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`PARANMflfiR$
`m".=c“!
`€3THEH€fi}HESMMfi
`}¥%@MWETERS
`
`MYLAN PHARMS. INC. EXHIBIT 1044 PAGE 1
`
`

`
`Library or Congress Cataiaging-in-Pubiicatian Data
`
`Hanan. Allan F. M.
`
`CRC handbook of 3u}ubi)iIy parameters and other cohesion
`parameters I Allan F. M. Barton.
`-- 2nd ed.
`p.
`cm.
`
`Includes bibliographical references and index.
`ISBN 9349341176-9
`I. Soiubilily. 2. Cohesion. 1. Title
`QD543.B22 1991
`541.3 ’4 2--dc20
`
`
`
`
`
`
`
`MYLAN PHARMS. INC. EXHIBIT 1044 PAGE 2
`
`consent item the publisher.
`
`Direct all inquiries to CRC Press, Inc.. 2000 Corporate Blvd., N.W., Boca Raton, Florida 33431.
`
`"' 1991 by CRC Press. Inc.
`
`Entematicrnal Starndard Book Number D-8493-0176-9
`
`Ijbmry of Cungmess Card Number 91-18630
`
`Printed in the United States ofAmerica
`
`I 2 3 4 5 6 7 B 90
`
`

`
`Chapter 2
`
`TI-IERMODYNAMICS
`
`23
`
`2.1 COHESIVE ENERGY
`
`If U is defined as the molar internal energy (the molar potential energy of a material
`relative to the ideal vapor at the same temperature}, then U has a numerically negative value
`for a condensed material. It follows, therefore, that the molar cohesive energy (the energy
`associated with the net attractive interactions of the material and defined as — U) has a
`positive value.
`
`can be divided into two parts:
`
`I.
`2.
`
`The molar vaporization energy, ,AgU, required to vaporize one mole of the liquid to
`its saturated vapor
`The energy, EANU, required to expand the saturated vapor to infinite volume at constant
`temperature; that is, the energy necessary to completely separate the molecules
`
`As presented by Polak,’ this can be expressed
`
`—U = ,A,U + ,,.A_,IJ = ,A,u + LEV (av/aV),dV
`
`(1)
`
`V‘m
`
`according to the relationship
`
`(2)
`—U=,AsH+,,A,.,H—RT+p,'V
`where 131,11‘ is the molar vaporization enthalpy; ELLE is the enthalpy change (increase) on
`isotherrnally expanding 1 mol of saturated vapor to zero pressure; p, is the saturation vapor
`pressure at temperature T; ‘V is the molar volume ofthe liquid (the superscript I is frequently
`omitted if there is no chance of ambiguity); and 1? gas constant (8.314-41 .1 K“ mot").
`At pressures below atmospheric pressure (that is, at temperatures below the normal boiling
`point) SANH and p,‘V are usually negligible compared with AEH and RT:
`
`(3)
`-U=,A,,U=,figH—RT
`However, at higher pressures the other terms cannot be neglected, and in fact at the critical
`point pig}! is zero, so Equation 3 erroneously leads to a negative vaiue for the cohesive
`
`
`
`MYLAN PHARMS. INC. EXHIBIT 1044 PAGE 3
`
`

`
`24
`
`CRC Handbook of Solubility‘ Parameters and Other Colzerion Parameters
`
`energy while the full Equation 2 correctly predicts a small positive cohesive energy at the
`critical point. Values of ,dgH, A530, and -—U for various liquids at their normal boiling
`points in Table 1 illustrates typical variations in these quantities.
`Svoboda and co-workers“ have recently considered the cohesive energies of liquids in
`some detail, and Table 2 summarizes their recommended 25°C values.
`
`2.2 COHESIVE PRESSURE AND THE HILDEBRAND
`PARAMETER
`
`The stabilizing or cohesive effect in condensed phases can be expressed in terms of the
`cohe.rivepre.rsure which is dimensionally identical with the cohesive energy density (cohesive
`energy per unit volume),
`
`r: = —UfV
`
`(4)
`
`Cohesive energy density was the basis of the original definition by Hildebrand and
`Seott"‘° of what is now generally called the Hildebrand solubility parameter or Hildebrand
`parameter,
`
`a = as
`
`<— Urv)“ ~= (IA; um”
`
`(53
`
`This parameter was intended for nonpolar, nonassociating systems, but the concept has been
`extended to all types of systems.
`The term “solubility” parameter, which has been used Widely, is really too restrictive
`for a quantity that may be used to correlate such a wide range of physical and chemical
`properties." The name "cohesion parameter" is preferred by the author for the group of
`parameters with dimensions of (pressure)"’ that includes the Hildebrand parameter as defined
`in Equation 5. Use of the proposed alternative title “interaction paraznetermz would result
`in confusion with the polymer-liquid interaction parameter x {Chapter 13) and several other
`binary interaction parameters characterizing pairs of substances.
`The title "solubility parameter" and the form of Equation 5 suggest a close link between
`the phenomena of “solubility” or “miseibility" and those of “cohesion” and “vaporiza-
`tion.” This similarity can be appreciated by considering what happens in a mixing process:
`the “like" molecules of each component in a mixture become separated from one another
`by what approximates to an infinite distance, comparable in some respects to what happens
`in the vaporization process. The Hildebrand parameter is sometimes called the “total"
`cohesion paralneter, 3,, because there are various “componcnt" cohesion parameters, but
`the subscript “t” is usually omitted if this can be done without ambiguity.
`From Equations 3 and 5 it is clear that the Hildebrand parameter of a liquid may be
`readily evaluated if the molar volume and molar vaporization enthalpy have been determined
`at the required temperature, and if that ternperatun: is well below the normal boiling point
`of the liquid:
`
`3 = (,AgH — RT)"":'V"’
`
`(6)
`
`This density and enthalpy tniormation is readily available for some liquids, but for many
`other liquids and for all polymers, solids, and surfaces it is necessary to use indirect evaluation
`methods, described in subsequent chapters, for the estimation of cohesion parameters.
`Table 3 lists selected values of Hildebrand parameters, molar volumes and molar va-
`porization enthalpies at 25°C, reported by Hildebrand, Prausnitz, and Scott” and presented
`here in SI units {see Section 2.5). The vaporization enthalpies are corrected for expansion
`
`MYLAN PHARMS. INC. EXHIBIT 1044 PAGE 4
`
`

