DE60124229T2 - Verfahren zur gewinnung von organischen säuren aus wässrigen lösungen - Google Patents
Verfahren zur gewinnung von organischen säuren aus wässrigen lösungen Download PDFInfo
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- DE60124229T2 DE60124229T2 DE60124229T DE60124229T DE60124229T2 DE 60124229 T2 DE60124229 T2 DE 60124229T2 DE 60124229 T DE60124229 T DE 60124229T DE 60124229 T DE60124229 T DE 60124229T DE 60124229 T2 DE60124229 T2 DE 60124229T2
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- XWSGEVNYFYKXCP-UHFFFAOYSA-N 2-[carboxymethyl(methyl)amino]acetic acid Chemical compound OC(=O)CN(C)CC(O)=O XWSGEVNYFYKXCP-UHFFFAOYSA-N 0.000 description 1
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- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
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- 229910001504 inorganic chloride Inorganic materials 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/803—Physical recovery methods, e.g. chromatography, grinding
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/874—Pseudomonas
- Y10S435/876—Pseudomonas fluorescens
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/886—Streptomyces
- Y10S435/896—Streptomyces fradiae
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/519,936 US6670505B1 (en) | 2000-03-07 | 2000-03-07 | Process for the recovery of organic acids from aqueous solutions |
| US519936 | 2000-03-07 | ||
| PCT/US2001/007140 WO2001066508A2 (en) | 2000-03-07 | 2001-03-06 | Process for the recovery of organic acids from aqueous solutions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60124229D1 DE60124229D1 (de) | 2006-12-14 |
| DE60124229T2 true DE60124229T2 (de) | 2007-02-15 |
Family
ID=24070463
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60124229T Expired - Fee Related DE60124229T2 (de) | 2000-03-07 | 2001-03-06 | Verfahren zur gewinnung von organischen säuren aus wässrigen lösungen |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US6670505B1 (https=) |
| EP (1) | EP1261574B1 (https=) |
| JP (1) | JP2003525923A (https=) |
| CN (1) | CN100413839C (https=) |
| AT (1) | ATE344225T1 (https=) |
| BR (1) | BR0109005A (https=) |
| DE (1) | DE60124229T2 (https=) |
| WO (1) | WO2001066508A2 (https=) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10007702A1 (de) | 2000-02-19 | 2001-08-23 | Sueddeutsche Kalkstickstoff | Verfahren zur Herstellung von N-(Phosphonomethyl)glycin |
| DE60115019T2 (de) | 2000-05-22 | 2006-08-03 | Monsanto Technology Llc. | Reaktionssysteme zur herstellung von n-(phosphonomethyl)glyzin verbindungen |
| WO2004056841A1 (de) * | 2002-12-19 | 2004-07-08 | Basf Aktiengesellschaft | Verfahren zum extrahieren von 2-keto-l-gulonsäure (kgs) aus einem polaren, vorzugsweise wässrigen lösungsmittel |
| DE10308045B3 (de) * | 2003-02-26 | 2004-06-17 | Lurgi Ag | Verfahren und Vorrichtung zur kontinuierlichen Gewinnung freier Weinsäure aus Kaliumhydrogentartrat enthaltenden Rohstoffen |
| JP4469568B2 (ja) | 2003-07-09 | 2010-05-26 | 三菱化学株式会社 | 有機酸の製造方法 |
