Organic compounds -- part of the class 532-570 series – Organic compounds – Phosphorus acids or salts thereof
Patent
1999-08-12
2000-10-10
Richter, Johann
Organic compounds -- part of the class 532-570 series
Organic compounds
Phosphorus acids or salts thereof
562 18, C07F 938
Patent
active
061303518
ABSTRACT:
A process for the production of N-(phosphonomethyl)iminodiacetic acid. N-(acetyl)iminodiacetic acid is formed in a amidocarboxymethylation reactor system, into which a source of each of the following is continuously fed: (1) acetamide or an acetamide derivative, (2) formaldehyde or a formaldehyde generator or derivative, (3) a carbonylation catalyst, (4) carbon monoxide, and optionally (5) hydrogen. In turn, an amidocarboxymethylation reaction product stream, which contains N-(acetyl)iminodiacetic acid and the carbonylation catalyst, is withdrawn from the amidocarboxymethylation reactor system. The carbonylation catalyst is separated from the amidocarboxymethylation reaction product stream to recover the carbonylation catalyst and form a catalyst depleted product stream which contains N-(acetyl)iminodiacetic acid. The separated carbonylation catalyst is returned to the amidocarboxymethylation reactor system, and the N-(acetyl)iminodiacetic acid in the catalyst depleted product stream is either: (1) reacted with a source of phosphorous and a source of formaldehyde in the presence of an acid to form a phosphonomethylation reaction product stream containing N-(phosphonomethyl)iminodiacetic acid and acetic acid; or (2) deacylated and cyclized to form a 2,5-diketopiperazine, and then reacted with a source of phosphorous and a source of formaldehyde in the presence of an acid to form a phosphonomethylation reaction product stream containing N-(phosphonomethyl)iminodiacetic acid and acetic acid. Either way, the N-(phosphonomethyl)iminodiacetic acid is precipitated from the phosphonomethylation reaction product stream in the presence of acetic acid, and the precipitate is recovered to form a filtrate stream.
REFERENCES:
patent: 2757200 (1956-07-01), Jones et al.
patent: 2757204 (1956-07-01), Ratcliff
patent: 2757205 (1956-07-01), Metzweiller et al.
patent: 2757206 (1956-07-01), Jones et al.
patent: 3246024 (1966-04-01), Gwynn et al.
patent: 3260745 (1966-07-01), Andress, Jr. et al.
patent: 3288846 (1966-11-01), Irani et al.
patent: 3766266 (1973-10-01), Wakamatsu et al.
patent: 3847997 (1974-11-01), Allen
patent: 3904668 (1975-09-01), Gaudette et al.
patent: 3969398 (1976-07-01), Hershman
patent: 3998887 (1976-12-01), Allen
patent: 4225458 (1980-09-01), Huang et al.
patent: 4264515 (1981-04-01), Stern et al.
patent: 4312662 (1982-01-01), Gaertner
patent: 4400330 (1983-08-01), Wong et al.
patent: 4533500 (1985-08-01), Chauvin et al.
patent: 4624937 (1986-11-01), Chou
patent: 4657705 (1987-04-01), Huang et al.
patent: 4696772 (1987-09-01), Chou
patent: 4804499 (1989-02-01), Miller et al.
patent: 4918222 (1990-04-01), Lin et al.
patent: 4954466 (1990-09-01), Weisenfeld
patent: 5068404 (1991-11-01), Miller et al.
patent: 5237104 (1993-08-01), Summerlin
patent: 5527953 (1996-06-01), Jones et al.
CA:127:65516 abs of JP09157233, Jun. 1997.
A. Dorfman et al. "Kinetics and Mechanism of the Oxidative Alkoxylation of Tetraphosphorus in the Presence of Copper (II) Sulfates and Carboxylates" Kinetics and Catalysis, vol. 36, No. 1, pp. 93-100 (1995).
J. Franz et al. "Methods of Preparing Glyphosate" in Glyphosate: A Unique Global Herbicide, Chapter 8, pp. 233-262 (American Chemical Society, Washington, D.C., 1997).
J. Parnaud et al. "Some Aspects of the Catalytic Synthesis of N-acyl-.alpha.-Aminoacids by Carbonylation of Aldehydes in the Presence of Amides" Journal of Molecular Catalysis, vol. 6, pp. 341-350 (1979).
H. Wakamatsu et al. "Synthesis of N-Acyl Amino-Acids by a Carbonylation Reaction" Chemical Communications, p. 1540 (1971).
R. Weisenfeld "Metal-Catalyzed Carbonylation of Acetamide: Homogeneous-Phase Recovery of Cobalt from a Water-Soluble Amino Acid" Ind. Eng. Chem. Res., vol. 31, No. 2, pp. 636-638 (1992).
F. Bartha et al. "Plant Growth Regulator Precursors Comprising N-(phosphonomethyl)glycine or its Derivative And Carbonates" Chemical Abstract, vol. 113, No. 36393 (1989).
C. Chai et al. "Reactivities of Piperazine-2,5-diones In Radical Bromination Reactions" Chemical Abstract, vol. 126, No. 157470 (1996).
G. Evans et al. "Synthetic And Catalytic Studies of Polymer-Bound Metal Carbonyls" Journal of Organometalic Chemistry, 67, pp. 295-314 (1974).
J. Knap et al. "Dicobalt Octacarbonyl: Kinetics Of The Synthesis At High Pressure" High Pressure Technology, Chemical Engineering Progress Progress Symposium Series, No. 76, vol. 63, pp. 47-54 (19--).
A. J. Moffat "The Use Of Solid Polymeric Ligands In A New Oxo Catalyst recovery And Recycle System" Journal of Catalysis, vol. 19, pp. 322-329 (1970).
D. Riley et al. "Homogeneous Catalysts For Selective Molecular Oxygen Driven Oxidative Decarboxylations" J. Am. Chem. Soc., vol. 113, pp. 3371-3378 (1991).
D. Riley et al. "Vanadium (IV, V) Salts As Homogeneous Catalysts For The Oxygen Oxidation of N-(Phosphonomethyl)Iminodiacetic Acid To N-(Phosphonomethyl)Glycine" Inorg. Chem., vol 30, pp. 4191-4197 (1991).
J. Knifton "Amidocarbonylation" Applied Homogeneous Catalysis with Organometallic Compounds, vol. 1, pp. 159-168 (ed. by Cornils & Herrmann, Weinheim Germany, 1996).
Franczyk, II Thaddeus S.
Johnson Todd J.
Jorgenson Amy L.
Rogers Michael D.
Stern Michael K.
Monsanto Company
Richter Johann
Vollano Jean F
LandOfFree
Continuous process for the preparation of N-(phosphonomethyl) im does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Continuous process for the preparation of N-(phosphonomethyl) im, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Continuous process for the preparation of N-(phosphonomethyl) im will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2258076