JP4814794B2 - 生物学的に生産された1,3−プロパンジオールの精製 - Google Patents
生物学的に生産された1,3−プロパンジオールの精製 Download PDFInfo
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- JP4814794B2 JP4814794B2 JP2006532802A JP2006532802A JP4814794B2 JP 4814794 B2 JP4814794 B2 JP 4814794B2 JP 2006532802 A JP2006532802 A JP 2006532802A JP 2006532802 A JP2006532802 A JP 2006532802A JP 4814794 B2 JP4814794 B2 JP 4814794B2
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- propanediol
- subjecting
- ion exchange
- boiling point
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
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Landscapes
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Genetics & Genomics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| PCT/US2004/014043 WO2004101479A2 (en) | 2003-05-06 | 2004-05-05 | Purification of biologically-produced 1,3-propanediol |
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| JP2011056908A Division JP2011126911A (ja) | 2003-05-06 | 2011-03-15 | 生物学的に生産された1,3−プロパンジオール |
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| US20040225107A1 (en) * | 2003-05-06 | 2004-11-11 | Sunkara Hari Babu | Polytrimethylene ether glycol with excellent quality from biochemically-derived 1,3-propanediol |
| JP4814794B2 (ja) * | 2003-05-06 | 2011-11-16 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 生物学的に生産された1,3−プロパンジオールの精製 |
| US7888405B2 (en) | 2004-01-30 | 2011-02-15 | E. I. Du Pont De Nemours And Company | Aliphatic-aromatic polyesters, and articles made therefrom |
| US20080103217A1 (en) * | 2006-10-31 | 2008-05-01 | Hari Babu Sunkara | Polyether ester elastomer composition |
| US7396896B2 (en) * | 2004-12-21 | 2008-07-08 | E.I. Dupont De Nemours And Company | Poly(trimethylene terephthalate) composition and shaped articles prepared therefrom |
| US7629396B2 (en) * | 2005-02-23 | 2009-12-08 | E.I. Du Pont De Nemours And Company | Silicon-containing polytrimethylene homo- for copolyether composition |
| US20060189711A1 (en) * | 2005-02-23 | 2006-08-24 | Ng Howard C | Silicon-containing polytrimethylene homo- or copolyether composition |
| JP5652986B2 (ja) * | 2005-04-22 | 2015-01-14 | 三菱化学株式会社 | ポリエステルペレット及びその貯蔵方法 |
| EP3919543A3 (en) * | 2005-04-22 | 2022-03-16 | Mitsubishi Chemical Corporation | Biomass-resource-derived polyester and production process thereof |
| JP2006328377A (ja) * | 2005-04-26 | 2006-12-07 | Mitsubishi Chemicals Corp | ポリエステルペレットの貯蔵方法 |
| JP2006328378A (ja) * | 2005-04-26 | 2006-12-07 | Mitsubishi Chemicals Corp | ポリエステルの製造方法 |
| JP2006328374A (ja) * | 2005-04-26 | 2006-12-07 | Mitsubishi Chemicals Corp | ポリエステルの製造方法 |
| JP2006328370A (ja) * | 2005-04-26 | 2006-12-07 | Mitsubishi Chemicals Corp | ポリエステルの製造方法 |
| US7161045B1 (en) | 2005-08-16 | 2007-01-09 | E. I. Du Pont De Nemours And Company | Process for manufacture of polytrimethylene ether glycol |
| US7157607B1 (en) | 2005-08-16 | 2007-01-02 | E. I. Du Pont De Nemours And Company | Manufacture of polytrimethylene ether glycol |
| JP5074678B2 (ja) * | 2005-08-26 | 2012-11-14 | 株式会社堀場製作所 | 塩分ミスト除去装置およびこれを用いた分析装置 |
| US7357985B2 (en) * | 2005-09-19 | 2008-04-15 | E.I. Du Pont De Nemours And Company | High crimp bicomponent fibers |
| US20070129524A1 (en) * | 2005-12-06 | 2007-06-07 | Sunkara Hari B | Thermoplastic polyurethanes comprising polytrimethylene ether soft segments |
