BR112015006248B1 - métodos para refinar um óleo natural - Google Patents
métodos para refinar um óleo natural Download PDFInfo
- Publication number
- BR112015006248B1 BR112015006248B1 BR112015006248-2A BR112015006248A BR112015006248B1 BR 112015006248 B1 BR112015006248 B1 BR 112015006248B1 BR 112015006248 A BR112015006248 A BR 112015006248A BR 112015006248 B1 BR112015006248 B1 BR 112015006248B1
- Authority
- BR
- Brazil
- Prior art keywords
- ester
- olefin
- metathesis
- acid
- acid ester
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 120
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 370
- -1 olefin ester Chemical group 0.000 claims abstract description 324
- 239000003054 catalyst Substances 0.000 claims abstract description 246
- 238000005649 metathesis reaction Methods 0.000 claims abstract description 244
- 150000002148 esters Chemical class 0.000 claims abstract description 168
- QYMFNZIUDRQRSA-UHFFFAOYSA-N dimethyl butanedioate;dimethyl hexanedioate;dimethyl pentanedioate Chemical compound COC(=O)CCC(=O)OC.COC(=O)CCCC(=O)OC.COC(=O)CCCCC(=O)OC QYMFNZIUDRQRSA-UHFFFAOYSA-N 0.000 claims abstract description 118
- 239000002253 acid Substances 0.000 claims abstract description 102
- 239000002994 raw material Substances 0.000 claims abstract description 78
- 238000007670 refining Methods 0.000 claims abstract description 11
- 150000001336 alkenes Chemical class 0.000 claims description 357
- 239000000047 product Substances 0.000 claims description 205
- 239000000203 mixture Substances 0.000 claims description 167
- 238000006243 chemical reaction Methods 0.000 claims description 116
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 56
- 238000005686 cross metathesis reaction Methods 0.000 claims description 46
- 239000006227 byproduct Substances 0.000 claims description 39
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 31
- 229920006395 saturated elastomer Polymers 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- SBLKVIQSIHEQOF-UHFFFAOYSA-N octadec-9-enedioic acid Chemical compound OC(=O)CCCCCCCC=CCCCCCCCC(O)=O SBLKVIQSIHEQOF-UHFFFAOYSA-N 0.000 claims description 16
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 claims description 14
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 12
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 claims description 12
- FKLSONDBCYHMOQ-UHFFFAOYSA-N 9E-dodecenoic acid Natural products CCC=CCCCCCCCC(O)=O FKLSONDBCYHMOQ-UHFFFAOYSA-N 0.000 claims description 9
- OZKLKDKGPNBGPK-UHFFFAOYSA-N 9-Dodecenoic acid Natural products CCCC=CCCCCCCC(O)=O OZKLKDKGPNBGPK-UHFFFAOYSA-N 0.000 claims description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 8
- YCBSHDKATAPNIA-UHFFFAOYSA-N non-3-ene Chemical compound CCCCCC=CCC YCBSHDKATAPNIA-UHFFFAOYSA-N 0.000 claims description 6
- FKLSONDBCYHMOQ-ONEGZZNKSA-N trans-dodec-9-enoic acid Chemical compound CC\C=C\CCCCCCCC(O)=O FKLSONDBCYHMOQ-ONEGZZNKSA-N 0.000 claims description 6
- GZZPOFFXKUVNSW-UHFFFAOYSA-N Dodecenoic acid Natural products OC(=O)CCCCCCCCCC=C GZZPOFFXKUVNSW-UHFFFAOYSA-N 0.000 claims description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- YCTDZYMMFQCTEO-FNORWQNLSA-N (E)-3-octene Chemical compound CCCC\C=C\CC YCTDZYMMFQCTEO-FNORWQNLSA-N 0.000 claims description 4
- ADLXTJMPCFOTOO-BQYQJAHWSA-N (E)-non-2-enoic acid Chemical compound CCCCCC\C=C\C(O)=O ADLXTJMPCFOTOO-BQYQJAHWSA-N 0.000 claims description 4
- IICQZTQZQSBHBY-HWKANZROSA-N (e)-non-2-ene Chemical compound CCCCCC\C=C\C IICQZTQZQSBHBY-HWKANZROSA-N 0.000 claims description 4
- OTTZHAVKAVGASB-HYXAFXHYSA-N 2-Heptene Chemical compound CCCC\C=C/C OTTZHAVKAVGASB-HYXAFXHYSA-N 0.000 claims description 4
- OTTZHAVKAVGASB-UHFFFAOYSA-N 2-heptene Natural products CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 claims description 4
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 claims description 4
- IICQZTQZQSBHBY-UHFFFAOYSA-N 2t-nonene Natural products CCCCCCC=CC IICQZTQZQSBHBY-UHFFFAOYSA-N 0.000 claims description 4
