EP0689530A1 - Procede de preparation d'acide monochloracetique a teneur reduite en acide dichloracetique - Google Patents

Procede de preparation d'acide monochloracetique a teneur reduite en acide dichloracetique

Info

Publication number
EP0689530A1
EP0689530A1 EP94911130A EP94911130A EP0689530A1 EP 0689530 A1 EP0689530 A1 EP 0689530A1 EP 94911130 A EP94911130 A EP 94911130A EP 94911130 A EP94911130 A EP 94911130A EP 0689530 A1 EP0689530 A1 EP 0689530A1
Authority
EP
European Patent Office
Prior art keywords
monochloroacetic acid
acid
reduced
dichloroacetic
monochloroacetic
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Withdrawn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
EP94911130A
Other languages
German (de)
English (en)
Inventor
Alfred Struve
Uwe Ploog
Günter Uphues
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0689530A1 publication Critical patent/EP0689530A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • 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
    • C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification

Definitions

  • the invention relates to a process for the preparation of a monochloroacetic acid with a low content of dichloroacetic acid, in which the contaminated acid is subjected to a temperature treatment in the presence of base metals and then distilled, and the use of the purified acid for the production of amphoteric or zwitterionic surfactants.
  • Amphoteric or zwitterionic surfactants are extremely skin-friendly and have excellent cleaning properties. They are therefore particularly suitable for the assembly of a large number of surface-active products. In the simplest case, their preparation is based on secondary or tertiary amines, which are reacted with sodium chloroacetate to give alkyl betaines. The reaction of fatty acid amidoamines or imidazolines with sodium chloroacetate leads to the formation of amphoteric surfactants of the type Glycinates; If acrylic acid ester is used as the alkylating agent, aminopropionates are formed. Compounds of the type mentioned are described in a large number of review articles, of which only Parf.Cos .Arom. 70. 67 (1986), HAPPI, 70, (Nov. 1986) and Soap Cosm.Chem.Spec. 46, (Apr. 1990).
  • a particular problem in the production of alkyl betaines and glycinates is the quality of the monochloroacetic acid or its sodium salts to be used as the alkylating agent, since these usually have an undesirable content of approx. 2000 to 3000 ppm dichloroacetic acid due to the production process.
  • amphoteric surfactant manufacturers have a need for a qualitatively improved monochloroacetic acid whose dichloroacetic acid content should be a maximum of 200 to 500.
  • the object of the invention was therefore to develop a process for the production of a monochloroacetic acid with a reduced content of dichloroacetic acid which is free from the disadvantages described. Description of the invention
  • the invention relates to a process for the preparation of monochloroacetic acid with a reduced dichloroacetic acid content, in which the crude monochloroacetic acid is subjected to a temperature treatment in the presence of an infinite metal and the reaction product is then distilled.
  • Suitable base metals are substances which easily form salts with monochloroacetic acid with the elimination of hydrogen. Typical examples are magnesium, aluminum, zinc, tin, lead, iron, nickel and cobalt. The use of zinc and tin in the form of powder, chips, cut or granules is preferred.
  • the base metals can usually be used in amounts of 0.25 to 5, preferably 1 to 2,% by weight, based on the monochloroacetic acid. Heat treatment
  • the temperature treatment can be carried out in the range from 100 to 140, in particular 120 to 130 ° C., preferably in an inert gas atmosphere for the discharge of gaseous hydrogen released. To do this, it is sufficient to mix the contaminated monochloroacetic acid with the base metals and to stir it for a period of 0.1 to 5, preferably 0.5 to 2, hours. Subsequently, the purified monochloroacetic acid can be distilled off from the reaction mixture, usually at temperatures in the range from 100 to 135 ° C. and under a reduced pressure in the range from 50 to 500 mbar. The distillative removal is not a further purification step, rather it is a simple and efficient way of separating the monochloroacetic acid purified by the temperature treatment from the residue - essentially salts and optionally catalyst residues.
  • the monochloroacetic acid obtainable by the process according to the invention has a content of less than 1000, preferably less than 500 and in particular less than 300 ppm dichloroacetic acid and therefore also meets very high quality requirements.
  • Another object of the invention therefore relates to their use as alkylating agents for the production of amphoteric or zwitterionic surfactants, in particular of the alkyl betaines and glycinates type.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

On peut produire un acide monochloracétique à teneur réduite en acide dichloracétique en soumettant l'acide monochloracétique brut à un traitement thermique en présence d'un métal non précieux, puis en distillant le produit de la réaction. L'acide monochloracétique purifié est particulièrement utile comme agent alkylant afin de produire des agents tensioactifs amphotères ou zwittérioniques.
EP94911130A 1993-03-18 1994-03-09 Procede de preparation d'acide monochloracetique a teneur reduite en acide dichloracetique Withdrawn EP0689530A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4308793A DE4308793A1 (de) 1993-03-18 1993-03-18 Verfahren zur Herstellung von Monochloressigsäure mit vermindertem Dichloressigsäuregehalt
DE4308793 1993-03-18
PCT/EP1994/000717 WO1994021588A1 (fr) 1993-03-18 1994-03-09 Procede de preparation d'acide monochloracetique a teneur reduite en acide dichloracetique