| US20070128459A1 (en) * | 2005-12-07 | 2007-06-07 | Kurian Joseph V | Poly(trimethylene terephthalate)/poly(alpha-hydroxy acid) films |
| US7666501B2 (en) * | 2005-12-07 | 2010-02-23 | E. I. Du Pont De Nemours And Company | Poly(trimethylene terephthalate)/poly(alpha-hydroxy acid) bi-constituent filaments |
| US20070129503A1 (en) * | 2005-12-07 | 2007-06-07 | Kurian Joseph V | Poly(trimethylene terephthalate)/poly(alpha-hydroxy acid) molded, shaped articles |
| US7164046B1 (en) | 2006-01-20 | 2007-01-16 | E. I. Du Pont De Nemours And Company | Manufacture of polytrimethylene ether glycol |
| US7388115B2 (en) * | 2006-01-20 | 2008-06-17 | E. I. Du Pont De Nemours And Company | Manufacture of polytrimethylene ether glycol |
| US20070203371A1 (en) * | 2006-01-23 | 2007-08-30 | Sunkara Hari B | Process for producing polytrimethylene ether glycol |
| TW200732292A (en) * | 2006-02-01 | 2007-09-01 | Shell Int Research | A method of treating an aldehyde mixture, use of the treated aldehyde, and an alcohol |
| US20070275139A1 (en) * | 2006-02-10 | 2007-11-29 | Melissa Joerger | Food compositions comprising renewably-based, biodegradable1,3-propanediol |
| EP1991515A4 (en) * | 2006-02-10 | 2013-03-06 | Dupont Tate & Lyle Bio Products Company Llc | BIOLOGICAL SOURCE AND ITS CONJUGATES AS NATURAL AND NON-BREATHING SOLVENTS FOR BIOMASS EXTRACTS, SCENT CONCENTRATES AND OILS |
| JP2009532506A (ja) * | 2006-02-10 | 2009-09-10 | デユポン・テイト・アンド・ライル・バイオ・プロダクツ・カンパニー・エルエルシー | 生物学的ベースの1,3−プロパンジオールのモノエステルおよびジエステルを含む組成物 |
| WO2007095255A2 (en) | 2006-02-10 | 2007-08-23 | Dupont Tate & Lyle Bio Products Company, Llc | Biodegradable compositions comprising renewably-based, biodegradable 1.3-propanediol |
| WO2007136586A2 (en) * | 2006-05-17 | 2007-11-29 | E. I. Du Pont De Nemours And Company | Personal care compositions |
| US20080039582A1 (en) * | 2006-07-28 | 2008-02-14 | Hari Babu Sunkara | Polytrimethylene ether-based polyurethane ionomers |
| JP5245227B2 (ja) * | 2006-08-23 | 2013-07-24 | 三菱瓦斯化学株式会社 | 疎水性化合物の起泡による分離法 |
| US20080175875A1 (en) * | 2006-09-25 | 2008-07-24 | Hari Babu Sunkara | Cosmetic compositions |
| MX2008012560A (es) * | 2006-10-27 | 2008-10-14 | Archer Daniels Midland Co | Procesos para aislar o purificar propilenglicol, etilenglicol y productos producidos de los mismos. |
| US7531593B2 (en) | 2006-10-31 | 2009-05-12 | E.I. Du Pont De Nemours And Company | Thermoplastic elastomer blend composition |
| US20080108845A1 (en) * | 2006-11-07 | 2008-05-08 | Hari Babu Sunkara | Polytrimethylene ether glycol esters |
| US20080176957A1 (en) * | 2006-11-15 | 2008-07-24 | Dupont Tate & Lyle Bio Products Company, Llc | Preservative compositions comprising renewably-based, biodegradable 1,3-propanediol |
| US20080135662A1 (en) * | 2006-12-06 | 2008-06-12 | Chang Jing C | Melt-spun elastoester multifilament yarns |
| US20090131625A1 (en) * | 2007-11-21 | 2009-05-21 | Kurian Joseph V | Processes for making elastomeric polyester esters from post-consumer polyester |
| CN100999742B (zh) * | 2007-01-09 | 2011-05-11 | 清华大学 | 一种发酵生产1,3-丙二醇的高产工艺 |
| US7714174B2 (en) * | 2007-03-27 | 2010-05-11 | E. I. Du Pont De Nemours And Company | Lower-color polytrimethylene ether glycol using hydride compounds |
