JP2013537536A5 - - Google Patents
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- Publication number
- JP2013537536A5 JP2013537536A5 JP2013523314A JP2013523314A JP2013537536A5 JP 2013537536 A5 JP2013537536 A5 JP 2013537536A5 JP 2013523314 A JP2013523314 A JP 2013523314A JP 2013523314 A JP2013523314 A JP 2013523314A JP 2013537536 A5 JP2013537536 A5 JP 2013537536A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl levulinate
- ketal
- product
- propylene glycol
- composition
- 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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 84
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 60
- GMEONFUTDYJSNV-UHFFFAOYSA-N Ethyl levulinate Chemical compound CCOC(=O)CCC(C)=O GMEONFUTDYJSNV-UHFFFAOYSA-N 0.000 claims 49
- 239000000047 product Substances 0.000 claims 32
- 239000000203 mixture Substances 0.000 claims 30
- 238000006243 chemical reaction Methods 0.000 claims 16
- 239000000356 contaminant Substances 0.000 claims 16
- 239000002253 acid Substances 0.000 claims 10
- 239000006227 byproduct Substances 0.000 claims 10
- 238000000034 method Methods 0.000 claims 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 10
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 claims 8
- 238000004821 distillation Methods 0.000 claims 6
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims 5
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical group C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims 4
- 239000003377 acid catalyst Substances 0.000 claims 4
- 239000000539 dimer Substances 0.000 claims 4
- 239000002994 raw material Substances 0.000 claims 4
- 239000013638 trimer Substances 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- 238000005194 fractionation Methods 0.000 claims 3
- 238000000769 gas chromatography-flame ionisation detection Methods 0.000 claims 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- 229940040102 levulinic acid Drugs 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 238000004064 recycling Methods 0.000 claims 2
- 241000894007 species Species 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 230000003796 beauty Effects 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 238000012423 maintenance Methods 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- AALKGALVYCZETF-UHFFFAOYSA-N pentane-1,2,3-triol Chemical compound CCC(O)C(O)CO AALKGALVYCZETF-UHFFFAOYSA-N 0.000 claims 1
- XLMFDCKSFJWJTP-UHFFFAOYSA-N pentane-2,3-diol Chemical compound CCC(O)C(C)O XLMFDCKSFJWJTP-UHFFFAOYSA-N 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37036510P | 2010-08-03 | 2010-08-03 | |
| US61/370,365 | 2010-08-03 | ||
| PCT/US2011/046463 WO2012018939A2 (en) | 2010-08-03 | 2011-08-03 | Methods for the manufacture of acetals and ketals, and the acetals and ketals produced thereby |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013537536A JP2013537536A (ja) | 2013-10-03 |
| JP2013537536A5 true JP2013537536A5 (enExample) | 2014-09-18 |
| JP5886856B2 JP5886856B2 (ja) | 2016-03-16 |
Family
ID=45556606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013523314A Active JP5886856B2 (ja) | 2010-08-03 | 2011-08-03 | アセタールおよびケタールの製造方法、ならびにこの方法により製造されるアセタールおよびケタール |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US20120035376A1 (enExample) |
| EP (1) | EP2601184B1 (enExample) |
| JP (1) | JP5886856B2 (enExample) |
| KR (1) | KR20130136955A (enExample) |
| CN (1) | CN103025720B (enExample) |
| AU (1) | AU2011285715B2 (enExample) |
| BR (1) | BR112013000575A2 (enExample) |
| CA (2) | CA3051232C (enExample) |
| MX (1) | MX336783B (enExample) |
| SG (1) | SG187044A1 (enExample) |
