Purification of long chain diacids

Abstract

The present disclosure relates to methods for separating and purifying a long chain diacid from other long chain diacids, monocarboxylic acids, hydroxyl acids or alkanes by simulated or actual moving bed chromatography.

1 . A method for separating a C6- to C18-carbon diacid from at least one impurity in a solution, comprising:
 (a) introducing a feed stream comprising a solution comprising at least one 6- to 18-carbon diacid and at least one impurity, the at least one impurity comprising a component more polar than the diacid, a component less polar than the diacid, or both, into a first zone of moving bed chromatography apparatus (MBCA) having one or more zones;   (b) collecting a raffinate stream or an extract stream from the first zone of the MBCA, the raffinate stream comprising the diacid and one or more components more polar than the diacid, and the extract stream comprising the diacid and one or more components less polar than the diacid;   (c) introducing the raffinate stream or the extract stream into a second zone of the MBCA;   (d) collecting a second raffinate stream or a second extract stream from the second zone of the MBCA, the raffinate stream comprising the diacid and components more polar than the diacid, and the extract stream comprising the diacid and components less polar than the diacid;   (e) introducing the second raffinate stream or the second extract stream into the first zone or the second zone of the MBCA;   (f) optionally repeating steps (d) and (e) until a desired degree of separation is achieved; and   (g) collecting a final raffinate stream or a final extract stream from a zone of the MBCA, the final raffinate stream or the extract stream comprising the diacid, thereby separating a C6- to C18-carbon diacid from the at least one impurity in the solution.   
     
     
         2 . A method for separating a C6- to C18-carbon diacid from at least one impurity in a solution, comprising:
 (a) introducing a feed stream comprising a solution comprising at least one 6- to 18-carbon diacid and at least one impurity, the at least one impurity comprising a component more polar than the diacid, a component less polar than the diacid, or both, into a first zone of a moving bed chromatography apparatus (MBCA);   (b) collecting a raffinate stream or an extract stream from the MBCA, the raffinate stream comprising the diacid and components more polar than the diacid, and the extract stream comprising the diacid and components less polar than the diacid;   (c) introducing the raffinate stream or the extract stream into the first zone of the MBCA;   (d) optionally repeating steps (b) and (c) until a desired degree of separation is achieved; and   (e) collecting a final raffinate stream or a final extract stream from the first zone of the MBCA, the final raffinate stream or the extract stream comprising the diacid, thereby separating a C6- to C18-carbon diacid from the solution.   
     
     
         3 . The method of  claim 1 , wherein the at least one impurity is present in a final raffinate stream or a final extract stream at about 10,000 ppmw or less, about 5,000 ppmw or less, about 1,000 ppmw or less, about 500 ppmw or less, about 100 ppmw or less, about 50 ppmw or less, or about 10 ppmw or less. 
     
     
         4 . The method of  claim 1 , further comprising introducing the raffinate stream or the extract stream into first zone of the MBCA prior to first raffinate stream or the first extract stream introducing the raffinate stream or the extract stream into a second zone of the MBCA. 
     
     
         5 . The method of  claim 1 , wherein:
 the MBCA comprising two or more zones, each zone comprising one or more injection points for introducing the solution;   one or more injection points for introducing an eluent;   a raffinate stream from which liquid can be collected; and   an extract stream from which liquid can be collected.   
     
     
         6 . The method of  claim 1 , wherein the at least one impurity is:
 (a) a monocarboxylic acid, an alkane, or a hydroxyl acid;   (b) more polar than the 6- to 18-carbon diacid; or   (c) less polar than the 6- to 18-carbon diacid.   
     
     
         7 . (canceled) 
     
     
         8 . (canceled) 
     
     
         9 . The method of  claim 1 , wherein the at least one 6- to 18-carbon diacid is:
 (a) an α, or ω diacid;   (b) an alkane diacid or an olefin diacid; or   (c) selected from a C6 diacid (adipic acid), C7 diacid (pimelic acid), C8 diacid (suberic), C9 diacid (azelaic acid), C10 diacid (sebacic acid), C11 diacid (undecanedioic acid), C12 diacid (dodecanedioic acid), C13 diacid (tridecanedioic acid), C14 diacid (tetradecanedioic acid), C15 diacid (pentadecanedioic acid), C16 diacid (hexadecanedioic acid), C17 diacid, (heptadecanedioic acid) C18 diacid (octadecanedioic acid), and C6-18-olefin diacid.   
     
     
         10 . (canceled) 
     
     
         11 . (canceled) 
     
     
         12 . The method of  claim 1 , wherein the at least one 6- to 18-carbon diacid is:
 (a) produced by chemical means;   (b) comprises a fermentation broth from a biological mixture; or   (c) is a bioderived compound produced by fermentation.   
     
     
         13 . (canceled) 
     
     
         14 . (canceled) 
     
     
         15 . The method of  claim 1 , wherein the MBCA comprises:
 (a) three to fifteen chromatography columns;   (b) two or more zones;   (c) two zones, the eluent in the first zone containing more alcohol than the eluent in the second zone, and the second zone being downstream of the first zone with respect to the flow of eluent in the system; or   (d) a first zone, a second zone, and a third zone, the eluent in the first zone containing more alcohol than the eluent in the second zone and the third zone and the first zone being upstream of the second and third zones with respect to the flow of eluent in the system, and the eluent in the second zone containing more alcohol than the eluent in the third zone and the second zone being upstream of the third zone with respect to the flow of eluent in the system.   
     
