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US 8,563,788B2 56 The term “fatty amide” as used herein refers to an amide having a long, aliphatic chain of C12 to C22 carbon atoms, Which is either saturated or unsaturated. Non-condensablegasmeans agasthatisnotcondensedat an operating temperature of the process described herein. The terms “° C.” and “C” mean degrees Celsius. The term “deg” means degrees. The term “g/L” means grams per liter. The term “ppm” means parts per million. The term “kg/hr” means kilograms per hour. The term “atm” means atmosphere. Butanol-containing extractant streams useful as a feed in butanol. In embodiments, the extractant preferentially parti tions butanol from the aqueous phase by at least a 2:1 con centration ratio, such that the concentration of butanol in the extractantphaseisatleasttWotimesthatintheaqueousphase When evaluatedinaroom-temperatureextractionofanaque ous solution of butanol. In embodiments, the extractant pref erentially partitions butanol from the aqueous phase by at least a 3:1 concentration ratio, by at least a 4:1 concentration ratio, by at least a 5:1 concentration ratio, by at least a 6:1 concentrationratio,byatleasta8:1concentrationratio,byat least a 10:1 concentration ratio or by at least a 20:1 concen trationratio. To be of practical use in the butanol recovery process, the extractant is separable from butanol by distillation, having a boiling point at atmospheric pressure Which is at least about 30 degrees Celsius higher than that of the butanol to be recovered, or for example at least about 40 degrees higher, or forexampleatleastabout50degreeshigher.A mixtureof higher boiling extractants is expected to behave in a funda mentallysimilarWaytoasingleextractantprovidedthatthe boilingpointofthemixture,ortheboilingpointoftheloWest boilingsolventofthemixture,issigni?cantlyhigherthanthe boilingpointsofWaterandbutanol,forexampleatleastabout 30degreeshigher. The extractant can comprise at least one solvent selected from the group consisting of C7 to C22 fatty alcohols, C7 to C22fattyacids,estersofC7toC22fattyacids,C7toC22fatty aldehydes,C7toC22fattyamides,andmixturesthereof.The extractant can comprise at least one solvent selected from the groupconsistingofC12toC22fattyalcohols,Cl2toC22fatty acids, esters of C12 to C22 fatty acids, Cl2 to C22 fatty alde hydes, Cl2 to C22 fatty amides, and mixtures thereof. Examples of suitable extractants include an extractant com prisingatleastonesolventselectedfromthegroupconsisting ofoleylalcohol,behenylalcohol,cetylalcohol,laurylalco hol,myristylalcohol,stearylalcohol,oleicacid,lauricacid, myristicacid,stearicacid,methylmyristate,methyloleate, lauricaldehyde,1-nonanol,1-decanol,1-undecanol,2-unde canol, 1-nonanal, 2-butyloctanol, 2-butyl-octanoic acid and mixturesthereof.Inembodiments,theextractantcomprises oleyl alcohol. In embodiments, the extractant comprises a branched chain saturated alcohol, for example, 2-butyloc tanol,commerciallyavailableasISOFAL® 12(Sasol,Hous ton, Tex.) or Jarcol I-12 (Jarchem Industries, Inc., Newark, N.J.). In embodiments, the extractant comprises a branched chain carboxylic acid, for example, 2-butyl-octanoic acid, 2-hexyl-decanoic acid, or 2-decyl-tetradecanoic acid, com merciallyavailableasISOCARB® 12,ISOCARB® 16,and ISOCARB® 24,respectively(Sasol,Houston,Tex.). Such organic extractants can be available commercially from various sources, such as Sigma-Aldrich (St. Louis, Mo.), in various grades, many of Which may be suitable for use in extractive fermentation to produce or recover butanol. Technical grades contain a mixture of compounds, including thedesiredcomponentandhigherandloWerfattycompo nents. For example, one commercially available technical gradeoleylalcoholcontainsabout65% oleylalcoholanda mixtureofhigherandloWerfattyalcohols. The invention provides processes for separating or recov eringbutanolfromafeedcomprisingaWater-immiscible organic extractant, Water, at least one isomer of butanol, and optionally a non-condensable gas. Separation of the butanol from the feed is achieved through a combination of distilla tion, decantation, and the use of an entrainer. The distillation involvestheuseofatleasttWodistillationcolumns.The?rst column, in combination With the entrainer and decantation, effects a separation of any non-condensable gas, such as the processes of the invention include any organic phase obtained from an extractive fermentation Wherein butanol is producedasafermentationproduct.Typicalbutanol-contain ingextractantstreamsincludethoseproducedin“drygrind” or“Wetmill”fermentationprocessesinWhichinsituproduct removalispracticedusingliquid-liquidextractionofthefer mentation broth With an organic extractant. After extraction, theextractantstreamtypicallycomprisesbutanol,Water,and the extractant. The extractant stream may optionally com prise a non-condensable gas, Which can be a gas that is inert or otherWise non-reactive With other feed components under theoperatingconditionsofthepresentinvention.Suchgases can be selected from gases in the group consisting of, for example, carbon dioxide, nitrogen, hydrogen, noble gases such as argon, or mixtures of any of these. The extractant stream may optionally further comprise fermentation by-products having su?icient solubility to partition into the extractantphase.Theextractantstreammayoptionallycon tain solids, for example biomass or solids from the fermen tation.Butanol-containingextractantstreamsusefulasafeed in the processes of the invention include streams character iZed by a butanol concentration in the feed from about 0.1 Weightpercenttoabout40Weightpercent,forexamplefrom about 2 Weight percent to about 40 Weight percent, for example from about 5 Weight percent to about 35 Weight percent, based on the Weight of the feed. Depending on the ef?ciencyoftheextraction,theaqueousphasetiterofbutanol inthefermentationbrothcanbe,forexample,fromabout5 40 g/L to about 85 g/L, or from about 10 g/L to about 40 g/L. In embodiments,theeffectivetiterofbutanolrecoveredfromthe process is at least about 40 g/L, at least about 50 g/L, at least about 60 g/L, at least about 70 g/L, at least about 80 g/L, at least about 90 g/L, or at least about 100 g/L. 45 Butanol-containingextractantstreamsusefulasafeedmay further comprise ethanol. Such extractant streams may be characterized by a butanol concentration as described above herein and by an ethanol concentration in the feed from about 0.01Weightpercenttoabout10Weightpercent,forexample 50 fromabout0.2Weightpercenttoabout2Weightpercent,for example from about 0.5 Weight percent to about 1 Weight percent, based on the Weight of the feed. Depending on the ef?ciencyoftheextraction,theaqueousphasetiterofethanol inthefermentationbrothcanbe,forexample,fromabout0.1 55 g/L to about 20 g/L, or from about 1 g/L to about 5 g/L. The ethanol may be obtained in the fermentation broth as a by product from recombinant butanol-producing microorgan isms,forexample. TheextractantisaWater-immiscibleorganicsolventor60 solventmixturehavingcharacteristicsWhichrenderituseful for the extraction of butanol from a fermentation broth. The extractantpreferentiallypartitionsbutanolfromtheaqueous phase,forexamplebyatleasta1.1:1concentrationratio,such thattheconcentrationofbutanolintheextractantphaseisat 65 least1.1timesthatintheaqueousphaseWhen evaluatedina room-temperature extraction of an aqueous solution of 20 25 30 35PDF Image | RECOVERY OF BUTANOL
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