| WO (1) | WO2012018939A2 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2011289224B2 (en) * | 2010-08-12 | 2015-04-16 | Gfbiochemicals Limited | Carboxy ester ketal removal compositions, methods of manufacture, and uses thereof |
| BR112013011149A2 (pt) | 2010-11-11 | 2016-08-02 | Segetis Inc | adutos poliacetal, métodos de fabricação e seus usos. |
| EP2638037A4 (en) * | 2010-11-11 | 2015-02-18 | Segetis Inc | POLY-HYDROXYKETALESTER ADDUCTS, MANUFACTURING METHOD AND USES THEREOF |
| ITPN20130066A1 (it) | 2013-11-11 | 2015-05-12 | Fluos S A S Di Giuseppe Chiaradia & C | Plastificanti per polimeri |
| US9951171B2 (en) | 2014-08-20 | 2018-04-24 | Resinate Materials Group, Inc. | Polyester polyols from recycled polymers and waste streams |
| WO2016028841A1 (en) | 2014-08-20 | 2016-02-25 | Resinate Materials Group, Inc. | Digestion of keratin |
| US9850400B2 (en) | 2014-08-20 | 2017-12-26 | Resinate Materials Group, Inc. | Digestion of keratin |
| US9580546B2 (en) | 2014-10-29 | 2017-02-28 | Resinate Materials Group, Inc. | Polymeric plasticizer compositions |
| US9890243B2 (en) | 2014-10-29 | 2018-02-13 | Resinate Materials Group, Inc. | Polymeric plasticizer compositions |
| CN110078701A (zh) * | 2019-03-29 | 2019-08-02 | 郑州大学 | 一种农林废弃物制备生物质基缩酮酯的方法 |
| US10773192B1 (en) * | 2019-04-09 | 2020-09-15 | Bitfury Ip B.V. | Method and apparatus for recovering dielectric fluids used for immersion cooling |
| CN113929654B (zh) * | 2021-10-26 | 2022-09-02 | 郑州大学 | 一种乙酰丙酸甘油缩酮甲酯的连续合成方法及应用 |
| CN120282956A (zh) | 2022-12-02 | 2025-07-08 | 法国特种经营公司 | 生物基化合物 |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1934309A (en) | 1933-11-07 | Cyclic acetals and process of | ||
| US2556135A (en) | 1951-06-05 | Preparation of ketal esters | ||
| US2260261A (en) | 1941-10-21 | Cyclic ketals and process for | ||
| US2008720A (en) | 1932-05-03 | 1935-07-23 | Du Pont | Levulinic acid ester |
| US2654723A (en) | 1950-11-01 | 1953-10-06 | Gen Tire & Rubber Co | Polyvinyl composition and method of making same |
| FR1445013A (fr) | 1964-07-09 | 1966-07-08 | Thomae Gmbh Dr K | Procédé pour fabriquer des nouveaux acides dioxolano-2-carboxyliques |
| US3658789A (en) | 1970-01-19 | 1972-04-25 | Syntex Corp | Drug glycerol ketals |
| GB1427918A (en) | 1972-05-26 | 1976-03-10 | Shell Int Research | Herbicidal glycerol acetals |
| SU722912A1 (ru) | 1978-03-06 | 1980-03-25 | Уфимский Нефтяной Институт | Способ получени 5-метил/-4оксо3,6,8-триоксабицикло/ (3,2,1)-октана |
| JPS57197235A (en) | 1981-05-28 | 1982-12-03 | Kao Corp | Preparation of 2-hydroxy-3-alkoxypropyl glyceryl ether |
| US4792411A (en) | 1986-12-29 | 1988-12-20 | The Lubrizol Corporation | Dioxolanes and thio analogs, derivatives thereof and lubricants and fuels containing same |
| US4923891A (en) | 1987-09-24 | 1990-05-08 | G. D. Searle & Co. | Leukotriene LTD4 and LTB4 antagonists |
| US5095098A (en) | 1989-09-29 | 1992-03-10 | E. I. Du Pont De Nemours And Company | Yttrium and rare earth compounds catalyzed lactone polymerization |
| JPH04217972A (ja) | 1990-07-30 | 1992-08-07 | Mitsuo Okahara | 新規なカルボン酸塩誘導体及びそれよりなる分解性界面活性剤 |
| DE4110973A1 (de) | 1991-04-05 | 1992-10-08 | Haarmann & Reimer Gmbh | Mittel mit physiologischem kuehleffekt und fuer diese mittel geeignete wirksame verbindungen |
| JP2848706B2 (ja) | 1992-11-25 | 1999-01-20 | ユニリーバー・ナームローゼ・ベンノートシヤープ | アルキリデングリセロール界面活性剤およびそれを含む洗剤組成物 |
| US5202413A (en) | 1993-02-16 | 1993-04-13 | E. I. Du Pont De Nemours And Company | Alternating (ABA)N polylactide block copolymers |
| DE19647395A1 (de) | 1996-11-15 | 1998-05-20 | Basf Ag | Verfahren zur Herstellung von cyclischen Acetalen oder Ketalen |
