Commercial Development of Hydrocarbons From Petroleum and

Commercial Development of Hydrocarbons From Petroleum and Natural Gas GUSTAV EGLOFF, MARY ALEXANDER, and CATHERINE ZIMMER

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Universal Oil Products Co., Des Plaines, Ill.

The literature of the commercial development of hydrocarbons derivable from petroleum and natural gas is meager until about 1935. Since 1945, the literature has become extensive. This study includes the paraffins, olefins, alicyclics, aromatics, acetylene, and separation processes. Journals and sections of journals of value are discussed. The main subject heads to be consulted in Chemical Abstracts are given. There is considerable overlapping of subject matter in the U. S. patent classification system; pertinent classes are listed. References in the bibliography were selected to show the various types available.

T h e quantity of literature available on the commercial development of hydrocarbons from petroleum and natural gas is indicative of the increasing interest in this subject as well as of the vast expansion of the petrochemical industry over a period of relatively few years. Published information on the commercial development is meager until about 1935. During the late thirties, the growing interest i n hydrocarbons which have high wartime significance became apparent. During the war, publications on these hydrocarbons i n creased, but the information therein is somewhat limited because of security regulations. Since 1945, the literature has become extensive on manufacture, separation, and purifica tion of a l l classes of hydrocarbons produced commercially. While the primary interest immediately after the war was i n the field of aliphatics, producing aromatics began to receive increasing attention, and the literature since 1950 has been voluminous. The present study of the literature includes that relating to the paraffins of which pro pane and the butanes are the principal commercial products for manufacture of chemicals, to olefins of which ethylene and butadiene are most important, to alicyclics, to aromatics of which toluene, benzene, and the xylenes are of commercial interest, to acetylene, and to separation processes.

Paraffins The commercial production of propane and the butanes has been the subject of tech nical articles since the beginning of the liquefied petroleum gas industry i n the early 1920's. The number of articles appearing has increased with advances i n technical knowledge. M o s t of these articles relate to the design and operation of natural gasoline plants and recovery of the gases therefrom. M u c h information is also available i n articles on sepa ration processes. Isobutane, which is present i n comparatively small quantities i n natural gas, was produced b y isomerization of normal butane during W o r l d War I I . The isomerization processes have been discussed i n the literature, and descriptions of them are still given i n the process sections of some oil journals. Selected references are given under Propane-Butanes i n the bibliography. 360

LITERATURE RESOURCES Advances in Chemistry; American Chemical Society: Washington, DC, 1954.

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There is very little information i n the literature on commercial production of the indi vidual higher paraffins. A number of these, however, are marketed b y petroleum com panies for use i n research, and announcements of their availability are made i n the oil journals. References to these compounds are listed under Paraffins, Miscellaneous.


Olefins Although utilized for chemical manufacture i n some short-lived ventures prior to World War I and continuously since the early 1920's, ethylene manufacture and separation were the subjects of relatively few publications outside of patents before the end of W o r l d War I I . Since that time numerous articles have been published on ethylene production by cracking C2-C3 gas fractions and selected oil fractions and on its separation b y adsorp tion processes. Its production is the greatest of any of the hydrocarbons from petroleum, and much literature is available on its utilization. A selected list of references is given i n the bibliography under Ethylene. Inasmuch as sufficient quantities of propylene to meet demands have been available from conventional thermal and catalytic cracking processes and from ethylene manufac ture, there is very little literature on the specific subject of propylene manufacture. I n formation on its extraction is to be found i n articles on separation processes. The buty lènes are also obtained as by-products of conventional cracking, but the large demand for them for gasoline and synthetic rubber brought about the commercial development during W o r l d War I I of dehydrogenation processes for their production. Selected ref erences to the butylènes and propylene are cited under Olefins, Miscellaneous i n the bibliography. W i t h the advent of the synthetic rubber industry at the beginning of W o r l d W a r I I , articles began to appear on the commercial production and separation of butadiene. Articles on the progress of butadiene production appeared, but security regulations limited the amount of technical information given. M o r e specific information was d i vulged after the war, and improvements i n the processes, catalysts used, and equipment continue to appear i n the literature. Selected references are listed under Butadiene i n the bibliography.

Alicyclics There is very little information available on the commercial production of pure cycloparaffins. Although feed stocks composed of this class of hydrocarbons are used i n the manufacture of aromatics, chemical-grade cycloparaffins have not been produced ex tensively. Highly purified cyclohexane is being used in production of nylon. References to the cycloparaffins are listed under Miscellaneous.

