VL Critical Prop Elements Compounds Unsat Aliphatic HCs

8/3/2019 VL Critical Prop Elements Compounds Unsat Aliphatic HCs

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R e v i e w s

a po r-Li q u i d Cr it i c a l P r o p e r t i e s o f El e m e n t s a n d C o m p o u n d s . 6 .

n s a t u r a t e d Al ip h a t i c H y d r o c a rb o n s

o n s ta n t i n e T s o n o p o u l os *

xon Research and Engineering Company, P.O. Box 101, Florham Park, New Jersey 07932

o ug l a s A m br o s e

epartm ent of Chemistry, Un iversity College London, 20 Gordon Street, London WC1H 0AJ , En glan d

This is pa rt 6 of a series of contributions by th e critical pr operties group of the IUP AC Commission I.2on Thermodynamics, Subcommittee on Therm odynam ic Data. It pr esents all known experimental dat afor the critical consta nts of unsatu rat ed aliphatic hydrocarbons, which have been divided into fivefamilies: linear a lk-1-enes (10 compounds, C 2 t o C12 ); other alkenes (8 compounds, C4 t o C6); alkadienes(3 compounds, C3 t o C6); terpenes (3 C 10 compounds); and alkynes (3 compounds, C 2 t o C4). Recom-mendat ions a re given together with un certainties. Critical temperat ures h ave been converted to ITS-90 .

T h e u n s a t u r a t e d a l ip h a t ic h y d r oca r b on s h a v e b ee nvided into five families: (a) linear alk-1-enes; (b) oth erkenes; (c) alkadienes; (d) terpenes; (e) alkynes. Morea n on e -t h i r d of t h e r e fe r en ce s a r e on e t h en e , com -ercially the most importa nt organic chemical. Not sur-

singly, the critical properties of ethene are known verycura t e l y. On t h e ot he r ha nd, t h e i nforma t i on on a l ka -enes and t erpenes is very limited. The presentation andaluation of the experimental data follow the guidelinesAmbrose et al. in parts 1 and 2 of this series [95-amb/u, 95-amb/tso]. The r ecommended values ar e given inble 1, while all kn own dat a h ave been collected in Ta bleThe references follow the format [year-first th ree letters

fi rst a ut hor/ fi rst t hre e l e t t e rs of se c ond a ut hor, a nd,here required, a sequence number].

ne ar Al k-1-e ne s

Experiment al critical constan ts ar e known for ten lineark-1-enes. The work of Tejas group has extended ourowledge of th e critical pr operties of linear alk-1-enes (R-

efins) t o C12, although n o measurements ha ve been madeC11. The a l k-1-e ne s a re e t he ne (e t hyl ene ), prope ne

ropylene), but -1-ene, pent -1-ene, hex-1-ene, hept -1-ene,-1-ene, non-1-ene, dec-1-ene, an d dodec-1-ene. The firste linear alk-1-enes are stable at their critical point, but

e heavier ones are progressively more un stable.

Eth en e. Ethene (ethylene) is distinguished by havingcritical properties measu red first by J . D. van der Waals

880-van ]. Although th e critical temper atu re reported byn d er W aa l s, 9 . 2 C, i s e s s en t i a ll y t h e s a m e a s t h e

commended value, 9.19 C, it took nearly 100 years fora t value to be u niversally accepted.

The disagreement on th e critical tempera tur e of ethenes o m e e x t en t r e su l t ed fr om t h e w or k of M a a s s a n d

llaborat ors in the 1930s. They postulated th at liquidrsi st s a bove t he t e mpe ra t ure a t whi c h t he me ni sc usa p pe a r s. As l a te a s 1 94 8 [4 8-m a s /m a a ] t h e y w er e

guing that maximum opalescence for ethene occurs at20 C, while t he critical t emperatu re (defined from thelection of the pV isotherm ) is 9.90 C. Today, as n otedpa rt 1 of this series [95-amb/you], i t is u sual to prefer

the view of Kudchadker e t al. [68-kud/ a l a ] t ha t (a ) t heinflection point on the pV i sot he rm a nd t he t e mpe ra t ureof t h e d is a p pe a r a n ce of t h e m e n is cu s a r e e ss en t i a lly

identical, and (b) it is pr efera ble to determ ine th e criticaltemperat ure visually.

Ethene a lso has the distinction that tw o IUPAC volumes

[74-an g/ar m, 88-jac/jah] ha ve been devoted to its pr operties.Consi dera bl e work wa s done be t we e n 1974 a nd 1988,primarily in recognition of the commercial importance of

e t he ne , but a l so owing t o t he fa ct t ha t cust ody t ra nsfertakes place at conditions close to its critical point.

The most careful determinat ion of the critical tempera -ture of ethene was probably that of Moldover [74-mol], whoused the m eniscus disappearan ce method. For the critical

density, Moldover filled four a mpu les to den sities close tothe literature value for Fc. He t he n me a sure d t he he ightat which the meniscus disappeared at Tc, and then by using

a n i nt e gra t e d form of t h e cri t ica l i sot he rm e qua t ion hefou n d t h e d en s it y ()Fc) a t w h ich t h e m e n is cu s w ou l ddisappear exactly in the center of the ampule.

Moldover measured tc ) (9.194 ( 0.004) C and Fc )(0.2146 ( 0.0006) gcm -3. In a ddi t i on, he i nt e rpol a t e d

t he t he n unpubl i she d pV T da t a of Ha st i ngs a nd Le ve l tSengers [77-has/lev, 80-has/lev] to determine the value ofthe critical pressure as pc ) (5.039 ( 0.010) MPa.

Hastings a nd Levelt Sengers later comment ed [80-has/

lev] th at t heir ear lier r esults u sed by Moldover were foun dto be slightly in error.

The 1988 IUPAC volume [88-jac/jah] accepted Moldovers

tc and redetermined pc a n d Fc from the pV T dat a of Douslinand Harrison [76-dou/har] and Hastings and Levelt Sen-gers [80-ha s/lev]. In ad dition, J acobsen et al. [88-jac/jah ]

reported th e values u sed in their critical-region equat ionand in th e main equation of state. The latter values (seeTable 2), which correspond to th e inflection point on t he

critical pV isotherm, are outside of the error limits Jacobsen

et al. set for the selected values. Our r ecommendationsare consistent with th ese selected values, but are slightlyrounded off and have larger u ncertainties: Tc ) (282.34 (

64 5 J. Chem. Eng. Data 1996, 41 , 64 5-65 6

S0021-9568(95)00199-3 CCC: $12.00 1996 Amer ican Ch emical Society


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02) K, pc ) (5.041 ( 0.004) MPa, a nd Fc ) (0.214 ( 0.002)cm -3.

P r open e. Next to ethene, propene (propylene) is theost importa nt a lkene in commerce. However, the numberinvestigations of the critical constan ts of propene is onlyma ll fraction of the investigations on ethene. Fur ther-

ore, t he cri t ica l const a nt s of prope ne a re subje ct t onsiderable uncertainty.

Angus et al. , in the IUPAC monograph on propene [80-g/arm ], examined six investigations [15-sei/bur , 21-maa/i, 33-win/maa, 40-vau/gra, 41-lu/new, 49-mar/pre] andncluded that It is not possible to have complete confi-n ce i n a n y of t h e m . An g u s et al. s u g ge st t h a t Tcobably lies in the region (365.15 ( 0.5) K, pc lies between

5 and 5) MPa, and Fc is not known. Because of thesecertainties, Angus et al. di d not c onst ra i n t he i r pV Tuation to go through a certa in critical point, but insteadtermined the following critical constan ts by satisfyinge critical point criteria, (p/F)T ) 0 a n d (2p/F2)T ) 0:) 365.57 K, pc ) 4.6646 MPa, an d Fc ) 0.005 31 molcm -3

223 gcm -3). Angus added that t heir value for Tc m a yas much as 0.5 K too high, but still used their values

or the sake of thermodynamic consistency.

Brun ners [88-bru] careful visual observation, the pV Teasur ements of Ohgaki et al. [90-ohg/um e], an d th e very

cent results of Wilson et al. [95-wil/wil] have confirmednguss su pposition th at their Tc recommen dation [80-ang/m ] is too high. Ohgaki et al. ma de t he i r me a sure me nt sthe critical region (0.996 < Tr < 1.004; 0.6 < Fr < 1.4)d converted t hem to critical pr operties with the power

w for the vapor -liquid coexistence curve and the p-Fation on t he critical isotherm (see 96-amb/you for a

rre ct i on t o pa rt 1 of t hi s se ri es). Consi deri ng a l l t heperimenta l measurement s tha t ar e listed in Table 2, we

commend the following critical constants for propene: Tc(364.9 ( 0.4) K, pc ) (4.60 ( 0.03) MPa, an d Fc ) (0.2280.005) gcm -3. Although the u ncerta inties for Tc a n d pce larger than is desirable for a substance as important

as pr opene, they ar e not large enough to include the 1980IUPAC recommendations [80-ang/arm].

C4 t o C6 Alk-1-enes. Appa re nt l y, no e xpe rime nt a li nve st iga t ion ha s be en ma de on but -1-e ne si nce 1950.Fortunately, this 45-year old investigation was made byBeatt ies group [50-bea/mar], and t hu s th e slightly roun ded-off 1950 results can be recommended with confidence.

More recent data have been reported for pent-1-ene andsome of the higher alk-1-enes by the groups of Ambrose(C5 t o C8), Kay (C5 a n d C6), Ma (C5 a n d C6), and Teja (C5

t o C10, C12). In the case of pent-1-ene, ther e is excellenta gre e me nt i n t he Tc between Ambrose [60-amb/cox] andTeja [91-gud/ros]. In view of this agreement, i t appearstha t a 1972 result from Kays group [72-mou/kay] is 1 Ktoo low, while a m ore recent Ch inese investigation [91-ma/ma ] i s 1 K t oo high. For pc we recommend the value ofWolfe et al. [83-wol/kay], wh ile for Fc we a ve ra ge d t heresu lts of Wolfe et al., Ma et al. [91-ma/ma], and Gude etal . [91-gud/ros].

