GB933714A - Improvements in or relating to the recovery of organic compounds from dilute aqueoussolution - Google Patents
Improvements in or relating to the recovery of organic compounds from dilute aqueoussolutionInfo
- Publication number
- GB933714A GB933714A GB29421/59A GB2942159A GB933714A GB 933714 A GB933714 A GB 933714A GB 29421/59 A GB29421/59 A GB 29421/59A GB 2942159 A GB2942159 A GB 2942159A GB 933714 A GB933714 A GB 933714A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acetal
- ester
- solvent
- acid
- acetaldehyde
- 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.)
- Expired
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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound
- C07C29/92—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound by a consecutive conversion and reconstruction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
-
- 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
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/12—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Esters or acetals are prepared from a dilute aqueous solution of a water-soluble organic compound, which is a glycol or a polyhydric alcohol or contains an aldehyde or carboxylic acid group by adding as appropriate a water-soluble ester- or acetal-forming compound, which is carboxylic, alcoholic or aldehydic, reacting the added compound with the already dissolved compound under ester- or acetal-forming conditions and during said reaction preferentially solvent extracting the resulting ester or acetal from the aqueous mixture with a water-immiscible or partially immiscible solvent by carrying out the reaction in the presence of the solvent or by intermittently extracting the reaction mixture with successive portions of the solvent, so that the equilibrium in the aqueous phase is displaced in the direction of the acetal or ester formation and recovering the organic extract. In a modification, excess of the ester- or acetal-forming compound is used to serve as the solvent, provided it is not completely miscible with the aqueous solution. The dilute aqueous solutions used are those containing up to 20% w/v of the water soluble organic compound. The reactions of a di- or polyhydric alcohol with an aldehyde to form an acetal, a carboxylic acid with an alcohol to form an ester and a hydroxy carboxylic acid with an aldehyde to form a cyclic acetal ester, are mentioned; if two ester- or acetal-forming functional groups are present, a di-acetal or di-ester may be prepared; use of a suitably substituted compound, e.g. glyoxylic acid enables simultaneous acetalisation and esterification to occur. An acid catalyst may be present and the reaction extraction can be effected continuously in an extraction column. The ester or acetal may be separated from at least part of the solvent in the extract by distillation, crystallisation or solvent extraction. The recovered ester or acetal may be decomposed by hydrolysis to yield the original water soluble organic compound in separated concentrated form, and the ester- or acetal-forming compound originally added. Alternatively, the original water-soluble organic compound may be recovered from the ester or acetal by transesterification or transacetalisation in a solvent for the ester or acetal in which the original water soluble organic compound is only slightly soluble. Examples describe the reaction as above of dilute aqueous solutions of (1) 1:3-or 2:3-butane diol with acetaldehyde yielding the cyclic acetal; (2) glycerol with acetaldehyde to yield the cyclic acetal; (3) erythritol with