CH414600A - Procédé pour la préparation de cyclo-oléfines - Google Patents

Procédé pour la préparation de cyclo-oléfines

Info

Publication number: CH414600A
Authority: CH; Switzerland
Prior art keywords: cyclo; hydrochloric acid; oxygen; reaction; cycloparaffin
Prior art date: 1961-07-18

Application number

CH855962A

Other languages

English (en)

French (fr)

Inventor

Brichta Corrado

Caprara Giuseppe

Cevidalli Guidobaldo

Original Assignee

Edison Soc

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.)

1961-07-18

Filing date

1962-07-17

Publication date

1966-06-15

1962-07-17 Application filed by Edison Soc filed Critical Edison Soc

1966-06-15 Publication of CH414600A publication Critical patent/CH414600A/fr

Links

238000000034 method Methods 0.000 title claims description 16
150000001925 cycloalkenes Chemical class 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 44
239000003054 catalyst Substances 0.000 claims description 23
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 18
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 16
229910052760 oxygen Inorganic materials 0.000 claims description 16
239000001301 oxygen Substances 0.000 claims description 16
OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 14
239000007789 gas Substances 0.000 claims description 12
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
230000003647 oxidation Effects 0.000 claims description 8
238000007254 oxidation reaction Methods 0.000 claims description 8
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
229910052802 copper Inorganic materials 0.000 claims description 7
239000010949 copper Substances 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 7
239000012190 activator Substances 0.000 claims description 6
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 5
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 5
239000000377 silicon dioxide Substances 0.000 claims description 5
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
-1 cyclic olefins Chemical class 0.000 claims description 4
229910052742 iron Inorganic materials 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 3
239000000395 magnesium oxide Substances 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
150000001805 chlorine compounds Chemical class 0.000 claims description 2
WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 claims description 2
239000004914 cyclooctane Substances 0.000 claims description 2
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
239000000463 material Substances 0.000 claims description 2
239000008262 pumice Substances 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
150000001342 alkaline earth metals Chemical class 0.000 claims 1
150000002505 iron Chemical class 0.000 claims 1
239000011819 refractory material Substances 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
230000003197 catalytic effect Effects 0.000 description 6
238000006356 dehydrogenation reaction Methods 0.000 description 6
235000013339 cereals Nutrition 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 3
238000006317 isomerization reaction Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
ATQUFXWBVZUTKO-UHFFFAOYSA-N 1-methylcyclopentene Chemical class CC1=CCCC1 ATQUFXWBVZUTKO-UHFFFAOYSA-N 0.000 description 2
238000001354 calcination Methods 0.000 description 2
238000005336 cracking Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910001514 alkali metal chloride Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910001617 alkaline earth metal chloride Inorganic materials 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000000919 ceramic Substances 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 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
150000002739 metals Chemical class 0.000 description 1
UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 1
GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
239000004576 sand Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/42—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor
- C07C5/48—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor with oxygen as an acceptor
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/42—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor
- C07C5/54—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor with an acceptor system containing at least two compounds provided for in more than one of the sub-groups C07C5/44 - C07C5/50
- C07C5/56—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor with an acceptor system containing at least two compounds provided for in more than one of the sub-groups C07C5/44 - C07C5/50 containing only oxygen and either halogens or halogen-containing compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CH855962A 1961-07-18 1962-07-17 Procédé pour la préparation de cyclo-oléfines CH414600A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT1326761		1961-07-18

Publications (1)

Publication Number	Publication Date
CH414600A true CH414600A (fr)	1966-06-15

Family

ID=11144344

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH855962A CH414600A (fr)	1961-07-18	1962-07-17	Procédé pour la préparation de cyclo-oléfines

Country Status (5)

Country	Link
CH (1)	CH414600A (da)
DK (1)	DK104978C (da)
ES (1)	ES279475A1 (da)
GB (1)	GB1016803A (da)
SE (1)	SE308305B (da)

1962
- 1962-07-13 SE SE788262A patent/SE308305B/xx unknown
- 1962-07-17 CH CH855962A patent/CH414600A/fr unknown
- 1962-07-17 GB GB2740662A patent/GB1016803A/en not_active Expired
- 1962-07-17 DK DK318962A patent/DK104978C/da active
- 1962-07-17 ES ES279475A patent/ES279475A1/es not_active Expired

Also Published As

Publication number	Publication date
GB1016803A (en)	1966-01-12
DK104978C (da)	1966-08-01
SE308305B (da)	1969-02-10
ES279475A1 (es)	1963-02-16

Publication	Publication Date	Title
CA1154425A (fr)	1983-09-27	Catalyseurs de fluoruration en phase gazeuse de derives chlores aliphatiques, a base de microbilles d'oxyde de chrome, et procedes de fluoruration utilisant ces catalyseurs
EP0002977A1 (fr)	1979-07-11	Catalyseurs à base d'argent pour la production d'oxyde d'éthylène
FR2700766A1 (fr)	1994-07-29	Procédé de fluoration de perchloréthylène ou du pentachloréthane.
EP0341165B1 (fr)	1992-09-09	Procédé de préparation du phénol
JPH01207137A (ja)	1989-08-21	触媒の担体及び触媒の製造方法並びにオレフィンの二量化方法
JPH08245443A (ja)	1996-09-24	有機化合物の連続的不均一接触気相部分酸化方法
CH414600A (fr)	1966-06-15	Procédé pour la préparation de cyclo-oléfines
EP0245653B1 (en)	1991-05-29	Production of high (z,z) content 1,5,9-tetradecatrieneand 1,5,9-tetradecatriene
US4668819A (en)	1987-05-26	Process for the manufacture of unsaturated esters of carboxylic acids
JPH0788318B2 (ja)	1995-09-27	イソブチレンの製造法
US5105049A (en)	1992-04-14	Olefin dimerization with hydrogen-treated catalysts
CH498792A (fr)	1970-11-15	Procédé d'oxychloruration de l'éthylène
JP2577833B2 (ja)	1997-02-05	アルカリ金属触媒組成物
US4328365A (en)	1982-05-04	Hydrocarbon oxidation via carbon monoxide reduced catalyst
SU428601A3 (ru)	1974-05-15	Способ получения индола
EP0000460B1 (fr)	1981-11-04	Catalyseurs à base d'argent et leur utilisation pour la production d'oxyde d'oléfines
JPH10259147A (ja)	1998-09-29	モノアルケニルベンゼン類の製造方法
US2977324A (en)	1961-03-28	Catalysts
JPH0237329B2 (da)	1990-08-23
WO1990014323A1 (fr)	1990-11-29	Procede pour la synthese d'hydrocarbures aromatiques alkyles
US5081093A (en)	1992-01-14	Product and process of hydrogen treatment of olefin dimerization catalysts
US4692321A (en)	1987-09-08	Oxidation of ammonia over a mixed catalyst bed of cobalt and aluminum oxides
EP0115887B1 (fr)	1987-04-01	Procédé pour l'obtention du 2,2,2-trifluoroéthanol
JPH08508750A (ja)	1996-09-17	多段式のオレフィンの異性化
JPS63196526A (ja)	1988-08-15	内部オレフインの製造方法