Literature Resources for Petroleum Chemicals - ACS Publications

34 Literature Resources for Petroleum

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Chemicals MORRIS D. SCHOENGOLD Esso Research and Engineering Co, P. O. Box 51, Linden, N. J. 07036

The field of petrochemicals has grown over the past 10 years to the extent that at present petroleum has essentially replaced coal as the primary raw material for preparing organic chemicals. In some cases, it has begun to penetrate the field of inorganic chemicals. In accordance with this growth, the literature of the subject has also grown tremendously. This article is a general guide to the sources of information in this area. It covers the general sources first and then particular processes, such as oxidation, hydrogenation, halogenation, and nitration. Representative books and articles are listed in the bibliography. Some general guides to the patent literature are also included.

T

he r a w materials for the petrochemical industry are obtained from crude petroleum either by being present as such i n the crude or b y the chemical operations during refining to prepare the primary products such as gasoline, lubricating oils, heating oils, and asphalts. T h e products thus obtained include chemicals such as ethylene, propylene, butadiene, benzene, toluene, a n d the xylenes. These may be considered the primary petrochemicals. M a n y secondary derivatives are obtainable from these, including polyethylene, polypropylene, polystyrene, polyesters, polyurethanes, phenolic resins, various types of synthetic rubbers, ethylene chloride, trichloroethylene, ethyl chloride, ethanol, acetaldehyde, styrene, ethylene oxide, ethylene glycol, v i n y l acetate, ethylene dibromide, acrylonitrile, a n d others. The growth rate of petrochemicals continues to increase, and petroleum has essentially replaced coal as the primary organic raw material. According to the 1965 Petrochemical Handbook issue of Hydrocarbon Processing, o i l and natural gas account for more than 9 3 % of a l l basic organics. Petrochemical feedstocks account for almost 4% of U . S . crude petroleum production and imports. D e m a n d for petrochemical feedstocks is growing about 1 1 % per year. B y 1970 it is estimated that petrochemicals should account for 7 0 % of total value and 4 2 % of total chemicals produced. 550 In Literature of Chemical Technology; Smith, J.; Advances in Chemistry; American Chemical Society: Washington, DC, 1968.


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Thus, the importance of the industry and the need for knowing the sources of information is apparent. There are several ways i n w h i c h these sources can be discussed—i.e., by the individual chemicals and the products obtainable from them, chemical by chemical or type by type, or by the products obtained. Thus, we could have sections devoted to the preparation of paraffins, olefins, aromatics, etc., or we could have sections devoted to materials such as plastics, rubbers, textile chemicals, solvents, etc. However, since the limitations of the paper restrict, I discuss the subject on the basis of processing, such as oxidation, halogenation, nitration, etc. In this way the paper w i l l be kept within bounds, and the subject w i l l be adequately covered. I do not propose to be a l l inclusive. M y object is to present general guidelines to sources of information on the various processing of petrochemical feedstocks. I list both special and usual sources and discuss their usefulness from the special aspect of petrochemistry. General

Sources

The literature serves a dual purpose. First, it keeps the worker aware of current research and who is currently active i n a particular field of endeavor. Second, it informs the worker of what has been previously done. This prevents duplication and serves to orient new workers i n the field. Obviously, the type of material used i n each of these functions differs. In the first a r e a — current awareness—it is necessary that the worker be aware of a l l the primary journals w h i c h publish the results of new research. H e must keep himself informed by reading them as they appear. It is also necessary that one be familiar w i t h the patents issued each week since many technological advances are first announced i n the patent literature. Thus, one must be aware of the sources of information for patents. T h e second type of use made of the technical information is served by a different type of publication. These may be trade publications, review journals or abstracts journals. M a n y of the abstracts journals are subject oriented and serve a specific industry or, like Chemical Abstracts, the entire field of chemistry. E a c h of these sources has its purpose and function. Little has been published w h i c h is devoted solely to petrochemistry. Several books, a few magazines, some symposia, and an abstract bulletin are the sole fruits of this endeavor. Petrochemistry is covered broadly by the books published since 1955, which are listed alphabetically by author i n the bibliography. However, mention should be made of one standard reference work w h i c h was published in 1934 but w h i c h is still the best guide to the literature up to that date. It is E l l i s ' "Chemistry of Petroleum Derivatives," published i n two volumes by the Chemical Catalog C o . Although out of print and rather old, it is still the basic book reviewing the literature up to the publication date. It contains many references to the early patents and literature and is essential i n making searches. Another useful book is " T h e Chemistry of Petroleum Hydrocarbons," by Brooks i n three volumes. Volume 1 contains 21 separately authored chapters

In Literature of Chemical Technology; Smith, J.; Advances in Chemistry; American Chemical Society: Washington, DC, 1968.