acetaldehyde yielding the di-acetal; (4) acetic acid with methanol yielding methyl acetate; (5) lactic acid with acetaldehyde yielding 2:5-dimethyl-1:3-dioxolan; (6) glyoxylic acid with methanol and butylene glycol to form the cyclic diol acetal of glyoxylic acid methyl ester; (7) pyrrolidone carboxylic acid and methanol forming the methyl ester, typical solvents used being xylene, methylene chloride, dichloro benzene, benzophenone, chloroform and diphenylene oxide. Examples (12) and (13) describe the hydrolysis of the butane diol acetal obtained in (1), by heating the acetal with a limited amount of water and formic or sulphuric acid as catalyst and distilling off the liberated acetaldehyde and excess water. The treatment of dilute aqueous glycollic acid and glyoxal solutions is also mentioned. Reference is also made to the recovery of glyoxylic acid in the form of its butane diol acetal which is heated with acetaldehyde to liberate the glyoxylic acid.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DET15601A DE1240525B (en) | 1958-09-09 | 1958-09-09 | Process for the production of alcohols, carboxylic acids or aldehydes from their aqueous solutions in the form of their esters, acetals or ester acetals |
Publications (1)
Publication Number | Publication Date |
---|---|
GB933714A true GB933714A (en) | 1963-08-14 |
Family
ID=7547969
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB29421/59A Expired GB933714A (en) | 1958-09-09 | 1959-08-28 | Improvements in or relating to the recovery of organic compounds from dilute aqueoussolution |
Country Status (3)
Country | Link |
---|---|
DE (1) | DE1240525B (en) |
GB (1) | GB933714A (en) |
NL (1) | NL243096A (en) |
Cited By (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1294390B (en) * | 1964-09-12 | 1969-05-08 | Basf Ag | Process for the purification of crude dioxolane |
US4058555A (en) | 1969-07-18 | 1977-11-15 | El Paso Products Company | Process for the purification of mixed acids |
US4076948A (en) | 1968-10-10 | 1978-02-28 | El Paso Products Company | Process for treatment of adipic acid mother liquor |
US4105856A (en) * | 1970-09-29 | 1978-08-08 | El Paso Products Company | Recovery process for aqueous waste streams in adipic acid systems |
US4375552A (en) | 1969-01-31 | 1983-03-01 | C. P. Hall Company | Nitric acid process for production of adipic acid from hydrocarbons |
GB2145410A (en) * | 1983-08-08 | 1985-03-27 | Kotobuki Seiyaku Co Ltd | 1,3-dioxane derivatives |
WO1996031456A1 (en) * | 1995-04-07 | 1996-10-10 | Hoechst Celanese Corporation | Recovery of acetic acid from dilute aqueous streams formed during a carbonylation process |
EP1813590A1 (en) * | 1999-03-11 | 2007-08-01 | ZeaChem Inc. | Process for recovering an ester |
US7351559B2 (en) | 1999-03-11 | 2008-04-01 | Zeachem, Inc. | Process for producing ethanol |
US7507562B2 (en) | 1999-03-11 | 2009-03-24 | Zeachem, Inc. | Process for producing ethanol from corn dry milling |
US7601865B2 (en) | 2004-01-29 | 2009-10-13 | Zeachem, Inc. | Recovery of organic acids |
FR2931150A1 (en) * | 2008-05-19 | 2009-11-20 | Rhodia Poliamida E Especialidades Ltda | PROCESS FOR PURIFYING RAW GLYCEROL |
WO2010075616A1 (en) * | 2009-01-05 | 2010-07-08 | Serviço Nacional De Aprendizagem Industrial-Senai/Dr-Ba | Process for purifying light-coloured glycerol from biodiesel transesterification |
EP2295394A1 (en) * | 2009-09-11 | 2011-03-16 | Rhodia Poliamida E Especialidades Ltda | Process for the purification of crude glycerol |
FR2964658A1 (en) * | 2010-09-15 | 2012-03-16 | Rhodia Operations | PROCESS FOR PRODUCING DIOXOLANE |
