content_image/934785.jpg content_image/934786.jpg content_image/934802.jpg content_image/934787.jpg content_image/934788.jpg
# c12) United States Patent 

# Barnicki et al. 

# (54) PROCESS FOR RECOVERING AND RECYCLING AN ACID CATALYST 

(75) Inventors: Scott Donald Barnicki, Kingsport, TN (US); Stephen Neal Falling, Kingsport, TN (US); Jeffrey Scott Kanel, Kingsport, TN (US); Robert Sterling Kline, Kingsport, TN (US); Peter Borden Mackenzie, 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 522 days. 

(21) Appl. No.: 12/889,045 

(22) Filed: Sep.23,2010 

## (65) Prior Publication Data 

US 2012/OO78O1OAl Mar. 29, 2012 

(51) Int. Cl. 

<img src='content_image/934785.jpg'>

(52) U.S. Cl. USPC .............. 423/531; 562/45; 562/579; 562/580 

( 58) Field of Classification Search CPC ................................ CO1B17/9O; CO7C51/48 See application file for complete search history. 

## (56) References Cited 

<img src='content_image/934786.jpg'>

## U.S. PATENT DOCUMENTS 

<img src='content_image/934802.jpg'>

# (10) Patent No.: US 8,709,376 B2 

# (45) Date of Patent: Apr. 29, 2014 

<img src='content_image/934787.jpg'>

## FOREIGN PATENT DOCUMENTS 

<img src='content_image/934788.jpg'>

Notification of Transmittal of the International Search Report and the Written Opinion of the International Search Authority with Mail Date of Mar. 15, 2012 for International Application No. PCT/US2011/ 051490. 

Notification of Transmittal of the International Search Report and the Written Opinion of the International Search Authority with Mail Date of Nov. 28, 2011 for International Application No. PCT/US2011/ 047842. 

Celik et al., "Synthesis of precursors to ethylene glycol from form› aldehyde and methyl formate catalyzed by heteropoly acids", Journal of Molecular Catalysis A: Chemical 288, (2008), pp. 87-96. 

Celik et al., "Vapor-phase carbonylation of dimethoxymethane of H-Faujasite",Angewandte. Chemie Int. Ed. 2009, 48, pp. 4813-4815. Hou-Yong, Sun, et al. "Reactive extraction of glycolic acid in high content solution with tri-n-octylamine" Journal of Chemical Engi› neering of Chinese Universities vol. 21 pp. 26-30. 

Primary Examiner - Paul A Zucker 

(74) Attorney, Agent, or Firm - Jennifer Knight; Eric Middlemas 

## (57) ABSTRACT 

Disclosed is a process for the extractive recovery of an acid catalyst from an aqueous mixture of glycolic acid with an extraction solvent comprising a tertiary amine or an onium carboxylate compound, a modifier, and a diluent. The acid catalyst, which can comprise strong acids such as sulfuric acid, alkyl sulfonic acids, and fluoroalkyl sulfonic acids, can be recovered by back extraction with aqueous formaldehyde and recycled to a process for the preparation of glycolic acid by the acid-catalyzed carbonylation of formaldehyde. 

US0087093 76B2 

(Continued) 

(Continued) 

## OTHER PUBLICATIONS 

(Continued) 

## 18 Claims, No Drawings 

