US3631209A - Preparation of cycloolefins - Google Patents

Preparation of cycloolefins Download PDF

Info

Publication number: US3631209A
Authority: US; United States
Prior art keywords: employed; cyclopentadiene; pentadiene; column; piperylene
Prior art date: 1970-06-22
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

US48461A

Other languages

English (en)

Inventor

Kenneth J Frech

David A Hutchings

Frederic H Hoppstock

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.)

Goodyear Tire and Rubber Co

Original Assignee

Goodyear Tire and Rubber Co

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.)

1970-06-22

Filing date

1970-06-22

Publication date

1971-12-28

1970-06-22 Application filed by Goodyear Tire and Rubber Co filed Critical Goodyear Tire and Rubber Co

1971-12-28 Application granted granted Critical

1971-12-28 Publication of US3631209A publication Critical patent/US3631209A/en

1988-12-28 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title abstract description 7
150000001925 cycloalkenes Chemical class 0.000 title description 6
238000000034 method Methods 0.000 abstract description 18
239000002815 homogeneous catalyst Substances 0.000 abstract description 14
150000001993 dienes Chemical class 0.000 abstract description 13
150000001336 alkenes Chemical class 0.000 abstract 1
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 40
PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 31
PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 29
-1 cyclic olefins Chemical class 0.000 description 22
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
239000003054 catalyst Substances 0.000 description 12
238000002474 experimental method Methods 0.000 description 11
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 9
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical group S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 7
239000003085 diluting agent Substances 0.000 description 7
239000007789 gas Substances 0.000 description 7
229910000037 hydrogen sulfide Inorganic materials 0.000 description 7
JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
239000000376 reactant Substances 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 description 4
WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 4
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 4
239000001307 helium Substances 0.000 description 4
229910052734 helium Inorganic materials 0.000 description 4
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 4
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical class C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 3
150000001941 cyclopentenes Chemical class 0.000 description 3
238000006356 dehydrogenation reaction Methods 0.000 description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
229910000043 hydrogen iodide Inorganic materials 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 3
APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 description 2
XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 2
CJSBUWDGPXGFGA-UHFFFAOYSA-N 4-methylpenta-1,3-diene Chemical compound CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
229910000831 Steel Inorganic materials 0.000 description 2
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 2
HIVLDXAAFGCOFU-UHFFFAOYSA-N ammonium hydrosulfide Chemical compound [NH4+].[SH-] HIVLDXAAFGCOFU-UHFFFAOYSA-N 0.000 description 2
229940107816 ammonium iodide Drugs 0.000 description 2
UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 2
FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
239000010959 steel Substances 0.000 description 2
AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
239000010425 asbestos Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
229910000423 chromium oxide Inorganic materials 0.000 description 1
238000005336 cracking Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
CNFQJGLKUZBUBD-TXHUMJEOSA-N hexa-1,5-diene;(3e)-hexa-1,3-diene;(4e)-hexa-1,4-diene Chemical class CC\C=C\C=C.C\C=C\CC=C.C=CCCC=C CNFQJGLKUZBUBD-TXHUMJEOSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
238000009413 insulation Methods 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
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
238000011017 operating method Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000005070 sampling Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000012546 transfer Methods 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
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/31—Rearrangement of carbon atoms in the hydrocarbon skeleton changing the number of rings
- 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
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/373—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen with simultaneous isomerisation

