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United States Patent (19) 11 Patent Number: 5,679,817 Sakai Et Al

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United States Patent (19) 11 Patent Number: 5,679,817 Sakai Et Al US005679817A United States Patent (19) 11 Patent Number: 5,679,817 Sakai et al. 45) Date of Patent: Oct. 21, 1997 54 ALKYLENEDIAMINE-N,N'-DSUCCINIC OTHER PUBLICATIONS ACD RON () COMPLEX SALTSA lines (1992). 75 Inventors: Haruo Sakai; Takashi Sato; Toshitake Stereospecific Ligands and Their Complexes, Nealetal, vol. Yamakawa, all of Otake, Japan 7, No. 11, Nov. 1968, pp. 2405-2412. Synthesis and Complex-Forming Properties of Complexons 73 Assignee: Nitto Chemical Industry Co., Ltd., Derived from DiCarboxylic Acids v. Synthesis of Complex Tokyo, Japan ons Derived from Succinic Acid,Gorelov et al., Zhurnal Obshchei Kimii 49 (3), pp. 659-663. European Office Action dated Dec. 5, 1996. 21 Appl.... No.: 505.4505.46 Chemicalp Abstracts, vol. 101,No. 20, Abstract No. 182607n, 22 Filed: Jul. 21, 1995 p. 735 (1984). 30 Foreign Application Priority Data Primary Examiner-Porfirio Nazario-Gonzalez Attorney; Agent, or Firm-Cushman Darby & Cushman IP Jul. 25, 1994 JP Japan .................................... 6-92248 Group of Pillsbury Madison & Sutro LLP 51) int. Cl.6 .............................................. CO7F 15/02 57 ABSTRACT 52 U.S. Cl. .................................................. 556/48 58) Field of Search .............................................. 556/148 (S.S)-ethylenediamine-N,N'-disuccinic acid iron (DI) ammonium salt represented by the formula: (56) References Cited U.S. PATENT DOCUMENTS Hch co-ch.co. 5,238,791 8/1993 Tappe. (H): Fe3+NH FOREIGN PATENT DOCUMENTS NHCH(COCHCO 0532003 3/1993 European Pat. Off. wherein C* is an asymmetric carbon atom. This compound 2. A: E. Pat. Off. has a very high biodegradability and it is not accumulated in 554600 3/1993 J iny the environment even when used as a photographic process 0574829 2/1993 E. ing agent or the like. Therefore, the compound is advanta 6208213 7/1994 Japan. geous for the protection of environment. 7-2745 1/1995 Japan. 1 397 479 6/1975 United Kingdom. 8 Claims, 5 Drawing Sheets U.S. Patent Oct. 21, 1997 Sheet 1 of 5 5,679,817 O OOO OO VO S 8 S. 5 O O O O 8 ) O L --O U O O O CN y O O O O O O O O o St O CO O V N U.S. Patent Oct. 21, 1997 Sheet 2 of 5 5,679,817 8 8 S. S O s 8 8 O O O 8 S. S. U.S. Patent Oct. 21, 1997 Sheet 3 of 5 5,679,817 3 8 S. S O 8 O 8 8 8 S. S. U.S. Patent Oct. 21, 1997 Sheet 4 of 5 5,679,817 8 V 8 : 8 O O 8 VO OCN O U.S. Patent Oct. 21, 1997 Sheet S of 5 5,679,817 3 8 S. S. O : O 8 3 8 S. S. 5,679,817 1. 2 alkylenediamine-N,N-disuccinic acidiron(III) complex salt ALKYLENEDIAMINE-N,N'-DSUCCINIC consisting of mesoisomer and racemic modification by ACID RON (III) COMPLEX SALTS AND microorganisms and consequently found that the PROCESS FOR PRODUCTION THEREOF alkylenediamine-N,N-disuccinic acidiron(III) complex salt BACKGROUND OF THE INVENTION 5 of (S,S) form, in particular, (S,S)-ethylenediamine-N,N'- disuccinic acid iron (III) ammonium salt is easily biode 1. Field of the Invention gradable compound which is much more rapidly degraded The present invention relates to novel alkylenediamine by microorganisms than the alkylene diamine-N,N'- NN'-disuccinic acid iron (III) complex salts usable as, for disuccinic acid iron (III) complex salt of meso form and that example, a photographic processing agent, and a process for O of (R,R) form. production thereof. In particular, the present invention The present invention was made on the basis of this relates to optically active iron chelate complexes, more finding. specifically, (S.S)-ethylenediamine-N,N'-disuccinic acid That is, one aspect of the present invention is directed to iron (III) complex salts, and a process for production an alkylenediamine-N,N-disuccinic acid iron (III) complex thereof. 15 salt represented by the formula (I): 2. Description of the Related Art Red prussiate (potassium hexacyanoferrate (III)) was HCH co, Chico, (I) widely used in the past as an oxidizing agent contained in a bleaching solution and a bleaching and fixing solution which (H). were used for printing of color photographs. But owing to NHCH(CO)CH2CO the pollution problem, i.e., the presence of cyanogen in a wherein M' is K, Na' or NH, and n is 2 or 3). waste solution after development, there are now used iron Another aspect of the present invention is directed to a chelate compounds such as ethylenediaminetetraacetic acid process for producing the above-mentioned (EDTA) iron (III) complex salts, diethylenetriaminepen alkylenediamine-N,N-disuccinic acidiron(III) complex salt 25 which comprises reacting an (C-C)alkylenediamine-N,N'- taacetic acid (DTPA) iron (III) complex salts, propanedi disuccinic acid with A) ammonia or an alkali