| CN100575496C (zh) | 2003-08-28 | 2009-12-30 | 三菱化学株式会社 | 产生琥珀酸的方法 |
| EP1672067B1 (en) | 2003-09-17 | 2015-11-11 | Mitsubishi Chemical Corporation | Process for producing non-amino organic acid |
| CN100534972C (zh) * | 2003-09-30 | 2009-09-02 | 味之素株式会社 | 从发酵液中纯化琥珀酸的方法 |
| EP1760143B1 (en) | 2004-05-20 | 2012-05-16 | Ajinomoto Co., Inc. | Succinic acid-producing bacterium and process for producing succinic acid |
| CN100389075C (zh) * | 2004-08-10 | 2008-05-21 | 株式会社神钢环境舒立净 | 排水处理方法和排水处理装置 |
| JP2008514695A (ja) * | 2004-10-01 | 2008-05-08 | ジーイー・ヘルスケア・アクスイェ・セルスカプ | ピルビン酸の製造方法 |
| JP5088136B2 (ja) | 2005-10-18 | 2012-12-05 | 味の素株式会社 | コハク酸の製造方法 |
| JP5180060B2 (ja) | 2006-02-24 | 2013-04-10 | 三菱化学株式会社 | 有機酸生産菌及び有機酸の製造法 |
| CN101906032A (zh) * | 2010-07-14 | 2010-12-08 | 华东理工大学 | 回收和循环使用l-(+)-酒石酸的方法 |
| WO2013025105A1 (en) | 2011-08-16 | 2013-02-21 | /Purac Biochem B.V. | Recovery of carboxylic acid from their magnesium salts by precipitation using hydrochloric acid, useful for fermentation broth work-up |
| EA027342B1 (ru) * | 2011-08-16 | 2017-07-31 | Пурак Биокем Б.В. | Извлечение карбоновой кислоты из ее магниевых солей путем осаждения c применением хлористо-водородной кислоты, пригодное для выделения продукта реакции из ферментативного бульона |
| EP3845486A1 (en) * | 2011-08-16 | 2021-07-07 | Purac Biochem B.V. | Recovery of carboxylic acid from their magnesium salts by precipitation using hydrochloric acid, useful for fermentation broth work-up |
| CN108148027A (zh) * | 2011-08-16 | 2018-06-12 | 普拉克生化公司 | 可用于发酵液处理的通过用盐酸沉淀从羧酸镁盐中回收羧酸的方法 |
| US9480574B2 (en) | 2013-03-14 | 2016-11-01 | Benvenue Medical, Inc. | Spinal fusion implants and devices and methods for deploying such implants |
| CN103450007B (zh) * | 2013-09-02 | 2015-06-17 | 西安通鑫半导体辅料有限公司 | 一种从硅片脱胶工序产生的废乳酸中回收乳酸的方法 |
| US9422398B2 (en) | 2014-05-30 | 2016-08-23 | Industrial Technology Research Institute | Copolymer, and method for preparing a monomer used to form the copolymer |
| US10314605B2 (en) | 2014-07-08 | 2019-06-11 | Benvenue Medical, Inc. | Apparatus and methods for disrupting intervertebral disc tissue |
| CN104447529B (zh) * | 2014-11-25 | 2017-05-24 | 利尔化学股份有限公司 | 3,6‑二氯吡啶甲酸的提取纯化方法 |
| CN104672078B (zh) * | 2015-02-02 | 2017-05-24 | 江苏索普（集团）有限公司 | 一种羰基合成醋酸副产物提纯制丙酸的工艺 |
| US10022243B2 (en) | 2015-02-06 | 2018-07-17 | Benvenue Medical, Inc. | Graft material injector system and method |
| US10758286B2 (en) | 2017-03-22 | 2020-09-01 | Benvenue Medical, Inc. | Minimal impact access system to disc space |
| WO2019148083A1 (en) | 2018-01-29 | 2019-08-01 | Benvenue Medical, Inc. | Minimally invasive interbody fusion |
| WO2019178575A1 (en) | 2018-03-16 | 2019-09-19 | Benvenue Medical, Inc. | Articulated instrumentation and methods of using the same |
| CN108314164B (zh) * | 2018-03-27 | 2020-06-19 | 浙江大学 | 回收废水中钡的方法 |
| CN108947066A (zh) * | 2018-07-13 | 2018-12-07 | 宁波永顺精细化工有限公司 | 羧酸钡废水中羧酸及钡盐的回收方法 |