| CN101657515B (zh) * | 2007-04-03 | 2013-04-17 | 纳幕尔杜邦公司 | 使用多元醇与离子液体的混合物的热传递体系 |
| CN101066906B (zh) * | 2007-05-24 | 2010-09-08 | 江苏汉邦科技有限公司 | 四区模拟移动床分离纯化发酵液中的1,3-丙二醇的方法 |
| WO2008156612A1 (en) * | 2007-06-15 | 2008-12-24 | Cargill, Incorporated | Process for the purification of crude glycerol compositions |
| JP2009013094A (ja) * | 2007-07-03 | 2009-01-22 | Teijin Fibers Ltd | グリコールの製造方法 |
| CN101117306B (zh) * | 2007-07-20 | 2011-01-19 | 三达膜科技(厦门)有限公司 | 一种1,3-丙二醇发酵液的除杂和脱盐方法 |
| US20090043021A1 (en) * | 2007-08-06 | 2009-02-12 | Jing-Chung Chang | Flame retardant polytrimethylene terephthalate composition |
| US20090043016A1 (en) * | 2007-08-06 | 2009-02-12 | Jing-Chung Chang | Flame retardant polytrimethylene terephthalate composition |
| US7855244B2 (en) * | 2007-08-06 | 2010-12-21 | E.I. Du Pont De Nemours And Company | Flame retardant polytrimethylene terephthalate composition |
| US20090043019A1 (en) * | 2007-08-06 | 2009-02-12 | Jing-Chung Chang | Flame retardant polytrimethylene terephthalate composition |
| US20090043017A1 (en) * | 2007-08-06 | 2009-02-12 | Jing-Chung Chang | Flame retardant polytrimethylene terephthalate composition |
| US20090054282A1 (en) * | 2007-08-24 | 2009-02-26 | E.I. Dupont De Nemours And Company | Lubrication oil compositions |
| US20090054283A1 (en) * | 2007-08-24 | 2009-02-26 | E.I. Dupont De Nemours And Company | Lubrication oil compositions |
| BRPI0815243A2 (pt) * | 2007-08-24 | 2019-09-24 | Du Pont | composição de óleo lubrificante |
| JP2010537001A (ja) * | 2007-08-24 | 2010-12-02 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 潤滑油組成物 |
| US8703681B2 (en) | 2007-08-24 | 2014-04-22 | E I Du Pont De Nemours And Company | Lubrication oil compositions |
| DE102007048277A1 (de) * | 2007-10-08 | 2009-04-09 | Agraferm Technologies Ag | Verfahren und Vorrichtung zur mikrobiellen Herstellung eines bestimmten Produktes und Methan |
| WO2009048445A2 (en) | 2007-10-09 | 2009-04-16 | E. I. Du Pont De Nemours And Company | Deodorant compositions |
| US7919017B2 (en) * | 2007-11-12 | 2011-04-05 | E. I. Du Pont De Nemours And Company | Electrical insulation fluids for use in electrical apparatus |
| EP2220018B1 (en) * | 2007-11-30 | 2012-07-04 | Metabolic Explorer | Method for purifying an alcohol from a fermentation broth |
| US20090197781A1 (en) | 2008-01-31 | 2009-08-06 | Hari Babu Sunkara | Wellbore Fluids Comprising Poly(trimethylene ether) glycol Polymers |
| JP5343628B2 (ja) * | 2008-03-04 | 2013-11-13 | 東レ株式会社 | 光透過性に優れたバイオ材料由来グリコールの製造方法及びそれから得られるポリエステルの製造方法 |
| WO2009137443A1 (en) | 2008-05-07 | 2009-11-12 | E. I. Du Pont De Nemours And Company | Plasticizers comprising poly(trimethylene ether) glycol esters |
| JP5536074B2 (ja) * | 2008-10-03 | 2014-07-02 | メタボリック エクスプローラー | 流下液膜式蒸発器、拭き取り膜式蒸発器、薄膜蒸発器、または短経路蒸発器を用いて発酵ブロスからアルコールを精製するための方法 |
| US20110172329A1 (en) * | 2008-10-16 | 2011-07-14 | E.I. Du Pont De Nemours And Company | Flame retardant poly(trimethylene terephthalate) composition |
| JP5625334B2 (ja) * | 2008-11-28 | 2014-11-19 | 東レ株式会社 | ジオールまたはトリオールの製造方法 |
| EP2358782A1 (en) | 2008-12-15 | 2011-08-24 | E. I. du Pont de Nemours and Company | Copolyesters with enhanced tear strength |