The modern measurements for hex-1-ene are in goodagreement for Tc a n d pc, but there is a significant differencefor Fc, for whi c h we re c omme nd t he a ve ra ge of t he t woavailable data [91-gud/ros, 91-ma/ma].

C7 t o C12 Alk-1-enes . Th e C7 a nd hi ghe r a l ke ne s a re

therm ally unstable at th eir critical points, an d th is insta-bility increases as t he carbon num ber increases. It is forsuch unsta ble compounds t hat Ambrose had to use a r apidheater in order to reduce the effect of thermal decomposi-tion, while Tejas group developed their special methods[see 95-amb/you and 95-amb/tso].

For h ept-1-ene, there is very good agreement in the Tcresu lts of Ambr ose et al. [60-amb/cox] an d Gude et al. [91-gud/ros], but we only have Gu des r esults for pc a n d Fc. Inthe latter case, the value of Gude et al. was rounded down,in accord with our comment in Table 2 that their resultsfor p ent-1-ene an d hex-1-ene m ay be t oo high; see also 93-ste/chi.

b l e 1 . R e c o m m e n d e d V a l u e s o f C r i ti c a l P r o p e r t i e s o f U n s a t u r a t e d A l i p h a t i c H y d r o c a r b o n s

molar m assM/gm ol-1 a Tc/Kb (() pc /MP a (() Fc/gcm -3 (()

Vc/cm 3m ol-1 Zcc

hen e 28.053 76 282.34 (0.02) 5.041 (0.004) 0.214 (0.002) 131.1 0.2815r open e 42.080 64 364.9 (0.4) 4.60 (0.03) 0.228 (0.005) 184.6 0.2798u t -1-en e 56.107 52 4 19.5 (0.5) 4.02 (0.05) 0.233 (0.012) 240.8 0.2775en t -1-ene 70.134 4 464.8 (0.5) 3.56 (0.05) 0.235 (0.005) 298.4 0.275ex-1-en e 84.161 28 5 04.0 (0.3) 3.21 (0.03) 0.237 (0.005) 355.1 0.272ept -1-ene 98.188 16 537.3 (0.4) 2.92 (0.04) 0.24 (0.01) 409 0.267ct -1-en e 112.215 04 567.0 (0.8) 2.68 (0.08) 0.24 (0.01) 468 0.266on -1-en e 126.241 92 594.0 (1.0) 0.24 (0.01) 526ec-1-en e 140.268 8 617 (2) 2.22 (0.10) 0.24 (0.01) 584 0.253odec-1-en e 168.322 56 658 (2) 1.93 (0.20)

Z)-bu t -2-en e 56.107 52 435.5 (0.1) 4.21 (0.05) 0.240 (0.010) 233.8 0.272E)-bu t -2-en e 56.107 52 428.6 (0.1) 4.10 (0.02) 0.236 (0.005) 237.7 0.2735m et h ylpr open e 56.107 52 417.9 (0.1) 4.000 (0.010) 0.235 (0.004) 238.8 0.2749

Z)-pen t -2-ene 70.134 4 475 (1) 3.69 (0.10)m et h ylbu t -1-en e 70.134 4 452.7 (0.3) 3.53 (0.03) 0.230 (0.010) 304.9 0.286m et h ylbu t -2-en e 70.134 4 470 (1) 3.42 (0.10)

yclopen t en e 68.118 52 506.5 (0.5) 4.80 (0.05) 0.278 (0.010) 245 0.279ycloh exen e 82.145 4 560.4 (0.1)r opa dien e 40.064 76 394 (?) 5.25 (?)u t a -1,3-dien e 54.091 64 425 (1) 4.32 (0.10) 0.245 (0.010) 221 0.270exa -1,5-diene 82.145 4 508 (?)

+)-(R )-p-m en t h a -1,8-dien e 136.237 04 653 (2) 0.29 (0.01) 470-)-(1S )-pin -2-en e 136.237 04 644 (2) 0.30 (0.01) 454+)-ca r -3-en e 136.237 04 658 (2) 0.28 (0.01) 487

hyn e 26.037 88 308.3 (0.1) 6.138 (0.010) 0.232 (0.004) 112.2 0.2687r opyn e 40.064 76 402.4 (0.2) 5.63 (0.02) 0.245 (0.005) 163.5 0.275u t -1-yn e 54.091 64 440 (2) 4.60 (0.20) 0.26 (0.03) 208 0.262

a Molar masses based on carbon ) 12.011, hydrogen ) 1.00794. b Temperatures are expressed in ITS-90. c Zc ) pcVc/R Tc where R )14 51 J m ol-1K-1.

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b l e 2 . C r i t ic a l P r o p e r t i e s f r o m t h e L i t e r a t u r e

yearvalues reported innonstandard units T90/K p/MPa F/gcm -3 method a authors

ETHENE (Ethylene): molar ma ss ) 28.053 76 g; CASRN ) 74-85-1

T68 - T48 ) -0.004 K; T90 - T68 ) -0.002 K; T90 - T48 ) -0.006 K at 282 K80-va n 9.2 C, 58 a t m 282.4 5.88 1 va n der Wa a ls8 2-s a r 1 .5 C , 4 3.5 a t m ,

0.006 739 Amagat(volume)

274.5 4.41 0.186 8 Sa r r a u

82-ca i 13 C 286 1 Ca illetet84-dew 10.1 C, 51.0 a t m 283.2 5.17 1 Dewa r86-ca i/m a t 12.5 C 285.6 0.21 1, 7 Ca illetet a n d Ma t h ia s95-ols 10 C, 51.7 a t m 283 5.24 1, 5 Olszewski

97-vil 10 C 283 1 Villa r d-ca r /a r n (9 .5 0 ( 0.10) C,

(50.65 ( 0.10) at m282.6 5.132 1a Ca r doso a nd Ar n i

-m a a /w r i (9 .9 ( 0.2) C 283.0 1 Ma a ss a n d Wr igh t-mat/cro,29-mat/cro

(282.6) 0.21597 7 Ma th ia s et al.

-br i 9.0 C, 52.0 a t m 282.2 5.27 3 Br it t on-m a a /ge d (9 .5 0 ( 0.01) C,

(49.98 ( 0.01) at m282.64 5.064 0.2374 ( 0.0067 1, 7 Ma ass a nd Geddes

-m ci/m a a 9.50 C 282.64 1 McIn t osh a n d Ma a ss-dac/mci,39-mci/dac

(9.90 ( 0.01) C,(50.50 ( 0.01) atm ,4.40 cm 3g-1

283.04 5.117 0.227 3 Da cey et al.,McIntosh et al.

-n a l/m a a (9 .2 1 ( 0.015) C 282.35 1a Na ldr et t a n d Ma a ss-ka y 48.65 F , 735.6 psi 282.39 5.072 1a Ka y-w h i/m a s (9 .2 6 ( 0.01) C 282.40 0.2095 ( 0.0004 1a , 3 Wh it ewa y a n d Ma son-r ow/su t 9.4 C, 49.84 a t m 282.54 5.050 1a Rowlin son et al.

-sh i/koh 9.54 C, 50.53 a t m 282.68 5.120 1 Sh im a n d Koh n-va s 4.69 cm 3g-1 283.05 5.100 0.213 5, 7, 10 Va sh ch en ko et al.-z er /k og 1 23 .6 cm 3m ol-1 282.318 4.96 0.2270 1a Zer n ov et al.-a n g/a r m 282.65 ( 0.25 5.076 ( 0.02 0.218 ( 0.002 7, 10 An gu s et al.-m ol (9.194 ( 0.004) C 282.342 0.2146 ( 0.0006 1 Moldover-ben 282.648 5.075 0.215 8 Ben der-d ou /h a r 7 .6 35 m oldm -3 282.35 5.0420 0.2142 3 Dou slin a n d H a r r ison-t r a /w a s (9 .3 0 ( 0.05) C,

(170.6 ( 1.0) Amagat282.45 0.2152 ( 0.0013 3 Tr a ppen ier s et al.

-goo 7.6 m oldm -3 282.35 5.04234 0.21 ? Goodwin-h a s /l ev (9 .1 34 ( 0.043) C 282.282 5.0336 ( 0.0048 3 H a st in gs a nd

Levelt-Sengers-h a s /l ev (7 .6 34 0 ( 0.0009)

m oldm -3282.3432 ( 0.0017 5.0403 ( 0 .0 00 2 0 .2 14 16 ( 0.00003 3, 8 H ast in gs et al.

-t h o/z a n (9 .2 2 ( 0.02) C 282.368 1 Th om a s a n d Za n der-m c c/ja c 7 .6 34 0 m oldm -3 282.341 5.0403 0.21416 8 McCa r t y a n d J a cobsen-syc/va s 282.348 ( 0.05 5.042 ( 0.002 0.2142 ( 0.0005 8 Sych ev et al.

-you 7.650 m oldm -3 282.341 5.0404 0.2146 8 You n glove-n e h/h a l (7 .6 35 ( 0.006)

m oldm -3282.348 ( 0 .0 10 5 5 .0 41 97 ( 0.0026 0.2142 8 Neh za t et al.

-jah,86-jah/jac

7.634 moldm -3 282.343 5.0401 0.2142 8 J a h a n gir i,J a h a n g ir i et al.