- AWQOXJOAQMCOED-UHFFFAOYSA-N 8-Nonenoic acid Natural products OC(=O)CCCCCCC=C AWQOXJOAQMCOED-UHFFFAOYSA-N 0.000 claims description 4
- WZHKDGJSXCTSCK-UHFFFAOYSA-N hept-3-ene Chemical compound CCCC=CCC WZHKDGJSXCTSCK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 229960002703 undecylenic acid Drugs 0.000 claims description 4
- YWWVWXASSLXJHU-UHFFFAOYSA-N 9E-tetradecenoic acid Natural products CCCCC=CCCCCCCCC(O)=O YWWVWXASSLXJHU-UHFFFAOYSA-N 0.000 claims description 2
- YIYBQIKDCADOSF-UHFFFAOYSA-N alpha-Butylen-alpha-carbonsaeure Natural products CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 claims description 2
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 claims description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadecene Natural products CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 claims description 2
- IBYFOBGPNPINBU-UHFFFAOYSA-N tetradecenoic acid Natural products CCCCCCCCCCCC=CC(O)=O IBYFOBGPNPINBU-UHFFFAOYSA-N 0.000 claims description 2
- CAHZYAQCDBBLER-UHFFFAOYSA-N 14-pentadecenoic acid Chemical compound OC(=O)CCCCCCCCCCCCC=C CAHZYAQCDBBLER-UHFFFAOYSA-N 0.000 claims 1
- WXBXVVIUZANZAU-UHFFFAOYSA-N 2E-decenoic acid Natural products CCCCCCCC=CC(O)=O WXBXVVIUZANZAU-UHFFFAOYSA-N 0.000 claims 1
- HGGLIXDRUINGBB-UHFFFAOYSA-N dimethyl octadec-9-enedioate Chemical group COC(=O)CCCCCCCC=CCCCCCCCC(=O)OC HGGLIXDRUINGBB-UHFFFAOYSA-N 0.000 claims 1
- 239000003921 oil Substances 0.000 abstract description 117
- 150000007513 acids Chemical class 0.000 abstract description 16
- 238000004519 manufacturing process Methods 0.000 abstract description 12
- 235000019198 oils Nutrition 0.000 description 114
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 77
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 65
- 150000001875 compounds Chemical class 0.000 description 55
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- 238000005984 hydrogenation reaction Methods 0.000 description 53
- 239000000446 fuel Substances 0.000 description 52
- 238000000926 separation method Methods 0.000 description 50
- SBIGSHCJXYGFMX-UHFFFAOYSA-N methyl dec-9-enoate Chemical compound COC(=O)CCCCCCCC=C SBIGSHCJXYGFMX-UHFFFAOYSA-N 0.000 description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
- 238000006317 isomerization reaction Methods 0.000 description 41
- 229910001868 water Inorganic materials 0.000 description 38
- 239000007789 gas Substances 0.000 description 36
- 238000005809 transesterification reaction Methods 0.000 description 36
- 239000003153 chemical reaction reagent Substances 0.000 description 34
- 239000000543 intermediate Substances 0.000 description 34
- 229910052757 nitrogen Inorganic materials 0.000 description 32
- 238000003786 synthesis reaction Methods 0.000 description 31
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 30
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 30
- 238000004821 distillation Methods 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- 235000014113 dietary fatty acids Nutrition 0.000 description 29
- 239000000194 fatty acid Substances 0.000 description 29
- 229930195729 fatty acid Natural products 0.000 description 29
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 26
- 238000012545 processing Methods 0.000 description 25
- 150000002430 hydrocarbons Chemical class 0.000 description 24
- 230000008569 process Effects 0.000 description 24
- 239000000523 sample Substances 0.000 description 23
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 22
- 239000005977 Ethylene Substances 0.000 description 22
- 238000009826 distribution Methods 0.000 description 22
- 150000004702 methyl esters Chemical class 0.000 description 21
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- JMXMXKRNIYCNRV-UHFFFAOYSA-N bis(hydroxymethyl)phosphanylmethanol Chemical compound OCP(CO)CO JMXMXKRNIYCNRV-UHFFFAOYSA-N 0.000 description 20
- DUWQEMMRMJGHSA-UHFFFAOYSA-N methyl dodec-9-enoate Chemical compound CCC=CCCCCCCCC(=O)OC DUWQEMMRMJGHSA-UHFFFAOYSA-N 0.000 description 20
