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US 8,563,788B2 78 carbondioxide,andbutanolfromtheextractant,forexample oleyl alcohol, and Water. The entrainer is added to an appro priate process stream or vessel in an amount such that the ?rst mixed condensate contains suf?cient entrainer to provide phaseseparationoftheorganicandtheaqueousphases.Such phase separation typically occurs in a decanter. By “phase separation” is meant the physical formation of tWo liquid phases,onemostlyaqueousandonemostlyorganic,fromone initialliquidphasecontainingWaterandorganics.Thephysi calcharacteristicsoftheentraineranditsconcentrationinthe initial liquid phase, as Well as the concentrations of butanol and ethanol in the initial liquid phase, determine if phase separationoccursundertheselectedprocess conditions.Tem perature and pressure, for example, can also affect phase separation.Atleastaportionoftheaqueousphaseisreturned to the ?rst column; a portion of the organic phase is also returned to the ?rst column. The second column effects a separation of butanol and Water and provides butanol as a bottoms stream Which is substantially free of Water and entrainer.By“substantiallyfreeofWater”itismeantthatless 20 than about 0.01 Weight percent of Water is present in the bottoms stream. By “substantially free of entrainer” it is meant that less than about 0.01 Weight percent of entrainer is present in the bottoms stream. and a ?rst vaporous overhead stream 300 comprising Water, butanol, entrainer, and any non-condensable gas present in thefeed.An operatingtemperatureT1andanoperatingpres sure Pl at a predetermined point in the stripping section of column 650 are selected so as to provide the ?rst bottoms stream 410 comprising the extractant and Water and being substantially free of butanol and substantially free of entrainer.By “substantiallyfreeofbutanol”itismeantthat butanolcomprisesnomorethan0.01Wt% ofthebottoms 410.By “substantiallyfreeofentrainer”itismeantthatthe entrainercomprisesnomorethan0.01Wt% ofthebottoms 410. The distillation column 650 can be any conventional column having atleasta feed inlet,an overhead vapor outlet, a bottoms stream outlet, a heating means, and a suf?cient number ofstagestoeffecttheseparationofthebutanolfrom theextractant.A recti?cationsectionisrequiredWhenmini mum extractantlossinstream500isdesiredandmayormay not be combined With the use of an organic re?ux stream 490. In the case Where the extractant comprises oleyl alcohol, distillationcolumn650shouldhaveatleast5stagesincluding a re-boiler. The ?rst bottoms stream 410 can include from about 3 to about 12 Weight percent Water, less than about 0.01 Weight percent butanol, and less than about 0.01 Weight percent entrainer.Toensurethatthebottomstream410issubstan TheentrainerisaWater-immiscibleorganiccompound25 havingcharacteristicsWhichrenderitusefulintheprocesses tiallyfreeofbutanolandentrainer,theratiooftheaqueousto of the invention. The entrainer has a suf?ciently higher vapor pressure and is more volatile than the butanol isomer to be separated (or than the most volatile butanol isomer in a mix tureofbutanolisomers)toenableitsuseinthedistillations 30 describedherein.Forexample,Whentheoperatingconditions of the ?rst and/or second distillation columns include using about atmospheric pressure at the tops of the columns, the difference in vapor pressure betWeen the entrainer and the mostvolatilebutanolisomermaybeabout5toabout50psi. 35 When theoperatingconditionsincludeusinglessthanatmo spheric pressure at the tops of the distillation columns, the difference in vapor pressure may be smaller, for example about 10 to about 30 psi. Using an entrainer Which is too volatileinrelationtothebutanolcanresultinexcessive40 entrainer losses during separation or require much colder chilling media to condense and recover the entrainer. To be suitable for use, the entrainer also has a loW molar latent heat, isthermallystableundertheoperatingconditionsofthepro cess. cess,andisinertorotherWisenon-reactiveWithothercom 45 ponents in the feed stream. To be of practical use in the butanol recovery process, the entrainer is separable from butanol by distillation and has a boilingpointatatmosphericpressureWhichisloWerthanthat of the butanol to be recovered. 50 Optionally, additional stream 435 comprising Water, steam, or a mixture thereofmay be introduced into the ?rst distillationcolumn 650 ata point anyWhere along the column. If Water is used, it is preferred that the Water be fed together With aqueous stream 480, Which isreturned as liquidre?ux. If steam is used, it is preferred that the steam be fed in the stripping section or from the bottom of the column. The feed point of stream 435 may be the same as or different from the feedpointoffeedstream430.Thetotalaqueousreturntothe column isthe sum ofthe aqueous stream 480 and the optional stream435,andthetotalaqueousreturntothecolumnshould be chosen so as to be suf?cient to maintain liquid Water The entrainer can comprise at least one hydrocarbon. The entrainer can be, for example, a saturated or unsaturated, substituted or unsubstituted, aliphatic hydrocarbon. The entrainer can be a substituted or unsubstituted aromatic hydrocarbon.Forexample,theentrainermaycompriseat55 least one hydrocarbon selected from the group consisting of pentane,hexane,hexene,cyclohexane,benZene,toluene,and throughoutallthecolumntrays.Theamountofanyadded xylene.Preferably,theentrainercompriseshexane. The processes of the invention can be understood by ref erence to FIG. 1, Which illustrates one embodiment of a 60 systemusefulforpracticingtheprocessoftheinvention.The feed stream 430, obtained from a fermentation vessel (not shoWn) or an extractor (not shoWn) in a process for fermen tative extraction, is introduced into a ?rst distillation column 650,Whichhasastrippingsectionandoptionallyarectifying 65 section, at a feed point above the stripping section. The feed stream 430 is distilled to provide a ?rst bottoms stream 410 Water, steam, or a mixture thereof should also be chosen such that, in combination With aqueous stream 480, the total aque ous return to the column exceeds the butanol stream 490 returnedtothecolumnby aratiothatisgreaterthantheratio oftheaqueouscompositiontotheorganiccompositionofthe ?rst mixed condensate. The vaporous overhead stream 300 from the ?rst distilla tion column can include up to about 66 Weight percent butanol and from about 20 to about 50 Weight percent Water. Overhead stream 300 can also include about 5 to about 20 organic re?ux ?oWs to distillation column 650 should be chosensuchthattheaqueousre?ux(stream480)exceedsthe organic re?ux (stream 490) by a ratio higher than the ratio of Watertotheorganiccompositionofthe?rstmixedconden sate.Theprocessmay furthercompriseintroducingbottoms stream 410 from the ?rst distillation column into a fermenta tion vessel (not shoWn). Alternatively, bottoms stream 410 may be separated (not shoWn) to obtain a bottoms aqueous phasecomprisingWaterandabottomsorganicphasecom prising the extractant, introducing at least a portion of the bottoms organic phase into a fermentation vessel, and option ally introducing at least a portion of the bottoms aqueous phase into the same or a different fermentation vessel. The separationmaybedone,forexample,bycoolingthebottoms stream 410 until phase separation occurs. These options pro vide means to recycle the ?rst bottoms stream 410 from the butanol recovery process to the extractive fermentation proPDF Image | RECOVERY OF BUTANOL
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