| AU2009333397A1 (en) | 2008-12-15 | 2010-07-08 | E. I. Du Pont De Nemours And Company | Copolyesters with enhanced tear strength |
| JP2012512279A (ja) | 2008-12-15 | 2012-05-31 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 脂肪族−芳香族コポリエーテルエステルの重合 |
| WO2010075023A1 (en) | 2008-12-15 | 2010-07-01 | E. I. Du Pont De Nemours And Company | Copolyesters with enhanced tear strength |
| US20100152329A1 (en) | 2008-12-17 | 2010-06-17 | E. I. Du Pont De Nemours And Company | Poly(trimethylene terephthalate) polymer blends that have reduced whitening |
| US20100152411A1 (en) | 2008-12-17 | 2010-06-17 | E.I. Du Pont De Nemours And Company | Poly(trimethylene terephthalate) with reduced whitening |
| WO2010077937A1 (en) | 2008-12-17 | 2010-07-08 | E. I. Du Pont De Nemours And Company | Reduction of whitening of poly(trimethylene terephthalate) parts by solvent exposure |
| JP5293157B2 (ja) * | 2008-12-22 | 2013-09-18 | 東レ株式会社 | ブタノールの製造方法 |
| CA2754231A1 (en) | 2009-03-03 | 2010-09-10 | E.I. Du Pont De Nemours And Company | Poly(trimethylene terephthalate) pellets with reduced oligomers and method to measure oligomer reduction |
| SG176654A1 (en) * | 2009-06-04 | 2012-01-30 | Genomatica Inc | Process of separating components of a fermentation broth |
| WO2011038178A1 (en) | 2009-09-24 | 2011-03-31 | E. I. Du Pont De Nemours And Company | Poly(hydroxyalkanoic acid) plasticized with poly(trimethylene ether) glycol |
| US20110112331A1 (en) * | 2009-11-09 | 2011-05-12 | E.I. Du Pont De Nemours And Company | Method for phase separation of polytrimethylene ether glycol in salt solution |
| WO2011062600A1 (en) | 2009-11-19 | 2011-05-26 | E. I. Du Pont De Nemours And Company | Polycondensation with a kneader reactor |
| WO2011076690A1 (en) | 2009-12-22 | 2011-06-30 | Metabolic Explorer | Method for purifying 1,2-propanediol from a fermentation broth |
| TWI500768B (zh) | 2010-07-05 | 2015-09-21 | Metabolic Explorer Sa | 由蔗糖製備1,3-丙二醇之方法 |
| CN103119142B (zh) | 2010-09-24 | 2015-12-02 | 陶氏环球技术有限责任公司 | 用于润滑剂的非芳族系抗氧化剂 |
| WO2012071241A1 (en) | 2010-11-22 | 2012-05-31 | E. I. Du Pont De Nemours And Company | Block copolymers comprising poly(1,3-trimethylene terephthalate) and poly(1,3-trimethylene 2,6-naphthalate) |
| TR201010403A2 (tr) * | 2010-12-13 | 2012-07-23 | Bsh Ev Aletleri̇ San. Ve Ti̇c. A.Ş. | BEYAZ EŞYA KAPI İÇ KASASI VE DEKORATİF DlŞ YÜZEY MESAFE ELEMANI |
| US8247526B2 (en) | 2010-12-20 | 2012-08-21 | E I Du Pont De Nemours And Company | Process for the preparation of polyalkylene ether glycol |
| KR20140052934A (ko) | 2011-02-22 | 2014-05-07 | 도레이 카부시키가이샤 | 디올 조성물 및 폴리에스테르 |
| US9018424B2 (en) | 2011-03-30 | 2015-04-28 | Toray Industries, Inc. | Method of producing diol or triol |
| US8558037B2 (en) | 2011-03-30 | 2013-10-15 | Toray Industries, Inc. | Method of producing butanol |
| WO2012130316A1 (en) | 2011-03-31 | 2012-10-04 | Metabolic Explorer | Method for purifying mpg (monopropylene glycol) from a fermentation broth |
| CN103492542B (zh) | 2011-04-13 | 2016-05-25 | Elc管理公司 | 适用于个人护理组合物的温和型阴离子表面活性剂 |
| AU2012242887B2 (en) | 2011-04-13 | 2015-05-07 | Elc Management Llc | Conditioning agents for personal care compositions |
| WO2012155074A1 (en) * | 2011-05-12 | 2012-11-15 | Virent, Inc. | Process for purifying lignocellulosic feedstocks |
