NO135864B - - Google Patents

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Info

Publication number: NO135864B
Authority: NO; Norway
Prior art keywords: vol; olefin; solution; pressure; trans
Prior art date: 1970-10-13

Application number

NO3748/71A

Other languages

English (en)

Norwegian (no)

Other versions

NO135864C (fr

Inventor

F Maspero

E Perrotti

Original Assignee

Snam Progetti

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.)

1970-10-13

Filing date

1971-10-12

Publication date

1977-03-07

1971-10-12 Application filed by Snam Progetti filed Critical Snam Progetti

1977-03-07 Publication of NO135864B publication Critical patent/NO135864B/no

1977-06-15 Publication of NO135864C publication Critical patent/NO135864C/no

Links

238000000034 method Methods 0.000 claims description 19
238000006243 chemical reaction Methods 0.000 claims description 13
150000001336 alkenes Chemical class 0.000 claims description 12
150000001993 dienes Chemical class 0.000 claims description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 9
239000003054 catalyst Substances 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 6
239000007858 starting material Substances 0.000 claims description 6
230000015572 biosynthetic process Effects 0.000 claims description 5
230000003197 catalytic effect Effects 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 4
238000004587 chromatography analysis Methods 0.000 claims description 4
APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 claims description 3
229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
238000004817 gas chromatography Methods 0.000 claims description 2
AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
238000004949 mass spectrometry Methods 0.000 claims description 2
BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 claims 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims 2
238000004458 analytical method Methods 0.000 claims 1
239000006227 byproduct Substances 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims 1
239000012299 nitrogen atmosphere Substances 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 14
239000001257 hydrogen Substances 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
150000002430 hydrocarbons Chemical class 0.000 description 3
-1 unsaturated acetylene compound Chemical class 0.000 description 3
229930195735 unsaturated hydrocarbon Natural products 0.000 description 3
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
239000011521 glass Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
239000000370 acceptor Substances 0.000 description 1
238000001994 activation Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000001273 butane Substances 0.000 description 1
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000007323 disproportionation reaction Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000007789 gas Substances 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
125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
239000000852 hydrogen donor Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000000178 monomer Substances 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07C5/50—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor with an organic compound as an acceptor
- C07C5/52—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor with an organic compound as an acceptor with a hydrocarbon as an acceptor, e.g. hydrocarbon disproportionation, i.e. 2CnHp -> CnHp+q + CnHp-q

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)

NO3748/71A 1970-10-13 1971-10-12 NO135864C (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT3089870		1970-10-13

Publications (2)

Publication Number	Publication Date
NO135864B true NO135864B (fr)	1977-03-07
NO135864C NO135864C (fr)	1977-06-15

Family

ID=11232715

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO3748/71A NO135864C (fr)	1970-10-13	1971-10-12

Country Status (14)

Country	Link
US (1)	US3849510A (fr)
JP (1)	JPS5320004B1 (fr)
BE (1)	BE773736A (fr)
CA (1)	CA960699A (fr)
CH (1)	CH550751A (fr)
DE (1)	DE2149934C3 (fr)
DK (1)	DK139096B (fr)
FR (1)	FR2114365A5 (fr)
GB (1)	GB1343469A (fr)
LU (1)	LU64052A1 (fr)
NL (1)	NL170526B (fr)
NO (1)	NO135864C (fr)
SE (1)	SE397340B (fr)
SU (1)	SU474966A3 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT981300B (it) *	1973-03-12	1974-10-10	Snam Progetti	Olii lubrificanti sintetici da cracking termico di polimeri ad altissima viscosita
JPS5534358A (en) *	1978-08-31	1980-03-10	Matsushita Electric Ind Co Ltd	Muting device of record player
US4670621A (en) *	1986-05-05	1987-06-02	Ethyl Corporation	Catalytic synthesis of olefins from paraffins
US4751344A (en) *	1986-05-05	1988-06-14	Ethyl Corporation	Catalytic synthesis of olefins from paraffins
WO2012061272A2 (fr) *	2010-11-02	2012-05-10	The University Of North Carolina At Chapel Hill	Synthèse de para-xylène et de toluène

