PHYSICAL OF PHYSICAL PROPERTIES PROPERTIES OF
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-195...
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PHYSICAL OF PHYSICAL PROPERTIES PROPERTIES OF
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.fw001
CHEMICAL COMPOUNDS CHEMICAL COMPOUNDS A A systematic tabular presentation of accurate data on the physical properties of 511 organic cyclic Dow compounds compiled by R. R. Dreisbach of the Dow Chemical Co. These comprehensive and basic data were determined for specially prepared, 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 Number fifteen fifteen of of the the Advances Advances inin Chemistry Chemistry Series Series Industrial and Edited Edited by b y the the staff staff of of Industrial and Engineering Engineering Chemistry Published P u b l i s h e d June J u n e 1955 1955 by by AMERICAN A M E R I C A N CHEMICAL C H E M I C A L SOCIETY SOCIETY 1155 Sixteenth Street, N.W. N.W. 1155 Washington, W a s h i n g t o n , D. C.
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.fw001
Copyright 1955 1955 by by AIIERlcAN CHEMICAL AMERICAN CHEMICAL SoCIETY SOCIETY All Reserved AU Rights Rightll Ruerv«l
Physical Properties
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
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
% Pur.: Mole % purity by weight. F.P.! Freezing point, ° C.
Mol.
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. d 20, 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.
+ 0.4) l)/(nfi + 2) X
"c"
"C": Constant of the Eykman equation, (nfi - 1)/(no
X l/d =
MR (obs.): Molal refraction (obs.) = (nfi (M = mol. wt.)
M/d = MR at 20° C.
MR (calc.): Molal refraction calculated from atomic refractive indices. See page 9. 3
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 otherwise 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.
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
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.
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. te=
B* -C (A * - log dvo)
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
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, 298.16 0 K. or 25 0 C. ~Hf: Heat of formation, kcaL/mole, liquid at 298.16° K. or 25 0 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 viscosity 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.
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
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 temperature 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 temperature 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 25 0 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 designated. 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 25 0 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 calculated 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 25 0 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~ure temperature slope at 30 mm. log 30 = A - B/(tl + C) = A' - B'/(tl + C') B/(t , C)' = B'/(tl + C')2
+
7
PHYSICAL PROPERTIES OF CHEMICAL COMPOUNDS
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 C. Also g2 = B'/(t2 + C')2
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
0
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, h 2 Then C' = (tl - ht2)/(h - 1) and B' = g2(t 2 + 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 constant. 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.
ADVANCES IN CHEMISTRY SERIES
8
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.
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
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. 1. Alkyl and halo benzene" 2. Styrenes :J. Thiaalkyl benzenes 4. Thiophenes 5. Alkyl naphthalenes 6. Tetrahydronaphthalenes
i.
Decahydronaphthalene~
Aromatic phenols Thiophenols Aromatic amine" 11. N itrobenzenf'll 8. 9. 10.
12. 13. 14. 15. 16. Ii. 18. 19. 20. 21. 22.
Aromatic alcohols (Phenyl ethyl alcohols) Aromatic ketones Aromatic esters Cyclopentanes Cyclopentenes Thiacyclopentanes Thiacyclopropanes Cyclohexancs Cyclohexenep Thiacyclohexanes Miscellaneous
PHYSICAL PROPERnES Of CHEMICAL COMPOUNDS
9
Atomic Refractive Indices Used for Computing Molecular Refractive Index
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
All values are for the sodium line. Carbon singly bound and alone Carbon singly bound Carbon double bond Carbon triple bond Carbon conjugated Hydrogen Oxygen-hydroxyl Oxygen-ethereal Oxygen-ketonic Oxygen-as ester
2.592 2.418 l.733 2.398 1.27 1.100 1.525 1.643 2.211 1.64
Sulfur-as SH Sulfur-as RSR Sulfur-as RCNS Sulfur-as RSSR Nitrogen as aliphatic primary amine as aromatic primary amine as aliphatic secondary amine as aromatic secondary amine as aliphatic tertiary amine as aromatic tertiary amine as hydroxylamine as hydrazine as aliphatic cyanide as aromatic cyanide as aliphatic oxime as primary amide as secondary amide as tertiary amide
7.69 7.97 7.91 8.11
NO as nitrites NO as nitrosoamine NO. as alkyl nitrite NO. as alkyl nitrate NO. as nitro paraffin NO. as nitro aromatic NO. as nitramine Fluorine Chlorine Bromine Iodine
5.91 5.37 7.44 7.59 6:72 7.30 7.51 0.955.967 8.865 13.900
2.45 3.21 2.65 3.59 3.00 4.36 2.48 2.47 3.05 3.79 3.93 2.65 2.27 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 CH.....................
