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United States Patent (19) 11 Patent Number: 4,770,780 Moses 45)

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United States Patent (19) 11 Patent Number: 4,770,780 Moses 45) United States Patent (19) 11 Patent Number: 4,770,780 Moses 45). Date of Patent: Sep. 13, 1988 54 LIQUID CO/COSOLVENT EXTRACTION FOREIGN PATENT DOCUMENTS (75) Inventor: John M. Moses, Dedham, Mass. 2340566 2/1975 Fed. Rep. of Germany . 3017876 5/1982 Fed. Rep. of Germany . 73 Assignee: CFSystems Corporation, Waltham, Primary Examiner-Frank Spear Mass. Attorney, Agent, or Firm-Schiller, Pandiscio & Kusmer (21) Appl. No.: 603,563 57 ABSTRACT Disclosed are a fluid extractant, and a process and appa 22 Filed: Apr. 25, 1984 ratus for using the extractant to separate an organic liquid from an aqueous mixture. The extractant com (51) Int. Cl'.............................................. B01D 11/00 prises a first fluid solvent which is a gas in its near-criti (52) U.S. C. ....................................... 210/634; 203/16 cal or supercritical state and a cosolvent. A preferred (58) Field of Search .................... 210/634; 203/16, 19; first fluid solvent is near-critical liquid carbon dioxide. 568/913; 562/608 Preferred cosolvents are 2-ethyl hexanol for ethanol extraction, and hexanoic acid for acetic acid extraction. 56) References Cited Organic compounds such as monohydric alcohols, U.S. PATENT DOCUMENTS monoacids, ketones, ethers, aldehydes and esters can be 4,349,415 9/1982 DeFilippi et al. ................ 203/16X recovered from dilute aqueous solutions more economi 4,353,784 10/1982 Koga et al. ........................... 203/16 cally than possible by prior art processes of distillation. 4,401,514 8/1983 Kahzler et al. .......... 203/16 X 4,455, 198 6/1984 Zudkevitch et al. ................. 203/19 30 Claims, 5 Drawing Sheets COSOLVENT LIQUID Co. PRESSORED SOLVENTHO ETRACTIC NIXTURE RAFFINATE cosolyENT/C02 EXTRACT REDUCING PRESSURE PRESSURE OECONPRESSED RAFFINAE RECN: DECANTING PRESSRE WATER OROPs STILL FEED RAFFINATE DSCARE DISTILLINGSTLIN SLOWERHEAD STILL BOTTONS CONPRESSC TEMPERATURE ADJUSNG LIQUID C02 SEPARATING COSOLVENT SOLUTE PRODCT U.S. Patent Sep. 13, 1988 Sheet 1 of 5 4,770,780 COSOLVENT PRESSURIZED SOLVENT/H2O EXTRACTING MIXTURE RAFFINATE COSOLVENT/C02 EXTRACT REDUCING REDUCING PRESSURE PRESSURE DECOMPRESSED RAFFINATE REDUCING DECANTING PRESSURE WATER DROPS STILL FEED RAFFINATE DISCHARGE DSTILLING STILL OVERHEAD STILL BOTTOMS COMPRESSING HEATING TEMPERATUREADJUSTING FLASHING LIQUID C02 HEATING SEPARATING COSOLVENT SOLUTE PRODUCT A/G / U.S. Patent Sep. 13, 1988 Sheet 2 of 5 4,770,780 PRESSURE, ATMS. 2OO 5O 2O OO 8O 6O O.80 O.85 O90 O.95 ENTROPY, CAL/GM-C APPROXIMATE CO2 STATE CONDITIONS A- N EXTRACTION COLUMN B- FEED TO STILL C- OVERHEAD FROM STILL D- COMPRESSOR DISCHARGE A/G 3 U.S. Patent Sep. 13, 1988 Sheet 3 of 5 4,770,780 CN ) " ". at go 3 Liu is e H CD (2 R U s is 22- cgy O O fo of S { O o s C N co o St. ro C g O O O O C ON ONWH3 3 i? OS 3 WNW NE ONWHL 3LTOS 4,770,780 1. 2 hydrocarbon solute from an aqueous solution, the ex LIQUID CO2/COSOLVENT EXTRACTION tractant comprising a mixture of liquid carbon dioxide and a cosolvent. The latter preferably has inter alia, the This invention relates to a process and apparatus for following attributes: it is a liquid at the temperature and solvent extraction and more particularly to a process 5 pressure of the extraction process, is substantially a and apparatus for extracting large volumes of liquid better solvent for the hydrocarbon solute than for water organics from their aqueous solutions. under the extraction conditions; has a boiling point In a number of commercial processes used for manu substantially different than that of the solute, is soluble facturing many of the high-volume, liquid organic com in the liquid carbon dioxide to form a single-phase liquid pounds (such as oxygenated hydrocarbons, organic 10 under extraction conditions, and is essentially chemi sulfur compounds, organic nitrogen compounds, halo cally unreactive with either the aqueous solution or the genated hydrocarbons, organo-metallic compounds, carbon dioxide at process conditions. and the like) it is necessary to separate the organic com According to another aspect of this invention, there is pounds from aqueous solutions. In many of these mix provided a process for separating an organic liquid tures, water constitutes a major portion of the solution. 