| US5998092A (en) | 1998-05-27 | 1999-12-07 | Clariant International, Ltd. | Water soluble negative-working photoresist composition |
| JP4287546B2 (ja) | 1999-07-27 | 2009-07-01 | 花王株式会社 | グリセリルエーテルの製法 |
| EP1242500B1 (en) | 1999-12-10 | 2005-04-20 | Equipolymers GmbH | Catalyst systems for polycondensation reactions |
| US6528025B1 (en) | 2000-06-26 | 2003-03-04 | Roche Vitamins Inc. | Process of manufacturing equipment for preparing acetals and ketals |
| ES2201894B2 (es) | 2002-01-18 | 2005-03-01 | Industrial Management, S.A | Procedimiento para producir combustibles biodiesel con propiedades mejoradas a baja temperatura. |
| DE10218916A1 (de) | 2002-04-27 | 2003-11-06 | Degussa | Verfahren zur Herstellung von Acetalen und Ketalen mit Hilfe mehrstufiger Pervaporation oder Dampfpermeation |
| US7553819B2 (en) | 2003-05-12 | 2009-06-30 | Theracarb Inc. | Multivalent inhibitors of serum amyloid P component |
| EP1737810A2 (en) | 2004-03-24 | 2007-01-03 | E.I.Du pont de nemours and company | PREPARATION OF LEVULINIC ACID ESTERS FROM alpha-ANGELICA LACTONE AND ALCOHOLS |
| EP1732876A1 (en) | 2004-03-24 | 2006-12-20 | E.I.Du pont de nemours and company | Preparation of levulinic acid esters from alpha-angelica lactone and alcohols |
| JP4776303B2 (ja) | 2004-11-22 | 2011-09-21 | 独立行政法人科学技術振興機構 | 含フッ素化合物の製造方法、含フッ素化合物、含フッ素ポリマー、及び含フッ素ポリマーを用いた光学材料若しくは電気材料 |
| WO2006086634A2 (en) | 2005-02-11 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted imidazo[4,5-c] ring compounds and methods |
| US7300947B2 (en) * | 2005-07-13 | 2007-11-27 | Banyu Pharmaceutical Co., Ltd. | N-dihydroxyalkyl-substituted 2-oxo-imidazole derivatives |
| US7902410B2 (en) | 2005-11-03 | 2011-03-08 | Honeywell International Inc. | Process for the manufacture of fluorinated alkanes |
| EP1954140B1 (en) * | 2005-11-22 | 2013-05-29 | Segetis, Inc. | Glycerol levulinate ketals and their use |
| EP2150111B1 (en) | 2007-01-18 | 2016-10-19 | Evolva SA | Substituted 1,3-dioxanes useful as ppar modulators |
| DK2121576T3 (en) | 2007-02-15 | 2016-02-15 | Ct De Rech Sur Les Biotechnologies Marine | Polyunsaturated fatty acid monoglycerides, derivatives, and uses thereof |
| WO2009032905A1 (en) * | 2007-09-04 | 2009-03-12 | Segetis, Inc. | Ketal compounds from polyols and oxocarboxylates |
| EP2209770A1 (en) * | 2007-10-09 | 2010-07-28 | Segetis, Inc. | Method of making ketals and acetals |
| US8829229B2 (en) | 2008-08-25 | 2014-09-09 | Dow Global Technologies Llc | Polyol ethers and process for making them |
| CN102239156B (zh) | 2008-09-25 | 2014-10-15 | 塞格提斯有限公司 | 缩酮酯衍生物 |
| WO2011140644A1 (en) * | 2010-05-11 | 2011-11-17 | The University Of British Columbia | Polyacetal or polyketal and ether polymers |
-
2011
- 2011-08-03 SG SG2013002431A patent/SG187044A1/en unknown
- 2011-08-03 AU AU2011285715A patent/AU2011285715B2/en not_active Ceased
- 2011-08-03 CA CA3051232A patent/CA3051232C/en active Active
- 2011-08-03 CN CN201180035811.XA patent/CN103025720B/zh active Active
- 2011-08-03 US US13/197,593 patent/US20120035376A1/en not_active Abandoned
- 2011-08-03 EP EP11815279.2A patent/EP2601184B1/en active Active
- 2011-08-03 BR BR112013000575A patent/BR112013000575A2/pt not_active Application Discontinuation
- 2011-08-03 KR KR1020137000636A patent/KR20130136955A/ko not_active Withdrawn
- 2011-08-03 WO PCT/US2011/046463 patent/WO2012018939A2/en not_active Ceased
- 2011-08-03 JP JP2013523314A patent/JP5886856B2/ja active Active
- 2011-08-03 MX MX2013001158A patent/MX336783B/es active IP Right Grant
- 2011-08-03 CA CA2806352A patent/CA2806352C/en active Active
-
2014
- 2014-11-21 US US14/550,222 patent/US9593093B2/en active Active
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