`
`‘KEYS
`
`energy at the
`011113! boiling
`
`s of liquids in
`
`ND
`
`:2 terms of the
`
`zsiry (cohesive
`
`(4)
`
`fildebrand and
`or Hfldebrand
`
`(5)
`
`icept has been
`
`too resirictive
`and chemical
`
`.- the group of
`eter as defined
`1' would result
`1 several other
`
`3 link between
`
`RC1 “vaporiza-
`ixing process:
`[B one another
`
`what happens
`:1 lhe “tota1"
`arameters, but
`
`liquid may be
`en deterrnined
`
`1 boiling point
`
`(6)
`
`but for many
`rectevaluation
`ITBIIICICIS.
`
`:-.nd molar va-
`
`and presented
`for expansion
`
`TABLE 1
`Calculated Values of Molar Vaporizaiion Enthnlpies, Molar Vaporization
`Energies and Molar Cohesive Energies for Liquids at their Normal Boiling
`Points
`
`Liquid
`
`Acetone, 2—propanane
`Ammonia
`Aniline
`Benzene
`Bromine
`Bromobcnzene
`
`Bromeethane. ethyl bromide
`Butane
`I-Butenol
`2-Butane!
`car:-Butane]
`1-Butene
`ci.r—2-Butene
`1‘mr:.:r—2-Blatene
`Carbon disulfide
`Chlnroiienzene
`Chloroetlram.-, ethyl chloride
`1-Chloropropane, propyl chloride
`.9-Cresol, 2—methy!pheao1
`m—Cresol. 3-mei.11y2phenoI
`p-Cresoi, 4—rne£hylpl1eml
`Cyclohexane
`Cyciupcmane
`1,2-Dibmmoethane, ethylene dibromide
`Dichlorodiflmmrnetiune
`1.i—Dichioroe1.hanc
`1,2-Elichloroethane, ethylene dichloride
`Dichlorcrmethane
`Diethyl ether
`Dimethylamine
`2,2-Dimelhylburane
`2,3-Dimethylbuzane
`Dimethyl ether
`2,2—Dimetl1yi1:1n:>pane, noopentanc
`Ethanol
`Ethyl acetate
`Ethylbenzene
`Ethyl formate
`Edayl propionate
`Hcptane
`Hexane
`1-Hexene
`cit-2-Hexene
`trans-2-Hexene
`ml!‘-3—HeJI:eIIe
`mm.r—3—1-lexene
`Hydmzine
`2-Propane]
`Methanol
`Methyl acetate
`Mezhylamine
`2-Methylhutanc, isopemane
`Meihyi format:
`
`fJ"C
`
`56.1
`-33.3
`184.2
`89.1
`58.7
`155.9
`38.4
`-0.5
`117.5
`108.0
`82.9
`-6.3
`3.7
`0.9
`46.2
`131.?
`32.2
`46.6
`190.8
`202.2
`201.3
`30.?
`49.3
`131.5
`-29.8
`57.3
`83.?
`39.8
`34.6
`6.9
`49.‘!
`58.0
`-24.8
`9.5
`78.3
`7?.1
`136.2
`54.0
`98.9
`98.4
`63.7
`63.3
`68.8
`68.0
`66.8
`67.3
`113.1
`82.2
`64.5
`56.9
`-6.4
`27.9
`31.8
`
`A.H:'|r..l
`mo!"
`
`AUM
`mi}
`
`-UIIIJ
`mop:
`
`29.7
`23.5
`43.9
`30.3
`29.3
`37.5
`25.3
`22.4
`43.5
`42.9
`39.9
`22. 1
`23.3
`22.3
`23.7
`35.4
`24.5
`27.5
`45 .5
`43. 1
`48.0
`30.9
`22.3
`35.1
`20.1
`29.0
`32.2
`23.:
`26.5
`24.2
`25.3
`27.3
`2: .5
`22.2
`39.4
`32.1
`35.3
`29.9
`33.9
`31.9
`23.9
`23.3
`29.9
`23.9
`23.3
`29.0
`41.5
`40.3
`35.4
`39.4
`26.2
`24.7
`23.5
`
`27.0
`21.5
`40.2
`27.9
`25.6
`34.2
`24.3
`20.3
`40.5
`39.9
`37.1
`20.1]
`21.1
`213.6
`24.1
`32.2
`22.3
`25.0
`41.8
`44.2
`44.2
`27.2
`24.7
`32.8
`18.1
`26.3
`29.3
`25.6
`24.1
`22.5
`23.7
`24.7
`19.5
`20.5
`36.6
`29.4
`32.5
`27.3
`31.0
`28.9
`26.2
`25.7
`26.3
`26.2
`26.1
`26.3
`38.4
`37.8
`33.7
`27.?
`224.0
`22.3
`26.0
`
`27.2
`21.7
`40.5
`23.2
`26.8
`34.5
`24.5
`20.5
`40.8
`40.2
`37.4
`20.2
`21.3
`20.8
`24.3
`32.5
`22.5
`25.2
`42.2
`44.6
`44.5
`27.4
`25.0
`33.1
`18.3
`26.6
`29.5
`25.8
`24.3
`22.7
`24.0
`25.0
`19.7
`20.8
`36.9
`29.’?
`32.9
`27.5
`31.3
`29.3
`26.6
`26.0
`26.6
`26.5
`26.4
`26.6
`38.5
`33.1
`33.9
`28.8
`24.2
`22.6
`26.2
`
`
`
`MYLAN PHARMS. INC. EXHIBIT 1044 PAGE 5
`
`

`
`26
`
`CRC Handbook of Solubility Parameters and Other Cohesion Parameters
`
`TABLE 1 {continued}
`Calculated Values of Molar Vaporization Enthalpies, Molar Vaporization
`Energies and Molar Cohesive Energies for Liquids at their Normal Boiling
`Points
`
`Liquid
`
`2-Mcthyipentanc
`2-Melhylpropzne, isobutsnc
`2-Methylpropene, isobutyleme
`Methyl propionaie
`Octane
`Penlane
`1-Penzcne
`cir-2-Pentcne
`rm:-is-2-Pentene
`Phenol
`Propane
`1—Propanol
`P1-opionic acicl
`Propyl acetate
`Propylene, propane
`Tea-acblorometbane
`1,2,3,5-Tctramediylbenzenc
`1 ,2,4,5—'1‘euso1el11y1bc.n7ene
`Toluene, rrretbyibcnzene
`Trichloromczharre, chloroform
`Triniethyiarnirie
`1,2,3-Trimelhylbeuzene
`1 ,2,4—Trim.e1hylbe11zEne
`Waler
`9-Xyierie,1,2-dimefliylbenzeoe
`m—Xy1ene,1,3-dimethylbenzeoc
`p-Xy1ene,l ,4-dimezhyfbenrrene
`
`r,;°C
`
`60.3
`— 1 1 .4
`— 6.9
`79.4
`125.7
`36.1
`29.5
`36.5
`36.3
`181.8
`-42.1
`97.2
`141.0
`101.5
`— 47.‘?
`76.6
`198.0
`196.8
`110.6
`61.?
`2.9
`i76.1
`169.4
`100.0
`144.4
`139.1
`138.3
`
`A3531
`moi“
`
`a4.U!"|-1
`mol"
`
`" WU
`mol"
`
`27.9
`21.2
`22 .1
`32.1
`34.6
`25.3
`25.3
`26.4
`26.1
`46.6
`18.3
`4-2 .1
`42.3
`34.1
`1.8.5
`30.4
`42.5
`42.4
`33.4
`29.1
`24.1
`39.9
`39.3
`48.8
`36.7
`36.2
`35.9
`
`25.2
`19. 1
`20.0
`29.3
`31.4
`23.4
`22.9
`23 .9
`23.‘!
`43.0
`17.0
`38.4
`39.0
`31.2
`16.?
`27.6
`38.8
`38.7
`30.3
`26.4
`21.9
`36.3
`35.8
`37.8
`33.4
`32.9
`32.7
`
`25.5
`19.3
`20.2
`29.6
`31.9
`23.7
`23.1
`24. 1
`24.6
`43.4
`17.1
`38.7
`39.3
`31.5
`16.8
`27.9
`39 .2
`39. S
`30.6
`26.3‘
`22.1
`36.’!
`36. 2
`37.9
`33.7
`33.3
`33.0
`
`Adapted from Polak, 1, Collect. Czech. Chem. Cornmwm. 31, 1483, 1966
`
`to the ideal gas state where possible. Substances the: are solids at 25°C have been treated
`as subcooled liquids {see Chapter 12). Similar information on cohesive energy densities was
`provided by Varushchenko, Loseva, and Dru-.—:hina‘” for 1,1,- 1,I- and o,m-dicb1ozo—n-
`alkanes, from which the Hildebrand parameters in Tabie 3:: were evaluated.
`The basis of the cohesion parameter approach to interactions may be stated as follows.
`A material with a high 8 value requires more energy for dispersal than is gained by mixing
`it with a material of low cohesion paramczer, so imrniscibility resuiis. On the other hand,
`two materials with similar 8 values gain sufficient energy on mutual dispersion to permit
`mixing. This concept is attractive for practical applications because it aims to predict the
`properties of a sysrem using oniy the properties of its individual components: in principie
`no information on the properties of the mixed system is required.
`It is necessary to emphasize that the Hildebrand parameter is fundamentaiiy 2 iiquid
`state property. When gases are considered (Chapter 11) they are treated as bypothezicai
`“liquid” solutes at atmospheric pressure, and substances their are solids at normal temper-
`atures arc treated as subcoolod liquids (Chapter 12). As defined here, 1-Iiidebrand parameters
`cannot be calculated directly from vaporization enthalpies or sublinialjon endialpies without
`taking into account their liquid-state basis. Lswsorfs list of "solubility parame1.e1's" of the
`eiemenLs”"“ {Table 4) is a useful set of cohesion parameters, (although they are not Hil-
`debrand parameters if they are calculated directiy from enthalpies of vaporization or sub-
`
`MYLAN PHARMS. INC. EXHIBIT 1044 PAGE 6
`
`

