PHYSICAL PROPERTIES OF CHEMICAL COMPOUNDS

A systematic tabular presentation of accurate data on the physical properties of 511 organic cyclic compounds compiled by R. R. Dreisbach of the Dow Chemical Co. These comprehensive and basic data were determined for specially prepared, high purity compounds. In addition to the precisely measured properties the author has calculated new values for many constants based upon his new experimental values.

Number f i f t e e n o f t h e Advances in C h e m i s t r y S e r i e s E d i t e d b y t h e s ta f f o f Industrial and Engineering Chemistry

Publ ished June 1955 by A M E R I C A N CHEMICAL SOCIETY

1155 Sixteenth Street, N.W. Washington, D. C.

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PHYSICAL PROPERTIES OF CHEMICAL COMPOUNDS

A systematic tabular presentation of accurate data on the physical properties of 511 organic cyclic compounds compiled by R. R. Dreisbach of the Dow Chemical Co. These comprehensive and basic data were determined for specially prepared, high purity compounds. In addition to the precisely measured properties the author has calculated new values for many constants based upon his new experimental values.

R. PEPINSKY THE GROTH INSTITUT~ COLL~GE OF CHEMISTRY AND PHYSICS THE: PENNSYLVANIA STATE UNIVERSITY

UNIVERSITY PARr.. PA . U. S. A.

Number fifteen of the Advances in Chemistry Series Edited by the staff of Industrial and Engineering Chemistry

Published June 1955 by AMERICAN CHEMICAL SOCIETY

1155 Sixteenth Street, N.W. Washington, D. C.

Copyright 1955 by AMERICAN CHEMICAL SOCIETY

All Rights Reserved

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Copyright 1955 by AIIERlcAN CHEMICAL SoCIETY

AU Rightll Ruervl

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Physical Properties Of Chemical Compounds

R. R. Dreisbach The Dow Chemical Co., Midland, Mich.

Definition of the Symbols and Parameters Used, with the Methods of Calculating the Parameters

Mol. % Pur.: Mole % purity by weight. F.P.! Freezing point, C. F.P. 100%: Freezing point curve extrapolated to 100% purity. B.P. 760 mm., 100 mm., etc.: Boiling points at these pressures, C. Pn : Pressures at 25 C., in mm. P.: Pressure corresponding to temperature t. in mm. d20, etc.: Density at 20 C., etc., g./ml. a, b: Constants of Law of Rectilinear Diameters, dv + dL = a + bt

d. = density of the vapor, g./ml.; dL = density of the liquid, g./ml. ng', etc.: Refractive index for the sodium line at 20 C., etc. "C": Constant of the Eykman equation, (nfi - 1)/(no + 0.4) X l/d = "c" MR (obs.): Molal refraction (obs.) = (nfi - l)/(nfi + 2) X M/d = MR at 20 C.

(M = mol. wt.) MR (calc.): Molal refraction calculated from atomic refractive indices. See page 9.

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ADVANCES IN CHEMISTRY SERIES

(nu - d/2): Refractivity intercept equals refractive index minus one half the density, both at the same temperature, 20 C.

D: Dielectric constant run at a frequency of 1()6 (cycles/sec.) and at 25 C. unless other-wise noted. When reported as data of The Dow Chemical Co., error about 0.005. Where Reference 5 is noted it was obtained by squaring the refractive index at 20 C.

A, B, C: Constants of the Antoine vapor pressure equation for the liquid state, giving P (pressure) in mm. and t (temperature) in C. This is in the range between the temperatures as indicated. These temperatures in general are the boiling point at 30 mm. to a TR of 0.75 to 0.80. See method of obtaining A, B, C on page 6. Antoine equation: log P = A - B/(t + C)