Aromatics Toluene was produced commercially from petroleum during W o r l d War I at the rate of 3,000,000 pounds per month, and a limited number of articles on its production appeared during this period. N o chemical grade aromatics were produced from that time until World W a r I I , when large scale commercial production was initiated to meet requirements for T N T . B o t h the extractive process and the catalytic reforming processes used were discussed in the literature. Its production by the newer catalytic reforming processes has been discussed recently. References are listed under Toluene. Although chemical-grade benzene was not produced commercially prior to 1949, potential interest became increasingly apparent after the end of W o r l d War I I . W i t h the unprecedented demands brought about b y the Korean War and the rapid growth of such markets as plastics, detergents, and nylon, commercial production was rapidly increased. The major portion of petroleum benzene is produced b y the newer catalytic reforming processes such as platforming and an increasing number of articles have been appearing since 1950 on this subject. The separation and purification of petroleum-produced ben zene has also necessitated new adsorption and extraction processes which are discussed in the literature. Selected references are listed under Benzene. LITERATURE RESOURCES Advances in Chemistry; American Chemical Society: Washington, DC, 1954.


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The commercial utilization of o-xylene for phthalic anhydride i n 1945, of p-xylene for synthetic fibers more recently, and the numerous applications of isophthalic derivatives from m-xylene have brought about intense interest i n the production and separation of the xylenes. These compounds are produced by the catalytic reforming processes used for benzene and toluene and are discussed in articles on these processes. Fractionation proc esses for separation of o-xylene and fractional crystallization for separation of p-xylene are discussed i n the recent literature. References to the xylenes are listed under A r o matics, Miscellaneous. The commercial production of styrene attained high importance during W o r l d W a r II i n connection with the synthetic rubber program, and demands have continued to increase because of new developments i n and requirements for plastics. T h e literature appearing during the war was limited b y the security regulations, but rather extensive i n formation i n aviation gasoline, was another hydrocarbon of importance during the war. It was not produced for a number of years thereafter, but interest has recently been re newed because of its utilization i n a process for making phenol and acetone simultaneously. The literature to date on its manufacture is rather sparse, although considerable has been published on its utilization. References to styrene and cumene appear under Aromatics, Miscellaneous.

Acetylene Although much has been published over the past 30 years i n reference to semicommercial production of acetylene from methane, acetylene has only recently been produced commercially from natural gas i n the United States. After the cessation of hostilities i n Europe i n 1945, a number of articles were published on production i n Germany. While only the Huels plant utilized natural gas and for only a short time, the technical infor mation is applicable. These articles were based on P B (Publication Board), or T I I C (Technical Industrial Intelligence Committee) and F I A T (Field Information Agency, Technical) and B I O S (British Intelligence Objectives Subcommittee) reports which should be consulted i n any extensive study of the subject. A n increasing number of articles is appearing on commercial production i n the United States, and on separation processes which are of primary importance i n successful commercial production. A number of recent articles discuss the utilization of acetylene and compare it with ethylene as a starting material for chemical products. Selected references appear under Acetylene.

Separation Processes It should be emphasized that the development of separation processes has, to a large extent, made possible production of the hydrocarbons from petroleum and natural gas. Large volumes of many of these hydrocarbons are naturally present i n the raw materials or i n the gases produced b y refining operations, and separation is the only problem. F o r those hydrocarbons requiring special manufacturing processes such as benzene and acety lene, processes for purification are also necessary. Separation process articles are listed under Separation Processes i n the bibliography except for those articles which relate to only one compound.

Types of Information Available The types of information on hydrocarbons from petroleum and natural gas vary widely. The patent literature on manufacture and separation of the hydrocarbons is voluminous. Articles i n chemical, engineering, and oil journals include reviews, descrip tions of processes, descriptions of entire plants, discussions of construction materials for these plants, discussions of the adaptation of conventional facilities for production of specific hydrocarbons, discussions of utilization, enumeration of plants operating, analyses of present requirements, and predictions of future demands. M a n y of these journals also publish news items announcing the availability of new hydrocarbons and the construction of new plants. Recently a number of journals have established the practice of publishing staff reports on a specific product or group of products. These give the present status LITERATURE RESOURCES Advances in Chemistry; American Chemical Society: Washington, DC, 1954.


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of processes from a technical standpoint and often discuss the economics of various proc esses and utilization of the product. Although the actual technical information included is brief, good comparisons of processes and source materials are often found i n this type of article. The selected references listed under the names of individual hydrocarbons, classes of hydrocarbons, and Separation Processes are principally articles giving technical informa tion on processes and plant design and the staff-report type of review. Some articles have been included because of their historical significance i n the long-range development of modern processes. The amount of detail given i n the technical articles varies. I n general, simplified flow diagrams, operating conditions, specifications on starting materials, analyses of products, and a discussion of various phases of the process are included. I n some instances a discussion of plant costs, uses, and historical background is also given. Articles relating to pilot plant operation of processes which have been commercialized are cited as well as those on full scale operation. Under Review Articles, some compre hensive reviews of various phases of the production of hydrocarbons from petroleum are cited. A number of these are particularly valuable because of the lengthy bibliog raphies which have been included.

