CN1051763C - 环己基氢过氧化物的制备方法 - Google Patents

环己基氢过氧化物的制备方法 Download PDF

Info

Publication number: CN1051763C
Authority: CN; China
Prior art keywords: oxidation; hexanaphthene; cyclohexyl hydroperoxide; reactor; pimelinketone
Prior art date: 1992-07-15
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

CN93116485A

Other languages

English (en)

Chinese (zh)

Other versions

CN1087627A (zh

Inventor

C·G·M·范迪默斯迪克

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

D Sm I P Property Co Ltd

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.)

1992-07-15

Filing date

1993-07-14

Publication date

2000-04-26

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=19861062&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CN1051763(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1993-07-14 Application filed by DSM NV filed Critical DSM NV

1994-06-08 Publication of CN1087627A publication Critical patent/CN1087627A/zh

2000-04-26 Application granted granted Critical

2000-04-26 Publication of CN1051763C publication Critical patent/CN1051763C/zh

2013-07-14 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 title claims abstract description 54
238000000034 method Methods 0.000 title claims abstract description 35
230000008569 process Effects 0.000 title claims abstract description 15
238000002360 preparation method Methods 0.000 title claims abstract description 5
238000007254 oxidation reaction Methods 0.000 claims abstract description 92
239000000203 mixture Substances 0.000 claims abstract description 79
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 72
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims abstract description 42
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims abstract description 36
238000006243 chemical reaction Methods 0.000 claims abstract description 31
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 17
239000001301 oxygen Substances 0.000 claims abstract description 17
229910052760 oxygen Inorganic materials 0.000 claims abstract description 17
239000007789 gas Substances 0.000 claims abstract description 8
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
125000006165 cyclic alkyl group Chemical group 0.000 claims abstract description 4
230000003647 oxidation Effects 0.000 claims description 89
230000001590 oxidative effect Effects 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 11
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 claims description 5
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 4
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 4
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 3
XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 claims description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
FPFTWHJPEMPAGE-UHFFFAOYSA-N 6-hydroxy caproaldehyde Chemical compound OCCCCCC=O FPFTWHJPEMPAGE-UHFFFAOYSA-N 0.000 claims description 2
UALYCKSVHDYQRP-UHFFFAOYSA-N 6-hydroxyhexan-2-one Chemical compound CC(=O)CCCCO UALYCKSVHDYQRP-UHFFFAOYSA-N 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical class CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 2
235000019253 formic acid Nutrition 0.000 claims description 2
239000012451 post-reaction mixture Substances 0.000 claims 1
239000003054 catalyst Substances 0.000 abstract description 4
239000000047 product Substances 0.000 description 27
239000002253 acid Substances 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 12
150000001721 carbon Chemical group 0.000 description 8
-1 cycloalkyl hydroperoxide Chemical compound 0.000 description 8
JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 8
239000007788 liquid Substances 0.000 description 8
238000000354 decomposition reaction Methods 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
230000008901 benefit Effects 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 5
230000004044 response Effects 0.000 description 5
150000001336 alkenes Chemical class 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000006227 byproduct Substances 0.000 description 3
229910052804 chromium Chemical class 0.000 description 3
239000011651 chromium Chemical class 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 class [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
238000007599 discharging Methods 0.000 description 3
238000004821 distillation Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
150000003509 tertiary alcohols Chemical class 0.000 description 3
239000002912 waste gas Substances 0.000 description 3
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical class [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
238000004880 explosion Methods 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000008246 gaseous mixture Substances 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
229910052723 transition metal Inorganic materials 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 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
229910000831 Steel Inorganic materials 0.000 description 1
OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000005189 alkyl hydroxy group Chemical group 0.000 description 1
239000004411 aluminium Substances 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
238000005422 blasting Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000010960 commercial process Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
210000003298 dental enamel Anatomy 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000003999 initiator Substances 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012856 packing Methods 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
238000003672 processing method Methods 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000010959 steel Substances 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
238000012360 testing method Methods 0.000 description 1
229910021654 trace metal Inorganic materials 0.000 description 1
230000009466 transformation Effects 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1

Classifications

- 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
- 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Steroid Compounds (AREA)
Hydrogenated Pyridines (AREA)
Epoxy Compounds (AREA)

CN93116485A 1992-07-15 1993-07-14 环己基氢过氧化物的制备方法 Expired - Lifetime CN1051763C (zh)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL9201269		1992-07-15
NL9201269A NL9201269A (nl)	1992-07-15	1992-07-15	Werkwijze voor de bereiding van cyclohexylhydroperoxide.

