NL8201695A - Werkwijze voor de bereiding van cyclohexanol en cyclohexanon. - Google Patents

Werkwijze voor de bereiding van cyclohexanol en cyclohexanon. Download PDF

Info

Publication number: NL8201695A
Authority: NL; Netherlands
Prior art keywords: oxidation; cyclohexanol; treatment; oxidation mixture; cyclohexanone
Prior art date: 1982-04-23

Application number

NL8201695A

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.)

1982-04-23

Filing date

1982-04-23

Publication date

1983-11-16

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=19839643&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NL8201695(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1982-04-23 Application filed by Stamicarbon filed Critical Stamicarbon

1982-04-23 Priority to NL8201695A priority Critical patent/NL8201695A/nl

1983-04-15 Priority to DE8383200544T priority patent/DE3364495D1/de

1983-04-15 Priority to EP83200544A priority patent/EP0092867B1/de

1983-04-22 Priority to KR1019830001703A priority patent/KR870000056B1/ko

1983-04-22 Priority to BR8302088A priority patent/BR8302088A/pt

1983-04-22 Priority to PT76592A priority patent/PT76592B/pt

1983-04-22 Priority to JP58071321A priority patent/JPH0615484B2/ja

1983-04-22 Priority to ES521744A priority patent/ES8402249A1/es

1983-04-22 Priority to CA000426474A priority patent/CA1244475A/en

1983-04-25 Priority to MX699883A priority patent/MX154866A/es

1983-11-16 Publication of NL8201695A publication Critical patent/NL8201695A/nl

Links

JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title claims description 34
238000000034 method Methods 0.000 title claims description 18
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 title claims description 17
238000002360 preparation method Methods 0.000 title claims description 5
230000003647 oxidation Effects 0.000 claims description 31
238000007254 oxidation reaction Methods 0.000 claims description 31
238000000354 decomposition reaction Methods 0.000 claims description 23
239000000203 mixture Substances 0.000 claims description 20
239000008346 aqueous phase Substances 0.000 claims description 12
229910052751 metal Inorganic materials 0.000 claims description 12
239000002184 metal Substances 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 12
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 7
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 7
239000012074 organic phase Substances 0.000 claims description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 5
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
239000007864 aqueous solution Substances 0.000 claims description 4
229910001882 dioxygen Inorganic materials 0.000 claims description 3
239000007789 gas Substances 0.000 claims description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
239000012071 phase Substances 0.000 claims description 2
238000010992 reflux Methods 0.000 claims description 2
150000001868 cobalt Chemical class 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 5
239000000243 solution Substances 0.000 description 5
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
229910052804 chromium Inorganic materials 0.000 description 4
239000011651 chromium Substances 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000003518 caustics Substances 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
KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
229940044175 cobalt sulfate Drugs 0.000 description 2
229910000361 cobalt sulfate Inorganic materials 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
229920002292 Nylon 6 Polymers 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
-1 aluminum-20 nium Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
QAEKNCDIHIGLFI-UHFFFAOYSA-L cobalt(2+);2-ethylhexanoate Chemical compound [Co+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O QAEKNCDIHIGLFI-UHFFFAOYSA-L 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
210000003298 dental enamel Anatomy 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000011521 glass Substances 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese 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
239000000178 monomer Substances 0.000 description 1
GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 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
238000005406 washing Methods 0.000 description 1

Classifications

- 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
- 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
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

NL8201695A 1982-04-23 1982-04-23 Werkwijze voor de bereiding van cyclohexanol en cyclohexanon. NL8201695A (nl)

Priority Applications (10)

Application Number	Priority Date	Filing Date	Title
NL8201695A NL8201695A (nl)	1982-04-23	1982-04-23	Werkwijze voor de bereiding van cyclohexanol en cyclohexanon.
DE8383200544T DE3364495D1 (en)	1982-04-23	1983-04-15	Process for preparing cyclohexanol and cyclohexanone
EP83200544A EP0092867B1 (de)	1982-04-23	1983-04-15	Verfahren zur Herstellung von Cyclohexanol und Cyclohexanon
CA000426474A CA1244475A (en)	1982-04-23	1983-04-22	Process for preparing cyclohexanol and cyclohexanone
BR8302088A BR8302088A (pt)	1982-04-23	1983-04-22	Processo para preparar cicloexanol e cicloexanona
KR1019830001703A KR870000056B1 (ko)	1982-04-23	1983-04-22	사이클로 헥사놀 및 사이클로 헥사논의 제조방법
PT76592A PT76592B (en)	1982-04-23	1983-04-22	Process for preparing cyclohexanol and cyclohexanone
JP58071321A JPH0615484B2 (ja)	1982-04-23	1983-04-22	シクロヘキサノール及びシクロヘキサノンの製造方法
ES521744A ES8402249A1 (es)	1982-04-23	1983-04-22	Procedimiento para preparar ciclohexanol y ciclohexanona.
MX699883A MX154866A (es)	1982-04-23	1983-04-25	Procedimiento mejorado para preparar ciclohexanol y ciclohexanona