A, B*, K, c, tk, tx: Constants of the saturated vapor density equation log dy(g./ml.) = A* - B/(t + C) to the temperature tk log dy(g./ml.) = A - B/(t + C) + K/(1.1 Tc - 273.2 - t) + c from temperature h to a reduced temperature, Ta, of 0.92 tk = Temperature at which it is necessary to change from the simple vapor density equation to the corrected vapor density equation in the higher ranges, C. tk = tx + K/c and tx = (1.1 Tc - 273.2) C. A * and B where the ls.tent heat at the atmospheric boiling point is available. Vg - VL = (31381.7 X .1Hv X dt/dp)/T Where the ls.tent heat is not avails.ble use M(.1Hv)/TB = 21.0 and from this .1Hv = (TB X 21.0)/M The value 21.0 (or any other value as 21.4 say) is obtained from the nearest rels.ted compound which has a latent heat available. Then proceed as in case where ls.tent heat is avails.ble for Vg value at B.P. Since d. = l/Vg log dY710 = A - B/(ta + C) at 760 mm. log dY30 = A - B/(tao + C) at 30 mm. Solve for A, B, since t and d. at 760 mm. and 30 mm. and C are known.

A', B/, C/: Constants of the Antoine vapor pressure equation below 30 mm. pressure, covering the temperature range as indicated. See method of obtaining the constants on page 6.

A', B/*: Constants of the vapor density equation below 30 mm. These two values are obtained by using the boiling point at 30 mm. and the pressure at 25 C. (obtained from the values A', B I, C ') and assuming that at 25 0 C. the rels.tionship PV /RT = 1. Then we have Vg at 25 C. = RT/MP = 62,361 X (25 + 273.2)/MP. Then dv = I/Vg. Inserting these values of vapor density we then solve the two equations for the values of A' and B/ as in the case of A and B.

Ac, Bc, Cc: Constants of the Antoine vapor pressure equation for the liquid state from Ta = 0.75 (or a higher Ta as indicated) to the critical temperature. See method of obtaining the constants on page 7.

Cryoscopic Constants, A 0, BO: Cryoscopic constants for calculs.ting mole % purity. See J. Research Nall. Bur. Standards, 35 (1945); RP 1676.

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PHYSICAL PROPERTIES OF CHEMICAL COMPOUNDS 5

t.O C.: Temperature at which a mole of the vapor occupies 22.414 liters and the vapor is in equilibrium with the liquid, in 0 C.

B* te= -C (A * - log dvo)

dt/dp: Rate of change of boiling point with pressure, given by equation dt/dp = B/ [2.3026 X P X (A - log P)2Jo C./mm. ~Hm: Latent heat of fusion in caL/g. ~Hv: Latent heat of vaporization at the temperature designated, caL/g. t.(d, e): The latent heat of vaporization at the temperature to as given by the equation

~Hv = d - et, and indicates the accuracy of thiR equation at the temperature t . ~Hv/T.: ~Iolal latent heat of vaporization at t. divided by To. (Equal to the molal

entropy of vaporization at te.) d, e; d', e': These are parameters of the latent heat of vaporization equation, ~Hv

(caL/g.) = d - et. This is valid between the temperatures indicated. It has been found that the latent heat between the boiling point at 30 mm. and the boiling point at i60 mOl. is almost a linear function of the temperature. As seen in most cases this equation holds almost to the temperature te. Above and below this the latent heat is not linear with temperature except for short intervals.

d.: Critical density, g./mL v.: Critical volume, ml./g. to: Critical temperature, C. See also page 7. P. mm.: Critical pressure in mill. Whel'e this was not obtained from the literature it is

calculated as follows (The Thomson method, private communication from George W. Thomson): The critical temperature is inserted in the Antoine equation, using the A, B, and C values to calculate the critical pressure. This value is too low. This is then multiplied by 1.07 and is assumed to be the critical pressure. In the great majority of cases, this will agree with determined values to within 3%. For high boiling compounds this value must be decreased, since in most cases there is somewhat irl'egular drift with increasing temperature, so this should be continually lowered as the boiling point becomes increasingly higher.

PV /RT: Compressibility at the temperature designated. z = PV/RT where P = pressure in mill., V = volume in mL/mole, and R = 62361. ~Hc: Heat of combustion, kcaL/mole, gas at constant pressure, 298.160 K. or 250 C. ~Hf: Heat of formation, kcaL/mole, liquid at 298.16 K. or 250 C. ~Ff: Free energy of fOlnlation, kcal./mole, liquid at 298.16 K. or 25 C. ,,: Kinematic viscosity in centistokes, at temperature designated. The kinematic vis-

cosity is given by the equation log" = A" + B'/T between the temperatures indicated to an accuracy of 1% or better.

