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US 2011/0162954A1 Jul.7,2011 nyl alcohol (CAS No. 661-19-8), cetyl alcohol (CAS No. 36653-82-4),laurylalcohol,alsoreferredtoas1-dodecanol (CASNo.112-53-8),myristylalcohol(112-72-1),stearyl mumoleylalcohollossinstream130isdesiredandmayor alcohol (CAS No. 112-92-5), 1-undecanol (CAS No. 112-42 5), oleic acid (CAS No. 112-80-1), lauric acid (CAS No. 143-07-7), myristic acid (CAS No. 544-63-8), stearic acid (CAS No. 57-11-4), methyl myristate CAS No. 124-10-7), methyloleate(CASNo.112-62-9),undecanal(CASNo. 112-44-7),lauricaldehyde(CASNo.112-54-9),2-methylun decanal (CAS No. 110-41-8), oleamide (CAS No. 301-02-0), linoleamide (CAS No. 3999-01-7), palmitamide (CAS No. 629-54-9) and stearylamide (CAS No. 124-26-5) and mix tures thereof. In some aspects, the extractant comprises oleyl alcohol.SuitablesolventsaredescribedinUS. PatentAppli cationPublicationNo.2009030537andalsoinUS. applica tion Ser. Nos. 12/759,283 and 12/758,870 (both ?ledApr. 13, 2010), alofWhich areincorporatedhereinby reference. [0046] Theseorganicextractantsareavailablecommer cially from various sources, such as Sigma-Aldrich (St. Louis, Mo.), invarious grades, many ofWhich may be suit able for use in extractive fermentation to produce or recover butanol. Technical grades contain a mixture of compounds, including the desired component and higher and loWer fatty components.Forexample,onecommerciallyavailabletech nicalgradeoleylalcoholcontainsabout65% oleylalcohol and a mixture of higher and loWer fatty alcohols. [0047] Theinventionprovidesprocessesforseparatingor recovering butanol from a feed comprising a Water-immis cibleorganicextractant,Water,thebutanol,andoptionallya non-condensablegas.Separationofthebutanolfromthefeed is achieved through a combination of distillation and decan tation. The distillation involves the use of at least tWo distil lation columns. The ?rst column, in combination With decan tation,effectsaseparationofanynon-condensablegas,such as carbon dioxide, and butanol from the extractant, for example oleyl alcohol, and Water. The cooled overhead stream from the ?rst column is decanted into tWo liquid phases. At least a portion of the aqueous phase from the decanter is returned to the ?rst column; a portion of the organic phase is also returned to the ?rst column. The second columneffectsaseparationofbutanolandWaterandprovides a butanol bottoms stream Which is substantially free ofWater. By “substantiallyfreeofWater”itismeantthatlessthanabout 0.01Wt% ofWaterispresentbottomsstream. [0048] Theprocessesoftheinventioncanbeunderstoodby reference to FIG. 1, Which illustrates one embodiment of a systemusefulforpracticingtheprocessoftheinvention.The feed stream 100, obtained from a fermentation vessel (not shoWn) or an extractor (not shoWn) in a process for fermen tativeextraction,isintroducedintoa?rstdistillationcolumn 500,Whichhasastrippingsectionandoptionallyarectifying section, at a feed point above the stripping section. The feed stream 100 is distilled to provide a ?rst bottoms stream 110 and a ?rst vaporous overhead stream 170 comprising Water, butanol, and any non-condensable gas ifpresent in the feed. An operatingtemperatureT1andanoperatingpressureP1at apredeterminedpointinthestrippingsectionofcolumn500 are selected so as to provide the ?rst bottoms stream 110 comprising the extractant and Water and being substantially freeofbutanol.By “substantiallyfreeofbutanol”itismeant thatbutanolcomprisesnomorethan0.01Wt% ofthebottoms 110. The distillation column 500 can be any conventional column having at least a feed inlet, an overhead vapor outlet, a bottoms stream outlet, a heating means, and a suf?cient may not be combined With use of an organic re?ux stream 150.InthecaseWheretheextractantcomprisesoleylalcohol, distillationcolumn500shouldhaveatleast5stagesincluding a re-boiler. [0049] The?rstbottomsstream110canincludefromabout 3 to about 12 Weight percent Water, and less than about 0.01 Weight percent butanol. To ensure that the bottom stream 110 is substantially free of butanol, the ratio of the aqueous to organic re?ux ?oWs to distillation column 500 should be chosensuchthattheaqueousre?ux(stream160)exceedsthe organicre?ux(stream150)byaratiohigherthantheratioof Water to the organic composition of the aZeotrope. The pro cess may further comprise introducing bottoms stream 110 from the ?rst distillation column into a fermentation vessel (not shoWn). Alternatively, bottoms stream 110 may be sepa rated (not shoWn) to obtain a bottoms aqueous phase com prising Water and a bottoms organic phase comprising the extractant, introducing at least a portion of the bottoms organicphaseintoafermentationvessel,andoptionallyintro ducingatleastaportionofthebottomsaqueousphaseintothe same oradifferentfermentationvessel.The separationmay bedone,forexample,bycoolingthebottomsstream110until phase separation occurs. These options provide means to recyclethe?rstbottomsstream110fromthebutanolrecovery process to the extractive fermentation process. [0050] Optionally,additionalstream105comprisingWater, steam, or a mixture thereofmay be introduced into the ?rst distillationcolumn500atapointanyWherealongthecolumn. If Water is used, it is preferred that the Water be fed together With aqueous stream 160, 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 105 may be the same as or different from the feed point of feed stream 100. The total aqueous return to the column isthe sum ofthe aqueous stream 160 and the optional stream 105, and the total aqueous return to the column should be chosen so as to be suf?cient to maintain liquid Water throughout all the column trays. The amount of any added Water, steam, or a mixture thereof should also be chosen such that, in combination With aqueous stream 160, the total aque ous return to the column exceeds the butanol stream 150 returned to the column by a ratio that is greater than the ratio oftheaqueouscompositiontotheorganiccompositionofthe aZeotrope. [0051] Thevaporousoverheadstream170fromthe?rst distillation column can include up to about 65.6 Weight per cent butanol and at minimum about 32.5 Weight percent Water. The overhead stream includes non-condensable gas that may have been present in the feed. Stream 170 is con densed in a condenser 550 to produce a ?rst mixed condensate stream 175 comprising condensed liquid butanol and con densed liquid Water. Stream 175 also includes any non-con densablegaspresentinthefeed.The condenser550may beof anyconventionaldesign. [0052] Themixedcondensatestream175isintroducedinto a decanter 700 and alloWed to separate into a liquid butanol phase and a liquid aqueous phase. The temperature of the decanter is preferably maintained at or beloW about 400 C. to reducetheamountofbutanolandWaterbeingstrippedoutby thenon-condensablegas.Theliquidbutanolphase,thelighter liquidphase(thetopliquidphase),canincludelessthanabout number of stages to effect the separation of the butanol from theextractant.A recti?cationsectionisrequiredWhenminiPDF Image | RECOVERY OFBUTANOL FROM A MIXTURE OF BUTANOL 2011
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