-br u 282.33 ( 0.1 5.055 ( 0.005 2a Br u n n er-va n /ja c see n otes 7 Va n P oolen et al.-ja c/ja h select ed va lu es 282.342 ( 0 .0 04 5 .0 408 ( 0 .0 00 8 0 .2 14 2 ( 0.0004 8 J acobsen et al.

cr it ica l r egion E OS 282.343 5.0403 0.2142main EOS (7.689 14

m oldm -3)282.318 5.0373 0.215709

r e com m e nd ed v al u es 2 82 .3 4 ( 0.02 5.041 ( 0.004 0.214 ( 0.002

Sarr au [1882-sar ] determined t he critical consta nts by fitting Amagat s pV T data with the equation of state of Clausius. Since heassumed tha t t he absolute t emperature is 273.00 + t/C, Sa rr au s Tc should be 274.5 K (and tc ) 1.35 C). Kobe an d Lynn[53-kob/lyn] report the critical density incorrectly as 0.148 gcm -3.

Dewar [1884-dew] notes t hat the da ta for eth ylene are n ot new, but Dewars values could not be found in an 1884 or ea rlier paper.Cailletet a nd Mat hias [1886-cai/mat ] report 12 C and 0.22 gcm -3 in the text, but the values interpolated from their graph

are 12.5 C an d 0.21 gcm -3.Mathias et al. [27-, 29-mat/cro] determined Fc a t t h e tc of Maass and Wright [21-maa /wri]; at 9.19 C, Fc would have been 0.216 16

gcm -3.Whiteway and Mason [53-whi/mas ] used a vertical Pyrex bomb whose contents were vigorously stirr ed. However, no stirrin g was

used in determining Fc.F. Din (Thermodynam ic Functions of Gases, Vol. 2, Butt erworths, London, 1962) selected th e Tc a n d Fc of Maass and Geddes

[37-maa/ged] and t he Fc of Mathias et al. [29-mat/cro] extrapolated to 9.5 C.Vashchenko et al. [71-vas] took Tc from the literature and determined pc by graphically extrapolating their vapor pressure data;

Fc by extrapolating the rectilinear diameter.Angus et al. [74-ang/arm] took Tc a n d pc from the literature (after some analysis) and determined Fc by extrapolating

the rectilinear diameter of Mathias et al. [27-ma t/cro].Bender [75-ben] selected the critical dat a a nd constrained his equat ion of state to these values and the criticality conditions.

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bl e 2 ( c o n ti n u e d )

ychev et al. [81-syc/vas] may have selected the critical constants from the literature and constrained their equation of stateto these values and the criticality conditions. The pc a n d Fc uncerta inties ar e th ose on p 37; different values a re given on p 113.

Nehzat et al. [83-neh/hal] correlat ed th e dat a of Douslin a nd H arr ison [76-dou/har ] and a dopted their values, but providedestimates for the uncertainties (on p 205).

h e Tc a n d pc values in 85-bru are also reported by E. Brunner (J. Chem . Thermodyn . 1987, 19 , 823-835; 1988, 20 , 1397-1409).Van Poolen et al. [86-van/jac] determined Fc a t t h e Tc of Jahangiri et al. [86-jah/jac] by straight rectilinear diameter (7.624 moldm -3

or 0.2139 gcm -3), by rectilinear diameter with a hook (7.639 or 0.2143), and by the critical liquid mole fraction (7.633 or 0.2141).


PROPE NE (Propylene): molar m ass 42.080 64 g; CASRN 115-07-1

T68 - T48 ) -0.002 K; T90 - T68 ) -0.024 K; T90 - T48 ) -0.026 K at 365 K882-n a d 90 C 363 1 N a dezh din

883-n a d 91.6 C 364.8 1 Na dezh din

5-sei/bu r 92.6 C, 34 463 m m H g 365.8 4.5947 1 Seiber t a n d Bu r r ell1-m a a /w r i (9 2.1 ( 0.2) C 365.2 1 Ma a ss a n d Wr igh t

3-win /m a a 92 365 0.225 1, 7 Win kler a n d Ma a ss0-gil/sch 203 F , 675 psi 368 4.654 1(?) Gillila n d a n d Sch eeline

0-s ou 91.9 C , 44.6 a t m,179.7 cm 3m ol-1

365.0 4.519 0.234 10 Sou der s

0-v a u /g r a 9 1. 4 C, 4 5. 4 a tm ,180 cm 3m ol-1

364.6 4.600 0.233 1, 3, 7 Va u gh a n a n d Gr a ves

1-lu /new 92.1 C, 45.4 a t m 365.2 4.600 1 Lu et al.3-cr a (364.6) 0.2277 7 Cr a goe

9-fa r /sa g 1 97 .0 F , 6 68 p s i,0.06944 ft 3lb -1

364.8 4.606 0.2307 5, 7, 10 F a r r in gt on a n d Sa ge

9-m a r /p r e (9 1.7 6 ( 0.015) C,(45.61 ( 0.02) atm ,

(0.191 ( 1%) Lm ol-1

364.88 4.6214 0.220 3 Ma r ch m a n et al.

5-kr e 92.05 C 365.17 1 Kr eglewski1-va s 4.34 cm 3g-1 365.03 4.64 0.230 5, 7, 10 Va sh ch en ko et al.

5-ben 364.88 4.613 0.227 8 Ben der8-ju z/sif 364.96 4.60 0.230 5, 8 J u za et al.

0-a n g /a r m 0 .0 05 3 1 m olcm -3 365.55 4.6646 0.223 8 An gu s et al.

8-br u 364.83 ( 0.2 4.600 ( 0.02 2a B r u n n er0-ohg/ume 0.005 55 molcm -3 364.57 4.579 0.2335 3 Oh ga ki et al.

5-wil/wil 365.16 ( 0.05 4.594 ( 0.005 2c Wilson et al.

r ecom m en de d va lu es 3 64.9 ( 0.4 4.60 ( 0.03 0.228 ( 0.005

Nadehzdin reported the tc as 90 C in 1882-nad an d 91.6 C in 1883-nad, which is the average of two values r eported ear lier inthe paper: 90.2 C and 93 C. The Germa n su mma ry [1883-nad-1] gives the value 97 C, but no such value could be foundin the original papers.

Winkler and Maass [33-win/maa] measured the saturated vapor and liquid densities up to 91.6 C. Critical temperature anddensity were estimated from their Figure 1.

ouders [40-sou] is quoted in 40-vau/gra a s h aving critically chosen the critical const ant s.ragoe [43-cra] deter mined Fc a t t h e Tc (and pc) of Vaugha n and Graves [40-vau/gra].arrington and Sage [49-far/sag] determined their tc from a review of available data and pc by extrapolating their vapor

pressure data from 190 F to tc.

Vashchenko et al. [71-vas] took Tc from the literature and determined pc by graphically extrapolating their vapor pressured a ta a n d Fc by extrapolating the rectilinear diameter.

ender [75-ben] selected the critical data and constrained his equation of state to these values and the criticality conditions.u z a et al. [78-juz/sif] claim t hat their equation of stat e is valid from 180 K to 460 K, but a lso report a Tc a n d Fc; their vapor pressure

equation was extrapolated from 360 K to Tc.h e Tc of Ohgaki et al. [90-ohg/ume] is presum ed t o be consistent with t he IP TS-68 scale.

Wilson et al. [95-wil/wil] made t heir mea surem ents with both a sta tic and a flow method that employed a visual cell. There was n ostatistical difference between the values measured by the two methods.

y ea r va l ue s r e por t e d i n n on s t a n da r d u n it s T90/K p/MPa Fc/gcm -3 method a authors

BUT-1-ENE: molar m ass 56.107 52 g; CASRN 106-98-9

T68 - T48 ) 0.0019 K; T90 - T68 ) -0.035 K; T90 - T48 ) -0.016 K at 420 K8-cof/m a a 144 C 417 1 Coffin a n d Ma a ss3-cr a 39.2 a t m (417) 3.97 0.2354 6, 7 Cr a goe

6-old/sag 297 F, 588 psi, 3.85 ft3lbmol-1 420 4.05 0.2334 3 Olds et al.0-b ea /m a r (1 46 .4 ( 0.3) C, (39.7 ( 0.3) atm,

(4.15 ( 5%) molL-1419.53 4.023 0.233 3 Bea t t ie a n d Ma r ple

r ecom m en ded va lu es 419.5 ( 0.5 4.02 ( 0 .0 5 0 .2 33 ( 0.012

Cragoe [43-cra] determ ined t he Fc a t t h e Tc of Coffin a nd Ma ass [28-cof/maa]. He a lso estimat ed pc by extrapolating availablevapor pressure da ta.

Beattie and Marple [50-bea/mar] reported the uncertainty in Tc as 0.3 C on pp 1450 and 1452, but as 0.03 C on p 1451(caption for Figure 2).



5/12


ye a r va l u es r e por t e d i n n on s t a n da r d u n it s T90/K p/MPa F/gcm -3 method a authors

PEN T-1-ENE: molar m ass 70.1344 g; CASRN 109-67-1

T68 - T48 ) 0.039 K; T90 - T68 ) -0.040 K; T90 - T48 ) -0.001 K at 465 K83-pa w 201.0 C 474.2 1 P a wlewski93-a lt 208.0 C 481.2 1 Altsch u l95-pic 201.2 C 474.4 1 P ict et95-pic/a lt 201.0 C 474.2 1 P ict et a n d Alt sch u l-ves 202.6 C, 40.4 a t m 475.8 4.094 1 Vespign a n i-da y/nic 201 C, 30 700 m m H g 474 4.093 3, 5 Da y et al.-a mb/cox (191.59 ( 0.03) C 464.74 1 Am br ose et al.-m ou /ka y 515.03 psi 463.73 3.551 1a Mousa et al.