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covering subjects such as hydrocarbons i n natural gas, gasolines, kerosenes, gas oils, and lubricating oils; separation of aromatics by selective adsorption; preparation of pure paraffins and olefins; synthesis of low and high molecular weight hydrocarbons; and the Fischer-Tropsch process. Volume 2 contains 16 chapters covering acetylene by the pyrolysis of light hydrocarbons; pyrolytic reactions of aromatic hydrocarbons; hydrocarbon oxidation; synthesis of gas from methane, oxygen, and steam; partial oxidation of simple paraffinic hydrocarbons; and special oxidation reactions of unsaturated hydrocarbons. Volume 3 contains 22 chapters covering oxidation of o-xylene to phthalic anhydride; isomerization of olefins and saturated hydrocarbons; chlorination, fluorination and nitration of paraffins and cycloparaffins; Diels-Alder reactions; the Oxo reaction; alkylation; aromatic substitution; and sulfonation and nitration of aromatic hydrocarbons. The volume by Brooks and Dunstan contains chapters covering chemicals for synthetic rubber, organic chemicals from hydrocarbons of petroleum, nitroalkanes, carbon black, and surface-active agents. Goldstein's book covers major products from a commercial and manufacturing point of view and contains m u c h economic data. Groggins' volume covers unit operations such as alkylation, halogenation, and nitration. "Advances i n Petroleum Chemistry and Refining," by Kobe and M c K e t t a is an annual publication w h i c h presents current developments i n the petroleum and petrochemical industries. The chapters are individually authored and cover subjects such as the manufacture of petrochemical acetylene; nitriles and amines; synthetic ammonia; aromatics from petroleum; manufacture of mono- and diolefins from paraffins by catalytic dehydrogenation; synthetic detergents from petroleum; nitrogen fertilizers; Oxo process; pesticides from petroleum; various aspects of the petrochemical industry; and similar subjects. There is a cumulative index i n Volume 10. Also of interest because they relate specifically to petrochemicals are the various symposia w h i c h have been held by the American C h e m i c a l Society at its semiannual meetings. These have generally been sponsored by the Division of Petroleum Chemistry. The American Institute of C h e m i c a l Engineers held a symposium on petrochemicals and petroleum refining w h i c h was reprinted i n Chemical Engineering Progress Symposium Series. Several books have been published w h i c h cover the physical properties of hydrocarbons and petrochemicals. These are other than the standard handbooks w h i c h are generally familiar and are listed w i t h the general books i n the bibliography. There are many books w h i c h are of interest to the petroleum chemist but w h i c h are also of general interest to the chemist. These include the books on organic chemistry, inorganic chemistry, physical, analytical, and the other branches of the subject. These w i l l not be discussed here. However, of p r i mary interest are the following three compendia w h i c h cover both chemical technology and organic chemistry. Kirk-Othmer's "Encyclopedia of Chemical Technology" is an excellent source of information for all petrochemicals. "Ullmann's Enzyklopedia der Technischen C h e m i e " is i n the same category as Kirk-Othmer except that it is i n German. M a n y of the articles contain


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references to the original literature. Both of these are currently being revised. Houben-Weyl's "Methoden der Organischen C h e m i e " is an excellent source of information on organic chemicals, from the chemist's point of view. It contains volumes devoted to the chemistry and preparation of organophosphorus, nitrogen, sulfur, oxygen, and halogen compounds. A l l of the articles are individually authored and contain many references to the original literature.


Also of interest i n this regard are the various publications w h i c h have appeared as a result of the American Petroleum Institute's research projects. Periodicals, Abstracts, and Information Services. Several periodicals are of interest to the field of petrochemicals because of the annual special reports they issue. Examples of these are the annual petrochemical reports of the Oil and Gas Journal. The latest lists U . S . petrochemical construction projeets i n elastomers, aromatics, ammonia, ethylene, and sulfur. It also contains the Journal's annual petrochemical survey w h i c h lists all U . S . and foreign plants and their products. The Petrochemical Handbook issue of Hydrocarbon Processing is another important source of information. This special annual issue gives flow diagrams for the industrial production of the important petrochemicals. T h e 1965 issue contains 131 flow diagrams. T h e information for each process includes raw materials, products obtained, a general description of the process, yields, commercial installations, and where to obtain additional information. B o t h these journals also publish articles of current interest, describing new processes or reviewing older processes. A n example of these is the series on making ethylene and butadiene w h i c h the Oil and Gas Journal reprinted i n 1957. T h e annual review issue of Industrial and Engineering Chemistry, w h i c h ceased publication i n 1963, contained review articles covering recent advances i n the field of alkylation, halogenation, oxidation processes, hydrogénation and dehydrogenation processing, and sulfonation and sulfation processes. In some of the issues polymerization was also covered. These reviews are now published w i t h each issue and serve as good sources for reviewing the annual progress i n these fields. Economic information concerning petrochemicals is available from the usual sources of such information. Thus, the U . S . Tariff Commission issues its Synthetic Organic Chemicals, U.S. Production and Sales report annually. As the title indicates, the information is concerned w i t h the production and sales of a l l organic chemicals during the period covered. Stanford Research Institute issues its " C h e m i c a l Economics Handbook" i n loose-leaf form. This contains information on the basic economic data significant to the chemical industry. It covers economic data on individual chemicals and raw materials, on the principal chemical-consuming industries and on financial aspects of the chemical industry. The publication Search published by Compendium International Publishing Corp. regularly gives information on prices, sources of chemicals, production, exports and imports, new plants, etc. Predicasts abstracts information on forecasts and market data by product from articles appearing i n over 250 trade journals. Chemical Market Abstracts, published monthly by Foster D . Snell, Inc. claims to be a comprehensive guide to the world's chemical markets. It also contains information on chemical production, prices, and markets. Although not primarily concerned w i t h petrochemicals, mention should never-



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theless be made of the American Petroleum Institute's publication "Petroleum Facts and Figures." The latest edition (1965) is designed to bring together within a single volume the most complete and comprehensive record available of the petroleum industry's operations. T h e refining section contains tables on crude runs, refineries, stocks, production of petrochemical feedstocks, and finished products. M u c h statistical and economic information is contained i n the various publications by the Noyes Development C o r p . of Park Ridge, N e w Jersey. These publications generally give detailed accounts of the technical information available on the subject matter of the report along w i t h some economic information. Some of the reports cover such topics as acetylene, acrylic acids and esters, acrylonitrile, ammonia and synthesis gas, aromatics, caprolactam, chemicals from ethylene, chemicals from propylene, etc. Finally, the U . S . Bureau of Mines has issued several bibliographies of investment and operating costs for chemical and petroleum plants covering the period 1930-1958. Specific

Sources According

to

Process

Oxidation. M a n y chemicals are produced by oxidizing petrochemical feedstocks. A number of articles have been written on this subject and have been included i n some of the aforementioned books, such as the one by Brooks et al. on the chemistry of petroleum hydrocarbons and i n Kobe and McKetta's "Advances i n Petroleum Chemistry and Refining." Both of these should be consulted for review articles on oxidation. In addition to these, several books have also been published w h i c h cover the subject i n greater detail. Examples of these are given i n the bibliography. Shtern's book reviews research on the oxidation of paraffins, olefins, naphthenes, and aromatics. It covers the Russian work fully and contains extensive bibliographies to both Russian and nonRussian work. Articles w i t h particular emphasis on petrochemical oxidation are also included i n the bibliography. Alleviation. Another important petrochemical reaction is alkylation, and m u c h work has been done i n this field. Booth and Martin's book includes a discussion of the use of boron trifluoride as an alkylation catalyst. T h e book by Egloff and H u l l a is a compilation of patents on the alkylation of alkanes, classified according to process. The volume by Topchiev et al. is translated from the Russian and contains sections on the use of boron trifluoride i n alkylation reactions. W i l l i a m s ' work discusses homolytic aromatic substitution, w h i c h includes alkylation reactions. Too many articles have been written on alkylation reactions to list them all. However, those w h i c h review the subject w e l l are listed i n the bibliography. I should also like to mention the annual reviews of the literature w h i c h have been published i n Industrial and Engineering Chemistry. Isomerization. Isomerization is a reaction frequently used i n the petrochemical industry but not to the same extent as alkylation or oxidation. H o w ever, it is a useful reaction and much work has been done w i t h it. M o y discusses developments during the period 1952-1962 i n catalytic isomerization, along w i t h other processes. T h e work by Topchiev et al. previously mentioned


