US2537283A - Isomerization of olefins - Google Patents
Isomerization of olefins Download PDFInfo
- Publication number
- US2537283A US2537283A US51843A US5184348A US2537283A US 2537283 A US2537283 A US 2537283A US 51843 A US51843 A US 51843A US 5184348 A US5184348 A US 5184348A US 2537283 A US2537283 A US 2537283A
- Authority
- US
- United States
- Prior art keywords
- isomerization
- olefins
- olefinic
- ammonium phosphate
- isomerizing
- 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 - Lifetime
Links
- 150000001336 alkenes Chemical class 0.000 title description 15
- 238000006317 isomerization reaction Methods 0.000 title description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 8
- 239000004254 Ammonium phosphate Substances 0.000 claims description 7
- 229910000148 ammonium phosphate Inorganic materials 0.000 claims description 7
- 235000019289 ammonium phosphates Nutrition 0.000 claims description 7
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 150000001925 cycloalkenes Chemical class 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229910000286 fullers earth Inorganic materials 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide 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
- 238000006276 transfer reaction Methods 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
- C07C5/2537—Acids of phosphorus; Salts thereof; Phosphorus oxides
-
- 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
- C07C5/2206—Catalytic processes not covered by C07C5/23 - C07C5/31
- C07C5/2226—Catalytic processes not covered by C07C5/23 - C07C5/31 with inorganic acids; with salt or anhydrides of acids
- C07C5/224—Acids of phosphorus; Salts thereof; Phosphorus oxides
-
- 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
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/2767—Changing the number of side-chains
- C07C5/277—Catalytic processes
- C07C5/2778—Catalytic processes with inorganic acids; with salts or anhydrides of acids
- C07C5/2783—Acids of phosphorus; Salts thereof; Phosphorus oxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- C07C2521/08—Silica
-
- 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
- C07C2527/14—Phosphorus; Compounds thereof
- C07C2527/16—Phosphorus; Compounds thereof containing oxygen
- C07C2527/167—Phosphates or other compounds comprising the anion (PnO3n+1)(n+2)-
Definitions
- This invention relates to a process for isomerizing olefinic hydrocarbons and particularly for isomerizing alkenes.
- An object, of this invention is to isomerize an olefinic hydrocarbon.
- Another object of this invention is to isomerize an alkene having at least four carbon atoms per molecule.
- this invention relates to a process for isomerizing olefinic hydrocarbons which comprises contacting an olefinic hydrocarbon having at least four carbon atoms per molecule at conversion conditions withan amprocess have at least four carbon atoms per molecule and include butylenes'pentenes, and higher molecular weight normally liquid olefins, the latter including various polymers of normally gaseous olefins.
- Cycloolefins such as cyclopentene, cyclohexene, and various cycloolefins may also be used but not necessarily under the same conditions of operation as employed with open chain olefins which may also be referred to as alkenes.
- Catalysts useful in promoting an isomerization of olefinic hydrocarbons comprise ammonium salts of phosphoric acids.
- These ammonium salts include both neutral and acid salts of ortho-, pyro-, tri-, tetra-, and other polyphos phoric acids, as such, in admixture with one another and also supported on solid carriers, such as a siliceous carrier as silica, diatomaceous earth, fullers earth, crushed porcelain, etc., and also alumina, charcoal, and other packing materials Which do not interfere with the desired catalytic activity of an ammonium phosphate.
- Composites of an ammonium salt of an acid of phosphorus and a carrier, such as diatomaceous earth or some other siliceous material, are preferably calcined before being utilized as catalysts in conversion reactions of organic compounds and particularly of hydrocarbons. Such calcination is generally carried out at a temperature of about 200 to about 500 C.
- an olefinic hydrocarbon may be-reacted in the presence of an ammonium phosphate catalyst at a temperature of from about C. to about 450 C. to produce isomeric olefins including branched chain and straight chain olefins.
- the isomerization of a straight chain olefinic in the presence of an ammonium phosphate yields a branched chain olefin as a result of so-called, skeletal isomerization of the charged olefinic .hy-
- the process of the present invention is carried out in either batch or continuous types of operation.