-wol/ka y 465.1 3.55 0.233 1a , 7 Wolfe et al.-gu d/r os 464.7 ( 0.3 0.239 ( 0.005 1c Gu de et al.-m a /m a (192.59 ( 0.17) C 465.70 3.592 ( 0 .0 26 0 .2 33 4 ( 0.0009 1, 7 Ma et al.

r ecom men ded va lu es 464.8 ( 0 .5 3.56 ( 0.05 0.235 ( 0.005

awlewski [1883-paw] measur ed th e tc of amylene; however, he also reported the tb ) 38 C, which is close to that of 2-methylbut-2-ene (38.55 C).

Altschul [1893-alt] also measur ed th e tc of amylene; see previous note.ictet et al. [1895-pic, 1895-pic/alt] reported the tc of pent al, which ma y be 2-meth yl-2-buten e. However, the compound is given

as pent-1-ene in 23-lan/boe and 53-kob/lyn.espignani [03-ves] identified his sample as amilene-n; however, h e r eported a tb (37.5 C at 761.5 mm Hg) that is close to th at of

2-meth ylbut-2-ene or of the t wo but-2-enes, (36 to 37) C. On t he other han d, the reported densit y (0.6360 gcm -3 at 21/4 C) iscloser to t hat of pent-1-ene.

a y et al. [48-day/nic] mention that tc is in th e neighborhood of 201 C and add tha t t he critical region will be considered in a futurepaper, but such a paper could not be located. They measured the vapor pressure up to 200 C. We calculated pc with theirequat ion for t he (170 to 200) C ra nge. (The 10-3 in the last term of the equation should be 10-9.)

Ma et al. [91-ma/ma] report 192.59 C in Tables 4 and 8, but 192.42 C in Table 9.

y ea r va l ue s r e por t e d i n n on s t a nd a r d u n it s T90/K p/MPa F/gcm -3 method a authors

HE X-1-ENE: molar m ass 84.161 28 g; CASRN 592-41-6

T68 - T48 ) 0.055 K; T90 - T68 ) -0.040 K; T90 - T48 ) 0.015 K at 504 K893-a lt 243.5 C (?) 516.6 1 Alt sch u l0-a mb/cox (230.83 ( 0.03) C 504.00 1 Am br ose et al.4-ka y/you 503.2 ( 0 .1 3 .2 12 ( 0.002 1a Ka y a n d You n g

-gu d/r os 504.2 3.206 ( 0.02 0.242 ( 0.005 1c Gu de et al.-m a /m a (230.57 ( 0.25) C 503.68 3.200 ( 0 .0 30 0 .2 32 0 ( 0.0009 1, 7 Ma et al.

4-gu d/t ej ga s fu r n a ce 504.2 ( 0.2 0.241 ( 0.005 1c Gu de a n d Tejapla t in um fu r n a ce 504.0 ( 0.3 0.242 ( 0.03flow m eth od 504.8 ( 0 .8 3 .2 06 ( 0.02

r ecom men ded va lu es 504.0 ( 0.3 3.21 ( 0.03 0.237 ( 0.005

Altschul [1893-alt] r eported the tc

of hexylene with a question mark; he noted that the liquid became brown and the temperaturestarted increasing.

Kay an d Young [74-kay/you] reported t he u npublished da ta of W. B. Kay an d S. P ak, API Critical Properties of HydrocarbonMixtures, Progress Report No. 5, 1970 -71.

Gude et al. [91-gud/ros] measured (504.0 ( 0.3) K with th e sealed am pule met hod and (504.8 ( 0.8) K with the flow method.In 94-gud/tej, gas furna ce and platinu m furn ace refer to th e sta tic (sealed ampule) meth od.

ye a r v al u es r e por t e d i n n on s t a n da r d u n it s T90/K p/MPa F/gcm -3 method a authors

HEP T-1-ENE: molar m ass 98.188 16 g; CASRN 592-76-7

T68 - T48 ) 0.064 K; T90 - T68 ) -0.040 K; T90 - T48 ) 0.024 K at 537 K0-a m b/cox (264.08 ( 0.05) C 537.25 1c Am br ose et al.1-gu d/r os 537.4 2.921 ( 0.02 0.244 ( 0.005 1c Gu de et al.


Ambrose et al. [60-amb/cox] measured Tc in a rapid heater; the rate of change of the apparent Tc wa s +0.5 Kh -1.Gude et al. [91-gud/ros] measured (537.4 ( 0.3) K with t he sealed a mpule m ethod and (537.6 ( 0.8) K with the flow method;

537.4 K is their recommen dation. Because their Fc values for pent-1-ene and hex-1-ene were higher than other literaturevalues, their results for C 7+ (which are unstable at the critical point) have been adjusted to lower values with one lesssignificant figure.

ye a r v al u es r e por t e d i n n on s t a n da r d u n it s T90/K p/MPa F/gcm -3 method a authors

OCT-1-ENE : molar m ass 112.215 04 g; CASRN 111-66-0883-pa w 298.6 C 571.8 1 P a wlewski893-a lt 304.8 C 578.0 1 Alt sch u l0-a m b/cox (293.4 ( 0.1) C 566.6 1c Am br ose et al.0-sm i/n eg 569.8 ( 1 0.270 1c Sm it h et al.1-gu d/r os 567.4 2.675 ( 0.02 0.242 ( 0.005 1c Gu de et al.




6/12


Ambrose et al. [60-amb/cox] measured Tc in a rapid heater; the rate of change of the a pparent Tc wa s +3.0 Kh -1.mith et al. [90-smi/neg] noted t hat their Tc was the first point observed, and therefore the accuracy would not be better than (1 K.

Their Fc is clearly an approximate value.Gude et al. [91-gud/ros] measured (567.3 ( 0.3) K with th e sealed am pule meth od and (567.8 ( 0.8) K with the flow method;

567.4 K is their recommendat ion. See also note for Gude et al. under hept-1-ene.

ye ar va lu es r ep or t ed in n on st a n da r d u n it s T90/K p/MPa F/gcm -3 method a authors

NON-1-ENE: molar m ass 126.241 92 g; CASRN 124-11-81-gu d/r os 593.7 ( 0.3 0.241 ( 0.005 1c Gu de et al.

r ecom m en ded va lu es 594.0 ( 1.0 0.24 ( 0.01

Gude et al. [91-gud/ros] measured Tc only with the sealed ampule method. See also note for Gude et al. under hept-1-ene.

y ea r va l ue s r e por t e d i n n on s t a n da r d u n it s T90/K p/MPa F/gcm -3 method a authors

DEC-1-ENE : molar m ass 140.2688 g; CASRN 872-05-91-gu d/r os 616.4 2.218 ( 0.02 0.240 ( 0.005 1c Gu de et al.4-gu d/t ej ga s fu r n a ce 617.2 ( 1.1 0.239 ( 0.005 1c Gu de a n d Teja

pla t in u m fu r n a ce 616.9 ( 1.2 0.240 ( 0.003flow m et h od 616.0 ( 0.8 2.218 ( 0.02

r ecom men ded va lu es 617 ( 2 2.22 ( 0.10 0.24 ( 0.01

Gude et al. [91-gud/ros] measured (616.9 ( 1.2) K with t he sealed a mpule m ethod and (616.0 ( 0.8) K with the flow method; 616.4 Kis their recommendat ion. See also note for Gude et al. under h ept-1-ene.

n 94-gud/tej, gas furna ce and platinu m furn ace refer to th e sta tic (sealed ampule) meth od.

ye ar va lu es r ep or t ed in n on st a n da r d u n it s T90/K p/MPa F/gcm -3 method a authors

DODEC-1-ENE: molar m ass 168.322 56 g; CASRN 112-41-4

1-gu d/r os 657.6 ( 0.9 1.930 ( 0.02 1c Gu de et al.r ecom m ended va lues 658 ( 2 1.93 ( 0.20

Gude et al. [91-gud/ros] measured Tc only with the flow method.

y ea r v al u es r e por t e d i n n on s t a n da r d u n it s T90/K p/MPa F/gcm -3 method a authors

(Z)-BUT-2-ENE (cis -But-2-ene): molar ma ss 56.107 52 g; CASRN 590-18-1

T68 - T48 ) 0.026 K; T90 - T68 ) -0.037 K; T90 - T48 ) -0.011 K at 436 K8-cof/m a a 155 C 428 1 Coffin a n d Ma a ss3-cr a (320 F ), 41.5 a t m (433) 4.205 0.2398 6, 7, 9 Cr a goe0-a mb/cox (162.40 ( 0.02) C 435.54 1 Am br ose et al.

r ecom m en ded va lu es 435.5 ( 0.1 4.21 ( 0 .0 5 0.24 0 ( 0.010

Coffin and Maass [28-cof/maa] prepared a -butylene sample, a m ixture of (Z)- and (E)-but-2-enes; see text.Cragoe [43-cra] estima ted tc and then determined pc by extrapolating literature vapor-pressure data.


(E)-BUT-2-ENE (trans-But-2-ene): molar m ass 56.107 52 g; CASRN 624-64-6

T68 - T48 ) 0.024 K; T90 - T68 ) -0.037 K; T90 - T48 ) -0.013 K at 429 K8-cof/m a a 155 C 428 1 Coffin a n d Ma a ss3-cr a (311 F ), 40.5 a t m (428) 4.104 0.2359 6, 7, 9 Cr a goe0-a mb/cox (155.46 ( 0.02) C 428.60 1 Am br ose et al.

r ecom m en ded va lu es 428.6 ( 0.1 4.10 ( 0 .0 2 0.23 6 ( 0.005

Coffin and Maass [28-cof/maa] prepared a -butylene sample, a m ixture of (Z)- and (E)-but-2-enes; see text.Cragoe [43-cra] estima ted tc and then determined pc by extrapolating literature vapor pressure data.