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contains â section on the use of boron trifluoride i n isomerization reactions. A symposium on isomerization and related processes was held at the A p r i l 1959 meeting of the American Chemical Society, Division of Petroleum Chemistry.


Hydrogénation. Sources of information w h i c h cover hydrogénation and dehydrogenation are listed i n the bibliography. Halogenation. Halogenation has been extensively investigated, and many books and articles have been published. Representative ones are given i n the bibliography. Here again the annual reviews i n Industrial and Engineenng Chemistry should always be consulted. Nitration. Although not as important from a petrochemical point of view as any of the other reactions, some work has been carried out i n this area, and the sources should be listed. O f interest is the symposium w h i c h was held at the 132nd American C h e m i c a l Society, Division of Petroleum Chemistry Meeting i n N e w York i n September 1957. T h e topic was nitrogen compounds i n petroleum, and 10 papers were presented. Nitration is also covered by the Industrial and Engineering Chemistry annual unit processes review. Also worthy of mention is A P I Project 52 on the nitrogen constituents i n petroleum. Sulfonation. Here also the annual review of Industrial and Engineering Chemistry must be mentioned. A P I ' s Project 48, w h i c h has been i n process for many years, is concerned w i t h the synthesis, properties, and identification of sulfur compounds i n petroleum. Other articles and books of interest are given i n the bibliography. Polymerization. O f all the areas of petrochemistry none has received more attention than polymerization, especially since the advent of the Ziegler catalyst. The subject has been discussed i n great detail, and no attempt w i l l be made to cover the sources here. However, some attempt w i l l be made to indicate the magnitude of the material that has been published and to point out some of the books and articles w h i c h w i l l serve as a start i n becoming familiar w i t h the field. I shall limit myself to the polymerization of olefins and diolefins i n order to keep this section within bounds. Interscience started issuing the digest service Resins, Rubbers, Pfostics i n 1947. This publication, later issued by Information for Industry, contains an annual index to the material digested, and the digests themselves are long and frequently contain data taken from the articles. This service was discontinued i n 1965. There are also many periodicals devoted exclusively to polymers and polymerization. Examples are European Polymer Journal, Fortschntte der Hochpolymeren Forschung, Journal of Applied Polymer Science, Journal of Polymer Science, Die Makromolekulare Chemie, Polymer, Polymer Previews, and Polymer Report. In addition to the journals many books have been written covering various aspects of the subject. One of the earlier publications and still excellent for the old material is E l l i s ' "Chemistry of Synthetic Resins." Published i n two volumes i n 1935, it covers most of the old literature and should always be consulted for information w h i c h may have been published prior to the p u b l i cation date of the set.


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I have tried to give an overall view of some of the sources of information i n the field of petrochemistry. Naturally, it has been impossible to cover the entire field a n d still keep this paper within bounds. However, I believe that the contents a n d leads given here w i l l serve as a start to anyone wishing some basic information.

BIBLIOGRAPHY General Texts and Handbooks Asinger, F., "Einfuhrung in diePetrolchemie,"Akademie-Verlag, Berlin, 1959. Asinger, F., "Chemie und Technologie der Monoolefine," Akademie-Verlag, Berlin, 1957. Asinger, F., "Chemie und Technologie der Paraffin-Kohlenstoffe," Akademie-Verlag, Berlin, 1956 (translated into English). Astle, M. J., "The Chemistry of Petrochemicals," Reinhold Publishing Corp., New York, 1959. Brooks, Β. T., "The Chemistry of Petroleum Hydrocarbons," Reinhold Publishing Corp., New York, 1954-55, 3 vols. Brooks, B. T., Dunstan, A. E., "The Science of Petroleum," Vol. 5, Part II, "Syn thetic Products of Petroleum," Oxford University Press, New York, 1953, 329 pp. "Chemical Economics Handbook," Stanford Research Institute, Menlo Park, Calif. Dreisbach, R. R., "Physical Properties of Chemical Compounds," 3 vols. ADVANCES IN CHEMISTRY SERIES 19 (1955), 22 (1959), 29 (1961), American Chemical Society, Washington, D. C. Egloff, G., "Physical Constants of Hydrocarbons," Reinhold PublishingCorp.,1939-53, 5 vols. Ellis, Carleton, "Chemistry of Petroleum Derivatives," Chemical Catalog Co., New York, 1943, 2 vols. Faith, W. L., "Industrial Chemicals," 3rd ed., John Wiley & Sons, New York, 1965. Ferris, S. W., "Handbook of Hydrocarbons," Academic Press, New York, 1955. Goldstein, R. F., A. L. Waddams, "The Petroleum Chemicals Industry," 3rd ed., E. & F. N. Spon, Ltd, London, 1967. Groggins, P. H., "Unit Processes in Organic Syntheses," 5th ed., McGraw-Hill Book Co., New York, 1958. Hatch, L. F., "The Chemistry of Petrochemical Reactions," Gulf Publishing Co., Houston, 1955. Hatt, H. H. et al., "Anti-Composition Tables for Organic Compounds," Cambridge University Press, Cambridge, England, 1955. Houben-Weyl, "Methoden der Organischen Chemie," G. Thieme Verlag, Stuttgart. Kirk, R. E., Othmer, D. F., "Encyclopedia of Chemical Technology," Interscience Publishers, New York. Kobe, K. A., McKetta, J. J., "Advances in Petroleum Chemistry and Refining," Interscience Publishers, New York, 1958-1965, 10 vols. Kobe, K. A. etal.,"Thermochemistry of Petrochemicals," University of Texas, Austin, 1958. "Petroleum Facts and Figures," American Petroleum Institute, New York, 1965. Steiner, H. M., "Introduction to Petroleum Chemicals," Pergamon Press, New York, 1961. Topchiev, Α. V. et al., "Synthetic Materials from Petroleum," Pergamon Press, New York, 1962. "Ullmann's Encyklopädie der Technischen Chemie," Urban & Schwarzenberg, Munich, 1958. Waddams, A. L., "Chemicals from Petroleum—An Introductory Survey," London, 1962.