C.................. ..... H ...................... 0 ...................... o (Alcohol)...... . . . . . . . . O.(Ester).. .. . . . . . . . . . .. N...................... N (Nitrile). . . . . . . . . . . . .. S ....................... F ....................... Cl..... . . . . .. .. .. . . . . . ..
Sugden 39.0 4.8 17.1 20.0 15.0 60.0 12.5 14.4 48.2 25.7 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
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
TABLE I.
ALKYL AND HALO BENZENES No
I I
NAME
Benzene
Mole 1RefJ Molecular "Pur. 99.9961 z'l Formula C 6H 6
B.;fr; ·C 100 mm
Molecular W.,,-ht 78. 108
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
~~
Ref
Z
dt/dP
f I
·C/mm 80.100 Z6.075
_I~: ~O
o
I
R.f 5.533
F P ·C F. P. 100'10
I
STRUCTURAL FORMULA
Z5·C BP te
Z Z :
5 Z 5
Ref. Inde,. nO ZO·C Z5 30
I. SOliZ 1.4979Z 1. 49468 0.7500
MR (Ob •• ) MR (Calc.)
I
h f'
I
::!
1
4 4
0.0669
4
to
1_- _.~
Z Z
Dielectric Z.Z83 A I 0 to 6.90565 B 1.l.6.Q. :"C_ IZ11. 033 C ZZO.79
I Z Z Z
.1
A·, IS to 1.19411 B.l!5,!..·£. 11 Z7. 9 K Z5.0 c -0.13147 tk fT50to ISS. ~ IZ45·C 345.8 ~I
~
B'I _ _ o£.
C' A'. B'.
to ·C
AclI60 BCLtc Cc Cryos. con.t ••
to ·C A· B·
PV IRT ZS·C 30mm BP t. tc 6Hc kcal/m 6W
4 6Ff 4 4 Visco.ity 4 centistoke. 4." ZO·C 5 30 50 70 B V 1 Z5 to A v I 80 ·C
1-(B"iI - to-
~~--~+-------+-~I
7. 4Z91Z 16Z8.3Z Z79.56 0.015Z3 0.003Z
te ·C 88.04 TR = O.77Tc REFERENCES: SOURCE: PURIFICATION:
I-Dow
t
lI...:e!:':"LI--=-Z~5~.~C:.+_~0.:..!Z:..!0~8~8~":5~1r.~=:;:::-,;4;;;01t-'Z:..:6",•..:;1..:;4-rZ~
Z I~ Z d c Ilml Vc mill 4 t.C c 4 Pc mm
z6.1835 1.0616Z
(nD-d/Z)
0.5949 30.09
I
R.f O. Z605 0.0 3 31
4 Z I--=-L""""'T----I----I---l ~--~1----~~-4~5~.----~5~1~~~~~1_~~~--r_~ m 1 300to -0.1030 4 6Hv calli I Pre •• ure Z5·C 103.57 Z n I _ IQO....:~ 0.0014 4 mm Z5·C 9S.18 5 -0.0 6 71 4 30mm 108.19 4 0 1 964.4 5 t. BP 94.14 Z m'l Density te 9Z.65 5 n' I Ilml ZO"C 0.87901 Z te (d, e) 91.71 5 0' I dt Z5 0.87370 Z 6Hv/Te ZO.03 5 4 30 0.86837 4 Surface tenoion a 0.900Z5 4 :: ~!~ 10~:~~1l ~ dynes/cm. ZOOC Z8.88 Z +--=:-0::.;.:..:0:..:0~1.:.05::..j....:4!.....1I-d.,- 0 to 108.79 5. 30 Z7.49 Z
r-:b=--___
30 mm 6Hm calli
O. ZZ76 0.04Z71 0.0355
I
5 5 5 Z Z
0.300 3.333 Z89.45 36936.
