ZA200208320B - Process for the selective isomerization of alpha-olefins in the presence of vinylidene olefins. - Google Patents
Process for the selective isomerization of alpha-olefins in the presence of vinylidene olefins. Download PDFInfo
- Publication number
- ZA200208320B ZA200208320B ZA200208320A ZA200208320A ZA200208320B ZA 200208320 B ZA200208320 B ZA 200208320B ZA 200208320 A ZA200208320 A ZA 200208320A ZA 200208320 A ZA200208320 A ZA 200208320A ZA 200208320 B ZA200208320 B ZA 200208320B
- Authority
- ZA
- South Africa
- Prior art keywords
- olefins
- isomerization
- olefin
- alpha
- vinylidene
- Prior art date
Links
- 238000006317 isomerization reaction Methods 0.000 title claims description 39
- 239000004711 α-olefin Substances 0.000 title claims description 31
- 238000000034 method Methods 0.000 title claims description 30
- -1 vinylidene olefins Chemical class 0.000 title claims description 22
- 150000001336 alkenes Chemical class 0.000 claims description 37
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 33
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 10
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052707 ruthenium Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- WYRXRHOISWEUST-UHFFFAOYSA-K ruthenium(3+);tribromide Chemical compound [Br-].[Br-].[Br-].[Ru+3] WYRXRHOISWEUST-UHFFFAOYSA-K 0.000 claims description 3
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims 2
- PMMMCGISKBNZES-UHFFFAOYSA-K ruthenium(3+);tribromide;hydrate Chemical compound O.Br[Ru](Br)Br PMMMCGISKBNZES-UHFFFAOYSA-K 0.000 claims 1
- BIXNGBXQRRXPLM-UHFFFAOYSA-K ruthenium(3+);trichloride;hydrate Chemical compound O.Cl[Ru](Cl)Cl BIXNGBXQRRXPLM-UHFFFAOYSA-K 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000006384 oligomerization reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 241000894007 species Species 0.000 description 3
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- JKXCZYCVHPKTPK-UHFFFAOYSA-N hydrate;trihydrochloride Chemical compound O.Cl.Cl.Cl JKXCZYCVHPKTPK-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical class C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 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
- C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
- C07C5/25—Migration of carbon-to-carbon double bonds
- C07C5/2506—Catalytic processes
- C07C5/2525—Catalytic processes with inorganic acids; with salts or anhydrides of acids
- C07C5/2543—Acids of halogen; Salts thereof
- C07C5/255—Metal halides; Complexes thereof with organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/128—Compounds comprising a halogen and an iron group metal or a platinum group metal
- C07C2527/13—Platinum group metals
Description
PROCESS FOR THE SELECTIVE ISOMERIZATION OF ALPHA-OLEFINS IN THE
PRESENCE OF VINYLIDENE OLEFINS
. RELATIONSHIP TO PRIOR APPLICATIONS (Not Applicable)
STATEMENT REGARDING FEDERALLY FUNDED RESEARCH
(Not Applicable)
The invention generally relates to a process for isomerizing alpha-olefins to internal olefins without significant concurrent isomerization of vinylidene olefins also present in the reaction mixture.
In the catalytic isomerization of olefins, it is common that isomerization of a vinylidene olefin to a trisubstituted olefin (Reaction 1 below) proceeds more readily than isomerization of an alpha-olefin to an internal olefin (Reaction 2 below) when both are present in the same reaction mixture. ——=CH — C——CH3 : 2 0 : REACTION 1 - ISOMERIZATION OF A VINYLIDENE
CH)—CH—CH3—R — CH3—CH=—CH—R ’ REACTION 2 - ISOMERIZATION OF AN ALPHA-OLEFIN 3 In Reactions 1 and 2, R and R' are monovalent groups such as straight or branched alkyl groups or aryl groups typically in the range of about 1-30 carbon atoms. Some of the hydrogen atoms in the R and R’ groups may optionally be substituted with groups that do not interfere in the isomerization reaction.
Accordingly, when both vinylidenes and alpha-olefins are present, it has been difficult to selectively isomerize alpha-olefins to internal olefins without also ' isomerizing the vinylidene olefins. The present invention addresses this problem and provides a catalytic process for accomplishing the selective isomerization of alpha- to 5 olefins to internal olefins in the presence of vinylidene olefins without substantial isomerization of the vinylidenes.