1971
- 1971-10-06 DE DE2149934A patent/DE2149934C3/de not_active Expired
- 1971-10-08 SU SU1702300A patent/SU474966A3/ru active
- 1971-10-08 FR FR7136236A patent/FR2114365A5/fr not_active Expired
- 1971-10-11 BE BE773736A patent/BE773736A/fr unknown
- 1971-10-11 CH CH1479571A patent/CH550751A/fr not_active IP Right Cessation
- 1971-10-12 JP JP7991671A patent/JPS5320004B1/ja active Pending
- 1971-10-12 NO NO3748/71A patent/NO135864C/no unknown
- 1971-10-12 DK DK494271AA patent/DK139096B/da not_active IP Right Cessation
- 1971-10-12 LU LU64052D patent/LU64052A1/xx unknown
- 1971-10-12 GB GB4752371A patent/GB1343469A/en not_active Expired
- 1971-10-12 CA CA124,968A patent/CA960699A/en not_active Expired
- 1971-10-13 US US00189050A patent/US3849510A/en not_active Expired - Lifetime
- 1971-10-13 NL NLAANVRAGE7114053,A patent/NL170526B/xx not_active IP Right Cessation
- 1971-10-13 SE SE7112998A patent/SE397340B/xx unknown

Also Published As

Publication number	Publication date
GB1343469A (en)	1974-01-10
JPS5320004B1 (fr)	1978-06-24
CA960699A (en)	1975-01-07
SU474966A3 (ru)	1975-06-25
NL7114053A (fr)	1972-04-17
LU64052A1 (fr)	1972-04-21
DK139096C (fr)	1979-05-28
CH550751A (fr)	1974-06-28
DK139096B (da)	1978-12-18
DE2149934A1 (de)	1972-04-20
NL170526B (nl)	1982-06-16
BE773736A (fr)	1972-01-31
FR2114365A5 (fr)	1972-06-30
NO135864C (fr)	1977-06-15
US3849510A (en)	1974-11-19
DE2149934C3 (de)	1978-06-08
SE397340B (sv)	1977-10-31
DE2149934B2 (de)	1977-10-06

Publication	Publication Date	Title
US3013066A (en)	1961-12-12	Dimerization of alpha olefins with a group viii noble metal salt
Alderson et al.	1965	Olefin-to-olefin addition reactions
Bond et al.	1965	587. The hydrogenation of alkadienes. Part I. The hydrogenation of buta-1, 3-diene catalysed by the Noble Group VIII metals
US3513209A (en)	1970-05-19	Method of making 1,4-cyclohexadiene
Kitagawa et al.	1977	Total synthesis of humulene. A stereoselective approach
Silva et al.	1998	Selective linear dimerization of 1, 3-butadiene by palladium compounds immobilized into 1-n-butyl-3-methyl imidazolium ionic liquids
Ellis et al.	1966	The thermal unimolecular isomerisation of bicyclo [3, 1, 0] hex-2-ene and decomposition of cyclohexa-1, 4-diene
Greenlee et al.	1976	Olefin metathesis by rhenium carbonyl halide-alkylaluminum halide catalysts. Direct evidence for a coordinated carbene initiated process
Behr et al.	2014	Cross-metathesis of methyl 10-undecenoate with dimethyl maleate: an efficient protocol with nearly quantitative yields
US2448375A (en)	1948-08-31	Preparation of carboxylic acids
Sondheimer et al.	1961	Unsaturated macrocyclic compounds. XVIII. 1 the prototropic rearrangement of linear 1, 5-diynes to conjugated polyen-ynes
US2244645A (en)	1941-06-03	Process of dimerization
NO135864B (fr)	1977-03-07
Grubbs et al.	1979	Consideration of the mechanism of the transition metal catalyzed olefin metathesis reaction. Metathesis of cis, cis-2, 8-decadiene
Brieger et al.	1969	Synthesis of trans, trans-. alpha.-farnesene
US9944572B2 (en)	2018-04-17	Tandem transfer hydrogenation and oligomerization for hydrocarbon production
US3950450A (en)	1976-04-13	Process for producing 4-methyl-1-pentene
US3845152A (en)	1974-10-29	Selective isomerization of polyenes having terminal conjugated unsaturation
Villarreal et al.	2021	Efficient synthesis of styrene derivatives through ethenolysis of renewable propenylbenzenes
US2079490A (en)	1937-05-04	Maleic acid from diolefines
Benn et al.	1977	The ene reaction of maleic anhydride with alkenes
US2497304A (en)	1950-02-14	Preparation of carboxylic acid anhydrides
Neumann Jr	1964	Intramolecular cyclopropane formation from gem-diiodoalkanes and zinc-copper couple
Card et al.	1978	(Polystyrylbipyridine) palladium (0): Heterogeneous Catalyst for the Mild Hydrogenation of Dienes to Monoenes
Wells et al.	1970	The hydrogenation of alkadienes. Part V. The hydrogenation of trans-and of cis-penta-1, 3-diene catalysed by cobalt, nickel, copper, palladium, and platinum