Z Z Z Z
0.99ZZ 1.0000 0.9658 o. 9596 O. Z74 757.5Z 11.718 Z9.756
4 5 4 5 Z
0.74Z7 0.659Z 0.5156 o 4148
I I
Z Z Z
:
5Z3.4 1.09Z90
4
0.4178 0.4315 0.Z516 0.34Z4
3z 3z Z Z
4
Parachor [p] ZO"C 30 40 Suld.
Exp. L.l. "/wt. 1. 8 u. 7.7 Disperaion 189.Z Flash Point .C~ -11. Fire Point M. Spec. Ultra V. X-Ray DU. Infrared
Solubility in .. Acetone Carbon tet. Ben.ene Ether n-Heptane Ethanol Water #Water in
#-
(AVII °C c liq.300.K P 3Z0 c p vap.30(1'K 400
Z06.06 Z06.10 Z06.11 Z07. I
11
3' 3' Z
GO GO GO GO GO
0.174 7.0 0.ZZ6
API
.!!'
5
GO
'" closed cup Irama/lOO Irams aolvent Z-API 3-Lit. 4-Calc. from det. data 5-Calc. by formula API
3 J.A.C.S .
4
Yea Yea Yes 99.
5
LITERATURE REFERENCES: 733 (1947); 3 z Timmerman.
4 4
1573 (1951); 3' Chem. Met. Enl. 44-IZ,
3
IZ
ADVANCES
m
CHE.uSTRYSER~
No
I
NAME
I
Toluene
r Moleculer Wei.ht 9Z.134
C 7H8
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
_q4 qql
Pre •• ur. mm ZS·C te Denaity Ilml ZO"C Z5 dt 30 4 a b
Z
Z8.437 1048.Z
0.88547 -0.0,9Z4
4 4
1. 49693 1. 49414 1.491Z9
Z Z 4
0.7545
4
MR (Oba.) MR (Calc.) (aD-d/Z)
31. 095 30.9Z5 1.06346
Z 5 Z
Dielectric A I ZO to B ~O.!!_:~ C Ael ZO to B81212" .£
Z.379 6.95334 1343.943 ZI9.377
3 Z Z Z
I.Z79Z3
4 4 5 5 5 5
c
'It 1T75"'"tot,. I Z70 ·C A'I
IZ5~.3
Z3. -0. 11760 175. 380.0
6Hm callI 6Hv calli Z5·C 30mm BP te te (d,e)
4 4 Z Z 4
lie"
Z5·C BP te 30mm
Z 4 4 5 5
0.86694 0.86Z30 0.85757
ReI. Jade,. aD ZO"C Z5 30
K
dt/dP
·C/mm 110.6Z5 51. 944 Z6.04 6.37 -Z6. I ?
6Hv/Te d 1 Z5 to ~...! ~3!L·.£ d' 1 to e' I ·C d c Ilml v mill t cC ·C Pc mm
C' A'e B'e
to OC
Ac I ZOO to BcL.!c ·C Cc -,;"
7.45657 1796.9 Z84.6Z
4 4 4
0.OZ508 0.0019
Z Z
Cryoa. A· coa.te Be o
te ·C
IZZ.34
f. closed CUD REFERENCES: 1-0_ SOURCE:
0.6808 0.0463 0.0360
4 Z 5
0.6487
4
17.17
Z5·C 30 mm BP te tc 6Hc kcal/m 6Hl 6FI
Z
98.55 97.9 86.80 84.73 85.17
Z 5 Z 5 5
19.74
5
101. 98 0.1372
5 5
0.Z88 3.473 lZQ.8
Z Z Z
30400.
P~~RT
0.9968 0.9966 0.9613 0.95ZZ 0.Z63 901.50 Z.867 Z7.Z8Z
Z 4 4 4 5 4 Z Z Z
Viacoalty cead.toke~
"
to
B'L_~
3
[ReI.
ReI
Ref
B.P. ·C 760mm 100 30 10 I
OCH
Methylbenzene
Mole IRef.1 Moleculer i- Pur. 99.999 Z Formule F P. ·C F.P. 100ft
Z
STRUCTURAL FORMULA
ZO 40 60 80
·C
B V I 40 to A V I 90 ·C t'(BV) I - -t';(A V) I ·C c p liq. ·K
5 Z-API
c p vap.300"K 400 Yap.