HoP. c., 30mm.; dt/dp; ~H,'; PV /RT: These ,'aluesat30mm. are calculated from the Antoine equation using A, B, lind C. It has been found that at 30 mOl. in almost all Cox ChaIt Families the ratio PY /RT is negligibly different from one. This, then, has been taken as olle point (the other point being the B.P. at 760 mm.) from which to calculate A * and B*, always assuming the compressibility as 1.0000 at 30 mm.

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6 ADVANaS IN CHEMISTRY SHIES

cp: Specific heat at constant pressure at temperature designated, cal./g. 0 K. Cy: Specific heat at constant volume at temperature designated, cal./g. 0 K. f, g, h, f', g', h': Parameters of the heat content equation for the liquid for the tempera-

ture ranges designated, 0 K. Cp (liquid) = f + gT + hTI

m, n, 0, m', n', 0': Parameters of the heat content equation for the vapor for the tempera-ture ranges designated, 0 K. Cp (vapor) = m + nT + oTt

'Y: Surface tension in dynes/cm., at temperature designated. [PI: Parachor at the temperature designated:

M('Y)'/'/(dL - dy) = [PI [PI Sugd.: Parachor from atomic and structural values &8 given by Sugden. See Table.

The parachor value for oxygen &8 hydroxyl (alcohols) in these tables is taken &8 15. Sugden gives the values of 20 for oxygen and 30 for oxygen in esters, which does not seem to work for alcohols and phenols.

Exp. L.l.; Exp. L.u.: Explosion limits lower and upper range, % by wt. Dispersion: Specific dispersion, 104(nr - nc)/d, ml./g. at 250 c.

nr, nc = refractive index for F and Clines. d = density, g./ml.

Flash and Fire Points, 0 C.: Cleveland open cup (ASTM D 92-46) if not otherwise desig-nated. Closed cup (ASTM D 56-36) will be designated &8 such.

M Spec.: Mass Spectrograph. Ultra V.: Ultraviolet. X-Ray Dif.: X-Ray Diffraction. Infrared: Infrared Spectrograph. Solubility at 250 C., in solvents as designated. Ezplanation of the methods used for calculating the variom parameter. in the foregoing: A, B, C: The A, B, and C constants, except where given by the API reports, are calcu-

lated by means of the Thomson method [Chem. Rev . , 38, 1-39 (1946)] using the determined boiling points at three different pressures. The three formulas for this are &8 follows: (y, - YI)/(YI - YI)(tt - tM(t. - tt) =1 - (t. - tl)/(t. + C) B = (Ya - YI)/(tt - tl)(tl + C)(ta + C) and A = YI + B/(tl + C) where Yh Y2, and y, are equal to log PI, log P"~ and log Paat temperatures t l, t

" and ta.

Unless the data for the three points are very accurate the C value can be considerably in error. As a check on this method an empirical formula developed by Thomson (private communication from George W. Thomson) will give a much better value of C if the data are much in error. This formula is C = 239 - 0.19b. The A and B values can then be readily determined from the two points given, since they are much less critical.

A', B', C' (for pressures below 30 mm.): Applicable when molar heats of vaporization are available at 250 C. and the Antoine equation can be used to obtain the boiling point at 30 mm. Let A, B, C be the constants of the usual Antoine equation valid above 30 mm. and let A', B', C' be the constants of the Antoine equation 8Oughtforbelow 30 mm. These two equations are taken to give the same value of the p~uretemperature slope at 30 mm. log 30 = A - B/(tl + C) = A' - B'/(tl + C') B/(t, + C)' = B'/(tl + C')2

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PHYSICAL PROPERTIES OF CHEMICAL COMPOUNDS 7

Since PV /RT may be assumed to be 1.0000 at th the temperature corresponding to 30 mm., and is also 1.0000 at 25 C., the molar heat of vaporization at 25 C.,