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Symposia American Chemical Society, 1155 Sixteenth St., N . W., Washington, D. C. 20036: Aromatic Hydrocarbons (Atlantic City, 1962) Mechanism of Homogeneous and Heterogeneous Hydrocarbon Reactions ( Kansas City, 1954) Monomers and Polymers from Petroleum ( St. Louis, 1961 ) Oxidation to Produce Petrochemicals ( Cleveland, 1960 ) Production and Use of Alpha Olefins ( Los Angeles, 1963 ) Recent Developments in Chemicals from Petroleum ( San Francisco, 1958 ) Recent Advances in Hydrocarbon Catalysis (Chicago, 1961 ) American Institute of Chemical Engineers, 345 East 47th St., New York, Ν. Y. 10017: "Symposium on Petrochemicals and Petroleum Refining," Chem. Eng. Progr. Symp. Ser. No. 57 (1961). A P I Research

Projects

American Petroleum Institute, 1271 Avenue of the Americas, New York, Ν. Y. 10020: No. 6—Hydrocarbons in Petroleum No. 37—The Fundamentals of Hydrocarbon Behavior No. 42—Synthesis and Properties of High Molecular Weight Hydrocarbons No. 44—Data on Hydrocarbons and Related Compounds No. 47—Solid-Fluid Interactions as Related to Petroleum Production No. 48—Synthesis, Properties and Identification of Sulfur Compounds in Petroleum No. 52—Nitrogen Constituents in Petroleum No. 56—Isolation, Identification and Characterization of Metal-Bearing Organic Compounds Contained in Petroleum and Natural Asphalts No. 58—Synthesis and Purification of Hydrocarbon Standard Samples Periodicals, Abstracts, and Information Services* Abstracts of Papers, American Chemical Society, 1155 Sixteenth St., N . W., Wash ington, D. C. 20036, 2 times a year. Agricultural Chemicals, Industry Publications, Inc., Box 31, Caldwell, N . J . , 1946, monthly. Agricultural News Letter, Ε. I. du Pont de Nemours & Co., Public Relations Depart ment, Wilmington, Del. 19898, 1932, quarterly. AIChE Journal, American Institute of Chemical Engineers, 345 East 47th St., New York, Ν. Y. 10017, 1955, bimonthly. AIChE Program Abstracts, American Institute of Chemical Engineers, irregular. American Petroleum Institute, Abstracts of Refining Literature (formerly API Tech nical Abstracts), American Petroleum Institute, 1271 Avenue of the Americas, New York, Ν. Y. 10020, weekly. Angewandte Chemie, International Edition in English, Verlag Chemie G m b H , Pappelallee 3, Weinheim/Bergstr., Germany and Academic Press, Inc., I l l Fifth Ave., New York, Ν. Y. 10003, 1962, monthly. Applied Science and Technology Index, H . W . Wilson Co., 950 University Ave., New York, Ν. Y. 10452, 1913, monthly. Auszuege Aus Den Patentanmeldungen, Wila Verlag fur Wirtschaftswerbung W i l helm Lampl, Landsberger Strasse 191 a, Munich 12, Germany, 1955, weekly. Biological and Agricultural Index (formerly Agricultural Index), H . W. Wilson Co., 1916, monthly. British Chemical Engineering, (incorporating the Industrial Chemist), Heywood & Co., Ltd., Drury House, Russell St., London W C 2 , England, 1956, monthly. British Phstics, Iliffe Industrial Publications, Ltd., Dorset House, Stamford St., London SE1, England, 1929, monthly. British Technology Index, Library Association, Chaucer House, Malet Place, London W C 1 , England, 1962, 11 times a year. * List compiled by Charlotte Schaler, P. O. Box 366, Tarrytown, Ν. Y.



