EP1232142A1 - Procede pour isoler des sulfonates de phenylesters d'acide amido contenus dans des melanges eau-solvant - Google Patents

Procede pour isoler des sulfonates de phenylesters d'acide amido contenus dans des melanges eau-solvant

Info

Publication number
EP1232142A1
EP1232142A1 EP00974530A EP00974530A EP1232142A1 EP 1232142 A1 EP1232142 A1 EP 1232142A1 EP 00974530 A EP00974530 A EP 00974530A EP 00974530 A EP00974530 A EP 00974530A EP 1232142 A1 EP1232142 A1 EP 1232142A1
Authority
EP
European Patent Office
Prior art keywords
mixture
solvent
water
oxyalkanoyl
sulfophenyl
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.)
Withdrawn
Application number
EP00974530A
Other languages
German (de)
English (en)
Inventor
Rainald Forbert
Wilhelm Schunk
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.)
Siemens Axiva GmbH and Co KG
Original Assignee
Siemens Axiva GmbH and Co KG
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 Siemens Axiva GmbH and Co KG filed Critical Siemens Axiva GmbH and Co KG
Publication of EP1232142A1 publication Critical patent/EP1232142A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/42—Separation; Purification; Stabilisation; Use of additives
    • C07C303/44—Separation; Purification