| US8629243B2 (en) | 2011-08-16 | 2014-01-14 | E I Du Pont De Nemours And Company | Variant sucrose transporter polypeptides that enable faster sucrose utilization in bacteria |
| EP2684906B1 (en) | 2011-09-06 | 2016-04-06 | Toray Industries, Inc. | Polyester with excellent heat resistance and method for producing same |
| EP2767589B1 (en) * | 2011-10-14 | 2017-12-20 | Toray Industries, Inc. | Process for producing 2,3-butanediol |
| JP5755995B2 (ja) * | 2011-10-26 | 2015-07-29 | 株式会社日立製作所 | 超臨界水を用いた反応プロセス |
| US20130206580A1 (en) * | 2011-12-08 | 2013-08-15 | Oakwood Foods. LLC d/b/a Oakwood Technologies | Continuous coolant purification process and device |
| US8759559B2 (en) | 2012-04-18 | 2014-06-24 | E I Du Pont De Nemours And Company | Processes for preparing polytrimethylene ether glycol esters |
| EP2843061B1 (en) * | 2012-04-26 | 2017-06-07 | Toray Industries, Inc. | Method for producing sugar solution |
| EA030870B1 (ru) * | 2012-06-05 | 2018-10-31 | Дженоматика, Инк. | Способы получения сложного полиэфира и полиуретана |
| WO2013183592A1 (ja) | 2012-06-05 | 2013-12-12 | 三菱化学株式会社 | 1,4-ブタンジオールの製造方法 |
| JP2012245519A (ja) * | 2012-07-17 | 2012-12-13 | Horiba Ltd | 塩分ミスト除去装置およびこれを用いた分析装置 |
| EP2890769B1 (en) * | 2012-08-29 | 2019-08-21 | Archer Daniels Midland Company | Removal of organic salts from bio-derived glycol products |
| FI2937328T4 (fi) | 2012-12-19 | 2025-06-11 | Toray Industries | Alkoholin valmistusmenetelmä |
| JP6048159B2 (ja) * | 2013-01-22 | 2016-12-21 | 三菱化学株式会社 | ポリウレタンの製造方法 |
| EP4403543A3 (en) * | 2013-03-15 | 2024-11-20 | Genomatica, Inc. | Process and systems for obtaining 1,4-butanediol from fermentation broths |
| JP2015017087A (ja) * | 2013-06-13 | 2015-01-29 | 三菱化学株式会社 | ジオールの製造方法 |
| EP3041942B1 (en) * | 2013-09-03 | 2020-07-01 | PTT Global Chemical Public Company Limited | A process for manufacturing acrylic acid, acrylonitrile and 1,4-butanediol from 1,3-propanediol |
| US9309205B2 (en) * | 2013-10-28 | 2016-04-12 | Wincom, Inc. | Filtration process for purifying liquid azole heteroaromatic compound-containing mixtures |
| EP2896628B1 (en) | 2014-01-20 | 2018-09-19 | Jennewein Biotechnologie GmbH | Process for efficient purification of neutral human milk oligosaccharides (HMOs) from microbial fermentation |
| EP3919565A1 (en) | 2014-02-24 | 2021-12-08 | DuPont Industrial Biosciences USA, LLC | Plasticized polyamide compositions |
| JP6486020B2 (ja) * | 2014-05-30 | 2019-03-20 | 三菱ケミカル株式会社 | 2,3−ブタンジオールの製造方法 |
| US10086339B2 (en) | 2015-03-10 | 2018-10-02 | The University Of Connecticut | Polymers and membranes for separation of polar organic compounds from aqueous mixtures and methods of using |
| WO2016186122A1 (ja) * | 2015-05-20 | 2016-11-24 | 東洋紡株式会社 | ポリエステル樹脂 |
| US9968531B2 (en) | 2015-08-05 | 2018-05-15 | Dupont Tate & Lyle Bio Products Company, Llc | Deodorants containing 1,3-propanediol |
| FR3047171A1 (fr) | 2016-01-29 | 2017-08-04 | Plant Advanced Tech Pat | Esters de dipropylene glycol des acides dicafeoylquiniques, extrait vegetal les contenant, procede d'obtention et utilisations |
| CN105777492A (zh) * | 2016-04-19 | 2016-07-20 | 中石化上海工程有限公司 | 1,3-丙二醇的精馏提浓方法 |
| CN105732321A (zh) * | 2016-04-19 | 2016-07-06 | 中石化上海工程有限公司 | 1,3-丙二醇的精馏提浓装置 |