Principal Journals The principal journals i n which information on the commercial production of hydro carbons from petroleum and natural gas is found include Industrial and Engineering Chemistry, Chemical Engineering, Chemical Engineering Progress, Chemical and Engineering News, Chemical Week, Petroleum Processing, Petroleum Refiner, Oil and Gas Journal, and Petroleum Engineer. Articles and news items also appear frequently i n Petroleum World and World Petroleum, the Proceedings of the Amencan Petroleum Institute, gas journals such as LP Gas and the American Gas Association Monthly, and publications of some private companies such as Heat Engineering and the Standard Oil of California Technical Review. The chemical engineering journals have carried rather complete descriptions of most of the processes used i n the manufacture and separation of hydrocarbons. Articles i n Industrial and Engineering Chemistry and Chemical Engineering Progress very frequently contain a discussion of theoretical considerations and engineering calculations. Industrial and Engineering Chemistry has published a U n i t Operations Review section, which re views the status of processes used for hydrocarbons as well as for other chemicals, annually since January, 1946. Chemical Engineering Progress includes the discussions of papers at American Institute of Chemical Engineers' meetings which often bring out interesting details. Chemical Engineering (Chemical and Metallurgical Engineering prior to August, 1946) publishes a special type of articles called the Commodity Survey on specific prod ucts. These evaluate different processes used i n production and the markets for a given product. The news magazines publish announcements of plants, which include such infor mation as location, processes used, cost of plant, and date of initial production. I n Chemical and Engineering News, the latest items are usually found under " c o n C E N t r a t e s . " This magazine publishes, in addition to news items and articles of general interest i n the petrochemical field, excellent staff reports on the technical and economic status of various products of widespread interest at the time. Chemical Week (Chemical Industries Week prior to June, 1951 and Chemical Industries prior to January 20, 1951) is one of the best magazines for keeping up-to-date on the commercialization of new processes. The articles therein usually include only brief technical descriptions of plants, and discussion is usually concerned with the significance of processes and products. The technical type of articles which appeared i n Chemical Industries are now carried b y Chemical Engineering. The oil journals carry both news items and technical articles. The technical articles frequently relate to the operations i n a specific plant rather than to the general operation of the process. These journals also carry timely staff reports on products and processes which are particularly good from a comparative viewpoint. Petroleum Processing (Section R of National Petroleum News prior to 1946) now has a Petrochemical Processing LITERATURE RESOURCES Advances in Chemistry; American Chemical Society: Washington, DC, 1954.

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Section, which appears every month. I t also has a special section on Patents which lists new patents according to their classification. The Process Issue of the Petroleum Refiner is now carrying a special section on Petrochemical Processes. I n the September 1952 issue for example, Extractive Distillation for Aromatic Recovery, Modified S 0 Extraction for Aromatic Recovery, Udex Extraction, Ethylene Manufacture b y Cracking, Ethylene Production, Hypersorption, Hydrocol, Dehydrogenation (for butadiene), and Butadiene Process, were described. These descriptions include the main essentials of the process, simplified flow diagrams, and the name of the company offering it. Formerly these proc esses were described under the Process Section. The Oil and Gas Journal carries a process section i n its A n n u a l Refinery Number under the Annual Refining Section-Processing Details. M o s t of the processes i n current use can be found i n these special sections. The Oil and Gas Journal has recently been carrying a special type of article called Petrochem Report which usually gives a timely discussion of specific commercial plants. I n the Petroleum Engineer, articles on hydrocarbons from petroleum and natural gas are found under Section C, Refining and Gas Processing. This journal publishes a Reference Annual which usually contains more technical articles on hydrocarbon production than do other issues. European developments are covered i n the Petroleum Times, Petroleum (London), and the Institute of Petroleum Review. Canadian Chemical Processing is carrying an increas ing number of articles as a result of the rapidly growing petrochemical industry and the vast new petroleum and gas fields which have been discovered in that country. There are many Japanese and Russian articles referring to possible commercial production of h y drocarbons from petroleum. I n the case of Russian references, it is not known whether processes described have actually been used commercially. Because of the relative newness of the petrochemical industry, very few books have been published which have chapters on the commercial development of hydrocarbons from petroleum and natural gas. A list of miscellaneous books and pamphlets of interest is given i n the bibliography.


