Oxygen-Containing Hydrocarbon Derivatives From ... - ACS Publications

Oxygen-Containing Hydrocarbon Derivatives From Petroleum and Natural Gas MARTIN M. PADWE

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.ch039

Jefferson Chemical Co., Inc., Box 4128, North Austin Station, Austin, Tex.

Derivatives of petroleum and natural gas which contain oxygen are obtained primarily by oxidation, hydration, hydrolysis, and esterification, and the general literature on these processes, as well as on the Oxo, Synol, and FischerTropsch processes, is presented. The literature concerning individual classes of oxygen-containing compounds and specific, important members of each class is next described. Catalytic operations are an inextricable part of many of the processes involved; attention is therefore directed to the literature on catalysis. Pertinent class numbers of the U. S. Patent Office are discussed. The literature presented is restricted to material published after 1936, although on occasion important earlier references are given.

Those derivatives of petroleum and natural gas which contain oxygen are obtained directly or indirectly from these basic hydrocarbons primarily b y oxidation, hydration, hydrolysis, esterification, alkylation, and b y hydrogénation of carbon monoxide. These processes either are generally applicable to the synthesis of many members of a specific class of oxygenated compounds, such as the synthesis of alcohols b y hydration of olefins, or more frequently, give a mixture of oxygenated compounds of more than one class, e.g., oxidation and carbon monoxide hydrogénation. I t is for this reason that the process literature is to be emphasized rather that the literature on individual compounds. A n attempt w i l l also be made to present selected literature on some individual compounds as well as on some groups of compounds. However, before considering the latter types of literature, attention must be directed to the general basic literature.

Basic Literature The comprehensive treatment given the subject compounds b y E l l i s (26) has re stricted the literature which is to be presented to material published after 1936, although on occasion important earlier references will be given. Emphasis has been placed on those publications which contain fairly extensive bibliographies, e.g., review articles and monographs. Perhaps the most satisfactory method of quickly obtaining information on, and litera ture references to the desired oxygenated compounds is to refer to K i r k and Othmer's "Encyclopedia of Chemical Technology" (58). Although not yet complete, most of the oxygenated compounds and the processes used i n their preparation are described i n the volumes published. The importance of this work cannot be overemphasized. B y con sulting Thorpe (113) one can supplement information obtained from K i r k and Othmer. A new edition of Houben-Weyl (49) is i n the process of publication and promises to be another important source of information. Individual works of importance are Brooks (11), which appears to be the most com370

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


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plete single volume i n the field with respect to the oxygenated and other derivatives of aliphatic and naphthenic hydrocarbons; Goldstein (40); F a i t h , Keyes, and Clark (31), in which brief descriptions of commercial methods of preparation of many oxygenated compounds from hydrocarbons are given, although no literature references are cited; and finally Brooks and Dunston (12), which supplements information on old processes and deals also with subjects and processes which are new since 1937. Review publications give considerable attention to the desired products. Reports on the Progress of Applied Chemistry, is published annually b y the Society of Chemical I n dustry, London (91). Two sections of Reviews of Petroleum Technology (95), are of special interest—the section on derived chemicals and the section on petroleum literature. The latter section is concerned primarily with the nonperiodical literature, such as books and pamphlets. This first volume of Progress in Organic Chemistry contains a section, "Chemicals from Petroleum," which emphasizes the oxygenated derivatives (89). A special guide to the publications known as P B , F I A T , and B I O S reports, many of which are included i n references to the literature, is provided i n the Bibliography of Technical Reports (115). Lederman and Green (64) give a more detailed explanation of such publications. M a n y other encyclopedias, books, and review publications could be mentioned, but the above-mentioned publications are deemed essential to the location ôf the desired litera ture on the oxygenated compounds.

