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# c12) United States Patent 

# Barnicki et al. 

# (54) HYDROCARBOXYLATION OF METHYLENE DIPROPIONATE IN THE PRESENCE OF A PROPIONIC ACID AND A HOMOGENEOUS CATALYST 

(75) Inventors: Scott Donald Barnicki, Kingsport, TN (US); Robert Thomas Hembre, Johnson City, TN (US); Stephen Neal Falling, Kingsport, TN (US) 

(73) Assignee: Eastman Chemical Company, Kingsport, TN (US) 

( *) Notice: Subject to any disclaimer, the term ofthis patent is extended or adjusted under 35 U.S.C. 154(b) by 176 days. 

(21) Appl. No.: 13/431,402 

(22) Filed: Mar. 27, 2012 

## (65) Prior Publication Data 

US 2013/0261329 Al Oct. 3, 2013 

(51) Int. Cl. C07C 51112 C07C 59/06 (2006.01) (2006.01) 

(52) U.S. Cl. CPC ...................................... C07C 51112 (2013.01) USPC ........................................... 562/518; 562/579 

( 58) Field of Classification Search CPC ................................ C07C 51/12; C07C 59/06 See application file for complete search history. 

## (56) References Cited 

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## U.S. PATENT DOCUMENTS 

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# (IO) Patent No.: US 8,927,766 B2 

# (45) Date of Patent: Jan.6,2015 

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## FOREIGN PATENT DOCUMENTS 

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Asci et al, Journal of Chemical Engineering Data, 2009, 54, pp. 2791-2794.* 

Primary Examiner - Paul A Zucker 

(74) Attorney, Agent, or Firm - Jennifer R. Knight 

## (57) ABSTRACT 

Disclosed is a process for the production and purification of glycolic acid or glycolic acid derivatives by the carbonylation of methylene dipropionate in the presence of a homogeneous acid catalyst and propionic acid. This invention discloses hydrocarboxylations and corresponding homogeneous acid catalyst and glycolic acid separations. The homogeneous acid catalyst is readily separated from the hydrocarboxylation reaction effluent and recycled and the propionic acid is readily removed from the glycolic acid and the propionic acid is recycled. 

US008927766B2 

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## OTHER PUBLICATIONS 

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## 24 Claims, No Drawings 