Definitions

This invention is directed to the preparation of cycloolefins from open chain conjugated diolefins. More particularly, it is directed to the preparation of cyclopentene and cyclopentadiene from 1,3-pentadiene and methyl substituted cyclopentadiene and methyl substituted cyclopentenes from methyl substituted 1,3-pentadienes and methyl substituted cyclopentenes and methyl substituted cyclopentadienes and cyclohexadienes from open chain conjugated hexadienes, such as 1,3-hexadiene and 2,4- hexadiene.
Cycloolefins and cyclo diolefins are presently obtained in limited quantities as by-products as naphtha and gas oil cracking.
the naphtha and gas oil crackers are operated in a manner to produce maximum amounts of ethylene and other cycloolefins. Therefore, only limited quantities of cycloolefin and cyclo diolefin are available for use as starting materials to prepare other products such as resins, insecticides and the like.
1,3-pentadiene and methyl substituted 1,3-pentadiene which are not now utilized could be employed to produce more valuable products.
1,3- and 2,4-hexadiene could be utilized in accordance with this invention to produce more valuable methyl substituted cyclopentadiene and cyclohexadienes.
2,438,400 there is described that 1,3- pentadiene in pure form or admixed with normal pentane and normal pentene can be converted to 1,3-cyclopentadiene on contact with a catalyst such as CR O on alumina at 400 C. to 700 C. at 10 to 100 millimeters of pressure.
a catalyst such as CR O on alumina at 400 C. to 700 C. at 10 to 100 millimeters of pressure.
2,438,401 is described a process for the production of cyclopentadiene-1,3 by contact of 1,3- pentadiene with SiC at 450 C. to 650 C. and 10 to 200 millimeters of pressure.
2,438,402 is described the cyclization of 1,3-pentadiene to form 1,3- cyclopentadiene by bringing 1,3-pentadiene into contact with fused alumina at 400 C. to 700 C. at 10 to 200 millimeters of pressure.
2,438,403 cyclopentadiene is derived from 1,3-pentadiene by contact with sub-divided iron or steel at 450 C. to 650 C. and at pressures from 10 to 200 millimeters.
thermo-dehydrogenation processes either were truly thermo-dehydrogenation processes or were processes which employed fixed bed catalyst systems such as the activated silica gel, the chromium oxide on alumina or the silica carbide or fused alumina or sub-divided iron or steel.
fixed bed catalyst systems such as the activated silica gel, the chromium oxide on alumina or the silica carbide or fused alumina or sub-divided iron or steel.
the present invention uses a homogeneous catalyst system.
cyclic olefins and cyclic diolefins are prepared from open-chain diolefins by heating in the presence of homogeneous catalysts.
All that is required to perform the present invention is to pass the open-chain diolefin, for instance, 1,3-pentadiene and the homogeneous catalyst system, through a tubular reactor heated to the desired temperature.
the open-chain diolefins which are useful as the reactants in this invention are 1,3-pentadiene from which can be formed cyclopentene and cyclopentadiene; 4-methyl-l,3- pentadiene from which can be formed a methyl substituted cyclopentene and a methyl substituted cyclopentadiene; 2- methyl-l,3-pentadiene may be employed from which can be obtained methyl substituted cyclopentadiene and cyclopentene; 3-methyl-l,3-pentadiene may be employed and methyl-substituted cyclopentenes and methyl substituted cyclopentadienes are obtained.
1,3- and 2,4hexadienes from which there can be obtained
the catalyst employed in this invention can be a variety of catalysts which are homogeneous in nature.
Representative of the catalysts which can be employed in this invention are: methyl mercaptan, ethyl mercaptan, ammonium sulfide, ammonium hydrosulfide, hydrogen bromide, ammonium bromide, dibromo methane, bromo chloro methane, allyl bromide, bromine, hydrogen iodide, iodo methane, iodine, ammonium iodide, carbon disulfide, dimethyldisulfide and carbonyl sulfide.
