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J. GmehlingU. OnkenVAPOR-LIQUID EQUILIBRIUMDATA COLLECTIONCarboxylic Acids, AnhydridesSupplement 1Chemistry Data SeriesVol. I, Part SaPublished by DECHEMAGesellschaft fur Chemische Technik und Biotechnologie e. V.Executive Editor: Gerhard Kreysa
Bibliographic information published by Die Deutsche BibliothekDie Deutsche Bibliothek lists this publication in the Deutsche Nationalbibliographie;detailed bibliographic data is available on the Internet at http://dnb.ddb.deISBN: 3-89746-040-8 DECHEMA Gesellschaft fOr Chemische Technik und Biotechnologie e. V.Postfach 15 01 04, D-60061 Frankfurt am Main, Germany, 2002Dieses Werk ist urheberrechtlich geschOtzt. Alle Rechte, auch die der Obersetzung, desNachdrucks und der Vervielfaltigung des Buches oder Teilen daraus sind vorbehalten.Kein Teil des Werkes dart ohne schriftliche Genehmigung der DECHEMA in irgendeinerForm (Fotokopie, Mikrofilm oder einem anderen Verfahren), auch nicht fOr Zwecke der Un terrichtsgestaltung, reproduziert oder unter Verwendung elektronischer Systeme verarbei tet, vervielfaltigt oder verbreitet werden.Die Herausgeber Obernehmen fOr die Richtigkeit und Vollstandigkeit der publizierten Oatenkeinerlei Gewahrleistung.T his work is subject to copyright. All rights are reserved, whether the whole or part of thematerial is concerned, including those of translation, reprinting, reproduction by photo copying machine or similar means.No part of this work may be reproduced, processed or distributed in any form, not even forteaching purposes - by photocopying, microfilm or other processes, or implemented inelectronic information storage and retrieval systems -without the written permission of thepublishers.T he publishers accept no liability for the accuracy and completeness of the published data.T his volume of the Chemistry Data Series was printed using acid-free paper.Technical Production: Mitterweger & Partner, Plankstadt
Vapor-Liquid EquilibriumData CollectionSaCarboxylic Acids, AnhydridesSupplement 1Tables and diagrams of data for binary andmulticomponent mixtures up to moderate pressures.Constants of correlation equations for computer use.J. Gmehling,U. OnkenTechnische ChemieUniversitat Oldenburg
SaCarboxylic Acids, AnhydridesSystems with:Aliphatic and aromatic carboxylic acidsAcetic AcidLauric AcidAcrylic AcidMethacrylic AcidBenzoic AcidZ-9-0ctadecenoic AcidButyric Acid3-Pentenoic Acid (isomer not specified)Chloroacetic AcidPropionic AcidDichloroacetic AcidTrichloroacetic AcidFormic AcidTrifluoroacetic AcidHexanoic AcidValeric AcidIsobutyric AcidAnhydridesAcetic AnhydrideMaleic Anhydride
viiAUTHORS' PREFACEWith this volume we have pleasure in publishing a new supplement of the Vapor Liquid Equilibrium Data Collection for carboxylic acids and anhydrides asDECHEMA Chemistry Data Series Volume I Part 5a.The data in this book are taken from the Dortmund Data Bank and are available inelectronic form. The Dortmund Data Bank covers a wide range of properties inEaddition to the V LE, h , yoo, for example: data bases of the vapor-liquid equilibriaof low boiling substances (HPV), azeotropic data (AZD), gas solubilities (GLE),solid-liquid equilibria (SLE) and a pure component property data base (PCP). Datain electronic form can be obtained from DDBST GmbH, Oldenburg, Germany orDECHEMA e.V., Frankfurt am Main. Data collections for inhouse use are availablefrom DDBST GmbH; DECHEMA e.V.; FIZ Chemie GmbH, Berlin, Germany andAspen Technology, Inc., Cambridge, Massachusetts, USA. D DBST GmbH canalso supply a large program system well suited to handling the data in the databanks. Online versions of the database are hosted by STN International(Columbus, Ohio, USA; Karlsruhe, Germany and Tokyo, Japan) and DECHEMAe.V. (via the Internet).We would like to thank J. Krafczyk and J. Menke for computer programmingassistance in order to allow publication of data determined under non-isothermand non-isobaric conditions. In addition we would like to sincerely thank all thosecolleagues who have both supported and continue to support the endeavours ofthe thermodynamic group at the University of Oldenburg by delivering V LE datafrom their research. At this juncture we would like to request other colleagues inthis field to send us unpublished data and reprints of their publications onthermophysical properties.Oldenburg, November 2002J. GmehlingU. Onken