15 solute from an aqueous liquid mixture characterized by The separation of these organic compounds from water the steps of contacting at an elevated pressure the liquid may require relatively large and complex distillation mixture with a fluid extractant comprising a first sol equipment and demands a heavy expenditure of energy, vent fluid and a cosolvent of the type described, thereby if only to boil off the water. In a large number of these to form two phases, the first phase comprising an ex cases the water and organic liquids form azeotropes, 20 tract of the solute in the fluid extractant and the second often necessitating higher energy costs to even partially phase comprising water with residual cosolvent, solute break the azeotrope. and first solvent; contacting the second phase with addi At present, about 3% of the total national energy tional first solvent fluid to remove the residual cosol consumption in the United States is used for distillation vent therefrom and transfer it to said first phase; and in petroleum refining and chemical processing. It is 25 separating the first and second phases. The first solvent therefore clear that a process and/or apparatus which fluid is a gas under ambient conditions of temperature materially decreases the energy requirements for sepa and pressure which is used in its liquid near-critical or rating even a portion of such solutes from their solu supercritical state. A preferable first solvent fluid is tions, would provide a highly desirable savings in en liquid carbon dioxide e.g. carbon dioxide below its criti ergy. 30 cal temperature and at a pressure sufficiently high to It is therefore a primary object of this invention to maintain it as a liquid solvent. provide an improved fluid extractant for extracting an According to yet another aspect of this invention, organic solute from its aqueous solution. A further ob there is provided an apparatus for separating an organic ject is to provide a fluid extractant of the character liquid solute from an organic liquid solute/water combi described which minimizes the amount of fluid extract 35 nation, the apparatus comprising pressure vessel means ant which must be cycled, and reduces capital equip for effecting countercurrent contact between (1) the ment and operating costs. Yet another object is to pro combination of an organic liquid solute and water, and vide such a fluid extractant which is particularly suit (2) a pressurized extractant comprising a mixture of a able for separating from very dilute aqueous solutions, pressurized first fluid and a cosolvent of the type de chemicals such as lower alcohols and acids which are 40 scribed. Because the latter mixture is a solvent for the not readily extracted with a single solvent. organic liquid solute but substantially less for water, the Another primary object of this invention is to provide apparatus produces a fluid extract of the organic liquid an improved process for extracting liquid organic com in the extractant fluid and a raffinate comprising water pounds and the like from admixtures with water. An with minor amounts of the first solvent and organic additional object is to provide such a process which 45 liquid solute. The apparatus also comprises mixer means makes it possible to employ distillation equipment hav for mixing the first fluid and the liquid cosolvent to ing fewer stages in smaller and less complex distillation form the extractant fluid; means for introducing the equipment than now used. Yet a further object is pro extractant fluid into the pressure vessel means at a pre vide a process for extracting such organic solutes from determined level; means for introducing additional first their solvents using liquid carbon dioxide (i.e. near criti 50 fluid below the predetermined level; first distillation cal or super critical) as an extractant component, vessel for separating a still feed into an overhead vapor thereby taking advantage of many of the unique proper and first liquid bottoms and having associated therewith ties of this particular extractant including favorable reboiler means including heat exchange means for cir diffusion coefficients, low viscosity and low heat of culating a heat transfer fluid therethrough in indirect vaporization. A still further object of this invention is to 55 heat exchange relationship with the first liquid bottoms; provide such a process which uses as one component of first pressure line means connected for conveying the a fluid extractant, a nonpolluting, nontoxic and rela fluid extract as a still feed from the pressure vessel tively inexpensive fluid, i.e. carbon dioxide. means to the first distillation vessel means; vapor com Yet another primary object of this invention is to pressor means; second pressure line means incorporat provide improved apparatus for extracting organic liq ing the vapor compressor means and connected for uid solutes from their solutions, the improvement lying conveying the overhead vapor to the vapor compressor in a combination of apparatus components. An addi means and recompressed vapor therefrom through the tional object is to provide apparatus of the character heat exchange means; third pressure line means for described which makes possible the use of a fluid sol recycling the condensed vapor or supercritical fluid yent with resulting savings in energy requirements and 65 from the heat exchange means to the mixer means and capital equipment costs. to the means for introducing pressurized first fluid According to one aspect of this invention there is below the predetermined level; still bottom pressure provided a fluid extractant for extracting an oxygenated reducing means; flash tank means; fourth pressure line 4,770,780 3 4.
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