M~Hv2, is given by M~Hv2 = 2.3026 RB' l(t2 + 273.2)/(t2 + C')2 where t2 = 25 C. To solve for A', B', C' let

g2 = M~Hv2l2.3026 R(t2 + 273.2)2 = M.1Hv2l406883 if t2 = 25 0 C. Also g2 = B'/(t2 + C')2

Since th t2 and all values on left hand side of equations above are known then B' and C' are readily obtained as follows: [B'j(t! + C')2)[(tl + C')2/B') = g2 (tl + C'>,/B' = say, h2 Then C' = (tl - ht2)/(h - 1) and B' = g2(t2 + C')2 Also B' = B[(tl + C')/(tl + C)2 A' = log 30 + B'/(t. + C') since PI = 30 mm. These formulas were developed with the aid of George Thomson.

When heal8 of vaporization at 25 C. are not knoum: In this case the C' value is estimated and A' and B' are calculated from known data. It was noticed that C' has a value approximately 18 higher than C when latent heats at 25 C. are known. By adding this increment to C we have C', thenB' from the relation for the first case B' = B [(t30 + C')/(t3o + C)2 and then A' as in first case.

Ac, Bc, Cc: This method was developed by George Thomson [Chern. Re1J8., 38, No.1, 23 (1946)] and is similar to the one for obtaining A', B', C'. It is assumed that the parameters A, B, C of the Antoine equation are good to a T. 0.75 or a higher reduced temperature, and this temperature corresponds to the 25 C. in the case of A', B', C', and the critical point corresponds to the 30 mm. point. B/(tl + C)2.(t. - tl)/(y. - YI) = 1 + (to - tl)/(tl + Cc) and Bc = (y. - YI)/(t. - t.)(tl + Cc)(t. + Cc); Ac = B/(t. + Cc) + y. where tl C. = T. 0.75, t. 0 C. = critical temperature YI = log P at t l, y. = log P. The first equation is used to evaluate Cc, the lrecond, Bc, and the third, Ac.

As.qociation: The association in the vapor phase of organic acids seems to vary inversely as the temperature fOJ some acids, at least for part of the range. In part of the range, and also apparently for some acids over the whole range, the association is fairly con-stant. The association is given in these sheets by the formula ME = P - rt. For instance, for acetic acid this formula would be ME = 2.225 - 0.004085 t from 0 C. to 100 C. From 100 C. to a T. of 0.92, ME = 1.85. That is to say, the vapor density as calculated by the A *, B* formula would have to be multiplied by this correction factor to take care of the association. Further, if the reciprocal of the density is used as calculated to give vapor volume, it would be necessary to divide by 1.85 to get the actual vapor volume.

t.: Where the critical temperature has not been determined, it is calculated by Watson's equation: T./T, = 0.283(M/d.)o.18 where d. = liquid density, g./ml. at the boiling point, and M = molecular weight. This is used for ull hydrocarbons and halohydrocarbons.

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8 ADVANCES IN CHEMISTRY SERIES

f, g, h, m, n, 0, etc.: For a short temperature range the equation Cp = f + gT + hTI reproduces almost exactly determined data. The parameters were set up on the IBM machines using eight determined values where that many or more were available.

1. 2. :J. 4. 5. 6. i. 8. 9.

10. 11.

The IB~I machines were used to set up the Antoine con8tants from determined data. A preliminary C value was obtained from the equation C = 239. - O.19ta. A and B were then obtained and new C values either side of the first C used and new A and B values found. In each case above, the boiling points at the experimental pressures were calculated and compared with the determined boiling points. Actually the value of C was generally obtained from C = 239. - O.19ta, since the determined values must be very very accurate to give better values of C.

Cox Chart Famllie.