- 239000000126 substance Substances 0.000 description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 17
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- 239000002904 solvent Substances 0.000 description 17
- 238000000605 extraction Methods 0.000 description 16
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 229930195733 hydrocarbon Natural products 0.000 description 15
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 14
- 235000019482 Palm oil Nutrition 0.000 description 14
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- 125000005456 glyceride group Chemical group 0.000 description 13
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- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 229910052759 nickel Inorganic materials 0.000 description 13
- QYDYPVFESGNLHU-ZHACJKMWSA-N Methyl (9E)-9-octadecenoate Chemical compound CCCCCCCC\C=C\CCCCCCCC(=O)OC QYDYPVFESGNLHU-ZHACJKMWSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 12
- 235000011187 glycerol Nutrition 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- BNJOQKFENDDGSC-UHFFFAOYSA-N octadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCCC(O)=O BNJOQKFENDDGSC-UHFFFAOYSA-N 0.000 description 12
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- HGGLIXDRUINGBB-ONEGZZNKSA-N dimethyl (e)-octadec-9-enedioate Chemical compound COC(=O)CCCCCCC\C=C\CCCCCCCC(=O)OC HGGLIXDRUINGBB-ONEGZZNKSA-N 0.000 description 7
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/475—Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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| US13/647,825 | 2012-10-09 | ||
| US13/647,825 US8735640B2 (en) | 2009-10-12 | 2012-10-09 | Methods of refining and producing fuel and specialty chemicals from natural oil feedstocks |
| US13/647,809 | 2012-10-09 | ||
| PCT/US2013/063861 WO2014058867A1 (en) | 2012-10-09 | 2013-10-08 | Methods of refining and producing dibasic esters and acids from natural oil feedstocks |
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| CA2899443A1 (en) * | 2013-03-14 | 2014-10-02 | Elevance Renewable Sciences, Inc. | Methods of refining and producing isomerized fatty acid esters and fatty acids from natural oil feedstocks |
| US9963420B2 (en) | 2015-03-24 | 2018-05-08 | Elevance Renewable Sciences, Inc. | Polyol esters of metathesized fatty acids and uses thereof |
| US9796657B2 (en) * | 2015-03-24 | 2017-10-24 | Elevance Renewable Sciences, Inc. | Polyol esters of metathesized fatty acids and uses thereof |
| CN105974899A (zh) * | 2016-06-12 | 2016-09-28 | 江门谦信化工发展有限公司 | 一种酯化反应添加硫酸催化剂的自动控制系统及其使用方法 |
| US10155833B2 (en) * | 2016-08-18 | 2018-12-18 | Elevance Renewable Sciences, Inc. | High-weight glyceride oligomers and methods of making the same |
| JP6503600B2 (ja) * | 2017-01-12 | 2019-04-24 | 株式会社新菱 | 水素ガス含有材料の製造方法および水素ガス含有材料の製造装置 |
| HUE073559T2 (hu) | 2017-02-17 | 2026-01-28 | Provivi Inc | Feromonok és kapcsolódó anyagok szintézise olefin-metatézisen keresztül |
| EP3483233A1 (en) * | 2017-11-10 | 2019-05-15 | Arkema France | Lubricant base oil compositions of mono-unsaturated dibasic acid esters with branched alcohols |
| FI128952B (en) | 2019-09-26 | 2021-03-31 | Neste Oyj | Preparation of renewable alkenes including metathesis |
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| US3150205A (en) | 1960-09-07 | 1964-09-22 | Standard Oil Co | Paraffin isomerization process |
| US3351566A (en) | 1963-10-21 | 1967-11-07 | Exxon Research Engineering Co | Stabilized high-activity catalyst |
| US4210771A (en) | 1978-11-02 | 1980-07-01 | Union Carbide Corporation | Total isomerization process |
| NL190750C (nl) | 1984-06-21 | 1994-08-01 | Unilever Nv | Nikkelaluminaat katalysator, de bereiding daarvan en het hydrogeneren van onverzadigde organische verbindingen daarmee. |
| US5095169A (en) | 1988-03-30 | 1992-03-10 | Uop | Normal paraffin hydrocarbon isomerization process using activated zeolite beta |