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Bulletin of the Japanese Petroleum Institute, Japan Petroleum Institute, To-nen B l d g , 1, Tori 3-chome, Nihon bashi, Chuo-ku, Tokyo, Japan, annual. Bulletin de la Société Chimique de France, Masson et C i e , 120 Boulevard SaintGermani, Paris 6, France, monthly. Bulletin de ία Société Chimique Belges, Masson et Cie, monthly. Canadian Chemical Processing, Southam Business Publications, L t d . , 1450 Don Mills R d , Don Mills, Ontario, Canada, 1917, monthly. Canadian Journal of Chemical Engineering, Chemical Institute of Canada, 48 Rideau St., Ottawa 2, Ontario, Canada, 1929, bimonthly. Canadian Journal of Chemistry, National Research Council, Ottawa 2, Ontario, Canada, 1929, monthly. Chemical Abstracts, American Chemical Society, 1907, weekly: Year Section 1912 22. Petroleum, Asphalt, Coal Tar and Wood Products 1961 22. Petroleum, Lubricants, and Asphalt 1962 52. Petroleum and Petroleum Derivatives 1963-66 27. Petroleum, Petroleum Derivatives, and Related Products 1967 51. Petroleum, Petroleum Derivatives and Related Products Chemical Engineering, McGraw-Hill Book C o , 330 West 42nd S t , New York, Ν. Y. 10036, 1902, semimonthly. Chemical Engineering Progress, American Institute of Chemical Engineers, 1947, monthly. Chemical and Engineering News, American Chemical Society, 1923, weekly. Chemical Engineering Science, Journal International de Genie Chimique, Pergamon Press, 122 East 55th St., New York, Ν. Y. 10022, 1951, monthly. Chemical Market Abstracts, Foster D. Snell, Inc., 29 West 15th St., New York, Ν. Y. 10011, 1950, monthly. Chemical and Process Engineering, The Tower, Shepherds Bush R d , London W6, England, 1950, monthly. Chemical Titles, American Chemical Society, 1961, semimonthly. Chemical Reviews, American Chemical Society, 1924, bimonthly. Chemical Week, McGraw-Hill Book C o , 1914, weekly. Chemiker-Zeitung, Dr. Alfred Huthig Verlag, G m b H , Wilckensstr. 3/5, Heidelberg, Germany, 1876, semimonthly. Chemisch Weekblad, Ν. V . Uitgeverij W. P. van Stockum & Z n , Hartogstraat 3, Box 123, The Hague, Netherlands, 1903, weekly. Chemische Technik, V E B Deutscher Verlag fiir Grundstoffindustrie, Karl-Heine-Str. 27, Leipzig W. 31, Germany, 1949, monthly. Chemisches Zentralblatt, Akademie-Verlag G m b H , Leipziger Str. 3-4, Berlin W8, Germany, 1830, weekly. Chemistry and Industry, Society of Chemical Industry, 14 Belgrave Square, London SW1, England, 1881, weekly. Chimia, H . R. Sauerlander & C o , Laurenzenvorstadt 89, Aarau, Switzerland, 1947, monthly. Chimica e Vlndustria, Societa per Azioni Editrice di Chimica, Piazzale R. Morandi 2, Milan, Italy, 1919, monthly. Chimie et Industrie, Société de Productions Documentaires, 28 rue St.-Dominique, Paris 7 , France, 1917, monthly. Collections of Czechoslovak Chemical Communications, Czechoslovak Acadmy of Science, Na Cricisti 2, Prague 6, Czechoslovakia, 1929, bimonthly. European Chemical News, Temple Press, L t d , Bowling Green Lane, London E C 1 , England, 1962, weekly. European Polymer Journal, Pergamon Press, quarterly. Farm Chemicals, Meister Publishing C o , 37841 Euclid A v e , Willoughby, Ohio 44094, 1894, monthly. Fortschritte der Hochpolymeren-F orschung (Advances in Polymer Science), SpringerVerlag, Heidelberger Platz 3, Berlin-Wilmersdorf (West), Germany, irregular. Gazzetta Chimica Italiana, Viale Liege 48, Rome, Italy, 1871, 9-10 times a year. Helvetica Chimica Acta, Verlag Helvetica Chimica Acta, Box Basil 7, Switzerland, 1918, bimonthly. Hydrocarbon Processing-Petroleum Refiner, Gulf Publishing C o , Box 2608, Houston, Tex. 77001, 1922, monthly. e


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The Industrial Chemist, Tothill Press, L t d . , 33 Tothill St., Westminster, London SW1, England, monthly. Industrial and Engineering Chemistry (plus 3 quarteries: Fundamentals; Process Design and Development: Product Research and Development ), American Chemical Society, 1903, monthly. l'Industrie du Pétrole (formerly l'Industrie du Pétrole et de la Pétrochimie), name changed in 1957 to l'Industrie du Pétrole et Energies Industrielles, which see. l'Industrie du Pétrole et Energies Industrielles (formerly Industrie du Pétrole), S 252 Faubourg St., Honore, Paris 8 , France, monthly. Industriele Eigendom, Octrooiraad en Merkenbureau, Willem Witsenplein 6, The Hague, Netherlands, 3 times a month. Institute of Petroleum Journal, Institute of Petroleum, 61 New Cavendish St., London W l , England, 1914, monthly. Institute of Petroleum Review, 1947, monthly. Institution of Rubber Industry, Transactions and Proceedings, 4 Kensington Palace Gardens, London W8, England, 1925, bimonthly. Journal of Agricultural and Food Chemistry, American Chemical Society, 1953, b i monthly. Journal of the American Chemical Society, American Chemical Society, 1879, monthly. Journal of Applied Chemistry, Society of Chemical Industry, 14 Belgrave Square, London SW1, England, 1951, monthly. Journal of Applied Polymer Science, John Wiley & Sons, 605 Third Ave., New York, Ν. Y. 10016, 1959, bimonthly. Journal of Catalysis, Academic Press, Inc., 1962, bimonthly. Journal of the Chemical Society (includes Proceedings), The Chemical Society, Bur lington House, Piccadilly, London W l , England, 1848, monthly. Journal of Organic Chemistry, American Chemical Society, 1936, monthly. Journal of Petroleum Technology, Society of Petroleum Engineers, A I M E , 6300 North Central Expressway, Dallas, Tex. 75206, 1948, monthly. Journal of Polymer Science (in 3 sections: A, General Papers; B, Polymer Letters; C, Polymer Symposia), Interscience Publishers, 605 Third Ave., New York, Ν. Y. 10016, 1945, monthly. Justus Liebigs Annalen Der Chemie, Verlag Chemie G m b H , 1832, irregular. Khimicheskaya Promyshlennost', Khimiya, N . Krasnoselskaya 37, Moscow B-66, USSR, 1924, monthly. Kunststoffe, Carl Hanser Zeitschriftenverlag G m b H , Kolberger Str. 22, 8000 Munich 27, Germany, 1911, monthly. Makromolekulare Chemie, Huthig & Wepf Verlag, Eisengasse 5, Basel, Switzerland, 1947, irregular. Monthly Catalog of U. S. Government Publications, Superintendent of Documents, Government Printing Office, Washington, D. C. 20402. Neftekhimiya (Petroleum Chemistry, English translation), Pergamon Press, 1962, quarterly. Nippon Kagaku Zasshi (Bulletin of the Chemical Society of Japan), Chemical Society of Japan, No. 5, 1-chome, Surugadai-Kanda, Chiyoda-ku, Tokyo, Japan, 1926, monthly. Nitrogen, British Sulphur Corp., L t d . , 40 Great Titchfield St., London W l , England, 1959, bimonthly. Official Gazette, Superintendent of Documents, 1872, weekly. The Oil and Gas Journal, The Petroleum Publishing Co., 211 South Cheyenne Ave., Tulsa 3, Oklahoma. Organometallic Compounds, Translation and Technical Information Services, 32 Manaton Rd., London SE15, England, 1961, monthly. Petroleum, Grampian Press Ltd., Shepherds Bush Rd., Hammersmith, London W6, England, 1939, monthly. Petroleum Times, Temple Press, L t d . , 1899, semimonthly. Plastics Technology, Bill Brothers Publications, Inc., 630 Third Ave., New York, Ν. Y. 10017, 1955, monthly. Polymer, Butterworth & Co., 88 Kingsway, London W C 2 , England, 1960, monthly. Predicasts, Economic Index and Surveys, Inc., Cleveland, Ohio. Polymer Report, Institute of Polymer Industry, Central P. O. Box 1176, Tokyo, Japan, 1958, monthly. t

