content_image/937250.jpg content_image/937249.jpg content_image/937260.jpg content_image/937252.jpg content_image/937251.jpg
# c12) United States Patent 

# Notte et al. 

# (54) METHOD FOR THE MANUFACTURE OF AMINOALKYLENE PHOSPHONIC ACID 

(75) Inventors: Patrick Notte, Wavre (BE); Albert Devaux, Mont-Saint-Guibert (BE) 

(73) Assignee: Straitmark Holding AG, Zug (CH) 

( *) Notice: Subject to any disclaimer, the term ofthis patent is extended or adjusted under 35 U.S.C. 154(b) by 723 days. 

(21) Appl. No.: 12/989,306 

(22) PCT Filed: Apr. 25, 2009 

(86) PCT No.: PCT /EP2009/055000 § 371 (c)(l), (2), ( 4) Date: Dec. 8, 2010 

(87) PCT Pub. No.: WO2009/130322 

PCT Pub. Date: Oct. 29, 2009 

## (65) Prior Publication Data 

US 2011/0118502 Al May 19, 2011 

## (30) Foreign Application Priority Data 

<img src='content_image/937250.jpg'>

(51) Int. Cl. C07F 9/44 C07F 9/38 (2006.01) (2006.01) 

(52) U.S. Cl. CPC .................................... C07F 9/3817 (2013.01) USPC . ... ... ... .. ... ... ... ... ... .. ... ... ... ... ... .. ... ... ... ... .. 562/11 

( 58) Field of Classification Search USPC ............................................................ 562/11 See application file for complete search history. 

## (56) References Cited 

<img src='content_image/937249.jpg'>

## U.S. PATENT DOCUMENTS 

<img src='content_image/937260.jpg'>

# (IO) Patent No.: US 8,884,053 B2 

# Nov. 11, 2014 (45) Date of Patent: 

<img src='content_image/937252.jpg'>

## FOREIGN PATENT DOCUMENTS 

<img src='content_image/937251.jpg'>

"The Direct Synthesis of a-Aminomethylphosphonic Acids, Man› nich-Type Reactions with Orthophosphorus Acid," Moedritzer and Irani, J. Org. Chem., vol. 31 pp. 1603-1607 (1966). 

Primary Examiner - Sikarl Witherspoon 

(74) Attorney, Agent, or Firm - Husch Blackwell LLP 

## (57) ABSTRACT 

A method for the manufacture of amino alkylene phosphonic acids is disclosed. Pure P $_{4}$0 $_{6 }$is hydrolyzed in the presence of a homogeneous Broensted acid catalyst whereby the pH of the reaction medium is maintained below 5 and the free water content of said reaction medium is, after the P $_{4}$0 $_{6 }$hydrolysis has been completed, from O to 40%. The required amine component can be added before, during, or in one preferred execution, after the P $_{4}$0 6 hydrolysis has been completed. Formaldehyde is then added and the reaction mixture con› taining the P $_{4}$0 6 hydrolysate, the amine and the formalde› hyde is reacted in presence of a Broensted acid catalyst selected from homogeneous and heterogeneous species. The amino alkylene phosphonic acid reaction product can then be recovered in a manner known per se. 

US008884053B2 

## OTHER PUBLICATIONS 

## 16 Claims, No Drawings 