| NZ777498A (en) * | 2018-12-19 | 2024-11-29 | Basf Se | Method for separating biomass from a solution comprising biomass and at least one oligosaccharide |
| KR102520535B1 (ko) * | 2018-12-24 | 2023-04-11 | 안형일 | 미네랄을 포함하는 사료 첨가 조성물 |
| CN111943836A (zh) * | 2019-05-16 | 2020-11-17 | 帝斯曼知识产权资产管理有限公司 | 回收2-酮-l-古洛糖酸的改进方法 |
| CN111978202B (zh) * | 2020-08-12 | 2022-08-05 | 浙江理工大学上虞工业技术研究院有限公司 | 可碱洗分散染料水解产物的回收方法 |
| CN112552164B (zh) * | 2020-12-08 | 2022-12-09 | 日照金禾博源生化有限公司 | 一种从不合格柠檬酸钠母液中提取苹果酸的工艺方法 |
| WO2023076622A1 (en) * | 2021-10-29 | 2023-05-04 | Alliance For Sustainable Energy, Llc | Process for the recovery of monopotassium glucarate and glucaric acid |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2318500A (en) * | 1935-10-21 | 1943-05-04 | Parke Davis & Co | Preparation of ascorbic acid and 1-gulosone |
| US2421611A (en) * | 1945-05-04 | 1947-06-03 | Byron E Gray | Preparation of 2-keto gulonic acid and its salts |
| US2421612A (en) | 1945-05-04 | 1947-06-03 | Byron E Gray | Preparation of 2-keto gulonic acid and its salts |
| US2462251A (en) | 1945-05-16 | 1949-02-22 | Merck & Co Inc | Process for preparing ascorbic acids |
| US2918492A (en) * | 1956-08-24 | 1959-12-22 | Miles Lab | Method of preparing methyl 2-ketogluconate |
| US3043749A (en) * | 1960-07-28 | 1962-07-10 | Pfizer & Co C | Preparation of 2-keto-l-gulonic acid |
| US3234105A (en) * | 1962-09-20 | 1966-02-08 | Takeda Chemical Industries Ltd | Method for producing 2-keto-lgulonic acid |
| US3381027A (en) * | 1964-04-22 | 1968-04-30 | Hoffmann La Roche | Preparation and recovery of methyl 2-ketogluconate |
| US4113771A (en) | 1971-04-07 | 1978-09-12 | Ethyl Corporation | Process for the purification of citric acid |
| US4202828A (en) | 1978-01-10 | 1980-05-13 | Kawasaki Kasei Chemicals Limited | Process for separation of naphthoquinone and phthalic acid |
| FR2421864A1 (fr) | 1978-04-05 | 1979-11-02 | Hoechst France | Procede de fabrication de l'acide hydroxy-4, dimethoxy-3,5 benzoique a partir de l'acide trimethoxy-3,4,5 benzoique |
| US4334074A (en) | 1981-02-02 | 1982-06-08 | The Dow Chemical Company | Method of recovering 3,6-dichloropicolinic acid from basic aqueous solutions of salts thereof |
| DE3345411A1 (de) | 1983-12-15 | 1985-06-27 | Dynamit Nobel Ag, 5210 Troisdorf | Verfahren zur reindarstellung von carbonsaeuren |
| US4771001A (en) | 1986-03-27 | 1988-09-13 | Neurex Corp. | Production of lactic acid by continuous fermentation using an inexpensive raw material and a simplified method of lactic acid purification |
| US5168055A (en) | 1986-06-11 | 1992-12-01 | Rathin Datta | Fermentation and purification process for succinic acid |
| US5202476A (en) * | 1988-04-29 | 1993-04-13 | Takeda Chemical Industries, Ltd. | Purification of 2-keto-L-gulonic acid |
| FR2636343B1 (https=) | 1988-09-13 | 1994-11-25 | Rhone Poulenc Sante | |
| FR2648136B1 (fr) | 1989-06-12 | 1994-06-17 | Rhone Poulenc Sante | Procede de preparation de l'acide ascorbique |
| CH678057A5 (de) | 1989-06-26 | 1991-07-31 | Enco Eng Ag | Verfahren zur herstellung von natrium- oder kalium-l-ascorbat. |