Publications (2)

Publication Number	Publication Date
CN1087627A CN1087627A (zh)	1994-06-08
CN1051763C true CN1051763C (zh)	2000-04-26

Family

ID=19861062

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN93116485A Expired - Lifetime CN1051763C (zh)	1992-07-15	1993-07-14	环己基氢过氧化物的制备方法

Country Status (20)

Country	Link
EP (1)	EP0579323B1 (2)
JP (1)	JP3599758B2 (2)
KR (1)	KR100278129B1 (2)
CN (1)	CN1051763C (2)
AT (1)	ATE143358T1 (2)
BR (1)	BR9302860A (2)
CZ (1)	CZ288373B6 (2)
DE (1)	DE69305015T2 (2)
ES (1)	ES2093914T3 (2)
GE (1)	GEP19971110B (2)
HU (1)	HU218302B (2)
MX (1)	MX9304248A (2)
MY (1)	MY108925A (2)
NL (1)	NL9201269A (2)
PL (1)	PL178142B1 (2)
RU (1)	RU2121996C1 (2)
SG (1)	SG49325A1 (2)
SK (1)	SK281678B6 (2)
TW (1)	TW321635B (2)
UA (1)	UA44214C2 (2)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU4658199A (en) *	1998-06-26	2000-01-17	Dsm N.V.	Diesel mixture containing cycloalkylhydroperoxide
JP4601805B2 (ja) *	2000-11-24	2010-12-22	ダイセル化学工業株式会社	シクロヘキサンの酸化方法
US7091365B2 (en)	2004-03-08	2006-08-15	Abb Lummus Global Inc.	Process for olefin epoxidation and co-production of nylon precursor
EP1805125A1 (en) *	2004-10-27	2007-07-11	DSMIP Assets B.V.	Process for the preparation of cyclohexanol and cyclohexanone
FR2878847B1 (fr) *	2004-12-07	2007-01-05	Rhodia Chimie Sa	Procede de preparation de cyclohexanone
EP1828090B1 (en) *	2004-12-22	2010-10-27	DSM IP Assets B.V.	Process for decomposing cyclohexylhdroperoxide
JP5160048B2 (ja) *	2006-05-15	2013-03-13	旭化成ケミカルズ株式会社	アリルアルコール類の製造方法
CN101417968B (zh) *	2007-10-26	2013-09-11	环球油品公司	一种氢过氧化物的制备方法
FR2954314B1 (fr) *	2009-12-17	2012-01-27	Rhodia Operations	Procede d'oxydation d'hydrocarbures par l'oxygene
EA025632B1 (ru) *	2011-12-07	2017-01-30	Кап Iii Б.В.	Способ получения смеси, содержащей циклогексанол и циклогексанон
WO2013083512A1 (en)	2011-12-07	2013-06-13	Dsm Ip Assets B.V.	Process for the production of a mixture comprising cyclohexanol and cyclohexanone
RU2673541C1 (ru) *	2017-10-13	2018-11-28	Открытое акционерное общество "Щекиноазот"	Способ получения циклогексанона, циклогексанола и циклогексилгидропероксида, установка для его осуществления и устройство абсорбции реакционных газов и предварительного окисления циклогексана
RU2747484C1 (ru) *	2020-10-27	2021-05-05	Публичное акционерное общество "КуйбышевАзот"	Способ получения гидропероксида циклогексила

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH467230A (de) *	1964-03-03	1969-01-15	Wallace & Tiernan Inc	Verfahren zur Herstellung von Alkandicarbonsäuren aus Cycloalkanen
FR1506296A (fr) *	1966-03-11	1967-12-22	Charbonnages De France	Procédé d'oxydation en continu de composés organiques
NL7802125A (nl) *	1978-02-25	1979-08-28	Stamicarbon	Werkwijze voor het bereiden van cycloalkanolen en cycloalkanonen.
US5043481A (en) *	1990-09-28	1991-08-27	Arco Chemical Technology, Inc.	Cyclohexane oxidation

1992
- 1992-07-15 NL NL9201269A patent/NL9201269A/nl not_active Application Discontinuation
1993
- 1993-07-06 TW TW082105378A patent/TW321635B/zh not_active IP Right Cessation
- 1993-07-08 UA UA93002267A patent/UA44214C2/uk unknown
- 1993-07-09 SG SG1996009377A patent/SG49325A1/en unknown
- 1993-07-09 EP EP93202018A patent/EP0579323B1/en not_active Expired - Lifetime
- 1993-07-09 DE DE69305015T patent/DE69305015T2/de not_active Expired - Lifetime
- 1993-07-09 ES ES93202018T patent/ES2093914T3/es not_active Expired - Lifetime
- 1993-07-09 AT AT93202018T patent/ATE143358T1/de not_active IP Right Cessation
- 1993-07-14 SK SK743-93A patent/SK281678B6/sk not_active IP Right Cessation
- 1993-07-14 JP JP17425193A patent/JP3599758B2/ja not_active Expired - Lifetime
- 1993-07-14 RU RU93049735A patent/RU2121996C1/ru active
- 1993-07-14 PL PL93299671A patent/PL178142B1/pl unknown
- 1993-07-14 CN CN93116485A patent/CN1051763C/zh not_active Expired - Lifetime
- 1993-07-14 HU HU9302021A patent/HU218302B/hu not_active IP Right Cessation
- 1993-07-14 BR BR9302860A patent/BR9302860A/pt not_active IP Right Cessation
- 1993-07-14 MX MX9304248A patent/MX9304248A/es unknown
- 1993-07-14 MY MYPI93001374A patent/MY108925A/en unknown
- 1993-07-15 KR KR1019930013550A patent/KR100278129B1/ko not_active Expired - Lifetime
- 1993-07-15 CZ CZ19931414A patent/CZ288373B6/cs not_active IP Right Cessation
- 1993-07-15 GE GEAP19931034A patent/GEP19971110B/en unknown