`
`9'
`
`mm
`fling
`
`$;£l;I
`
`25_ 5
`19.3
`202
`296
`319
`23-7
`21!
`24_]
`24-0
`414
`1-“
`38‘?
`39.3
`3:5
`16-8
`219
`392
`39_ ;
`306
`263
`22.1
`35'-7
`35_2
`37.9
`335,
`333
`310
`
`cf‘ Fmatad
`I_s1tIes was
`;ch_[o;-5.3.
`5 f0n_m_vS‘
`by mixmg
`her hand,
`to permit
`redial the
`.
`.
`pnnciple
`
`.r a liquid
`potheiical
`,1 temper
`arametcm
`_
`S wlthout
`3" Of the
`: not Ht'l-
`In 0!. Sub_
`
`‘
`
`TABLE 2
`Rounded Values of Cohesive Energies at 25°C
`
`Foflllillll
`
`Compound
`
`— 0;” may!
`
`27
`
`!
`
`C2Hn-
`C3Hs
`CaHw
`
`Csxu
`
`CGHM
`
`C73”
`
`CIHIO
`
`C;-Hzu
`C H
`[0
`21
`
`CI Ina»
`
`CIIHM
`
`gragza
`" 5°
`9:332
`I
`34
`C1133:
`C33»
`C45:
`C5143
`C_1Hm
`CaH!2
`5::.2
`u
`CI-Hm
`CJ-he
`C93“
`cu-.Hza
`CIIHZ
`Cr-2H'a7.
`C335
`C.H.
`
`C H
`3
`4
`Csflm
`C.Hu
`CsH--
`Caflne
`gtuflzu
`:1-HM
`Cnaflsz
`C-5H5
`C6H:c
`C: H:
`Csfim
`
`Elhfiflfl
`Propane
`Butam:
`
`Isobulann
`Pentane
`Isopentane
`Nenpentane
`Hcxamz
`Branched hexanes
`Heptane
`Branched heptaru-.s
`Octane
`Branched octanes
`Nflflaflfi
`Branched uonancs
`D9331}?
`Branched decames
`Ufidfiflfinc
`Branched nndecanas
`Dndccane
`2,?.,4,5,6'?Efl§3III£dIy}hepta;n¢
`
`°““°"°°“"°
`Eenmdecane
`exadecane
`Hepladecanc
`Cycicpropame
`Cy-clobutanc
`Spmopenlane
`Cyciopeamme
`Cycfoalkznes
`é-Meth3ribicyclo[3.I fljhcxane
`ycloalkanes
`Cycltyfzlkanes
`f.4—D:mctlIy2bicycio[2.2.I1hep£ane
`Cytloalkmes
`Cycloallumes
`Pennylcyclohexmw.
`Cyciehcxylcyciahexane
`I’:-opylerne
`1,2-Butadiene
`l,3—Bu1ud':cnc
`1-"We
`_
`égzme
`Alkenes
`2.3-Dimethyl-2-buteru:
`Mk:-'ncs
`1—Oc:em:
`I-Decene
`l-Dodecene
`I-Hexadecane
`Benzene
`C3-cloiacxcne
`Toluene
`Aikyibenzenes
`
`73
`133
`19.2
`I16
`243
`213
`]9_9
`293
`25_23
`342
`3o_33
`391
`33__4;
`44_0
`36_4[]
`4&9
`45_47
`5&9
`43_._52
`593
`455
`543
`68.3
`73_5
`739
`335
`15);
`2] _5
`252
`25_ 3
`2g_31
`32_4
`3z_34
`35_3g
`35.4
`42_43
`45
`51 4
`555
`33,-;
`213
`I9.G
`21.3
`
`23_25
`3112
`40-42
`333
`43;).
`§g_3
`';."}I_3
`3}_5
`31_ 1
`3515
`40_4;
`
`‘
`I
`1'
`
`i
`5
`
`I
`‘z’
`'5
`'
`'
`
`
`
`MYLAN PHARMS. INC. EXHIBIT 1044 PAGE 7
`
`