Process Literature The process literature is presented i n some detail i n the work b y Shreve (105), and especially b y Groggins (42). Earlier work on oxidation processes is adequately dealt with i n the AMERICAN CHEMICAL SOCIETY Monograph b y M a r e k and H a h n (69). The September 1948 issue of Industrial and Engineering Chemistry contained the first U n i t Processes review. This first review embraced developments i n unit processes reported i n the literature since approximately the start of W o r l d W a r I I . Among the the pertinent processes covered by the first review were oxidation, hydration and hydroly sis, esterification, alkylation, halogenation, and sulfonation. Thereafter, these reviews appeared annually with the exception of the hydration and hydrolysis section which ap peared biennially. The section on hydrogénation and hydrogenolysis first included the hydrogénation of carbon monoxide i n 1951. The literature surveyed b y these process reviews is very extensive and considers not only the journal literature, but the patent and P B literature as well. These reviews, i n addition to providing the most expedient method for keeping abreast of the current literature for the processes involved, serve as a fairly comprehensive literature source for the time period covered b y a l l the reviews. M u c h of the literature through 1947 on the preparation of oxygenated compounds by the hydrolysis as well as b y the dehydrochlorination of organic chlorine compounds is contained i n a work b y Huntress (51). Variations i n the conditions employed i n the hydrogénation of carbon monoxide have led to a group of processes a l l of which yield important quantities of oxygenated materials, either as by-products or as the main product, the initial carbon monoxide and hydrogen mixture (synthesis gas) being derivable from paraffin gases, especially methane. T w o of these processes, although directed primarily to the manufacture of synthetic fuels, have always given considerable amounts of by-product oxygenated materials. These are the Fischer-Tropsch process and the American hydrocarbon process (Hydrocol process). Those processes concerned directly with the production of oxygenated compounds are the methanol and higher alcohol syntheses, the Synol process, and the recent Oxyl process. A recent' paper describes a British process i n which the amount of oxygenated compounds obtained is intermediate to that obtained i n the processes mentioned above. T h e Oxo process, that is, the catalytic addition of carbon monoxide and hydrogen to olefins to give aldehydes followed b y reduction of the latter to alcohols, is almost invariably associated with carbon monoxide hydrogénation in the literature and will be similarly treated here. Publications b y Storch, Golumbic, and Anderson (110), U . S. N a v a l Technical Mission (118), Schmidt (99), M a r t i n and Weingaertner (70), Anderson (4), W e i l and Lane LITERATURE RESOURCES Advances in Chemistry; American Chemical Society: Washington, DC, 1954.


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(128), and Komarewsky, Riesz, and Estes (60) include discussions of the majority of the above-mentioned processes except the Oxyl. Recent papers by E l i o t (25), Steitz and Barnes (109), Cain, Weitkamp, and Bowman (15), Weitkamp and F r y e (124), and M o r r e l l (78) are concerned with the distribution of oxygenated compounds i n the Hydrocol products; a paper by G a l l , Gibson, and H a l l (36) discusses the British counterpart. Considerable literature, especially patent literature, deals with processes for the iso lation of oxygenated products present i n the mixture of hydrocarbons and oxygenated compounds obtained from synthetic fuel processes. A n excellent source for such litera ture, as well as for much carbon monoxide hydrogénation and Oxo process literature, is the U . S. Bureau of Mines, "Synthetic Liquid Fuel Abstracts," now discontinued (114)Although general and patent literature are included therein, probably the greatest i m portance of this work lies i n the fact that abstracts are given for German work—that is, the P B reports, the T O M (Technical O i l Mission) reels, etc., whereas Chemical Abstracts has not abstracted such material, and the Bibliography of Technical Reports abstracts are often inadequate and poorly indexed by comparison. Special references on the methanol and higher alcohol syntheses are E l l i s (27), Hirst (45), Kastens (54), and Giesen and Hanisch (38). The O x y l process is described by Roelen and Beery (96). The Synol process literature is covered i n references (4, 38, 110,118). Oxo synthesis literature is reported on i n some detail by H o l m (46), Schuster (100), and Orchin and Schroeder (83). Recent research on acetylene as the basic hydrocarbon i n the synthesis of a number of important oxygen-containing compounds has centered on the work of Walter Reppe and his associates of Germany. Prior to Reppe's work, the most important oxygen-con taining derivatives of acetylene were acetaldehyde and acetone. Three important processes have evolved from Reppe's work. Vinylation, the for mation of v i n y l derivatives by reaction of such compounds as acids, glycols, and alco hols with acetylene, produces the important v i n y l esters and v i n y l ethers. Ethinylation is defined as the reaction of acetylene with the carbon atom of a reactant without loss of the triple bond. A major application of the ethinylation reaction is to aldehydes and ketones to give alkynols and alkyndiols—e.g., the reaction of acetylene with for maldehyde to give propargyl alcohol and butyn-2-diol-l,4. Carboxylation (also referred to as carbonylation), the reaction of acetylene with carbon monoxide i n the presence of metal carbonyls, has been applied to the production of acrylic acid, acrylates, and hydroquinone. The polymerization of acetylene to cyclooctatraene and oxygenated derivatives ob tainable from the latter is also described (17, 44, 84, 92, 93, 94). The general acetylene literature up to 1938 is reported on by Nieuwland and Vogt (81). I n addition to a translation of Reppe's own work (92), two excellent reviews i n the English language of Reppe chemistry are Owens and Johnson (84) and Copenhaver and Bigelow (17). Several other important works on Reppe chemistry are Reppe (93, 94), Hecht and Krôper (44), and Piganiol (86). The Diels-Alder reaction (diene synthesis) is the addition of compounds containing double or triple bonds (dienophiles) to the 1,4 positions of conjugated dienes with the formation of six-membered hydroaromatic rings. Hydrocarbons most often used i n the reaction are 1,3-butadiene, cyclopentadiene, and isoprene, and dienophiles used include maleic anhydride, acrolein, and acrylic acid. The literature on this process is thoroughly reviewed by Alder (1), Kloetzel (59), Holmes (48), and N o r t o n (82). The reaction of olefins with aldehydes to form 1,3-glycols has recently been reviewed by Arundale and Mikeska (5). Considerable literature exists on the mechanism of hydrocarbon oxidation and autoxidation. Thé more important of these works are by Waters (122), the Faraday Society (23,32), and Frank (33). Organic peroxide formation by the oxidation of hydrocarbons and the reaction of these compounds is especially emphasized by Frank (33), Criegee (18), Hawkins (43), and Kharasch (57). LITERATURE RESOURCES Advances in Chemistry; American Chemical Society: Washington, DC, 1954.