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LITERATURE


Preprints, Division of Fuel Chemistry of the American Chemical Society, Dr. R. A . Glenn, Division Director of Publications, c/o Bituminous Coal Research, Inc., 350 Hochberg R d , Monroeville, Pa. 15146, irregular. Preprints, Division of Organic Coatings ir Plastics Chemistry of the American Chemical Society, Mr. Kenneth N . Edwards, Division Secretary, c/o Dunn-EdwardsC o r p , 4885 East 52nd Place, Los Angeles, Calif. 90022, irregular. Preprints, Division of Petroleum Chemistry of the American Chemical Society, Dr. Vladimir Haensel, Division Treasurer, c/o Universal O i l Products C o , 30 Algonquin R d , Des Plaines, 111. 60016, irregular. Proceedings, American Petroleum Institute, annual. Section I, General; Section II, Marketing; Section III, Refining; Section IV, Production; Section V , Transportation; Section V I , Interdivisional. Quarterly Reviews, Chemical Society, 1947, quarterly. Recueil des Brevets d'Invention, Minist. des Affaires Economiques et de l'Energie, Service de la Propriété Industrielle et Commerciale, 19 rue de la L o i Brussels 4, Belgium, 1854, monthly. Recueil des Travaux Chimiques des Pays-Bas, Koninklijke Nederlandse Chemische Vereniging, Burnierstraat 1, The Hague, Netherlands, 1882, monthly. Resins, Rubbers, Plastics, Information for Industry, Inc., 1000 Connecticut A v e , N . W , Washington, D. C. 20036, 1942, semimonthly (discontinued in 1965). Rubber Age, Palmerton Publishing C o , Inc., 101 West 31st S t , New York, Ν. Y. 10001, 1917, monthly. Rubber and Plastics Age, Rubber & Technical Press, L t d , Gaywood House, Great Peter S t , London SW1, England, 1920, monthly. Rubber World, Bill Brothers Publishing C o , 1889, monthly. Rubbers: RAPRA Abstracts (formerly Rubber Abstracts), Rubber and Plastics Research Association of Great Britain, Shawbury, Shrewsbury, Shropshire, England, 1923, monthly. Search, Compendium International Publ. C o r p , Ν. Y. Society of Petroleum Engineers Journal, Society of Petroleum Engineers, A I M E , 1961, quarterly. Soviet Inventions Illustrated (in 3 sections: Chemical Electrical; Mechanical and General), Derwent Publications, L t d , 1963, monthly. SPE Journal, Society of Plastic Engineers, Inc., 65 Prospect S t , Stamford, C o n n , 1945, monthly. SPE Transactions, Society of Plastic Engineers, Inc., 1961, quarterly. Synthetic Organic Chemicals, U. S. Production and Sales, U . S. Tariff Commission, c/o Superintendent of Documents, annual. Uspekhi Khimii (Russian Chemical Reviews), Chemical Society and Department of Scientific and Industrial Research, 1960, monthly. Uniterm Index to Chemical Patents, Information for Industry, Inc., annual. Zhurnal Prikladnoi Khimii, Nauka Mendeleyevskaya Liniya 1, Leningrad V-164, USSR, 1928, monthly. Oxidation Broich, F , "Oxidation Reactions in Petrochemistry," Chem. Ingr. Tech. 34, 45 (1962). Cullis, C. F , "The Controlled Gaseous Oxidation of Organic Compounds," Chem. Ind. (London) 1962, 23. Emanuel, Ν. M , e d , "Oxidation of Hydrocarbons in the Liquid Phase," The Mac millan C o , New York, 1965. Gardner, J . H , Schoenbrun, E. F , "The Partial Oxidation of Ethane," ACS, Div. Petrol Chem. Preprints 3 (2) B57 (1958). Jones, J . H . , Fenske, M . R., "Chemicals from Hydrocarbons by Vapor Phase Oxida tion," ACS, Div. Petrol Chem. Preprints 3 (2) B71 (1958). Landau, R , "Recent Developments in Aromatics Oxidation," Ind. Eng. Chem. 53 (10) 32A (1961). Lundberg, W . O , e d , "Autooxidation and Antioxidants," Vol. 1, Interscience Pub lishers, New York, 1961. Medley, H . D , Cooley, S. D , "Hydrocarbon Oxidation," Advan. Petrol Chem. Re fining 3, 309 (1960). Scott, G , "Atmospheric Oxidation and Autooxidants," Elsevier Publishing C o , New York, 1965.



34.