Also Published As

Publication number	Publication date
SK281678B6 (sk)	2001-06-11
CN1087627A (zh)	1994-06-08
DE69305015T2 (de)	1997-04-10
ATE143358T1 (de)	1996-10-15
CZ141493A3 (en)	1994-02-16
UA44214C2 (uk)	2002-02-15
TW321635B (2)	1997-12-01
MX9304248A (es)	1994-02-28
SK74393A3 (en)	1994-06-08
ES2093914T3 (es)	1997-01-01
KR100278129B1 (ko)	2001-02-01
PL299671A1 (en)	1994-02-21
GEP19971110B (en)	1997-10-10
PL178142B1 (pl)	2000-03-31
DE69305015D1 (de)	1996-10-31
MY108925A (en)	1996-11-30
SG49325A1 (en)	1998-05-18
HU9302021D0 (en)	1993-11-29
CZ288373B6 (en)	2001-06-13
RU2121996C1 (ru)	1998-11-20
HU218302B (en)	2000-07-28
KR940005537A (ko)	1994-03-21
NL9201269A (nl)	1994-02-01
EP0579323A1 (en)	1994-01-19
BR9302860A (pt)	1994-03-01
JPH06157456A (ja)	1994-06-03
EP0579323B1 (en)	1996-09-25
JP3599758B2 (ja)	2004-12-08
HUT64515A (en)	1994-01-28

Legal Events

Date	Code	Title	Description
1994-06-01	C10	Entry into substantive examination
1994-06-01	SE01	Entry into force of request for substantive examination
1994-06-08	C06	Publication
1994-06-08	PB01	Publication
2000-04-26	C14	Grant of patent or utility model
2000-04-26	GR01	Patent grant
2004-07-21	ASS	Succession or assignment of patent right	Owner name: DSM IP PROPERTY CO., LTD. Free format text: FORMER OWNER: DSM N. V. Effective date: 20040618
2004-07-21	C41	Transfer of patent application or patent right or utility model
2004-07-21	TR01	Transfer of patent right	Effective date of registration: 20040618 Address after: Holland Heerlen Patentee after: D Sm I P Property Company Limited Address before: Holland Heerlen Patentee before: DSM N. V.
2013-08-21	C17	Cessation of patent right
2013-08-21	CX01	Expiry of patent term	Expiration termination date: 20130714 Granted publication date: 20000426

Publication	Publication Date	Title
CN1051763C (zh)	2000-04-26	环己基氢过氧化物的制备方法
EP1539665B1 (en)	2011-11-09	Process for oxidation of cyclohexane
US6008415A (en)	1999-12-28	Cyclohexane oxidation
EP2036880B1 (de)	2014-01-22	Verfahren zur Herstellung von Diaryl- oder Alkylarylcarbonaten aus Dialkylcarbonaten
CN1082040C (zh)	2002-04-03	苯酚的制备方法
KR20100099304A (ko)	2010-09-10	다중 후-증류에 의한 사이클로헥사논의 제조방법
DE19755026A1 (de)	1998-06-18	Verbessertes Verfahren zur Herstellung von Phenol und Aceton aus Cumol
CN87105587A (zh)	1988-03-30	邻苯二甲酸酐的生产方法
US3946077A (en)	1976-03-23	Process for oxidating hydrocarbons
CN1156714A (zh)	1997-08-13	分解环烷基氢过氧化物的方法
CN1189456C (zh)	2005-02-16	高纯度己内酰胺的制备方法
CN1314877A (zh)	2001-09-26	生产脂族二酸和氧化亚氮的方法
CN115304471B (zh)	2025-02-14	一种长碳链二元羧酸的制备方法
CN115160127B (zh)	2024-06-11	一种共氧化反应制备长碳链二元酸的方法
WO1994002458A1 (en)	1994-02-03	Initiated peroxidation of secondary carbon in alkanes and cycloalkanes
BE1006451A3 (nl)	1994-08-30	Werkwijze voor de continue bereiding van een mengsel van een cycloalkanon, cycloalkanol en een cycloalkylhydroperoxide.
DE69609940T4 (de)	2002-05-29	Verfahren zur Herstellung von Adipinsäure
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US3770829A (en)	1973-11-06	Dihydroisophorone purification process
US3665028A (en)	1972-05-23	Process for preparation of borate esters
DE2358422A1 (de)	1974-05-30	Verfahren zur herstellung von cyclohexanon
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RAYMOND	1977	Adipic Acid [HOOC (CH2) 4COOH]
DD236233A3 (de)	1986-06-04	Verfahren zur herstellung von reinem aceton