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL8201695A NL8201695A (nl)	1982-04-23	1982-04-23	Werkwijze voor de bereiding van cyclohexanol en cyclohexanon.
NL8201695		1982-04-23

Publications (1)

Publication Number	Publication Date
NL8201695A true NL8201695A (nl)	1983-11-16

Family

ID=19839643

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8201695A NL8201695A (nl)	1982-04-23	1982-04-23	Werkwijze voor de bereiding van cyclohexanol en cyclohexanon.

Country Status (9)

Country	Link
EP (1)	EP0092867B1 (de)
JP (1)	JPH0615484B2 (de)
KR (1)	KR870000056B1 (de)
BR (1)	BR8302088A (de)
CA (1)	CA1244475A (de)
DE (1)	DE3364495D1 (de)
ES (1)	ES8402249A1 (de)
NL (1)	NL8201695A (de)
PT (1)	PT76592B (de)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3513568A1 (de) *	1985-04-16	1986-10-16	Basf Ag, 6700 Ludwigshafen	Verfahren zur aufarbeitung von cyclohexanol, cyclohexanon sowie cyclohexylhydroperoxid enthaltenden reaktionsgemischen
DE3601218A1 (de) *	1986-01-17	1987-07-23	Basf Ag	Verfahren zur aufarbeitung von cyclohexylhydroperoxid, cyclohexanol und cyclohexanon enthaltenden reaktionsgemischen
JP2562150B2 (ja) *	1986-10-23	1996-12-11	バスフアクチェンゲゼルシャフト	シクロヘキシルヒドロペルオキシドを含有する反応混合物の後処理法
DE4104419A1 (de) *	1991-02-14	1992-08-20	Basf Ag	Kreislaufverfahren zur herstellung von cyclohexenoxid sowie cyclohexanol und cyclohexanon
BE1007904A3 (nl) *	1993-12-23	1995-11-14	Dsm Nv	Werkwijze voor de bereiding van een alkanol en/of een alkanon.
BE1009662A3 (nl) *	1995-10-13	1997-06-03	Dsm Nv	Werkwijze voor het ontleden van cycloalkylhydroperoxide.
BE1011041A3 (nl) *	1997-03-12	1999-04-06	Dsm Nv	Werkwijze voor het ontleden van cycloalkylhydroperoxide.
US5892122A (en) *	1997-08-25	1999-04-06	E. I. Du Pont De Nemours And Company	Method for making cyclohexanol and cyclohexanone
US6700022B2 (en) *	2002-06-05	2004-03-02	E. I. Du Pont De Nemours And Company	High yield cyclohexyl hydroperoxide decompostition process
JP2008524298A (ja) *	2004-12-22	2008-07-10	ディーエスエムアイピーアセッツビー．ブイ．	シクロヘキシルハイドロパーオキサイドの分解方法
KR101310409B1 (ko)	2005-01-25	2013-09-23	디에스엠 아이피 어셋츠 비.브이.	사이클로헥산온 및 사이클로헥산올의 제조 방법
TW200944497A (en) *	2008-04-17	2009-11-01	China Petrochemical Dev Corp	System and method for producing naphthenone
CN101607875B (zh) *	2008-06-17	2012-07-25	中国石油化学工业开发股份有限公司	制造环烷酮的方法
FR2952055B1 (fr) *	2009-11-05	2011-11-11	Rhodia Operations	Procede de preparation de composes hydroperoxyde d'alkyle
WO2013083512A1 (en)	2011-12-07	2013-06-13	Dsm Ip Assets B.V.	Process for the production of a mixture comprising cyclohexanol and cyclohexanone
WO2013083513A1 (en)	2011-12-07	2013-06-13	Dsm Ip Assets B.V.	Process for the production of a mixture comprising cyclohexanol and cyclohexanone
CN107108424A (zh)	2014-10-31	2017-08-29	宇部兴产株式会社	一种酮和/或醇的制造方法及其系统
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 (3)

* 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
NL7506790A (nl) *	1975-06-07	1976-12-09	Stamicarbon	Werkwijze voor het bereiden van cycloalkanonen en cycloalkanolen.
NL7802125A (nl) *	1978-02-25	1979-08-28	Stamicarbon	Werkwijze voor het bereiden van cycloalkanolen en cycloalkanonen.