0.67778 0.56457 0.458Z5 0.39119
I I I I
440.66 !.34476
4 4
0.Z708 0.3609
I
I I h
I
I' I' h'
I
m n 0
I I
0'
I
I
0.3971 4 -0.0 3 59 4
5 to !l1.Q. ~~
O.O~ZI
4
1300 to 12°~ ~
-0.0654 0.0013 -0.0 6 55
4 4 4
1700 to
0.0471 4 0.0 398 4 -0.0 6 35 4
I to 1__ ~K
I
I m' I n'
1.!.0~ ~
1 Sudace tenaion dynea/cm. ZO·C J 30 40 Parachor [p] ZO·C 30 40 SUld. E,.p. L.l. '!Io/wt. u. Olaperoion Fleah Point·C Fire Point M Spec. Ultra V. X-Ray Dil. Inlrared Solubility in Acetone Carbon tet.
Z8.53 Z7.3Z Z6.15
Z Z Z
Z45.63 Z45.68 Z45.71 Z46.1
4 4 4 5
1. Z4 19.3 184.7 4.44-"-
3' 3' Z
Yea Yea
I I
865.
Ben •• De
Ether n-Heptane Ethanol Water Water iD
GO GO GO GO
7.3 0.055
+ nama/lOO "rama solvent 5-Calc. by lormula
API
PURIFICATION:
API UTERATURE REFERENCES:
GO GO
Z Z
4-Calc. Irom det. data
I
+
Cy
3-Lit.
3'
3 NBS 514; 3' Nat. Fire Prot. Assoc. 3Z5 (1949)
I I
13 TABLE
I.
ALKYL AND HALO BENZENES No
NAME
1t-__E_th_y_l_be_n_z_e_n_e_ _ _ _ _ _ _ _ _ _ _ _ _-i
I I ,! I
Mole Ref Molecular " Pur. 99.995 z'l Formula C 8H IO F P ·C F. P. 100'll0 B. P. ·C 760 mm 100
~~
2
I
Ref dt/dP
f I
oc/rrun 136.186 74.10
~:: ~~
OC
Molecular Weight 106.160
Ref
ZS·C BP
Z Z :
3
STRUCTURAL FORMULA
' I
2H 5
I___.K.
Ref
to
te
1.8Z86 5 0.04898 Z l-.::h'""'"I-....----t----+---i 6 5 f' I to 0.030, ~ __ .K
30 mm
0.6866
I
4
:'
i
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
1 _ _~I_ _~~-19~.Z~-~S~I~6~Hm~:c~a~I/:I~t_~ZO~.~6~3-_r~Z~---~~-r~-~-~~~~
I
t-
6Hv calli m I 300 to -0.0734 4 Pre.aure ZS.C 95.11 Z n I 1_6..Q.0~~ 0.0014 4 rrun Zs·C 5 9.571 30 rrun 93.00 4 0 I -0.0 6 61 4 llZ8. 5 te BP 81. 00 Z m' I I 700 to 0.0675 4 Density 0.8670Z Z te (d ) 78.97 5 n' I l!.oQJ! ':'K 0.0 3 99 4 Ilml ZODC 0.86Z64 Z te.e 78.94 5 0' I -0.0 6 35 4 dt Z5 0.8S8Z6 4 6Hv /Te 19.74 5 4 30 d 45 to 99. Z6 4 Surface tenaion a 0.88453 4 e I 160.C 0.1341 4 dynea/cm. ZO·C 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 n D ZODC 1. 49588 Z It Z Parachor [p] Z5 1.493Z0 Z d c Ilml O. Z9 ZO·C Z84.3 4 30 1.4904 4 Vc mill 3.448 Z 30 Z84.4 4 tc ·C 346.4 Z 40 Z84.3 4 0.7SZ8 4 Pc rrun Z81Z0. Z Suld. Z8S. I 5 MR (Oba.) 35.761 Z PV/RT Exp. L.I. MR (Calc.) 35.543 5 ZS.C 1. 0000 5 u. (nD-d/Z) I. 06Z37 Z 30 rrun Diaperaion 1. 0000 5 Z 174.7 Dielectric Z. Z38 5 BP 0.96SZ 4 Fla ah Point ·C 15.0 3 0.9547 5 A I 45 to 6.95719 Z Fire Point 0.Z66 Z B I 190·C 14Z4. ZSS Z c Yea M. Spec. C - - - - Z13.Z06 Z 6Hc kcal/m Z 1048.53 Ultra V. Yee 6Hf Z -Z.977 X-Ray DU. 5 6Ff Z8.614 Z Infrared 507. 5 Viscoaity Solubility in cenUatokea Acetone III 0.78Z3 Z ." ZO·C Carbon tet. III Z 40 0.6305 BeD •• De III O.SZS Z 7.3ZSZS 5 60 A'I zo to Ether III _0,447 2 5 _80 B'I 4S·C 16ZZ.0 n-Heptane III C,--- Z30.7 5 B V I zo to Ethanol III 413.1 4 Water O.OZO A V '90 ·C 2'.48073 4 A'e ZS to 1. 69ZZ4 55 f-(B::V)-'90- -toWater in 0.114 B'e 4S·C ISZZ.4 408.5 4 ~~---~------+--~I Acl190to 7.3729 5 (Av)nSO ·C 2'. 494Z8 4 BCLtc ·C 1779.0 5 ·K Cc z60.6 5
"'_t.
