JP2015513547A5 - - Google Patents
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- Publication number
- JP2015513547A5 JP2015513547A5 JP2014559855A JP2014559855A JP2015513547A5 JP 2015513547 A5 JP2015513547 A5 JP 2015513547A5 JP 2014559855 A JP2014559855 A JP 2014559855A JP 2014559855 A JP2014559855 A JP 2014559855A JP 2015513547 A5 JP2015513547 A5 JP 2015513547A5
- Authority
- JP
- Japan
- Prior art keywords
- isomer
- ozone
- azeotroped
- monoalcohol
- water
- 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.)
- Granted
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- 238000000034 method Methods 0.000 claims 29
- 229920005862 polyol Polymers 0.000 claims 19
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims 17
- -1 ester polyol Chemical class 0.000 claims 16
- 239000000203 mixture Substances 0.000 claims 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 13
- 235000014113 dietary fatty acids Nutrition 0.000 claims 12
- 229930195729 fatty acid Natural products 0.000 claims 12
- 239000000194 fatty acid Substances 0.000 claims 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 9
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 8
- 150000004665 fatty acids Chemical class 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims 6
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- 239000000126 substance Substances 0.000 claims 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims 4
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 claims 4
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 claims 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims 4
- WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 claims 4
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 claims 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims 4
- 150000003077 polyols Chemical class 0.000 claims 4
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- 239000005968 1-Decanol Substances 0.000 claims 2
- RXGUIWHIADMCFC-UHFFFAOYSA-N 2-Methylpropyl 2-methylpropionate Chemical compound CC(C)COC(=O)C(C)C RXGUIWHIADMCFC-UHFFFAOYSA-N 0.000 claims 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 2
- 239000003377 acid catalyst Substances 0.000 claims 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims 2
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 claims 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 claims 2
- 239000012974 tin catalyst Substances 0.000 claims 2
- NGCDGPPKVSZGRR-UHFFFAOYSA-J 1,4,6,9-tetraoxa-5-stannaspiro[4.4]nonane-2,3,7,8-tetrone Chemical group [Sn+4].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O NGCDGPPKVSZGRR-UHFFFAOYSA-J 0.000 claims 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 claims 1
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical group NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims 1
- 235000019737 Animal fat Nutrition 0.000 claims 1
- 229930091371 Fructose Natural products 0.000 claims 1
- 239000005715 Fructose Substances 0.000 claims 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 1
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 claims 1
- 208000007976 Ketosis Diseases 0.000 claims 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims 1
- 235000019482 Palm oil Nutrition 0.000 claims 1
