March 1947
INDUSTRIAL AND ENGINEERING CHEMISTRY LITERATURE CITED
COSCLUSIONS
All present indications point to the conclusion that fluorine chemistry is destined to become a large and important division of the science, both from its theoretical importance and its commercial application. It is just beginning t’o broaden out to show its individual significance, its bearing on the rest of science, and its industrial applications. It has been slow in starting, because its techniques are different and difficult, but chiefly because its foundation depended primarily upon basic academic research which has been carried out by only a fen- investigators due to technical difficulties. Fluorine and its compounds have unique properties, due t,o the fact that fluorine not only occupies the extreme upper right-hand corner of the Periodic Table but that it, is much more electronegative than its nearest neighbors. Having extreme properties, these compounds not only test and extend our theories of chemical combination, struct,ure, and reaction, but provide large numbers of nerv substances of unique and extreme properties for many important utilitarian purposes. Luckily fluorine is not a rare element. Much more fundamental academic research is required and an increasing amount of development to exploit this field. Our theories will need to be tested and renovated, and new ones formulated. New methods of synthesis will have to tie discovered, old ones modified, and new catalysts found. Fluorine compounds are of chief interest in the estrenies of properties of chemical substance.. On the one side there re compounds of great. inertness and stability, on t’he ot,her, compounds of great reactivity. Certain compounds of fluorine are among the most nontoxic of substances, others are among the most poisonous substances known. Both inorganic and organic compounds in enormous numbers will be prepared with all conceivable gradation of properties. Many fluorine compounds are and will be utilized as end products, others are finding use in small quantities in mixtures. Some are useful as powerful catalysts and others serve or will serve as intermediates. Fluorine compounds are certain to find application or eventual use in all ramifications of chemical production, theory, and utilization.
241
In all references only the beginning papers on the phaae of the subject are given. Bauer, S.H., Beach, J. I-., and Simons, J. H., J . Am. Chem. Soc., 61,19 (1939). Bigelow and Calfee, Ibid., 59, 2073 (1937). Booth, H. S.,Mong, IT. L., and Burchfield. P. E . , ISD. ENG. C H E U . . 24. ,~328. 637 (1932). Brice, T: J., Pearlson, IT, H., and Simons, J . H., J . Am. Chem. Soc., 68, 968 (1946). Brockway, L. O., J . Phys. Chem., 41,185, 746 (1937). Brockway, L. 0.. Secrist, J. H., and Lucht. C. 11..Div. of Phys. Br Inorg. Chem., .1.C.S, Buffalo, 1942. Cady, G. H., J . ilm. Chem. Soc., 56, 1431 (1934). Fredenliagen and Cadenhach. Ber., 67B,928 (19341. Geunther, P., Holm, I analogous to the hydrocarbon system poses a problem of nomenclature that has been a source of much inconvenience in the field. The present Chemical Abstracts system of nomenclature is completely adequate in that it is an explicit description which follon-s established internat’ional rules \vorlted out to fit into the whole picture of chemical nomenclature. However, some of the rcsulting names are so lengthy and involved that there has been a strong and understandable desire to develop a simpler terminology, at least for everyday use. Twice while the articles in this issue were under review, concert,ed efforts lvere made t,o effect such a simplification. The first was made by t,he panel reviewing the submitted manuscripts, which contained several proposals for simplified terminology. After discussing the various proposals, the members of the panc.1 who were present made the recommendation that the prefix “perfluoro” be used to denote complete substitution by fluorine of all positions attached to the carbon skeleton. Correspoiiclencc with the editor of Chemical Abstracts, viho is also the chairman of the official A.C.S. committee on nomenclature, and with the chairman of the nomenclature committee of the A.C.S. Division of Organic Chemistry indicated their general agreement: this recommendation was transmitted to all authors a t the time the papers were returned with review comments. h s a result, most of the authors adopted the “per” nomenclature in Tvhole or in part. Bcceptance of this usage was not’ universal, however, and some of the objections raised appeared to just,ify additional consideration of the problem. At a very late &age a second meeting was held in the offices of Chemical Abstracts. Present at, this meet.ing were persons representing t,he various viewpoints concerning the
fluorine nomenclature. .Also present were the editor of Chemical Abstracfs, the chairman of the Organic Chemistry Division’s committee on nomenclature, a representative of INDUSTRIAL AND ENGISEERING CHEMISTRY,and several nomenclature experts from the Chemical Abstracts staff. Extended discussion failed to produce the hoped-for general agreement’. The point was developed, however, that the “per” usage proposed n-as recognized by Chemical -4bstracts as permissible, although it had not been adopted for use in the indexes as outlined in the ext>cnsiveintroduction on nomenclature to the 1946 subject indrls for that journal. Because of the lack of general agreement (luring the time available for discussion, it n’as the sentiment of the group that thv to in publication existing Chemical Abstracis usage be adhi~rt~tl until Iatrr discussions shed furt,her ligh: on the subject. Plans are now lieing developed for such R meetin:., open to all interested persons, to be held at the .ipril 1947 Atlantic C’itj- A.C.3. meeting under Chemical Abstracts sponsorship. .I h.;t CJf typical compounds, giving formula and Chernical A bsiracts name. t h e Internat,ional Union of Chemistry usage, and thtx “per” terminology. is presented on page 212 for tht, informztion of tho.;e interested. The nomenclature usage in this issue largely follo~~vs the preference of the individual authors after they had received the original recommendation by t,he review panel for the “per” usage. Time did not permit rephrasing of the text to a desirable uniformity in terminology after t,he last meeting. However, pains have been taken t,o ensure that no ambiguity remains regarding t,he actual compounds described. Perhaps those variations that exist will even serve some useful purpose in stimulating further thought and an early solution to the prohlem.
