CA1212965A - Co-oligomerization of olefins - Google Patents
Co-oligomerization of olefinsInfo
- Publication number
- CA1212965A CA1212965A CA000450028A CA450028A CA1212965A CA 1212965 A CA1212965 A CA 1212965A CA 000450028 A CA000450028 A CA 000450028A CA 450028 A CA450028 A CA 450028A CA 1212965 A CA1212965 A CA 1212965A
- Authority
- CA
- Canada
- Prior art keywords
- olefins
- psig
- branched
- reaction zone
- chain
- Prior art date
- 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
Links
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 26
- 238000006384 oligomerization reaction Methods 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 9
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052796 boron Inorganic materials 0.000 claims abstract description 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 7
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 14
- 229910015900 BF3 Inorganic materials 0.000 description 7
- 239000000203 mixture Substances 0.000 description 5
- 239000004711 α-olefin Substances 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- -1 aluminum alkyl halide Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N methyl heptene Natural products CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 230000003606 oligomerizing effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
Preparation of C20-C40 branched-chain olefins by the co-oligomerization of C12-C18 branched-chain internal olefins with C5-C6 olefins by a process comprising (a) contacting a propylene oligomer feedstock having from 12 to 18 carbon atoms with a C5-C6 olefin feedstock in a reaction zone in the presence of a boron trifluoride-alkanol catalyst; (b) maintaining the temperature in the reaction zone between about 0°C and 80°C; and (c) main-taining the pressure in the reaction zone between about 0 psig and 200 psig.
Preparation of C20-C40 branched-chain olefins by the co-oligomerization of C12-C18 branched-chain internal olefins with C5-C6 olefins by a process comprising (a) contacting a propylene oligomer feedstock having from 12 to 18 carbon atoms with a C5-C6 olefin feedstock in a reaction zone in the presence of a boron trifluoride-alkanol catalyst; (b) maintaining the temperature in the reaction zone between about 0°C and 80°C; and (c) main-taining the pressure in the reaction zone between about 0 psig and 200 psig.
Description
CO-O~IGOMERIZATION OF OLEFINS
The present invention relates to a process for the preparation of C20-C40 branched-chain olefins by the co-oli~omerization of C12-Cl~ branched-chain internal olefins with C5-C6 olefins in the presence of a boron trifluoride-alkanol catalyst.
The oligomerization of alpha olefins is well known in the art. Thus, U.S. Patent No. 3,932,553 describes the oligomerization of propylene in the presence of a boron trifluoride catalyst and a small amount of an olefinic diene to provide oli~omers having about 15 to 21 carbon atoms.
U.S. Patent No. 4,024,203 Aescribes the oligo-merization of lower molecular weight mono alpha olefins utilizing a catalyst composition containing a Bronsted acid, a sulfone, an~ optionally, a Lewis acid, to provide predominantly dimers and trimers.
U.S. Patent No. 4,041,098 describes a method of oligomerizing straight-chain alpha olefins having from 3 to 14 carbon atoms with a soluble catalyst system consist-ing of an aluminum alkyl halide and an organo halide.
U.S. Patent Nos. 4,045,507 and 4,045,508describe the oligomerization of alpha olefins having about 5 to 14 carbon atoms, particularly l-decene and mixtures of l-decene with l-octene and/or l-dodecene, in the presence of a boron trifluoride catalyst and a co-catalyst that complexes with boron trifluoride to provide an oligomer mixture including trimer and tetramer.
5UMMARY OF TH~ INVENTION
It has now been found that the production of C20-C40 branched-chain olefins is successfully achieved by the co-oligomerization of C12-C18 branched-chain internal olefins with C5-C6 olefins by a process which comprises (a) contacting a propylene oligomer feedstock having from 12 to 18 carbon atoms with a C5-C6 olein feedstock in a reaction zone in the presence of a boron trifluoride-alkanol catalyst; (b) maintainin~ the temperature in the 05 reaction zone between about 0C and 80C; and (c) main-taining the pressure in the reaction zone between about 0 psig and 200 psig.
Among other factors, the present invention is based on the discovery that C12-C18 internal olefins which are also highly branched can be co-oligomerized with C5-C6 olefins to provide high molecular weight branched-chain olefins in high yield and conversions.
The process of the present invention is suitable for the production of C20-C40 branched-chain olefins.
The olefins thus prepared are highly branched compounds and the term ~Ibranched-chain~ is herein used to si~nify at least one carbon branch per every 5 carbon atoms in the olefin product.
A propylene oligomer feedstock having from 12 to 1~ carbon atoms and an internal double bond is used as a starting material. This feedstock may be obtained by the direct oligomeriæation o~ propylene in an acid medium.
