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OJC Vol 31(Special ORIENTAL JOURNAL OF CHEMISTRY ISSN: 0970-020 X CODEN: OJCHEG An International Open Free Access, Peer Reviewed Research Journal 2015, Vol. 31, (Spl Edn): Month : Oct. www.orientjchem.org Pg. 01-12 Aminomethylenephosphonic Acids Syntheses and Applications (A Review) DIDIER VILLEMIN1 and MOHAMED AMINE DIDI2* 1Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507, INC3M, FR 3038, Labex EMC3, ENSICAEN, 14050 Caen, France. 2Laboratory of Separation and Purification Technology, Tlemcen University, Faculty of Sciences, Department of Chemistry,Box 119, Algeria. *Corresponding author E-mail: [email protected] (Received: March 25, 2015; Accepted: May 10, 2015) http://dx.doi.org/10.13005/ojc/31.Special-Issue1.01 ABSTRACT A review. In this paper, were reviewed the aminomethylenephosphonic acids which have several synthesis routes and many applications as separation of metals and rare earth by solvant extraction, N-C-P in medicinal chemistry, pesticides/herbicides and water-decontamination systems, organometallic complexes: MOF, gas absorption, proton conductivity and Magnetic shielding tensors / aminotris(methylenephosphonates). Key words: Aminomethylphosphonic; solvent extraction; chelate; rare earth metals; pesticides; herbicides. INTRODUCTION O O H H N C N P Aminophosphonic acid can be an OH OH attractive molecule because it can be used in a OH large range of field. The aim of this report is amino acid aminophosphonic acid to summarize synthesis methods of Fig. 1: Similarity between amino acids aminomethylphosphonic acids and their and aminophosphonic acids applications. Most important characteristic of these This similarity gives to aminomethyl- compounds is their N-C-P molecular fragment that phosphonic acid biological applications in broadly defines them as analogues of amino acids, healthcare and agriculture. Moreover, it is a weak in which the carboxylic group is replaced by a organic acid with a pKa value of 0.5 and its toxicity phosphonic acid (Figure 1). is lower than glyphosate’s one, its main source1. 2 VILLEMIN et al., Orient. J. Chem., Vol. 31(Spl Edn.), 01-12 (2015) O O This report will be divided in two parts. First, H P N several synthetic routes to aminomethylphosphonic HO OH acids will be detailed. On the other hand, HO applications of aminomethyphosphonic acids in Fig. 2: Structure of glyphosate various fields will be presented. First OH group in phosphonate acids is Preparation of N-substituted amino- very acidic, with a pKa value of 0.5-1.5. However, methylphosphonic acid compounds second OH group has a significantly lower acidity With the aim to get as efficiently as possible with a pKa value of 5.0-6.5 (Figure 3a). α-aminophosphonic acids, two main synthetic routes were developed. The most common one is in two distinct steps, synthesizing first the ester (pK a 9.5-10.5) NH2 derivative, then hydrolyzed. Another method OH (pK a 5.0-6.0) R P consists in a direct synthesis of the acid. OH (pKa 0.5-1.5) O Preparation aminomethylphosphonic esters Fig. 3a: Aminophosphonate acids pK a Via Mannich reaction In this part will be detailed different synthetic routes to distinct α-aminophosphonic Like amino acids, aminophosphonic acids esters, whose hydrolyses will be itemized in next have a zwitterionic form (Figure 3b) due to internal chapter. hydrogen bonding between phosphonate and ammonium groups, a characteristic which is strongly First synthesis of diethylaminomethyl- demonstrated by NMR and X-ray studies. phosphonic diethylester using Mannich reaction is in two steps. Hydroxymethylamine intermediate is + NH2 NH3 synthesized in excellent yield by causing to react OH OH together formaldehyde and diethylamine. Final R P R P - product is achieved though phosphite diethylester OH O 2 O O addition (Fig. 4) . H Fig. 3b: Zwitterionic form of H2CO + HN(C2H5)2 HO C N(C2H5)2 aminomethyl-phosphonic acid H H O O Aminomethylphosphonic acids and HO C N(C2H5)2 + H P(OC2H5)2 H2CP(OC2H5)2 derivatives have several applications. They can H N(C2H5)2 reduce and stop corrosion and by this way, protect electroplating or chemical plating. Pesticides and Fig. 4: Synthesis via formaldehyde, herbicides are another field where disubstituted amine and phosphite ester aminomethylphosphonic acids are efficient. They are used as water decontaminator in order to remove Mechanism of this reaction is the one of some hazardous micropollutant molecules. Mannich reaction with first nucleophile attack of diethylamine on formaldehyde, followed by a Its two hydroxyl functions linked to balance of the intermediate with its acid form. This phosphorus atom can easily be connected to a metal hydroxymethylamine