2

Indexes N o attempt will be made to outline a clear-cut index-to-article procedure inasmuch as individual searches will vary with the specific information wanted and will require some ingenuity on the part of the searcher. In reviewing the literature for the present paper, about 600 references were considered. These were located b y checking Chemical Abstracts Indexes, bibliographies prepared for the use of our research men, clipping files maintained b y our library staff, and perusal of the tables of contents of recent issues of chemical engineering and oil journals. I t is also help ful to check the author indexes for the names of the principal contributors to a given field and to look into the publications of private companies which are available i n some libraries. I n searching the subject indexes to Chemical Abstracts, the main subject headings to be consulted are chemicals; gases; gas, fuel; gas, natural; gasoline; hydrocarbons; the i n dividual hydrocarbons—i.e., acetylene, benzene, butadiene, butane, butene, and toluene; oils; petroleum refining, and the processes—i.e., adsorption, alkylation, distillation, fractionation, isomerization, and polymerization. There are many subheadings under each of these general subject headings. I n general, the subheadings, 'formation of," and "preparation of," refer to laboratory syntheses. Under "manufacture of" and "sepa ration of" individual compounds or classes of hydrocarbons, references are mainly to patents. Petroleum refining is perhaps the most important main heading i n Chemical Abstracts to be consulted if a comprehensive but nonexhaustive search is being made. The sub headings "cracking- to aromatic and saturated hydrocarbons," "gas manufacture," "gases from," and "reviews" are important. Under "gases f r o m " the headings are more specific—"fuels and chemicals for petroleum industry," "hydrocarbon extraction i n liquid phase from," "hydrocarbon recovery from," " C H recovery therefrom," "olefin recovery from," " C H recovery from," "purification of," "pyrolysis and polymerization," and "sepn." 1

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3

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When investigating the abstracts, an article should not be eliminated on the basis of a title alone for these are often deceptive. F o r example an article entitled " T h e U t i l i zation of Benzene" may contain detailed information on its commercial production. A n article entitled " X Y Z Company produces 180,000,000 million lbs. of ethylene" may simply be an announcement that the plant is operating, but again, it may contain a highly de tailed description of the plant itself, construction materials used therein, and results of operations. " M o r e Propane Recovery" may be merely a half-column story stating that more propane is being recovered from a specific plant, but i t could also be a highly tech nical article on how the result is accomplished.

U. S. Patent Classes The principal United States patent classes which should be searched i n a survey of the manufacture of paraffinic, olefinic, and aromatic hydrocarbons include the main classes 196, mineral oils, and 260, chemistry, carbon compounds. There is considerable over lapping of subject matter i n the United States patent classification system because no attempt is made to cross index or cross file patents on many different topics. The classes suggested for search will many times contain a great deal of subject matter which is not pertinent to the search being conducted. F o r example class 196 has about 50 subclasses dealing with distillation of petroleum, and at the same time class 202 deals with distillation from a broad standpoint. Similarly many cracking processes are directed to olefin and aromatic production and many subclasses of class 260 are directed to hydrocarbon pro duction b y thermal or catalytic processes. The United States patent classification is rather inflexible and much cross searching is necessary to find a l l of the patents on any given subj ect. This is illustrated b y the following pertinent classes. I.

Lower Paraffins

Class 196, Mineral oils Subclasses 7, Mineral oils from hydrocarbons gases 11, Weathering or rectification of "wild gasoline" 47-70, Distillation, vaporizing processes, with cracking 61, Vapor phase cracking 71, Distillation without cracking Class 260, Chemistry, carbon compounds Subclasses 676, Acyclic 683.4, Alkylation or condensation 683.5, Isomerization 683.6, Hydrogénation II.

Lower Olefins

Class 196, Mineral Oils · Subclasses 47-70, Distillation, vaporizing processes, with cracking 52, With Catalysts Class 260, Chemistry, carbon compounds Subclasses 677, Acyclic, unsaturated 678, Acyclic, unsaturated, triple bond 679, Acetylene 680, Diolefins, including butadiene 683.3, by dehydrogenation 676, dehydrogenation process III.

Aromatic Hydrocarbons

Class 196 Subclasses 47-70, Cracking processes Class 260, Chemistry, carbon compounds Subclasses 668, Aromatic 671, Alkylation 671, Alkylation 672, Dealkylation 673, From acyclic hydrocarbons 673.5, Six or more C Atoms in Molecule 669, Vinyl, styrenes 674, Purification or recovery IV.

Hydrocarbon Solvents

Class 196, Mineral oils Subclass 14.46, Hydrocarbon solvents Class 252, Compositions Subclass 364, Solvents



366 V. Azeotropic Distillation Class 202, Distillation Subclasses 41, Two component 42, Azeotropic mixtures VI. Sorption Processes

Class 196, Mineral oils Subclasses 4, Dehydration with chemicals, adsorbent, orfilteringmaterial 147, Treatment withfilteringmaterial


Bibliography A list of patents has not been given in the bibliography inasmuch as specific searches would be necessary for any project. In selecting articles for the bibliography, an attempt was made to represent the various types of information available. News items, however, have not been cited. Some references are included on processes which have been offered but have never been put into operation and on processes which have been in commercial operation but are currently not being used. Under miscellaneous headings, the specific subject matter is noted after the reference unless the article includes discussion of a number of hydrocarbons or processes. Bibliography ACETYLENE

Aries, R. S., and Cziner, R. M., Petroleum Refiner, 31, 127 (May 1952). Chem. Inds. Week, 68, 17 (April 28, 1951). Hasche, R. L., Chem. Met. Eng., 49, 78 (July 1942). Ibid., 52, 116 (October 1945). Monrad, C. C., Chem. Eng., 53, 120 (July 1946). Natl. Petroleum News, 34, R270 (Aug. 26, 1942). Ibid., 37, R865 (Nov. 1945). Ibid., p. R866. Petroleum Processing, 3, 215 (1948). Pettyjohn, E. S., Natl. Petroleum News, 38, R596 (Aug. 1946). Ruebensaal, C. F., Chem. Eng., 59, 159 (November 1952).