2-METHYLPROPE NE (Isobutylen e): molar m ass 56.107 52 g; CASRN 115-11-7

T68 - T48 ) 0.018 K; T90 - T68 ) -0.034 K; T90 - T48 ) -0.016 K at 418 K83-n a d, -n a d-1 150.7 C 423.8 1 Na dezh din , Na dejdin e (sic)-cof/m a a , 28-cof/m a a 143.5 C 416.6 1 C offin a n d Ma a ss-sch /gil (300 ( 2) F, (583 ( 4) psi 422 4.02 1 Sch eelin e a n d Gillila n d-bea /in g (144.73 ( 0.05) C,

(39.48 ( 0.05) at m417.86 4.000 0.234 ( 0.002 3 Bea t t ie et al.

-ben (144.6 ( 0.6) C,(39.5 ( 0.2) at m

417.8 4.002 1 Ben edict

-cr a (417.86) 0.2352 7 Cr a goe

r ecom m en de d va lu es 41 7.9 ( 0.1 4.000 ( 0.010 0.235 ( 0.004

Nadezhdins [1883-nad] value for the tc was t he a verage of 11 observations; his n ame was spelled Na dejdine in 1883-nad-1.Coffin and Maass first reported the tc in [27-cof/maa], although the details of their measurements were given in their later paper

[28-cof/maa].



7/12


ye ar va lu es r ep or t ed i n n on st a n da r d u n it s T90/K p/MPa F/gcm -3 method a authors

(Z)-PENT-2-ENE (cis -Pent -2-ene): molar m ass 70.1344 g; CASRN 627-20-3

71-len /r eb 395.2 F , 535 psi 474.9 3.69 1a Len oir et al.

r ecom m en ded va lu es 475 ( 1 3.69 ( 0.10

The critical consta nts were meas ured in a Kay-type phase boundary appa rat us. The sample was 96.3 mol % (Z)- and 3.5 mol %(E)-pent-2-ene; 0.2 mol % of other impurities.

y ea r va l u es r e por t e d i n n on s t a n da r d u n it s T90/K p/MPa F/gcm -3 method a authors

3-METHYLBUT-1-EN E: molar m ass 70.1344 g; CASRN 563-45-1

T68 - T48 ) 0.034 K; T90 - T68 ) -0.039 K; T90 - T48 ) -0.005 K at 452.5 K1-m a /m a (179.54 ( 0.14) C 452.65 3.527 ( 0 .0 25 0 .2 30 0 ( 0.0009 1, 7 Ma et al.


2-METHYLBUT-2-ENE (-Isoamylene): molar m ass 70.1344 g; CASRN 513-35-9

882-zh u , 191.6 C, 33.93 a t m 464.8 3.438 1 Zh u k,

1883-n a d Na dezh din

1-kiy/su z 197.2 C, 33.7 a t m 470.4 3.415 1 Kiya m a et al.

r ecom m en ded va lu es 470 ( 1 3.42 ( 0.10

Zhuk [1882-zhu], Nadezhdins st udent , reported t he da ta for amylene; Nadezhdin [1883-nad] r epeated the tc, but identified thecompound a s isoamylene, which may be a mixtur e of 3-methylbut-1-ene a nd 2-methylbut-2-ene. The reported tc is remarkablyclose to t he m odern value for pen t-1-ene.

Kiyama et al. [51-kiy/suz] also determ ined via their pV T m e a s u r e m en ts th a t tc ) (195 to 200) C. Their sam ple had a tb ) 37.8 C,0.8 deg below the a ccepted value. It sh ould also be noted th at the da ta reported by Kiyamas group [51-kiy/ike] for ethyne a revery poor: 3 K and 0.2 MPa higher t han the r ecommen ded values for Tc a n d pc.

y ea r va l ue s r e por t e d i n n on s t a n da r d u n it s T90/K p/MPa F/gcm -3 method a authors

CYCLOPENTEN E: molar m ass 68.118 52 g; CASRN 142-29-0

T68 - T48 ) 0.055 K; T90 - T68 ) -0.040 K; T90 - T48 ) 0.015 K at 506 K

-a m b/gr a (232.9 ( 0.05) C 506.06 1 Am br ose a n d Gr a n t

0-t ej/a n s 507.6 ( 0.3 0.278 ( 0.005 1c Teja a nd An selm e

0-t ej/r os 507.0 ( 0 .6 4.80 2 ( 0.02 1c Teja a n d Rosen t h a l

r ecom mended va lu es 506.5 ( 0.5 4.80 ( 0.05 0.278 ( 0.010

CYCLOHEXENE : molar m ass 82.1454 g; CASRN 110-83-8

T68 - T48 ) 0.070 K; T90 - T68 ) -0.039 K; T90 - T48 ) 0.031 K at 560 K

0-a m b/cox (287.27 ( 0.02) C 560.45 1 Am br ose et al.

2-ch e/m cc 560.43 1 Ch en g et al.

r ecom men ded va lues 560.4 ( 0.1

Ambrose et al. [60-amb/cox] reported tha t t he compound was only slightly unsta ble (+0.03 Kh -1).


PROP ADIENE (Allene): molar m ass 40.064 76 g; CASRN 463-49-0

5-les/ch a 120.75 C 393.9 1 Lespiea u a n d Cha va n n e

7-st u 51.8 a t m (393.9) 5.25 6 St u ll

r ecom m en ded va lu es 394 ( ? 5.25 ( ?

Stull [47-stu] apparently extrapolated vapor pressure data to the tc of [05-les/cha].

ye a r va lu es r ep or t ed i n n on st a n da r d u n it s T90/K p/MPa F/gcm -3 method a authors

BUTA-1,3-DIENE: molar m ass 54.091 64 g; CASRN 106-99-0

2-ga r /a da 325.7 F 436.3 ? Ga r ner et al.

3-cr a (425.2) 0.2430 7 Cr a goe5-sco/m ey 152 C, 32 420 m m H g 425.2 4.322 0.245 1, 5, 7 Scott et al.

r ecom m en ded va lu es 425 ( 1 4.32 ( 0.10 0.245 ( 0.010

Garner et al. [42-gar/ada] gave private communication for the source of their tc.

Cragoe [43-cra] calculated Fc at t he then unpublished Tc (and pc) of Scott et al. [45-sco/mey].

Scott et al. [45-sco/mey] sta te t hat the t rue critical pressu re ma y be slightly lower than the value th ey give.

ye ar va lu es r ep or t ed i n n on st a n da r d u n it s T90/K p/MPa F/gcm -3 method a authors

HE XA-1,5-DIENE (Diallylene): molar m ass 82.1454 g; CASRN 592-42-7

1883-pa w 234.4 C 507.6 1 P a wlewski

r ecom m en ded va lu es 508 ( ?



8/12

What was said for hept-1-ene can be repeated for oct-1-

e, except that the agreement in Tc is not as good. The

sults of Smith et al. [90-smi/neg] are of lower qu ality: 3

a nd 0. 03 gcm -3 higher than the recommended values

Tc a n d Fc.

Finally, only Gudes measur ements [91-gud/ros] a re

ailable for C9, C10, a n d C12 a l k-1-e ne s. No pc wa seasured for C9, a n d n o Fc for C12.

O the r Al ke ne s

Only the three butenes, cyclopentene, and cyclohexene

have been investigated by several groups, but the critical

pressur e of the two but-2-enes ha s not yet been determined

experimentally. The following compounds have experi-

m e n t a l d a t a : (Z)-but-2-ene (cis-but-2-ene), (E)-but-2-ene

(trans-but-2-ene), 2-methylpropene (isobutylene), (Z)-pent-

2-ene (cis-pent-2-ene), 3-methylbut -1-ene, 2-met hylbut-2-

b l e 2 ( C o n t i n u e d )

ye a r va lu es r ep or t ed in n on st a n da r d u n it s T90/K p/MPa F/gcm -3 method a authors

TERPENES: molar m ass 136.237 04 g

(+)-(R )-p-MENTHA-1,8-DIENE [(+)-D-LIMONENE ]; CASRN 5989-27-590-sm i/n eg 653 ( 2 0.29 ( 0.01 1c Sm it h et al.

(-)-(1S )-PIN -2-ENE : CASRN 7785-26-490-sm i/n eg 644 ( 2 0.30 ( 0.01 1c Sm it h et al.

(+)-CAR-3-ENE: CASRN 13466-78-990-sm i/n eg 658 ( 2 0.28 ( 0.01 1c Sm it h et al.

Lan dolt-Born stein [23-lan /boe] report for tu rpen tin e oil a calculat ed (?) tc attr ibuted to Guldberg (Beibl. An n . Phys. 1883, 7, 350):376.0 C or 649 K, which is in close agreement with t he r esults of Smith et al. [90-smi/neg].

The sam ple of (+)-car-3-ene used by 90-smi/neg was only 92.4% pure. (The ment hadiene a nd pinene sa mples were 99% pure.)


ETH YNE (Acetylene): molar m ass 26.037 88 g; CASRN 74-86-2

T68 - T48 ) -0.010 K; T90 - T68 ) -0.009 K; T90 - T48 ) -0.019 K at 308 K79-a n s 37.05 C, 68 a t m 310.2 6.9 0.36 1, 5, 7 An sdell97-ku e 35.25 C, 61.02 a t m 308.4 6.183 1a Ku en en-m ci 36.5 C, 61.6 a t m 309.6 6.24 0.314 1 McIn t osh-m a t 37.05 C 310.2 0.2306 1, 7 Ma t h ia s-ca r /ba u 35.5 C, 61.6 a t m 308.6 6.24 1 Ca r doso a n d Ba um e-car/bau (35.50 ( 0.10) C, (61.65 ( 0.10) a t m 308.63 6.247 1 Ca r doso a n d Ba um e-kiy/ike 38.5 C, 64.0 a t m 311.6 6.48 3 (?) K iya m a et al.-a mb (35.18 ( 0.05) C 308.31 1 Am br ose-amb/tow 35.18 C, (60.58 ( 01) a t m 308.31 6.138 1 Am br ose a n d Town sen d-k ho 0.1126 Lm ol-1 308.64 0.231 1 Kh odeeva

-gol/kh o 35.20 C 308.32 1 Golobor odko a n d Kh odeeva

r ecom m en ded va lu es 308.3 ( 0.1 6.138 ( 0.010 0.232 ( 0.004

Ansdell [1879-ans] mea sured the vapor pressur e up to 36.9 C (67.96 atm ) and t he liquid density u p to 35.8 C (0.364 gcm -3);his values were r ounded off.

