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WO2001058851A1 - Derives d'acide n-(1-oxoalkyl)amino ou n-alkylaminocarbonyl polyhydroxyalcanecarboxylique - Google Patents

Derives d'acide n-(1-oxoalkyl)amino ou n-alkylaminocarbonyl polyhydroxyalcanecarboxylique Download PDF

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Publication number
WO2001058851A1
WO2001058851A1 PCT/EP2001/001309 EP0101309W WO0158851A1 WO 2001058851 A1 WO2001058851 A1 WO 2001058851A1 EP 0101309 W EP0101309 W EP 0101309W WO 0158851 A1 WO0158851 A1 WO 0158851A1
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WO
WIPO (PCT)
Prior art keywords
oxoalkyl
amino
alkylaminocarbonyl
polyhydroxyalkanecarboxylic
carbon atoms
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.)
Ceased
Application number
PCT/EP2001/001309
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English (en)
Inventor
Manfred Josef Bergfeld
Ludwig Eisenhuth
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.)
Akzo Nobel NV
Original Assignee
Akzo Nobel NV
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 Akzo Nobel NV filed Critical Akzo Nobel NV
Priority to AU2001240598A priority Critical patent/AU2001240598A1/en
Publication of WO2001058851A1 publication Critical patent/WO2001058851A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/49—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/528—Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- group