US8143444B2 (en) | 2008-05-07 | 2012-03-27 | Zeachem, Inc. | Recovery of organic acids |
CN102471216A (en) * | 2009-07-01 | 2012-05-23 | 罗狄亚聚酰胺特殊品有限公司 | Process to obtain a mixture of lower carboxylic mono, di and triesters from raw glycerin |
WO2012076759A1 (en) | 2010-12-10 | 2012-06-14 | Kemira Oyj | A method for recovery of organic acid from dilute aqueous solution |
US8252567B2 (en) | 2008-02-07 | 2012-08-28 | Zeachem, Inc. | Method for the indirect production of butanol and hexanol |
US8329436B2 (en) | 2007-02-09 | 2012-12-11 | Zeachem, Inc. | Method of making propanol and ethanol from plant material by biological conversion and gasification |
US20140235878A1 (en) * | 2011-09-30 | 2014-08-21 | Rhodia Poliamida E Especialidades Ltda | Process for the production of a dioxolane compound from crude glycerol |
CN104926638A (en) * | 2015-05-05 | 2015-09-23 | 湖北省宏源药业科技股份有限公司 | Method and device for continuously concentrating glyoxylic acid |
WO2019092495A1 (en) * | 2017-11-09 | 2019-05-16 | Braskem S.A. | Process for the recovery of ketones and glycols from fermentation |
CN110746270A (en) * | 2019-11-04 | 2020-02-04 | 江苏扬农化工集团有限公司 | Method for recycling epichlorohydrin wastewater |
FR3112964A1 (en) * | 2020-07-28 | 2022-02-04 | IFP Energies Nouvelles | LIQUID-LIQUID REACTIVE EXTRACTION PROCESS |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4358347A (en) * | 1982-01-26 | 1982-11-09 | The Dow Chemical Company | Removal of trace aldehydes from carboxylic acids |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2673222A (en) * | 1949-12-31 | 1954-03-23 | Standard Oil Dev Co | Separation of isomeric alcohols by selective acetalization |
-
0
- NL NL243096D patent/NL243096A/xx unknown
-
1958
- 1958-09-09 DE DET15601A patent/DE1240525B/en active Granted
-
1959
- 1959-08-28 GB GB29421/59A patent/GB933714A/en not_active Expired
Cited By (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1294390B (en) * | 1964-09-12 | 1969-05-08 | Basf Ag | Process for the purification of crude dioxolane |
US4076948A (en) | 1968-10-10 | 1978-02-28 | El Paso Products Company | Process for treatment of adipic acid mother liquor |
US4082788A (en) | 1968-10-10 | 1978-04-04 | El Paso Products Company | Esterification and extraction process |
US4375552A (en) | 1969-01-31 | 1983-03-01 | C. P. Hall Company | Nitric acid process for production of adipic acid from hydrocarbons |
US4058555A (en) | 1969-07-18 | 1977-11-15 | El Paso Products Company | Process for the purification of mixed acids |
US4105856A (en) * | 1970-09-29 | 1978-08-08 | El Paso Products Company | Recovery process for aqueous waste streams in adipic acid systems |
GB2145410A (en) * | 1983-08-08 | 1985-03-27 | Kotobuki Seiyaku Co Ltd | 1,3-dioxane derivatives |
WO1996031456A1 (en) * | 1995-04-07 | 1996-10-10 | Hoechst Celanese Corporation | Recovery of acetic acid from dilute aqueous streams formed during a carbonylation process |
EP1813590A1 (en) * | 1999-03-11 | 2007-08-01 | ZeaChem Inc. | Process for recovering an ester |
US7351559B2 (en) | 1999-03-11 | 2008-04-01 | Zeachem, Inc. | Process for producing ethanol |
US7507562B2 (en) | 1999-03-11 | 2009-03-24 | Zeachem, Inc. | Process for producing ethanol from corn dry milling |
US8236534B2 (en) | 1999-03-11 | 2012-08-07 | Zeachem, Inc. | Process for producing ethanol |
US7888082B2 (en) | 1999-03-11 | 2011-02-15 | Zeachem, Inc. | Process for producing ethanol from corn dry milling |
US7964379B2 (en) | 1999-03-11 | 2011-06-21 | Zeachem, Inc. | Process for producing ethanol |
US7682812B2 (en) | 1999-03-11 | 2010-03-23 | Zeachem, Inc. | Process for producing ethanol |
