NO135864B - - Google Patents
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- Publication number
- NO135864B NO135864B NO3748/71A NO374871A NO135864B NO 135864 B NO135864 B NO 135864B NO 3748/71 A NO3748/71 A NO 3748/71A NO 374871 A NO374871 A NO 374871A NO 135864 B NO135864 B NO 135864B
- Authority
- NO
- Norway
- Prior art keywords
- vol
- olefin
- solution
- pressure
- trans
- Prior art date
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3089870 | 1970-10-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO135864B true NO135864B (OSRAM) | 1977-03-07 |
| NO135864C NO135864C (OSRAM) | 1977-06-15 |
Family
ID=11232715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3748/71A NO135864C (OSRAM) | 1970-10-13 | 1971-10-12 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3849510A (OSRAM) |
| JP (1) | JPS5320004B1 (OSRAM) |
| BE (1) | BE773736A (OSRAM) |
| CA (1) | CA960699A (OSRAM) |
| CH (1) | CH550751A (OSRAM) |
| DE (1) | DE2149934C3 (OSRAM) |
| DK (1) | DK139096B (OSRAM) |
| FR (1) | FR2114365A5 (OSRAM) |
| GB (1) | GB1343469A (OSRAM) |
| LU (1) | LU64052A1 (OSRAM) |
| NL (1) | NL170526B (OSRAM) |
| NO (1) | NO135864C (OSRAM) |
| SE (1) | SE397340B (OSRAM) |
| SU (1) | SU474966A3 (OSRAM) |
Families Citing this family (5)
| 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 (en) * | 2010-11-02 | 2012-05-10 | The University Of North Carolina At Chapel Hill | Synthesis of para-xylene and toluene |
-
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/xx 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 LU LU64052D patent/LU64052A1/xx unknown
- 1971-10-12 CA CA124,968A patent/CA960699A/en not_active Expired
- 1971-10-12 NO NO3748/71A patent/NO135864C/no unknown
- 1971-10-12 GB GB4752371A patent/GB1343469A/en not_active Expired
- 1971-10-12 DK DK494271AA patent/DK139096B/da not_active IP Right Cessation
- 1971-10-13 NL NLAANVRAGE7114053,A patent/NL170526B/xx not_active IP Right Cessation
- 1971-10-13 SE SE7112998A patent/SE397340B/xx unknown
- 1971-10-13 US US00189050A patent/US3849510A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB1343469A (en) | 1974-01-10 |
| CA960699A (en) | 1975-01-07 |
| DE2149934C3 (de) | 1978-06-08 |
| FR2114365A5 (OSRAM) | 1972-06-30 |
| JPS5320004B1 (OSRAM) | 1978-06-24 |
| DK139096B (da) | 1978-12-18 |
| NL170526B (nl) | 1982-06-16 |
| NL7114053A (OSRAM) | 1972-04-17 |
| SE397340B (sv) | 1977-10-31 |
| DE2149934A1 (de) | 1972-04-20 |
| LU64052A1 (OSRAM) | 1972-04-21 |
| CH550751A (fr) | 1974-06-28 |
| SU474966A3 (ru) | 1975-06-25 |
| DK139096C (OSRAM) | 1979-05-28 |
| NO135864C (OSRAM) | 1977-06-15 |
| BE773736A (fr) | 1972-01-31 |
| US3849510A (en) | 1974-11-19 |
| DE2149934B2 (de) | 1977-10-06 |
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