Glycine-N,N-diacetic acid derivative preparation in high yield

    公开(公告)号:DE19736476A1

    公开(公告)日:1999-02-25

    申请号:DE19736476

    申请日:1997-08-21

    Applicant: BASF AG

    Abstract: Preparation of long-chain substituted glycine-N,N-diacetic acid derivatives (IX) and their intermediates, e.g. from aldehydes and hydrogen cyanide (or alkali metal cyanide) and other reagents such as iminodiacetic acid or ammonia and/or by hydrolysis of corresponding nitriles, is carried out under elevated pressure and/or in presence of additives such as emulsifiers. Several classes of intermediate compounds are new. Preparation of long-chain substituted glycinonitrile-N,N-diacetonitrile compounds of formula (IIb) by reaction of imino-diacetonitrile with aldehydes of formula RCHO and hydrogen cyanide (or alkali metal cyanide) is carried out: (a) in the absence of an organic solvent and in presence of a Lewis or Bronsted acid; (b) in the presence or absence of an organic solvent and in presence of an emulsifier; or (c) in the presence or absence of an organic solvent and under a pressure of 1-40 bar. R = 6-30C alkyl or 6-30C alkenyl, both optionally substituted by 1-5 of OH, CHO, 1-4C alkoxy, phenoxy and (1-4C) alkoxycarbonyl and optionally interrupted by 1-5 non-adjacent O; or -(CH2)kO(A1)n-Y; A1,A2 = 2-4C 1,2-alkylene; Y = H, 1-12C alkyl, phenyl or (1-4C) alkoxycarbonyl; k =1-3; m,n = 0-50, provided that m + n = at least 4. Independent claims are included for the following processes and novel compounds. (1) Preparation of long-chain substituted glycinonitrile compounds of formula R-CH(NH2)(CN) (IIa) by reaction of RCHO with M'CN (M' = H or alkali metal) and ammonia in presence of organic base is carried out under a pressure of 1-40 bars. (2) Preparation of (IIb) by reaction of (IIa) (which may be prepared as above) with formaldehyde and M'CN is carried out in the presence or absence of a solvent under a pressure of 1-40 bars. (3) Preparation of long chain-substituted glycine-N,N-diacetic acid (or its salts) of formula MOOC-CH(R)-N(CH2COOM)2 (IX) by reaction of (IIb) (which may be prepared as above) with alkali metal hydroxide, and optionally solutions providing ions M, is carried out under a pressure of 1-40 bars. M = H, alkali metal, alkaline earth metal or optionally substituted ammonium. (4) Preparation of long-chain substituted glycines (or their salts) of formula R-CH(NH2)(COOM) (IV) by reaction of (IIa) (which may be prepared as above) with alkali metal hydroxide, and optionally solutions providing ions M and/or 3-9C aliphatic ketones, is carried out under a pressure of 1-40 bars. (5) Preparation of (IX) by reaction of (IV) (which may be prepared as above) with HCHO and M'CN followed by reaction with alkali metal hydroxide, and optionally solutions providing ions M, is carried out under a pressure of 1-40 bars. (6) Further preparations of (IX) involve: (6i) reacting iminodiacetic acid derivatives of formula X-CH2-NH-CH2-Y (XI) with RCHO and M'CN or with a cyanohydrin R-CH(OH)CN, in the presence or absence of an organic solvent and under a pressure of 1-40 bar; (6ii) reaction of glycine with RCHO and M'CN for mono-substitution, followed by reaction with HCHO and M'CN or with HOCH2CN, in the presence or absence of an organic solvent and under a pressure of 1-40 bar; or (6iii) reaction of glycine with HCHO and M'CN or with OHH2CN for mono-substitution, followed by reaction with RCHO and M'CN, in the presence or absence of an organic solvent and under a pressure of 1-40 bar. Any nitrile or amide functions present may be subsequently hydrolysed, suitably under a pressure of 1-40 bars. X,Y = COOM, (1-12C) alkoxycarbonyl, CONH2 or CN. Compounds of formulae (I), (IIa; R = R1), (III), (IV; R = R1), (V)-(VIII), (X) and (XII)-(XVI) are new, with the exception of (IV; R = 17-20C alkenyl), (V; R1 = 17-20C alkenyl), (I; R1 = n-9-decenyl), (VIII; R1 = 6-10C alkenyl), (IV; R1 = 2-(5-20C alkoxy)-ethyl) and (X; R1 = 2-(5-8C alkoxy)-ethyl). R1 = 6-20C alkenyl or CH2CH2OR3; R2 = 2-6C alkyl; R3 = 3-20C alkyl or 3-20C alkenyl.