This invention relates to a process for the conversion of olefins. More specifically it relates to the isomerization of alpha olefins to internal olefins wherein vinylidene olefins are also present in the alpha olefin feed or reaction mixture. It has been found that the alpha olefins may be catalytically isomerized to internal olefins without significant concurrent isomerization of vinylidene olefins to trisubstituted olefins.
The selective isomerization process utilizes a metal-based homogeneous or heterogeneous catalyst. The catalysts used in the process are ruthenium trihalides including ruthenium trihalide hydrates. The preferred catalysts are ruthenium trichloride and ruthenium tribromide including the various hydrated forms of either.
Investigators Jochem U. Koehler and Hans L. Krauss (Journal of Molecular
Catalysis, 1997, Volume 123, Number 1, Pages 49-64) have reported the use of
RuCl;*3H,0 as an active olefin isomerization catalyst. However, there is no disclosure what-so-ever in the reference regarding selective isomerization of alpha olefins in the presence of vinylidene olefins.
The ruthenium trihalide (RuX,) catalysts of this invention may be employed in homogeneous form, dissolved in neat liquid olefin or a mixture of olefin and a solvent.
Alcohols are effective solvents for the RuX, compounds of this invention. The selective alpha-olefin isomerization process of this invention using RuX, compounds : may be conducted at temperatures in the range of about 50°C to about 250°C. The isomerization process is typically conducted in an inert atmosphere e.g., under nitrogen or in the presence of other gases such as hydrogen at any manageable pressure.
For the sake of clarity, the term “comprising” as used in this application is defined as “specifying the presence of stated features, integers, steps, or components as recited, but not precluding the presence or addition of one or more other steps, components, or groups thereof’. Comprising is different from “consisting of” which does preclude the presence or addition of one or more other steps, components, or groups thereof.
The alpha olefins to be converted to intemal olefin are C, to C,, straight or branched-chain monoolefinically unsaturated hydrocarbons in which the olefinic unsaturation occurs at the 1- or alpha-position of the carbon chain. Typically these compounds have the following formula
R?
R'-CH,-CH,-(CH,),,-C=CH, where R' and R? are the same or different and are hydrogen or alkyl, i.e., C, to Cy, linear or branched alkyl, preferably C, to C,, linear or branched alkyl, most preferably
C, to GC; linear or branched alkyl, e.g. methyl, ethy! and the like, and m is an integer from 0 to 26. Particularly preferred are compounds where R' is alkyl and R? is hydrogen.
Such alpha-olefins are commercially available and can be made by ithe thermal cracking of paraffinic hydrocarbons, by conversion of the corresponding alcohol to an olefin or by the well-known Ziegler ethylene chain growth and displacement from trialkylaluminum compounds. Individual olefins may be used as well as mixtures of such olefins. Examples of such olefins are 1-hexene, 1-heptene, 1-octene, 1-nonene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1- octadecene, 1-eicocene, and the like. The more preferred normal-alpha-olefins are ) those containing about 6-30 carbon atoms. The most preferred normal-alpha-olefins are those containing about 10-30 carbon atoms. Some internal alpha olefins may also be present in the reaction mixture at the start of the reaction. Obviously, the amount of internal olefin present in the reaction mixture will increase at the conversion of alpha olefins to internal olefins proceeds in accord with the process of this invention.
After conversion the internal olefins are useful, e.g., when oligomerized, as oils. . Depending on their viscosity, different applications for such oils are known, e.g., as lubricants. These materiais are generally mixtures of different percentages of dimer, trimer, tetramer, pentamer and higher oligomers which oligomers are produced in different proportions in an oligomerization process. In order to increase the viscosity, processes are used which either produce more of the higher oligomers or, alternatively, some of the lower oligomers are removed typically by distillation. Most low viscosity dimer and trimer products are obtained as by-products of the production of higher viscosity synthetic oils. Due to the increasing use of dimers in applications such as low temperature lubricants and drilling fluids, methods for their preferential production from the isomerized alpha olefins are of interest.
