Classifications

• • 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
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/39—Organic or inorganic per-compounds
  • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
  • C11D3/3905—Bleach activators or bleach catalysts
  • C11D3/3907—Organic compounds
  • C11D3/3917—Nitrogen-containing compounds
  • C11D3/3927—Quarternary ammonium compounds
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C253/00—Preparation of carboxylic acid nitriles
  • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups

Definitions

• the present invention relates to the synthesis of bifunctional
• Ammonium nitriles by one-step reaction of dialkylaminoacetonitriles with dihaloalkylene or dihaloarylene.
• EP-A-458 386 are obtained in EP-A-458 386 as part of a two-step reaction.
• first step the synthesis of a tertiary aminonitrile by reaction of the corresponding aldehyde or ketone with potassium cyanide and a secondary amine and in a second step, the quaternization of the aminonitrile with dimethyl sulfate.
• EP-A-464 880 the quaternization of the aminonitrile is carried out with para-methyltoluenesulfonate or para-dodecylalkylbenzenesulfonate.
• the corresponding tertiary amine is reacted with chloroacetonitrile to the respective ammonium nitrile.
• a problem for the industrial applicability of the process is the high cost of the haloacetonitriles, which make the production of these used as bleach activators in detergents and cleaners class more expensive.
• the present invention thus provides a process for the preparation of bifunctional ammonium nitriles of the formula (1)
• R 1 , R 2 , R 3 and R 4 are each individually hydrogen, hydroxyl, d- to C 2 4-alkyl, C 2 - to
• R 5 and R 6 are each independently a straight or branched Cr to C 2 4 alkyl, alkenyl or alkyl ether group, and X is an anion, the variable n is an integer 1-16 alkyl; wherein a dialkylaminoacetonitrile of the general formula (2)
• the process according to the invention is carried out by first dissolving or suspending the dialkylaminoacetonitrile of the formula (2) in a suitable polar aprotic solvent.
• suitable solvents are, for example: ethyl acetate, n-propyl acetate, i-propyl acetate, n-butyl acetate, i-butyl acetate and mixtures thereof, dimethyl sulfoxide, N-methylpyrrolidone, 1,3-dimethylimidazolidine. on.
• a dihaloalkyl compound or a haloaryl compound of the general formula (3) in the form of substance or as a solution is added dropwise to this solution or suspension.
• the two halogen atoms X may be the same or different.
• Dialkylaminoacetonitrile is 1, 8 to 2.5, preferably 2.0 to 2.3 molar equivalents based on the dihaloalkyl or haloaryl. Suitable dialkylaminoacetonitrile dimethylaminoacetonitrile, diethylaminoacetonitrile, methyl ethylaminoacetonitrile, di-n-propylaminoacetonitrile, di-n-butylaminoacetonitrile, di-n-hexylaminoacetonitrile, dimethylaminoacetonitrile and are preferred
• the reaction temperature is generally from 20 to 120 0 C, preferably 30 to 100 0 C, particularly preferably 40 to 8O 0 C.
• the reaction takes place over a period of 1 to 10 hours, preferably 2 to 9 hours, more preferably 4 to 8 hours ,
• the resulting product can be removed by filtration, suction filtration,
• Reaction mixture was stirred at 60 ° C for 5 hours. The reaction mixture was cooled to room temperature and the precipitated solid was filtered off.
• Example 5 Bleaching performance of bifunctional ammonium nitriles
• Bleaching compositions were prepared and tested with the inventive cationic nitrile compounds of Inventive Examples 1 and 2 and Comparative Substances 3 and 4.
• the compounds 1 to 4 have the following structure:

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

Priority Applications (3)

Applications Claiming Priority (2)

Publications (1)

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Family Applications (1)

Country Status (5)

Citations (3)

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• 2005
  • 2005-03-01 DE DE102005009137A patent/DE102005009137A1/de not_active Withdrawn
• 2006
  • 2006-02-24 WO PCT/EP2006/001735 patent/WO2006092247A1/de not_active Ceased
  • 2006-02-24 US US11/885,610 patent/US20090023942A1/en not_active Abandoned
  • 2006-02-24 EP EP06723108A patent/EP1856034A1/de not_active Withdrawn
  • 2006-02-24 JP JP2007557395A patent/JP2008531622A/ja not_active Withdrawn

Patent Citations (3)

Non-Patent Citations (2)

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