- the olefin containing at least four carbon atoms per molecule is brought to a reaction temperature as specified above in the presence of an ammonium phosphate or of a solid composite of an ammonium phosphate and a suitable carrier 'or supporting material while the reaction mixture is stirred mechanically to eiiect intimate contact between the catalyst and the olefinic 56, hydrocarbon charging stock.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Jan. 9, 1951 UNITED" STATES PATENT OFFICE,
2,537,283 ISOMERIZATION or OLEFINS Raymond E. Schaad, Riverside, Ill., assignor to Universal Oil Products Company, Chicago, 111., a corporation of Delaware No Drawing. Application September 29, 1948, Serial No. 51,843
I Claims.
This application is a continuation-in-part of my co-pending application Serial Number 706,057 filed October 2-3, 1946.
This invention relates to a process for isomerizing olefinic hydrocarbons and particularly for isomerizing alkenes.
An object, of this invention is to isomerize an olefinic hydrocarbon.
Another object of this invention is to isomerize an alkene having at least four carbon atoms per molecule.
In one embodiment, this inventionrelates to a process for isomerizing olefinic hydrocarbons which comprises contacting an olefinic hydrocarbon having at least four carbon atoms per molecule at conversion conditions withan amprocess have at least four carbon atoms per molecule and include butylenes'pentenes, and higher molecular weight normally liquid olefins, the latter including various polymers of normally gaseous olefins. Cycloolefins such as cyclopentene, cyclohexene, and various cycloolefins may also be used but not necessarily under the same conditions of operation as employed with open chain olefins which may also be referred to as alkenes.
Catalysts useful in promoting an isomerization of olefinic hydrocarbons comprise ammonium salts of phosphoric acids. These ammonium salts include both neutral and acid salts of ortho-, pyro-, tri-, tetra-, and other polyphos phoric acids, as such, in admixture with one another and also supported on solid carriers, such as a siliceous carrier as silica, diatomaceous earth, fullers earth, crushed porcelain, etc., and also alumina, charcoal, and other packing materials Which do not interfere with the desired catalytic activity of an ammonium phosphate. Composites of an ammonium salt of an acid of phosphorus and a carrier, such as diatomaceous earth or some other siliceous material, are preferably calcined before being utilized as catalysts in conversion reactions of organic compounds and particularly of hydrocarbons. Such calcination is generally carried out at a temperature of about 200 to about 500 C.
According to the process of the present inven--' tion, an olefinic hydrocarbon may be-reacted in the presence of an ammonium phosphate catalyst at a temperature of from about C. to about 450 C. to produce isomeric olefins including branched chain and straight chain olefins. The isomerization of a straight chain olefinic in the presence of an ammonium phosphate yields a branched chain olefin as a result of so-called, skeletal isomerization of the charged olefinic .hy-
,drocarbons. The isomerization reaction .may
also involve the shifting of the position of the double bond along the carbon chain of the olefinic hydrocarbon. Thus a shift of the doublebond occurs when l-butylene is converted into 2- butylene whereas skeletal isomerization occurs;
during the conversion of either of the straight chain olefins, l-butylene and Z-butylene, into the branched chain olefin isobutylene, this being an example of the so-called skeletal isomerization- Olefin isomerization in the presence of acatalyst comprising an ammonium phosphate as its essential active ingredient, is carried out preferably at a temperature of from about 150 to about 350 0., particularly since the higher tem-- perature of the broader range, namely, from about 150 to about 450 C., sometimes result in certain amountsof decomposition, cracking, and.
hydrogen transfer reactions. The process is also carried out generally at atmospheric pressure,
although higher conversions may sometimes be obtained at subatmospheric pressure while increased capacity results when the process is effected at a slight superatmospheric pressure which is generally not more than about 5 atmospheres. At a superatmospheric pressure; a certain amount of olefin polymerization takes place with the result that the yield of isomerized olefin is decreased.
The process of the present invention is carried out in either batch or continuous types of operation. Thus in a simple batch type process, the olefin containing at least four carbon atoms per molecule is brought to a reaction temperature as specified above in the presence of an ammonium phosphate or of a solid composite of an ammonium phosphate and a suitable carrier 'or supporting material while the reaction mixture is stirred mechanically to eiiect intimate contact between the catalyst and the olefinic 56, hydrocarbon charging stock.
