JP2015511954A5 - - Google Patents
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- Publication number
- JP2015511954A5 JP2015511954A5 JP2014559851A JP2014559851A JP2015511954A5 JP 2015511954 A5 JP2015511954 A5 JP 2015511954A5 JP 2014559851 A JP2014559851 A JP 2014559851A JP 2014559851 A JP2014559851 A JP 2014559851A JP 2015511954 A5 JP2015511954 A5 JP 2015511954A5
- Authority
- JP
- Japan
- Prior art keywords
- ozone
- water
- ester
- mole
- carbon
- 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
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 42
- 238000000034 method Methods 0.000 claims 40
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims 37
- -1 fatty acid ester Chemical class 0.000 claims 21
- 229920005862 polyol Polymers 0.000 claims 21
- 239000000203 mixture Substances 0.000 claims 20
- 239000000126 substance Substances 0.000 claims 20
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 19
- 239000011541 reaction mixture Substances 0.000 claims 15
- 125000005907 alkyl ester group Chemical group 0.000 claims 14
- 239000000047 product Substances 0.000 claims 14
- 238000010992 reflux Methods 0.000 claims 14
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 12
- 235000014113 dietary fatty acids Nutrition 0.000 claims 12
- 150000002148 esters Chemical class 0.000 claims 12
- 229930195729 fatty acid Natural products 0.000 claims 12
- 239000000194 fatty acid Substances 0.000 claims 12
- 238000010533 azeotropic distillation Methods 0.000 claims 8
- 150000004665 fatty acids Chemical class 0.000 claims 8
- 238000005809 transesterification reaction Methods 0.000 claims 7
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- 150000003077 polyols Chemical class 0.000 claims 5
- 238000004821 distillation Methods 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 238000005194 fractionation Methods 0.000 claims 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims 2
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 claims 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 claims 2
- 235000019737 Animal fat Nutrition 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 claims 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 claims 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims 2
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 claims 2
- 235000015112 vegetable and seed oil Nutrition 0.000 claims 2
- 239000008158 vegetable oil Substances 0.000 claims 2
- 239000005968 1-Decanol Substances 0.000 claims 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 229960000541 cetyl alcohol Drugs 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 235000019197 fats Nutrition 0.000 claims 1
- 239000006260 foam Substances 0.000 claims 1
- 235000019869 fractionated palm oil Nutrition 0.000 claims 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical group CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims 1
- 238000005949 ozonolysis reaction Methods 0.000 claims 1
- 238000000746 purification Methods 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
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261604267P | 2012-02-28 | 2012-02-28 | |
| US61/604,267 | 2012-02-28 | ||
| PCT/MY2013/000038 WO2013129907A1 (en) | 2012-02-28 | 2013-02-28 | Method for the production of esters and uses thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015511954A JP2015511954A (ja) | 2015-04-23 |
| JP2015511954A5 true JP2015511954A5 (OSRAM) | 2015-12-24 |
| JP6097771B2 JP6097771B2 (ja) | 2017-03-15 |
Family
ID=49083016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014559851A Active JP6097771B2 (ja) | 2012-02-28 | 2013-02-28 | エステル類の製造方法およびその用途 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9505701B2 (OSRAM) |
| EP (1) | EP2819985B1 (OSRAM) |
| JP (1) | JP6097771B2 (OSRAM) |
| KR (1) | KR102061374B1 (OSRAM) |
| CN (1) | CN104271546B (OSRAM) |
| MY (1) | MY174607A (OSRAM) |
| SG (1) | SG11201405265QA (OSRAM) |
| WO (1) | WO2013129907A1 (OSRAM) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2637419T3 (es) * | 2012-02-28 | 2017-10-13 | Petroliam Nasional Berhad | Procedimiento de producción de polioles y usos de los mismos |
| KR102212416B1 (ko) | 2012-02-28 | 2021-02-05 | 페트롤리암 내셔널 버하드 (페트로나스) | 폴리우레탄 적용을 위한 폴리올의 조성물 |
| 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 |
| CN104302614B (zh) * | 2012-02-28 | 2017-03-08 | 马来西亚国家石油公司 | 用于生物润滑剂和生物聚合物的生物多元醇及其制备方法 |