`
`
`
`.
`
`I
`
`28
`
`CRC Handbook ofSo!ub:'!:'ry Parameters and Other Cohesion Parameters
`
`TABLE 2 {continued}
`Rounded Values of Cohesive Energies at 25°C
`
`Fm1:nn.la
`
`Compound
`
`- Wk} 1110!“
`
`Cg}-In
`
`CJ-Km
`
`Cg!-I1,
`CmI*I,.
`C,,H,,
`C6F{,
`QHF,
`C51-LP,
`CJ-1,17
`C-,H3F,
`C-,1-15F,
`C7H,F
`CHE;
`C31-i,;F
`C,F,5
`C,‘-,F,,
`C,¢,F,,J
`CCL.
`CHCI,
`Cl-I;Ci-,.
`QCL
`QHCQ
`C;H2Cl;
`C,H ,Cl,.
`C,H3Cl3
`
`C,,H_,Cl,
`
`C3H,Cl,
`C,H,(,‘l
`C‘H,,Cl,
`
`C..H._,Cl
`
`C,H NC1,
`
`4-Vinyl-4-cycIohexene
`cfs. ci.9— I ,5—CycIoocladiene
`Alkylbenzcncs
`cm 5-EtbyIidenebicyclo[2.2. i}—2—heptene
`2.3-Dimel.hy}bicyc!u[2.2. I]-2-heptene
`Alkyibcnmncs
`Cyclohsxylbenzene
`Hexaflutwobenzene
`Penlafllmmbcnwtne
`Difluor0bm1?.er|es
`Flucmbenmnc
`2,3,4,5,6-Pcntafltzorotnlucnc
`('I‘riflu0romethy1)?:Icnz:nc
`4-Fluomtolucnc
`Oc£adIwa:Fl'uorau<;1ane
`I-Flunmoctaxw
`Octadecafluompropylcyclohexanc
`Ocladscafluomdecnhydronaphthaiencs
`Pediuoroz-methylpropylcyciohexmw
`Tetrachlorolrucflmtc
`Trichloroincthanc
`Dichlarumethmz
`Telzuchlamelllylene
`Ttichloroednylcne
`1,]-Dichloro-ethylene
`1.1.2.2-TeIrachlon:eI3Jane.
`1,1 . 1 -Tric!1Icm.Ie£hane
`i , I ,2-Tuiclfioroetharin
`{,1—Dichl~ome£hane
`X.2—Dichlome:hane
`i,3—Did'I1-ctmpmpane
`1-Chloropmpane
`1.2-Dichlvomhubane
`I .4—DicII lorubulane
`I-Chlorobulann
`Isuhulyl chloride
`sec-Bury! chloride, 2-cl'I!0I'obutanc
`:err—Eu:yl chloride
`1,2»-Dichlotnzzpentanc
`1,5-Dichlorcpcntwm-.
`Chloropcntanes
`Chiombenzene
`I ,2—D§ch}o1'o21exsne
`I-Chlarohcx an:
`I—ChIomhepta.ne
`I-Chlomoctanc
`I-
`
`CSH , [C1
`C,,H5Cl
`C51-l,,C12
`C5}! “C1
`C711, ,Cl
`C.H,,Cl
`C,2H,_.,CI
`C19!-Ijfil
`CHBI, W c
`CH,Br-_.
`Dibromomethane
`CH,B:
`Bromomethane
`C,H.Br,
`1,2.—l)iln-onmoezhanc
`C;H,Br
`Eromaerhanc
`C_,,H,Br
`Allyl bromide
`C,H,B I:
`1.2-Dibmmopmpane
`l,3—Dib:0m0pmpan:
`
`37.1
`40.9
`43—48
`4 l .7
`39.7
`45—4-‘J
`57.5
`33 .3
`33.9
`32-34
`32.2
`38.7
`35.2
`310
`38.7
`47.2
`40.6
`43
`44.3
`30. 1
`28.9
`26.5
`312
`32. I
`24.3
`43 .3
`30.1
`37.8
`28.3
`32.7
`38.3
`26. I
`3?. I
`43 .9
`3] .2
`29.3
`29.2
`26.7
`41.4
`«$3.2
`34-36
`38.5
`45.1‘
`40.4
`45.2
`49.9
`68.7
`
`43.6
`34.6
`220.8
`39.3
`15.3
`30.4
`39.2
`45.0
`
`MYLAN PHARMS. INC. EXHIBIT 1044 PAGE 8
`
`

`
`TABLE 2 (continued)
`Rounded Values of Cohesive Energies at 25°C
`
`Fonnuls
`
`Cmnpoumi
`
`— Uffl um! "'
`
`29
`
`C,H,Br
`C,,H,Br3
`
`C.H,Br
`C,H,,Br
`C5H,Br
`C5H._.r
`C,H,,Br
`C,,]H,,Br
`C.,H;,Br
`C,5H,,H:'
`C1}-1,!
`C,H.,I
`C,H.,l
`C,.H,,I
`C.H,,l
`C,Br,Cl.F,
`C,Br,F4
`C,CI,F,
`CAI-£BzC1F3
`QH.,BrCI
`c,c:,F.
`(‘.,H2Ci,F3
`C3H,Cl,F,
`C,H,BrC§
`CECJP,
`CI-I,N
`c,H,N
`C,_H,N'2
`(.‘,H,,N
`
`C,H,,_.N,
`C.H,.N
`C,H,3N
`C5}-LN
`CEH,,N
`C,H,,N
`C,H,N
`C,H,,N
`C_,H,,N
`Cal-l,,N
`C,H,,N
`Cm,
`C,H,N
`C,.H,N
`CJ-LN
`CJ-I.,N
`C_,H,N
`
`C,H,N
`C,H,N
`C,;H.,N
`C6}-l',,N
`
`Brumopropanes
`I ,4—Dibrc:nobutane
`I ,2-Dibromo-2-melhylpropane
`Alkyl bromides
`I-Bmmopcntanc
`Bromnbenzcne
`1-Bromchexanc
`.1-Bromoheptunc
`l—Bromoc-ctane
`I-Bromododacaxre
`I—BIwu
`Iodoelhzme
`Iodrrpmpanes
`Iodobutanes
`l-Iodopemanc
`I-lodahexane
`l.2-Dibrnmocfzloronifluoroethanc
`l,2—DibmmoteIrafluome2hane
`Trichloronifluomudisnes
`Bromoohlmmzifluomcahanes
`I -Bmmo~2»chloroct21a.nc
`3,2-Dichlorohexafluorupropanc
`3 ,1,I-Tzichioro-3,3,3—triflnoro'prorpauc
`1,1-Dich}am—3,3,3-Irifluomplnfhmic
`l—Br0m0-3—c.IiIm‘0pr0pa.tIc
`Chis:-opentafluombcazene
`Mclhylamine
`Dimethyiaminc
`{.2- , erilylcna dfianljne
`Propylamine
`Isnpropylaminc
`Trimeihylaminc
`I,3—Propa.11odia.n1ine.
`N-Methy1—I,2-ezbanediarnine
`Butylamines
`Prcpylamines
`Aniline
`Cyclohcxyiamine
`Hexyiamines
`Benzylaminc
`Heplylsmines
`MN-Dinaethylanilinc
`Octyiaminas
`'I'ripropy]a.mine
`Ezhanedinitrilc
`Ethsncniuilc, aor.-.tonitri.Ic
`Propnncnilrilc, prapionatrilc
`Butcnenitriles, aliyl cyanide
`Cyclapropanetzirbanitrilc
`Butanenitrires
`Pcmeneniu-iles
`Cyclobutanccarbonitrile
`Pcmanenizrizcs
`1—Cyc1op:m£.nuca:bon.itrile
`Cyclapcntanecaxboniflile
`Hexanmumic. caprmijlrile
`
`28——3{I
`50.6
`40.9
`30-34
`38.8
`42.1
`43.4
`48.1
`53.3
`72.3
`91.9
`29.6
`32- 34
`31-38
`42.8
`47.3
`32.6
`26.]
`26
`27—28
`35. 7
`24.3
`34.3
`3!.7
`41.6
`38.6
`21.4
`23.0
`42.5
`29.0
`26.2
`$9.7
`47.?
`42.?
`29——33
`31-33
`53.4
`41.2
`32—43
`57.7
`49-A13
`56.4
`4?——50
`43.7
`13.4
`39.9
`33.7
`3?—38
`39.5
`35——37
`41-43
`41.9
`35--41
`42.5
`4] .0
`45.4
`
`.
`
`F
`‘
`|
`
`'
`‘
`
`}
`
`l
`.
`|
`I
`
`|
`
`I
`l
`
`I
`'
`
`.
`
`
`
`MYLAN PHARMS. INC. EXHIBIT 1044 PAGE 9
`
`