| FR3059236B1 (fr) | 2016-11-25 | 2019-05-17 | Plant Advanced Technologies Pat | Extraits de plantes du genre tagetes et leurs utilisations |
| CN108117481A (zh) * | 2016-11-29 | 2018-06-05 | 中国石油化工股份有限公司 | 一种从发酵液中分离提取1,3-丙二醇的方法 |
| CN106748648A (zh) * | 2016-12-02 | 2017-05-31 | 苏州苏震生物工程有限公司 | 一种1,3‑丙二醇发酵液脱盐除杂系统及方法 |
| FR3061657B1 (fr) | 2017-01-09 | 2020-01-03 | Plant Advanced Technologies Pat | Preparation d’un extrait racinaire de filipendula ulmaria et utilisations cosmetiques |
| JP2020512351A (ja) * | 2017-03-31 | 2020-04-23 | ジェノマティカ, インコーポレイテッド | 発酵ブロスから1,3−ブタンジオールを取得するためのプロセスおよびシステム |
| FR3069161B1 (fr) | 2017-07-21 | 2019-08-30 | Plant Advanced Technologies Pat | Extraits racinaires de polygonum multiflorum et leurs utilisations |
| FR3072025B1 (fr) | 2017-10-06 | 2019-11-01 | Plant Advanced Technologies Pat | Extraits racinaires de plantes du genre morus et leurs utilisations |
| CN107617251A (zh) * | 2017-10-19 | 2018-01-23 | 苏州苏震生物工程有限公司 | 一种用于1,3‑丙二醇和2,3‑丁二醇发酵液预处理的设备及工艺 |
| MX2020005449A (es) * | 2017-11-27 | 2020-08-27 | Novamont Spa | Procedimiento para la produccion de 1,4-butanodiol a partir de fuentes renovables y poliesteres obtenidos del mismo. |
| US11414365B2 (en) | 2018-01-30 | 2022-08-16 | Inolex Investment Corporation | Natural 1,2-alkanediols, compositions having natural 1,2-alkanediols and processes for making the same |
| WO2020006043A1 (en) | 2018-06-28 | 2020-01-02 | Dupont Industrial Biosciences Usa, Llc | Spun yarn comprising polyester staple fibre and fabric comprising the same |
| CN113166008B (zh) | 2018-09-21 | 2024-02-06 | 维尔萨利斯股份公司 | 用于从发酵液纯化bio-1,3-丁二醇的方法 |
| EP4051008A1 (en) | 2019-11-01 | 2022-09-07 | Primient Covation LLC | Use and methods of 1,3-propanediol to improve taste and/or off-taste qualities |
| CN112843762B (zh) * | 2019-11-26 | 2024-05-24 | 南京华基塔业有限公司 | 一种由寡聚物制备丙交酯的反应系统及方法 |
| CN114075097B (zh) * | 2021-04-21 | 2024-06-14 | 广州国宏新材料有限公司 | 膜过滤处理1,3-丙二醇发酵液的方法和装置 |
| EP4349445A4 (en) * | 2021-06-02 | 2025-05-07 | Nippon Shokubai Co., Ltd. | TANK IMPLEMENTED IN A PURIFICATION DEVICE |
| WO2022265429A1 (ko) * | 2021-06-16 | 2022-12-22 | 지에스칼텍스 주식회사 | 발효액으로부터 목적한 화합물을 수득하는 방법 |
| CN113337548B (zh) * | 2021-08-02 | 2022-03-22 | 苏州苏震生物工程有限公司 | 一种生物基1,3-丙二醇的制备方法 |
| CN114249633B (zh) * | 2022-01-05 | 2023-10-27 | 江苏扬农化工集团有限公司 | 一种分离提纯1,3-丙二醇的方法 |
| CN114504872A (zh) * | 2022-02-15 | 2022-05-17 | 北京袭明科技有限公司 | 一种高纯电子级乙二醇生产方法及装置 |
| KR102810479B1 (ko) * | 2022-08-04 | 2025-05-21 | 씨제이제일제당(주) | 색가 모니터링을 통한 정제 공정 제어 방법 및 시스템, 및 폴리하이드록시알카노에이트 수지의 제조 방법 |
| EP4586828A1 (en) | 2022-09-16 | 2025-07-23 | Primient Covation LLC | Compositions comprising and methods of using 1,3-propanediol to improve sweetness and/or reduce bitterness of sweeteners |
| WO2025258949A1 (ko) * | 2024-06-10 | 2025-12-18 | 지에스칼텍스 주식회사 | 다가 알코올의 정제 방법 |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0640973A (ja) * | 1992-06-03 | 1994-02-15 | Degussa Ag | 1,3−プロパンジオールの製法 |
| JPH06157378A (ja) * | 1992-07-10 | 1994-06-03 | Degussa Ag | 1,3−プロパンジオールの製造方法 |
| JPH11169189A (ja) * | 1997-10-07 | 1999-06-29 | Mitsubishi Chemical Corp | 高純度エリスリトール結晶の製造方法 |
| WO2001044348A1 (en) * | 1999-12-17 | 2001-06-21 | E.I. Du Pont De Nemours And Company | Production of polytrimethylene ether glycol and copolymers thereof |