AROMATIC MISCELLANEOUS

Chem. Eng., 58, 305 (February 1951). Xylenes. Chem. Inds. Week, 68, 17 (March 31, 1951). Xylenes. Chem. Met. Eng., 50, 133 (June 1943). Styrene. Chem. Week, 70, 35 (April 19, 1952). p-Xylene. Corlew, R. P., and Deeler, W. F., Calif. Oil World, 37, 34 (October 1944). Cumene. Dow, W., Ind. Eng. Chem., 34, 1267 (1942). Styrene. Haensel, V., Oil Gas J., 50, 80 (Aug. 9, 1951). Haensel, V., and Berger, C. V., Petroleum Processing, 6, 264 (1951). Hall, E. L., Chem. Met. Eng., 48, 100 (September 1941). Heineman, H., Scholl, J. W., and Stevenson, D. H., Petroleum Engr., 23, C40 (November 1951). Marshall, C. H., Chem. Eng. Progr., 46, 313 (1950). McAllister, S. H., Anderson, J., and Bullard, E. F., Ibid., 43, 189 (1947). Cumene. Mitchell, J. E., Jr., Trans. Am. Inst. Chem. Engrs., 42, 293 (1946). Styrene. Oil Gas J., 45, 155 (October 19, 1946). Petroleum Processing, 7, 839 (1952). Read, D., Oil Gas J., 51, 82 (June 23, 1952). Williams, C. R., and Sutherland, R. E., Ibid., 50, 84 (August 9, 1951).

BOOKS AND PAMPHLETS

ADVANCES IN CHEM. SER., NO. 5 (1951). Progress in Petroleum Technology. Berl, E., "Production of Toluene and TNT from Natural Oil by Extraction," No. 35, New York, Berliner, 1942. Bergmann, E. D., "The Chemistry of Acetylene and Related Compounds," New York, Inter science Publishers, 1948. Brown, G. G., Katz, D. L., Oberfell, G. G., and Alden, R. C., "Natural Gasoline and Volatile Hydrocarbons," Tulsa, Natural Gasoline Association of America, 1948. Burke, O. W., Jr., Starr, C, E., Jr., and Tuemmler, F. D., "Light Hydrocarbon Analysis," Chapter 2 of "Butadiene Production Processes," Committee on Butadiene Specifications and Method of Analysis, New York, Reinhold Publishing Corp., 1951. Ellis, C., "The Chemistry of Petroleum Derivatives," New York, The Chemical Catalog Co., 1934. Goldstein, R. F., "The Petroleum Chemicals Industry," New York, John Wiley & Sons, 1950, LITERATURE RESOURCES Advances in Chemistry; American Chemical Society: Washington, DC, 1954.

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Groggins, P. H., "Unit Processes in Organic Synthesis," 2nd ed., New York, McGraw-Hill Book Co., 1938. Institute of Petroleum, Manson House, London. "Reviews of Petroleum Technology," Vol umes 1-11, 1937-49. Japour, M. J., "Petroleum Refining and Manufacturing Processes," Los Angeles, Wetzel Pub lishing Co., 1939. Nelson, W. L., "Petroleum Refinery Engineering," 3rd ed., New York, McGraw-Hill Book Co., 1949. Sachanen, A. N., "Conversion of Petroleum," 2nd ed., New York, Reinhold Publishing Corp., 1948. Stephens, M. M., "Petroleum and Natural Gas Engineering," Vol. 1, State College, Pa., Pennsyl vania State College, 1941. BENZENE

Chem. Eng. News, 28, 3866 (1950). Ibid., 29, 761 (1951). Chem. Week, 69, 15 (September 29, 1951). Nelson, W. L., Oil Gas J., 41, 234 (November 12, 1942). Sullivan, F. W., Jr., Chem. Eng. News, 25, 2000 (1947). Thornton, D. P., Jr., Petroleum Processing, 7, 498 (1952). Weber, G., Oil Gas J., 48, 40 (April 3, 1950). World Petroleum, 22, 72 (November 1951).