viiiEXECUTIVE EDITOR'S PREFACET heaimofDECHEMAe.V.,T heSocietyforChemical Technology andBiotechnology when it was founded in 1926 was to improve cooperation betweenchemist and engineer. As the importance of mathematical modelling, computersimulation and optimisation became apparent in the mid-nineteen-seventies, thisideal resultedin theproduction andpublication ofcollections of basicthermophysical data in both electronic and book form. T his is not data that couldhave easily found a publisher outside the engineering societies, because of itssheer volume and limited circle of interest. By its sponsoring and publication ofthe DECHEMA Chemistry Data Series DECHEMA e.V. has been associated withthese endevours for over a quarter of a century. Much of the original work todetermine the values obtained was financed by the German Ministry of Research.lt is to be hoped that publication of this data collection by DECHEMA e.V. in theDECHEMAChemistryDataSerieswill inspireotherauthors toconsiderpublishing their collections of thermophysical data. DECHEMA e.V. is alwayspleased to assist colleagues from the thermophysical data community inpreparing their results, their studies, their collections and their assessments forpublication. D ECHEMA e.V. is always prepared to enlarge the scope of theDECHEMA Chemistry Data Series and is thus pleased to hear from readers,designers, scientists and engineers of areas where thermophysical data is notavailable or scarce. We hope that the end user finds the data of utility and ofinterest.Frankfurt am Main, November 2002Gerhard Kreysa
ixCONTENTS6-/Vol. I, Part aSubjects of Volume I . . . VIAuthor's Preface . . VIIExecutive Editor's Preface . . VIIIContents Volume I, Part Sa . IXGuide to Tables . . . XIList of Symbols . . . XXIReferences . XXIIIData TablesCarboxylic AcidsBinary SystemsFormic Acid . .Trichloroacetic Acid . 21Trifluoroacetic Acid . . 27Dichloroacetic Acid . 28Chloroacetic Acid . . 30Acetic Acid . . . . 36Acrylic Acid . 155Propionic Acid . . 166Methacrylic Acid . . 2 19Butyric Acid . . . . . . 236Isobutyric Acid . 2503-Pentenoic Acid (isomer not specified) . 260Valeric Acid . . . 263Hexanoic Acid . 267Benzoic Acid . 270Lauric Acid . . 280Z-9-0ctadecenoic Acid . 283Ternary Systems . 284Quaternary Systems . . 305Anhydrides.Maleic Anhydride . . . 306Acetic Anhydride . 3 12
XAppendix A: Pure Component Parameters . . . . . . . . . . . . . . 329Appendix B: Dimerization Constants of Carboxlic Acids347Formula Index of Binary Systems . . . . . . . . . . . . 349Formula Index of Ternary Systems . . . . . . . . . . . . . . . . . . . 362Formula Index of Quaternary Systems . . . . . . . . . . . . 364Alphabetical Index of Binary Systems . . . . . . . . . 365Alphabetical Index of Ternary Systems . . . . . . 378.Alphabetical Index of Quaternary Systems . . . . . . . . . 380
028HN03Sulfur DioxideNitric AcidC2H 02Acetic Acid36C Hs03Acetic Anhydride312C2HCI302Trichloroacetic Acid21-24C2H3CI02Chloroacetic Acid30C2H 02Acetic Acid37H20 SSulfuric AcidC2H3CI02Chloroacetic Acid31CCI4TetrachloromethaneC2H402Acetic Acid38-42RC3Hs02Propionic Acid166-172C.Hs03Acetic Anhydride313-319RC.H603Acetic Anhydride322C.Ha02Butyric Acid236C,aH3.o2Z-9-0ctadecenoic Acid283C2HCI302Trichloroacetic Acid25C2H2CI202Dichloroacetic Acid283C2H3CI02Chloroacetic Acid32IllC2H 02Acetic Acid43C Hs02Methacrylic Acid219C2H3NAcetonitrile1::Ja.CD C2H 02Acetic Acid2-70Methyl l Acetate::JIll13' Propionic Acid14-16C3H1NON,N- Dimethylformamide (DMF)17(/)' CIJCsHsNPyridine18-19CDCsH,002Valeric Acid20CIJcs2CHCI3CH202Carbon DisulfideChloroformFormic Acid110"""''c-"""''ro 3U) 0
"'T1CH3CIMethyl ChlorideC.Hs03Acetic Anhydride320CH31Methyl IodideC2H402Acetic Acid44C Hs03Acetic Anhydride321cc.H2o3Maleic Anhydride306IllHN03Nitric neTrichloroacetic Acid0"""'3::::::1a.CDXC2HF302Trifluoroacetic AcidC2H 02Acetic Acid27C2H2CI202Dichloroacetic AcidCHCI3Chloroform28CsHsBenzene29llJHN03Nitric Acid30IllH2o.sSulfuric Acid31CHCI3Chloroform32CsH1o02N-Pentanoic Acid33-35CsHsBenzene26CDCH202Formic Acid1(/JC2H3CI02C2H3NChloroacetic AcidAcetonitrileC2H4CI21 ,2-DichloroethaneC2H 02Acetic AcidC2H402Acetic Acid45-47C3Hs02Propionic Acid173-174C Hs02Isobutyric Acid250-251C4H602Methacrylic Acid220028Sulfur Dioxide36HN03Nitric Acid37CCI4Tetrachloromethane3 8-42RCHCI3Chloroform43CH202Formic Acid2-7CH31Methyl Iodide44C2HF302Trifluoroacetic Acid270.::::::1 (J)' (/Jro 3Ulc.n0
Acetonitrile45-47C2H51Ethyl opene52-53C3Ha02Methyl Acetate54-57C2H3NPropionic Acid58--64RC3H7BrPropyl Bromide65--69RC3H7NON,N-Dimethylformamide (DMF)70-71C4H5CI302Ethyl ylic Acid74Vinyl Acetate75'T10C.Ha03Acetic Anhydride76-79C Hs02Butyric Acid80-823Ethyl Acetate83-95IllC.HgNON ,N- Dimethylacetamide96C5H5NPyridine97-100C5Hs02Vinyl Propionate101-102::Ja.CD C5H,o02Propyl nyl Butyrate113-114CaH,oO Acetaldehyde Diacetate115-117Ethylene Glycol Diacetate118CD6-Caprolactam119C/) c:. (f)' C/)-C6H11NO3(.,)c.n.