- 235000021314 Palmitic acid Nutrition 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- 235000021355 Stearic acid Nutrition 0.000 claims 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims 1
- 229930006000 Sucrose Natural products 0.000 claims 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001323 aldoses Chemical class 0.000 claims 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims 1
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229960000541 cetyl alcohol Drugs 0.000 claims 1
- 150000002016 disaccharides Chemical class 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 238000005194 fractionation Methods 0.000 claims 1
- 239000008103 glucose Substances 0.000 claims 1
- 235000011187 glycerol Nutrition 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 150000002584 ketoses Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 229940017219 methyl propionate Drugs 0.000 claims 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 1
- 238000005949 ozonolysis reaction Methods 0.000 claims 1
- 239000002540 palm oil Substances 0.000 claims 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000008117 stearic acid Substances 0.000 claims 1
- 239000005720 sucrose Substances 0.000 claims 1
- 150000005846 sugar alcohols Chemical class 0.000 claims 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims 1
- 229910001887 tin oxide Inorganic materials 0.000 claims 1
- 238000005809 transesterification reaction Methods 0.000 claims 1
- 150000003626 triacylglycerols Chemical class 0.000 claims 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 235000015112 vegetable and seed oil Nutrition 0.000 claims 1
- 239000008158 vegetable oil Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261604165P | 2012-02-28 | 2012-02-28 | |
| US61/604,165 | 2012-02-28 | ||
| PCT/MY2013/000042 WO2013129911A1 (en) | 2012-02-28 | 2013-02-28 | Bio-polyols for bio-lubricant and bio-polymer and methods for the preparation thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017194379A Division JP6524171B2 (ja) | 2012-02-28 | 2017-10-04 | バイオ潤滑剤およびバイオポリマーのためのバイオポリオール類、およびそれらの生成方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015513547A JP2015513547A (ja) | 2015-05-14 |
| JP2015513547A5 true JP2015513547A5 (cg-RX-API-DMAC7.html) | 2015-12-24 |
| JP6265919B2 JP6265919B2 (ja) | 2018-01-24 |
Family
ID=49083020
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014559855A Active JP6265919B2 (ja) | 2012-02-28 | 2013-02-28 | バイオ潤滑剤およびバイオポリマーのためのバイオポリオール類、およびそれらの生成方法 |
| JP2017194379A Active JP6524171B2 (ja) | 2012-02-28 | 2017-10-04 | バイオ潤滑剤およびバイオポリマーのためのバイオポリオール類、およびそれらの生成方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017194379A Active JP6524171B2 (ja) | 2012-02-28 | 2017-10-04 | バイオ潤滑剤およびバイオポリマーのためのバイオポリオール類、およびそれらの生成方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9302976B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2819990B1 (cg-RX-API-DMAC7.html) |
| JP (2) | JP6265919B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR102061375B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN104302614B (cg-RX-API-DMAC7.html) |
| MY (1) | MY186982A (cg-RX-API-DMAC7.html) |
| SG (1) | SG11201405261TA (cg-RX-API-DMAC7.html) |
| WO (1) | WO2013129911A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6265919B2 (ja) | 2012-02-28 | 2018-01-24 | ペトロリアム ナショナル ブルハドＰｅｔｒｏｌｉａｍ Ｎａｓｉｏｎａｌ Ｂｅｒｈａｄ | バイオ潤滑剤およびバイオポリマーのためのバイオポリオール類、およびそれらの生成方法 |
| KR102212416B1 (ko) | 2012-02-28 | 2021-02-05 | 페트롤리암 내셔널 버하드 (페트로나스) | 폴리우레탄 적용을 위한 폴리올의 조성물 |
