JP2015508814A5 - - Google Patents
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- Publication number
- JP2015508814A5 JP2015508814A5 JP2014559853A JP2014559853A JP2015508814A5 JP 2015508814 A5 JP2015508814 A5 JP 2015508814A5 JP 2014559853 A JP2014559853 A JP 2014559853A JP 2014559853 A JP2014559853 A JP 2014559853A JP 2015508814 A5 JP2015508814 A5 JP 2015508814A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- ester
- polyol
- ester polyol
- ozone
- 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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- 229920005862 polyol Polymers 0.000 claims 76
- -1 ester polyol ester Chemical class 0.000 claims 64
- 238000000034 method Methods 0.000 claims 37
- 239000000203 mixture Substances 0.000 claims 29
- 150000002763 monocarboxylic acids Chemical class 0.000 claims 22
- 239000002253 acid Substances 0.000 claims 21
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims 20
- 235000014113 dietary fatty acids Nutrition 0.000 claims 16
- 229930195729 fatty acid Natural products 0.000 claims 16
- 239000000194 fatty acid Substances 0.000 claims 16
- 150000004665 fatty acids Chemical class 0.000 claims 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 16
- 150000003077 polyols Chemical class 0.000 claims 16
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 125000004432 carbon atom Chemical group C* 0.000 claims 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 12
- 239000011541 reaction mixture Substances 0.000 claims 12
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 10
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims 10
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims 10
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 10
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims 10
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 9
- 239000000314 lubricant Substances 0.000 claims 9
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 8
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 claims 8
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 8
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims 8
- 150000001735 carboxylic acids Chemical class 0.000 claims 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 8
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims 8
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims 8
- 235000013772 propylene glycol Nutrition 0.000 claims 8
- 239000002199 base oil Substances 0.000 claims 7
- 125000003158 alcohol group Chemical group 0.000 claims 6
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims 5
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims 5
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 claims 5
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims 5
- 239000005639 Lauric acid Substances 0.000 claims 5
- 235000021314 Palmitic acid Nutrition 0.000 claims 5
- 235000021355 Stearic acid Nutrition 0.000 claims 5
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims 5
- 125000002843 carboxylic acid group Chemical group 0.000 claims 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 5
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 5
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 5
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 5
- 235000019260 propionic acid Nutrition 0.000 claims 5
- 239000008117 stearic acid Substances 0.000 claims 5
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims 5
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N Nonanedioid acid Natural products OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims 4
- 229940105990 diglycerin Drugs 0.000 claims 4
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims 4
- 235000011187 glycerol Nutrition 0.000 claims 4
- 239000000600 sorbitol Substances 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 3
- 150000007513 acids Chemical class 0.000 claims 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims 1
- 235000019737 Animal fat Nutrition 0.000 claims 1
- 239000005642 Oleic acid Substances 0.000 claims 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 230000001588 bifunctional effect Effects 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims 1