     
         16 - 18 . (canceled) 
     
     
         19 . The method of  claim 1 , wherein the eluent comprises an aqueous alcohol. 
     
     
         20 . The method of  claim 1 , wherein the C6- to C18-carbon diacid recovery is at least 80%, 82%, 85%, 88%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, or at least 99.9% relative to the amount of the at least one impurity. 
     
     
         21 . A method for obtaining a diacid comprising:
 (a) providing a solution comprising at least one C6- to C18-carbon diacid and at least one impurity;   (b) introducing the solution into a moving bed chromatography apparatus (MBCA) having one or more chromatography columns and at least one eluent;   (c) producing a raffinate and an extract;   (d) recovering a purified C6- to C18-carbon diacid composition from the raffinate or the extract, or both, wherein said at least one impurity is present in the purified diacid composition at about 10,000 ppmw or less, about 5,000 ppmw or less, about 1,000 ppmw or less, about 500 ppmw or less, about 100 ppmw or less, about 50 ppmw or less, or about 10 ppmw or less.   
     
     
         22 . The method of  claim 21 , wherein the C6- to C18-carbon diacid recovery is at least 80%, 82%, 85%, 88%, 90%, 91%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, or at least 99.9% relative to the amount of the at least one impurity. 
     
     
         23 . The method of  claim 1 , comprising:
 (a) introducing a feed stream comprising a solution comprising adipic acid, 6-hydroxycaproic acid, and caproic acid, into a first zone of moving bed chromatography apparatus (MBCA);   (b) collecting a raffinate stream or an extract stream from the first zone of the MBCA, the raffinate stream comprising the adipic acid and 6-hydroxycaproic acid, and the extract stream comprising the adipic acid and caproic acid;   (c) introducing the raffinate stream or the extract stream into a second zone of the MBCA;   (d) collecting a second raffinate stream or a second extract stream from the second zone of the MBCA, the raffinate stream comprising the adipic acid and 6-hydroxycaproic acid, and the extract stream comprising the adipic acid and caproic acid;   (e) introducing the second raffinate stream or the second extract stream into the first zone or the second zone of the MBCA;   (f) optionally repeating steps (d) and (e) until a desired degree of separation is achieved; and   (g) collecting a final raffinate stream or a final extract stream from a zone of the MBCA, the final raffinate stream or the extract stream comprising the adipic acid, thereby separating the adipic acid from the 6-hydroxycaproic acid and caproic acid.   
     
     
         24 . The method of  claim 1 , comprising:
 (a) introducing a feed stream comprising a solution comprising dodecanedioic acid, 12-hydroxydecanoic acid and lauric acid, into a first zone of moving bed chromatography apparatus (MBCA);   (b) collecting a raffinate stream or an extract stream from the first zone of the MBCA, the raffinate stream comprising the dodecanedioic acid and 12-hydroxydecanoic acid, and the extract stream comprising the dodecanedioic acid and lauric acid;   (c) introducing the raffinate stream or the extract stream into a second zone of the MBCA;   (d) collecting a second raffinate stream or a second extract stream from the second zone of the MBCA, the raffinate stream comprising the dodecanedioic acid and 12-hydroxydecanoic acid, and the extract stream comprising the dodecanedioic acid and lauric acid;   (e) introducing the second raffinate stream or the second extract stream into the first zone or the second zone of the MBCA;   (f) optionally repeating steps (d) and (e) until a desired degree of separation is achieved; and   (g) collecting a final raffinate stream or a final extract stream from a zone of the MBCA, the final raffinate stream or the extract stream comprising the dodecanedioic acid, thereby separating the dodecanedioic acid from the 12-hydroxydecanoic acid and lauric acid.   
     
     
         25 . (canceled) 
     
     
         26 . A moving bed chromatography apparatus (MBCA) for separating a C6- to C18-carbon diacid from at least one impurity in a solution, comprising:
 (a) a first zone configured to receive a feed stream comprising a solution comprising at least one 6- to 18-carbon diacid and at least one impurity, the at least one impurity comprising a component more polar than the diacid, a component less polar than the diacid, or both;   (b) the first zone configured to produce a raffinate stream or an extract stream from the MBCA, the raffinate stream comprising the diacid and components more polar than the diacid, and the extract stream comprising the diacid and components less polar than the diacid;   (c) a second zone configured to receive the raffinate stream or the extract stream produced from the first zone;   (d) the second zone configured to produce a raffinate stream or an extract stream from the MBCA, the raffinate stream comprising the diacid and components more polar than the diacid, and the extract stream comprising the diacid and components less polar than the diacid;   (e) the MBCA configured to allow the raffinate stream or extract stream from said second zone to be reintroduced into the first zone or the second zone of the MBCA until a desired degree of separation is achieved to produce a final raffinate stream or a final extract stream from a zone the MBCA, the final raffinate stream or the extract stream comprising the diacid, thereby separating a C6- to C18-carbon diacid from the solution.   
     
     
         27 - 29 . (canceled)