One of the more preferred homogeneous catalyst is hydrogen sulfide.
the temperature employed in the process of this invention can range from about 450 C. to about 1000 C. with a more preferred range of about 550 C. to about 800 C. and still more preferred range of about 575 C. to 750 C.
the process can be employed with the reactants in the pure state or a diluent may be employed. It is usually desirable to employ a diluent for heat transfer purposes.
a diluent for heat transfer purposes.
the diluents which might be mentioned as suitable are steam, nitrogen, methane, ethane, pentane, and other hydrocarbon gases or inert gases which are stable under the conditions to be employed.
the diluent to open chain diolefin mole ratio may vary over a very Wide range; that is, from 0 to 25/1.
the residence time at which the open chain diolefin is heated is not critical and may vary from a low of 0.01 second up to 1 minute with a more preferred time being from 0.25 second to 10 seconds and a still more preferred range would be from 0.75 second to 5 seconds.
the amount of catalyst required in the process of this invention has not been found to be too critical except that, of course, a catalytic amount must be employed. For instance, good results have been obtained when as little catalyst as 0.1 mole percent up to 200 mole percent based on the moles of the open-chain diolefin as the reactant. However, a more preferred range is from about 10 mole percent to about 100 mole percent with the most preferred being from about 15 mole percent to about mole percent.
column 1 is the run number
column 2 is the mole percent of hydrogen sulfide based on the piperylene
column 3 is the temperature in degrees centigrade
column 4 is the residence time in seconds
column 5 is the cyclopentene yield in mole percent
column 6 is the cyclopentadiene yield in mole percent
column 7 is the reaction selectivity to cyclic unsaturated products including both cyclopentene and cyclopentadiene in percent
column 8 is the piperylene in mole percent.
pentene CPD percent percent As can be seen from the results set forth in the table above, when piperylene is heated in the presence of hydrogen sulfide, a very large increase in the percent yield of cyclopentene and cyclopentadiene is obtained as well as a vast improvement in reaction selectivity to cyclic olefins.
column 1 is the run number
column 2 is the catalyst and the amount of catalyst employed reported in mole percent based on the piperylene charged
column 3 is the temperature in degrees centigrade
column 4 is the residence time in seconds
column 5 is the yield in mole percent of cyclopentadiene obtained
column 6 is the mole percent of cyclopentadiene obtained
column 7 is the reaction selectivity in percent of cyclic olefins obtained
column 8 is the piperylene converted, represented in mole percent.
the method of preparing cyclic olefins and cyclic diolefins comprising heating at least one acyclic diolefin from the group consisting of acyclic pentadienes, methyl substituted acyclic pentadienes and acyclic hexadienes to temperatures ranging from about 550 C.
acyclic diolefins are in contact with the homogeneous catalyst selected from the group consisting of hydrogen sulfide, methyl mercaptan, ethyl mercaptan, ammonium sulfide, ammonium hydrosulfide, hydrogen bromide, ammonium bromide, dibromo methane, bromo chloro methane, allyl bromide, bromine, hydrogen iodide, iodo methane, iodine, ammonium iodide, carbon disulfide, dimethyl-disulfide and carbonyl sulfide.
the homogeneous catalyst selected from the group consisting of hydrogen sulfide, methyl mercaptan, ethyl mercaptan, ammonium sulfide, ammonium hydrosulfide, hydrogen bromide, ammonium bromide, dibromo methane, bromo chloro methane,

