DD202526A5 - Verfahren zur herstellung von cyclohexanol und/oder cyclohexanon - Google Patents

Verfahren zur herstellung von cyclohexanol und/oder cyclohexanon Download PDF

Info

Publication number: DD202526A5
Authority: DD; German Democratic Republic
Prior art keywords: cyclohexane; cyclohexanol; cyclohexene; cyclohexanone; mpa
Prior art date: 1980-12-04

Application number

DD81235376A

Other languages

German (de)

English (en)

Inventor

Christiaan Boelens

Paul C Van Geem

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.)

1980-12-04

Filing date

1981-12-03

Publication date

1983-09-21

1981-12-03 Application filed by Stamicarbon filed Critical Stamicarbon

1983-09-21 Publication of DD202526A5 publication Critical patent/DD202526A5/de

Links

JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title claims abstract description 66
238000000034 method Methods 0.000 title claims abstract description 34
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 title claims abstract description 31
238000002360 preparation method Methods 0.000 title claims description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 56
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims abstract description 41
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 36
239000000203 mixture Substances 0.000 claims abstract description 18
238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 15
238000005984 hydrogenation reaction Methods 0.000 claims abstract description 14
239000003054 catalyst Substances 0.000 claims description 18
230000036571 hydration Effects 0.000 claims description 9
238000006703 hydration reaction Methods 0.000 claims description 9
239000011541 reaction mixture Substances 0.000 claims description 9
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
239000012071 phase Substances 0.000 claims description 4
229910052697 platinum Inorganic materials 0.000 claims description 4
150000001934 cyclohexanes Chemical class 0.000 claims description 3
239000007791 liquid phase Substances 0.000 claims description 2
HPXRVTGHNJAIIH-PTQBSOBMSA-N cyclohexanol Chemical group O[13CH]1CCCCC1 HPXRVTGHNJAIIH-PTQBSOBMSA-N 0.000 claims 1
LYJAIAHSQKJJAL-UHFFFAOYSA-N cyclohexanol;hydrate Chemical compound O.OC1CCCCC1 LYJAIAHSQKJJAL-UHFFFAOYSA-N 0.000 claims 1
230000008021 deposition Effects 0.000 claims 1
239000002244 precipitate Substances 0.000 claims 1
LLVUBGQEALYPBE-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1.C1CCC=CC1 LLVUBGQEALYPBE-UHFFFAOYSA-N 0.000 description 26
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
238000004821 distillation Methods 0.000 description 13
230000003647 oxidation Effects 0.000 description 13
238000007254 oxidation reaction Methods 0.000 description 13
239000012074 organic phase Substances 0.000 description 7
239000007789 gas Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
239000006227 byproduct Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
101150003085 Pdcl gene Proteins 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000004793 Polystyrene Substances 0.000 description 2
238000009825 accumulation Methods 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
150000001935 cyclohexenes Chemical class 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
238000010931 ester hydrolysis Methods 0.000 description 2
238000000895 extractive distillation Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 2
229910000359 iron(II) sulfate Inorganic materials 0.000 description 2
239000010410 layer Substances 0.000 description 2
GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
238000010405 reoxidation reaction Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
XFAHEGIMRQOLMW-UHFFFAOYSA-N C1CCCCC1.C1CCC=CC1.C1=CC=CC=C1 Chemical compound C1CCCCC1.C1CCC=CC1.C1=CC=CC=C1 XFAHEGIMRQOLMW-UHFFFAOYSA-N 0.000 description 1
101100129922 Caenorhabditis elegans pig-1 gene Proteins 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
101100520057 Drosophila melanogaster Pig1 gene Proteins 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
229910000990 Ni alloy Inorganic materials 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
VTEMZXZTDRBGGY-UHFFFAOYSA-N [O].C1CCCCC1 Chemical compound [O].C1CCCCC1 VTEMZXZTDRBGGY-UHFFFAOYSA-N 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 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
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000003426 co-catalyst Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
VYWLNKBAMVZVAJ-UHFFFAOYSA-N cyclohexane cyclohexene Chemical compound C1=CCCCC1.C1CCCCC1 VYWLNKBAMVZVAJ-UHFFFAOYSA-N 0.000 description 1
-1 cyclohexanol ester Chemical class 0.000 description 1
GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 1
UCZUCGRGTXIWLR-UHFFFAOYSA-N cyclohexyl hydrogen sulfate Chemical compound OS(=O)(=O)OC1CCCCC1 UCZUCGRGTXIWLR-UHFFFAOYSA-N 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
229910052675 erionite Inorganic materials 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000008246 gaseous mixture Substances 0.000 description 1
FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
238000005839 oxidative dehydrogenation reaction Methods 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
229920005990 polystyrene resin Polymers 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 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
- C07C45/34—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 in unsaturated compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- 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
- C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
- C07C29/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds
- 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
- C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
- C07C29/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds
- C07C29/05—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds with formation of absorption products in mineral acids and their hydrolysis
- C07C29/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds with formation of absorption products in mineral acids and their hydrolysis the acid being sulfuric acid
- 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
- C07C45/37—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 >C—O—functional groups to >C=O groups
- C07C45/39—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 >C—O—functional groups to >C=O groups being a secondary hydroxyl group
- 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)
Life Sciences & Earth Sciences (AREA)
Environmental & Geological Engineering (AREA)
General Life Sciences & Earth Sciences (AREA)
Geochemistry & Mineralogy (AREA)
Geology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD81235376A 1980-12-04 1981-12-03 Verfahren zur herstellung von cyclohexanol und/oder cyclohexanon DD202526A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
NL8006602A NL8006602A (nl)	1980-12-04	1980-12-04	Werkwijze voor het bereiden van cyclohexanol en/of cyclohexanon.