1982
- 1982-04-23 NL NL8201695A patent/NL8201695A/nl not_active Application Discontinuation
1983
- 1983-04-15 EP EP83200544A patent/EP0092867B1/de not_active Expired
- 1983-04-15 DE DE8383200544T patent/DE3364495D1/de not_active Expired
- 1983-04-22 PT PT76592A patent/PT76592B/pt unknown
- 1983-04-22 JP JP58071321A patent/JPH0615484B2/ja not_active Expired - Lifetime
- 1983-04-22 KR KR1019830001703A patent/KR870000056B1/ko not_active Expired
- 1983-04-22 ES ES521744A patent/ES8402249A1/es not_active Expired
- 1983-04-22 CA CA000426474A patent/CA1244475A/en not_active Expired
- 1983-04-22 BR BR8302088A patent/BR8302088A/pt not_active IP Right Cessation

Also Published As

Publication number	Publication date
PT76592B (en)	1985-12-10
EP0092867B1 (de)	1986-07-16
KR870000056B1 (ko)	1987-02-09
ES521744A0 (es)	1984-01-16
PT76592A (en)	1983-05-01
EP0092867A1 (de)	1983-11-02
KR840004707A (ko)	1984-10-24
JPH0615484B2 (ja)	1994-03-02
JPS58192839A (ja)	1983-11-10
DE3364495D1 (en)	1986-08-21
BR8302088A (pt)	1983-12-27
CA1244475A (en)	1988-11-08
ES8402249A1 (es)	1984-01-16

Publication	Publication Date	Title
NL8201695A (nl)	1983-11-16	Werkwijze voor de bereiding van cyclohexanol en cyclohexanon.
US3957876A (en)	1976-05-18	Process for the oxidation of cyclohexane
EP0004105B1 (de)	1981-08-12	Verfahren zur Herstellung von Cycloalkanolen und Cycloalkanonen
BE1007904A3 (nl)	1995-11-14	Werkwijze voor de bereiding van een alkanol en/of een alkanon.
EP1562885A1 (de)	2005-08-17	Kontinuierliches verfahren zur herstellung von pseudojononen und jononen
RU2308445C2 (ru)	2007-10-20	Способ разложения циклогексилгидропероксида с высоким выходом циклогексанола и циклогексанона
EP0634993B1 (de)	1997-09-17	Verfahren mit hohem nutzeffekt zur herstellung von cyclohexanol und cyclohexanon
US5905173A (en)	1999-05-18	Process for decomposing cycloalkyl hydroperoxide
MX2007008983A (es)	2007-09-21	Procedimiento para preparar ciclohexanona y ciclohexanol.
JP3426213B2 (ja)	2003-07-14	シクロヘキサノールおよびシクロヘキサノンを製造する改良された方法
JP5774027B2 (ja)	2015-09-02	アルキルヒドロペルオキシドの製造方法
JP2500977B2 (ja)	1996-05-29	シクロヘキサノンの製造方法
US3941845A (en)	1976-03-02	Process for preparing cycloalkanones and cycloalkanols
JP2515311B2 (ja)	1996-07-10	シクロヘキシルヒドロペルオキシド、シクロヘキサノ−ル及びシクロヘキサノンを含有する反応混合物を後処理する方法
US3658898A (en)	1972-04-25	Process for producing adipic acid
RU2661867C2 (ru)	2018-07-20	Непрерывный способ получения очищенного циклогексанона
JPH05301858A (ja)	1993-11-16	カプロラクタムの製法
BE1011041A3 (nl)	1999-04-06	Werkwijze voor het ontleden van cycloalkylhydroperoxide.
PL187890B1 (pl)	2004-10-29	Sposób otrzymywania 1,2,3-cykloheksanotriolu
JPH0532575A (ja)	1993-02-09	ヒドロキノンの製造方法

Legal Events

Date	Code	Title
1983-11-16	A1B	A search report has been drawn up
1985-01-01	A85	Still pending on 85-01-01
1985-12-02	BV	The patent application has lapsed