Kobe and Lynn [53-kob/lyn] cite t wo papers by J . Dewar. The first one (Proc. R . S oc. London 1880, 30 , 538-546) is a qua litat iveinvestigation of mixtures of CO2, including the CO2 /acetylene binary. In th e second paper (Philos. M ag . 1884, 18 , 210-216)Dewar reported t he Tc a n d pc values of Ansdell (who investigated ethyne at Dewars su ggestion), but also proposed,by ana logy with CO 2, th a t Fc ) 0.32 gcm -3 rath er than 0.36 gcm -3.

McIntosh [07-mci] determined the Fc by weighing samples a t t he critical point; he concluded t hat he could har dly recommen dhis method.

Cardoso and Bau me [10-car/bau] report four individual m easur ement s ofpc as 61.6 atm, but give the average as 61.5 atm.F. Din (Thermodynam ic Functions of Gases; Butt erworths: London, 1962; Vol. 2) selected t he Tc a n d pc of 12-car/bau and

t h e Fc of 09-mat; th e tc from t he lat ter reference was reported incorrectly as 35.4 C.Khodeeva [66-kho] may only have m easur ed Tc, because the meth od involves filling up a t ube of known volume with a liquid

such that its density has the critical value, and the critical temperature ... is measured.


PROPYNE (Methylacetylene, allylene): molar m ass 40.064 76 g; CASRN 74-99-7

T68 - T48 ) 0.012 K; T90 - T68 ) -0.032 K; T90 - T48 ) -0.020 K at 402 K-les/ch a 129.5 C 402.6 1 Lespiea u a n d Ch a va n n e-m a a /wr i 127.9 C 401.0 1 Ma a ss a nd Wr ight-st u 52.8 a t m (401.0) 5.35 6 St u ll-voh/kan (129.23 ( 0.02) C, (55.54 ( 0.02) a t m 402.36 5.628 0.2449 ( 0.002 3 Voh r a et al.

r ecom m en ded va lu es 402.4 ( 0 .2 5 .6 3 ( 0 .0 2 0 .2 45 ( 0.005

Stull [47-stu] extrapolated vapor pressure data to the tc of [21-ma a/wri].


BUT-1-YNE (Et hylacet ylene): molar m ass 54.091 64 g; CASRN 107-00-695-st e 440 ( 1 4.586 ( 0.10 0.257 ( 0.03 3 St eele

r ecom m en ded va lu es 440 ( 2 4.60 ( 0.20 0.26 ( 0.03

a For methods see Table 3.



9/12

e, cyclopentene, an d cyclohexene.(Z)- a nd (E)-But -2-ene. Coffin and Maass [28-cof/maa]

easu red th e critical tempera tur e of a -butylenesamplea t t he y synt he siz ed. The y re port e d a me lt i ng poi nt127 C) that is between tha t of (Z)-(-138.9 C) and (E)-t -2-ene (-105.57 C), but a normal boiling point (1.0 C)a t is mu ch closer to tha t of (E)-but -2-ene (0.88 C) th ana t of (Z)-but-2-ene (3.72 C).Gershinowitz and Wilson [38-ger/wil] showed that (Z)-t-2-ene is the high-boiling isomer, whereas previouslyha d been t hought t o be the low-boiling isomer. Cragoe

3-cra] identified th e two isomers properly, but Kobe an dnn switched Cragoes result s. However, Kobe and Lynnly made recommendations for the (Z-E) mixture, for

hich they averaged Cragoes estimates for Tc, pc, a nd Fchich Cragoe calculat ed by a pplying the law of rectilinear

ameters).The cri t ica l t e mpe ra t ure of bot h i somers wa s subse-ently measur ed by Ambrose et al. [60-amb/cox], but fore cri t ica l pre ssure we st i ll ha ve onl y Cra goe s 1943timates. In view of the closer agreement of Cragoeslue with Ambroses Tc for (E)-but-2-ene, the pc of this

omer has been assumed to have a lower uncertainty thanat for (Z)-but-2-ene.2-Methylpropene. No experimental measurements have

en reported on the industrially importan t 2-methylpro-ne since 1942, but fortu nately, as in th e case of but-1-e, those measur ements were made by Beatties group2-bea/ing] and were confirmed by Bened ict [42-ben].C5 A l k e n e s . Relatively recent experimental data areailable for (Z)-pent -2-ene [71-len/reb], 3-met hylbut -1-ene1-ma/ma], and 2-methylbut-2-ene [51-kiy/suz]. Addi-

na l da t a on C5 a l ke ne s we re me a sure d from 1882 t o03, but the identity of the C 5 alkenes is unclear. Zhuk

882-zhu] called his sample amylene, but the 1883 paperNadezhdin, Zhu ks professor, and t he Germa n sum mar y

883-nad, -nad-1] called it isoamylene, which is eithermethylbut -1-ene or 2-methylbut -2-ene. Pa wlewski [1883-w] an d Altschul [1893-alt] r eferred to a mylene, wh ichn b e p e n t -1 -e n e (R-n -a m y le n e ) or p e n t -2 -e n e (-n -

mylene), alth ough P awlewskis tb (38 C) is close to that2-methylbut-2-ene (38.55 C). There m ay even be a

est ion about Pictets [1895-pic, -pic/alt] an d Vespigna nis3-ves] samples; see notes in Table 2.The i de nt i t y of t he sa mpl e s use d i n t he 1882 t o 1903ve st iga t ions i s of i nt e rest onl y be ca use more re ce ntviews do not agree on their identificat ion. For example,

be and Lyn n [53-kob/lyn] give th e resu lts of Pawlewski,tschul, Pictet and Altschul, and Vespignani under pent-ene; Vespignan is va lues a re also given for pen t-2-ene;d Nadejdines (sic) results are listed under isoamylene.Also questionable is the diamylene sample used bytschul [1893-alt], which most likely was a mixture of

i som e r s, a n d for t h i s r e a son t h e cr i t ica l t e m pe r a t u r ereported by Altschul, (341 to 342) C, is not included inTables 1 and 2. In a 1943 compilation of physical consta nts[43-dos], Altschuls diamylene was assum ed to be 2,6,6-trimethylhept-2-ene.

Fina lly, th e values r eported by Ambrose [80-am b] for (E)-pent-2-ene, 2-methylbut-1-ene, and 2-methylbut-2-ene areestimates.

C y c l o p e n t e n e a n d C y c l o h e xe n e . Tejas group [90-tej/ans; 90-tej/ros] measu red a significantly h igher criticaltempera tur e for cyclopentene th an Ambrose and Gr ant [57-amb/gra]. On t he other han d, for cyclohexene, which is

slightly un stable at its critical point, t he Tc of Ambrose andGrant has been confirmed by Cheng et al. [62-che/mcc].

Al kadi e ne s

Experimental data have been reported for propadiene,buta -1,3-diene, and hexa-1,5-diene. All three are un stableat their critical points, and only for the commercially veryimportant buta-1,3-diene, which polymerizes rapidly above385 K, do we have a relatively recent determination [45-sco/mey]. Although t here ma y be considerable un certa intyin the critical temperatu re of propadiene [05-les/cha] andhexa-1,5-diene [1883-paw], it should be n oted tha t thecritical temperature reported by Lespieau and Chavanne[05-les/cha] for propyne agrees with the modern value.

T e r p e n e s

Smith et al. [90-smi/neg] measured the critical temper-a t u r e a n d d e n s i t y o f (+)-(R )-p-menth a-1,8-diene [(+)-D-limonene], (-)-(1S )-pin-2-ene, and (+)-car-3-ene. The re-sults m ay be considerably uncertain, because the terpenesa re u nst a bl e a t t h e ir cri t ica l poi nt . I t h a s a l re a dy be ennoted that the results for oct-1-ene reported in the samepaper were of low quality.

A lk y n e s ( Ac e t y l e n e s )

Experimental data could be found in th e open literatu reonly for ethyn e (acetylene) an d p ropyne (meth ylacetylene).In addition, un published data are available for but-1-yne

(ethylacetylene). Calculated values for the critical t em-peratu re of higher a lkynes have been presented by More-house and Maas [31-mor/maa, 34-mor/maa], but it will beshown later that these values are rough estimates.

Eth yn e. Kobe a nd Lynn [53-kob/l yn] re vie wed t hemeasur ements of McIntosh [07-mci], Mathias [09-mat ],Cardoso and Baume [12-car/bau], and Kiyama et al. [51-kiy/ike]. They also presented t he da ta of Ansdell [1879-ans] a nd Kuenen [1897-kue] for historical rea sons. How-ever, Ku enens resu lts, especially for Tc, ar e in excellentagreement with the recommended values.

The recommended values for Tc a n d pc are based on themeasur ements of Ambrose [56-amb, 64-amb/tow]. In thecase of Tc, there is excellent agreement with both more

recent [72-gol/kho] and very old measurements [1897-kue].Eve n t he pc reported in the latter reference is only 0.7%higher than the recommended value.

Ma t hi a s [09-ma t ] me a sure d t he sa t ura t e d l i qui d a ndvapor densities up to 32.93 C and determined the meanof the densities as a function of t: F/gcm -3 ) 0.25431 -0.00064t /C. At the recommen ded tc (35.16 C), this equ a-tion gives Fc ) 0.2318 gcm -3, w h i ch i s t h e v a lu e w erecomm end (rounded off).