`
`30
`
`CRC Handbook of Solubiiity Parameters and Other Cohesion Parameters
`
`TABLE 2 (continued)
`Rounded Values of Cohesive Energies at 25°C
`
`Fornmla
`
`Compound
`
`- U/kJ mol"
`
`C,H,N
`C,H.,N
`C,H,5N
`C..,H,,N
`CHHHN
`C,,I-IMN
`Cp4H:1N
`C.H.,N3
`
`C‘H.,N
`C,H,N
`C5H,N
`(L,H.,N
`C,H, ,N
`C,H,,-N,
`CHGNE
`C;H,,N1
`C,H,1N,
`C€H,,,N,_
`
`(3,!-i,,N,
`
`C,,H,,N1
`C,,_I-I,,N;
`C,H,O
`C4!-I,.,0
`C,,H,,,O1
`C,I-[R0
`
`C5!-1,31},
`
`C6H,2O
`QHNO
`
`C5!-I,,,O,
`
`C,H,,O,
`C;H,,O
`C-,H,,()
`C7}-I",-O,
`CTHHO‘
`C,.H.,,0
`C;H,gCI
`C,H,,O,
`C,H,3O,
`C,H,,,()
`C,,I-13,0,
`C,,,HnO
`C,9H23U,
`CHI-1,40
`C,;HQ,.,O
`CH.0
`CEHGO
`C3H5O
`
`1-Cyclohexenecazboraitrile
`Cyciohexanecarbonitrilc
`Octartenitrile
`Dccancniirilc
`Undamnmfihile
`Dodecanenilriie
`Tetradecanenitrile
`Pyddazine
`Pyrimidine
`Pym-ole
`Pyrrolidine
`Pyridine
`Mcd1y!pyrid.i:m:9. pioolint:
`Dinwtlxykpyridines
`Trime Ihylpyridines
`3.3,6,6—Te-i:ameIhyl—3,4,5,6—tetrahydrapyridazinc
`Methylhyclrazine
`Dirncmylhym-nines
`1-{Me:hy1azo)bmane
`Azopmpauc
`2-(Isopropyla.zu}pmpa.n1u
`Azobutane
`2-{terr—BIIty]azo)—2—mcihyIpn'}pane
`2-02-n—But3.Ilam)—2,4,4-lrirnethylpentane
`2,2’-Am-{2,4.4-uimethylpentmej
`Di-methyl e-the:
`Ethets
`1 ,2-Dimcdloxyclhanc
`Bury] methyl etbexs
`Ethyl pmpy} etlzers
`1-Elbuxy-Zmndnxycfliane
`Diethoxymeihane
`Busy] vinyl ether:
`Memy! pemyl ethezs
`Bntyl ethyl eihers
`Dipmpyl ether:
`2-Methoxy-1-pmpoxyetham
`Dieflxoxyethane
`Bis(e!hoxymcd1yI)ethcr
`Mclhyl phcnyl ether
`Ethers
`Dierhexs
`3,5,':',9—'l‘en'aoxoLmdecane
`Ethyl phenyl ether
`Ethers
`Diethers
`Dieflaylene glycol dieihyl ether
`Ethers
`I -Butnxy-2-pmgnxyelhane
`Ethers
`1,2-Dibuioxyezhane
`Emers
`Ethers
`Math anal
`Ethanol
`1-Propane]
`2-Pmpanol
`
`51.1
`49.4
`54.3
`64.4
`68.‘?
`73.6
`82.3
`51.0
`47.3
`42.9
`35 .6
`37.?
`40—-12
`43—48
`43
`4'.-‘.6
`38.0
`33-37
`33 .9
`37.4
`33.4
`46.8
`36.6
`5I . I
`64.1
`16.8
`25
`34.0
`28—3B
`28-29
`37.4
`33.3
`32-34
`33-34
`3]-—3-4
`3{l—33
`41 .2
`40.8
`42.2
`44.4
`3E—40
`43-45
`5 1| .2
`48.6
`35-44
`43-49
`55.9
`42—50
`52.2
`48-55
`56.3
`58—6TJ
`62--63
`35 .4
`40.0
`45 .0
`43.0
`
`MYLAN PHARMS. INC. EXHIBIT 1044 PAGE 10
`
`

`
` 4 If
`
`3!
`
`TABLE 2 (continued)
`Rounded Vaines of Cohesive Energies at 25°C
`
`Formula
`
`Campound
`
`- UHIJ mo!“
`
`C.,I-L90
`
`C,H .90
`c,H,,o
`
`C6!-[[20
`C31-l,_,0
`
`C,H,,0
`C,H,,;.O
`C,I-1,30
`C,H,.-,0
`Cw!-I;,O
`C,,H,.O
`C,‘H,D0
`C1H,.O
`C,H.,O
`
`C,H,,O
`C,I-I30
`
`C,H,U3
`C5]-1,00
`C,H“,0
`C,H,,O
`C,H,.,O
`C-,H,..O
`Ca]-1,50
`C9H§..O
`C,H,5O
`C9!-1,30
`Cml-l,€0
`C,,,H,.0,
`Cpgliggo
`C. ,H,,O,
`C.,H,,O
`
`CHI-I-5,0
`CH,,O,
`QILO2
`C3H5O=
`c.H,.0,
`C',I-LO,
`C,I-I502
`C,H,,O,_
`
`C,H,,U,
`C,H,9O,
`C,-H.,.O,
`
`CISHHO2
`C,H,,O,
`C,HaOz
`C,H,,.O.
`Caflmoz
`C-9H M0,,
`C.,H,,.0-_,_
`C,.,.'H,,O.
`
`I-Butane]
`
`Other butanols
`Cyciepentanol
`I-Penim-D]
`Other pentanols
`Cyclohexanol
`1-Hexanol
`Othex hexxnois
`I-Hepzanol
`Dimcthylphenois
`I-Octane!
`I—N0m:.noI
`I-Deeamol
`l—Dodec:mo!
`l—'l'eIradeca1Iol
`Etha:-ml, am-etaldehyde
`Ptopanal
`2-Propanone, acetone
`2-Bntsnone. methyl ethyl kctone
`Cyciupentumne
`Cyclopmpyi methyl ketone
`2,4—Pentmedione
`Pentanones
`Cyclohexamsne
`Hexanones
`Dicyciepmpyl kelone
`Heptunoncs
`2,2.é—Tn'mel.hyI—3—penI'.anun.e
`2—Hexahydm.inda:r1one
`D‘Ln3eLhyl—3,S—heptanediones
`Ncnanones
`trans-8-Methyl-2-hexahydznindnmxae
`2,2,6-'{'I1methyI—3,5-heptaliedione
`2,2,5,5-Tetramednyi-3-hcxanone
`2.2,6,6—Tetra:nethyi-3,5-heptanedione
`Undecanmles
`
`2-Dodecanone
`Fumxic acid
`Acetic acid
`Prnpkrnic acid
`Bulyric acids
`Methyl formate
`Esters
`Esters
`
`Methyl cycloprogyanecaliaoxylate
`Esters
`Methyl cyclobutanecmboxyiaze
`Ethylene glycol diaoezate
`E3973
`Esters
`Methyl benzrmte
`Elhyierne giytol dipropanuate
`E-51°75
`Trixcetin
`Methyl octanoate
`Ethylene glycol dibutanoete
`
`49.9
`
`44—-48
`55.2
`54.5
`48-53
`59.5
`59.1
`52-58
`64.3
`62—80
`68.5
`':‘4.4
`79-0
`89.5
`99.7
`23.7‘
`27.5
`28.8
`32.4
`40.3
`37.0
`40
`34—36
`43.4
`36—41
`5 L2
`39—45
`40. 3
`54--SS
`53.6
`43———-54
`55. B
`55.3
`46,3
`5'3‘. 1
`5{)_{';5
`
`69.4
`43.8
`49.1
`52.5
`51-55
`26
`30
`33—35
`
`333
`35.— --37
`42,3
`59.0
`36-41
`39.445
`53,[
`55,]
`49
`83. 3
`519
`?D_7
`
`I.
`
`I
`
`'
`'
`
`1
`l
`
`'3
`
`1
`
`'
`
`I
`l
`
`'
`
`
`
`MYLAN PHARMS. INC. EXHIBIT 1044 PAGE 11
`
`

