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 aqueoussolution

Info

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
Application number
GB29421/59A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of GB933714A publication Critical patent/GB933714A/en
Expired legal-status Critical Current

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

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.
GB29421/59A 1958-09-09 1959-08-28 Improvements in or relating to the recovery of organic compounds from dilute aqueoussolution Expired GB933714A (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Cited By (42)

* Cited by examiner, † Cited by third party
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
DE1240525B (en) 1967-05-18
DE1240525C2 (en) 1967-11-23

Similar Documents

Publication Publication Date Title
GB933714A (en) Improvements in or relating to the recovery of organic compounds from dilute aqueoussolution
US5892107A (en) Method for the production of levulinic acid
JP2007518778A (en) Method for reactive extraction of levulinic acid
NO152371C (en) PROCEDURE FOR THE PREPARATION OF ANCIENT OR APPROXIMATED Aqueous ACID
KR970015553A (en) Method for purifying acetic acid
KR920021159A (en) Comipora mukul extract and its therapeutic application
CN101967083B (en) Method for separating and refining polyprenol in ginkgo biloba extract
Das et al. Molecular iodine in protection and deprotection chemistry
NO794080L (en) PROCEDURE FOR THE PREPARATION OF ANCIENT OR APPROXIMATED Aqueous ACID.
JP2002517477A5 (en)
IE38656B1 (en) A process for the production of percarboxylic acid solutions in organic solvents
DE1793679A1 (en) New intermediates for the production of optically active 13-alkyl-gonapentaenes
Maerker et al. Direct cleavage of internal epoxides with periodic acid
EP0583907A3 (en) Process for producing trioxan
JPS56134526A (en) Recovery of cobalt catalyst
Umezawa et al. Synthetic Studies of the Derivatives of Nitroacetic Acid. I. The Preparation of Nitroacetic Ester and the Synthesis of α, β-Unsaturated α-Nitrocarboxylic Esters
Filachione et al. Preparation of Esters by Reaction of Ammonium Salts with Alcohols1b
Golovina et al. Structure and stereochemistry of lapiferinin
ES495482A0 (en) PROCEDURE FOR THE RECOVERY OF CARBOXYLIC ACIDS FROM MIXTURES CONTAINING GLYCOL ESTERS DERIVED FROM THESE ACIDS
Sweet et al. The preparation of methyl 4-deoxy-3-O-methyl-α, β-DL-threo-pentopyranoside
Foster et al. 1009. Reaction of L-threitol with acetone
SU116928A1 (en) The method of producing esters of isoborneol
GB1510219A (en) Continuous process for the purification of glyoxal
US2359126A (en) Process of obtaining purified flavanone glucosides
SU386939A1 (en) METHOD OF OBTAINING ETHYL ETHER 1-METHYLPIPERIDIN-3-CARBIC ACID