Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
  • C07H1/00—Processes for the preparation of sugar derivatives
  • C07H1/06—Separation; Purification
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
  • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
  • C07H15/02—Acyclic radicals, not substituted by cyclic structures
  • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical

Definitions

• the invention is in the field of surface-active compounds and relates to a new process for the preparation of special anionic surfactants which are distinguished by a reduced content of organic chlorine compounds.
• Carboxylation products of alk (en) yl oligoglycosides are anionic surfactants that have improved properties in the areas of foam formation, viscosity and sensor technology compared to the non-derivatized homologues. They are usually prepared by reacting the glycosides with halocarboxylic acid salts, especially sodium chloroacetate in aqueous solution. Depending on the amount of the alkylating agent used, some or all of the available hydroxyl groups are reacted.
• organochlorine compounds are not acceptable for use in the cosmetics sector in particular, since they can cause skin irritation or are otherwise undesirable for physiological reasons.
• the object of the present invention was therefore to provide an improved process for the preparation of alk (en) yl oligoglycoside carboxylic acid salts which provides products whose organochlorine compound content is below 35 ppm and preferably below 10 ppm. Description of the invention
• the invention relates to a new process for the preparation of aqueous pastes of alkyl and / or alkenyl oligoglycoside carboxylic acid salts with a reduced content of organic chlorine compounds, which is characterized in that the alkyl and / or alkenyl oligoglycosides are known in a manner known per se using halocarboxylic acids or their salts are reacted and the reaction products are subjected to an alkaline aftertreatment at temperatures in the range from 50 to 120 ° C.
• the alkaline post-treatment of the pastes can reduce the total content of organic chlorine compounds at least below 35 ppm, generally even below 10 ppm.
• Alkyl and alkenyl oligoglycosides which are suitable as one of the two starting materials for the preparation of the carboxylic acid salts, are known nonionic surfactants which follow the formula (I),
• R 1 is an alkyl and / or alkenyl radical having 4 to 22 carbon atoms
• G is a sugar radical having 5 or 6 carbon atoms
• p is a number from 1 to 10. They can be obtained according to the relevant procedures in preparative organic chemistry.
• the alkyl and / or alkenyl oligoglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose.
• the preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligoglucosides.
• alkyl and / or alkenyl oligoglycosides whose degree of oligomerization is less than 1.7 and is in particular between 1.2 and 1.4.
• the alkyl or alkenyl radical R 1 can be derived from primary alcohols having 4 to 11, preferably 8 to 10, carbon atoms. Typical examples are butanol, capronalcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, as are obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxosynthesis.
• the alkyl or alkenyl radical R 1 can also be derived from primary alcohols having 12 to 22, preferably 12 to 14, carbon atoms.
• Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol and the technical mixtures described above, which can be obtained as well as their technical mixtures.
• Alkyl oligoglucosides based on hardened Ci 2 / ⁇ 4 coco alcohol with a DP of 1 to 1.8 are preferred.
• halocarboxylic acids or their salts are used, which preferably follow the formula (II)
• n numbers from 1 to 5 and X represents hydrogen or an alkali metal, preferably sodium or potassium.
• X represents hydrogen or an alkali metal, preferably sodium or potassium.
• chloroacetic acid or its sodium salt are used.
• the carboxylation of the alk (en) yl oligoglycosides can be carried out in a manner known per se, ie by direct reaction of the reactants in aqueous solution at elevated temperature.
• the alkyl and / or alkenyl oligoglycosides and the halocarboxylic acids or their salts are typically used in a molar ratio of 1: 0.9 to 1: 5, preferably 1: 1.05 to 1: 3 and in particular 1: 1.2 to 1: 2 a.
• the excess of halocarboxylic acids depends primarily on the number of carboxyl functions that are to be introduced into the molecule in this way.
• aqueous pastes from Alkyl and / or alkenyl oligoglycoside carboxylic acid salts which have a solids content of 30 to 60 and in particular 40 to 50% by weight and contents of organic chlorine compounds of up to 2,500 ppm.
• the pastes are subjected to an alkaline aftertreatment, ie adjusted to a pH of 10 to 14 and preferably 11 to 13 by adding aqueous alkali compounds, preferably sodium or potassium hydroxide solution.
• aqueous alkali compounds preferably sodium or potassium hydroxide solution.
• Aftertreatment has proven to be particularly advantageous - optionally under (autogenous) pressure - at a temperature of 60 to 110 ° C., and in particular 70 to 90 ° C. It is also recommended that the aftertreatment be carried out in the absence of atmospheric oxygen, that is, under an inert gas blanket, in order to prevent discoloration of the products.
• the reaction time results from the interaction of pH and temperature and is typically 2 to 5 hours. In fact, it is advisable to follow the course of the aftertreatment by sampling and to stop the reaction as soon as the content of monochloro compounds has dropped below 5 ppm and that of dichloro compounds has dropped below 30 ppm.
• aqueous paste of a C ⁇ 2/1 - Kokosalkyloligoglucosidcarboxylats (Plantapon® LGC, Cognis Germany GmbH & Co. KG) provided with a residual content of 314 ppm and 58 ppm dichloroacetate monochloroacetate with 13 , 7 g of aqueous 50% by weight sodium hydroxide solution adjusted to a pH of 13.5 (measured in a 10% by weight dilution).
• the mixture was then stirred under a nitrogen blanket at a temperature of 90 to 95 ° C. for a period of 3 h.
• the purified product was obtained as a pale yellow liquid and still had a monochloroacetate content of less than 1 ppm and a dichloroacetate content of less than 5 ppm after the treatment.

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• Organic Chemistry (AREA)
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• Genetics & Genomics (AREA)
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• Crystallography & Structural Chemistry (AREA)
• Saccharide Compounds (AREA)
• Detergent Compositions (AREA)

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• 2002
  • 2002-12-19 DE DE10259403A patent/DE10259403A1/de not_active Withdrawn
• 2003
  • 2003-12-09 ES ES03785775T patent/ES2258739T3/es not_active Expired - Lifetime
  • 2003-12-09 DE DE50302682T patent/DE50302682D1/de not_active Expired - Lifetime
  • 2003-12-09 EP EP03785775A patent/EP1572706B1/de not_active Expired - Lifetime
  • 2003-12-09 JP JP2004561246A patent/JP2006516125A/ja active Pending
  • 2003-12-09 US US10/539,668 patent/US7384904B2/en not_active Expired - Lifetime
  • 2003-12-09 WO PCT/EP2003/013920 patent/WO2004056842A1/de not_active Ceased

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