Vinylidenes or vinylidene olefins may be represented by the formula
R3 aa r4 and “trisubstituted olefins” may be represented by the formula
RA
ARN
R4 H wherein R®, R*, and R® represent hydrocarbon groups. Reaction 1 above shows the isomerization of a vinylidene olefin to a trisubstituted olefin. Typically, the isomerization of a vinylidene olefin to a trisubstituted olefin occurs with greater facility . 25 than the internal isomerization of an alpha olefin to an internal olefin when both are present. Upon oligomerization of such an isomerization mixture, the oligomerization products of trisubstituted species will be present together with the oligomerization products of internal olefins in the oligomer oils produced. In commercial production, it may be difficult to obtain an oligomer product mix which, when fractionated, will produce the relative amounts of each viscosity product which correspond to market demand. Thus, the ability to selectively isomerize only the aipha olefin may offer a significant commercial advantage. 5 In this application, Applicants disclose a process which selectively isomerizes alpha olefins to internal olefins in a reaction mixture which also contains vinylidene olefins and without substantial isomerization of the vinylidene olefins to trisubstituted olefins. For the purpose of this invention, without substantial isomerization of the vinylidene is intended to denote that the conversion achieved in the desired reaction is at least five times as great as the conversion of vinylidene olefins to trisubstituted olefins. For example in a feed containing both alpha olefins and vinylidene olefins where 5 % (mole or weight %) of the vinylidene olefins were converted to trisubstituted olefins by the method of this invention, a conversion of alpha olefins to internal olefins exceeding 25 % (mole or weight %) would be considered to have met the condition without substantial isomerization of the vinylidene olefin to trisubstituted olefin.
The process utilizes a metal-based homogeneous or heterogeneous catalyst.
The catalysts used in the process are ruthenium trihalides including ruthenium trihalide hydrates. The preferred catalysts are ruthenium trichloride and ruthenium tribromide including the various hydrated forms of either. The ruthenium trihalide (RuX,) catalysts of this invention are preferably employed in homogeneous form, dissolved in neat liquid olefin or a mixture of olefin and a solvent. Alcohols are effective solvents for the RuX; compounds of this invention.
The selective alpha-olefin isomerization process of this invention using RuX, compounds may be conducted at temperatures in the range of about 50°C to about 250°C, but preferably in the range of about 100°C to about 200°C. The isomerization
N process is typically conducted in an inert atmosphere e.g., under nitrogen or in the presence of other gases such as hydrogen. The process is typically conducted at atmospheric pressure (about 1.0 bars) but may be conducted at any manageable pressure typically in the range of about 0.1 to about 25 bars, and preferably in the range of about 0.5 bars to about 5.0 bars.
To a glass reaction vessel was added 100 ml of an olefin mixture containing alpha, internal, vinylidene, and trisubstituted olefins of even carbon numbers from 18 through 30. To this was added 0.5 ml of a 0.0024 molar solution of ruthenium ) 5 trichloride hydrate in hexanol, corresponding to a charge of about 1.2 ppm Ru in the reaction solution. The solution was vigorously stirred at room temperature and a small sample of the liquid was removed for analysis and designated as the “Before
Reaction Sample”. The reaction vessel was then immersed in an oil bath which had been pre-heated to 170°C. The reaction vessel was maintained at 170°C while a flow of hydrogen gas at atmospheric pressure was sparged through the reaction solution at 0.1 SCFH. Afterward, another liquid sample was removed (4Hour Reaction
Sample) from the vessel. The two samples were analyzed by NMR to determine the types of olefins present. The results obtained are as shown in Table 1 below.
Table 1
Olefin Mole % Olefin Type in Mole % Olefin Type in 16
These results clearly indicate that isomerization of alpha-olefins to internal olefins predominated over isomerization of vinylidene olefins to trisubstituted species.
Comparative Example
The data for the following comparative example was taken from US Patent No. 4,724,274. Table 2 below shows the feed composition prior to isomerization and the product mixture after isomerization. The feed was passed over a fixed bed catalyst consisting of 0.3 weight percent palladium deposited on gamma alumina. Sulfur (in the form of dimethyl! sulfide) was added to the feed so as to be present at a level of 6
PPM. The reaction was conducted in the presence of hydrogen at a pressure of 25 bars and a temperature of 80° C.
Table ‘ Species Weight % in Feed Weight % 1-pentene 25 emo
ELL I EN
2-methyl-1butene 40 7.2 : eam 2-methyl-2-butene 32.7
Cs ene | ww
EC I EL
From this comparative example it is observed that 82 % of the vinylidene olefin present in the feed was converted to trisubstituted olefin while none of the alpha olefin present in the feed was converted to internal olefin. In fact, the alpha olefin was destroyed (hydrogenated to pentane). These results are in stark contrast to the working example of this invention where alpha olefin was selectively isomerized to internal olefin without substantial isomerization of the vinylidene olefin to trisubstitued olefin.
Claims (10)
1. A process for the selective isomerization of alpha olefins to internal olefins . comprising the use of ruthenium trihalide catalyst wherein vinylidene olefin is also present in the reaction mixture and wherein the selective isomerization of the alpha olefins to internal olefins occurs without significant concurrent isomerization of the vinylidine olefin also present in the reaction mixture.