BUTADIENE

Boyd, 4. H., Ind. Eng. Chem., 40, 1703, 1964 (1948). Chem. Met. Eng., 50, 103 (July 1943). Egloff, G., and Huila, G., Oil Gas J., 41, 40 (November 5, 1942). Ibid., p. 228 (November 12). Ibid., p. 41 (November 19). Ibid., p. 124 (November 26). Ibid., p. 36 (December 3). Ibid., p. 45 (December 10). Ibid., p. 36 (December 17). Ibid., p. 35 (December 24). Elder, A. L., Ind. Eng. Chem., 34, 1260 (1942). Frolich, P. K., and Morrell, C. E., Chem. Eng. News, 21, 1138 (1944). Kearby, Κ. K., Ind. Eng. Chem., 42, 295 (1950). Kratochvil, Κ. V., and Berger, D. E., Petroleum Processing, 7, 1294 (1952). Masser, H. L., Oil Gas J., 42, 45 (October 28, 1943). Natl. Petroleum News, 34, R249 (August 26, 1942). Petroleum Processing, 6, 808 (1951). Petroleum Refiner, 21, 359 (1942). Ibid., p. 365. Ibid., 23, 170 (October 1944). Resen, F. L., Oil Gas J., 51, 149 (November 10, 1952). Russel, R. P., and Murphree, Ε. V., Petroleum Refiner, 23, 186 (December 1944). Thayer, C. H., Lederer, E. R., and Lassait, R. C., Chem. Met. Eng., 49, 116 (November 1942).

ETHYLENE

Buell, C. K., and Weber, L. J., Petroleum Processing, 5, 266, 387 (1950). Curme, G. O., Jr., Chem. Met. Eng., 25, 907 (1921). Deanesly, R. M., and Watkins, C. H., Chem. Eng. Progr., 47, 134 (1951). Eastwood, S. C., and Potas, Α. Ε., Petroleum Engr., 19, 43 (August 1948). Foster, A. L., Ibid., 23, C3 (September 1951). Kehde, H., Fairfield, R. G., Frank, J. C., and Zahnstecher, L. W., Chem. Eng. Progr., 44, 575 (1948). King, C. C., and Warburton, J., Oil Gas J., 51, 92 (December 8, 1952). King, C. C., and Warburton, J., Petroleum Processing, 7, 1644 (1952). Kniel, L., and Slager, W. H., Chem. Eng. Progr., 43, 335 (1947). Kuhn, W. E., and Hutcheson, J. W., Petroleum Processing, 6, 1101 (1951). Nugey, A. L., Refiner Natural Gasoline Mfr., 11, 547 (1932). Petroleum Refiner, 26, 210 (April 1947). Ibid., 30, 123 (July 1951). Ibid., p. 226 (September 1951). Schutt, H. C., Chem. Eng. Progr., 43, 102 (1947). Sherwood, P. W., Petroleum Refiner, 30, 220 (September 1951). Ibid., p. 157 (November 1951). Ibid., 31, 126 (January 1952).

MISCELLANEOUS

Bean, T. H., and Vener, A. L., Oil Gas J., 48, 307 (May 19, 1949). Crawford, C. C., Chem. Inds., 59, 469 (1946). LITERATURE RESOURCES Advances in Chemistry; American Chemical Society: Washington, DC, 1954.



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Frolich, P. K., and Wiesevich, P. J., Ind. Eng. Chem., 24, 13 (1932). Frost, H. N., Petroleum Refiner, 29, 95 (February 1950). Solvent naphthas. Ibid., p. 137 (April 1950). Solvent naphthas. Jones, H. H., and Cox, J. T., Jr., Chem. Eng., 57, 110 (July 1951). Latta, J. E., and Walker, S. W., Chem. Eng. Progr., 44, 173 (1948). CO+H 2 . Nelson, W. L., Oil Gas J., 41, 165 (June 25, 1942). Norman, H. S., Ibid., p. 170. Oil Gas J., 51, 102 (Sept. 1, 1952). Ibid., p. 114 (Sept. 8). Ibid., p. 98 (Sept. 15). Ibid., p. 174 (Oct. 20). Petroleum Processing, 7, 509 (1952). Refiner Natural Gasoline Mfr., 17, No. 6, 44 (1938). Alicyclics. Resen, F. L., Oil Gas J., 51, 62 (June 30, 1952). Ibid., p. 122 (July 14). Ibid., p. 68 (July 21). Ibid., p. 97 (Aug. 11). Ibid., p. 102 (Aug. 25). Ryan, P., Petroleum Refiner, 24, 130 (April 1946). CO+H 2 . Turner, Α. Α., Killmar, Η. M., and Brown, P. W., Chem. Eng. Progr., 48, 281 (1952). Van Winkle, M., Petroleum Refiner, 29, 226 (September 1950). OLEFINS, MISCELLANEOUS

Aries, R. S., and Copulskey, W., Oil Gas J., 49, 54 (July 6, 1950). Arnold, P. M., Ibid., 44, 87 (July 7, 1945). Isobutylene. Chem. Eng., 57, 314 (May 1950). Butylenes. Egloff, Gustav, Oil Gas J., 43, 157 (July 29, 1944). Irvine, V. C., Petroleum Processing, 7, 46 (1952). Propylene. McConnell, Ε. B., Natl. Petroleum News, 35, R562 (December 1943). Butylenes. Natl. Petroleum News, 36, R576 (Sept. 6, 1944). Butylenes. Resen, F. L., Oil Gas J., 50, 160 (Feb. 25, 1952). Polybutenes. Ibid., 51, 62 (June 23, 1952).