| CN104271546B (zh) | 2012-02-28 | 2017-06-09 | 马来西亚国家石油公司 | 酯的生产方法及其用途 |
| MY171087A (en) | 2012-02-28 | 2019-09-24 | Petroliam Nasional Berhad | Method for the production of polyols and uses thereof |
| MY165638A (en) | 2012-02-28 | 2018-04-18 | Petroliam Nasional Berhad Petronas | Lubricant composition of matter and methods of preparation |
| MY169226A (en) | 2013-02-28 | 2019-03-19 | Petroliam Nasional Berhad | Preparation of biopolyol esters for lubricant application |
| CN106543990B (zh) * | 2015-09-23 | 2019-10-29 | 中国石油化工股份有限公司 | 一种提高泥岩钻进速度的钻井液及其制备方法和应用 |
| CN105399603B (zh) * | 2015-12-22 | 2018-07-31 | 山东理工大学 | 同时合成2,2,4-三甲基-1,3-戊二醇双异丁酸酯和2,2,4-三甲基-1,3-戊二醇的方法 |
| CN105801416B (zh) * | 2016-04-06 | 2018-08-10 | 江苏飞航工大科技有限公司 | 一种生物基多元醇及其制备方法 |
| WO2019182168A1 (ko) * | 2018-03-20 | 2019-09-26 | (주)이바이오코리아 | 생분해 다기능 방청 윤활유 |
| US11845903B2 (en) * | 2021-11-02 | 2023-12-19 | ExxonMobil Technology and Engineering Company | High yield jet fuel and chemicals from ozonolysis of triglycerides |
Family Cites Families (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2566559A (en) | 1951-09-04 | Preparation of agetals | ||
| US667043A (en) | 1900-09-13 | 1901-01-29 | James Steep | Seed-drill. |
| US2401338A (en) | 1941-09-23 | 1946-06-04 | Buckeye Lab Corp | Treatment of vegetable fatty substances |
| US2813113A (en) | 1953-05-07 | 1957-11-12 | Emery Industries Inc | Method of making azelaic acid |
| US2997493A (en) | 1959-09-29 | 1961-08-22 | Procter & Gamble | Method for preparing straight chain hexitol fatty esters |
| FR2254633B1 (cg-RX-API-DMAC7.html) | 1973-12-12 | 1976-10-08 | Inst Francais Du Petrole | |
| US4263216A (en) | 1978-10-20 | 1981-04-21 | The Procter & Gamble Company | Diglyceride manufacture |
| IE50028B1 (en) | 1979-12-19 | 1986-02-05 | Tate & Lyle Plc | Process for the production of a surfactant containing sucrose esters |
| US4313890A (en) | 1980-01-29 | 1982-02-02 | Union Carbide Corporation | Polyol ester functional fluids |
| JPS57185235A (en) * | 1981-05-07 | 1982-11-15 | Mitsui Toatsu Chem Inc | Preparation of neopentyl polyol ester from fatty acid |
| DE4219140C2 (de) * | 1991-06-12 | 1995-01-19 | Frische Gmbh | Verfahren zur Herstellung eines von bei der Weiterverarbeitung störenden Bestandteilen befreiten Triglycerid-Gemisches |
| DE4124665A1 (de) * | 1991-07-25 | 1993-01-28 | Henkel Kgaa | Verfahren zur herstellung von polyolverbindungen |
| US5773256A (en) | 1991-08-12 | 1998-06-30 | Ulice Sa | Methods for the production of esters of α-glucosides and uses thereof |
| ATE195545T1 (de) | 1992-06-03 | 2000-09-15 | Henkel Corp | Schmiermittel auf basis von polyolester für kälteübertragungsmittel |
| BR9504838A (pt) | 1994-11-15 | 1997-10-07 | Lubrizol Corp | Ester de poliol composição de óleo lubrificante |
| DE19727950A1 (de) | 1997-07-01 | 1999-01-07 | Clariant Gmbh | Verfahren zur Herstellung von Mischungen aus Sorbitmonoestern, Sorbitdiestern und Partialglyceriden |
| UA62017C2 (en) | 1998-12-28 | 2003-12-15 | A method for producing glyoxylic acid esters or hydrates thereof | |
| GB0112557D0 (en) | 2001-05-23 | 2001-07-11 | Infineum Int Ltd | A process for manufacturing monoesters of polyhydroxyalcohols |
| WO2003020782A2 (en) * | 2001-08-29 | 2003-03-13 | Ptc Organics, Inc. | Transesterification using phase transfer catalysts |
