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 (https=) | 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 (https=) |
| EP (1) | EP2819990B1 (https=) |
| JP (2) | JP6265919B2 (https=) |
| KR (1) | KR102061375B1 (https=) |
| CN (1) | CN104302614B (https=) |
| MY (1) | MY186982A (https=) |
| SG (1) | SG11201405261TA (https=) |
| WO (1) | WO2013129911A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013129911A1 (en) * | 2012-02-28 | 2013-09-06 | Petroliam Nasional Berhad | Bio-polyols for bio-lubricant and bio-polymer and methods for the preparation thereof |
| SG11201405265QA (en) * | 2012-02-28 | 2014-09-26 | Petroliam Nasional Berhad | Method for the production of esters and uses thereof |
| EP2819987B1 (en) | 2012-02-28 | 2020-12-23 | Petroliam Nasional Berhad | Lubricant composition of matter and methods of preparation |
| DK2820112T3 (en) | 2012-02-28 | 2017-09-11 | Petroliam Nasional Berhad | PROCEDURE FOR PREPARING POLYOLS AND APPLICATIONS THEREOF |
| CN107056609A (zh) | 2012-02-28 | 2017-08-18 | 马来西亚国家石油公司 | 用于聚氨酯应用的物质多元醇的组合物 |
| 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 |
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| US2997493A (en) | 1959-09-29 | 1961-08-22 | Procter & Gamble | Method for preparing straight chain hexitol fatty esters |
| FR2254633B1 (https=) | 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 |
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| JPS57185235A (en) * | 1981-05-07 | 1982-11-15 | Mitsui Toatsu Chem Inc | Preparation of neopentyl polyol ester from fatty acid |
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| BRPI0923801B1 (pt) | 2008-12-31 | 2020-10-13 | Battelle Memorial Institute | Métodos para produzir um éster, e para produzir amidas |
| MX2011007002A (es) | 2008-12-31 | 2012-09-28 | Battelle Memorial Institute | Pre-esterificacion de polioles primarios para mejorar la solubilidad en solventes usados en el proceso de poliol. |
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| 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 |
| EP2819987B1 (en) | 2012-02-28 | 2020-12-23 | Petroliam Nasional Berhad | Lubricant composition of matter and methods of preparation |
| WO2013129911A1 (en) | 2012-02-28 | 2013-09-06 | Petroliam Nasional Berhad | Bio-polyols for bio-lubricant and bio-polymer and methods for the preparation thereof |
| CN107056609A (zh) | 2012-02-28 | 2017-08-18 | 马来西亚国家石油公司 | 用于聚氨酯应用的物质多元醇的组合物 |
| SG11201405265QA (en) * | 2012-02-28 | 2014-09-26 | Petroliam Nasional Berhad | Method for the production of esters and uses thereof |
| DK2820112T3 (en) | 2012-02-28 | 2017-09-11 | Petroliam Nasional Berhad | PROCEDURE FOR PREPARING POLYOLS AND APPLICATIONS THEREOF |
| MY169226A (en) | 2013-02-28 | 2019-03-19 | Petroliam Nasional Berhad | Preparation of biopolyol esters for lubricant application |
-
2013
- 2013-02-28 WO PCT/MY2013/000042 patent/WO2013129911A1/en not_active Ceased
- 2013-02-28 EP EP13755362.4A patent/EP2819990B1/en active Active
- 2013-02-28 SG SG11201405261TA patent/SG11201405261TA/en unknown
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