Claims (1)
1. A PROCESS FOR ISOMERIZING OLEFINIC HYDROCARBONS WHICH COMPRISES CONTACTING AN OLEFINIC HYDROCARBON HAVING AT LEAST FOUR CARBON ATOMS PER MOLECULE AT ISOMERIZING CONDITIONS WITH AN AMMONIUM PHOSPHATE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51843A US2537283A (en) | 1948-09-29 | 1948-09-29 | Isomerization of olefins |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51843A US2537283A (en) | 1948-09-29 | 1948-09-29 | Isomerization of olefins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2537283A true US2537283A (en) | 1951-01-09 |
Family
ID=21973706
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US51843A Expired - Lifetime US2537283A (en) | 1948-09-29 | 1948-09-29 | Isomerization of olefins |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2537283A (en) |
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3448164A (en) * | 1967-09-21 | 1969-06-03 | Phillips Petroleum Co | Olefin skeletal isomerization and catalyst |
| US5132484A (en) * | 1989-11-29 | 1992-07-21 | Uop | Butene isomerization process |
| US5146035A (en) * | 1989-11-29 | 1992-09-08 | Uop | Butene isomerization process |
| US5191146A (en) * | 1989-11-29 | 1993-03-02 | Uop | Olefin isomerization process |
| US5292984A (en) * | 1989-11-29 | 1994-03-08 | Uop | Pentene isomerization and etherification |
| US5336831A (en) * | 1989-11-29 | 1994-08-02 | Uop | Olefin isomerization process |
| US5367101A (en) * | 1989-11-29 | 1994-11-22 | Uop | Pentene isomerization process |
| US5463161A (en) * | 1989-11-29 | 1995-10-31 | Uop | Olefin isomerization process |
| US5801293A (en) * | 1996-02-26 | 1998-09-01 | Chevron U.S.A. Inc. | Method of isomerizing olefins |
| US6156947A (en) * | 1998-06-22 | 2000-12-05 | Uop Llc | Process for the production of butene-1 from a mixture of C4 olefins |
| US20030233018A1 (en) * | 2002-06-18 | 2003-12-18 | Brown Stephen H. | Method for isomerizing a mixed olefin feedstock to 1-olefin |
| US20080146858A1 (en) * | 2006-12-14 | 2008-06-19 | Chevron U.S.A. Inc. | Isomerization of butene in the ionic liquid-catalyzed alkylation of light isoparaffins and olefins |
| US7531707B2 (en) | 2006-12-13 | 2009-05-12 | Chevron U.S.A., Inc | Alkylation process using an alkyl halide promoted ionic liquid catalyst |
| US20090159837A1 (en) * | 2007-12-21 | 2009-06-25 | Chevron U.S.A., Inc. | Refrigeration oil from gas-to-liquid-derived and bio-derived diesters |
| US20090159835A1 (en) * | 2007-12-21 | 2009-06-25 | Chevron U.S.A., Inc. | Refrigeration oil from gas-to-liquid-derived and bio-derived triesters |
| US20090198075A1 (en) * | 2008-01-31 | 2009-08-06 | Chevron U.S.A. Inc. | Synthesis of diester-based biolubricants from epoxides |
| US20100120642A1 (en) * | 2008-11-13 | 2010-05-13 | Chevron U.S.A. Inc. | Synthesis of diester-based lubricants from enzymatically-directed epoxides |
| US20110053817A1 (en) * | 2007-02-12 | 2011-03-03 | Chevron U.S.A. Inc. | Multi-grade engine oil formulations comprising a bio-derived ester component |
| US8410033B2 (en) | 2010-08-26 | 2013-04-02 | Chevron U.S.A. Inc. | Preparation of diester-based biolubricants from monoesters of fatty acids and olefin-derived vicinal diols |
| DE112011102541T5 (en) | 2010-07-29 | 2013-05-02 | Chevron U.S.A. Inc. | APPLICATION-SPECIFIC MANUFACTURED LUBRICANT COMPOSITIONS COMPRISING A BIOLOGICAL ESTER COMPONENT, AND METHOD FOR MANUFACTURING THE SAME |
