CA2867698C - Guerbet alcohols and methods for preparing and using same - Google Patents
Guerbet alcohols and methods for preparing and using same Download PDFInfo
- Publication number
- CA2867698C CA2867698C CA2867698A CA2867698A CA2867698C CA 2867698 C CA2867698 C CA 2867698C CA 2867698 A CA2867698 A CA 2867698A CA 2867698 A CA2867698 A CA 2867698A CA 2867698 C CA2867698 C CA 2867698C
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- formula
- compound
- aldehyde
- ozonolysis
- 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.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/125—Monohydroxylic acyclic alcohols containing five to twenty-two carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/40—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with ozone; by ozonolysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261613867P | 2012-03-21 | 2012-03-21 | |
| US61/613,867 | 2012-03-21 | ||
| US201261641742P | 2012-05-02 | 2012-05-02 | |
| US61/641,742 | 2012-05-02 | ||
| US201261662639P | 2012-06-21 | 2012-06-21 | |
| US61/662,639 | 2012-06-21 | ||
| PCT/US2013/030962 WO2013142206A1 (en) | 2012-03-21 | 2013-03-13 | Guerbet alcohols and methods for preparing and using same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2867698A1 CA2867698A1 (en) | 2013-09-26 |
| CA2867698C true CA2867698C (en) | 2020-07-07 |
Family
ID=49223214
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2867698A Active CA2867698C (en) | 2012-03-21 | 2013-03-13 | Guerbet alcohols and methods for preparing and using same |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9840449B2 (https=) |
| EP (1) | EP2828231B1 (https=) |
| JP (2) | JP6510400B2 (https=) |
| CA (1) | CA2867698C (https=) |
| WO (1) | WO2013142206A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6687547B2 (ja) | 2014-06-20 | 2020-04-22 | ピー2 サイエンス,インコーポレイティド | 管式又は多管式反応器における膜オゾン分解 |
| EP3440045B1 (en) | 2016-03-04 | 2025-08-20 | University of Pittsburgh- Of the Commonwealth System of Higher Education | Prevention, treatment and reversal of disease using therapeutically effective amounts of dicarboxylic acid compounds |
| EP3866968A4 (en) | 2018-10-19 | 2022-07-27 | P2 Science, Inc. | NEW METHODS FOR THE DISPROPORTIONATION DETERRENCE OF OZONIDES |
| CN113906007A (zh) * | 2019-03-26 | 2022-01-07 | 银杏生物制品公司 | 10-亚甲基脂质的衍生物,该类衍生物的制备方法及其用途 |
| JP7698668B2 (ja) * | 2020-05-29 | 2025-06-25 | ダウ グローバル テクノロジーズ エルエルシー | 混合c8~c18アルコールを含む組成物及びその界面活性剤 |
| EP4549622A1 (en) * | 2023-10-31 | 2025-05-07 | Basf Se | Hydrogenation of carbonyl compounds using hydrogen with low deuterium content |
| EP4549617A1 (en) * | 2023-10-31 | 2025-05-07 | Basf Se | Preparation of saturated or ethylenically unsaturated (cyclo)aliphatic compounds by hydrogenation of ethylenically or acetylenically unsaturated (cyclo)aliphatic compounds using hydrogen with low deuterium content |
Family Cites Families (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2813113A (en) | 1953-05-07 | 1957-11-12 | Emery Industries Inc | Method of making azelaic acid |
| US2875241A (en) | 1955-12-27 | 1959-02-24 | Monsanto Chemicals | New polyhydroxy alcohols and polyesters and novel process of preparing such compounds |
| US3119880A (en) | 1961-05-29 | 1964-01-28 | Gulf Research Development Co | Condensation of alcohols |
| DE1223822B (de) | 1965-01-27 | 1966-09-01 | Deutsche Erdoel Ag | Verfahren zur Herstellung von beta-verzweigten, gesaettigten und ungesaettigten Aldehyden |