Publications (1)

Publication Number Publication Date
EP0689530A1 true EP0689530A1 (fr) 1996-01-03

Family

ID=6483219

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94911130A Withdrawn EP0689530A1 (fr) 1993-03-18 1994-03-09 Procede de preparation d'acide monochloracetique a teneur reduite en acide dichloracetique

Country Status (3)

Country Link
EP (1) EP0689530A1 (fr)
DE (1) DE4308793A1 (fr)
WO (1) WO1994021588A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0842756A1 (fr) * 1996-11-08 1998-05-20 Milliken Research Corporation Essuie-mains en rouleau joint par ultrasons

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19545134C2 (de) 1995-12-04 1998-02-26 Henkel Kgaa Verfahren zur Herstellung hellfarbiger Betaine
MX2017011678A (es) 2015-03-17 2017-11-06 Akzo Nobel Chemicals Int Bv Proceso para la purificacion de acido monocloroacetico.

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5527156A (en) * 1978-08-17 1980-02-27 Nippon Oil & Fats Co Ltd Purification of fatty acid
JPS5545614A (en) * 1978-09-27 1980-03-31 Nippon Oil & Fats Co Ltd Purification of aliphatic acid
EP0465844B1 (fr) * 1990-06-11 1996-04-10 MITSUI TOATSU CHEMICALS, Inc. Procédé de purification d'acide 2-chloropropionique

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9421588A1 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0842756A1 (fr) * 1996-11-08 1998-05-20 Milliken Research Corporation Essuie-mains en rouleau joint par ultrasons

Also Published As

Publication number Publication date
WO1994021588A1 (fr) 1994-09-29
DE4308793A1 (de) 1994-09-22

Similar Documents

Publication Publication Date Title
EP0071787B1 (fr) Catalyseurs d'hydrogénation à base de ruthénium-carbone, leur préparation et leur utilisation dans l'hydrogénation de composés carbonylés insaturés
EP1971567B1 (fr) Procede de purification de (meth)acrylate
WO2004054948A1 (fr) Procede de production de 1,6-hexanediol
EP0915890B1 (fr) Procede de preparation d'alcoxysilanes
EP0671382B1 (fr) Carboxybetaines et alkylsulfobetaines fluorées ainsi que leurs mélanges avec les fluoroalkylamines saturées
EP1266882A1 (fr) Procédé de préparation d'esters de l'acide cyclohexanedicarboxylique
EP0689530A1 (fr) Procede de preparation d'acide monochloracetique a teneur reduite en acide dichloracetique
EP1299191B1 (fr) Catalyseurs de nickel metalliques d'hydrogenation, leur production et leur utilisation
EP2373617B1 (fr) Mélanges d'acide itaconique ou de dérivés d'acide itaconique et d'amines primaires pour la production de 1,3- et de 1,4-alkylméthylpyrrolidones
EP1541541B1 (fr) Procédé pour la préparation d' alcoolates alkalino-terreux purs
EP0089417B1 (fr) Procédé pour la préparation du phtalide
DE4290290C2 (de) Verfahren zur Herstellung von 2-Chlor-5-aminomethylpyridin
EP0723952B1 (fr) Procédé pour la purification d'amines grasses alkylées méthyliques tertiaires
EP0034804A2 (fr) Procédé de préparation de cétones supérieures saturées
EP0030269B1 (fr) Procédé de récupération du catalyseur à métal précieux dans la préparation des uréthanes aromatiques
DE4037021C2 (de) Eisen, Aluminium und gegebenenfalls Calcium enthaltendes Silicium zur Verwendung bei der Umsetzung zu Chlorsilanen oder zu Organosilanen und Verfahren zu dessen Herstellung
DE19610323C2 (de) Verfahren zur Herstellung von N-Lauroyl-L-glutaminsäure-di-n-butylamid
EP0316761A2 (fr) Procédé pour la préparation de diméthyl-N,N-diaminopropane
EP3269718A1 (fr) Prodédé pour la déprotection d'un carbapénème par hydrogénation catalytique hétérogène avec hydrogène en présence d'un amine organique
DE3200783C2 (de) Verfahren zur Herstellung von gegebenenfalls substituierten cis,cis-1,3-Cyclooctadienen durch Isomerisierung von gegebenenfalls substituierten 1,4- oder 1,5-Cyclooctadienen
DE1518496A1 (de) Verfahren zur Herstellung von Aminen
DE3137092A1 (de) Verfahren zur herstellung von 4-aminomethyl-cyclohexancarbonsaeure oder eines mineralsaeuresalzes derselben
EP0158953B1 (fr) Triamines, un procédé de leur préparation et leur utilisation à titre d'agents réticulants or durcissants pour matières plastiques ou précurseurs ayant des goupes d'époxydes ou d'isocyanates
EP3512830A1 (fr) Procédé d'hydrogénation d'un mélange en présence d'une amine incolore
EP0728722B1 (fr) Procédé pour la production d'hydroxyméthylcyclopropane

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19950911

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): DE FR GB IT

17Q First examination report despatched

Effective date: 19961202

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN

18W Application withdrawn

Withdrawal date: 19970123