Definitions

  • the invention pertains to N-( ⁇ -oxoalkyl)amino or N-alkyiaminocarbonyl polyhydroxyalkanecarboxylic acid derivatives, a method for the preparation of same, and their use.
  • N-(1-oxoalkyl)amino or N-alkylaminocarbonyl polyhydroxyalkanecarboxylic acids of this invention are not known.
  • Fatty acid-N-alkylpolyhydroxyalkylamides are known as anionic detergents, for instance, from DE 4,443,643. These compounds, however, contain an N-(1-oxoalkyl)aminopolyhydroxyalkane moiety but not a carboxylic acid group.
  • polyhydroxyalkanecarboxylic acids are known, for instance from US 3,607,922, but these derivatives do not contain an N-(1-oxoalkyl)amino moiety.
  • glucose was oxidized to gluconic acid by oxygen in the presence of a platinum group metal catalyst. No utility of the product was given.
  • N-(1-oxoalkyl)amino or N-alkylaminocarbonyl poly- hydroxyalkanecarboxylic acid derivatives are very suitable for use as surfactants, especially in washing and cleaning processes. These compounds have improved water solubility while maintaining excellent biodegradability, and are therefore preferred over the known compounds for those uses.
  • the invention provides an N-(1-oxoalkyl)amino or N-alkylaminocarbonyl polyhydroxyalkanecarboxylic acid derivatives of the formulae
  • Ri is an alkyl group with 8-22 carbon atoms
  • R 2 is hydrogen or an alkyl group with 1-6 carbon atoms; A is an alkylene group with 3-5 carbon atoms substituted with at least two hydroxy groups; and X is hydrogen, an alkali metal, or an alkaline-earth metal.
  • X is an alkali metal or an alkaline-earth metal (ion).
  • Alkali metals comprise lithium, sodium, and potassium; alkaline-earth metals comprise magnesium and calcium.
  • the preferred counterions are alkali metals, particularly sodium and potassium.
  • each of the carbon atoms of moiety A is substituted with a hydroxy group.
  • hydroxy-substituted carbon atoms are chiral carbon atoms, which may possess the R or S configuration.
  • Compounds with all-R, all-S, or mixed- R,S configurations are considered to be part of this invention.
  • Optically active, racemic, and meso-isomers are also considered to be encompassed by this invention, as are diastereoisomers.
  • Compounds wherein moiety A is an alkylene group with 4 carbon atoms (butylene) are preferred.
  • Ri is an alkyl group with 8-22 carbon atoms, which optionally may be unsaturated.
  • alkyl groups including alkenyl groups
  • alkyl groups such as octyl, nonyl, decyl (capryl), undecyl, dodecyl (lauryl), tetradecyl (myristyl), pentadecyl (palmityl), hexadecyl (cetyl), octadecyl (stearyl), eicosanyl
  • Ri has 10-14 carbon atoms.
  • a most preferred compound according to the invention is the N-(1- oxoalkyl)amino or N-alkylaminocarbonyl polyhydroxyalkanecarboxylic acid and salts thereof, wherein Ri is an alkyl group with 12 carbon atoms.
  • dodecyl group in these preferred compounds can be present as a constituent of the coconut fatty moiety together with minor quantities of smaller and larger alkyl residues.
  • group R-i will then be a mixture of alkyl groups.
  • group R is mainly a C12 group, but it also contains alkyl groups with C10-18, and even minor quantities of residues from higher and lower fatty acids, such as caproic acid, may be present.
  • R-t is an alkyl group with 8-22 carbon atoms” therefore also covers mixtures of alkyl groups, the mean number of carbon atoms being 8-22.
  • R 2 is a hydrogen or an alkyl group with 1-6 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, pentyl, isopentyl, hexyl, and the like.
  • R 2 is hydrogen or a methyl group.
  • the invention further pertains to a method for the preparation of the N-(1- oxoalkyl)amino or N-alkylaminocarbonyl polyhydroxyalkanecarboxylic acid derivatives.
  • This method is characterized in that the primary hydroxy group of an alcohol of the formulae R 1 -CO-N(R 2 )-CH 2 -A-CH 2 OH or R ⁇ (R 2 )N-CO-A- CH 2 OH, wherein R , R 2 , and A have the previously given meanings, is oxidized to give the corresponding N-(1-oxoalkyl)amino or N-alkylaminocarbonyl polyhydroxyalkanecarboxylic acid (formula I), with oxygen in an aqueous medium with a pH>6 in the presence of a heterogeneous catalyst of group VIII of the periodic system.
  • fatty acid-N-alkylpolyhydroxyalkylamides are derived from reducing sugars, such as glucose or ⁇ -gluconolactone, by reductive amination. These methods are well- known, for instance from US 1 ,985,424, US 2,016,962, US 2,703,798, WO 92/06072, and WO 92/06984.
  • the oxidation of these alkyiamides is performed with oxygen. Pure oxygen can be used, but also oxygen-containing gases such as air.
  • the reaction is further performed in the presence of a heterogeneous catalyst of Group VIII of the periodic system.
  • the catalyst is a heterogeneous catalyst on the basis of palladium or platinum.
  • a platinum catalyst is preferred, such as Adam's catalyst, platinum on active carbon, or platinum on aluminum oxide.
  • the catalyst may contain promotors, such as Bi and Pb.
  • the reaction temperature and pressure are not very critical. Convenient temperatures are room temperature and higher. Usually the reaction is performed at 40-100°C, and more preferably at 50-80°C. Pressures can be from atmospheric to 10 MPa, and higher. Preferably, the reaction is performed at atmospheric pressure.
  • the invention is further illustrated by the examples.
  • a Pt/C catalyst (10% Pt on active carbon) were dispersed in 270 ml of water by gentle stirring. After flushing with oxygen, the flask was heated to 70°C and the reaction was started after intensive stirring. From a gas burette oxygen was added to supply the reacted oxygen and to maintain the atmospheric pressure. During the reaction the pH was maintained at 8 by the addition of 1 N aqueous sodium hydroxide.
  • cocoyl group mainly consists of dodecyloxo and tridecyloxo moieties.
  • Example 1 The reaction of Example 1 was repeated with 19.3 g of compound I and 3.5 g of a Pt/C catalyst (10% Pt on active carbon) in 270 ml of water. The pH was maintained at 9 by the addition of 1 N aqueous sodium hydroxide. After the uptake of 50 mmoles of sodium hydroxide the reaction was stopped and 20.1 g of the same product as in Example 1 were obtained.
  • Example 1 The reaction of Example 1 was repeated with 11.6 g of compound I and 1.75 g of a Pt/C catalyst (10% Pt on active carbon) in 270 ml of water. The pH was maintained at 8 by the addition of 1 N aqueous sodium hydroxide. After a reaction time of 6.5 h, 12.6 g of the same product as in Example 1 were obtained.
  • Example 1 in a purity of 95%.
  • Example 5 In the manner as described in Example 1 , 27.9 g of compound II and 7 g of a Pt/C catalyst (10% Pt on active carbon) were dispersed in 450 ml of water. At a reaction temperature of 70°C, the pH was maintained at 8 by the addition of 1 N aqueous sodium hydroxide. After a reaction time of 4.5 h, 75 mmoles of sodium hydroxide had been used, after which the reaction was stopped. The bulk of the reaction mixture was removed from the flask through a filtering candle. The catalyst together with a minor quantity of reaction product remained in the flask.
  • Example 6 The reaction of Example 1 was repeated with 11.5 g of
  • the products were found to be completely biodegradable.