INDUSTRIAL AND ENGINEERING CHEMISTRY
242
Vol. 39, No. 3
Nomenclature of Fluorine-Containing Compounds C.A.
Compounds
Hexadecafiuoroheptane
C7F16
F FzC/
I .u.c
.
Hesadecafluoroheptane
“Per” System Perfluoroheptane
CFS
Y‘CFZ I
I
FzC\
Decafluoro-l,3-bis(trifluoromethyl)- 1,3-Bis(trifluoromethyl)decafluoro-
/CF-CF,
cyclohexane
cyclohexane
Perfluoro(-1,3-dimethylcyclohexanej
C F2
Chloropentadecafluoroheptane
Chloropentadecafluoroheptane
............
Pentadecafluoroheptane
Pentadecafluoroheptane
............
Octafluoronaphthalene
Octafluoronaphthalene
Perfluoronaphthalene
J FJ JF F
Octadecafluorodecahydronaphthalene Octadecafluorodecahydronaphthalene Perfluoronaphthalane
F2
Fz
CF~-CFz-COzH
I
CFz-CFz-C0zH CFsCOzH CFz-CFz-COXH2
Octafluoroadipic acid
Octafluorohesanedioic acid
Perfluoroadipic acid
Trifluoroacetic acid
Trifluoroethanoic acid
Perfluoroacetic acid
a,a,P,P,r,r,6,s-OctaAuoroadipamide Octafluorohexanediamide
.............
a,a,P,P,y,r,G,s-Octafluorovaleric acid 2,2 3 3 4 4 5 5-Octafluoropentanoic &jd’ ’ ’ ’
............. Perfluoroadiponitrile
Octafluoroadiponitrile
Octafluorohexanedinitrile
Dodecafluoroheptene
Dodecafluoroheptene
Hexafluorobenzene
Hexafluorobenzene
Octafluorotoluene
(Trifluoromethy1)pentafluorobenzene Perfluorotoluene
Chloropentafluoroethane Chlorotrifluoroethylene
1-Chloro-1,1,2,2,2-pentafluoroe thane l-Chloro-l,2,2-trifluoroethene Hexafluoro-1,3-butadiene
. . . . . . . . . . .. . Perfluorobenzene
I
F’vF F
CFaCFzC1 CFz=CClF CFz=CF-CF=CFZ
Hexafluoro-l,3-butadiene CL,CL,CL,
a’,a’, a’-Hexafluoro-m-xylene
0
/
;HFCF&F*CCIR F2CFzCFa CFzCFzCClFz
.............
Perfluoro-1,3-butadiene
.............
Bis(heptafluoropropy1)ether
1-Heptafluoroproposy-1’-heptafluoropropane
Perfluoro-n-propyl ether
2,3-Dichlorohesafluoro-2-butene 1,2,2,3,3,4-Hexachloro-l, 1,4,4-tetra-
2,3-Dichlorohexafluoro-2-butene 1,2,2,3,3,4-Hexachloro-l, 1,4,4-tetrafluorobutane
............. .............
fluorobutane CFSC-CF, CFaCHFCF2CFs CzFsCOOCzFr
1,3-Bis(trifluoromethyl)benzene
.............
Hexafluoropropanone
Hesafluoropropanone
1,1,1,2,3,3,4,4,4-Nonafluorobutane
1,1,1,2,3,3,4,4,4-Nonafluorobutane
Pentafluoroethyl pentafluoropropionate
Pentafluoroethyl pentafluoropropanoate
Perfluoroacetone
............. Perfluoroethyl perfluoropropionate
l-Chloro-l,1,2,2,3,3,4,5,~,6,6,7,7,7- , . . . . . . . . . . . . l-Chloro-1,1,2,2,3,3,4,5,5,6,6,7,7,7tetradecafluoroheptane
1-Chlorotridecafluorohexane
tetradecafluoroheptane
l-Chloro-l,1,2,2,3,3,4,4,5,5,6,6,64ri- , . . . . . . . . . . . . decafluorohesane