    Phosphate free washing agents
    6.
    发明专利

    公开(公告)号:DE19624701A1

    公开(公告)日:1998-01-02

    申请号:DE19624701

    申请日:1996-06-20

    Applicant: BASF AG

    Abstract: Phosphate free washing agent comprising (a) 1-60 wt. % of at least one inorganic builder, (b) 0.1-25 wt. % of at least one anionic detergent of formula R -CH(OH)-CH(R )-N(R )-Y-COOM (I) , (c) optionally 0-40 wt. % of at least one further anionic detergent, (d) 0.5-30 wt. % of at least one nonionic detergent, and optionally washing and cleaning agents. R , R = H, aryl, alkyl or alkenyl (both optionally substituted with 1-3 residues selected from aryloxy or alkoxycarbonyl and/or interrupted by 1-5 non-adjacent O atoms), or R and R together with the groups to which they are bound may form the residue of a mono- or polyunsaturated fatty acid which forms, by way of an ester bond, part of a triglyceride, which (depending on the original number of double bonds in its fatty acid residue, having up to 9 groups of formula (I) (sic), R = H, alkyl, -CHR -CH(OH)-R (IIa) or -(CH2)n-COOM (IIb); n = 1-4; R , R = as for R and R , and the sum of the C atoms in R , R , R and R \- 4; Y = alkylene (optionally substituted by OH and/or COOM), or R +N+Y = a 5- or 6-membered, saturated or unsaturated heterocyclic ring; M = H, alkali(ne earth) metal, optionally substituted ammonium.

    8.
    发明专利
    未知

    公开(公告)号:DE4203169A1

    公开(公告)日:1993-08-12

    申请号:DE4203169

    申请日:1992-02-05

    Applicant: BASF AG

    Abstract: Granular bleaching activator composition with variously shaped grains containing as the core: A) 30 to 98 wt %, in relation to the total quantity of granular bleaching activator composition, of one or more 4H-3,1-benzo-oxazin-4- one derivatives of general formula (I) in which R is C1 to C4-alkyl, C1 to C4-alkoxy, chloromethyl, methoxy methyl, dimethylamino phenyl, o-, m- or p-tolyl, p-chlorophenyl, m-nitrophenyl, m-methoxy phenyl or m-methyl sulphonyl phenyl and R' is hydrogen, methyl, chloro, nitro, acetoxy or hydroxy, or a mixture of compounds (I) and other usual bleaching activators; and as the casing: B) 2 to 70 wt %, in relation to the total quantity of the granular bleaching activator composition, of one or more additives from the classes of substances: (1) anionic tensides; (3) non-ionic tensides; (3) hybrid ionic tensides; (4) carboxyl-group-containing polymers; (5) polysaccharides; (6) polyalkylene glycols; (7) acid alkaline and alkaline earth metal salts of inorganic acids; (8) aliphatic C8 to C18-monocarboxylic acids, aliphatic di and tricarboxylic acids, aromatic mono and dicarboxylic acids, the aforementioned carboxylic acids possibly also containing hydroxyl and amino groups in the molecule, and aliphatic C3 to C7-monohydroxycarboxylic acids.

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