is in balance with associated and chelate it. This property allows to do gas iminium finally attacked by diethylphosphite to form absorption, notably CO2, to generate MOF and to final aminomethylphosphonic ester (Figure 5). extract selectively metal from a solid or a liquid phase, especially for lead. Magnetic shielding Experimentally, 7.5 parts 40% aqueous generated by phosphorus atom archives to create formaldehyde is added to a cold mixture of 13.8 parts a perturbation in a metal-phosphoric acid crystal. diethyl phosphite and 7.32 parts diethylamine. The VILLEMIN et al., Orient. J. Chem., Vol. 31(Spl Edn.), 01-12 (2015) 3 O OH P P OEt OEt OEt EtO OEt H OEt HO P+ OEt O P OEt HO- - + H C H H C H O Et O OH H H N N C +EtN H C H H C H C Et Et Et Et H H H N N - HO- N+ Et Et Et Et Et Et Fig. 5: Mechanism of formation of aminomethylphosphonic ester via Mannich reaction resulting clear solution becomes hot. When it no To face this problem, an alternative longer evolves heat (10-15 minutes), it is distilled method for preparing aminomethyl-phosphonic in vacuo. There are obtained 20.3 parts (84.2%) of ester was discovered. Using a tetra-substituted diethylaminomethylphosphonic acid diethyl ester alkylidenediamine with a phosphite diester allows as a colorless oil boiling at 95°C at 3 mm pressure. to avoid formation of water (Figure 6)1. This reaction can be performed with other carbonyl compounds, other primary or secondary R2 R O R N O 4 R2 amines and other phosphite diesters. Water is 4 R3 C + H P(OR1)2 R C P(OR 1)2 +HN R N R2 always formed as a product in this reaction. In some N R3 R R3 R2 cases, the carbonyl compound reacts relatively 3 slowly and a side reaction may occur: some Fig. 6: Synthesis via alkylidenediamine phosphite diester may be hydrolysed by the and phosphite diester gradually formed water. O OH P OR P H 1 R1O OR1 OR1 R1O R4 R R1O R4 R2 2 HNR2R3 + R O P+ CN R O P CN R2 R2 H 1 1 + R HO R R3 O R R3 R4 N R R4 N R 4 C 3 C 3 C+ R N R2 R N R2 R N R2 - HNR2R3 Et R3 R3 Fig. 7: Mannich mechanism without formation of water Mannich mechanism is exactly the same Via enantioselective synthesis with the exception of formation of water which is Aminomethylphosphonic ester are also replaced by a secondary amine (Figure 7). accessible via reaction between imine and phosphite diethylester (Figure 8). In this case, the In this case, 13.8 parts of diethyl phosphite use of an enantiopure catalyst (Figure 9) allows to are added to 10.32 parts of methylol-diethylamine. getting one major compound, with distinct The mixture is kept below 40°C by cooling till heat enantiomeric excess, depending on the catalyst and [3] is no longer evolved, then distilled. There are R1 and R2 groups (Table 1). obtained 23.6 parts (98%) of diethylaminomethyl- phosphonic acid diethyl ester boiling at 95°C at 3 mm pressure. 4 VILLEMIN et al., Orient. J. Chem., Vol. 31(Spl Edn.), 01-12 (2015) 10 mol% Chiral OEt 2), the catalyst A showed too a similar trend with O O OEt R Bronsted acid P cinnamaldehyde in enhancing the enantioselectivity R N 2 + H POEt 1 R (entry 1 vs. entry 3). OEt Xylene 2 R1 * N 24 hrs, r.t. H Via Kabachnik-Fields reaction Fig. 8: Synthesis using imine Mechanism of this reaction called and phosphite diethylester Kabachnik-Fields was discovered in 1952 by Table 1: Effect of imine structure eponymous researchers and depends on the on enantioselectivitya nature of the substrates. It played a relevant role in drug discovery research for generating peptidomimetic compounds4. Entry Catalyst R1 R2 Yield e.e. (%) (%)b The amine and phosphonate form a complex, in which either one of the partners may 1 A S 20 0 react with the carbonyl compound. Usually, the basicity of the amine determines the reaction F N pathway. In the Kabachnik-Fields reaction mixture, 2 B S 56 10. two nucleophiles (dialkyl phosphite and the amine) 2 compete for the electrophilic carbonyl compound. F N 3 A 51 31. Experimental results revealed that the first 9 stage of the Kabachnik–Fields reaction, namely, the CH3 formation of a dialkyl phosphite–amine complex is 4 B 45 89. of critical importance for further reaction pathway. 5 Depending on the acidity–basicity relationship CH3 between the dialkyl phosphite and the amine, the readily polarizable complex can have a structure a Reaction conditions : aldimine (1 mmol), catalyst A or B like. (0.1 mmol), xylene (15 mL), diethyl phosphite (2 mmol), room temp. for 24 h; R3 b Determined by HPLC. O N + R3 NH2 + H2O R1 R2 R1 R2 CF3 R R1 R3 F N 3 O R2 N R1 R2 R O CF P 4 P H 3 R O H R4O 4 O O R4O H O O O O OR4 P P N P O O R3 OR4 H H R3 N R1 R2 R R CF3 R4O OH 1 3 P R1 R2 R2 N OR4 H F R4O P R4O O CF3 AB Fig.
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