metal hydrox aminetetraacetic acid (PDTA) iron (III) complex salts, etc. ide and B metallic iron or an iron compound in an aqueous However since these iron chelate compounds have a strong medium to give a corresponding alkylenediamine-N,N'- chelate bond strength between each acid and iron ions but disuccinic acid iron (II) ammonium or alkali metal salt, and are poor in biodegradability, they continue to be accumu oxidizing the salt if necessary. lated in the environment as industrial wastes. Therefore, 30 Further another preferable aspect of the present invention they have been disadvantageous for use from the viewpoint is directed to (S,S)-ethylenediamine-N,N-disuccinic acid of the protection of environment. iron (III) ammonium salt represented by the formula (II): On the other hand, there have been proposed several chelating agents which are used as a photographic agent and have biodegradability. They include, for example, Balanine 35 HCH co-ch.co. (II) N,N-diacetic acid (EP-A-0574829) and isoserine N.N- (H): diacetic acid (U.S. Pat. No. 5.238,791). These chelating NHCH(CO)CHCO agents, however, have been disadvantageous for use because wherein C is an asymmetric carbon atom. they have a low iron chelate stability constant of about 10, Still another aspect of the present invention is directed to so that when they are used as a photographic developing a process for producing (S,S)-ethylenediamine-N,N'- agent, iron remains in a film or a print. disuccinic acid iron (III) ammonium salt represented by the above formula (II) which comprises reacting (S,S)- SUMMARY OF THE INVENTION ethylenediamine-N,N-disuccinic acid with (A) iron or an An object of the present invention is to provide a novel 45 iron compound and B ammonia in an aqueous medium, iron chelate complex which is rapidly degraded by micro and oxidizing the reaction product if necessary. organisms and has a chelate-forming ability similar to that of BRIEF DESCRIPTION OF THE DRAWINGS the conventional chelate compounds (the EDTA iron (III) FIG. 1 is an IR spectrum obtained by a KBr tablet method complex salts, etc.), and a process for producing the same. of (S,S)-ethylenediamine-N,N-disuccinic acid iron (III) The present inventors produced a novel alkylenediamine ammonium salt synthesized in Example 1. N,N'-disuccinic acid iron (III) complex salt. This complex FIG. 2 is an IR spectrum obtained by a KBritablet method salt is a compound having a chelate-forming ability (iron of 13-propanediaminedisuccinic acid iron (III) complex chelate stability constant: about 20) similar to that of the ammonium salt synthesized in Example 5. EDTA iron (III) complex salts, the conventional chelate FIG.3 is an IR spectrum obtained by a KBritablet method compounds and a high biodegradability, as compared with 55 of 1,3-propanediaminedisuccinic acid iron (III) complex Balanine N.N-diacetic acid and isoserine N,N-diacetic acid. sodium salt synthesized in Example 6. Aforesaid alkylenediamine-N,N-disuccinic acid iron (III) FIG. 4 is an IR spectrum obtained by a KBritablet method complex salt, however, has two asymmetric carbon atoms, of ethylenediamine-N,N-disuccinic acid iron (III) complex so that a conventional process for producing the complex ammonium salt synthesized in Example 7. salt via alkylenediamine-N,N-disuccinic acid produced FIG. 5 is an IR spectrum obtained by a KBr tablet method from an alkylenediamine and maleic acid gives the complex of ethylenediamine-N,N-disuccinic acid iron (III) complex salt as a mixture of racemic modification and mesoisomer in sodium salt synthesized in Example 8. which 3 optical isomers, i.e., (S,S) form, (RR) form and PREFERRED EMBODIMENTS OF THE (SR) form are present in a ratio of 1:1:2. Of these optical INVENTION isomers, the (RR) form requires a conditioning period for 65 biodegradation. Accordingly, the present inventors investi The present invention is explained below in detail. The gated in further detail the biodegradation of the alkylenediamine-N,N'-disuccinic acidiron(III) complex salt 5,679.817 3 4 of the present invention has the structure represented by the ing agent such as molecular oxygen or a peroxide is reacted formula (I). In the formula (I), M+ denotes an ion of sodium, with the mixture to oxidize and dissolve the iron component, potassium or ammonium and indicates that a sodium, potas whereby the alkylenediamine-N,N-disuccinic acidiron(III) sium or ammonium salt is formed. As to the length of the complex salt is produced. When an iron (III) salt is used, the alkyl group connecting the nitrogen atoms, the alkyl group alkylenediamine-N,N-disuccinic acid iron (III) complex salt is composed of 2 or 3 methylene groups. Said complex salt is produced by reacting a (C-C)-alkylenediamine-N,N'- has a molecule of water of crystallization.
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