Publications (1)

Publication Number	Publication Date
DD202526A5 true DD202526A5 (de)	1983-09-21

Family

ID=19836280

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD81235376A DD202526A5 (de)	1980-12-04	1981-12-03	Verfahren zur herstellung von cyclohexanol und/oder cyclohexanon

Country Status (10)

Country	Link
EP (1)	EP0053847A1 (cs)
JP (1)	JPS57120538A (cs)
KR (1)	KR830007481A (cs)
BR (1)	BR8107857A (cs)
CS (1)	CS224636B2 (cs)
DD (1)	DD202526A5 (cs)
ES (1)	ES8207111A1 (cs)
NL (1)	NL8006602A (cs)
PL (1)	PL234078A1 (cs)
YU (1)	YU280181A (cs)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5233095A (en) *	1986-03-18	1993-08-03	Catalytica, Inc.	Process for manufacture of resorcinol
NL8801036A (nl) *	1988-04-21	1989-11-16	Stamicarbon	Werkwijze voor de bereiding van cyclohexanol en/of cyclohexanon.
CN115838325A (zh) *	2021-09-18	2023-03-24	中国石油化工股份有限公司	一种环己烯与环己烷耦合制环己酮的方法
CN115838324B (zh) *	2021-09-18	2024-05-28	中国石油化工股份有限公司	一种水合与氧化联合脱氢制环己酮的方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1087595B (de) *	1959-01-15	1960-08-25	Ruhrchemie Ag	Kreislaufverfahren zur Herstellung von Cyclohexanon
LU40055A1 (cs) *	1960-04-26	1961-06-24
DE2437472A1 (de) *	1974-08-03	1976-04-22	Bayer Antwerpen Nv	Verfahren zur oxidation von kohlenwasserstoffen
JPS51118743A (en) *	1975-04-08	1976-10-18	Ube Ind Ltd	Process for preparation of cyclohexene from high boiling point mixed o il
JPS5390242A (en) *	1977-01-18	1978-08-08	Toray Ind Inc	Preparation of cyclohexanol
NL7804667A (nl) *	1978-04-29	1979-10-31	Stamicarbon	Werkwijze voor het bereiden van cyclohexanon.
FR2442835A1 (fr) *	1978-11-30	1980-06-27	Inst Francais Du Petrole	Nouveaux complexes peroxydiques du platine et du palladium, leur procede de fabrication et leur utilisation comme reactifs selectifs d'oxydation et de deshydrogenation oxydante
NL7905781A (nl) *	1979-07-26	1981-01-28	Stamicarbon	Werkwijze voor het bereiden van cyclohexanol.