The propylene oligomer feedstock is contacted with a C5-C6 olefin feedstock in the presence of a boron trifluoride-alkanol catalyst~ The C5-C6 olefin may be obtained as a product of naphtha cracking and normally will contain a mixture of both straight-chain and branched-chain olefins. The reaction is carried out at a temperature of about 0C to about 8QC, preferably from about 10C to about 60C. The reaction pressure is maintained at about 0 psig to about 200 psig, preferably from about 0 psig to about 150 psig.
The use of boron trifluoride-alkanol as the co-oligomerization catalyst has been found to be satis-factory for providing the olefin product in hi~h yield.
The boron trifluoride catalyst is pre~erablyutilized in combination with an alkanol~ Suitable alkanols include straight~chain alkanols of 1 to 8 carbon atoms. A preferred alkanol is normal butanol. ~enerally, about 0.01 to 1, and preferably ahout O.OS to 0.5, moles of boron trifluoride are utilized per mole of olefin feedstock. The boron trifluoride-alkanol catalyzed reac-os tion proceeds to give over ~0% conversion to the oleinproduct.
The co-oligomerized branched-chain olefinic products may be separated from the reaction mixture by conventional procedures, such as fractional distillationO
The C~0-C40 branched-chain olefins prepared by the process of the present invention are useful as precursors for surface-active products, lubricating compo-sitions, and the like.
The following example is provided to illustrate the invention in accordance with the principles of the invention but is not to be construed as limiting the invention in any way except as indicated by the appended claims.
EXAMPLE
Exam~le 1 A 2 liter, 3-necked, round-bottom flask was equipped with a boron trifluoride bubbler, stirrer, dropping funnel, thermometer and condenser with ice trap and drierite tube. To this flask, 660 ml ~2.6 moles) of a propylene polymer having an average molecular weight of about 200 and 960 ml (12.5 moles) of C5~C6 distilled FCC
light gasoline was added and saturated with boron tri-fluoride. ~ith stirring, 120 ml ~1.6 moles) of n butanol was added over a period of 180 minutes, while maintaining a temperature of 40C. The reaction was run for 6 hours and the results are shown in Table 1.
Table 1 35Time, hours Olefin Conversion __
The present invention relates to a process for the preparation of C20-C40 branched-chain olefins by the co-oli~omerization of C12-Cl~ branched-chain internal olefins with C5-C6 olefins in the presence of a boron trifluoride-alkanol catalyst.
The oligomerization of alpha olefins is well known in the art. Thus, U.S. Patent No. 3,932,553 describes the oligomerization of propylene in the presence of a boron trifluoride catalyst and a small amount of an olefinic diene to provide oli~omers having about 15 to 21 carbon atoms.
U.S. Patent No. 4,024,203 Aescribes the oligo-merization of lower molecular weight mono alpha olefins utilizing a catalyst composition containing a Bronsted acid, a sulfone, an~ optionally, a Lewis acid, to provide predominantly dimers and trimers.
U.S. Patent No. 4,041,098 describes a method of oligomerizing straight-chain alpha olefins having from 3 to 14 carbon atoms with a soluble catalyst system consist-ing of an aluminum alkyl halide and an organo halide.
U.S. Patent Nos. 4,045,507 and 4,045,508describe the oligomerization of alpha olefins having about 5 to 14 carbon atoms, particularly l-decene and mixtures of l-decene with l-octene and/or l-dodecene, in the presence of a boron trifluoride catalyst and a co-catalyst that complexes with boron trifluoride to provide an oligomer mixture including trimer and tetramer.
5UMMARY OF TH~ INVENTION
It has now been found that the production of C20-C40 branched-chain olefins is successfully achieved by the co-oligomerization of C12-C18 branched-chain internal olefins with C5-C6 olefins by a process which comprises (a) contacting a propylene oligomer feedstock having from 12 to 18 carbon atoms with a C5-C6 olein feedstock in a reaction zone in the presence of a boron trifluoride-alkanol catalyst; (b) maintainin~ the temperature in the 05 reaction zone between about 0C and 80C; and (c) main-taining the pressure in the reaction zone between about 0 psig and 200 psig.
Among other factors, the present invention is based on the discovery that C12-C18 internal olefins which are also highly branched can be co-oligomerized with C5-C6 olefins to provide high molecular weight branched-chain olefins in high yield and conversions.
The process of the present invention is suitable for the production of C20-C40 branched-chain olefins.