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The literature on the use of organic per acids for the oxidation of olefins, especially higher olefins, to epoxides and glycols has been surveyed b y Swern (112). Oxidation of hydrocarbons with selenium dioxide can result i n the formation of dialdehydes, ketones and diketones, and unsaturated alcohols, depending upon the hydro carbon used. Such oxidations have been summed up b y Rabjohn (90). Since so many of the processes involved are catalytic i n nature, a few of the more important publications i n the field of catalysis should be mentioned. These are Berkman, M o r r e l l , and Egloff (6), B u r k (If), Griffith (41), Schwab (101), the Faraday Society (22), and Frankenburg (84). A guide to the analysis, as well as to the ordinary physical properties of pure oxygen ated compounds is provided for i n a work b y Huntress and M u l l i k e n (52). The physical constants (ni?, b.p., and m.p.) with references to the original literature for a selected number of organic peroxides are given b y Mesrobian (71).

Literature on Individual Compounds or Groups of Compounds The following literature has been selected as a guide to information on a few individual members and groups of oxygenated compounds. These compounds have been chosen either because special literature is available or because of their importance. The German reports included have been chosen since they give detailed information not generally obtainable. F o r many of the individual members and groups of compounds, the existing literature is almost exclusively patent literature. T h e pertinent classes of the U . S. patent system will be described later. Formaldehyde. Oxidation with air or oxygen of natural gas or propane a n d butane yields not only formaldehyde b u t also acetaldehyde, propionaldehyde, acetone, methyl ethyl ketone, tetrahydrofuran, methanol, propanol, b u t y l alcohols, and formic, acetic, and propionic acids. Such literature is covered b y Walker (120, 121). Two reports'on German processes for oxidation of methane to formaldehyde are given b y Sherwood (104), and b y H o l m and Reichl (47). One of these processes indicates the almost exclusive formation of formaldehyde; i t is also indicated that the process was applied to ethane and propane with similar results. Acetaldehyde. T h e manufacture of acetaldehyde i n G e r m a n y b y h y d r a t i o n of acetylene is described b y Alexander (2) and b y Brundrit, Taylor, and E l l i s (18). Acetaldehyde preparation b y hydrolysis of lower v i n y l ethers is briefly indicated i n the latter reference as well as b y Leaper and Direnga (68). F o r complete coverage of the literature on these methods, see references (17,44,81,84, 86,92,98,94). Ethyl Alcohol and Higher Alcohols. T w o general processes exist for h y d r a t i n g olefins to alcohols. T h e first is b y absorption of olefins i n inorganic acids, p r i m a r i l y sulfuric acid, followed b y hydrolysis of the intermediate ester. The second process is the direct catalytic hydration of the olefin. The literature on these processes, especially as applied to ethanol and 2-propanol manufacture, is well covered i n the general works listed above, and especially b y Brooks (11). German work on the catalytic hydration of ole fins is described by Kammermeyer and Carpenter (53). The preparation of amyl alcohols via chlorination of pentanes and hydrolysis of the halides is described b y K e n y o n (56). Epoxides and Glycols. T h e literature on the important aliphatic epoxides a n d glycols, especially ethylene and propylene oxides and ethylene and propylene glycols, is given b y Curme and Johnston (20). Detailed descriptions of German processes for the manufacture of ethylene oxide b y direct oxidation of ethylene and v i a chlorohydrination of ethylene are given b y Goepp (39) and b y Vaughan and Goepp (119). Brief descrip tions of the direct and chlorohydrination processes as well as of the manufacture of ethyl ene glycol from ethylene oxide b y hydration and from ethylene dichloride b y hydrolysis are given b y M o r l e y (77). The hydration of ethylene oxide to ethylene glycol and higher glycols is also described b y Brandner and Goepp (9). Allyl Alcohol and Glycerol. These two products are treated together since both involve the chlorination of propylene to a l l y l chloride. T h e Shell a l l y l alcohol process is described b y Fairbairn, Cheney, and Cherniavsky (80). This same process and the glycerol process are described b y Williams (125). The German counterpart of these LITERATURE RESOURCES Advances in Chemistry; American Chemical Society: Washington, DC, 1954.