1980
- 1980-12-04 NL NL8006602A patent/NL8006602A/nl not_active Application Discontinuation
1981
- 1981-10-30 EP EP81201219A patent/EP0053847A1/en not_active Withdrawn
- 1981-11-30 KR KR1019810004702A patent/KR830007481A/ko not_active Withdrawn
- 1981-12-02 YU YU02801/81A patent/YU280181A/xx unknown
- 1981-12-03 ES ES507669A patent/ES8207111A1/es not_active Expired
- 1981-12-03 CS CS818960A patent/CS224636B2/cs unknown
- 1981-12-03 BR BR8107857A patent/BR8107857A/pt unknown
- 1981-12-03 PL PL23407881A patent/PL234078A1/xx unknown
- 1981-12-03 JP JP56193760A patent/JPS57120538A/ja active Pending
- 1981-12-03 DD DD81235376A patent/DD202526A5/de unknown

Also Published As

Publication number	Publication date
EP0053847A1 (en)	1982-06-16
BR8107857A (pt)	1982-09-08
YU280181A (en)	1983-02-28
CS224636B2 (en)	1984-01-16
PL234078A1 (cs)	1982-07-05
JPS57120538A (en)	1982-07-27
NL8006602A (nl)	1982-07-01
ES507669A0 (es)	1982-09-01
ES8207111A1 (es)	1982-09-01
KR830007481A (ko)	1983-10-21

Publication	Publication Date	Title
DE2250088C2 (de)	1984-02-16	Kontinuierliches Verfahren zur Abtrennung von Cyclohexanon aus dem bei der Dehydrierung von Cyclohexanol anfallenden wasserhaltigen Umsetzungsprodukt
DD147664A5 (de)	1981-04-15	Verfahren zur gleichzeitigen herstellung von reinem methyl-tert.-butylether
EP1066241A2 (de)	2001-01-10	Verfahren zur herstellung von (meth)acrylsäure und (meth)acrylsäureestern
DE19709392A1 (de)	1998-09-10	Verfahren zur Extraktion von (Meth)acrylsäure
DD152534A5 (de)	1981-12-02	Verfahren zur herstellung von cyclohexanol und/oder cyclohexanone
DE2921503C2 (cs)	1990-04-19
DE69902683T2 (de)	2003-07-31	Verfahren zur herstellung von gamma-butyrolacton und tetrahydrofuran
DE19709471A1 (de)	1998-09-10	Verfahren zur Herstellung von (Meth)acrylsäure
DD202526A5 (de)	1983-09-21	Verfahren zur herstellung von cyclohexanol und/oder cyclohexanon
EP0204917B1 (de)	1991-01-16	Verfahren zur Aufarbeitung von Cyclohexanol, Cyclohexanon sowie Cyclohexylhydroperoxid enthaltenden Reaktionsgemischen
DE4428462A1 (de)	1996-02-15	Verfahren zur Herstellung von Dinitrotoluol
DE19856205A1 (de)	1999-06-10	Verfahren zur Herstellung eines hochreinen Caprolactams
EP0055354B1 (de)	1984-09-12	Verfahren zur kontinuierlichen Herstellung von 3-Alkyl-buten-1-alen
EP0268826B1 (de)	1990-02-28	Verfahren zur Aufbereitung von Cyclohexylhydroperoxid enthaltenden Reaktionsgemischen
DE4413176A1 (de)	1994-10-20	Verfahren zur Herstellung von Cyclohexyladipaten und Adipinsäure
DD218092A1 (de)	1985-01-30	Verfahren zur herstellung von cyclohexanon und cyclohexanol
DE69017864T2 (de)	1995-11-23	Verfahren zur Herstellung von Phenol.
EP0150290B1 (de)	1987-04-01	Verfahren zur Herstellung von 13-Oxabicyclo [10.3.0]-pentadecan
DE3500678A1 (de)	1986-07-17	Verfahren zur gewinnung wasserfreier methacrylsaeure
EP1188737A1 (de)	2002-03-20	Verfahren zur Aufarbeitung von Mesityloxid aufweisenden Stoffströmen
DE951867C (de)	1956-11-08	Verfahren zur Herstellung von Norcampher (2-Ketobicyclo-[2,2,1]-heptan) aus Cyclopentadien und AEthylen
DE2516316B2 (de)	1978-03-30	Verfahren zur Herstellung von o-Äthylanilin durch Dampfphasenaminierung
EP0064180B1 (de)	1984-06-27	Verfahren zur Herstellung von 2,3-Dimethylbutan-2,3-diol
AT206880B (de)	1959-12-28	Verfahren zur Herstellung von Maleinsäureanhydrid
DE1518970C3 (de)	1976-09-02	Verfahren zur Herstellung von gesättigten aliphatischen Dicarbonsäuren