| US3864407A (en) | 1973-06-06 | 1975-02-04 | Continental Oil Co | Catalytic Process For Producing Higher Molecular Weight |
| US3979466A (en) | 1973-06-06 | 1976-09-07 | Continental Oil Company | Process for condensation of alcohols |
| US4426542A (en) | 1981-04-22 | 1984-01-17 | Monsanto Company | Synthesis of plasticizer and detergent alcohols |
| US4425458A (en) | 1982-04-09 | 1984-01-10 | Henkel Corporation | Polyguerbet alcohol esters |
| US4540828A (en) | 1982-06-01 | 1985-09-10 | Vista Chemical Company | Catalysts for alkoxylation reactions |
| CA1197832A (en) | 1982-06-01 | 1985-12-10 | Kang Yang | Catalysts for alkoxylation reactions |
| DE3440620A1 (de) | 1984-11-07 | 1986-05-07 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung von (omega)-funktionalisierten aldehyden durch reduktive ozonolyse von ungesaettigten fettsaeureestern bzw. ungesaettigten fettalkoholen |
| US4731190A (en) | 1987-02-06 | 1988-03-15 | Alkaril Chemicals Inc. | Alkoxylated guerbet alcohols and esters as metal working lubricants |
| US4830769A (en) | 1987-02-06 | 1989-05-16 | Gaf Corporation | Propoxylated guerbet alcohols and esters thereof |
| US4767815A (en) | 1987-11-09 | 1988-08-30 | Gaf Corporation | Guerbet alcohol esters |
| US4800077A (en) | 1988-01-13 | 1989-01-24 | Gaf Corporation | Guerbet quaternary compounds |
| JP2824060B2 (ja) | 1988-04-20 | 1998-11-11 | 株式会社クラレ | 1,1,7−トリメチロールヘプタン |
| US5264006A (en) | 1990-03-20 | 1993-11-23 | Exxon Research And Engineering Co. | Guerbet alkyl ether mono amines |
| US5094667A (en) | 1990-03-20 | 1992-03-10 | Exxon Research And Engineering Company | Guerbet alkyl ether mono amines |
| DE4040154A1 (de) | 1990-12-15 | 1992-06-17 | Henkel Kgaa | Guerbetcarbonate |
| US5312968A (en) | 1993-09-07 | 1994-05-17 | Siltech Inc. | Fluorine containing guerbet citrate esters |
| US5488121A (en) | 1994-10-31 | 1996-01-30 | Siltech Inc. | Di-guerbet esters |
| US5744626A (en) | 1994-10-31 | 1998-04-28 | Lambent Technologies Inc | Complex guerbet acid esters |
| US5717119A (en) | 1994-10-31 | 1998-02-10 | Lambent Technologies Inc. | Polyoxyalkylene glycol guerbet esters |
| US5646321A (en) | 1995-08-17 | 1997-07-08 | Siltech Inc. | Guerbet meadowfoam esters |
| EG22088A (en) | 1996-04-16 | 2002-07-31 | Procter & Gamble | Alkoxylated sulfates |
| PH11997056158B1 (en) | 1996-04-16 | 2001-10-15 | Procter & Gamble | Mid-chain branched primary alkyl sulphates as surfactants |
| US6093856A (en) | 1996-11-26 | 2000-07-25 | The Procter & Gamble Company | Polyoxyalkylene surfactants |
| US6287431B1 (en) | 1997-03-21 | 2001-09-11 | Lynntech International, Ltd. | Integrated ozone generator system |
| US5756785A (en) | 1997-03-21 | 1998-05-26 | Lambent Technologies, Inc. | Guerbet betaines |
| US5786389A (en) | 1997-12-28 | 1998-07-28 | Lambert Technologies Inc. | Guerbet castor esters |
| US5929263A (en) | 1998-06-17 | 1999-07-27 | Lambent Technologies Inc | Guerbet branched quaternary compounds |
| US6013813A (en) | 1998-06-17 | 2000-01-11 | Hansotech Inc | Guerbet based sorbitan esters |
| US5919959A (en) | 1998-06-18 | 1999-07-06 | Lambent Tech Inc | Guerbet branched amine oxides |
| US5919743A (en) | 1998-12-28 | 1999-07-06 | Petroferm Inc. | Guerbet branched quaternary compounds in personal care applications |