- 239000010687 lubricating oil Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-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 |
|---|---|---|---|
| US201261604301P | 2012-02-28 | 2012-02-28 | |
| US61/604,301 | 2012-02-28 | ||
| PCT/MY2013/000040 WO2013129909A1 (en) | 2012-02-28 | 2013-02-28 | Lubricant composition of matter and methods of preparation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015508814A JP2015508814A (ja) | 2015-03-23 |
| JP2015508814A5 true JP2015508814A5 (enExample) | 2015-12-24 |
| JP6133908B2 JP6133908B2 (ja) | 2017-05-24 |
Family
ID=49083018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014559853A Active JP6133908B2 (ja) | 2012-02-28 | 2013-02-28 | 潤滑油の物質組成および生成方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US10131616B2 (enExample) |
| EP (1) | EP2819987B1 (enExample) |
| JP (1) | JP6133908B2 (enExample) |
| KR (1) | KR102061376B1 (enExample) |
| CN (1) | CN104302612B (enExample) |
| MY (1) | MY165638A (enExample) |
| SG (1) | SG11201405268PA (enExample) |
| WO (1) | WO2013129909A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2819987B1 (en) | 2012-02-28 | 2020-12-23 | Petroliam Nasional Berhad | Lubricant composition of matter and methods of preparation |
| US10654791B2 (en) | 2012-02-28 | 2020-05-19 | Petroliam Nasional Berhad | Composition of matter polyols for polyurethane applications |
| US9302976B2 (en) | 2012-02-28 | 2016-04-05 | Petroliam Nasional Berhad | Bio-polyols for bio-lubricant and bio-polymer and methods for the preparation thereof |
| WO2013129908A1 (en) | 2012-02-28 | 2013-09-06 | Petroliam Nasional Berhad | Method for the production of polyols and uses thereof |
| JP6097771B2 (ja) * | 2012-02-28 | 2017-03-15 | ペトロリアム ナショナル ブルハドＰｅｔｒｏｌｉａｍ Ｎａｓｉｏｎａｌ Ｂｅｒｈａｄ | エステル類の製造方法およびその用途 |
| MY169226A (en) * | 2013-02-28 | 2019-03-19 | Petroliam Nasional Berhad | Preparation of biopolyol esters for lubricant application |
| JP6669343B2 (ja) * | 2015-02-27 | 2020-03-18 | 出光興産株式会社 | 生分解性潤滑油組成物 |
| CA2986040C (en) * | 2015-05-19 | 2022-05-31 | Quaker Chemical Corporation | Synthetic esters derived from high stability oleic acid |
| WO2017147708A1 (en) * | 2016-03-02 | 2017-09-08 | Trent University | Renewably derived polyesters containing branched-chain monomers and methods of making and using the same |
| CN108689841A (zh) * | 2018-07-06 | 2018-10-23 | 湖南理工学院 | 一种制备高品质季戊四醇油酸酯的方法 |
| CN109949870B (zh) * | 2019-03-07 | 2020-12-29 | 广东辛孚科技有限公司 | 一种分子级基础油调和优化方法 |
| CN110407692A (zh) * | 2019-08-05 | 2019-11-05 | 嘉兴中诚环保科技股份有限公司 | 聚己二酸丙三醇叔癸酸酯的合成方法 |
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| CN112552977A (zh) * | 2020-12-30 | 2021-03-26 | 南京威尔药业集团股份有限公司 | 一种分步反应制备合成酯基础油的方法 |
| US11845903B2 (en) * | 2021-11-02 | 2023-12-19 | ExxonMobil Technology and Engineering Company | High yield jet fuel and chemicals from ozonolysis of triglycerides |
| WO2024229029A1 (en) * | 2023-05-02 | 2024-11-07 | ExxonMobil Technology and Engineering Company | Internal combustion engine lubricant |
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| JP6097771B2 (ja) | 2012-02-28 | 2017-03-15 | ペトロリアム ナショナル ブルハドＰｅｔｒｏｌｉａｍ Ｎａｓｉｏｎａｌ Ｂｅｒｈａｄ | エステル類の製造方法およびその用途 |
| US10654791B2 (en) | 2012-02-28 | 2020-05-19 | Petroliam Nasional Berhad | Composition of matter polyols for polyurethane applications |
| WO2013129908A1 (en) | 2012-02-28 | 2013-09-06 | Petroliam Nasional Berhad | Method for the production of polyols and uses thereof |
| EP2819987B1 (en) | 2012-02-28 | 2020-12-23 | Petroliam Nasional Berhad | 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 |
-
2013
- 2013-02-28 EP EP13754711.3A patent/EP2819987B1/en active Active
- 2013-02-28 US US14/381,545 patent/US10131616B2/en active Active
- 2013-02-28 CN CN201380022561.5A patent/CN104302612B/zh active Active
- 2013-02-28 MY MYPI2013000715A patent/MY165638A/en unknown
- 2013-02-28 JP JP2014559853A patent/JP6133908B2/ja active Active
- 2013-02-28 KR KR1020147027250A patent/KR102061376B1/ko active Active
- 2013-02-28 SG SG11201405268PA patent/SG11201405268PA/en unknown
- 2013-02-28 WO PCT/MY2013/000040 patent/WO2013129909A1/en not_active Ceased
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