| US5202475A (en) | 1990-09-27 | 1993-04-13 | Eastman Kodak Company | Process for preparation of cyclohexanedicarboxylic acid |
| DE69112770T2 (de) | 1990-11-02 | 1996-05-09 | Mitsubishi Chem Corp | Verfahren zur Abscheidung der organischen Säure oder Säuren aus einer organische Säuren enthaltenden Lösung. |
| US5210296A (en) | 1990-11-19 | 1993-05-11 | E. I. Du Pont De Nemours And Company | Recovery of lactate esters and lactic acid from fermentation broth |
| US5159110A (en) | 1991-05-16 | 1992-10-27 | W. R. Grace & Co.-Conn. | Process for recovering n-methyliminodiacetic acid from sodium sulfate |
| IT1254254B (it) | 1992-03-11 | 1995-09-14 | Erregierre Ind Chim | Procedimento per la preparazione di acido iodesossicolico ad elevata purezza per impiego farmaceutico |
| US5352825A (en) | 1993-07-06 | 1994-10-04 | Hoarmann & Reimer Corp. | Recovery of organic acid salts from impure process streams by addition of bases |
| CA2126365C (en) | 1993-07-06 | 1999-08-24 | Steven W. Felman | Recovery of citric acid from impure process streams by addition of strong acids and salts thereof |
| US5426219A (en) | 1993-07-26 | 1995-06-20 | A.E. Staley Manufacturing Co. | Process for recovering organic acids |
| US5410076A (en) | 1993-11-12 | 1995-04-25 | Lever Brothers Company, Division Of Conopco, Inc. | Process for the preparation of bis(amidocarboxylic acid) |
| US5741681A (en) | 1994-12-09 | 1998-04-21 | Mitsubishi Chemical Corporation | Method for producing L-aspartic acid |
| US5522995A (en) | 1995-02-28 | 1996-06-04 | Cockrem; Michael C. M. | Process for recovering organic acids from aqueous salt solutions |
| JP3976832B2 (ja) | 1996-04-30 | 2007-09-19 | ディーエスエム アイピー アセッツ ビー．ブイ． | ２−ケト−ｌ−グロン酸の単離方法 |
-
2000
- 2000-03-07 US US09/519,936 patent/US6670505B1/en not_active Expired - Fee Related
-
2001
- 2001-03-06 BR BR0109005-4A patent/BR0109005A/pt not_active IP Right Cessation
- 2001-03-06 WO PCT/US2001/007140 patent/WO2001066508A2/en not_active Ceased
- 2001-03-06 CN CNB018090400A patent/CN100413839C/zh not_active Expired - Fee Related
- 2001-03-06 EP EP01918380A patent/EP1261574B1/en not_active Expired - Lifetime
- 2001-03-06 DE DE60124229T patent/DE60124229T2/de not_active Expired - Fee Related
- 2001-03-06 JP JP2001565329A patent/JP2003525923A/ja not_active Withdrawn
- 2001-03-06 AT AT01918380T patent/ATE344225T1/de not_active IP Right Cessation
- 2001-08-03 US US09/921,946 patent/US20020026077A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN100413839C (zh) | 2008-08-27 |
| EP1261574A2 (en) | 2002-12-04 |
| CN1427813A (zh) | 2003-07-02 |
| JP2003525923A (ja) | 2003-09-02 |
| US6670505B1 (en) | 2003-12-30 |
| US20020026077A1 (en) | 2002-02-28 |
| DE60124229D1 (de) | 2006-12-14 |
| WO2001066508A3 (en) | 2002-05-02 |
| BR0109005A (pt) | 2003-06-03 |
| ATE344225T1 (de) | 2006-11-15 |
| EP1261574B1 (en) | 2006-11-02 |
| WO2001066508A2 (en) | 2001-09-13 |
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| 8339 | Ceased/non-payment of the annual fee |