`
`1
`
`'
`
`|
`1'
`I
`
`32
`
`C-RC Handbook of Solabfkry Parameters and Other Cohesion Parameters
`
`TABLE 2 (continued)
`Rounded Values of Cohesive Energies at 25°C
`
`Formula
`
`Compound
`
`- UHIJ me!“
`
`cwnmo.
`C, ,i-I220,
`C,,H,..O,
`C,-,H-M0,
`C,,H.z5O;.
`C,..l-I250,
`C,,I-I505
`C,_,H_.,¢,O,
`Cm}-I320,
`c.H.o
`C,I-L02
`C,}L,0
`
`CJ-1,0
`C..H.0,
`(3.!-1,0
`C_.H,.0:
`
`C5H,.,0
`
`‘,1-L00,
`C,,l-1,604
`Cml-IMO,
`C31-1,0,
`C.l-I190;
`C,-LL90,
`
`C,H,,01
`C.5H,,O,
`
`C,,H,..0,
`C,H,,,O,
`CEHNO3
`CS;
`(3,!-{,3
`C,I-I581
`C,l-1,8
`C,H,,,S
`
`C41-INS,
`C5!-1,15
`C51-I,,S,
`C,H,,,S
`CJINS,
`
`C,.!-LES
`C,H,.S.,
`C386.‘-3
`C2358,
`C,H,S
`C,H,S
`CJ-INS
`C41-INS,
`C.,H,2S
`C,-HHS,
`
`Methyl mmanoatc
`Methyl cleacartoate
`Tripmpionin
`Methyl uudecanoatc
`Methyl dodocannate
`Methyl tridecaneete
`Glcycral tribal}-rate
`Methyl tetradecanoatc
`Methyl pemaclcczneate
`Oxirane. ethylene oxide
`B-Propiolactone
`Mctlwlcxirane. propylene oxide
`Oxctame. trimethylene oxide
`Fman
`Diketcne
`Tecrahydmpyran
`1.3-Dionne
`1,4-Dionne
`3,3-Dimethyloxetane
`Tc
`1,3.6—Trioxacycloocta.ne
`1,4,7,i0-Tetraoxacyclododccanc
`:,4,7,I0. 13-Fentwxacyclopeniudecane
`2-Methoxycthanol, nwlhyi cellosolvc”
`2-Ethoxycthanol, oellosolve
`Dicthy! carbonate
`2-Memoxyethyl acexate methyl cellosolvl: acetate
`Prepoxyethanois
`2-Ethoxyethyl acetate cellosolvc acetate
`Ethoxymethyl propanoate
`2-Butoxyethanoi, butyl celloeclve
`2-Prcpoxyethyl acetate
`2-Butoxyelhyl acetate, bmyl oellusolve acetate
`Carbon disnlfide
`Dimxzthyl sulfide
`Dimezhyl disulfide
`Ethyl methyl sulfide
`Methyl propyi sulfide
`laopropyl methyl sulfide
`Diemyl sulfide
`Diethyl disufide
`Diallcyl sulfides
`‘Bis{e£hylthio)mefimnc
`Dialkyl sulfides
`l ,2-3i.s(elhy1thio}ethanc
`Dipropyl disulfide
`Dialkyl sulfides
`Dialicyl disulfides
`Eahanezhiol, ethyl mcmpuan
`I .2-Ethaneditlubl
`Plvpanelhiols
`l ,3—Propanedizhiol
`I .4~Rntaned.ithi0I
`Cyclupemanethiol
`Pemaneihiois
`1,5-Pemunedilhial
`
`59.5
`64. 3
`88.9
`69.0
`74 .7
`80.2
`104.6
`84.5
`91.0
`23.0
`44.6
`25.8
`27.?
`25.2
`40.4
`29-7
`36.7
`36.2
`31 .6
`32.2
`46.3
`63.2
`77.]
`42.7
`45.8
`41.1
`47.8
`48--50
`50.2
`47.4
`54.1
`53.1
`57.1
`25.2
`26.5
`35.4
`29.5
`33.8
`31.8
`33.4
`42.7
`33-38
`48.3
`37-«-43
`57.0
`56.7
`41-56
`52-60
`5.1
`42.2
`2‘?—-30
`47 .2
`29-34
`39.0
`33—39
`56.8
`
`MYLAN PHARMS. INC. EXHIBIT 1044 PAGE 12
`
`

`
`-w
`
`33
`
`TABLE 2 {continued}
`Rounded Values of Cohesive Energies at 25°C
`
`Fonmlla
`
`Compound
`
`— U1}! mo!“
`
`C,.,H,S
`C5!-3,,S
`C,,,H2,S
`C,H_,S
`CJLS
`C.,H,S
`C,H3S
`C51-[£3
`C5}-[.03
`CN,0,
`CH,N0
`CH, N02
`CzH,NO
`C,H,N0
`
`C.,H,N0
`
`C_,H, ,N0
`
`?,H,N01
`C,H.,NO,
`QH,,NO
`
`Cfii-I,‘ N10
`C,,H,,N,0
`C,.,H,, NO,
`C.H,CIS
`C,H,aOS
`
`C,,H,,DS
`
`C,H,N'S
`
`1
`—-
`
`Benzenelhiol
`Cyclollexametlziol
`I-Decanetlaiol
`Thiecyclobmane
`Thiophene
`Dihydrolhiophenes
`'!‘hiacycIopentane
`Methylthiophenes
`Thiecyclohexane
`Tetranitrorncflaane
`Fommmide
`Nirmmethane
`N-Merhylforznamidc
`Mfilhylformamide
`N,N-Dirnethylfmmamide
`N-Elhyiacetamide
`N,N—Dime1hy}aceIamide
`N—Metbylpmp:'una.mide
`N.N—DiethyIfonnamr'de
`N-Progyylacelazrridc
`N-Isoprapylacetsrnidc
`N-Mefllylisohutymmide
`Nitrobenzene
`Tfiaoctanfide
`N—Buly§accta.rnide
`N,N-Dielhylecctamide
`N-Nilrosodipmpylamine
`N-Nitroso-di—z¢-rt-buylamine
`N.N-Diacetylaniline
`Ethyl thioiethzooate
`Propyl ihiolelhanoare
`I-Methylezhyl Ihioleihanoate
`Bury! Ihiolelhanoate
`l,I—Di1neIhyle:l3y] Lhiolethamale
`4-Methylthiazole
`Halogen-subsfiluied eflacrs
`Halogen-subsrim-led esters
`Halogen-substituted diaries
`
`45. I
`42.1
`63.0
`33.5
`32.3
`33-38
`37.0
`36—3'7
`40. I
`47.5
`57.?
`35.9
`53. 7
`56.0
`44.4
`I52.-Ii
`47.8
`62.4
`47.8
`67.3
`63 .9
`64.6
`52.5
`519
`72.5
`51.6
`49.2
`43.5
`68. l
`37.5
`41.6
`39.8
`45.6
`40.5
`41.4
`3l]—52
`44—4-9
`23—35
`
`Selecled am‘ adapted from Majcr. V. and Svoboda. V., Emhaipy of Vrgporization :9’
`Organic Compoumir, IUPAC Chemical Data Series No. 32. Biaclrweli‘. Oxford. 1985.
`
`2.3 THERMODYNANIIC EQUATION OF STATE
`
`Any expression linking the state properties of a material is known as an “equation of
`state”. The most filndamental equation of state is the thermodynamic equation of stare,
`which follows from basic thermodynamic relationships and involves pressure p, molar vol-
`ume v, absolute temperature T, and the molar internal energy U:
`
`
`
`MYLAN PHARMS. INC. EXHIBIT 1044 PAGE 13
`
`