| WO2001044150A2 (en) * | 1999-12-17 | 2001-06-21 | E.I. Du Pont De Nemours And Company | Continuous process for the preparation of polytrimethylene ether glycol |
| JP2003510170A (ja) * | 1999-09-30 | 2003-03-18 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 水溶液中の固体からの揮発性化合物の回収法 |
| WO2004076392A1 (en) * | 2003-02-24 | 2004-09-10 | Shell Internationale Research Maatschappij B.V. | Purification of 1,3-propanediol by distillation |
| JP2007501324A (ja) * | 2003-05-06 | 2007-01-25 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 生化学的に誘導された1,3−プロパンジオールからの優れた品質のポリトリメチレンエーテルグリコール |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4380678A (en) | 1981-01-21 | 1983-04-19 | Hydrocarbon Research, Inc. | Multi-stage aldoses to polyols process |
| US5194159A (en) | 1989-12-27 | 1993-03-16 | Union Carbide Chemicals & Plastics Technology Corporation | Treatment of lower glycol-containing operative fluids |
| US5034134A (en) * | 1989-12-27 | 1991-07-23 | Union Carbide Chemicals And Plastics Technology Corporation | Treatment of impurity-containing liquid streams in ethylene oxide/glycol processes with semi-permeable membranes |
| US5223144A (en) * | 1990-08-08 | 1993-06-29 | First Brands Corporation | Process for treatment of aqueous soluions of polyhydric alcohols |
| US5340909A (en) * | 1991-12-18 | 1994-08-23 | Hoechst Celanese Corporation | Poly(1,3-propylene terephthalate) |
| US5527973A (en) * | 1994-12-16 | 1996-06-18 | Kelsey; Donald R. | Purification of 1,3-propanediol |
| US5686276A (en) * | 1995-05-12 | 1997-11-11 | E. I. Du Pont De Nemours And Company | Bioconversion of a fermentable carbon source to 1,3-propanediol by a single microorganism |
| AU733534B2 (en) * | 1996-11-13 | 2001-05-17 | E.I. Du Pont De Nemours And Company | Method for the production of 1,3-propanediol by recombinant microorganisms |
| CA2625060A1 (en) * | 1996-11-13 | 1998-05-22 | E.I. Du Pont De Nemours And Company | Method for the production of glycerol by recombinant organisms |
| DE19840277A1 (de) * | 1998-09-04 | 2000-03-09 | Degussa | Verfahren zur Reduzierung des Gehalts an Acetalen oder Ketalen in alkoholischen Reaktionsgemischen |
| AU1234400A (en) | 1998-10-27 | 2000-05-15 | Cargill Incorporated | Method for purifying a polyol product stream |
| US6245879B1 (en) * | 1999-01-29 | 2001-06-12 | Shell Oil Company | Purification of 1,3-propanediol in carbonyl-containing stream |
| US20040198965A1 (en) * | 1999-04-20 | 2004-10-07 | Cargill B.V. | D-galactose isolation system |
| CA2386169A1 (en) | 1999-09-30 | 2001-04-12 | Cognis Corporation | Improved fermentation process |
| US6361983B1 (en) * | 1999-09-30 | 2002-03-26 | E. I. Du Pont De Nemours And Company | Process for the isolation of 1,3-propanediol from fermentation broth |
| US6479716B2 (en) * | 2000-03-29 | 2002-11-12 | Archer-Daniels-Midland Company | Method of recovering 1,3-propanediol from fermentation broth |
| WO2001073097A2 (en) | 2000-03-29 | 2001-10-04 | Archer-Daniels-Midland Company | Method of recovering 1,3-propanediol from fermentation broth |
| WO2004101482A2 (en) | 2003-05-06 | 2004-11-25 | E.I. Dupont De Nemours And Company | Hydrogenation of biochemically derived 1,3-propanediol |
| JP4814794B2 (ja) * | 2003-05-06 | 2011-11-16 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 生物学的に生産された1,3−プロパンジオールの精製 |