| DE112011104579T5 (en) | 2010-12-23 | 2013-09-26 | Chevron U.S.A. Inc. | High flash point esters as electrical insulating oils |
| EP2671863A1 (en) | 2007-02-12 | 2013-12-11 | Chevron U.S.A. Inc. | Method of making diester-based lubricants |
| WO2019183187A1 (en) | 2018-03-20 | 2019-09-26 | Basf Se | Lubricant composition |
| EP3712235A1 (en) | 2019-03-20 | 2020-09-23 | Basf Se | Lubricant composition |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1841055A (en) * | 1927-12-02 | 1932-01-12 | Ig Farbenindustrie Ag | Production of unsaturated hydrocarbons |
| US1939647A (en) * | 1930-07-23 | 1933-12-19 | Du Pont | Method of impregnating porous materials |
| US2357741A (en) * | 1940-10-28 | 1944-09-05 | Anglo Iranian Oil Co Ltd | Production of gasolines |
| US2421229A (en) * | 1942-09-11 | 1947-05-27 | Universal Oil Prod Co | Process for the separation of isobutene from a mixture of c hydrocarbons |
-
1948
- 1948-09-29 US US51843A patent/US2537283A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1841055A (en) * | 1927-12-02 | 1932-01-12 | Ig Farbenindustrie Ag | Production of unsaturated hydrocarbons |
| US1939647A (en) * | 1930-07-23 | 1933-12-19 | Du Pont | Method of impregnating porous materials |
| US2357741A (en) * | 1940-10-28 | 1944-09-05 | Anglo Iranian Oil Co Ltd | Production of gasolines |
| US2421229A (en) * | 1942-09-11 | 1947-05-27 | Universal Oil Prod Co | Process for the separation of isobutene from a mixture of c hydrocarbons |
Cited By (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3448164A (en) * | 1967-09-21 | 1969-06-03 | Phillips Petroleum Co | Olefin skeletal isomerization and catalyst |
| US5132484A (en) * | 1989-11-29 | 1992-07-21 | Uop | Butene isomerization process |
| US5146035A (en) * | 1989-11-29 | 1992-09-08 | Uop | Butene isomerization process |
| US5191146A (en) * | 1989-11-29 | 1993-03-02 | Uop | Olefin isomerization process |
| US5292984A (en) * | 1989-11-29 | 1994-03-08 | Uop | Pentene isomerization and etherification |
| US5336831A (en) * | 1989-11-29 | 1994-08-02 | Uop | Olefin isomerization process |
| US5367101A (en) * | 1989-11-29 | 1994-11-22 | Uop | Pentene isomerization process |
| US5463161A (en) * | 1989-11-29 | 1995-10-31 | Uop | Olefin isomerization process |
| US5801293A (en) * | 1996-02-26 | 1998-09-01 | Chevron U.S.A. Inc. | Method of isomerizing olefins |
| US6156947A (en) * | 1998-06-22 | 2000-12-05 | Uop Llc | Process for the production of butene-1 from a mixture of C4 olefins |
| US20030233018A1 (en) * | 2002-06-18 | 2003-12-18 | Brown Stephen H. | Method for isomerizing a mixed olefin feedstock to 1-olefin |
| US7531707B2 (en) | 2006-12-13 | 2009-05-12 | Chevron U.S.A., Inc | Alkylation process using an alkyl halide promoted ionic liquid catalyst |
| US20110144399A1 (en) * | 2006-12-14 | 2011-06-16 | Chevron U.S.A. Inc. | Process for producing alkylate with an increased ron |
| US7553999B2 (en) | 2006-12-14 | 2009-06-30 | Chevron U.S.A. Inc. | Isomerization of butene in the ionic liquid-catalyzed alkylation of light isoparaffins and olefins |
| US20090192339A1 (en) * | 2006-12-14 | 2009-07-30 | Chevron U.S.A., Inc. | Isomerization of butene in the ionic liquid-catalyzed alkylation of light isoparaffins and olefins |
| DE112007002597T5 (en) | 2006-12-14 | 2009-10-15 | Chevron U.S.A. Inc., San Ramon | Isomerization of butene in the alkylation of light isoparaffins and olefins catalyzed by ionic liquids |
