DK2250241T3 - Syntese af diesterbaserede bio-smøremidler ud fra epoxider - Google Patents
Syntese af diesterbaserede bio-smøremidler ud fra epoxider Download PDFInfo
- Publication number
- DK2250241T3 DK2250241T3 DK08871667.5T DK08871667T DK2250241T3 DK 2250241 T3 DK2250241 T3 DK 2250241T3 DK 08871667 T DK08871667 T DK 08871667T DK 2250241 T3 DK2250241 T3 DK 2250241T3
- Authority
- DK
- Denmark
- Prior art keywords
- isomers
- acid
- ester
- pentyl
- hexyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/38—Esters of polyhydroxy compounds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/24—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
- C07C67/26—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M177/00—Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
- C10M2207/2835—Esters of polyhydroxy compounds used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2080/00—Special pretreatment of the material to be lubricated, e.g. phosphatising or chromatising of a metal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Lubricants (AREA)
Claims (16)
1. Fremgangsmåde omfattende: a) epoxidisering af en olefin med et carbontal på 8 til 16 for at danne en epoxid omfattende en epoxidring; og b) direkte esterificering af epoxiden med en C2. til Ci8-carboxylsyre for at danne en diesterforbindelse til anvendelse som et smøremiddel, hvor diester-forbindelsen harden følgende struktur:
hvor Ri, R2, R3 og R4 er de samme eller uafhængigt udvalgt blandt C2. til C17-hydrocarbongrupper.
2. Fremgangsmåde ifølge krav 1, hvor olefinen isomeriseres fra en a-olefin til en indre olefin.
3. Fremgangsmåde ifølge krav 2, hvor olefinen isomeriseres på dobbeltbindingen med en olefin-isomeriseringskatalysator.
4. Fremgangsmåde ifølge krav 1, hvor trinnet med direkte esterificering katalyseres ved nærvær af en syrekatalysator.
5. Fremgangsmåde ifølge krav 4, hvor syrekatalysatoren er udvalgt fra gruppen bestående af H3P04, H2S04, sulfonsyre, Lewis-syrer, silicium- og aluminiumbaserede faste syrer, amberlyst, tungstenoxid og kombinationer deraf.
6. Fremgangsmåde ifølge krav 1, hvor trinnet med direkte esterificering yderligere omfatter forekomsten af en carboxylsyreanhydrid.
7. Fremgangsmåde ifølge krav 1, yderligere omfattende et trin med at blande diesterforbindelsen med en eller flere andre forbindelser udvalgt fra gruppen bestående af andre diesterforbindelser, Gruppe l-olier, Gruppe Il-olier, Gruppe 11 l-olier og blandinger deraf.
8. Fremgangsmåde ifølge krav 1, hvor olefinen er et Fischer-Tropsch-reak-tionsprodukt, eller hvor olefinen kan afledes fra pyrolyse af affaldsplast.
9. Fremgangsmåde ifølge krav 1, hvor carboxylsyren kan afledes fra biomasse.
10. Fremgangsmåde ifølge krav 1, hvor den dannede di esterforbindelse er udvalgt fra gruppen bestående af decansyre-2-decanoyloxy-1-hexyl-octyl-ester og dens isomerer, tetradecansyre-1-hexyl-2-tetradecanoyloxy-octyl-estere og dens isomerer, dodecansyre-2-dodecanoyloxy-1-hexyl-octylester og dens isomerer, hexansyre-2-hexanoyloxy-1-hexy-octylester og dens isomerer, octansyre-2-octanoyloxy-1-hexyl-octylester og dens isomerer, hexan-syre-2-hexanoyloxy-1-pentyl-heptylester og isomerer, octansyre-2-octanoyl-oxy-1-pentyl-heptylester og isomerer, decansyre-2-decanoyloxy-1-pentyl-heptylester og isomerer, decansyre-2-cecanoyloxy-1-pentyl-heptylester og dens isomerer, dodecansyre-2-dodecanoyloxy-1-pentyl-heptylester og isomerer, tetradecansyre-1-pentyl-2-tetradecanoyloxy-heptylester og isomerer, tetradecansyre-1-butyl-2-tetradecanoyloxy-hexylester og isomerer, dodecan-syre-1-butyl-2-dodecanoyloxy-hexylester og isomerer, decansyre-1-butyl-2-decanoyloxy-hexylester og isomerer, octansyre-1-butyl-2-octanoyloxy-hexyl-ester og isomerer, hexansyre-1-butyl-2-hexanoyloxy-hexylester og isomerer, tetradecansyre-1-propyl-2-tetradecanoyloxy-pentylester og isomerer, dode-cansyre-2-dodecanoyloxy-1-propyl-pentylester og isomerer, decansyre-2-decanoyloxy-1-propyl-pentylester og isomerer, octansyre-2-octanoyloxy-1-propyl-pentylester og isomerer, hexansyre-2-hexanoyloxy-1-propyl-pentyl-ester og isomerer og blandinger deraf.
