-10-10 ZA ZA968565A patent/ZA968565B/xx unknown
- 1996-10-10 CZ CZ962966A patent/CZ296696A3/cs unknown
- 1996-10-11 IL IL11941096A patent/IL119410A/xx not_active IP Right Cessation
- 1996-10-11 US US08/729,511 patent/US5905173A/en not_active Expired - Lifetime
- 1996-10-11 PL PL31649096A patent/PL188039B1/pl not_active IP Right Cessation
- 1996-10-11 RU RU96120364/04A patent/RU2185366C2/ru not_active IP Right Cessation
- 1996-10-11 CA CA002187709A patent/CA2187709C/en not_active Expired - Fee Related
- 1996-10-11 HU HU9602820A patent/HU216540B/hu not_active IP Right Cessation
- 1996-10-11 MX MX9604783A patent/MX9604783A/es unknown
- 1996-10-12 KR KR1019960046012A patent/KR100446374B1/ko not_active Expired - Fee Related
- 1996-10-12 TW TW085112474A patent/TW338762B/zh not_active IP Right Cessation
- 1996-10-12 CN CN96121086A patent/CN1062259C/zh not_active Expired - Fee Related
- 1996-10-14 BR BR9605132A patent/BR9605132A/pt not_active IP Right Cessation
- 1996-10-14 JP JP30541496A patent/JP3897384B2/ja not_active Expired - Fee Related
- 1996-10-14 AU AU68184/96A patent/AU700696B2/en not_active Ceased
- 1996-10-14 AR ARP960104732A patent/AR003877A1/es not_active Application Discontinuation

Also Published As

Publication number	Publication date
HU216540B (hu)	1999-07-28
CN1062259C (zh)	2001-02-21
JP3897384B2 (ja)	2007-03-22
CZ296696A3 (en)	1997-06-11
ZA968565B (en)	1997-05-13
AR003877A1 (es)	1998-09-09
KR100446374B1 (ko)	2004-11-03
CO4560461A1 (es)	1998-02-10
ES2143714T3 (es)	2000-05-16
HUP9602820A3 (en)	1998-04-28
AU700696B2 (en)	1999-01-14
SK282415B6 (sk)	2002-01-07
BE1009662A3 (nl)	1997-06-03
HU9602820D0 (en)	1996-11-28
BR9605132A (pt)	1998-07-07
IL119410A (en)	2000-11-21
CA2187709A1 (en)	1997-04-14
US5905173A (en)	1999-05-18
SK129096A3 (en)	1997-05-07
EP0768292A1 (en)	1997-04-16
JPH09194408A (ja)	1997-07-29
HUP9602820A2 (en)	1997-05-28
IL119410A0 (en)	1997-01-10
TW338762B (en)	1998-08-21
KR970021046A (ko)	1997-05-28
MX9604783A (es)	1997-08-30
AU6818496A (en)	1997-04-17
EP0768292B1 (en)	2000-01-12
RU2185366C2 (ru)	2002-07-20
DE69606128D1 (de)	2000-02-17
CN1156714A (zh)	1997-08-13
DE69606128T2 (de)	2000-08-31
CA2187709C (en)	2005-03-29
PL316490A1 (en)	1997-04-14

Legal Events

Date	Code	Title	Description
2015-12-31	LAPS	Decisions on the lapse of the protection rights	Effective date: 20141011

Publication	Publication Date	Title
US5859301A (en)	1999-01-12	Process for preparing alkanones and alkanols
EP0092867B1 (en)	1986-07-16	Process for preparing cyclohexanol and cyclohexanone
EP0768292B1 (en)	2000-01-12	Process for decomposing cycloalkyl hydroperoxide
RU2208605C1 (ru)	2003-07-20	Способ окисления углеводородов, спиртов и/или кетонов
MXPA96004783A (en)	1997-08-01	Procedimeitno decomponer decicloalqu hidroperoxido
CN101107210A (zh)	2008-01-16	制备环己酮和环己醇的工艺
EP0634993B1 (en)	1997-09-17	High rate process for preparation of cyclohexanol and cyclohexanone
JP2001233809A (ja)	2001-08-28	炭化水素類の酸化方法
US6700022B2 (en)	2004-03-02	High yield cyclohexyl hydroperoxide decompostition process
EP1350786B1 (en)	2008-08-13	Process for production of dicarboxylic acids
US7019167B2 (en)	2006-03-28	Process for producing alkanedicarboxylic acid
US5406001A (en)	1995-04-11	Method for the continuous preparation of a mixture of a cycloalkanone, a cycloalkanol and a cycloalkylhydroperoxide
RU2235714C1 (ru)	2004-09-10	Способ окисления углеводородов, спиртов и/или кетонов
EP1471047B1 (en)	2012-08-08	Process for producing dicarboxylic acid
JP2841696B2 (ja)	1998-12-24	シクロヘキサノンとシクロヘキサノールの製造方法
US4704476A (en)	1987-11-03	Working up reaction mixtures containing cyclohexyl hydro-peroxide, cyclohexanol and cyclohexanone
EP2365953A1 (en)	2011-09-21	Catalysed cyclohexane oxidation
WO2006066904A1 (en)	2006-06-29	Process for decomposing cyclohexylhdroperoxide
JP5558581B2 (ja)	2014-07-23	脱過酸化触媒の製造方法
SK123799A3 (en)	2000-05-16	Process for decomposing cycloalkylhydroperoxide
SK6622003A3 (en)	2004-02-03	Method of oxidation of cyclohexane
JPS6140242A (ja)	1986-02-26	アシルオキシ・ナフトエ酸の製造法