CA1070328A - Procede pour la preparation de cycloalcanones et de cycloalcanols - Google Patents

Procede pour la preparation de cycloalcanones et de cycloalcanols

Info

Publication number: CA1070328A
Authority: CA; Canada
Prior art keywords: conversion; catalyst; reaction mixture; cycloalkanones; temperature
Prior art date: 1975-06-07
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

Application number

CA253,976A

Other languages

English (en)

Inventor

Jan Wolters

Jan L. J. P. Hennekens

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.)

Stamicarbon BV

Original Assignee

Stamicarbon BV

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.)

1975-06-07

Filing date

1976-06-03

Publication date

1980-01-22

1976-06-03 Application filed by Stamicarbon BV filed Critical Stamicarbon BV

1980-01-22 Application granted granted Critical

1980-01-22 Publication of CA1070328A publication Critical patent/CA1070328A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title description 2
238000006243 chemical reaction Methods 0.000 claims abstract description 36
239000003054 catalyst Substances 0.000 claims abstract description 29
239000011541 reaction mixture Substances 0.000 claims abstract description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims abstract description 7
229910000423 chromium oxide Inorganic materials 0.000 claims abstract description 7
238000004519 manufacturing process Methods 0.000 claims abstract description 5
239000007787 solid Substances 0.000 claims abstract description 4
239000007788 liquid Substances 0.000 claims description 6
239000004215 Carbon black (E152) Substances 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
150000002430 hydrocarbons Chemical class 0.000 claims description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 8
-1 cycloalkyl hydroperoxides Chemical class 0.000 description 11
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000007789 gas Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
150000001924 cycloalkanes Chemical class 0.000 description 6
238000007254 oxidation reaction Methods 0.000 description 6
150000002978 peroxides Chemical group 0.000 description 6
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 5
QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
239000011651 chromium Substances 0.000 description 4
FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 4
239000007791 liquid phase Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical group C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229910052804 chromium Inorganic materials 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
150000001845 chromium compounds Chemical class 0.000 description 2
VQWFNAGFNGABOH-UHFFFAOYSA-K chromium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[Cr+3] VQWFNAGFNGABOH-UHFFFAOYSA-K 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
229910001882 dioxygen Inorganic materials 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
229910002012 Aerosil® Inorganic materials 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000011149 active material Substances 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
239000008346 aqueous phase Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 description 1
JOPOVCBBYLSVDA-UHFFFAOYSA-N chromium(6+) Chemical compound [Cr+6] JOPOVCBBYLSVDA-UHFFFAOYSA-N 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
239000012045 crude solution Substances 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
239000000203 mixture Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
229910001887 tin oxide Inorganic materials 0.000 description 1
239000004408 titanium dioxide Substances 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
- C07C45/51—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

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)

CA253,976A 1975-06-07 1976-06-03 Procede pour la preparation de cycloalcanones et de cycloalcanols Expired CA1070328A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
NL7506790A NL7506790A (nl)	1975-06-07	1975-06-07	Werkwijze voor het bereiden van cycloalkanonen en cycloalkanolen.

Publications (1)

Publication Number	Publication Date
CA1070328A true CA1070328A (fr)	1980-01-22

Family

ID=19823915

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA253,976A Expired CA1070328A (fr)	1975-06-07	1976-06-03	Procede pour la preparation de cycloalcanones et de cycloalcanols

Country Status (15)

Country	Link
JP (1)	JPS6033809B2 (fr)
AR (1)	AR206572A1 (fr)
BE (1)	BE842635R (fr)
BR (1)	BR7603568A (fr)
CA (1)	CA1070328A (fr)
CH (1)	CH608774A5 (fr)
DD (1)	DD124971A6 (fr)
DE (1)	DE2625273A1 (fr)
ES (1)	ES448576A2 (fr)
FR (1)	FR2313336A2 (fr)
GB (1)	GB1535869A (fr)
IT (1)	IT1061404B (fr)
MX (1)	MX144251A (fr)
NL (1)	NL7506790A (fr)
PL (1)	PL101224B3 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1590958A (en) *	1976-12-31	1981-06-10	Ici Ltd	Oxidation of cyclohexane
NL8201695A (nl) *	1982-04-23	1983-11-16	Stamicarbon	Werkwijze voor de bereiding van cyclohexanol en cyclohexanon.
RU2154050C1 (ru) *	1999-01-19	2000-08-10	Ярославский государственный технический университет	Способ получения циклоалканонов c8-c12
CN104741377B (zh)	2015-03-30	2017-01-04	宝山钢铁股份有限公司	具有纵向不同厚度的板材的轧制方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT327166B (de) *	1972-10-21	1976-01-26	Stamicarbon	Verfahren zur herstellung eines gemisches aus cycloalkanon und cycloalkanol mit 5 bis 12 kohlenstoffatomen, insbesondere aus cyclohexanon und cyclohexanol
CA1049041A (fr) *	1972-11-23	1979-02-20	Stamicarbon B.V.	Procede de synthese de cycloalcanones et/ou de cycloalcanols

1975
- 1975-06-07 NL NL7506790A patent/NL7506790A/xx not_active Application Discontinuation
1976
- 1976-01-01 AR AR26349376A patent/AR206572A1/es active
- 1976-06-03 CA CA253,976A patent/CA1070328A/fr not_active Expired
- 1976-06-04 BE BE167662A patent/BE842635R/xx not_active IP Right Cessation
- 1976-06-04 ES ES448576A patent/ES448576A2/es not_active Expired
- 1976-06-04 DD DD19319576A patent/DD124971A6/xx unknown
- 1976-06-04 CH CH767120A patent/CH608774A5/xx not_active IP Right Cessation
- 1976-06-04 BR BR7603568A patent/BR7603568A/pt unknown
- 1976-06-04 FR FR7617017A patent/FR2313336A2/fr active Granted
- 1976-06-04 GB GB2326776A patent/GB1535869A/en not_active Expired
- 1976-06-04 DE DE19762625273 patent/DE2625273A1/de not_active Ceased
- 1976-06-07 IT IT2403376A patent/IT1061404B/it active
- 1976-06-07 MX MX16500676A patent/MX144251A/es unknown
- 1976-06-07 JP JP6638276A patent/JPS6033809B2/ja not_active Expired
- 1976-06-07 PL PL19019276A patent/PL101224B3/pl unknown

Also Published As

Publication number	Publication date
BE842635R (nl)	1976-12-06
AR206572A1 (es)	1976-07-30
DD124971A6 (fr)	1977-03-23
JPS51146437A (en)	1976-12-16
PL101224B3 (pl)	1978-12-30
CH608774A5 (en)	1979-01-31
FR2313336A2 (fr)	1976-12-31
FR2313336B2 (fr)	1981-06-12
GB1535869A (en)	1978-12-13
DE2625273A1 (de)	1976-12-16
ES448576A2 (es)	1977-07-16
MX144251A (es)	1981-09-18
IT1061404B (it)	1983-02-28
NL7506790A (nl)	1976-12-09
JPS6033809B2 (ja)	1985-08-05
BR7603568A (pt)	1977-01-04

Legal Events

Date	Code	Title	Description
1997-01-22	MKEX	Expiry

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EP0478331A2 (fr)	1992-04-01	Oxydation de cyclohexane
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US5334771A (en)	1994-08-02	Peroxidation of secondary carbon in alkanes and cycloalkanes
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