11. Fremgangsmåde omfattende: (a) epoxidisering af en flerhed af olefiner, hvilke olefiner har et carbontal på 8 til 16, for at danne en flerhed af epoxider, hvoraf hver af dem omfatter en epoxidring; og (b) direkte esterificering af epoxiderne med en flerhed af C2- til Ci8-carboxyl-syrer, omdannelse af mindre end 10 procent af epoxiderne til dioler for at danne en disestersammensætningen til anvendelse som et smøremiddel, hvor diester-sammensætninge omfatter en mængde af diesterforbindelser, som har den følgende struktur:
hvor Ri, R2, R3, og R4 er de samme eller uafhængigt udvalgt blandt C2-til C17-hydrocarbongrupper.
12. Fremgangsmåde ifølge krav 11, hvor trinnet med esterificering katalyseres ved nærvær af en syrekatalysator.
13. Fremgangsmåde ifølge krav 11, hvor trinnet med esterificering yderligere omfatter nærvær af en carboxylsyreanhydrid.
14. Fremgangsmåde ifølge krav 11, hvor mindst nogle fra flerheden af olefiner kan afledes fra en forudgående fremgangsmåde udvalgt fra gruppen bestående af Fischer-Tropsch-syntese, pyrolyse af affaldsplast og kombinationer deraf.
15. Fremgangsmåde ifølge krav 11, hvor mindst nogle af carboxyl syrerne kan afledes fra biomasse.
16. Fremgangsmåde ifølge krav 11, hvor den dannede diestersammensæt-ning omfatter diesterforbindelser udvalgt fra gruppen bestående af decansy-re-2-decanoyloxy-1-hexyl-octylester og dens isomerer, tetradecansyre-1-hexyl-2-tetradecanoyloxy-octylestere og dens isomerer, dodecansyre-2-do-decanoyloxy-1-hexyl-octylester og dens isomerer, hexansyre-2-hexanoyloxy-1-hexy-octylester og dens isomerer, octansyre-2-octanoyloxy-1-hexyl-octyl-ester og dens isomerer, hexansyre-2-hexanoyloxy-1-pentyl-heptylester og isomerer, octansyre-2-octanoyloxy-1-pentyl-heptylester og isomerer, decan-syre-2-decanoyloxy-1-pentyl-heptylester og isomerer, decansyre-2-cecanoyl-oxy-1-pentyl-heptylester og dens isomerer, dodecansyre-2-dodecanoyloxy-1-pentyl-heptylester og isomerer, tetradecansyre-1-pentyl-2-tetradecanoyloxy-heptylester og isomerer, tetradecansyre-1-butyl-2-tetradecanoyloxy-hexyl-ester og isomerer, dodecansyre-1-butyl-2-dodecanoyloxy-hexylester og isomerer, decansyre 1-butyl-2-decanoyloxy-hexylester og isomerer, octansyre-1-butyl-2-octanoyloxy-hexylester og isomerer, hexansyre-1-butyl-2-hexanoyl-oxy-hexyl ester og isomerer, tetradecansyre-1-propyl-2-tetradecanoyloxy-pen-tylester og isomerer, dodecansyre-2-dodecanoyloxy-1-propyl-pentylester og isomerer, decansyre-2-decanoyloxy-1-propyl-pentylester og isomerer, octan-syre-2-octanoyloxy-1-propyl-pentylester og isomerer, hexansyre-2-hexanoyl-oxy-1-propyl-pentylester og isomerer og blandinger deraf.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/023,695 US7867959B2 (en) | 2008-01-31 | 2008-01-31 | Synthesis of diester-based biolubricants from epoxides |
PCT/US2008/083899 WO2009097041A1 (en) | 2008-01-31 | 2008-11-18 | Synthesis of diester-based biolubricants from epoxides |
Publications (1)
Publication Number | Publication Date |
---|---|
DK2250241T3 true DK2250241T3 (da) | 2017-04-03 |
Family
ID=40913125
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK08871667.5T DK2250241T3 (da) | 2008-01-31 | 2008-11-18 | Syntese af diesterbaserede bio-smøremidler ud fra epoxider |
Country Status (10)
Country | Link |
---|---|
US (2) | US7867959B2 (da) |
EP (1) | EP2250241B1 (da) |
CN (1) | CN101932682B (da) |
BR (1) | BRPI0821944A2 (da) |
CA (1) | CA2712435C (da) |
DK (1) | DK2250241T3 (da) |
ES (1) | ES2625691T3 (da) |
MX (1) | MX2010007934A (da) |
PL (1) | PL2250241T3 (da) |
WO (1) | WO2009097041A1 (da) |
Families Citing this family (29)
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US7871967B2 (en) * | 2007-02-12 | 2011-01-18 | Chevron U.S.A. Inc. | Diester-based lubricants and methods of making same |
US20090159835A1 (en) * | 2007-12-21 | 2009-06-25 | Chevron U.S.A., Inc. | Refrigeration oil from gas-to-liquid-derived and bio-derived triesters |