PARAFFINS, MISCELLANEOUS

Alden, R. C., Natl. Petroleum News, 32, R234 (June 1940). Neohexane. Ames, C. B., and Tabbert, T. D., Petroleum Refiner, 28, 117 (May 1949). Ethane. Heitz, R. G., Oldershaw, G. F., Brown, W. E., and Barnard, R. D., Ind. Eng. Chem., 41, 1540 (1949). Ethane. Hogan, J. J., Oil Gas J., 51, 86 (June 9, 1952). Ethane, propane. Natl. Petroleum News, 38, 57 (Oct. 16, 1946). Iso-octane. Oberfell, G. G., and Frey, F. E., Oil Gas J., 38, 50 (Nov. 23, 1939). Ibid., p 70 (Nov. 30). Neohexane. Oil Gas J., 45, 122 (September 28, 1946). Isooctane. Resen, F. L., Ibid., 298 (September 29, 1952). Methane, natural gas. World Petroleum, 11, 48 (October 31, 1940). Ann. Refinery Issue. Neohexane.

PROPANE-BUTANES

Albright, J. C., Refiner Natural Gasoline Mfr., 11, 491 (1932). Propane. Alden, R. C., Oil Gas J., 41, 59 (April 29, 1943). n-Butane. Alden, R. C., Refiner Natural Gasoline Mfr. 13, 208 (1934). Butanes. Ambrose, Z. C., Petroleum Engr., 20, 220 (December 1948). Propane. Bell, F. W., Petroleum Refiner, 24, 227 (1945). Propane. Coulthurst, L. J., Natl. Petroleum News, 33, R403 (December 1941). Isobutane. Davis, W. J., Petroleum Engr., 17, 103 (April 1946). Gilmore, F. E., and Bauer, R. D., Petroleum Engr., 23, C-26 (December 1951). Propane. Glendening, A. S., and Sanderson, C. F., Petroleum Processing, 4, 519 (1949). Propane. Gross, L., and Wells, C. T., Petroleum Refiner, 30, 115 (February 1951). Kniel, L., Petroleum Engr., 21, Reference Annual, C-45 (July 1, 1949). Propane. Kniel, L., Petroleum Refiner, 27, 588 (1948). Propane. Mayer, W. T., Petroleum World, 28, 27 (July 1931). Butanes. Norman, H. S., Oil Gas J., 36, 28 (July 1, 1937). Ibid., 42, 201 (Dec. 30, 1943). Isobutane. Petroleum World, 33, No. 4, 36 (1936). Butanes. Short, Ε. H., Jr., Oil Gas J., 42, 67 (March 16, 1944). Stanley, C. P., Ibid., 48, 157 (April 20, 1950). Propane. Thomas, R. W., and Setrum, Ο. M., Ibid., 27, 330 (October 18, 1928). Thornton, D. P., Jr., Petroleum Processing, 3, 1052 (1948). Propane. Ibid., 4, 519 (1949). Propane. Turner, S. D., and Rubey, A. C., Chem. Met. Eng., 45, 362 (1938).

REVIEW ARTICLES

Born, S., Oil Gas J., 35, 124 (May 21, 1936). LITERATURE RESOURCES Advances in Chemistry; American Chemical Society: Washington, DC, 1954.

EGLOFF, ALEXANDER, AND ZIMMER—COMMERCIAL DEVELOPMENT OF HYDROCARBONS

369

Bramston-Cook, H. E., Petroleum Processing, 7, 1145 (1952). Duff, D. M., Oil Gas J., 48, 62 (May 12, 1949). Ellis, C., Ind. Eng. Chem., 26, 826 (1934). Foster, A. L., Oil Gas J., 44, 83 (May 4, 1946). Haensel, V., and Sterba, M., Ind. Eng. Chem., 44, 2073 (1952). Kiddoo, G., Chem. Eng., 59, 149 (September 1952). Meyer, R. E., Chem. Eng. News, 28, 1906 (1950). Murphree, Ε. V., Ind. Eng. Chem., 35, 623 (1943). Simard, R., Chemistry & Industry, 15, 520 (1937). Ziegenhain, W. T., Oil Gas J., 39, 22 (October 31, 1940). Ibid., 41, 185 (June 25, 1942). Downloaded by UNIV OF CALIFORNIA SANTA BARBARA on June 12, 2016 | http://pubs.acs.org Publication Date: June 17, 1954 | doi: 10.1021/ba-1954-0010.ch038