S C H O E N G O L D

Petroleum

Chemicals

561

"Selective Oxidation Processes," A D V A N . C H E M . SER. No. 51 ( 1964 ). Shtern, V . Ya., "The Gas-Phase Oxidation of Hydrocarbons," The Macmillan Co., New York, 1964. Sittig, M . , "Combining Oxygen and Hydrocarbons for Profits," Gulf Publishing Co., Houston, 1962. Stewart, R., "Oxidation Mechanisms—Applications to Organic Chemistry," W . A . Benjamin Co., New York, 1964. "Symposium on Oxidation to Produce Petrochemicals," A C S , Div. Petrol Chem. Pre prints 5 (2) (I960). Tipson, R. S., "Oxidation of Polycyclic, Aromatic Hydrocarbons—A Review of the Literature," U . S. Department of Commerce, National Bureau of Standards, Wash ington, D. C , 218 refs. Toland, W. G., Lapporte, "Oxidation, Liquid Phase (1959-60) Literature Review," Ind. Eng. Chem. 53, 841 ( 1961 ). /Turney, Τ. Α., "Oxidation Mechanisms," Butterworth & Co., Washington, D. C , 1965. Twigg, G. H . , "Liquid Phase Oxidation by Molecular Oxygen," Chem. Ind. (London) 1962, 4. Waters, W . Α., "Mechanisms of Oxidation of Organic Compounds," John Wiley & Sons, New York, 1964. Wiberg, Κ. B., ed., "Oxidation in Organic Chemistry," Academic Press, New York, 1965. Alkylation Booth, H . S., Martin, D. R., "Boron Trifluoride and its Derivatives," John Wiley & Sons, New York, 1949. Dixon, R. E., Allen, J . G., "Hydrofluoric Acid Alkylation of Paraffins," Advan. Petrol. Chem. Refining 3, 279 ( 1960 ). Egloff, G.^ Huila, G., "Alkylation of Alkanes," Vol. 1, "Patents on Alkylation of Alkanes," Reinhold Publishing Corp., New York, 1948. Jones, Ε. K., "Commercial Alkylation of Paraffins and Aromatics," Advan. Catalysis Related Subjects 10, 165 ( 1958). Kennedy, R. M . , "Catalytic Alkylation of Paraffins with Olefins," Vol. 6 of "Catalysis," P. H . Emmett, ed., Reinhold Publishing Corp., New York, 1958. McAllister, S. H . , "Industrial Applications of Aromatic Alkylation," Brooks Chem. Petrol. Hydrocarbons 3, 579 ( 1955). Olah, G. Α., "Friedel-Crafts and Related Reactions," Interscience Publishers, New York, 1963-65, 4 vols. Praill, P. F. C , "Acylation Reactions: Their Applications and Mechanisms," The Macmillan Co., New York, 1963. Schmerling, L . , "Alkylation of Saturated Hydrocarbons," Brooks Chem. Petrol. Hydro carbons 3, 363 (1955). Topchiev, Α. V . et al, "Alkylation with Olefins," Elsevier Publishing Co., New York, 1964. Topchiev, Α. V . et al, "Boron Trifluoride and its Compounds as Catalysts in Organic Chemistry," Pergamon Press, New York, 1959. Williams, G. H . , "Homolytic Aromatic Substitution," Pergamon Press, New York, 1960. Isomerization Bergman, E . C , "Isomerism and Isomerization of Organic Compounds," Interscience Publishers, New York, 1948. Brooks, B. T., "Isomerization of Olefins," Brooks Chem. Petrol. Hydrocarbons 3, 115 (1955). Condon, F. E., "Catalytic Isomerization of Hydrocarbons," Vol. 6 of "Catalysis," P. H . Emmett, ed., Reinhold Publishing Corp., New York, 1958. Evering, B. L . , "Commercial Isomerization," Advan. Catalysis Related Subjects 6 (1954). "Isomerization and Related Processes," ACS, Div. Petrol Chem. Preprints 4 (2) (1959). Lien, A. P., McCaulay, D. Α., "Friedel-Crafts and Acid Catalysts," ACS, Div. Petrol Chem. Preprints 6 ( 3 ) A101 (1961). ((


562

LITERATURE


Moy, J . A. E , "Catalysts and Chemicals in Refining Operations," Petroleum (London) 25 (5) 150 (1962). Petrov, A. A , "Catalytic Isomerization of Hydrocarbons," National Science Founda tion, Washington, D. C , 1963. Pines, H , "Isomerization of Saturated Hydrocarbons," Brooks Chem. Petrol. Hydro carbons 3, 9 ( 1955 ). Pines, H , Hoffman, Ν. E , "Mechanism of Hydrocarbon Isomerization," Advan. Petrol. Chem. Refining 3, 127 (I960).


Hydrogénation Augustine, R. L , "Catalytic Hydrogénation: Techniques and Applications in Organic Synthesis," M.^Dekker, New York, 1965. Corson, Β. B , "Catalytic Hydrogénation of Hydrocarbons," Brooks Chem. Petrol. Hydrocarbons 3, 283 ( 1955 ). Ellis, C , "Hydrogénation of Organic Substances," 3rd e d , D. Van Nostrand C o , New York, 1930. Emmett, P. H , e d , "Catalysis," Reinhold Publishing C o r p , New York, 1955. Vol. 3— "Hydrogénation and Dehydrogenation"; Vol. 4—-"Hydrocarbon Synthesis, Hydrogénation and Cyclization" ( 1956 ). Friedman, L , et al., "Houdry Dehydrogenation for Olefin Production," Proc. Am. Petrol. Inst. 30 (3), 203 ( 1958). Hagill, J . T , Kerry, F. G , "Hydrogen Recovery and Purification from Refinery OffGas," Proc. Am. Petrol. Inst. 35 (3), 324 ( 1955). Hornaday, G. F , et ah, "Manufacture of Mono- and Diolefins from Catalytic Dehydrogenation," Advan. Petrol. Chem. Refining 4, 451 ( 1961 ). Home, W . A , McAfee, J , "Hydrogénation of Petroleum and Its Fractions," Advan. Petrol. Chem. Refining 3, 192 (1960). Selwitz, C. M , Stanmyer, J . L , Jr., "Dehydrogenation of Pentanes with Oxygen," A C S , Div. Petrol. Chem. Preprints 6 ( 3 ) B141 (1961). Halogenation Belohlav, R. L , McBee, Ε. T , "Halogenation," Ind. Eng. Chem. 53, 1015 (1961). Chiltz, G , et al., "Atomic Chlorination of Simple Hydrocarbon Derivatives in the Gas Phase," Chem. Rev. 63, 355 (1963). De La^Mare, P. B. D , Ridd, J . H , "Aromatic Substitution: Nitration and Halogena tion," Academic Press, New York, 1959. Huntress, Ε. H , "The Preparation, Properties, Chemical Behavior, and Identification of Organic Chlorine Compounds," John Wiley & Sons, New York, 1948. Lovelace, A. M . et al., "Aliphatic Fluorine Compounds," Reinhold Publishing C o r p , New York, 1958. McBee, E. T , Ungnade, H . E , "Chlorination of Paraffins and Cycloparaffins," Brooks Chem. Petrol. Hydrocarbons 3, 59 ( 1955). Pavlath, A. E , Leffler, A. J , "Aromatic Fluorine Compounds," Reinhold Publishing C o r p , New York, 1962. Simons, J . H , "Fluorine Chemistry," 5 vols. Academic Press, New York, 1950-65. Stacey, M . et al., "Advances in Fluorine Chemistry," 5 vols, Butterworth & C o , London, 1960-65. Von Oettingen, W. F , "The Halogenated Hydrocarbons of Industrial and Toxicological Importance," Elsevier Publishing C o , New York, 1962. Nitration Astle, M . J , "Industrial Organic Nitrogen Compounds," Reinhold Publishing C o r p , New York, 1961. Brooks, Β. T , "Nitration of Paraffins and Cycloparaffins," Brooks Chem. Petrol. Hydrocarbons 3, 85 ( 1955 ). McKinney, C. D , Jr., "Nitration of Aromatic Hydrocarbons," Brooks Chem. Petrol. Hydrocarbons 3, 643 ( 1955). Peppel, W . J , Moss, P. H , "Nitriles and Amines," Advan. Petrol. Chem. Refining 4, 369 (1961). Topchiev, Α. V , "Nitration of Hydrocarbons and Other Organic Compounds," transi, by C. Matthews, Pergamon Press, New York, 1959.


