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WO1996009279A1 - Procede de production d'acides n-acylaminocarboxyliques et n-acylaminosulfoniques libres - Google Patents

Procede de production d'acides n-acylaminocarboxyliques et n-acylaminosulfoniques libres Download PDF

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Publication number
WO1996009279A1
WO1996009279A1 PCT/EP1995/003585 EP9503585W WO9609279A1 WO 1996009279 A1 WO1996009279 A1 WO 1996009279A1 EP 9503585 W EP9503585 W EP 9503585W WO 9609279 A1 WO9609279 A1 WO 9609279A1
Authority
WO
WIPO (PCT)
Prior art keywords
acids
alkali metal
free
metal salts
acid
Prior art date
Application number
PCT/EP1995/003585
Other languages
German (de)
English (en)
Inventor
Beate Strecker
Alfred Oftring
Dieter Hertel
Georg Schuh
Original Assignee
Basf Aktiengesellschaft
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 Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to EP95932723A priority Critical patent/EP0783485A1/fr
Priority to JP8510566A priority patent/JPH10505845A/ja
Publication of WO1996009279A1 publication Critical patent/WO1996009279A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • 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
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups

Definitions

  • the present invention relates to an improved process for the preparation of free N-acylaminocarboxylic acids and free N-acylaminosulfonic acids from their solvent-free alkali metal salts by precipitation with aqueous acids.
  • the alkali metal salts of N-acylaminocarboxylic or sulfonic acids are produced on an industrial scale mainly by Schotten-Baumann reaction of corresponding acyl halides with the alkali metal salts of the underlying aminocarboxylic or sulfonic acids in aqueous alkaline milieu. Since it is advantageous for some areas of application to use the N-acylaminocarboxylic or sulfonic acids as free acids, these are obtained by precipitation from the aqueous alkali metal salt solutions with strong acids prepared in this way.
  • the addition of the free acids according to the invention means that the N-acylaminocarbon or sulfonic acid alkali metal salts are converted into a free-flowing and pumpable state.
  • the addition of the free acids does not pose any problems in this regard, since - in contrast to the addition of water - this can also take place at temperatures of more than 100 ° C.
  • the viscosity of e.g. N-oleoylsarcosine sodium is at 120 to 130 ° C at less than 5000 mPas.
  • the addition of the free N-acylaminocarboxylic or sulfonic acids to the alkali metal salts is therefore preferably carried out at temperatures from 90 to 160 ° C., in particular 95 to 130 ° C.
  • the mixture of free acids and their alkali metal salts thus obtained can now be easily taken up in water and completely converted into the free acid form by adding acids. It has proven to be advantageous to work at a higher temperature, for example at 70 to 95 ° C. A simultaneous addition of acid and water is also advantageous here.
  • Suitable acids for converting the alkali metal salts into their free acid form are in particular mineral acids such as sulfuric acid, phosphoric acid or hydrochloric acid, but also organic acids, for example carboxylic acids such as formic or acetic acid, which are usually added in such an amount that a pH -Value in the range of about 0 to 3, in particular 1 to 2, sets. This usually results in milky, creamy emulsions.
  • phase separation aids for example ketones such as isobutyl methyl ketone or methyl ethyl ketone, alkanols such as n-butanol, isobutanol or sec-butanol, ethers such as methyl tert-butyl ether or diisopropyl ether, acetic acid ci- to C 4 -alkyl esters, C 1 -C 4 -propionic acid alkyl esters or acetoacetic esters, which can be added simultaneously with the acids or after the emulsion has formed, at a slightly elevated temperature, for example at 40 to 70 ° C.
  • phase separation aids are usually low-boiling, water-immiscible or poorly miscible compounds that can be used inexpensively on an industrial scale.
  • the alkali metal salts of N-acylaminocarboxylic acids are the sodium or potassium salts of aliphatic aminocarboxylic acids having 2 to 10 C atoms, preferably 3 to 6 C atoms, in particular valine, leucine, norleucine, glycine , Alanine, ß-alanine, ⁇ -amino-caproic acid, ⁇ -aminoisobutyric acid, sarcosine (N-methylglycine), aspartic acid, glutamic acid or iminodiacetic acid, with an acyl radical derived from saturated or unsaturated C ⁇ to C 3 o * monocarboxylic acids.
  • the saturated or unsaturated C 1 -C 3 o -monocarboxylic acids which are preferably the basis of the acyl radicals are, in particular, saturated or unsaturated Cg- to C o * -monocarboxylic acids such as lauric acid, myristic acid, palmitic acid, stearic acid, 01-acid, linoleic acid, lmolenic acid or mixtures of these naturally Coming long-chain fatty acids such as coconut fatty acid, palm oil fatty acid, palm kernel oil fatty acid, taig fatty acid, soybean oil fatty acid, sunflower oil fatty acid or rapeseed oil fatty acid as well as corresponding synthetically produced C 8 - to C o-monocarboxylic acids or mixtures thereof.
  • saturated or unsaturated Cg- to C o * -monocarboxylic acids such as lauric acid, myristic acid, palmitic acid, stearic acid, 01-acid, linole
  • Example 2 310 g of the same N-oleoyl sarcosine sodium as in Example 1 were mixed with 70 g of N-oleoyl sarcosine as described in Example 2. The mixture thus obtained was metered into a mixture of 600 g of water and 90 g of sulfuric acid (96% by weight) at about 80 to 95 ° C. under a slight nitrogen pressure. The mixture reacted at the same rate at which it was introduced into the aqueous sulfuric acid. The product was isolated as described in Example 3. The N-oleoyl sarcosine was obtained as an orange-brown oil in a weight of 387 g (91% of theory. Yield).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de production d'acides N-acylaminocarboxyliques et N-acylaminosulfoniques libres à partir de leurs sels de métaux alcalins produits sans solvant, par précipitation avec des acides aqueux. Ce procédé consiste à ajouter aux sels de métaux alcalins, 5 à 100 % en poids, par rapport à la proportion de sels de métaux alcalins, d'acides N-acylaminocarboxyliques et N-acylaminosulfoniques libres correspondants, avant le mélange avec les acides aqueux.
PCT/EP1995/003585 1994-09-23 1995-09-12 Procede de production d'acides n-acylaminocarboxyliques et n-acylaminosulfoniques libres WO1996009279A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP95932723A EP0783485A1 (fr) 1994-09-23 1995-09-12 Procede de production d'acides n-acylaminocarboxyliques et n-acylaminosulfoniques libres
JP8510566A JPH10505845A (ja) 1994-09-23 1995-09-12 遊離のｎ−アシルアミノカルボン酸及びｎ−アシルアミノスルホン酸の製法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4433976.3 1994-09-23
DE19944433976 DE4433976A1 (de) 1994-09-23 1994-09-23 Verfahren zur Herstellung von freien N-Acylaminocarbon- und -sulfonsäuren