Alkyl and halo benzene" 12. Aromatic alcohols (Phenyl ethyl alcohols) Styrenes 13. Aromatic ketones Thiaalkyl benzenes 14. Aromatic esters Thiophenes 15. Cyclopentanes Alkyl naphthalenes 16. Cyclopentenes Tetrahydronaphthalenes Ii. Thiacyclopentanes

Decahydronaphthalene~ 18. Thiacyclopropanes Aromatic phenols 19. Cyclohexancs Thiophenols 20. Cyclohexenep Aromatic amine" 21. Thiacyclohexanes N itrobenzenf'll 22. Miscellaneous

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PHYSICAL PROPERnES Of CHEMICAL COMPOUNDS 9

Atomic Refractive Indices Used for Computing Molecular Refractive Index All values are for the sodium line.

Carbon singly bound and alone 2.592 NO as nitrites 5.91 Carbon singly bound 2.418 NO as nitrosoamine 5.37 Carbon double bond l.733 NO. as alkyl nitrite 7.44 Carbon triple bond 2.398 NO. as alkyl nitrate 7.59 Carbon conjugated 1.27 NO. as nitro paraffin 6:72 Hydrogen 1.100 NO. as nitro aromatic 7.30

Oxygen-hydroxyl 1.525 NO. as nitramine 7.51

Oxygen-ethereal 1.643 Fluorine 0.95-

Oxygen-ketonic 2.211 Chlorine 5.967 Oxygen-as ester 1.64 Bromine 8.865

Iodine 13.900 Sulfur-as SH 7.69 Sulfur-as RSR 7.97 Sulfur-as RCNS 7.91 Sulfur-as RSSR 8.11 Nitrogen

as aliphatic primary amine 2.45 as aromatic primary amine 3.21 as aliphatic secondary amine 2.65 as aromatic secondary amine 3.59 as aliphatic tertiary amine 3.00 as aromatic tertiary amine 4.36 as hydroxylamine 2.48 as hydrazine 2.47 as aliphatic cyanide 3.05 as aromatic cyanide 3.79 as aliphatic oxime 3.93 as primary amide 2.65 as secondary amide 2.27 as tertiary amide 2.71 This value for one fluorine atom attached to carbon. The value 1.1 is to be used for each

fluorine atom in polyfluorides.

Atomic and Structural Constants for Calculation of Parachor Sugden

CH..................... 39.0 C.................. ..... 4.8 H ...................... 17.1 0 ...................... 20.0 o (Alcohol)...... . . . . . . . . 15.0 O.(Ester).. .. . . . . . . . . . .. 60.0 N...................... 12.5 N (Nitrile). . . . . . . . . . . . .. 14.4 S ....................... 48.2 F ....................... 25.7 Cl..... . . . . .. .. .. . . . . . .. 54.3

Sugden Br...................... 68.0 I.. . . . . . . . . . . . . . . . . . . . .. 91.0 Single bond ............. . Double bond. . . . . . . . . . . .. 23 . 2 Triple bond. . . . . . . . . . . . .. 46.6 3-Membered ring.... . . . .. 16.7 4-Membered ring......... 11.6 5-Membered ring.... . . . . . 8.5 6-Membered ring.... . . . . . 6.1 7-Membered ring ........ . Aliphatic alcohol. .. subtract 6.0

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TABLE I. ALKYL AND HALO BENZENES

No I

NAME I Benzene STRUCTURAL FORMULA I

Mole 1 RefJ Molecular "Pur. 99.9961 z'l Formula C6H6

R.f

I Molecular W.,,-ht 78. 108 Ref

F P C Z dt/dP f I 5.533 F. P. 100'10 C/mm I I

Z5C O. ZZ76 5 I B.;fr; C 80.100 Z BP 0.04Z71 Z h

100 mm Z6.075 Z te 0.0355 5 f' I

o 1 to 1_- _.~

R.f

O. Z605 4 0.0331 4 0.0669 4

~~ _I~: ~O : 30 mm 0.5949 4 ::! 6Hm calli 30.09 Z I--=-L""""'T----I----I---l ~--~1----~~-4~5~.----~5~1~~~~~1_~~~--r_~ m t 1 300to

Pre ure mm Z5C

t. Density Ilml ZO"C dt Z5

4 30

9S.18 964.4

5 5

6Hv calli I Z5C 103.57 Z n I _ IQO....:~ 30mm 108.19 4 0 1 BP 94.14 Z m'l te 9Z.65 5 n' I