!e
Cryoa. A· conata. B· te ·C
0.03471 O. 00Z9 lSI. SZ
REFERENCES: SOURCE: PURIFICATION:
I-Dow
Z Z
c p vaP.30d'K 400
0.Z9088 0.38395
Z Z
5 Z-API
3-Lit.
4-Calc. from det. data
Irame/lOO Irams aolvent 5-Calc. by formula
API
API LITERATURE REFERENCES: 3 Nat. Fire Prot. Aesoc. 3ZS (1949)
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Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
TABLE
XXII.
523
MISCELLANEOUS No. o-Chlorobenzaldehyde
NAME
Mole % P u r . 9 9 . 61
Ref. 1
STRUCTURAL CHO
MolecuUr Formula 7 5 c
H
C
1
Ref,
RefJ 12. 19 12.39
F . P . IÇ F . P . TOOT
Published on January 1, 1961 on http://pubs.acs.org | doi: 10.1021/ba-1955-0015.ch001
Pressure m m 25*C
211.89 140.40 108.63 84. 31 4 3 . 53
1.24829 1.24320 1.23811
2 5
d
1.26865 - 0 . 00102 Ref. n
Index 20*C 25 30
1.56620 1.56384 1.56161
M R (Obs.) M R (Calc.) (nD-d/2)
37.005 37.073 0.94206
n
u
48.61 0. 05615 0. 03665
30 m m
94.47 8 5 . 55 72.53 69.72 69.43
e
t (d.e) e
to ^C_ to *C
99.25 0. 1261 9 7 . 14 0.1067
I I
j
I tcT L _ 1 K Surface tension dyne β/cm. 2 0 C Ϊ 30 40 #
Parachor
d g/ml v ml/g c
20 C 30 40 Sugd e
0.59201
A · 109 to Β l290_^C C
7.06216 1718.10 199.
Α · Ι ΐ 0 9 to B*(246_*C_
1.52895 1623. 5
PV/RT 25 C 30 m m BP
if'
A He k c a l / m A Hi AFf
η 7.38896 1925.0 217.
A * 25 to Β·*109 C
1.85246 1823.9
1
#
Acl
%
Viscosity centistokes
Α · I 25 to B'|109 C C» #
1.0000 1.0000 0.9405 0.9222
e
to •C
-c
I
to
to
(A )|
•c
v
c Cryos. A* consts. B*
0.01986 236.44
to •C
(B )| v
liq.
·Κ
c
vap.
*K
c
vap.
p
* p u r i t y 9 9 . 39 m o l e % REFERENCES: SOURCE: PURIFICATION: LITERATURE
1-Dow
31.70 30. 68 2 9 . 68
tP]
c
Dielectric
Ref.
to
19.37
e
. d I 109 l e l_23_6_ d'"~| 25 e» ! 109 1
»
h' i m
ΔΗν cal/g 25 C 30 m m BP
AHv/T
f 8 h
0.7974 22.67
A H m cal/g
0.2718 1307.6
Density g / m l 2