| MY140833A (en) | 2003-03-18 | 2010-01-29 | Univ Putra Malaysia | Palm oil based trimethylolpropane esters |
| US7125950B2 (en) | 2003-04-30 | 2006-10-24 | Board Of Trustees Of Michigan State University | Polyol fatty acid polyesters process and polyurethanes therefrom |
| US7192457B2 (en) * | 2003-05-08 | 2007-03-20 | Cargill, Incorporated | Wax and wax-based products |
| EP1529828A1 (en) | 2003-10-31 | 2005-05-11 | Malaysian Palm Oil Board | Lubricant base oil of palm fatty acid origin |
| MY141241A (en) | 2003-11-20 | 2010-03-31 | Malaysia Palm Oil Board | Lubricant base from palm oil and its by-products |
| WO2006093874A2 (en) * | 2005-02-28 | 2006-09-08 | Michigan State University | Novel triglycerides and method of preparation thereof |
| PL1883690T3 (pl) | 2005-04-26 | 2012-07-31 | Battelle Memorial Institute | Sposoby produkcji polioli z olei i ich stosowanie w produkcji poliestrów i poliuretanów |
| US20100087350A1 (en) | 2007-04-09 | 2010-04-08 | Sonnenschein Mark F | Capped polyester polyol lubricant composition |
| US8419968B2 (en) | 2008-11-13 | 2013-04-16 | Chemtura Corporation | Lubricants for refrigeration systems |
| CA2748618C (en) | 2008-12-31 | 2016-06-07 | Battelle Memorial Institute | Solvent-less preparation of polyols by ozonolysis |
| BRPI0923798B1 (pt) | 2008-12-31 | 2020-04-14 | Battelle Memorial Institute | métodos para produzir um éster e para produzir amidas |
| BRPI0923833B1 (pt) | 2008-12-31 | 2020-04-14 | Battelle Memorial Institute | métodos para produzir um éster e amidas |
| JP6075952B2 (ja) * | 2008-12-31 | 2017-02-08 | バテル・メモリアル・インスティテュートＢａｔｔｅｌｌｅ Ｍｅｍｏｒｉａｌ Ｉｎｓｔｉｔｕｔｅ | 最初の脂肪酸の酸化的開裂と次のエステル化反応によるエステルとポリオールの製造 |
| CN103695129B (zh) | 2009-01-26 | 2017-01-18 | 科聚亚公司 | 包含多醇酯润滑剂的工作流体 |
| DE102009042522A1 (de) * | 2009-09-22 | 2011-04-07 | Clariant International Ltd. | Kontinuierliches Umesterungsverfahren |
| CN102010772A (zh) | 2010-12-01 | 2011-04-13 | 中国科学院新疆理化技术研究所 | 哑铃型结构酯类润滑基础油及其制备方法 |
| MY171087A (en) | 2012-02-28 | 2019-09-24 | Petroliam Nasional Berhad | Method for the production of polyols and uses thereof |
| MY165638A (en) | 2012-02-28 | 2018-04-18 | Petroliam Nasional Berhad Petronas | Lubricant composition of matter and methods of preparation |
| CN104271546B (zh) | 2012-02-28 | 2017-06-09 | 马来西亚国家石油公司 | 酯的生产方法及其用途 |
| JP6265919B2 (ja) * | 2012-02-28 | 2018-01-24 | ペトロリアム ナショナル ブルハドＰｅｔｒｏｌｉａｍ Ｎａｓｉｏｎａｌ Ｂｅｒｈａｄ | バイオ潤滑剤およびバイオポリマーのためのバイオポリオール類、およびそれらの生成方法 |
| KR102212416B1 (ko) | 2012-02-28 | 2021-02-05 | 페트롤리암 내셔널 버하드 (페트로나스) | 폴리우레탄 적용을 위한 폴리올의 조성물 |
| MY169226A (en) | 2013-02-28 | 2019-03-19 | Petroliam Nasional Berhad | Preparation of biopolyol esters for lubricant application |
-
2013
- 2013-02-28 JP JP2014559855A patent/JP6265919B2/ja active Active
- 2013-02-28 MY MYPI2014002502A patent/MY186982A/en unknown
- 2013-02-28 KR KR1020147027198A patent/KR102061375B1/ko active Active
- 2013-02-28 SG SG11201405261TA patent/SG11201405261TA/en unknown
- 2013-02-28 EP EP13755362.4A patent/EP2819990B1/en active Active
- 2013-02-28 US US14/381,564 patent/US9302976B2/en active Active
- 2013-02-28 WO PCT/MY2013/000042 patent/WO2013129911A1/en not_active Ceased
- 2013-02-28 CN CN201380022544.1A patent/CN104302614B/zh active Active
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2017
- 2017-10-04 JP JP2017194379A patent/JP6524171B2/ja active Active
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