0.87901 Z te (d, e) 91.71 5 0' I 0.87370 Z 6Hv/Te ZO.03 5

-0.1030 4 0.0014 4

-0.0671 4

0.86837 4 Surface tenoion a 0.900Z5 4 :: ~!~ 10~:~~1l ~ dynes/cm. ZOOC Z8.88 Z

r-:b=--___ +--=:-0::.;.:..:0:..:0~1.:.05::..j....:4!.....1I-d.,- 0 to 108.79 5. 30 Z7.49 Z Ref. Inde,. lI...:e!:':"LI--=-Z~5~.~C:.+_~0.:..!Z:..!0~8~8~":5~1r.~=:;:::-,;4;;;01t-'Z:..:6", ..:;1..:;4-rZ~

nO ZOC I. SOliZ Z I~ Parachor [p] Z5 1.4979Z Z dc Ilml 0.300 Z ZO"C Z06.06 Vc mill 3.333 Z 30 1. 49468 4 t.C Z89.45 Z 30 Z06.10

c 40 Z06.11

MR (Ob ) MR (Calc.) (nD-d/Z)

0.7500 4 Pc mm 36936. Z Suld. Z07. I z6.1835 Z PV IRT Exp. L.l. "/wt. 1. 8

1.0616Z Z ZSC 0.99ZZ 4 u. 7.7 30mm 1.0000 5 Disperaion 189.Z

Dielectric Z.Z83 I BP 0.9658 4 Flash Point .C~ -11. A I 0 to 6.90565 Z t. o. 9596 5 Fire Point B 1.l.6.Q. :"C_ IZ11. 033 Z tc O. Z74 Z C ZZO.79 Z 6Hc kcal/m

.1 6W A, IS to 1.19411 4 6Ff B.l!5,!... 11 Z7. 9 4 K Z5.0 4 Visco.ity c -0.13147 4 centistoke. tk fT50to ISS. 4." ZOC

~ IZ45C 345.8 5 30 ~I ~ 50 B'I __ o. 70 C' BV 1 Z5 to A'. to A v I 80 C B'. C 1-(B"iI - to-~~--~+-------+-~I

AclI60 to 7. 4Z91Z 5 (A VII C BCLtc C 16Z8.3Z 5 c liq.300.K Cc - - Z79.56 5 P 3Z0 Cryos. A 0.015Z3 Z c p vap.30(1'K con.t B 0.003Z Z 400 te C 88.04 5

757.5Z 11.718 Z9.756

0.74Z7 0.659Z 0.5156 o 4148

5Z3.4 1.09Z90

Z Z Z

I I

: 4 4

0.4178 3z 0.4315 3z 0.Z516 Z 0.34Z4 Z

M. Spec. Ultra V. X-Ray DU. Infrared Solubility in ..

Acetone Carbon tet. Ben.ene Ether n-Heptane Ethanol Water #-Water in

#-

Yea Yea Yes

99.

GO GO GO GO GO GO 0.174 7.0 0.ZZ6

TR = O.77Tc '" closed cup Irama/lOO Irams aolvent REFERENCES: I-Dow Z-API 3-Lit. 4-Calc. from det. data 5-Calc. by formula SOURCE: API PURIFICATION: API

LITERATURE REFERENCES: 3 J.A.C.S . .!!' 1573 (1951); 3' Chem. Met. Enl. 44-IZ, 733 (1947); 3z Timmerman.

11

4 4 4 5 3

'

3'

Z

3

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IZ ADVANCES m CHE.uSTRYSER~

No Z

NAME I Toluene STRUCTURAL FORMULA I Methylbenzene OCH 3

Mole IRef.1 Moleculer C7H8 r Moleculer i- Pur. 99.999 Z Formule Wei.ht 9Z.134

Ref ReI [ReI. F P. C _q4 qql Z dt/dP I I I 5 to 0.3971 4 F.P. 100ft C/mm I I !l1.Q. ~~ -0.0359 4 Z5C 0.6808 4 B.P. C BP 0.0463 Z h O.O~ZI 4 760mm 110.6Z5 Z