The olefins thus prepared are highly branched compounds and the term ~Ibranched-chain~ is herein used to si~nify at least one carbon branch per every 5 carbon atoms in the olefin product.
A propylene oligomer feedstock having from 12 to 1~ carbon atoms and an internal double bond is used as a starting material. This feedstock may be obtained by the direct oligomeriæation o~ propylene in an acid medium.
The propylene oligomer feedstock is contacted with a C5-C6 olefin feedstock in the presence of a boron trifluoride-alkanol catalyst~ The C5-C6 olefin may be obtained as a product of naphtha cracking and normally will contain a mixture of both straight-chain and branched-chain olefins. The reaction is carried out at a temperature of about 0C to about 8QC, preferably from about 10C to about 60C. The reaction pressure is maintained at about 0 psig to about 200 psig, preferably from about 0 psig to about 150 psig.
The use of boron trifluoride-alkanol as the co-oligomerization catalyst has been found to be satis-factory for providing the olefin product in hi~h yield.
The boron trifluoride catalyst is pre~erablyutilized in combination with an alkanol~ Suitable alkanols include straight~chain alkanols of 1 to 8 carbon atoms. A preferred alkanol is normal butanol. ~enerally, about 0.01 to 1, and preferably ahout O.OS to 0.5, moles of boron trifluoride are utilized per mole of olefin feedstock. The boron trifluoride-alkanol catalyzed reac-os tion proceeds to give over ~0% conversion to the oleinproduct.
The co-oligomerized branched-chain olefinic products may be separated from the reaction mixture by conventional procedures, such as fractional distillationO
The C~0-C40 branched-chain olefins prepared by the process of the present invention are useful as precursors for surface-active products, lubricating compo-sitions, and the like.
The following example is provided to illustrate the invention in accordance with the principles of the invention but is not to be construed as limiting the invention in any way except as indicated by the appended claims.
EXAMPLE
Exam~le 1 A 2 liter, 3-necked, round-bottom flask was equipped with a boron trifluoride bubbler, stirrer, dropping funnel, thermometer and condenser with ice trap and drierite tube. To this flask, 660 ml ~2.6 moles) of a propylene polymer having an average molecular weight of about 200 and 960 ml (12.5 moles) of C5~C6 distilled FCC
light gasoline was added and saturated with boron tri-fluoride. ~ith stirring, 120 ml ~1.6 moles) of n butanol was added over a period of 180 minutes, while maintaining a temperature of 40C. The reaction was run for 6 hours and the results are shown in Table 1.
Table 1 35Time, hours Olefin Conversion __
2 4%
3 25%
4 31%
3~%
6 44%
3~%
6 44%
Claims (5)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A process for the preparation of C20-C40 branched-chain olefins by the co-oligomerization of C12-C18 branched-chain internal olefins with C5-C6 olefins which comprises:
(a) contacting a propylene oligomer feedstock having from 12 to 18 carbon atoms with a C5-C6 olefin feedstock in a reaction zone in the presence of a boron trifluoride-alkanol catalyst;
(b) maintaining the temperature in the reaction zone between about 0°C and 80°C; and (c) maintaining the pressure in the reaction zone between about 0 psig and 200 psig.
(a) contacting a propylene oligomer feedstock having from 12 to 18 carbon atoms with a C5-C6 olefin feedstock in a reaction zone in the presence of a boron trifluoride-alkanol catalyst;
(b) maintaining the temperature in the reaction zone between about 0°C and 80°C; and (c) maintaining the pressure in the reaction zone between about 0 psig and 200 psig.
2. A process according to Claim 1, wherein the alkanol is normal butanol.
3. A process according to Claim 1, wherein the reaction is carried out at a temperature between about 10°C and 60°C.
4. A process according to Claim 1, wherein the reaction is carried out at a pressure between about 0 psig and 150 psig.
5. A process according to Claim 1, wherein the reaction zone reaction conditions are maintained suffi-cient to yield at least 40% conversion of the olefin feedstock to the C20-C40 branched-chain olefins, including a temperature between about 0°C and 80°C, and a pressure between about 0 psig and 200 psig.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000450028A CA1212965A (en) | 1984-03-20 | 1984-03-20 | Co-oligomerization of olefins |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000450028A CA1212965A (en) | 1984-03-20 | 1984-03-20 | Co-oligomerization of olefins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1212965A true CA1212965A (en) | 1986-10-21 |
Family
ID=4127453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000450028A Expired CA1212965A (en) | 1984-03-20 | 1984-03-20 | Co-oligomerization of olefins |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1212965A (en) |
-
1984
- 1984-03-20 CA CA000450028A patent/CA1212965A/en not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |