BE504161A - - Google Patents
Info
- Publication number
- BE504161A BE504161A BE504161DA BE504161A BE 504161 A BE504161 A BE 504161A BE 504161D A BE504161D A BE 504161DA BE 504161 A BE504161 A BE 504161A
- Authority
- BE
- Belgium
- Prior art keywords
- olefins
- polymerized
- formation
- hydrocarbons
- carbon atoms
- Prior art date
Links
- 150000001336 alkenes Chemical class 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 31
- 238000006471 dimerization reaction Methods 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- 150000002430 hydrocarbons Chemical class 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 238000005755 formation reaction Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 239000000539 dimer Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229910052733 gallium Inorganic materials 0.000 claims description 3
- 229910052738 indium Inorganic materials 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium(0) Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium Chemical group [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 2
- 125000002524 organometallic group Chemical group 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 230000002035 prolonged Effects 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 29
- YWAKXRMUMFPDSH-UHFFFAOYSA-N Pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 11
- 238000004821 distillation Methods 0.000 description 9
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-Hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methylpent-1-ene Chemical group CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- -1 NaBe (C2H5) 3 Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N Aluminium hydride Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000000383 tetramethylene group Chemical class [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 3
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- WYTGDNHDOZPMIW-UHOFOFEASA-O Serpentine Natural products O=C(OC)C=1[C@@H]2[C@@H]([C@@H](C)OC=1)C[n+]1c(c3[nH]c4c(c3cc1)cccc4)C2 WYTGDNHDOZPMIW-UHOFOFEASA-O 0.000 description 2
- 229910052790 beryllium Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 229940069096 dodecene Drugs 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000006011 modification reaction Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 2
- IRUDSQHLKGNCGF-UHFFFAOYSA-N 2-methylhex-1-ene Chemical group CCCCC(C)=C IRUDSQHLKGNCGF-UHFFFAOYSA-N 0.000 description 1
- XTVRLCUJHGUXCP-UHFFFAOYSA-N 3-methylideneheptane Chemical compound CCCCC(=C)CC XTVRLCUJHGUXCP-UHFFFAOYSA-N 0.000 description 1
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-Heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 1
- RWASOQSEFLDYLC-UHFFFAOYSA-N BeH2 Chemical compound [BeH2] RWASOQSEFLDYLC-UHFFFAOYSA-N 0.000 description 1
- CDWYRCWQKXNBCD-UHFFFAOYSA-N CCCC=C.CCCCC=C Chemical compound CCCC=C.CCCCC=C CDWYRCWQKXNBCD-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N Decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- 229910010199 LiAl Inorganic materials 0.000 description 1
- 229910010084 LiAlH4 Inorganic materials 0.000 description 1
- 210000003141 Lower Extremity Anatomy 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N Nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- CCCMONHAUSKTEQ-UHFFFAOYSA-N Octadecene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 1
- WHFQAROQMWLMEY-UHFFFAOYSA-N Propylene dimer Chemical compound CC=C.CC=C WHFQAROQMWLMEY-UHFFFAOYSA-N 0.000 description 1
- 210000001364 Upper Extremity Anatomy 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000091 aluminium hydride Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- VRWRYXRXVZEJKF-UHFFFAOYSA-N beryllium;ethane Chemical compound [Be+2].[CH2-]C.[CH2-]C VRWRYXRXVZEJKF-UHFFFAOYSA-N 0.000 description 1
- OCFSGVNHPVWWKD-UHFFFAOYSA-N butylaluminum Chemical compound [Al].[CH2]CCC OCFSGVNHPVWWKD-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic Effects 0.000 description 1