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)

US48461A 1970-06-22 1970-06-22 Preparation of cycloolefins Expired - Lifetime US3631209A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US4846170A	1970-06-22	1970-06-22

Publications (1)

Publication Number	Publication Date
US3631209A true US3631209A (en)	1971-12-28

Family

ID=21954716

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
US48461A Expired - Lifetime US3631209A (en)	1970-06-22	1970-06-22	Preparation of cycloolefins

Country Status (10)

Country	Link
US (1)	US3631209A (fr)
JP (1)	JPS549197B1 (fr)
BE (1)	BE768444A (fr)
CA (1)	CA948218A (fr)
DE (1)	DE2126857C3 (fr)
ES (1)	ES391520A1 (fr)
FR (1)	FR2096110A5 (fr)
GB (1)	GB1347319A (fr)
NL (1)	NL7108594A (fr)
ZA (1)	ZA713172B (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5516953A (en) *	1994-03-08	1996-05-14	E. I. Du Pont De Nemours And Company	Process for the preparation of optically active cycloolefins
WO2017078903A1 (fr) *	2015-11-04	2017-05-11	Exxonmobil Chemical Patents Inc.	Procédé et système de fabrication de cyclopentadiène et/ou de dicyclopentadiène
WO2017078899A3 (fr) *	2015-11-04	2017-07-13	Exxonmobil Chemical Patents Inc.	Procédé de conversion de composés c5 acycliques en composés c5 cycliques et composition catalytique à utiliser dans celui-ci
WO2017078898A3 (fr) *	2015-11-04	2017-07-13	Exxonmobil Chemical Patents Inc.	Procédé de conversion de composés c5c acycliques en composés c5 cycliques et composition catalytique utilisées dans le procédé
US9849440B2 (en)	2015-11-04	2017-12-26	Exxonmobil Chemical Patents Inc.	Process for conversion of acyclic C5 compounds to cyclic C5 compounds and catalyst composition for use therein
US9856187B2 (en)	2015-11-04	2018-01-02	Exxonmobil Chemical Patents Inc.	Process for conversion of acyclic C5 compounds to cyclic C5 compounds and catalyst composition for use therein
WO2017078896A3 (fr) *	2015-11-04	2018-03-01	Exxonmobil Chemical Patents Inc.	Procédé de conversion de composés c5 acycliques en composés c5 cycliques et composition catalytique à utiliser dans celui-ci
WO2017078897A3 (fr) *	2015-11-04	2018-03-01	Exxonmobil Chemical Patents Inc.	Procédé de conversion de composés c5 acycliques en composés c5 cycliques et composition catalytique pour utilisation dans celui-ci
US9919988B2 (en)	2015-11-04	2018-03-20	Exxonmobil Chemical Patents Inc.	Process and system for making cyclopentadiene and/or dicyclopentadiene

1970
- 1970-06-22 US US48461A patent/US3631209A/en not_active Expired - Lifetime
1971
- 1971-05-17 ZA ZA713172A patent/ZA713172B/xx unknown
- 1971-05-18 GB GB1550371*[A patent/GB1347319A/en not_active Expired
- 1971-05-25 ES ES391520A patent/ES391520A1/es not_active Expired
- 1971-05-25 CA CA113,741A patent/CA948218A/en not_active Expired
- 1971-05-27 DE DE2126857A patent/DE2126857C3/de not_active Expired
- 1971-06-09 FR FR7120865A patent/FR2096110A5/fr not_active Expired
- 1971-06-11 BE BE768444A patent/BE768444A/fr unknown
- 1971-06-18 JP JP4339071A patent/JPS549197B1/ja active Pending
- 1971-06-22 NL NL7108594A patent/NL7108594A/xx not_active Application Discontinuation

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5516953A (en) *	1994-03-08	1996-05-14	E. I. Du Pont De Nemours And Company	Process for the preparation of optically active cycloolefins
WO2017078903A1 (fr) *	2015-11-04	2017-05-11	Exxonmobil Chemical Patents Inc.	Procédé et système de fabrication de cyclopentadiène et/ou de dicyclopentadiène
WO2017078899A3 (fr) *	2015-11-04	2017-07-13	Exxonmobil Chemical Patents Inc.	Procédé de conversion de composés c5 acycliques en composés c5 cycliques et composition catalytique à utiliser dans celui-ci
WO2017078898A3 (fr) *	2015-11-04	2017-07-13	Exxonmobil Chemical Patents Inc.	Procédé de conversion de composés c5c acycliques en composés c5 cycliques et composition catalytique utilisées dans le procédé
US9849440B2 (en)	2015-11-04	2017-12-26	Exxonmobil Chemical Patents Inc.	Process for conversion of acyclic C5 compounds to cyclic C5 compounds and catalyst composition for use therein
US9856187B2 (en)	2015-11-04	2018-01-02	Exxonmobil Chemical Patents Inc.	Process for conversion of acyclic C5 compounds to cyclic C5 compounds and catalyst composition for use therein
WO2017078896A3 (fr) *	2015-11-04	2018-03-01	Exxonmobil Chemical Patents Inc.	Procédé de conversion de composés c5 acycliques en composés c5 cycliques et composition catalytique à utiliser dans celui-ci
WO2017078897A3 (fr) *	2015-11-04	2018-03-01	Exxonmobil Chemical Patents Inc.	Procédé de conversion de composés c5 acycliques en composés c5 cycliques et composition catalytique pour utilisation dans celui-ci
US9919988B2 (en)	2015-11-04	2018-03-20	Exxonmobil Chemical Patents Inc.	Process and system for making cyclopentadiene and/or dicyclopentadiene
US10011539B2 (en)	2015-11-04	2018-07-03	Exxonmobil Chemical Patents Inc.	Process for conversion of acyclic C5 compounds to cyclic C5 compounds and catalyst composition for use therein
US10294175B2 (en)	2015-11-04	2019-05-21	Exxonmobil Chemical Patents Inc.	Process for conversion of acyclic C5 compounds to cyclic C5 compounds and catalyst composition for use therein

