N-bis- or N-tris-[(1,2-dicarboxy-ethoxy)-ethyl]-amine derivative

Details N-bis- or N-tris-[(1,2-dicarboxy-ethoxy)-ethyl]-amine derivative N-bis- or N-tris-[(1,2-dicarboxy-ethoxy)-ethyl]-amine derivative

1998-11-24

2000-07-25

Richter, Johann

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acids and salts thereof

C07C22922

Patent

active

060938498

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/FI97/00332 filed May 30, 1997.
The invention relates to novel N-bis- or N-tris-[(1,2-dicarboxy-ethoxy-(ethyl]-amine derivatives and to the preparation and use of the same.
The formula of the novel compounds according to the invention is ##STR2## and R.sub.2 is hydrogen, an alkali metal or an earth alkali metal.
It is often necessary to bind heavy metal ions and earth-alkali ions as water-soluble chelates, for example, in various washing processes. In photography chemicals, chelates of metal ions are used in the developing process. When oxygen or peroxide compounds are used in the total chlorine free (TCF) bleaching of pulp it is important to remove the heavy metals from the fiber before bleaching, since heavy metal salts catalyze the decomposition of peroxy compounds, thus forming radical compounds. In consequence of these reactions the strength properties of the fiber are deteriorated.
At present, the complexing agents most commonly used in the applications mentioned above are ethylenediaminetetraacetic acid (EDTA) and its salts and diethylenetriaminepentaacetic acid (DTPA) and its salts. These are excellent complexing agents, but their biodegradability is poor.
Patent applications FI-960758, FI-960757, FI-960756 and FI-960755 disclose the use of aspartic acid derivatives as chelating agents in bleaching of pulp. Such chelating agents include ethylenediaminedisuccinic acid (EDDS) and its earth-alkali salts, as well as N,N'-iminodisuccinic acid (ISA) and its earth-alkali salts. EDDS and ISA are effective chelating agents of heavy metals. In addition, they are biodegradable.
From JP patent applications 7 261 355 and 6 282 044 there are known EDDS-type aspartic acid derivatives in which the hydrocarbon chain is longer than in EDDS. One such substance is N,N'-(oxydi-2,1-ethanediyl)-bis-L-aspartic acid.
Chelating agents should contain as small an amount as possible of nitrogen in order for the nitrogen load in waste waters to be as low as possible. Chelating agents of the type of EDDS, wherein some of the nitrogen atoms have been replaced with oxygen atoms, are disclosed in JP patent applications 7 120 899 and 7 120 894. The applications disclose the use of various isomers of N-[2-(1,2-dicarboxyethoxy)-ethyl]-aspartic acid (EDODS) in photography chemicals. According to the publications, EDODS is biodegradable. A method of preparing EDODS by La.sup.3+ -catalyzed O-alkylation of maleic acid salts has been described in the literature (J. van Vestrenen et al., Recl. Trav. Chem. Pays-Bas, vol. 109, 1990, p. 474-478). However, in application tests performed by the applicant, EDODS did not prove to be a sufficiently effective chelating agent. One possible explanation for the poor chelating result is the length of the carbon chain between the dicarboxyethyl groups. If the said carbon chain is not sufficiently long, strains are produced in the molecule during complexing, and the metal complex will not be sufficiently stable.
The object was to develop an effective chelating agent which would be biodegradable and contain little nitrogen.
The formula of the new compounds according to the invention is ##STR3## and R.sub.2 is hydrogen, an alkali metal or an earth-alkali metal.
In the said molecule structure, a secondary or tertiary nitrogen atom is as the central atom. Additionally the molecular structures contain four or six carboxylic acid groups, which coordinate effectively with heavy metals. The carbon chains are sufficiently long in terms of the formation of advantageous bond angles.
Novel compounds according to the invention include N-bis-[(1,2-dicarboxy-ethoxy) -ethyl]-amine (BCEEA), N-tris-[(1,2-dicarboxy-ethoxy)-ethyl]-amine (TCEEA) and N-bis-[(1,2-dicarboxy-ethoxy)-ethyl]-aspartic acid (BCEEAA), as well as the alkali metal and earth-alkali metal salts of the said compounds, preferably Na.sup.+, K.sup.+, Ca.sup.2+ and Mg.sup.2+ salts. ##STR4##
The novel amine compounds according to the invention can be prepared by using as the starting material alkali metal or earth-alkali metal sa

REFERENCES:
patent: 4044034 (1977-08-01), Christiansen
Finnish Patent Application No. 960755, filed Feb. 19, 1996.
Finnish Patent Application No. 960756, filed Feb. 19, 1996.
Finnish Patent Application No. 960757, filed Feb. 19, 1996.
Finnish Patent Application No. 960758, filed Feb. 19, 1996.
Chemical Abstracts, vol. 84, No. 20, May 17, 1976 (May 17, 1976), (Columbus, Ohio, USA), p. 122, The Abstract No. 137608h,, JP, 7602708 A, (Okumura, Osamu et al), Jan. 10, 1976 (Jan. 10, 1976).
Chemical Abstracts, vol. 123, No. 16, Oct. 16, 1995 (Oct. 16, 1995), (Columbus, Ohio, USA), p. 1024, The Abstract No. 212991, JP, 71208949 A, (Okada, Hisashi et al) May 12, 1995 (May 12, 1995).
J. van Westrenen et al., The synthesis of polyhydroxycarboxylates, Recl. Trav. Chem. Pays-Bas, vol. 109, 1990, p.474-478.

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