| EP0936266B1 (en) * | 1998-02-13 | 2008-12-24 | Lipidia Holding S.A. | Refining of edible oil retaining maximum antioxidative potency |
| US6214764B1 (en) | 1999-06-01 | 2001-04-10 | Uop Llc | Paraffin-isomerization catalyst and process |
| US6307077B1 (en) * | 1999-08-09 | 2001-10-23 | Robert Michael Quear | Method for purifying vegetable oil obtained by mechanical extraction |
| GB0017839D0 (en) | 2000-07-21 | 2000-09-06 | Ici Plc | Hydrogenation catalysts |
| WO2002076920A1 (en) * | 2001-03-26 | 2002-10-03 | Dow Global Technologies Inc. | Metathesis of unsaturated fatty acid esters or unsaturated fatty acids with lower olefins |
| RU2352549C2 (ru) * | 2002-04-29 | 2009-04-20 | Дау Глобал Текнолоджиз Инк. | Интегрированные химические способы промышленного применения растительных масел из семян |
| CA2592786C (en) | 2005-01-10 | 2013-11-19 | Cargill, Incorporated | Candle and candle wax containing metathesis and metathesis-like products |
| EP2076484B1 (en) * | 2006-10-13 | 2020-01-08 | Elevance Renewable Sciences, Inc. | Synthesis of terminal alkenes from internal alkenes via olefin metathesis |
| FR2917406B1 (fr) * | 2007-06-13 | 2012-08-03 | Arkema France | Procede de synthese de diacides ou diesters a partir d'acides et/ou d'esters gras naturels |
| CA2695903C (en) | 2007-08-09 | 2015-11-03 | Daniel W. Lemke | Chemical methods for treating a metathesis feedstock |
| CA2695865C (en) | 2007-08-09 | 2015-12-01 | Elevance Renewable Sciences, Inc. | Thermal methods for treating a metathesis feedstock |
| WO2010021740A1 (en) * | 2008-08-21 | 2010-02-25 | Materia, Inc. | Telechelic olefin metathesis polymers from renewable feedstocks |
| US9000246B2 (en) * | 2009-10-12 | 2015-04-07 | Elevance Renewable Sciences, Inc. | Methods of refining and producing dibasic esters and acids from natural oil feedstocks |
| JP6224896B2 (ja) * | 2009-10-12 | 2017-11-01 | エレバンス・リニューアブル・サイエンシズ，インコーポレーテッド | 天然油供給原料から燃料を精製および製造する方法 |
| MX339493B (es) * | 2010-10-25 | 2016-05-26 | Stepan Co | Esteraminas y derivados de la metatesis de aceite natural. |
-
2013
- 2013-10-08 AU AU2013329413A patent/AU2013329413B2/en active Active
- 2013-10-08 MY MYPI2015000592A patent/MY182542A/en unknown
- 2013-10-08 MX MX2015003198A patent/MX370894B/es active IP Right Grant
- 2013-10-08 EP EP13783149.1A patent/EP2906527B1/en active Active
- 2013-10-08 JP JP2015535888A patent/JP6460994B2/ja active Active
- 2013-10-08 HU HUE13783149A patent/HUE053411T2/hu unknown
- 2013-10-08 EA EA201590377A patent/EA201590377A1/ru unknown
- 2013-10-08 BR BR112015006248-2A patent/BR112015006248B1/pt active IP Right Grant
- 2013-10-08 CA CA2884257A patent/CA2884257C/en active Active
- 2013-10-08 CN CN201380064256.2A patent/CN104837802B/zh active Active
- 2013-10-08 WO PCT/US2013/063861 patent/WO2014058867A1/en not_active Ceased
- 2013-10-08 KR KR1020157010031A patent/KR102224298B1/ko active Active
- 2013-10-08 SG SG11201501862WA patent/SG11201501862WA/en unknown
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2015
- 2015-03-10 ZA ZA2015/01624A patent/ZA201501624B/en unknown
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|---|---|
| CN104837802B (zh) | 2017-08-15 |
| EP2906527B1 (en) | 2020-12-09 |
| MX370894B (es) | 2020-01-09 |
| MX2015003198A (es) | 2015-10-09 |
| JP2015533829A (ja) | 2015-11-26 |
| ZA201501624B (en) | 2016-06-29 |
| AU2013329413A1 (en) | 2015-04-02 |
| HUE053411T2 (hu) | 2021-06-28 |
| EA201590377A1 (ru) | 2015-08-31 |
| SG11201501862WA (en) | 2015-05-28 |
| MY182542A (en) | 2021-01-25 |
| IL237703A0 (en) | 2015-05-31 |
| BR112015006248A2 (pt) | 2017-07-04 |
| JP2018109006A (ja) | 2018-07-12 |
| JP6460994B2 (ja) | 2019-01-30 |
| EP2906527A1 (en) | 2015-08-19 |
| CA2884257A1 (en) | 2014-04-17 |
| CN104837802A (zh) | 2015-08-12 |
| KR102224298B1 (ko) | 2021-03-05 |
| WO2014058867A1 (en) | 2014-04-17 |
| AU2013329413B2 (en) | 2017-11-23 |
| CA2884257C (en) | 2022-07-26 |
| KR20150064738A (ko) | 2015-06-11 |
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