| US20080146858A1 (en) * | 2006-12-14 | 2008-06-19 | Chevron U.S.A. Inc. | Isomerization of butene in the ionic liquid-catalyzed alkylation of light isoparaffins and olefins |
| US8198494B2 (en) | 2006-12-14 | 2012-06-12 | Chevron U.S.A. Inc. | Process for producing alkylate with an increased RON |
| US7915468B2 (en) | 2006-12-14 | 2011-03-29 | Chevron U.S.A. Inc. | Isomerization of butene in the ionic liquid-catalyzed alkylation of light isoparaffins and olefins |
| EP2671863A1 (en) | 2007-02-12 | 2013-12-11 | Chevron U.S.A. Inc. | Method of making diester-based lubricants |
| US8586519B2 (en) | 2007-02-12 | 2013-11-19 | Chevron U.S.A. Inc. | Multi-grade engine oil formulations comprising a bio-derived ester component |
| US20110053817A1 (en) * | 2007-02-12 | 2011-03-03 | Chevron U.S.A. Inc. | Multi-grade engine oil formulations comprising a bio-derived ester component |
| US20090159837A1 (en) * | 2007-12-21 | 2009-06-25 | Chevron U.S.A., Inc. | Refrigeration oil from gas-to-liquid-derived and bio-derived diesters |
| US20090159835A1 (en) * | 2007-12-21 | 2009-06-25 | Chevron U.S.A., Inc. | Refrigeration oil from gas-to-liquid-derived and bio-derived triesters |
| US7867959B2 (en) | 2008-01-31 | 2011-01-11 | Chevron U.S.A. Inc. | Synthesis of diester-based biolubricants from epoxides |
| US20110077184A1 (en) * | 2008-01-31 | 2011-03-31 | Chevron U.S.A. Inc. | Synthesis of diester-based biolubricants from epoxides |
| US20090198075A1 (en) * | 2008-01-31 | 2009-08-06 | Chevron U.S.A. Inc. | Synthesis of diester-based biolubricants from epoxides |
| US8575081B2 (en) | 2008-01-31 | 2013-11-05 | Chevron U.S.A. Inc. | Synthesis of diester-based biolubricants from epoxides |
| US20100120642A1 (en) * | 2008-11-13 | 2010-05-13 | Chevron U.S.A. Inc. | Synthesis of diester-based lubricants from enzymatically-directed epoxides |
| DE112009002718T5 (en) | 2008-11-13 | 2012-08-23 | Chevron U.S.A. Inc. | Synthesis of diester lubricants from enzyme-controlled epoxides |
| US9109238B2 (en) | 2008-11-13 | 2015-08-18 | Chevron U.S.A. Inc. | Synthesis of diester-based lubricants from enzymatically-directed epoxides |
| WO2011028329A2 (en) | 2009-08-26 | 2011-03-10 | Chevron U.S.A. Inc. | Multi-grade engine oil formulations comprising a bio-derived ester component |
| DE112011102541T5 (en) | 2010-07-29 | 2013-05-02 | Chevron U.S.A. Inc. | APPLICATION-SPECIFIC MANUFACTURED LUBRICANT COMPOSITIONS COMPRISING A BIOLOGICAL ESTER COMPONENT, AND METHOD FOR MANUFACTURING THE SAME |
| US8410033B2 (en) | 2010-08-26 | 2013-04-02 | Chevron U.S.A. Inc. | Preparation of diester-based biolubricants from monoesters of fatty acids and olefin-derived vicinal diols |
| DE112011104579T5 (en) | 2010-12-23 | 2013-09-26 | Chevron U.S.A. Inc. | High flash point esters as electrical insulating oils |
| WO2019183187A1 (en) | 2018-03-20 | 2019-09-26 | Basf Se | Lubricant composition |
| US12215294B2 (en) | 2018-03-20 | 2025-02-04 | Basf Se | Lubricant composition |
| EP3712235A1 (en) | 2019-03-20 | 2020-09-23 | Basf Se | Lubricant composition |
| WO2020190859A1 (en) | 2019-03-20 | 2020-09-24 | Basf Se | Lubricant composition |
| US11066620B2 (en) | 2019-03-20 | 2021-07-20 | Basf Se | Lubricant composition |
| US11739282B2 (en) | 2019-03-20 | 2023-08-29 | Basf Se | Lubricant composition |
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