Publications (1)

Publication Number Publication Date
WO1996009279A1 true WO1996009279A1 (fr) 1996-03-28

Family

ID=6528986

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/003585 WO1996009279A1 (fr) 1994-09-23 1995-09-12 Procede de production d'acides n-acylaminocarboxyliques et n-acylaminosulfoniques libres

Country Status (4)

Country Link
EP (1) EP0783485A1 (fr)
JP (1) JPH10505845A (fr)
DE (1) DE4433976A1 (fr)
WO (1) WO1996009279A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2026623A1 (en) * 1969-07-23 1971-02-11 Fatty acid sarcosides bleaching process
US3836551A (en) * 1970-01-30 1974-09-17 Roehm Gmbh Method for making salts of n-acylamino carboxylic acids
EP0033392A1 (fr) * 1980-02-02 1981-08-12 Hüls Troisdorf Aktiengesellschaft Procédé d'acylation d'acides aminés
DE4408957A1 (de) * 1994-03-17 1995-09-21 Basf Ag Verfahren zur Herstellung von N-Acylaminocarbonsäuren und N-Acylaminosulfonsäuren sowie deren Alkalimetallsalzen

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2026623A1 (en) * 1969-07-23 1971-02-11 Fatty acid sarcosides bleaching process
US3836551A (en) * 1970-01-30 1974-09-17 Roehm Gmbh Method for making salts of n-acylamino carboxylic acids
EP0033392A1 (fr) * 1980-02-02 1981-08-12 Hüls Troisdorf Aktiengesellschaft Procédé d'acylation d'acides aminés
DE4408957A1 (de) * 1994-03-17 1995-09-21 Basf Ag Verfahren zur Herstellung von N-Acylaminocarbonsäuren und N-Acylaminosulfonsäuren sowie deren Alkalimetallsalzen

Also Published As

Publication number Publication date
EP0783485A1 (fr) 1997-07-16
DE4433976A1 (de) 1996-03-28
JPH10505845A (ja) 1998-06-09

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