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processes is briefly described b y Sheely (102). A l l y l alcohol preparation b y isomerization of propylene oxide is given b y Lunsted (68). The Shell Chemical C o . has published a booklet (103), which describes the properties and reactions of this alcohol. Further literature on synthetic glycerol is to be found i n the new AMERICAN CHEMICAL SOCIETY Monograph by M i n e r and Dalton (73). Acetone, Methyl Ethyl Ketone, Acetic Acid, and Propionic Acid. Oxidation of the lower hydrocarbons i n the gas phase catalyzed b y hydrogen bromide gives carboxylic acids, ketones, and hydroperoxides, depending on the hydrocarbon used. Ethane gives acetic acid; propane gives acetone plus a significant amount of acetic and propionic acids; η-butane yields methyl ethyl ketone and acetic acid. Oxidation of branched-chain hydrocarbons such as isobutane and isopentane gives peroxides and hydro peroxides as major products and alcohols as coproducts. This literature is reviewed by Rust and Vaughan (97). F o r information on acetone from 2-propanol, see the general introductory literature. F o r literature on acetone v i a cumene oxidation, see below under phenol from cumene. Carboxylic Acids and Esters. T h e literature on G e r m a n methods for the preparation of unsaturated acids a n d their esters v i a acetylene, carbon monoxide, and water or alcohol, as well as the application of this reaction to olefins, carbon monoxide, and water or alcohol to give saturated acids and esters, is to be found i n references (17, 44, 84, 92, 93, 94). Other references on these methods are Blair-McGuffie (7) and N a t t a (80). The preparation, properties, and reactions, especially polymerization, of products from the acetylene-carbon monoxide reaction, such as acrylic acid and its esters, are given by Blout and M a r k (8) and by Schildknecht (98). Similarly treated therein are the v i n y l esters from acetylene and carboxylic acids, and other vinylation products such as v i n y l ethers. The esterification of organic acids with olefins is reviewed b y M o r i n and Bearse(7£). Higher Fatty Acids. Oxidation of higher paraffins can give mixtures of acids, alcohols, and carbonyl compounds, although fatty acids may be obtained as the principal product. Publications b y W i t t k a (126), Stossel (111), Allen (3), Lanning (62), Zabel (128), and G a l l (35) are of importance i n this field. Adipic Acid* T h e G e r m a n process for the preparation of this compound is described b y Smith (108). Maleic Anhydride. T h e preparation of maleic anhydride from C hydrocarbons is given by Bretton (10). The preparation of maleic anhydride from benzene is described in F a i t h , Keyes, and Clark (81). Maleic anhydride is an important by-product i n the phthalic anhydride process. Phthalic Anhydride. T h e preparation of phthalic anhydride from xylene is described by Parks and A l l a r d (85) and Levine (65). Phthalic anhydride from naphtha lene is discussed by Downs (24), Shreve and Wilborn (106), Ellis (28), Hunter (50), Y o u n g (127), and Nash (79). Phenol. T h e manufacture of phenol b y the oxidation of benzene is described by Denton (21) and by Simons and M c A r t h u r (107). The literature on phenol by the oxidation of cumene is partly covered i n the reports of Frank (33), Hawkins (43), and Kharasch (57), mentioned earlier. A brief description and flow sheet of the process is given in Chemical Engineering (16). The patents i n this field are mainly held b y The Distillers Co., L t d . , Hercules Powder Co., and Allied Chemical and D y e Corp. I n this phenol process large amounts of acetone are obtained as a coproduct. I t should also be noted that the process may be directed to the production of cumene hydroperoxide and a,adimethylbenzyl alcohol. Krieble (61) and K e n y o n and Boehmer (55) describe the prepa ration of phenol by the chlorination and sulfonation processes. Alkyl Phenols. T h e literature on the a l k y l a t i o n of phenols w i t h olefinic h y d r o carbons has been reviewed by Price (88). Aromatic Aldehydes. T h e preparation of aromatic aldehydes from benzene or monoalkyl and polyalkyl aromatic compounds b y means of carbon monoxide and hydro gen chloride has been reviewed by Crounse (19). Acetophenone. T h e oxidation of ethylbenzene to acetophenone is described by Emerson (29) and b y Pinkernelle and Kroning (87). 4