| WO2013129909A1 (en) | 2012-02-28 | 2013-09-06 | 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 |
| CN108164416B (zh) * | 2018-01-05 | 2021-02-19 | 浙江工业大学 | 一种基于生物柴油制备壬二酸单甲酯的新工艺 |
| 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 (50)
| 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 |
| US3048608A (en) | 1959-03-18 | 1962-08-07 | Heyden Newport Chemical Corp | Neopentyl glycol esters |
| US2997493A (en) | 1959-09-29 | 1961-08-22 | Procter & Gamble | Method for preparing straight chain hexitol fatty esters |
| FR2254633B1 (OSRAM) | 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 |
| JPH0418049A (ja) | 1990-05-09 | 1992-01-22 | Lion Corp | 不飽和脂肪酸低級アルキルエステルのオゾン化物の酸素酸化分解方法 |
| US5773256A (en) * | 1991-08-12 | 1998-06-30 | Ulice Sa | Methods for the production of esters of α-glucosides and uses thereof |
| JPH08503975A (ja) | 1992-06-03 | 1996-04-30 | ヘンケル・コーポレイション | 冷媒の熱媒液用ポリオールエステル潤滑剤 |
| IT1254974B (it) | 1992-06-18 | 1995-10-11 | Bayer Italia Spa | Granulati compositi, scorrevoli,idrofobi,un procedimento per la loro preparazione nonche' loro impiego |
| US5362368A (en) | 1993-06-03 | 1994-11-08 | Scott Lynn | Chlorine generator |
| BR9504838A (pt) | 1994-11-15 | 1997-10-07 | Lubrizol Corp | Ester de poliol composição de óleo lubrificante |
| FI104553B (fi) | 1997-05-07 | 2000-02-29 | Fortum Oil & Gas Oy | Menetelmä kompleksiesterien valmistamiseksi ja puhdistamiseksi |
| 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 |
| JP4702052B2 (ja) | 2003-03-31 | 2011-06-15 | 新日本理化株式会社 | 潤滑油及び潤滑方法 |
| 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 |
| EP1861351A2 (en) | 2005-02-28 | 2007-12-05 | Michigan State University | Novel triglycerides and method of preparation thereof |
| EP2308955B1 (en) * | 2005-04-26 | 2017-02-22 | Battelle Memorial Institute | Methods for production of polyols from oils and their use in the production of polyesters and polyurethanes |
| JP4633765B2 (ja) | 2006-06-07 | 2011-02-16 | 花王株式会社 | エステルの製造方法 |
| AU2007301112A1 (en) | 2006-09-27 | 2008-04-03 | Asahi Glass Company, Limited | Method for producing soft polyurethane foam |
| JP2010523797A (ja) | 2007-04-09 | 2010-07-15 | ダウ グローバル テクノロジーズ インコーポレイティド | キャップ化ポリエステルポリオール潤滑剤組成物 |
| CN101077856B (zh) | 2007-06-26 | 2011-06-08 | 上海大学 | 固体酸催化制备壬二酸的方法 |
| JP5327684B2 (ja) | 2008-06-03 | 2013-10-30 | ダウ グローバル テクノロジーズ エルエルシー | 複合分散液、その製造方法、及びそれから製造された物品 |
| US8419968B2 (en) | 2008-11-13 | 2013-04-16 | Chemtura Corporation | Lubricants for refrigeration systems |
| EP2382293B1 (en) | 2008-12-31 | 2019-01-16 | 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 |
| CN102333755B (zh) | 2008-12-31 | 2016-02-24 | 巴特尔纪念研究院 | 通过初始的脂肪酸氧化分解后的酯化反应制备酯和多元醇 |
| EP2382294B1 (en) | 2008-12-31 | 2019-02-13 | Battelle Memorial Institute | Use of fatty acids as feed material in polyol process |
| CN102292420A (zh) | 2009-01-26 | 2011-12-21 | 科聚亚公司 | 用于冷冻体系的多醇酯润滑剂的制备 |
| DE102009042522A1 (de) | 2009-09-22 | 2011-04-07 | Clariant International Ltd. | Kontinuierliches Umesterungsverfahren |
| CN101812349B (zh) | 2010-05-11 | 2013-05-01 | 上海海都化学科技有限公司 | 润滑油及润滑脂基础油及其制备方法与应用 |
| 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 |
| 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 |
| ES2637419T3 (es) | 2012-02-28 | 2017-10-13 | Petroliam Nasional Berhad | Procedimiento de producción de polioles y usos de los mismos |
| KR102212416B1 (ko) | 2012-02-28 | 2021-02-05 | 페트롤리암 내셔널 버하드 (페트로나스) | 폴리우레탄 적용을 위한 폴리올의 조성물 |
| WO2013129909A1 (en) | 2012-02-28 | 2013-09-06 | Petroliam Nasional Berhad | Lubricant composition of matter and methods of preparation |
| CN104302614B (zh) | 2012-02-28 | 2017-03-08 | 马来西亚国家石油公司 | 用于生物润滑剂和生物聚合物的生物多元醇及其制备方法 |
| MY169226A (en) | 2013-02-28 | 2019-03-19 | Petroliam Nasional Berhad | Preparation of biopolyol esters for lubricant application |
-
2013
- 2013-02-28 JP JP2014559851A patent/JP6097771B2/ja active Active
- 2013-02-28 KR KR1020147027181A patent/KR102061374B1/ko active Active
- 2013-02-28 SG SG11201405265QA patent/SG11201405265QA/en unknown
- 2013-02-28 MY MYPI2014002503A patent/MY174607A/en unknown
- 2013-02-28 WO PCT/MY2013/000038 patent/WO2013129907A1/en not_active Ceased
- 2013-02-28 US US14/381,530 patent/US9505701B2/en active Active
- 2013-02-28 EP EP13755664.3A patent/EP2819985B1/en active Active
- 2013-02-28 CN CN201380022538.6A patent/CN104271546B/zh active Active
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