"'T1Cyclohexane12Q-1231-Hexene124Butyl Acetate125-126cIsobutyl Acetate127-129ROlHexane130CsH1 0 Diethyl Malonate140C1H,402Pentyl nitrile146CaH,aOctane147-148C9H,o02Benzyl 52C10H 1sCamphene153C,2H2o02Isobornyl Acetate154Methyl FormateCH202Formic Acid8-11C2Hs lEthyl IodideC2H402Acetic Acid48-49C2HsNOAcetamideC2H402Acetic Acid50-51C4Hs02Methyl Acrylate155-158CsHa02Ethyl CsH 02Acrylic Acid0""" :30-:::J (/)' CIJ-CD3CIJ 0'11\)
C3H5CICsHs023-Chloro-1-PropeneMethyl AcetatePropionic AcidCsH2oNonane164C10H22Decane165CH202Formic Acid12C2H 02Acetic Acid52-53CH202Formic Acid13C2H 02Acetic Acid54-57C.H802Butyric Acid237CCI4Tetrachloromethane166-172CH202Formic Acid14-16C2Hs NAcetonitrile173--174C2H 02Acetic Acid58-MRC3H7BrPropyl Bromide175-179C.Hs OsAcetic Anhydride180--183C Hs02Butyric Acid184-186Ethyl Acetate187QlIsobutyric Acid188CsH5NPyridine189--190C5H,o02Ethyl Propionate191-198R:::Jc.CD CsHsBenzene199-200R0CsH7NAniline201-202OJCsH,o OsPropionic Acid, ene209CsH1202Butyl Acetate210en' .Ql.,.' .3c.u()1c.u
C3H1BrC3H1NOC4H203Propyl BromideC 1H1sHeptane214-218R.,C2H 02Acetic Acid65-69R C3Hs02Propionic Acid175-179cFormic Acid17ll C2H402Acetic Acid70--71CH3N02Nitromethane306C Hs02Methyl Acrylate307::Ja.CDXC Hs02Ethyl Acetate308N,N-Dimethylformamide (DMF) CH202Maleic AnhydrideCsHsBenzene309CaH,oXylene (isomer not specified)311o-Xylene310030.OJ::Jll - (/)' (J)C4H5CI302Ethyl TrichloroacetateC2H 02Acetic Acid72C4H60MethacroleinC2H 02Acetic Acid73C Hs02Methacrylic thane220C2H402Acetic Acid74C4Hs02Methacrylic 6C8H1402Butyl zene230CaH,o-3(,)01""'
Methyl AcrylateVinyl AcetateC4Ha03Acetic Undecane234c,2H2aDodecane235C3H402Acrylic Acid155-158C4H203Maleic Anhydride307C2H402Acetic Acid7502SSulfur Dioxide312CC14Tetrachloromethane313-319Rcs2Carbon Disulfide322CH3CIMethyl Chloride320CH31Methyl Iodide321.,C2H402Acetic Acid76-79""""C3Hs02Propionic Acid18Q-183C4Hs02Butyric Acid238IllEthyl Acetate323Isobutyric Acid252CsH1o02Isopropyl Acetate324-325:::Ja.CD CsH,o04Acetaldehyde sOctane336-337cs2Carbon Disulfide236CDC2H402Acetic Acid80-82rJJ03c-- (f)' rJJ.- C4Hs02Butyric Acid3w()1()1
Ethyl AcetateIsobutyric Acid,Methyl Acetate237Propionic Acid184-186C.Hs03Acetic Anhydride238s::C sH s 43C7HsToluene244:::Ja.CD C7H, 02Pentyl Acetate245Propyl Butyrate246CaH,s02Butyl Butyrate247C9H2oNo
C.Hs03 Acetic Anhydride 313-319R cs2 Carbon Disulfide C.H603 Acetic Anhydride 322 C.Ha02 Butyric Acid 236 C,aH3.o2 Z-9-0ctadecenoic Acid 283 11 CHCI3 Chloroform C2HCI302 Trichloroacetic Acid 25 0 """'' C2H2CI202 Dichloroacetic Acid 28 3 c C2H3CI02 Chloroacetic Acid 32 Ill C2H 02 Acetic Acid 43 ::J C Hs02 Methacrylic Acid 219 a.