`
`34
`
`CRC Handbook cfSo£‘ub:'my Parameters and Umer LOHESIUH rarwneuen
`
`TABLE 3
`Selecled Values of Hildebrand Parameters at 25°C
`
`Formula
`
`Substance
`
`Wear‘ mill"
`
`,6, H or
`A. H
`H moi"
`
`BIMPI“
`
`Bromine
`Iodine
`Sulfur
`Phosphorus
`
`Elements
`
`Tetrahafldes
`
`Tetrachlmomclhanr, carbon Letrachioridc
`Silicon tetrachloride. tetrach1orosi1ane
`Silicon tctrabrornidc, tctrabrornosilanc
`Gcnmninm tcuachloridc
`Stannic chloride
`Stannic iodide
`
`51
`59
`135
`70
`
`97
`115
`I27
`115
`118
`15]
`
`Br,
`I,
`8,.
`13.,
`
`CC1,
`SiCL
`SiB:,
`GOCL.
`SIJCI.
`Sn].
`
`other Inorganic -mmpomsds
`
`090.,
`MOP,
`WP,
`UF5
`Si(Cl-I3)
`
`Osmium tetroxide
`Molybdenum hcxafiuoridc
`Tirngstcn hexafluoride
`Uranium hsmfluofide
`Telramethylsilane, silicon telramethyl
`
`58
`84
`88
`96
`136
`
`Aliphatic Hydmcarbons
`
`C_.,]-112
`
`C61-1,.
`C,H,,,
`C311“.
`
`C1,,-H3.
`C,I-1,9
`C51-1,,
`QR,‘
`CG]-In
`C,,I-1,,
`C51-1,,,
`
`Cfim
`0,1-1,,
`C31-{,0
`
`C,,H,,
`
`C31-1,
`C NH,
`C1,H,,,
`
`Pcrztane
`Isopcntane, 2-mczhyltmtanc
`Neopeatane, 2,2—dimI:2hyI‘pnopane
`Hexana
`Hepume
`Octane
`Isooctane. 2.2.4-Irimeihylpemane
`Hcxadocanc
`Cyclopemmc
`Cyciohexane
`Methylcycinhgxanc
`1-Haxenc
`1-Octane
`1,5-Hcxadicnc
`
`116
`117
`122
`132
`148
`164
`I66
`294
`95
`109
`128
`I26
`158
`118
`
`Aromatic Hydrocarbons
`
`Benzene
`Toluene, methylbenzene
`Etiiylbcnzznc
`o—Xy1cue, 1,2-djxmthyibanzcne
`m—Xy1ene. 1,3-dimethylbenzgem
`p—Xy1e-ne,
`i,4—dim:-Jhyibcnmnc
`Propylbcnzem-.
`Mesizylene, 1.3.5-trimethylbenzene
`Stymnc, cflxenylbcmsnc
`Naphthalene
`Anthracene
`Phenamhnene
`
`89
`10?
`123
`12.1
`123
`124
`1.40
`140
`116
`123
`(1513)
`158
`
`36.?
`--
`--
`
`52.7
`
`32.8
`30.!
`43.4
`33.8
`40.0
`82.1
`
`41.0
`26.6
`26.2
`30
`24.3
`
`26.3
`25.2
`22.4
`31."!
`36.6
`41.5
`35.1
`81. I
`28.7
`33.1
`35.4
`30.?
`40.6
`31.3
`
`33.9
`38.0
`42.3
`43.4
`42.7
`42.4
`46.2
`47.5
`43.9
`
`23.5
`28.3
`25.4
`26.8
`
`17.6
`iii
`18.0
`16.6
`17.8
`23.9
`
`25.3
`17.0
`16.4
`18.2
`12.?
`
`14.5
`13.9
`22.7
`14.9
`15.1
`13.3
`14.!
`16.4
`16.6
`16.8
`16.0
`14.9
`15.5
`15.8
`
`13.8
`18.2
`18.0
`18.4
`18.0
`18.0
`17.6
`18.0
`19.0
`20.3
`20.3
`20,0
`
`MYLAN PHARMS. INC. EXHIBIT 1044 PAGE 14
`
`

`
`waters
`
`BIMPR”
`
`33-5
`28.8
`25.4
`25.3
`
`17.6
`15. 5
`13.0
`16.6
`17.8
`23.9
`
`25.3
`17.0
`16.5
`18.2
`12.7
`
`14.5
`13.9
`12.7
`14.9
`15. I
`15.3
`14.1
`16.4-
`16.6
`16.8
`16.0
`14.9
`15.5
`15.3
`
`8.8
`:3 2
`18.0
`1114
`18.0
`13-:
`30
`19-0
`
`20.3
`20.3
`29-0
`
`1
`1.
`
`TABLE 3 (continued)
`Selected Values of Hildebrand Parameters at 25°C
`
`9
`Formula
`
`Substance
`
`V/cur‘ ma!"
`
`,4.‘ H or
`111- H
`RJ moi"
`
`fi."MPa”‘
`
`Fluorncarbtms
`
`35
`
`C5F14
`C.1=,,
`C,Fu
`c,1=,_,
`
`Perflueroliexane
`Perfluorolieptane
`Perfluorocyciohexune
`Pc;fluom(methy1eycIo-hexane)
`
`Other Fiunroclxunicxls
`
`(CJ3‘,),N
`C.Cl.,F6
`C,.c:1,F.,
`c,c1,1=.
`C,F._,H
`
`Perflnomfiburyiamine
`Dichlemhexafiuawcyclobumnc
`2,2,3-Tficblmnheptafluomblnane
`1,1,2-T1‘i1:l1Jr1ro—I ,2,2,—1n'11uo1-oe111ane
`Penzadecafluomheptane
`
`205
`226
`170
`195
`
`360
`I42
`165
`1213
`215
`
`Other Aliphatic Halogen Compounds
`
`CI-I,Cl2
`CHCI,
`CC3.
`(111131,
`CH}
`Cl-I21;
`C,H,Cl
`C11-1,81
`C,H,I
`Cal-LC],
`C,H.Brz
`C._.H,Cl,
`C21-IZCI,
`C,1:1.
`
`CS;
`C31-1,02
`C.1-1,50
`
`Dichlororrtethanc, methylene diclllcridc
`Trichluromezbme, chloroform
`Tczracblormnellmne, carbon tetmchlorh:
`Tribmmamethane, bmmofonn
`Iodomclhsne, metlzy1 iodide
`Diiodomcthane, rrletbylene diiodide
`(Zhioroethanc, elhyl chloride
`Bmmoethane, ethyl bromide
`Iode1hanc,ethyl iodide
`!,2-Dicblomethane, ethylene dichloride
`1,1-Dicblamerhane, ethyiidene didlloride
`1,2-Dibmmuethane. ethylene dibmmide
`l,I.I—T1'k:hloroetbane
`r.':'s—l ,2—Dic!'1lom-ethylene
`:mm—1,2~Dichl0roetbylene
`Tetrasbloroetbylcne
`
`64
`81
`9')‘
`88
`63
`31
`74
`75
`81
`T9
`85
`90
`100
`76
`78
`103
`Other Aliphatic Compounds
`61
`89
`105
`
`Carbon Lfisultide
`Dimetlzoxymeihane, merbylal
`Dielhyl ether
`
`32.4
`36.4
`28.9
`33. 1
`
`54.4
`—
`35,6
`27.5
`37.7
`
`28.6
`31.0
`32.3
`43.1
`28.0
`.
`-
`23.8
`27.2
`32.2
`34.?
`32.2
`41.4
`32.6
`28.9
`28.5
`39. 7
`
`28.0
`2'16
`26.6
`
`l2.1
`12.3
`12.5
`12.5
`
`12.7
`14.5
`14.1
`14.5
`12.9
`
`29.0
`18.8
`17.6
`21.5
`20.3
`24.1
`17.0
`13.2
`19.2
`29.3
`18.6
`20.9
`17.4
`18.1‘:
`18.4
`19.0
`
`29.5
`15.8
`15.1
`
`Adapted from Hiidebrand, J. H., Pnmsnitz, J. M., 311:! Scott, R. L, Regzduran.a‘Re(a:ed Solutions. van NosIran1:T-
`Reinhold, Princewn, NJ, 1970.
`
`ravzam = Hapram -- p
`_
`_
`_
`_
`Many Iiqmds have values of (ap;aT)V and (awavyr winch are f1.'mct1ons only of the molar
`volume within experimental precision over reasonably wide temperature and pressure
`ranges. ""5 Because they show this simple behavior, these functions have been given special
`names and symbols. The internal pressure is
`
`1'1 E (3Ul3V)1-
`and the isochoric (constant volume) thermal pressure cowicienr is
`
`(33)
`
`
`
`MYLAN PHARMS. INC. EXHIBIT 1044 PAGE 15
`
`