P r opyn e. Th e Tcs in the oldest [05-les/cha] and mostrecent sources [62-voh/kan] agree very well, while th eextrapolated value for pc reported by Stull [47-stu] is 5%lower than the only other available value [62-voh/kan].

b l e 3 . K e y t o Me t h o d s o f C r i ti c a l P o i n t D e t e r m i n a t i o ne p r i n t e d w i t h P e r m i s s i o n f r o m 9 5 -a m b / y o u ; C o p y r i g h t9 5 A m e r i c a n C h e m i c a l S o c i e t y )

visua l-in glass tubevisua l-in cell with windowsn on vis ua l-pVT measurementoth e r n on v is u a l m e a s u r e m en tcritical pressure measurement combined with vapor

pressure measurement up t o the critical pointcritical pressure by extrapolation of vapor pressure curveor th ob a r ic d e n sity m e a s u r em e n tse qu a tion of s ta te , th e r m od yn a m ic s tu d ycalculation from another physical property

0. l it e r a t ur e s u r ve y

) w it h s t ir r in g) instrumenta l detection of critical point) s p ecia l fe a tu r e of a p p a r a tu s



10/12

But-1-yne. Unpubl ishe d me a sure me nt s on but -1-yneve been made by Steeles group [95-ste]. A 95%-puremp le was pu rchased from Scott Specialty Gases an d wasr ifi ed b y G L C t o 9 9.1 5%. T h e v a p or p r e ss u r e w a s

easur ed with a dead-weight gauge from 308 K t o 443 Ko de composit i on wa s observe d u nt i l 433 K), a nd t hetical t emperatu re wa s inferred t o be (440 ( 1) K by therne r i n t he c urve whe n pre ssure wa s pl ot t e d a ga i nst

mpe ra t ure . Be ca use t hi s i s a n i nsensi t ive me t hod, t hecertainty in Tc may be closer to 2 K. Correspondingly,

e uncertainty in the reported pc, 4.586 MPa, may be 0.2Pa. Plotting pressure against th e density, which was alsoeasured, led to the estimate Fc ) 0.257 gcm -3, wit h a ncertainty of 10%.

a l c u l a t i o n s w i t h t h e R a m s a y -S h i e l d s E q u a t i o n

In addition to the experimental measur ements on ethyned propyne, several reviews (e.g., ref 53-kob/lyn) reporttical t emperatu re values for C4 t o C5 a l kyne s t ha t ha veen determined with the Ramsay-Shields equation. Thisat best an approximation, because it is based on surface

nsion measurements and the relation between surfacension, , and critical temperature that was proposed by

msay and Shields [1893-ram /shi]:

e q 1, V is the molar liquid volume and k is a constantat is equa l to 2.12 for norm al subst an ces. As noted in

53-kob/lyn, k is not a t rue constan t an d eq 1 is of limitedcuracy.Morehouse and Maass [31-mor/maa, 34-mor/maa] mea-red the surface tension of propyne, but-1-yne, but-2-ynemethylacetylene), and pent-1-yne and converted them

nd th e sur face tension of ethyne) to critical temperat ur est h e q 1. We re ca l cul a t e d t he va l ue s a ft er not ing t h a tbe and Lynn [53-kob/lyn] had questioned the result for

opyne . Bot h se t s of c a lcul a t i ons, t he e xpe rime nt a llues, an d th e differences (from our calculat ions) ar e givenTable 4.The compa rison given in Table 4 clearly raises quest ionsout the results of Morehouse and Maass with eq 1. Thefference between calculated and experimental values

par ently increases with increasing carbon nu mber (theculated value for propyne agrees with the result givenre f 53-kob/l yn), a nd t he re fore t he unc ert a i nt y i n t he

lculat ed values for bu t-2-yne an d pen t-1-yne ma y exceedK. For this reason, we have not included any Tc values

lculated with eq 1 in Table 2.

v e r v ie w o f R e c o m m e n d a t i o n s ( Ta b l e 1 )

Table 1 summarizes the recommended critical valuesven in Table 2. It also includes, where appr opriate, the

tical volum e, Vc, and the critical compressibility factor,) pcVc/R Tc (R ) 8.314 51 J mol-1K-1). A superficial

mparison of the recommendations for linear alk-1-enes

with t hose for n ormal alka nes from r ef 95-amb/tso suggeststha t th e ratio of the Tcs r educes very close to u nity by C12,b u t t h e pc rat io does n ot decrease with increasing carbonnumbe r. At t he sa me c a rbon num be r, i t a ppea rs t ha t t he

pc of li ne a r a l k-1-e ne s i s 6% l a rge r t ha n t ha t of norma lalka nes. Steele and Ch irico [93-ste/chi], in th eir review ofthe properties of C5 + alkenes, have pointed out the similart re nds i n t he Fc of linear alk-1-enes and normal alkanes.

A c k n o w l e d g m e n t

This work is a product of the IUP AC Commission I.2 onThermodynam ics, Subcommitt ee on Th ermodynamic Data,

cri t ica l prope rt ie s group, unde r t he l ea de rship of C. L.Young (University of Melbourne, Melbourn e, Australia).The following members commented on t he preliminarydra ft of t he pa pe r: K. M. de Re uck (Impe ria l Coll ege,London, England), J. H. Dymond (University of Glasgow,Glasgow, Scotland), and C. L. Young. C.T. is grat eful t oExxon Research and Engineering Co. for permission topublish this paper.

R e g i s t r y N o . S u p p l i e d b y t h e A u t h o r : Et he ne , 74-85-1; propene, 115-07-1; but-1-ene, 106-98-9; pent-1-ene,109-67-1; hex-1-ene, 592-41-6; hep t-1-ene, 59 2-76-7; oct-1-ene, 111-66-0; non-1-ene, 124-11-8; dec-1-ene, 872-05-09;dodec-1-ene, 112-41-4; (Z)-but-2-ene, 590-18-1; (E)-but-2-ene, 624-64-6; 2-meth ylpropene, 115-11-7; (Z)-pent-2-ene,627-20-3; 3-methylbut-1-ene, 563-45-1; 2-methylbut-2-ene,

513-35-9; cyclopentene, 142-29-0; cyclohexene, 110-83-8;propadiene, 463-49-0; bu ta -1,3-diene, 106-99-0; h exa-1,5-diene, 592-42-7; (+)-(R)-p-mentha-1,8-diene [(+)-D-limonene],5989-27-5; (-)-(1S )-pin-2-ene, 7785-26-4; (+)-car-3-ene,13466-78-9; eth yne, 74-86-2; pr opyne, 74-99-7; but-1-yne,107-00-6.

Li te r atur e Ci te d

1879-a ns An sdell, G. Proc. R. Soc. London 1879, 29 , 209-214; Chem. News 1879, 40 , 136-138 (ethyne).

1 88 0-va n va n d er Wa a ls , J . D . Beibl. Ann. Phys. 1880, 4, 704(ethene).

1882-ca i Ca illet et , L. Comp t . Re n d . 1882, 94 , 1224-1226(ethene).

1882-n ad N adezh din , A. Zh. Russ. Fiz.-Khim. Obsh. 1882 , 14 ,

536 -541 (propene).1882-sa r Sarr au, E. Compt. Rend. 1882, 94, 845-851 (ethene).

1882-zhu Zh uk, K. Zh. R uss. Fiz.-Khim . Obsh. 1882, 14, 157-161 (2-meth ylbut-2-ene).

1883-n ad N ad ezh din , A. Zh. Russ. Fiz.-Khim. Obsh. 1883 , 15 ,25-29 (propene, 2-methylpropene, 2-methylbut-2-ene).

1 88 3-n a d -1 N a d ejd in e (s ic), A. Beibl. Ann . Phys. 1883, 7, 678 -681; summar y of 1882-nad, 1882-zhu, 1883-nad(propene, 2-methylpropene, 2-methylbut-2-ene).

1883-pa w P awlewsk i, B. Ber. Dtsch. Chem. Ges. 1883, 16,2633-2636 (pent-1-ene, oct-1-ene, hexa-1,5-diene).

1884-dew Dewa r, J . Philos. Mag. 1884 , 18 , 210-216 (ethene).

1886-cai /m at Cai ll et et , L.; Mat hi as, E. Compt. Rend. 1886, 102,1202-1207 (ethene).

1893-a lt Alt sch ul, M. Z . Ph y s . Ch e m. 1893, 11 , 577-597(pent-1-ene, hex-1-ene, oct-1-ene, dia mylene).

1893-r am / shi Ram say, W.; Shi el ds, J . Z . Ph y s. Ch e m. 1893, 12,433 -475.

1 89 5-ol s O ls ze ws k i, C h ar le s (s ic). Philos. Mag. 1895, 39,188 -212 (ethene).

1895-pic Pict et , R. Compt. Rend. 1895 , 120 , 43-45 (pent-1-ene).

1895-pi c/ alt Pi ct et , R.; Al t schul , M. Z . Ph y s . Ch e m. 1895, 16 ,26-28 (pent-1-ene).

1897-ku e Ku enen , J . P . Philos. Mag. 1897, 44 , 1 7 4-19 9(ethyne).

1897-vil Villa rd, P . An n . Ch i m. Ph y s . 1897, 10 , 387 -432(ethene).

b l e 4 . C r i t ic a l T e m p e r a t u r e o f Al k y n e sa

calcd tc /C expt l

3 4-m or /m a a t h i s w or k tc/C T/K

t h yn e 39.7 39.3 35.2 4.1r opyn e 121.6 141.6 129.2 12.4u t-1-yn e 190.5 189.1 167 22u t-2-yn e 215.5 215.5en t -1-yn e 220.3 220.0

a The value for ethyne was calculated with k ) 2.02, as given34-mor/maa; with the value k ) 2.09 given in 31-mor/maa, weculate 35.5 C, although even that reference gives 39.7 C.