| US7714174B2 (en) * | 2007-03-27 | 2010-05-11 | E. I. Du Pont De Nemours And Company | Lower-color polytrimethylene ether glycol using hydride compounds |
-
2004
- 2004-05-05 JP JP2006532802A patent/JP4814794B2/ja not_active Expired - Fee Related
- 2004-05-05 US US10/839,188 patent/US7919658B2/en not_active Expired - Fee Related
- 2004-05-05 EP EP10169053A patent/EP2239334A1/en not_active Withdrawn
- 2004-05-05 KR KR1020057020976A patent/KR101105957B1/ko not_active Expired - Fee Related
- 2004-05-05 DE DE602004028359T patent/DE602004028359D1/de not_active Expired - Lifetime
- 2004-05-05 EP EP04760882A patent/EP1625224B1/en not_active Expired - Lifetime
- 2004-05-05 BR BRPI0410685A patent/BRPI0410685B8/pt not_active IP Right Cessation
- 2004-05-05 CN CNB2004800191639A patent/CN100478446C/zh not_active Expired - Lifetime
- 2004-05-05 CA CA2522928A patent/CA2522928C/en not_active Expired - Lifetime
- 2004-05-05 WO PCT/US2004/014043 patent/WO2004101479A2/en not_active Ceased
- 2004-05-06 TW TW093112822A patent/TW200506063A/zh unknown
-
2011
- 2011-02-25 US US13/035,261 patent/US20110152581A1/en not_active Abandoned
- 2011-02-25 US US13/035,246 patent/US8183417B2/en not_active Expired - Lifetime
- 2011-03-15 JP JP2011056908A patent/JP2011126911A/ja active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0640973A (ja) * | 1992-06-03 | 1994-02-15 | Degussa Ag | 1,3−プロパンジオールの製法 |
| JPH06157378A (ja) * | 1992-07-10 | 1994-06-03 | Degussa Ag | 1,3−プロパンジオールの製造方法 |
| JPH11169189A (ja) * | 1997-10-07 | 1999-06-29 | Mitsubishi Chemical Corp | 高純度エリスリトール結晶の製造方法 |
| JP2003510170A (ja) * | 1999-09-30 | 2003-03-18 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 水溶液中の固体からの揮発性化合物の回収法 |
| WO2001044348A1 (en) * | 1999-12-17 | 2001-06-21 | E.I. Du Pont De Nemours And Company | Production of polytrimethylene ether glycol and copolymers thereof |
| WO2001044150A2 (en) * | 1999-12-17 | 2001-06-21 | E.I. Du Pont De Nemours And Company | Continuous process for the preparation of polytrimethylene ether glycol |
| WO2004076392A1 (en) * | 2003-02-24 | 2004-09-10 | Shell Internationale Research Maatschappij B.V. | Purification of 1,3-propanediol by distillation |
| JP2007501324A (ja) * | 2003-05-06 | 2007-01-25 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 生化学的に誘導された1,3−プロパンジオールからの優れた品質のポリトリメチレンエーテルグリコール |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101105957B1 (ko) | 2012-01-18 |
| US8183417B2 (en) | 2012-05-22 |
| CA2522928A1 (en) | 2004-11-25 |
| DE602004028359D1 (de) | 2010-09-09 |
| EP1625224B1 (en) | 2010-07-28 |
| BRPI0410685A (pt) | 2006-06-20 |
| BRPI0410685B1 (pt) | 2013-12-31 |
| BRPI0410685B8 (pt) | 2017-05-30 |
| CN100478446C (zh) | 2009-04-15 |
| US7919658B2 (en) | 2011-04-05 |
| CN1816629A (zh) | 2006-08-09 |
| JP2007502325A (ja) | 2007-02-08 |
| EP2239334A1 (en) | 2010-10-13 |
| JP2011126911A (ja) | 2011-06-30 |
| CA2522928C (en) | 2013-09-24 |
| US20110152583A1 (en) | 2011-06-23 |
| TW200506063A (en) | 2005-02-16 |
| WO2004101479A2 (en) | 2004-11-25 |
| US20110152581A1 (en) | 2011-06-23 |
| KR20060052677A (ko) | 2006-05-19 |
| US20050069997A1 (en) | 2005-03-31 |
| EP1625224A2 (en) | 2006-02-15 |
| WO2004101479A3 (en) | 2005-02-03 |
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