2. The process of claim 1 wherein the alpha olefin has the formula R? R'-CH,-CH,~(CH,),-C=CH, where R' and R? are independently selected from the group consisting of hydrogen, ] C, to Cy, straight alkyl, and C, to C,, branched alkyl and wherein m is an integer in the range of 0-26.
3. The process of claim 2 where R' and R? are independently selected from the group consisting of hydrogen, C, to C,, straight alkyl, and C, to C,, branched alkyl.
4. The process of claim 2 where R' and R? are independently selected from the group consisting of hydrogen, C, to C, straight alkyl, and C, to C; branched alkyl.
5. The process of claim 2 where R'is C, to C,, straight or branched alkyl and R?is hydrogen.
6. The process of claim 1 wherein the ruthenium trihalide is selected from the group consisting of ruthenium trichloride, ruthenium trichloride hydrate; ruthenium tribromide, ruthenium tribromide hydrate, and mixtures of the preceding.
7. The process of claim 1 wherein the selective isomerization is conducted at a temperature in the range of about 50°C to about 250°C.
8. The process of claim 1 wherein the selective isomerization is conducted at a * temperature in the range of about 100°C to about 200°C.
9. The process of claim 1 wherein the selective isomerization is conducted at a pressure in the range of about 0.1 bars to about 25 bars.
10. The process of claim 1 wherein the selective isomerization is conducted at a pressure in the range of about 0.5 bars to about 5.0 bars. a
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56439700A | 2000-05-01 | 2000-05-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200208320B true ZA200208320B (en) | 2003-07-22 |
Family
ID=24254302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200208320A ZA200208320B (en) | 2000-05-01 | 2002-10-15 | Process for the selective isomerization of alpha-olefins in the presence of vinylidene olefins. |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1278713A1 (en) |
| JP (1) | JP2004518610A (en) |
| AU (1) | AU2001261082A1 (en) |
| CA (1) | CA2435834A1 (en) |
| CZ (1) | CZ20023580A3 (en) |
| NO (1) | NO20025260D0 (en) |
| RU (1) | RU2002129580A (en) |
| WO (1) | WO2001083409A1 (en) |
| ZA (1) | ZA200208320B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040249229A1 (en) | 2003-06-06 | 2004-12-09 | Gee Jeffery C. | Isomerization of olefins with carboxylic acid |
| WO2014112522A1 (en) * | 2013-01-15 | 2014-07-24 | 花王株式会社 | Method for producing internal olefin |
| ES2929364B2 (en) * | 2021-05-28 | 2024-03-18 | Consejo Superior Investigacion | PROCEDURE FOR OBTAINING LONG CHAIN LINEAR ALKENES |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1002913A (en) * | 1962-08-22 | 1965-09-02 | British Petroleum Co | Process for the production of olefins |
| GB1116943A (en) * | 1964-08-21 | 1968-06-12 | Johnson Matthey Co Ltd | Improvements in and relating to catalytic reactions and a catalyst for use therein |
-
2001
- 2001-04-26 CZ CZ20023580A patent/CZ20023580A3/en unknown
- 2001-04-26 EP EP01934940A patent/EP1278713A1/en not_active Withdrawn
- 2001-04-26 AU AU2001261082A patent/AU2001261082A1/en not_active Abandoned
- 2001-04-26 JP JP2001580844A patent/JP2004518610A/en active Pending
- 2001-04-26 RU RU2002129580/04A patent/RU2002129580A/en unknown
- 2001-04-26 CA CA002435834A patent/CA2435834A1/en not_active Abandoned
- 2001-04-26 WO PCT/US2001/013838 patent/WO2001083409A1/en not_active Application Discontinuation
-
2002
- 2002-10-15 ZA ZA200208320A patent/ZA200208320B/en unknown
- 2002-11-01 NO NO20025260A patent/NO20025260D0/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1278713A1 (en) | 2003-01-29 |
| WO2001083409A1 (en) | 2001-11-08 |
| AU2001261082A1 (en) | 2001-11-12 |
| RU2002129580A (en) | 2004-02-27 |
| CZ20023580A3 (en) | 2003-04-16 |
| NO20025260L (en) | 2002-11-01 |
| NO20025260D0 (en) | 2002-11-01 |
| CA2435834A1 (en) | 2001-11-08 |
| JP2004518610A (en) | 2004-06-24 |
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