te 0.0360 5 I' I to 100 51. 944 4 I' I 1 __ ~K 30 Z6.04 4 30mm 0.6487 4

10 6.37 5 6Hm callI 17.17 Z h' I I -Z6. I ? 5 1300 -0.0654 4 6Hv calli m I to Pre ur. n I 12~ ~ 0.0013 4 Z5C 98.55 Z mm ZSC Z8.437 4 0 -0.0655 4

te 1048.Z 4 30mm 97.9 5 I BP 86.80 Z m' 1700 to 0.0471 4 I Denaity te 84.73 5 n' 1.!.0~ ~ 0.0398 4 Ilml ZO"C 0.86694 Z te (d,e) 85.17 5 0' I -0.0635 4

dt Z5 0.86Z30 Z 6Hv/Te 19.74 5 1 4 30 0.85757 4 d 1 Z5 to 101. 98 5 Sudace tenaion a 0.88547 4 ~...! ~3!L. dynea/cm. ZOC Z8.53 Z b -0.0,9Z4 4 0.1372 5 J 30 Z7.3Z Z d' 1 to 40 Z6.15 Z ReI. Jade,. e' I C

aD ZO"C 1. 49693 Z dc Ilml 0.Z88 Z Parachor [p]

Z5 1. 49414 Z ZOC Z45.63 4 30 1.491Z9 4 v mill 3.473 Z 30 Z45.68 4 t C C lZQ.8 Z 40 Z45.71 4 lie" 4 c 0.7545

Pc mm 30400. Z SUld. Z46.1 5 MR (Oba.) 31. 095 Z P~~RT E,.p. L.l. '!Io/wt. 1. Z4 3' MR (Calc.) 30.9Z5 5 Z5C 0.9968 4 u. 19.3 3' (aD-d/Z) 1.06346 Z 30 mm 0.9966 4 Olaperoion 184.7 Z Dielectric Z.379 3 BP 0.9613 4 Fleah PointC 4.44-"- 3' A I ZO to 6.95334 Z te 0.95ZZ 5 Fire Point

tc 0.Z63 4 B ~O.!!_:~ 1343.943 Z M Spec. Yea I C ZI9.377 Z 6Hc kcal/m 901.50 Z 6Hl Z.867 Z Ultra V. Yea I Ael ZO to I.Z79Z3 4 6FI Z7.Z8Z Z X-Ray Dil. B81212" . IZ5~.3 4 Inlrared 865. I

K Z3. 5 Viacoalty Solubility in + c -0. 11760 5 cead.toke~ 'It 1T75"'"to- 175. 5

" ZO C 0.67778 I Acetone GO

t,. I Z70 C 380.0 5 40 0.56457 I Carbon tet. GO 60 0.458Z5 I Ben De GO A'I to 80 0.39119 I Ether GO B'L_~ n-Heptane GO

C' BV I 40 to 440.66 4 Ethanol GO A'e to AV I 90 C !.34476 4 Water 7.3 I B'e OC t'(BV) I - -t';- Water iD 0.055 I Ac I ZOO to 7.45657 4 (AV) I

C BcL.!c C 1796.9 4 c p liq. Cc -,;" Z84.6Z 4 K

Cryoa. A 0.OZ508 Z c p vap.300"K 0.Z708 Z coa.te o Be 0.0019 Z 400 0.3609 Z te C IZZ.34 5 C y Yap.

f. closed CUD + nama/lOO "rama solvent REFERENCES: 1-0_ Z-API 3-Lit. 4-Calc. Irom det. data 5-Calc. by lormula SOURCE: API PURIFICATION: API UTERATURE REFERENCES: 3 NBS 514; 3' Nat. Fire Prot. Assoc. 3Z5 (1949)

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TABLE I. ALKYL AND HALO BENZENES

NAME 1t-__ E_th_y_l_be_n_z_e_n_e _____________ -i I

Mole IRef ,! Molecular " Pur. 99.995 I z'l Formula C 8H IO I Molecular Weight 106.160

13

No 3

STRUCTURAL FORMULA OC2H5 Ref Ref Ref

F P C 2 dt/dP f ' F. P. 100'll0 oc/rrun I I

I to ___ .K.