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Aromatic Acids by Oxidation of Side Chains. G e r m a n work on this subject is briefly reported on b y M i t t a g (74, 75) and b y Michel and K r e y (72). Cresylic Acids. These compounds are discussed b y Gallo (37). Naphthenic Acids. Important literature on these acids includes L i t t m a n n a n d K l o t z (66) and Lochte (67). D r . Loch te is preparing a book entitled "Petroleum Acids and Bases" ; publication is expected in late 1953 or early 1954.


U. S. Patent Literature The U . S. Patent Office provides several guides for obtaining those patents of interest. These are the " M a n u a l of Classification of Patents" (117), the index to said manual, plus a series of classification bulletins which define the classes and subclasses listed i n the manual. Once having determined the subclasses of interest, one m a y obtain from the Patent Office, at a charge of about 20 cents a page, separate numerical lists of both the original references and cross references i n each subclass. Furthermore, the Patent Office will supply these lists of subclasses and cross-reference lists upon receiving a request which fully describes the subject matter of interest. The subclasses of Class 260, " T h e C h e m istry of Carbon Compounds," are the subclasses of main interest, and these have been recently revised. The definitions for Class 260 are i n Classification Bulletin N o . 200 (116). It may be noted at this time that a revised copy of this bulletin, as well as a new index to the "Classification M a n u a l , " is scheduled for publication i n the near future. Specific important subclasses of Class 260 are listed. Heterocyclic compounds 341 Poly carboxylic acid anhydrides 342 Polycarboxylic acid anhydrides by oxidation of aromatic compounds, e.g.—phthalic anhydride from naphthalene or o-xylene and also maleic anhydride from benzene 342.6 Anhydrides of acyclic polycarboxylic acids 348 Epoxy compounds, general 348.5 Epoxy compounds by oxidation of olefins—e.g., ethylene oxide by oxidation of ethylene 348.6 Epoxy compounds by dehalogenation (actually dehydrohalogenation)—e.g., ethylene oxide from ethylene chlorohydrin Carbocyclic or acyclic compounds 449 Hydrogénation of carbon oxides to give mixtures of hydrocarbons, alcohols, esters, and acids 449.5 Methanol synthesis from CO and H . Higher alcohol synthesis from CO and H are also included i n this subclass 449.6 Hydrogénation of carbon oxides with iron, cobalt, or nickel catalysts (FischerTropsch process). Hydrocarbons are the main products 450 Recovery and separation of oxygenated products obtained from CO and H 451 Partial oxidation of nonaromatic hydrocarbon mixtures, e.g., petroleum, paraffins, and natural gas, to produce a mixture of products, such as esters, acids, aldehydes, ketones, and alcohols. This also includes higher fatty acids from petroleum and patents on formaldehyde production 452 Subclass 451, i n which the recovery or purification of the products is especially emphasized 460 Sulfuric acid esters from olefins by direct sulfation 468 Carboxylic acid esters 478 Acyclic carboxylic acid esters 497 Acyclic carboxylic acid esters from olefins; this includes esters from olefins + alcohol + CO and from olefins + acids 498 Acyclic carboxylic acid esters from acetylene; this includes esters from acetylene + acid 514 Carboxylic acids; this includes naphthenic acids 515 Aromatic carboxylic acids 524 Aromatic side chain alkyl group oxidation—e.g., toluene oxidation to benzoic acid and p-xylene oxidation to terephthalic acid 526 Acyclic carboxylic acids, general 530 Acyclic carboxylic acids by oxidation of aldehydes 533 Acyclic carboxylic acids from single or mixed hydrocarbons of known constitution; this includes reaction of acetylene with CO and water, reaction of olefin with C O and water, and also dibasic acids from cycloalkanes 537 Acyclic polycarboxylic acids, e.g., from cycloalkanols and/or cycloalkanones 540 Saturated lower fatty acids, general 2