Definitions

  • the invention relates to a process for isolating amido acid phenyl ester sulfonates from water-solvent mixtures.
  • Amidosaurephenylestersulfonate serve as bleach activators in detergents and other cleaning agents that contain bleach. These activators have several beneficial properties such as excellent bleaching performance with minimal damage to fabric colors, good compatibility with washing machines and a good odor profile in the laundry.
  • Amidosaurephenylestersulfonate can also be synthesized from relatively inexpensive and readily available substances. Many different synthetic routes are known from the prior art, such as. B. in WO 95/07882, WO 96/28417. WO 99/09004 describes a method for producing and
  • the amido acid phenyl ester sulfonate is present after the reaction in a mixture of water, solvent and by-products.
  • the amido acid phenyl ester sulfonate is present in a mixture of water, solvent, by-products and at least one catalyst.
  • Other synthetic routes and purification routes are conceivable, from which a mixture of amido acid phenyl ester sulfonate, water, solvent, by-products and optionally other components, such as. B. catalysts results.
  • the invention was therefore based on the object of a method for isolating
  • amido acid phenyl ester sulfonate from a mixture with water, solvent, by-products and possibly other components which on the one hand does not have the disadvantage of the very slow mechanical separation of the product and on the other hand achieves sufficiently high purities.
  • this object is achieved by a method which comprises the following steps:
  • the 4-sulfophenyl - [(1-oxyalkanoyl) amino] alkanoate has the general structural formula
  • n is an integer between 1 and 26, preferably between 1 and 10, very particularly preferably 5.
  • R., and R 2 are independently selected identically or differently from hydrogen, unsubstituted or substituted straight-chain or branched C to C 20 alkyl, unsubstituted or substituted C 3 to C 8 cycloalkyl, C 3 to C 8 alkenyl, C 3 to C 8 alkynyl and C B to C 14 aryl.
  • the unsubstituted or substituted C 3 to C 8 cycloalkyl groups mentioned above represent cycloaliphatic hydrocarbon groups containing 3 to 8 carbon atoms in the ring, preferably 5 to 6 carbon atoms, and these cycloalkyl groups can be substituted with one or two of C to C 4 -alkyl, C, - to C 4 -alkoxy, hydroxy or C, - to C 4 -alkaneoxy.
  • the C 3 to C 8 alkenyl and C 3 to C 8 alkynyl groups represent straight-chain or branched hydrocarbon radicals, the 3 to 8 carbon atoms in the chain and a carbon-carbon double bond or a carbon-carbon - Triple binding included.
  • aryl is used to include carboxyl aryl groups containing up to 14 carbon atoms, e.g., phenyl and naphthyl, and those substituted with one or two groups selected from C, - bis C 4 -alkyl, C, - to C 4 -alkoxy, C to C 4 -alkoxycarbonyl, C r to C 4 -alkaneoxy, C, - to C 4 -
  • aryl is also used to include heterocyclic aryl groups such as a 5- or 6-part heterocyclic ring containing an oxygen atom and / or a sulfur atom and / or up to three nitrogen atoms "The heterocyclic aryl ring may optionally be attached to one or two phenyl rings or another 5- or 6-part heteroaryl ring.
  • ring systems include: thienyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl , Oxazolyl, isoxazolyl, triazolyl, thiadiazolyl, oxadiazolyl, tetrazolyl, thiatriazolyl, oxatriazolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, thiazinyl, oxazinyl, triazinyl, thiadizinyl, oxadiazinyl, dithiazinyl, dioxad
  • Tetrazinyl Tetrazinyl, Thiatriazinyl, Oxatriazinyl, Dithiadiazinyl, Imidazolinyl, Dihydropyhdyl, Tetrahydropyridyl, Tetrazolo- [1, 5b] pyridazinyl and -purinyl, Benzoxazolyl, Benzothiazolyl, Benzimidazolyl, Indolyl and the like or such rings according to those mentioned above with one or more of those according to the above Definition of the term "aryl" are substituted.
  • aryl contains arylene groups.
  • arylene is used in such a way that it stands for divalent carboxylic aryl hydrocarbon portions which contain up to 14 carbon atoms, for example o-, m-, p- Phenylene, and those which are substituted by one or two groups from C to C 4 alkyl, C to C 4 alkoxy or a halogen.
  • ⁇ And R 2 very particularly preferably represent hydrogen.
  • R3 stands for straight-chain or branched aliphatic, cycloaliphatic or aromatic radical which contains 5 to 25, preferably 7 to 9, particularly preferably 8 carbon atoms and can contain a carboxylic acid or a carboxylic acid ester. Suitable examples of R 3 are heptyl, octyl, nonyl, decyl, undecyl, pentadecyl, heptadecyl, 8-heptadecenyl, 8,11-heptadecadienyl, docosanyl, p-carboxybenzyl, o-carboxybenzyl, m-carboxybenzyl, carboxyethyl,
  • R 3 very particularly preferably represents octyl.
  • R 4 represents hydrogen, methyl, ethyl, propyl or isopropyl, very particularly preferably hydrogen.
  • M stands for hydrogen, ammonium or an alkali metal, very particularly preferably for sodium.
  • the method according to the invention is generally suitable for isolating substances of the structural formula given above.
  • Preferred substances are p-substituted benzenesulfonates.
  • the organic solvent in step a) is selected from the series of solvents which are compatible with the starting materials from the preparation of 4-sulfophenyl - [(1-oxyalkanoyl) amino] alkanoate by one of the processes disclosed in the WO documents cited at the beginning ( ie hardly or not reactive, i.e. largely inert).
  • the range of solvents that can be used include polar aprotic solvents such as N, N-dimethylacetamide and dimethyl sulfoxide.
  • the organic solvent preferably also belongs to the group of solvents which preferably distill off in vacuo in the presence of water.
  • the organic solvent can also be an aliphatic, cyclic or aromatic hydrocarbon, an ether, an ester, a ketone or a chlorinated hydrocarbon, preferably an alkane, cycloalkane, alkylbenzene, alkyl ether, alkyl acetate, alkyl ketone, chloroalkane or chlorobenzene, particularly preferably Hexane, heptane, octane, nonane, cyclohexane, toluene, xylene, diethyl ether, tetrahydrofuran, 1, 2-dimethoxyethane, ethyl acetate, n-butyl acetate, acetone,
  • Methyl ethyl ketone, dichloromethane, 1, 2-dichloroethane or dichlorobenzene can also be a mixture of two or more of the solvents mentioned above.
  • Starting mixture is preferably between 1:10 and 10: 1.
  • a bleaching agent a chemical defoamer and / or a mixture in any physical state, containing at least 95% water, can be added to the mixture.
  • the 4-sulfophenyl - [(1-oxyalkanoyl) amino] alkanoate can be washed with a washing system.
  • the washing system preferably consists of more than 99% by weight of water.
  • Weight ratio of solvent to water preferably reduced to below 1:10, particularly preferably to below 1:50, very particularly preferably to below 1: 100 before the separation of 4-sulfophenyl - [(1-oxyalkanoyl) amino] alkanoate from the mixture.
  • the removal of solvent can be carried out by all processes known to the person skilled in the art for this purpose, for example by distillation, rectification, stripping with steam or a membrane process.
  • the removal of solvent is preferably carried out by distillation or stripping with steam, particularly preferably by vacuum distillation at pressures between 10 and 200 mbar abs, very particularly preferably between 40 and 80 mbar abs.
  • the area limits mentioned should belong to the area here and throughout the registration.
  • Conditions and the solvent chosen can be used to withdraw different amounts of water from the mixture during the removal of solvent.
  • the temperature of the mixture during vacuum distillation is preferably between
  • the mixture Before separating 4-sulfophenyl - [(1-oxyalkanoyl) amino] alkanoate from the mixture, the mixture can be heated or cooled. Before the 4-sulfophenyl - [(1-oxyalkanoyl) amino] alkanoate is separated off, the mixture is preferably adjusted to temperatures between 10 ° C. and 40 ° C., particularly preferably between 15 ° C. and 30 ° C.
  • the separation of 4-sulfophenyl - [(1-oxyalkanoyl) amino] alkanoate from the mixture can be carried out by all processes known to the person skilled in the art for this purpose, for example by sedimentation, filtration or centrifugation.
  • the 4-sulfophenyl - [(1-oxyalkanoyl) amino] alkanoate is preferably separated from the mixture by vacuum filtration or decanting.
  • drying of the separated 4-sulfophenyl - [(1-oxyalkanoyl) amino] alkanoate can be carried out by all processes which are known to the person skilled in the art for this purpose. Drying in vacuo is preferably carried out at pressures between 10 and 200 mbar abs.
  • the method can be operated in whole or in part, batchwise or continuously, preferably the method is operated completely continuously.
  • vacuum distillation achieves a high purification of a 4-sulfophenyl - [(1-oxyalkanoyl) amino] alkanoate, although none of the impurities are distilled off to any appreciable extent with the solvent.
  • the advantages of the process according to the invention can essentially be seen in the fact that a 4-sulfophenyl - [(1-oxyalkanoyl) amino] alkanoate is isolated with very high purity and very good yield with little expenditure on equipment and energy.