34.

S C H O E N G O L D

Petroleum

563

Chemicals


Sulfonation Challenger, F., "Aspects of the Organic Chemistry of Sulfur," Academic Press, New York, 1959. Estep, J . E., et al., "Recovery of Sulfur from Sour Natural and Refinery Gases," Advan. Petrol. Chem. Refining 6, 315 (1962). Folkins, H . O., Miller, E . L . , "Synthesis of Mercaptans," ACS, Div. Petrol. Chem. Preprints 6 ( 3 ) B97 ( 1961 ). Gilbert, Ε. E . , "Sulfonation and Related Reactions," Interscience Publishers, New York, 1965. Gilbert, Ε. E., "Sulfonation of Aromatic Hydrocarbons," Brooks Chem. Petrol. Hydro carbons 3, 611 (1955). Hartough, H . D., "Chemistry of the Sulfur Compounds in Petroleum," Advan. Petrol. Chem. Refining 3, 419 ( 1960). Kharasch, N . , "Organic Sulfur Compounds," Vol. 1, Pergamon Press, New York, 1961. Pryor, W . Α., "Mechanisms of Sulfur Reactions," McGraw-Hill Book Co., New York, 1962. Reid, Ε. E., "Organic Chemistry of Bivalent Sulfur," Vols. 1-6, Chemical Publishing Co., New York, 1958-66. Suter, C M . , "Organic Chemistry of Sulfur," John Wiley & Sons, New York, 1944. "Organic Sulfur Compounds," 2 vols., Pergamon Press, New York, 1961-62. Polymerization American Chemical Society, "Symposium on Copolymers of Alpha Olefins," Division of Polymer Chemistry, 141st Meeting, Washington, D . C , 1962. Basdekis, C. H . , " A B S Plastics," Reinhold Publishing Corp., New York, 1964. Billmeyer, F. W., "Textbook of Polymer Science," Interscience Publishers, New York, 1962. Gaylord, N . G., Mark, H . F., "Linear and Stereoregular Addition Polymers Polymeriza tion with Controlled Propagation," Interscience Publishers, New York, 1959. Guterbock, H . , "Polyisobutylen und Isobutylen-Mischpolymerisate," Springer-Verlag, Berlin, 1959. Hagen, H . , "Polyàthylen und Andere Polyolefine," 2nd éd., B. Garrels, Hamburg, 1961. Kresser, T. O. J., "Polyethylene," Reinhold Publishing Corp., New York, 1957. Kresser, T. O. J., "Polypropylene," Reinhold Publishing Corp., New York, 1960. Mark, H . F. et al, "Encyclopedia of Polymer Science and Technology: Plastics, Resins, Rubbers, Fibers," Interscience Publishers, New York, 1964. Marvel, C. S., " A n Introduction to the Organic Chemistry of High Polymers," John Wiley & Sons, New York, 1959. McMahon, J . F., et al, "Polymerization of Olefins as a Refinery Process," Advan. Petrol Chem. Refining 7,285 (1963). "Progress in High Polymers," Vol. 1, Academic Press, New York, 1961. Raff, R. Α. V., "Crystalline Olefin Polymers," Interscience Publishers, New York, 1964. Raff, R. Α. V., Allison, J . B., "Polyethylene," Interscience Publishers, New York, 1956. Renfrew, Α., Morgan, P., "Polythene: The Technology and Uses of Ethylene Poly mers," 2nd éd., Interscience Publishers, New York, 1960. Sittig, M . , "Polyolefin Processes Today," Petrol. Refiner 39 (11) 162 (1960). Sittig, M . , "Polyolefin Resin Processes," Gulf Publishing Co., Houston, 1961. Tanford, C., "Physical Chemistry of Macromolecules," John Wiley & Sons, New York, 1961. Topchiev, Α. V., Krentsel, Β. Α., "Polyolefines," transi, from Russian* Pergamon Press, New York, 1962. Whittington, L . R., ed., " A Guide to the Literature and Patents Concerning Polyvinyl Chloride," 2nd ed., Society of Plastic Engineers, Stanford, Conn., 1963. tt

U.S. Patent Classes The following are the main classes of U . S . patents w h i c h are concerned with petrochemicals. These are purely representative, and if a search is desired, it is essential that the " M a n u a l of Classification be consulted. ,,


564

LITERATURE OF CHEMICAL

TECHNOLOGY

Cfoss


18 23 71 106 117 196 204 208 252 260

Plastics Chemistry Chemistry—fertilizers Compositions, coating or plastic Coating: processed and miscellaneous products Chemistry, fermentation Chemistry, electrical and wave energy Mineral oils: processes and products Compositions Chemistry, carbon compounds

A n essential tool i n using the Patent Office Classification M a n u a l is the recently published (1966) book entitled, "Development and Use of Patent Classification Systems." This was published by the U . S . Department of C o m merce and is available from the Superintendent of Documents, U . S . Government Printing Office, Washington, D . C . 20402, for $1.50. It provides details and illustrations on how the U . S . Patent Classification Systems are presently organized, on bases and techniques used i n developing and administering the systems, and includes instructions for using the systems. RECEIVED November 4, 1 9 6 6 . Updated 1 9 6 8 .


Literature Resources for Petroleum Chemicals - ACS Publications

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