CS224636B2 - Method for producing cyclohexanol and/or cyclohexanon from cyclohexan - Google Patents

Method for producing cyclohexanol and/or cyclohexanon from cyclohexan Download PDF

Info

Publication number: CS224636B2
Authority: CS; Czechoslovakia
Prior art keywords: cyclohexane; cyclohexene; cyclohexanone; range; temperature
Prior art date: 1980-12-04

Application number

CS818960A

Other languages

Czech (cs)

English (en)

Inventor

Christiaan Boelens

Geem Christiaan Van

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

1984-01-16

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

1984-01-16 Publication of CS224636B2 publication Critical patent/CS224636B2/cs

Links

JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title claims abstract description 57
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title claims abstract description 41
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 title claims abstract description 17
238000004519 manufacturing process Methods 0.000 title claims description 5
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims abstract description 69
238000000034 method Methods 0.000 claims abstract description 29
238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 12
238000002360 preparation method Methods 0.000 claims abstract description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 60
239000000203 mixture Substances 0.000 claims description 16
238000005984 hydrogenation reaction Methods 0.000 claims description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 6
230000036571 hydration Effects 0.000 claims description 6
238000006703 hydration reaction Methods 0.000 claims description 6
238000009835 boiling Methods 0.000 claims description 5
238000000926 separation method Methods 0.000 claims description 5
230000001590 oxidative effect Effects 0.000 claims description 2
239000013067 intermediate product Substances 0.000 claims 1
239000003054 catalyst Substances 0.000 description 21
238000007254 oxidation reaction Methods 0.000 description 14
230000003647 oxidation Effects 0.000 description 13
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 11
239000012071 phase Substances 0.000 description 9
230000000052 comparative effect Effects 0.000 description 7
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
238000004821 distillation Methods 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 4
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
239000007789 gas Substances 0.000 description 4
238000002955 isolation Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
239000010452 phosphate Substances 0.000 description 3
229910052697 platinum Inorganic materials 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
150000001935 cyclohexenes Chemical class 0.000 description 2
150000005690 diesters Chemical class 0.000 description 2
SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000011790 ferrous sulphate Substances 0.000 description 2
235000003891 ferrous sulphate Nutrition 0.000 description 2
-1 for example Chemical compound 0.000 description 2
FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 2
KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
229910021592 Copper(II) chloride Inorganic materials 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
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229940115440 aluminum sodium silicate Drugs 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
229960003280 cupric chloride Drugs 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
QDYKZBKCLHBUHU-UHFFFAOYSA-N cyclohexyl(phenyl)methanol Chemical compound C=1C=CC=CC=1C(O)C1CCCCC1 QDYKZBKCLHBUHU-UHFFFAOYSA-N 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
229910052675 erionite Inorganic materials 0.000 description 1
239000008246 gaseous mixture Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000007791 liquid phase Substances 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
PCLURTMBFDTLSK-UHFFFAOYSA-N nickel platinum Chemical compound [Ni].[Pt] PCLURTMBFDTLSK-UHFFFAOYSA-N 0.000 description 1
238000005839 oxidative dehydrogenation reaction Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
229920005990 polystyrene resin Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
235000012217 sodium aluminium silicate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 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)

CS818960A 1980-12-04 1981-12-03 Method for producing cyclohexanol and/or cyclohexanon from cyclohexan CS224636B2 (en)

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
CS224636B2 true CS224636B2 (en)	1984-01-16

Family

ID=19836280

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS818960A CS224636B2 (en)	1980-12-04	1981-12-03	Method for producing cyclohexanol and/or cyclohexanon from cyclohexan

Country Status (10)

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

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 (es) *	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
DD202526A5 (de)	1983-09-21
BR8107857A (pt)	1982-09-08
YU280181A (en)	1983-02-28
PL234078A1 (es)	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

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