Abstract

L'invention concerne un procédé permettant d'isoler du 4-sulfophényl-[1-oxyalcanoyl)amino]alcanoate contenu dans un mélange comprenant du 4-sulfophényl-1-oxyalcanoyl)amino]alcanoate, de l'eau et un solvant organique. Ce procédé se caractérise en ce qu'il est prévu a) de préparer un mélange initial contenant du 4-sulfophényl-[1-oxyalcanoyl)amino]alcanoate, de l'eau et un solvant organique ; b) d'extraire en totalité ou en partie le solvant du mélange de départ ; c) de séparer le 4-sulfophényl-[1-oxyalcanoyl)amino]alcanoate du mélange résiduel et d) de sécher le 4-sulfophényl-[1-oxyalcanoyl]alcanoate séparé.
EP00974530A 1999-11-25 2000-11-14 Procede pour isoler des sulfonates de phenylesters d'acide amido contenus dans des melanges eau-solvant Withdrawn EP1232142A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19956863 1999-11-25
DE1999156863 DE19956863A1 (de) 1999-11-25 1999-11-25 Verfahren zur Isolierung von Amidosäurephenylestersulfonaten aus Wasser-Lösungsmittel-Gemischen
PCT/EP2000/011221 WO2001038298A1 (fr) 1999-11-25 2000-11-14 Procede pour isoler des sulfonates de phenylesters d'acide amido contenus dans des melanges eau-solvant

Publications (1)

Publication Number Publication Date
EP1232142A1 true EP1232142A1 (fr) 2002-08-21

Family

ID=7930369

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00974530A Withdrawn EP1232142A1 (fr) 1999-11-25 2000-11-14 Procede pour isoler des sulfonates de phenylesters d'acide amido contenus dans des melanges eau-solvant

Country Status (4)

Country Link
EP (1) EP1232142A1 (fr)
AU (1) AU1279801A (fr)
DE (1) DE19956863A1 (fr)
WO (1) WO2001038298A1 (fr)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4985180A (en) * 1988-07-15 1991-01-15 E. I. Du Pont De Nemours And Company Process for preparing phenyl esters of substituted acids
EP0719249A1 (fr) * 1993-09-14 1996-07-03 The Procter & Gamble Company Synthese d'amido-acides a partir d'esters d'acide carboxylique et de sels d'amido-acides
US5523434A (en) * 1995-03-15 1996-06-04 The Procter & Gamble Company Synthesis of bleach activators
US5650527A (en) * 1995-06-05 1997-07-22 Eastman Chemical Company Preparation of amido ester compounds
JP2001515062A (ja) * 1997-08-20 2001-09-18 ザ、プロクター、エンド、ギャンブル、カンパニー アミド酸フェニルエステルスルホネートの調製方法および／または精製方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0138298A1 *

Also Published As

Publication number Publication date
WO2001038298A1 (fr) 2001-05-31
DE19956863A1 (de) 2001-06-21
AU1279801A (en) 2001-06-04

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