`
`
`
`TABLE 3a
`Molar Volum and Hildebrand Parameters
`of Dichloro-Substituted n-Alkanes at 25°C
`
`Went’ moi"
`
`&.~'MPa""
`
`I.I—Dichlor0ethane
`1,1-oicmompa-opane
`I, l —Dichlorol:Iute.nc
`2,1—Dichl.o1!:IpenIar1e
`l,l-Dichlorohexane
`1,1-Diclilomheptnne
`1.1-Dichlorooctane
`1,1-Dichlorononane
`I, l—DicIIIoz‘ol.itIdecane
`1,2- e
`I ,2—Dichlo:nopropm1e
`1,2-Dichlorolnuleiic
`1.2-Dichlompeatarte
`1,2-Dichlomhcxane
`1,2-Di e
`I ,2-Dichlorooclztne
`1.2—Dichlorooonane
`2,2-Dichloralmdecane
`l,3—Dichloropmpane
`1,4-Dichlorobutmie
`[,5-Dichloropemane
`1,6-Dichlmohcxane
`l,'l—Dichloroheptane
`I ,S—[}ich1o:ooclaa1e
`1,10-Dichlorcdecanc
`2,2-Dichloropropeuze
`
`84.8
`1os.5
`13.6.9
`233.8
`I503
`157.3
`183.6
`199.2
`233.2
`79.4
`98.2
`I 14.3
`131.2
`148.1
`154.4
`181.2
`197.9
`232.0
`95.8
`112.]
`I283
`145.9
`162.6
`179.5
`213.2
`104.2
`
`I83
`:s.o
`118
`17.9
`17.8
`17.3
`l7.8
`17.7
`['16
`20.3
`38.5
`18.0
`17.8
`116
`17.3
`17.8
`17.7
`17.6
`29.0
`19.8
`19.4
`19.7
`19.6
`19.6
`19.4
`16.9
`
`Thus, Equation 7 can be written
`
`B E (3.9/67%
`
`'11 = 43 ~ :2
`
`(93)
`
`(Sb)
`
`The thermal pressure co-efficient B is related to the isothermal compressibility K and the
`thermal expansion coefficient or by
`
`and from Equation 7, neglecting p, which is usually much smaller than the other term,
`
`I3 -— can
`
`11 = TB = ram
`
`(9b)
`
`(10)
`
`The internal pressure results from the forces of attraction between molecules in condensed
`phases exceeding the forces of repulsion, and although there is obviously a. close connection
`between internal pressure and cohesive pressure.
`they are not equivalent:
`the cohesive
`pressure c is a measure of the total molecular cohesion per unit volume {an integral quantity),
`while the internal pressure 17 is the instantaneous isothermal volume derivative of the internal
`energy (a differential quantity}. The expression
`
`11'
`
`-— no
`
`(11)
`
`
`
`MYLAN PHARMS. INC. EXHIBIT 1044 PAGE 16
`
`

`
`asters
`
`37
`
`Cohesion Parameters and Atomic Volumes of the Elements
`
`TABLE 4
`
`Element
`
`Atomic
`numhx
`
`Atomic volume
`cm’ |nol'1
`
`{(A3 — .RT).’V]'*‘*
`MP3“
`
`rfg
`
`Actininm
`Aluminum
`Antimony
`Argon
`Arsenic
`Asmtine
`Barium
`Bery1’i'i1.:m
`Bistnuth
`Boron
`Brornisse
`Cadmium
`Calcium
`Carbon
`Cerium
`Cesium
`Chlonlge
`Chmmrum
`Cuban
`Copper _
`Dynproslum
`Erbium
`Eumpitlm
`Fiuorhae
`Framrium
`Gadolinium
`Gallium
`
`16
`Hafnium
`Helium
`Holmium
`Hydrogen
`Indian:
`I‘’,‘“_“‘’
`lmimm
`Iron
`Krypton
`Lamhanum
`Lead
`
`Magneszum
`Manganese
`Mercury
`M0lybde_num
`Ilgeodynnlum
`can
`Nickel
`Niobium
`Niuggcn
`Osnmum
`0xyge_n
`Palladium
`Fhosphorus
`
`39
`13
`51
`18
`33
`85
`56
`4
`83
`5
`35
`48
`20
`6
`58
`55
`::
`2?
`2?
`66
`68
`63
`9
`B?
`64
`31
`32
`79
`72
`2
`6?
`1
`49
`53
`77
`26
`36
`57
`32
`3
`71
`12
`25
`30
`42
`69
`10
`28
`41
`7
`76
`8
`46
`I5
`
`22.6
`I0
`18.2
`23.9
`13.:
`-
`39.2
`4.4
`21.3
`4.7
`(255)
`13.0
`26.0
`5.3
`20.7
`70.1
`(19.3)
`7.2
`6.".-'
`7.1
`19.0
`13.3
`29.0
`(I03)
`73.9
`20.0
`11.8
`13.6
`10.2
`13.6
`19,5
`13.8
`(6.7)
`15.7
`<25-?J
`8.5
`7.1
`32.0
`22.4
`18.3
`13.0
`I128
`14.0
`7.4
`14.8
`9.4
`20.6
`16.3
`5.5
`10.8
`(1 L4)
`8.4
`(8.5)
`8.9
`I63
`
`:39
`180
`119
`15
`149
`n
`57
`258
`99
`346
`5,5
`93
`33
`366
`141
`34
`79
`235
`253
`219
`121
`127
`78
`is
`32
`131
`:52
`355
`190
`227
`2_2
`125
`254
`:24
`64
`279
`243
`17
`138
`[(34
`112
`153
`103
`I96
`64
`255
`124
`I 1
`25