ZSC 1.8Z86 5 B. P. C BP 0.04898 Z l-.::h'""'"I-....----t----+---i

760 mm 136.186 Z 6 5 f' I I to 100 74.10 Z te 0.030, ~ __ .K

~~ ~:: ~~ : 30 mm 0.6866 4 :' i 1 __ ~I __ ~~-19~.Z~-~S~I~6~Hm~:c~a~I/:I~t_~ZO~.~6~3-_r~Z~---~~-r~-~-~~~~ t- 6Hv calli m I I 300 to -0.0734 4

ZS.C 95.11 Z n I 1_6..Q.0~~ 0.0014 4 Pre.aure rrun ZsC

te 9.571

llZ8. 5 5 30 rrun 93.00 4 0 I -0.0661 4

Density Ilml ZODC dt Z5

BP 81. 00 Z m' I 0.8670Z Z te (d ) 78.97 5 n' I 0.86Z64 Z te.e 78.94 5 0' I 0.8S8Z6 4 6Hv /Te 19.74 5

I 700 to l!.oQJ! ':'K 0.0675 4 0.0399 4

-0.0635 4 4 30

d 45 to 99. Z6 4 Surface tenaion a 0.88453 4 e I 160.C 0.1341 4 dynea/cm. ZOC Z9.04 Z

t-b ____ +---'-O:..: . ..:0""",18.:,.7-+_4'-iI-d 'li5to 97.54 4' 30 Z7.93 Z Ref. Index "_e~':"'L 1:!.4~S _~C~_~O:..:. 0~9~7~3~~4-l~-;;:::~:::,,4;;;0IrZ_6-'._7..:..9_IZ1

nD ZODC 1. 49588 Z It Z Parachor [p] Z5 1.493Z0 Z dc Ilml O. Z9 ZOC Z84.3 30 1.4904 4 Vc mill 3.448 Z 30 Z84.4

tc C 346.4 Z 40 Z84.3

MR (Oba.) MR (Calc.) (nD-d/Z)

0.7SZ8 4 Pc rrun Z81Z0. Z Suld. Z8S. I 35.761 Z PV/RT 35.543 5 ZS.C I. 06Z37 Z 30 rrun

Dielectric Z. Z38 5 BP Z !e Z c

A I 45 to 6.95719 B I 190C 14Z4. ZSS C - --- Z13.Z06 Z 6Hc kcal/m

6Hf 5 6Ff 5

Viscoaity cenUatokea ." ZOC

40 A'I zo to B'I 4SC C,---

7.3ZSZS 5 60 16ZZ.0 5 _80 Z30.7 5 BV I zo to

A V '90 C A'e ZS to 1. 69ZZ4 55 f-(B::V)-' 90- -to-B'e 4SC ISZZ.4 ~~---~------+--~I

Acl190to 7.3729 5 (Av)nSO C BCLtc C 1779.0 5 Cc - - z60.6 5 Cryoa. A 0.03471 conata. B O. 00Z9 te C lSI. SZ

Z Z 5

K

c p vaP.30d'K 400

1. 0000 1. 0000 0.96SZ 0.9547 0.Z66

1048.53 -Z.977 Z8.614

0.78Z3 0.6305 O.SZS

_0,447

413.1 2'.48073

408.5 2'. 494Z8

0.Z9088 0.38395

5 5 4 5 Z Z Z Z

Z Z Z 2

4 4 4 4

Z Z

Exp. L.I. "'_t. u.

Diaperaion Fla ah Point C Fire Point M. Spec. Ultra V. X-Ray DU. Infrared Solubility in

Acetone Carbon tet. BeD De Ether n-Heptane Ethanol Water Water in

174.7 15.0

Yea Yee

507.

III III III III III III O.OZO 0.114

Irame/lOO Irams aolvent REFERENCES: I-Dow Z-API 3-Lit. 4-Calc. from det. data 5-Calc. by formula SOURCE: API PURIFICATION: API LITERATURE REFERENCES: 3 Nat. Fire Prot. Aesoc. 3ZS (1949)

4 4 4 5

Z 3

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