SEPARATION PROCESSES

Albright, J. C., Natl. Petroleum News, 29, R9 (1937). Absorption. Bailey, W. Μ. Α., Jr., Bannerot, R. Α., Fetterly, S. C., and Smith, A. G., Petroleum Engr., 19, 47 (August 1948). Absorption and fractionation. Benedict, M., Johnson, C. Α., Solomon, E., and Rubin, L. C., Trans. Am. Inst. Chem. Engrs., 41, 371 (1945). Azeotropic distillation. Berg, C., Gas, 23, No. 1, 32 (1947). Adsorption. Berg, C., and Bradley, W. E., Petroleum Engr., 18, Reference Annual, 115 (May 1947). Ad sorption. Buell, C. K., and Boatwright, R. G., Ind. Eng. Chem., 39, 695 (1947). Extractive distillation. Campbell, J. M., and Laurence, L. L., Petroleum Refiner, 31, 65 (August 1952). Dehydration. Ibid., p. 106 (October 1952). Dehydration. Ibid., p. 109 (November 1952). Dehydration. Chem. Eng., 58, 234 (September 1951). Adsorption. Ibid., p. 242 (November 1951). Extraction. Ibid., 59, 149 (October 1952). Adsorption. Chem. Inds., 61, 625 (1947). Adsorption. Ibid., 64, 911 (1949). Adsorption. Davis, W. H., Harper, J. I., and Weatherly, E. R., Oil Gas J., 51, 112 (May 19, 1952). Adsorp tion. Dunn, C. L., and Liedholm, G. E., Ibid., 51, 68 (June 9, 1952). Extractive distillation. Dunn, C. L., and Liedholm, G. E., Petroleum Engr., 24, Reference Annual, C7 (July 15, 1952). Extractive distillation. Edmister, W. C., Ibid., 19, 47 (August 1948). Absorption and fractionation. Griswold, J., and Morris, J. W., Ind. Eng. Chem., 41, 331 (1949). Extractive distillation. Griswold, J., and Van Berg, C. F., Ibid., 38, 61, 170 (1946). Extractive distillation. Guthrie, V. B., Petroleum Processing, 6, 833 (1951). Adsorption. Hachmuth, Κ. H., Chem. Eng. Progr., 48, 523, 570 (1952). Miscellaneous. Harper, J. I., Olsen, J. L., and Shuman, F. P., Jr., Chem. Eng. Progr., 48,276 (1952). Adsorption King, J. J., and Mertz, R. V., Oil Gas J., 50, 95 (March 10, 1952). Refrigeration. Kobe, Κ. Α., and Domask, W. D., Petroleum Refiner, 31, 125 (July 1952). Extractive crystal lization. Morello, V. S., and Poffenberger, N., Ind. Eng. Chem., 42,1021 (1950). Extraction. Natl. Petroleum News, 38, R283 (April 1946). Extractive distillation. Petroleum Processing, 2, 300 (1947). Adsorption. Petroleum Refiner, 31, 99 (November 1952). Absorption. Seybert, Ε. K., Petroleum Processing, 7, 1150 (1950). Adsorption. White, R. R., Natl. Petroleum News, 36, R731 (Nov. 1, 1944). Azeotropic distillation.

TOLUENE

Arnold, G. B., and Coghlan, C. Α., Ind. Eng. Chem., 42, 177 (1950). Brandt, P. L., Lee, R. J., and Wadsworth, F. T., Ibid., 39,1010 (1947). Chem. Met. Eng., 48, 120 (January 1941). Egloff, Gustav, Met. Chem. Eng., 16, 492 (1917). Egloff, Gustav and Twomey, T. J., Ibid., 15, 15 (1916). Fischer, H. G. M., and Welty, A. B., Jr., Chem. Met. Eng., 51, 92 (August 1944). Foster, A. L., Oil Gas J., 42, 130 (April 13, 1944). Hartley, F. L., Petroleum Refiner, 24, 519 (1945). Lake, G. R., Trans. Am. Inst. Chem. Engrs., 41, 327 (1945). Natl. Petroleum News, 37, R44 (June, 1943). O'Donnel, J. P., Oil Gas J., 42, 43 (December 16, 1943). Oil Gas J., 40, 26 (October 30, 1941). Rittman, W. F., J. Ind. Eng. Chem., 7, 1014 (1915). Willcox, O. W., World Petroleum, 12, 57 (November 1941). World Petroleum, 22, 33 (February 1951). Wright, C. H., U. S. Naval Inst. Proc., 46, 1561 (1920).

RECEIVED April 2, 1953. Presented before the Division of Chemical Literature and the Division of Petro leum Chemistry, Symposium on the Literature of Chemicals Derived from Petroleum, at the 123rd Meeting of the AMERICAN CHEMICAL SOCIETY LOS Angeles, Calif.


Commercial Development of Hydrocarbons From Petroleum and

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