Also Published As

Publication number	Publication date
GB1347319A (en)	1974-02-27
ES391520A1 (es)	1973-06-16
FR2096110A5 (fr)	1972-02-11
DE2126857A1 (fr)	1971-12-30
JPS549197B1 (fr)	1979-04-21
BE768444A (fr)	1971-11-03
NL7108594A (fr)	1971-12-24
ZA713172B (en)	1972-01-26
CA948218A (en)	1974-05-28
DE2126857C3 (de)	1981-12-17
DE2126857B2 (de)	1981-01-15

Publication	Publication Date	Title
US2359759A (en)	1944-10-10	Purification and production of olefins
US3631209A (en)	1971-12-28	Preparation of cycloolefins
US3303235A (en)	1967-02-07	Unsaturated hydrocarbons by oxidative dehydrogenation over a catalyst comprising zinc and iron
US2438041A (en)	1948-03-16	Process of producing styrene from butadiene
US3801661A (en)	1974-04-02	Selective process for the continuous dyhydrogenation of nonaromatic hydrocarbons
US3751514A (en)	1973-08-07	Preparation of isobutylene and propylene from isobutane
US3342890A (en)	1967-09-19	Process of dehydrogenation
US2079490A (en)	1937-05-04	Maleic acid from diolefines
US4287378A (en)	1981-09-01	Conversion of olefinic compounds
US3917736A (en)	1975-11-04	Oxidative dehydrogenation of 2,3-dimethyl-butenes to 2,3-dimethylbutadiene
US3274285A (en)	1966-09-20	Process for dehydrogenating
US3268611A (en)	1966-08-23	Process for dehydrogenating hydrocarbons
US3773850A (en)	1973-11-20	Process for dehydrogenation of propane
US2403439A (en)	1946-07-09	Process for isomerizing monoolefins
US3278630A (en)	1966-10-11	Production of ethylene
US3903189A (en)	1975-09-02	Oxidative dehydrogenation of olefins to diolefins
US3113984A (en)	1963-12-10	Oxidative dehydrogenation
US3313858A (en)	1967-04-11	Isomerization of non-terminal olefins
US3317626A (en)	1967-05-02	Olefin pyrolysis initiators
US3287438A (en)	1966-11-22	Modified cracking process
US4210603A (en)	1980-07-01	Production of cyclic hydrocarbons from n-butenes
US3254136A (en)	1966-05-31	Methyl mercaptan promoted pyrolysis of olefins
US3306950A (en)	1967-02-28	Dehydrogenation of hydrocarbons in the presence of oxygen, chlorine and a group vi-b catalyst
US3366703A (en)	1968-01-30	Modified pyrolysis systems for converting olefins to diolefins
US3463828A (en)	1969-08-26	Bis(cycloalkenyl)-substituted olefins