US8795547B2 (en) * | 2007-12-21 | 2014-08-05 | 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 |
US9109238B2 (en) * | 2008-11-13 | 2015-08-18 | Chevron U.S.A. Inc. | Synthesis of diester-based lubricants from enzymatically-directed epoxides |
US8057558B2 (en) * | 2008-12-23 | 2011-11-15 | Chevron U.S.A. Inc. | Enhanced biodiesel fuel having improved low-temperature properties and methods of making same |
US20110009300A1 (en) | 2009-07-07 | 2011-01-13 | Chevron U.S.A. Inc. | Synthesis of biolubricant esters from unsaturated fatty acid derivatives |
US20120028863A1 (en) * | 2010-07-29 | 2012-02-02 | David Christian Kramer | Application-specific finished lubricant compositions comprising a bio-derived ester component and methods of making same |
GB2493485A (en) * | 2010-07-29 | 2013-02-06 | Chevron Usa Inc | Application-specific finished lubricant compositions comprisina bio-derived ester component and methods of making 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 |
CA2813286A1 (fr) * | 2010-10-27 | 2012-05-03 | Universite De Poitiers | Procede de fonctionnalisation de composes insatures |
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US8741822B2 (en) * | 2011-02-13 | 2014-06-03 | Trent University | Esters for use as a base stock and in lubricant applications |
US20130029891A1 (en) * | 2011-07-27 | 2013-01-31 | Chevron U.S.A. | Turbine oil comprising an ester component |
US20130085091A1 (en) * | 2011-09-29 | 2013-04-04 | Chevron U.S.A. Inc. | Industrial oil comprising a bio-derived ester |
CN105189715A (zh) | 2013-05-03 | 2015-12-23 | 雪佛龙美国公司 | 具有改进的低温流动性能和低noack值的二酯基基础油调和物 |
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ES2590220B1 (es) | 2015-05-18 | 2017-12-18 | Neol Biosolutions, S.A. | Producción de aceites microbianos con alto contenido en acido oleico |
US10125337B2 (en) * | 2015-11-16 | 2018-11-13 | Trent University | Branched diesters and methods of making and using the same |
CN111056944B (zh) * | 2018-10-16 | 2022-07-15 | 中国石油化工股份有限公司 | 一种酚酯类化合物及其制备方法、用途 |
US11739282B2 (en) | 2019-03-20 | 2023-08-29 | Basf Se | Lubricant composition |
JP2023501643A (ja) | 2019-11-14 | 2023-01-18 | エボニック オペレーションズ ゲーエムベーハー | α-オレフィンを不均一系触媒により異性化する方法 |
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US7867959B2 (en) | 2008-01-31 | 2011-01-11 | Chevron U.S.A. Inc. | Synthesis of diester-based biolubricants from epoxides |
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-
2008
- 2008-01-31 US US12/023,695 patent/US7867959B2/en active Active
- 2008-11-18 CN CN2008801259425A patent/CN101932682B/zh active Active
- 2008-11-18 DK DK08871667.5T patent/DK2250241T3/da active
- 2008-11-18 PL PL08871667T patent/PL2250241T3/pl unknown
- 2008-11-18 EP EP08871667.5A patent/EP2250241B1/en active Active
- 2008-11-18 CA CA2712435A patent/CA2712435C/en active Active
- 2008-11-18 BR BRPI0821944-3A patent/BRPI0821944A2/pt not_active Application Discontinuation
- 2008-11-18 WO PCT/US2008/083899 patent/WO2009097041A1/en active Application Filing
- 2008-11-18 MX MX2010007934A patent/MX2010007934A/es active IP Right Grant
- 2008-11-18 ES ES08871667.5T patent/ES2625691T3/es active Active
-
2010
- 2010-12-07 US US12/962,193 patent/US8575081B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
PL2250241T3 (pl) | 2017-09-29 |
US8575081B2 (en) | 2013-11-05 |
CA2712435A1 (en) | 2009-08-06 |
ES2625691T3 (es) | 2017-07-20 |
EP2250241B1 (en) | 2016-12-21 |
CA2712435C (en) | 2016-04-19 |
BRPI0821944A2 (pt) | 2015-06-23 |
EP2250241A1 (en) | 2010-11-17 |
WO2009097041A1 (en) | 2009-08-06 |
MX2010007934A (es) | 2010-11-30 |
US20110077184A1 (en) | 2011-03-31 |
US7867959B2 (en) | 2011-01-11 |
EP2250241A4 (en) | 2012-02-29 |
CN101932682B (zh) | 2013-08-21 |
US20090198075A1 (en) | 2009-08-06 |
CN101932682A (zh) | 2010-12-29 |
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