| ATE284856T1 (de) | 1999-06-18 | 2005-01-15 | Cambridge Biopolymers Ltd | Oxidative spaltung ungesättigter öle sowie daraus hergestellte produkte |
| JP2001340763A (ja) | 2000-06-05 | 2001-12-11 | Nippon Shokubai Co Ltd | 気相オゾンによる触媒の活性化方法 |
| US20020061566A1 (en) | 2000-03-20 | 2002-05-23 | Eirich L. Dudley | Biooxidation capabilities of candida sp |
| JP3986962B2 (ja) | 2000-12-12 | 2007-10-03 | リンテック インターナショナル リミテッド | 後退可能な電極を有する電気化学装置 |
| DE10232458A1 (de) | 2002-07-17 | 2003-07-03 | Sasol Germany Gmbh | Verfahren zur Herstellung von Guerbet-Säuren |
| JP4826709B2 (ja) | 2004-03-16 | 2011-11-30 | 三菱化学株式会社 | 精製アルコールの製造方法 |
| HU227638B1 (en) * | 2005-12-23 | 2011-10-28 | Thales Rt | Flowing laboratorial ozonizating apparatus and method for ozonization reaction |
| JP4835228B2 (ja) | 2006-03-29 | 2011-12-14 | 三菱化学株式会社 | アルデヒドの製造方法 |
| DE102006021438A1 (de) | 2006-05-09 | 2007-11-15 | Cognis Ip Management Gmbh | Verfahren zur Ozonolyse von ungesättigten Verbindungen |
| FR2911135B1 (fr) | 2007-01-09 | 2009-03-20 | Diverchim Sa | Nouveau procede de preparation d'hydroxy-acides gras insatures |
| JP5344468B2 (ja) | 2008-08-13 | 2013-11-20 | 国立大学法人愛媛大学 | アルドール縮合化合物の製造方法 |
| JP5033829B2 (ja) | 2008-08-27 | 2012-09-26 | 株式会社神鋼環境ソリューション | 消化ガスの脱酸素方法及び装置 |
| KR101206214B1 (ko) | 2009-01-16 | 2012-12-03 | 주식회사 엘지화학 | 올레핀으로부터의 알코올을 제조하는 시스템 |
| ES2621807T3 (es) | 2009-11-06 | 2017-07-05 | Cognis Ip Management Gmbh | Procedimiento para la preparación de alcoholes de Guerbet |
| DE102010026196A1 (de) | 2010-06-25 | 2011-12-29 | Evonik Degussa Gmbh | Synthese von omega-Aminocarbonsäuren und deren Estern aus ungesättigten Fettsäurederivaten |
| US8840705B2 (en) | 2011-07-07 | 2014-09-23 | Linde Aktiengesellschaft | Methods for the ozonolysis of organic compounds |
| WO2014015290A1 (en) | 2012-07-19 | 2014-01-23 | P2 Science, Inc. | Ozonolysis operations for generation of reduced and/or oxidized product streams |
-
2013
- 2013-03-13 WO PCT/US2013/030962 patent/WO2013142206A1/en not_active Ceased
- 2013-03-13 US US13/801,209 patent/US9840449B2/en active Active
- 2013-03-13 CA CA2867698A patent/CA2867698C/en active Active
- 2013-03-13 EP EP13764490.2A patent/EP2828231B1/en active Active
- 2013-03-13 JP JP2015501761A patent/JP6510400B2/ja not_active Expired - Fee Related
-
2017
- 2017-12-15 JP JP2017240485A patent/JP6591518B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2015510932A (ja) | 2015-04-13 |
| WO2013142206A1 (en) | 2013-09-26 |
| JP6510400B2 (ja) | 2019-05-08 |
| EP2828231A4 (en) | 2015-06-24 |
| EP2828231A1 (en) | 2015-01-28 |
| US20130274511A1 (en) | 2013-10-17 |
| CA2867698A1 (en) | 2013-09-26 |
| JP2018052975A (ja) | 2018-04-05 |
| EP2828231B1 (en) | 2019-11-06 |
| JP6591518B2 (ja) | 2019-10-16 |
| US9840449B2 (en) | 2017-12-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20180308 |
|
| H11 | Ip right ceased following rejected request for revival |
Free format text: ST27 STATUS EVENT CODE: T-6-6-H10-H11-H101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: TIME LIMIT FOR REVERSAL EXPIRED Effective date: 20250915 |
|
| H13 | Ip right lapsed |
Free format text: ST27 STATUS EVENT CODE: N-4-6-H10-H13-H100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE AND LATE FEE NOT PAID BY DEADLINE OF NOTICE Effective date: 20251106 |
|
| W00 | Other event occurred |
Free format text: ST27 STATUS EVENT CODE: N-6-6-W10-W00-W100 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: LETTER SENT Effective date: 20251107 |