Chemistry:ATMP

From HandWiki

ATMP or aminotris(methylenephosphonic acid) is a phosphonic acid with chemical formula N(CH2PO3H2)3. It is a colorless solid. Its conjugate bases, such as [N(CH2PO3H)3]3-, have chelating properties.

ATMP can be synthesized from the Mannich-type reaction of ammonia, formaldehyde, and phosphorous acid, in a manner similar to the Kabachnik–Fields reaction.[1][2]

Properties

ATMP has good antiscale performance.[3][4] It is related structurally to nitrilotriacetic acid.[5]

Applications

  • (1-Aminoethylidene)bisphosphonic acid, CH
    3
    C(NH
    2
    )[PO(OH)
    2
    ]
    2
    , also a chelating agent
  • Etidronic acid, CH
    3
    C(OH)[PO(OH)
    2
    ]
    2
    , also a chelating agent
  • Glyphosate, HO
    2
    CCH
    2
    NHCH
    2
    [PO(OH)
    2
    ]
    2
    , a herbicide

References

  1. Petrov, K. A.; Maklyaev, F. L.; Bliznyuk, N. K (1959). "Synthesis of aminodiphosphonates and aminotriphosphonates". Zhurnal Obshchei Khimii 29: 591–4. 
  2. Moedritzer, Kurt; Irani, Riyad R. (1966). "The Direct Synthesis of α-Aminomethylphosphonic Acids. Mannich-Type Reactions with Orthophosphorous Acid". The Journal of Organic Chemistry 31 (5): 1603. doi:10.1021/jo01343a067. 
  3. Labjar, Najoua; Lebrini, Mounim; Bentiss, Fouad; Chihib, Nour-Eddine; Hajjaji, Souad El; Jama, Charafeddine (2010). "Corrosion inhibition of carbon steel and antibacterial properties of aminotris-(methylenephosphonic) acid". Materials Chemistry and Physics 119 (1-2): 330–336. doi:10.1016/j.matchemphys.2009.09.006. 
  4. Tang, Yongming; Yang, Wenzhong; Yin, Xiaoshuang; Liu, Ying; Yin, Pengwei; Wang, Jintang (2008). "Investigation of CaCO3 scale inhibition by PAA, ATMP and PAPEMP". Desalination 228 (1-3): 55–60. doi:10.1016/j.desal.2007.08.006. 
  5. Cabeza, Aurelio; Ouyang, Xiang; Sharma, C. V. Krishnamohan; Aranda, Miguel A. G.; Bruque, Sebastian; Clearfield, Abraham (2002-05-01). "Complexes Formed between Nitrilotris(methylenephosphonic acid) and M 2+ Transition Metals: Isostructural Organic−Inorganic Hybrids". Inorganic Chemistry 41 (9): 2325–2333. doi:10.1021/ic0110373. ISSN 0020-1669.