US8048655B2 (en) | 2004-01-29 | 2011-11-01 | Zeachem, Inc. | Recovery of organic acids |
US7601865B2 (en) | 2004-01-29 | 2009-10-13 | Zeachem, Inc. | Recovery of organic acids |
US8329436B2 (en) | 2007-02-09 | 2012-12-11 | Zeachem, Inc. | Method of making propanol and ethanol from plant material by biological conversion and gasification |
US8252567B2 (en) | 2008-02-07 | 2012-08-28 | Zeachem, Inc. | Method for the indirect production of butanol and hexanol |
US8143444B2 (en) | 2008-05-07 | 2012-03-27 | Zeachem, Inc. | Recovery of organic acids |
US9024081B2 (en) | 2008-05-19 | 2015-05-05 | Rhodia Poliamida E Especialidades Ltda | Purification of crude glycerol |
WO2009141702A1 (en) * | 2008-05-19 | 2009-11-26 | Rhodia Poliamida E Especialidades Ltda | Method of purifying crude glycerol |
FR2931150A1 (en) * | 2008-05-19 | 2009-11-20 | Rhodia Poliamida E Especialidades Ltda | PROCESS FOR PURIFYING RAW GLYCEROL |
CN102066297B (en) * | 2008-05-19 | 2013-10-16 | 罗狄亚聚酰胺特殊品有限公司 | Method of purifying crude glycerol |
WO2010075616A1 (en) * | 2009-01-05 | 2010-07-08 | Serviço Nacional De Aprendizagem Industrial-Senai/Dr-Ba | Process for purifying light-coloured glycerol from biodiesel transesterification |
CN102471216A (en) * | 2009-07-01 | 2012-05-23 | 罗狄亚聚酰胺特殊品有限公司 | Process to obtain a mixture of lower carboxylic mono, di and triesters from raw glycerin |
CN102471216B (en) * | 2009-07-01 | 2014-11-12 | 罗狄亚聚酰胺特殊品有限公司 | Process to obtain a mixture of lower carboxylic mono, di and triesters from raw glycerin |
CN102596871A (en) * | 2009-09-11 | 2012-07-18 | 罗狄亚聚酰胺特殊品有限公司 | Process for the purification of crude glycerol |
WO2011030204A1 (en) * | 2009-09-11 | 2011-03-17 | Rhodia Poliamida E Especialidades Ltda | Process for the purification of crude glycerol |
US20120245398A1 (en) * | 2009-09-11 | 2012-09-27 | Rhodia Poliamida E Especialidades Ltda | Process for the purification of crude glycerol |
EP2295394A1 (en) * | 2009-09-11 | 2011-03-16 | Rhodia Poliamida E Especialidades Ltda | Process for the purification of crude glycerol |
WO2012034905A1 (en) * | 2010-09-15 | 2012-03-22 | Rhodia Operations | Process for producing dioxolane |
FR2964658A1 (en) * | 2010-09-15 | 2012-03-16 | Rhodia Operations | PROCESS FOR PRODUCING DIOXOLANE |
WO2012076759A1 (en) | 2010-12-10 | 2012-06-14 | Kemira Oyj | A method for recovery of organic acid from dilute aqueous solution |
US20140235878A1 (en) * | 2011-09-30 | 2014-08-21 | Rhodia Poliamida E Especialidades Ltda | Process for the production of a dioxolane compound from crude glycerol |
US9126967B2 (en) * | 2011-09-30 | 2015-09-08 | Rhodia Poliamida E Especialidades Ltda | Process for the production of a dioxolane compound from crude glycerol |
CN104926638A (en) * | 2015-05-05 | 2015-09-23 | 湖北省宏源药业科技股份有限公司 | Method and device for continuously concentrating glyoxylic acid |
WO2019092495A1 (en) * | 2017-11-09 | 2019-05-16 | Braskem S.A. | Process for the recovery of ketones and glycols from fermentation |
JP2021502088A (en) * | 2017-11-09 | 2021-01-28 | ブラスケム・エス・エー | How to recover ketones and glycols from fermentation |
CN110746270A (en) * | 2019-11-04 | 2020-02-04 | 江苏扬农化工集团有限公司 | Method for recycling epichlorohydrin wastewater |
CN110746270B (en) * | 2019-11-04 | 2023-06-06 | 江苏扬农化工集团有限公司 | Method for recycling epichlorohydrin wastewater |
FR3112964A1 (en) * | 2020-07-28 | 2022-02-04 | IFP Energies Nouvelles | LIQUID-LIQUID REACTIVE EXTRACTION PROCESS |
Also Published As
Publication number | Publication date |
---|---|
NL243096A (en) | 1900-01-01 |
DE1240525C2 (en) | 1967-11-23 |
DE1240525B (en) | 1967-05-18 |
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