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

Abstract

La présente invention concerne un dérivé d'acide N-(1-oxoalkyl)amino ou N-alkylaminocarbonyl polyhydroxyalcane carboxylique de formule R1-CO-N(R2)-CH2-A-COOX or R1(R2)N-CO-A-COOX, dans laquelle : R1 est un groupe alkyle ayant 8-22 atomes de carbone ; R2 est hydrogène ou un groupe alkyle ayant 1-6 atomes de carbone ; A est un groupe alkylène ayant 3-5 atomes de carbone substitué avec au moins deux groupes hydroxy ; et X est hydrogène, un métal alcalin, ou un métal alcalino-terreux. Cette invention concerne également un procédé permettant de préparer ledit dérivé par oxydation de l'alcool primaire correspondant avec de l'oxygène dans un milieu aqueux ayant un pH ⊃ 6 en présence d'un catalyseur hétérogène faisant partie du groupe VIII du tableau périodique des éléments. Les composés ainsi obtenus peuvent être utilisés comme agents tensioactifs.
PCT/EP2001/001309 2000-02-08 2001-02-05 Derives d'acide n-(1-oxoalkyl)amino ou n-alkylaminocarbonyl polyhydroxyalcanecarboxylique Ceased WO2001058851A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001240598A AU2001240598A1 (en) 2000-02-08 2001-02-05 N-(1-oxoalkyl)amino or n-alkylaminocarbonyl polyhydroxyalkanecarboxylic acid derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP00200422 2000-02-08
EP00200422.4 2000-02-08

Publications (1)

Publication Number Publication Date
WO2001058851A1 true WO2001058851A1 (fr) 2001-08-16

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AU (1) AU2001240598A1 (fr)
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3530646A1 (fr) * 2018-02-23 2019-08-28 Koninklijke Coöperatie Cosun U.A. Composé actif en surface

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2703798A (en) * 1950-05-25 1955-03-08 Commercial Solvents Corp Detergents from nu-monoalkyl-glucamines
US3607922A (en) * 1966-10-13 1971-09-21 Johnson Matthey Co Ltd Catalytic oxidation of glucose
EP0315857A1 (fr) * 1987-11-10 1989-05-17 Henkel Kommanditgesellschaft auf Aktien Procédé de préparation d'acides gras en C12-C40-alpha-ramifiés
DE4107987A1 (de) * 1991-03-13 1992-09-17 Henkel Kgaa Verfahren zur herstellung von 3-hydroxypropionsaeure
EP0649836A1 (fr) * 1993-10-25 1995-04-26 Kao Corporation Procédés pour la préparation d'un N-(chaîne longue acyl) amino acide et ses sels, amidonitrile intermédiaire et procédé de sa préparation
DE4443643A1 (de) * 1994-12-08 1996-06-13 Henkel Kgaa Anionische Detergensgemische

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2703798A (en) * 1950-05-25 1955-03-08 Commercial Solvents Corp Detergents from nu-monoalkyl-glucamines
US3607922A (en) * 1966-10-13 1971-09-21 Johnson Matthey Co Ltd Catalytic oxidation of glucose
EP0315857A1 (fr) * 1987-11-10 1989-05-17 Henkel Kommanditgesellschaft auf Aktien Procédé de préparation d'acides gras en C12-C40-alpha-ramifiés
DE4107987A1 (de) * 1991-03-13 1992-09-17 Henkel Kgaa Verfahren zur herstellung von 3-hydroxypropionsaeure
EP0649836A1 (fr) * 1993-10-25 1995-04-26 Kao Corporation Procédés pour la préparation d'un N-(chaîne longue acyl) amino acide et ses sels, amidonitrile intermédiaire et procédé de sa préparation
DE4443643A1 (de) * 1994-12-08 1996-06-13 Henkel Kgaa Anionische Detergensgemische

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3530646A1 (fr) * 2018-02-23 2019-08-28 Koninklijke Coöperatie Cosun U.A. Composé actif en surface
WO2019162469A1 (fr) * 2018-02-23 2019-08-29 Coöperatie Koninklijke Cosun U.A. Composé tensioactif

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