2

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376

542 546 586 590 592 593 596


597 598 599 601 604 605 610 611 614 617 618 619 621 624 626 628 629 631 632 634 635 636 637 638 639 640 641 643 Processes 686 687 690 692 693 694

Formic acid from CO and water Carboxylic acid anhydrides, general Carbocyclic or acyclic ketones—e.g., by oxidation of cycloalkanes Aromatic ketones Acetophenone Acyclic ketones Dehydrogenation or dehydration of-alcohol to form ketones, e.g., acetone from isopropyl alcohol Acyclic ketones from hydrocarbons; this includes ketones prepared by the Oxo process Carbocyclic or acyclic aldehydes Aromatic aldehydes Acyclic aldehydes Acyclic aldehydes from hydrocarbons—processes where definite hydrocarbons are employed as starting material; this includes Oxo process, formaldehyde processes and acrolein from propylene Acyclic aldehydes from acetylene—e.g., acetaldehyde from acetylene Organic carbocyclic or acyclic peroxides—e.g., cumene hydroperoxide Carbocyclic or acyclic ethers Acyclic ethers Carbocylic or acyclic hydroxyl compounds, general Aromatic hydroxy compounds Phenols Phenol by benzene oxidation C-polycarbon alkyl or alkylene phenols C-isopropyl or isopropylene phenols; both 624 and 626 include patents on alkylation of phenols Phenols from aryl sulfonates Phenols by hydrolysis of aryl halides Cyclohexanols Acyclic hydroxy compounds (see also 638) ; this includes Oxo process patents which go beyond the aldehyde stage by reduction Acyclic chlorohydrins from olefins Polyhydric acyclic compounds; this includes oxidation of cycloalkanes, cycloalkanols and cycloalkanones to such products Polyhydric acyclic compounds by hydrolysis of alkyl polyhalides or halohydrins— e.g., the glycerol process and ethylene glycol from ethylene dichloride Purification of acyclic polyhydric compounds Acyclic hydroxyl compounds directly from carbonyl containing compounds; this seems to overlap Subclass 632 as far as the Oxo process alcohols are concerned Acyclic hydroxy compounds by hydrolysis of alkyl esters of polybasic inorganic acids—e.g., alcohols via olefins + inorganic acid + hydrolysis Acyclic hydroxy compounds by hydrolysis of alkyl halides Acyclic hydroxy compounds by hydration of olefins (direct hydration) Purification or recovery of acyclic hydroxy compounds Sulfonation or sulfation Oxidation Hydrogénation Etherification by alkylation of an alcoholic or phenolic hydroxyl group Fusion with alkalies to convert sulfonic group to O H group Halogenation

Close examination of the above list will reveal that both the original subclass and the cross references in each of several subclasses must be consulted i n order to find a l l the art on a given subject. I t should also be noted that frequent changes i n the classification scheme are made.

General Sources T o obtain references to the foreign patent literature one must search through either Chemical Abstracts, CMmisches Zentralblatt, or British Abstracts. T o obtain literature on other pertinent German processes, the Bibliography of Technical Reports must be searched. It is hoped that the literature which has been presented w i l l provide a background for such searches and also indicate some of the more numerous headings which w i l l have to be used to obtain a more complete picture of the literature of the oxygen-containing hydrocarbon derivatives obtainable from petroleum and natural gas. LITERATURE RESOURCES Advances in Chemistry; American Chemical Society: Washington, DC, 1954.


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Literature Cited (1) (2) (3)

(4)


(5) (6) (7)

(8) (9)

(10) (11) (12)

(13)

(14)

(15) (16) (17) (18) (19) (20) (21) (22) (23) (24) (25) (26) (27) (28) (29) (30) (31) (32) (33) (34) (35)

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380 (101) (102) (103) (104) (105) (106) (107)


(108) (109) (110) (111) (112) (113) (114) (115) (116) (117) (118)

(119)

(120) (121) (122) (123) (124)

(125) (126) (127) (128)

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R E C E I V E D March 3, 1953. Presented before the Division of Chemical Literature and the Division of Petroleum Chemistry, Symposium on the Literature of Chemicals Derived from Petroleum, at the 123rd Meeting of the A M E R I C A N C H E M I C A L S O C I E T Y , Los Angeles, Calif.


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