- 101700043453 chch-3 Proteins 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- WZHKDGJSXCTSCK-UHFFFAOYSA-N hept-3-ene Chemical compound CCCC=CCC WZHKDGJSXCTSCK-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000001737 promoting Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001340 slower Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001131 transforming Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/26—Catalytic processes with hydrides or organic compounds
- C07C2/30—Catalytic processes with hydrides or organic compounds containing metal-to-carbon bond; Metal hydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- C07C2531/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE504161A true BE504161A (xx) |
Family
ID=145102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE504161D BE504161A (xx) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE504161A (xx) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2781410A (en) * | 1953-04-04 | 1957-02-12 | Ziegler | Polymerization of ethylene in the presence of an aluminum trialkyl catalyst |
| US2871276A (en) * | 1954-08-11 | 1959-01-27 | Standard Oil Co | Polymerization of alpha olefins in the presence of an air3 catalyst |
| US3076047A (en) * | 1955-05-09 | 1963-01-29 | Collier Carbon & Chemical Co | Polymerization of olefins and aluminum hydride activators therefor |
-
0
- BE BE504161D patent/BE504161A/fr unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2781410A (en) * | 1953-04-04 | 1957-02-12 | Ziegler | Polymerization of ethylene in the presence of an aluminum trialkyl catalyst |
| US2871276A (en) * | 1954-08-11 | 1959-01-27 | Standard Oil Co | Polymerization of alpha olefins in the presence of an air3 catalyst |
| US3076047A (en) * | 1955-05-09 | 1963-01-29 | Collier Carbon & Chemical Co | Polymerization of olefins and aluminum hydride activators therefor |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FR2523149A1 (fr) | Nouveau catalyseur supporte palladium-or, sa preparation et son utilisation dans les reactions d'hydrogenation selective d'hydrocarbures diolefiniques et/ou acetyleniques | |
| FR2715154A1 (fr) | Procédé de production d'oléfines alpha légères de pureté améliorée par oligomérisation, de l'éthylène. | |
| EP0151356A1 (fr) | Procédé d'hydrogénation sélective en présence de solvant des composés acétyléniques d'une coupe d'hydrocarbures C4 riche en butadiène | |
| EP0608156A1 (fr) | Procédé perfectionné pour oligomériser les acides et les esters polyinsaturés, les produits obtenus et leurs utilisations | |
| BE504161A (xx) | ||
| Carlton et al. | Rhodium (I)-catalysed dimerisation of terminal acetylenes at ambient temperature and pressure | |
| CH381215A (fr) | Procédé de préparation de l'isoprène | |
| CH622425A5 (xx) | ||
| BE540317A (xx) | ||
| EP0002411B1 (fr) | Catalyseur constitué d'un mélange de chlorure de dinitrosylfer et de bis (cyclooctadiène) nickel et son utilisation pour la dimérisation des dioléfines conjuguées | |
| EP0005659B1 (fr) | Procédé pour diluer des produits de parfumerie à l'aide de dimères d'alpha-méthylstyrène et/ou de dimères de terpènes, mélange pour la mise en oeuvre d'un tel procédé et composition de parfumerie ainsi diluée | |
| BE527736A (xx) | ||
| BE594803A (xx) | ||
| JP2008519802A (ja) | 長鎖内部脂肪族三級アミン類の製造方法 | |
| FR2981066A1 (fr) | Procede de preparation de jet fuel a partir de molecules issues de la biomasse. | |
| FR2496636A1 (fr) | Olefines superieures oligomerisees et leur utilisation dans des compositions lubrifiantes | |
| BE340443A (xx) | ||
| BE604880A (xx) | ||
| BE573484A (xx) | ||
| FR2492810A1 (fr) | Procede d'oligomerisation catalytique d'olefines normales contenant deux a dix atomes de carbone | |
| FR2552080A1 (fr) | Procede ameliore de synthese du butene-1 par dimerisation de l'ethylene | |
| BE589804A (xx) | ||
| BE371589A (xx) | ||
| CH255406A (fr) | Procédé de fabrication de composés carbonyliques à partir d'acides carboxyliques. | |
| BE550312A (xx) |