V2/3 ) k(tc - t - 6) (1)



11/12

ves Vespign an i, G. B. Gazz. Chim. Ital. 1903, 33, 73-78 (pent-1-ene).

l es /ch a L es pi ea u , R .; C h av an n e, G . Compt. Rend. 1905 ,140, 1035-1036 (propadiene, propyne).

m ci McInt osh , D. J . Ph y s . Ch e m . 1907, 11 , 306-31 7(ethyne).

m a t Mat hias, E. Compt. Rend. 1909, 14 8, 1102-1105;J. Chem. S oc. 1909, 96, 552-553 (ethyne).

ca r /b a u C ar d os o, E .; B a um e, G . Compt. Rend. 1910, 151 ,141 -143 (ethyne).

ca r /a r n C ar d os o, E .; Ar n i, E . J. Chim. Phys. 1912, 10 , 504-508 (ethene).

ca r /b a u C ar d os o, E .; B a um e, G . J . Ch i m. Ph y s. 1912, 10,509 -513 (ethyne).

s ei /b ur S eib er t , F . M .; B u rr el l, G . A. J . A m . C h e m . S o c.1915 , 37, 2683-2691 (propene).

m a a /w r i M a a ss , O .; W r ig h t , C . H . J . Am. Ch e m. S o c. 1921,43 , 1098-1111 (ethene, propene, propyne).

lan/boe Landolt-Bor n s t ei n , Ph y s ik a l i s ch - Ch emi s c h e T a -bellen , 5th ed.; Springer -Verlag: Berlin, 1923; Vol.I, pp 253-266 (review).

cof/m a a C offi n , C . C .; M a a ss , O . Trans. R . S oc. Can. S ect. 31927, 21 (No. 3), 33-40 (2-meth ylpropene).

m at / cr o Mat hi as, E.; Cr om m eli n, C. A.; Wat t s , H. G. Com-mu n. Kam erlingh Onnes Lab., Univ. Leiden 1927,No. 189a (ethene).

cof/m a a C offi n , C . C .; M a a ss , O . J . A m . C h em . S o c. 1928,50 , 1427-1437 (butenes).

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m a t /cr o M a t h ia s , E . ; C r om m el in , C . A. ; W a tt s , H . G . An n .Phys. 1929, 11, 343 -353 (ethene).

m or /m a a M or e h ou s e F . R .; M a a ss , O . Ca n . J . Re s. 1931, 5,30 6-312.

win/ m aa Winkl er , C. A.; Maass, O. Can. J. Res. 1933, 9, 610 -612 (propene).

m or /m a a M or e h ou s e, F . R .; M a a ss , O . Can. J. R es. 1934, 11 ,63 7-643.

m a a /g ed M a as s , O .; G ed d es , A. L. Proc. R. Soc. London 1937 ,A236, 303 -332 (ethene).

g er /w il G er s h in ow it z , H . ; W il son , E . B ., J r . J. Chem. Phys.1938, 6, 247 -251.

m ci /m a a M cI n t os h , R . L .; M a a ss , O . Can. J. R es. B 1938, 16 ,

28 9-302 (ethene).dac/m ci Dacey, J . R.; McI nt osh, R. L.; Maass, O. Can. J. Res.

B 1939, 17, 206-213 (ethene).

m ci /dac McI nt osh, R. L.; Dacey, J . R.; Maass, O. Can. J. Res.B 1939, 17, 241-250 (ethene).

s ch /g il S ch e el in e , H . W .; G il li la n d , E . R . I n d . En g . Ch e m.1939, 31 , 1050-1057 (2-methylpropene).

g il /s ch G il li la n d , E . R .; S ch e el in e , H . W . Ind. Eng. Chem .1940, 32 , 48-54 (propene).

n a l /m a a N a ld r et t , S . N . ; M a a ss , O . Can. J. R es. B 1940, 18 ,11 8-121 (ethene).

s ou S ou d er s , M . P r iv at e com m u nica t ion t o Va u gh a nand Graves [40-vau/gra], 1940 (propene).

v au /gr a Va u gh a n , W. E .; G ra ve s, N . R . I n d . En g . Ch e m .1940, 32 , 1252-1256 (propene).

l u /n e w L u , H . ; N e wi t t, D . M .; R u h em a n n , M . Proc. R . S oc.London 1941, A178, 506-525 (propene).

bea/i ng Beat t ie, J . A.; I nger sol l, H. G.; St ockm ayer , W. H. J . Am. Ch e m. S o c. 1942, 64 , 546-548 (2-methyl-propene).

b en B en ed ict , M . P r iva t e com m u nica t ion t o B ea t t ie etal . [42-bea/ing] (2-methylpropene).

g a r /a d a G a r n er , J . B .; Ad a m s, L .; S t u ch e ll , R . M . Petrol.Refiner 1942, 21 , 321-332 (buta-1,3-diene).

cr a Cr agoe, C. S. Natl. Bur. Stand. LC-736 1943 (pro-pene, butenes, buta-1,3-diene).

dos Doss, M. P . Th e Physical Constants of the PrincipalHydrocarbons, 4th ed.; The Texas Co.: New York,1943.

4 5-s co/m e y S cot t , R. B. ; M ey er s , C . H . ; R a n ds , R . D ., J r .;Brickwedde, F. G.; Bekkedah l, N. J. R es. Natl. Bur.S t a n d . 1945, 35, 39-85 (buta-1,3-diene).

4 6-ol d/s a g O ld s , R . H . ; S a ge , B . H . ; L a ce y, W . N . I n d . En g .Chem . 1946, 38 , 301-303 (but-1-ene).

47-st u St ull, D. R. I n d . En g . Ch e m. 1947, 39 , 51 7-54 0(propadiene, propyne).

48-day/ni c Day, H. O.; Ni cholson, D. E.; Fel si ng, W. A. J . A m .Chem. Soc. 1948, 70 , 1784-1785 (pent-1-ene).

48-kay Ka y, W. B. Ind. Eng. Chem . 1948, 40 , 1459-1464(ethene).

4 8-m a s /m a a M a son , S . G .; M a a ss , O . Ca n . J . R e s. B 1948, 26 ,59 2-603 (ethene).

4 9-fa r /s a g F a r r in gt on , P . S .; S a ge , B . H . Ind. Eng. Chem. 1949,41 , 1734-1737 (propene).

4 9-m a r /p r e M a r ch m a n , H . ; P r e n gl e, H . W ., J r . ; M ot a r d , R . L .Ind. Eng. Chem . 1949, 41 , 2658-2660 (propene).

5 0-b ea /m a r B ea t t ie , J . A.; M ar p le , S ., J r . J . A m . C h e m . S o c.1950, 72 , 1449-1452 (but-1-ene).

51-ki y/i ke Kiyam a, R.; I kegam i, T.; I noue, K. Rev. Phys. Chem. J p n . 1951, 21 , 58 -62 (ethyne).

5 1-k iy /s u z K iy am a , R .; S u zu k i, K .; I k eg am i, T . Rev. Phys.Ch e m. J p n . 1951, 21 , 50-57 (2-meth ylbut-2-ene).

5 3-k ob /l yn K ob e, K . A. ; L yn n , R . E . , J r . Chem. Rev. 1953 , 52 ,11 7-236 (review).

53-whi /m as Whit eway, S. G.; Mason, S. G. Can. J. Ch em. 1953,31 , 569-584 (ethene).

55-kr e Kr eglewski, A. Rocz. Chem . 1955, 29 , 95-106(propene).

56-a m b Am br ose, D. Trans. Faraday Soc. 1956, 52 , 772-781 (ethyne).

5 7-a m b/gr a Am br os e, D .; G r an t , D . G . T r a n s . Fa r a d a y S o c.1957, 53 , 771-778 (cyclopentene).

5 8-r ow /s u t R ow li ns on , J . S. ; S u tt on , J . R .; We st on , J . F .Proceedings of the Joint Conference on Thermody-nam ic and Transport Properties of Fluids, 1957;Institu tion of Mechanical Engineers: London, 1958(ethene).

6 0-a m b /cox Am b r os e, D. ; C ox , J . D .; T ow n se n d, R. Trans.Faraday Soc. 1960, 56, 1452-1459 (pent-1-ene, hex-1-ene, h ept-1-ene, oct-1-ene, but-2-enes, cyclohex-ene).

62-che/m cc Cheng, D. C.-H.; McCoubr ey, J . C.; Phi ll ips, D. G.Trans. Faraday Soc. 1962, 58 , 224-229 (cyclohex-ene).

62-voh/ kan Vohr a, S. P.; Kang, T. L.; Kobe, K. A.; McKet t a, J .J . J. Chem. En g. Data 1962, 7, 150-155 (propyne).

6 4-a m b /t ow Am b r os e , D .; T ow n s en d , R . T r a n s . Fa r a d a y S o c.1964, 60 , 1025-1029 (ethyne).

6 4-s h i/k oh S h im , J . ; K oh n , J . P . J . Ch em. En g . Da t a 1964, 9,1-2 (ethene).

66-kho Kh odeeva, S. M. Ru s s . J . Ph y s . Ch e m. 1966, 40 ,1061-1063 (ethyne).

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7 1-l en /r e b L en oi r , J . M .; R eb er t , C . J . ; H i pk in , H . G . J . Ch e m.Eng. Data 1971, 16, 401-404 ((Z)-pent-2-ene).

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Received for r eview August 8, 1995. Accepted May 1, 1996.

JE9501999

X Abstract published in Advance ACS Abstracts, June 15, 1996.


VL Critical Prop Elements Compounds Unsat Aliphatic HCs

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