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VLADIMIR NIKOLAEVICH IPATIEFF November 2Z, 1867-November 29, 1952 BY LOUIS SCHMERLING FORTUNATELY FOR BOTH the scientific and the industrial worlds, Vladimir Nikolaevich Ipatieff, who was born in Moscow on November 21, 1867, did not maintain his original intent to have a military career. When he was eleven years old, he was enrolled at the Third Moscow Military Gymnasium after three years in a classical gymnasium. He had no difficulty completing the courses, but his grades were poor until he was promoted to the sixth class at the age of fourteen. His favorite subject was mathematics, which he studied beyond the class requirements. His report card showed steady improvement, particularly in science courses. However, on being graduated at the age of sixteen, his application to the Mikhail Artillery School in St. Petersburg was rejected on the basis of his grades. He entered the Alexander Military School in Moscow, where he received an intense military education. He ranked near the top of his class and, rather than accept rank as sergeant, he decided to transfer in September 1886 to the Mikhail Artillery School, to which he was now admitted, the 450 ruble tuition being waived because he had the highest grades in his class in mechanics, artillery, and chemistry. He became an officer (lieu- ~ The author gratefully acknowledges his particular indebtedness to Dr. Vladimir Haensel for suggesting that he write this biography and for his helpful advice and comments throughout. 83

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84 BIOGRAPHICAL MEMOIRS tenant) ~ on August 7, 1887, a day that he considered mem- orable because of the solar eclipse that occurred and the con- current scientific flight in a balloon made by a famous chemist, Dimitrii I. Mendeleev. Using part calf the money he received from the government and from his father for officer's equip- ment, he furnished a small chemistry laboratory in his home where he could study qualitative analysis (quantitative analysis being beyond his means because a balance was too expensive). After a four weeks' vacation, Lt. Ipatieff chose to join the Second Reserve Artillery Brigade and became a teacher of arithmetic and artillery at a battery school in Serpukhov (about 60 miles from Moscow). Since his classes were in the morning, he could devote his afternoons to studying chemistry, largely from two Russian language books: Mendeleev's The Funda- mentals of Chemistry (3d edition, 1884), and Menshutkin's Analytical Chemistry, books that he claimed were his real teachers. After teaching for two years, he passed competitive entrance examinations and, in September 1889 was admitted to the Mikhail Artillery Academy in St. Petersburg, which had been founded to give technical training to officers who were to serve as engineers in government munitions plants, as inspectors of materials furnished by private concerns, or as members of the Artillery Committee of the Chief Artillery Administration. Unfortunately (from Ipatieff's viewpoint), the supposedly well-equipped chemical laboratory at the Academy was less useful than it could have been: it had equipment for classes in qualitative and quantitative analysis, but not in organic chemistry. ~ Graduates of an institution such as the Mikhail Artillery School were given commissions and assigned to (or, if their grades were high, permitted to choose) active duty. Then, after serving in the army for a few years and after passing stiff competitive examinations, they could enter academies (such as the Mikhail Artillery Academy) for specialized training that led to high positions in the army or in military educational institutions.

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VLADIMIR NIKOLAEVICH IPATIEFF 85 Ipatieff moved his home laboratory to his apartment in order to carry out experiments while studying for examinations. He found it necessary to get approval from the Governor of St. Petersburg because the police were suspicious of home lab- oratories, which might be used to prepare explosives. He received industrial experience in his junior year when he spent June and July working at plants and factories, par- ticularly in steel mills. He spent much time learning analytical methods of metallurgy. He commuted to the plants in order to be able to use his own laboratory in the evening. He was cr~c~zea oy nits supervisor (and his final grade was low) for spending more time in his laboratory than at the plants, but he had no regrets because he felt he learned much there that helped him all his life. Fellow students found Ipatieff's notes quite useful and persuaded him to prepare manuals of qualitative and quantita- tive analysis; these were subsequently published in 1891 by the Academy. ~ 1 1 1 ~ Much of Ipatieff's time at the Academy was spent studying the properties and analysis Off steel working with the In ~ .. . _J ~~ Van ~ vv ~~ ~5 VV ALll Ally l Ally Ill Russian metallurgist, Professor Dimitrii K. Chernov. This resulted in 1892 in his first publication, "The Chemical Investi- gation of the Structure of Steel." Largely due to this work and to his manuals, Ipatie~ was retained by the Academy as an instructor (with the military rank of captain) after he was grad- uated on May 30, 1892, third highest in his class. He was granted a short leave of absence, which he used to travel to Moscow to marry Varvara Ermakova, whom he had known for ten years. His first teaching duties involved a junior class course in qualitative analysis. He decided to devote one hour a week to lectures on the laws of chemistry because he realized the de- ficiency of his chemical education at the Academy. He pub- lished a set of notes entitled, Principal Laws of Chemistry. Academy regulations required that in order to continue

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86 BIOGRAPHICAL MEMOIRS teaching all instructors present an approved dissertation three years after their appointment as instructors. Ipatieff asked the advice of Professor A. E. Favorsky of St. Petersburg University, who was lecturing on organic chemistry at the Academy. Favor- sky suggested that he study organic chemistry and carry out research in that field. "For," said Favorsky, "it is only in organic chemistry that you will learn to think chemically and to experi- ment rationally." Ipatieff therefore took a course in organic chemistry from N. A. Menshutkin at the University of St. Peters- burg, but found that although he profited from the lectures, he did not find them interesting because Menshutkin presented them chiefly from an analytical and physical chemistry view- point. Ipatieff devoted himself to studying A. M. Butlerov's textbook of organic chemistry. His first practical work in organic chemistry was carried out in Favorsky's laboratory, where he started to study the isomeriza- tion of allene hydrocarbons to disubstituted acetylenes, as pro- posed in Favorsky's master's thesis. He spent much time learn- ing how to prepare dimethylpropylcarbinol by the reaction of dimethylzinc with the butyryl chloride. By the end of the spring of 1893, he had prepared two pounds of the tertiary alcohol. He studied the action of bromine on tertiary alcohols (usually using the commercially available tert-butyl alcohol) to obtain a dibromide from which an allene could be prepared. This and subsequent work formed his dissertation, "The Action of Bromine on Tertiary Alcohols and of Hydrogen Bromide Upon Acetylene and Allene Hydrocarbons in Acetic Acid Solu- tions," which was presented and accepted in 1895. Ipatied became an assistant professor and taught both inorganic and organic chemistry. He was awarded the first of his many (about twenty-five) awards in 1895the Order of St. Stanislaus, third class. In 1896, the Academy, which was entitled to send one of its instructors abroad each year, decided to send Ipatieff to study .

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VLADIMIR NIKOLAEVICH {PATIEFF 87 chemistry and the new explosives in use in other countries. Favorsky suggested that he go to Munich to work in the labora- tory of Adolf van Bacyer, to whom Favorsky immediately wrote, enclosing a copy of Ipatieff's dissertation, published in German. This letter and one from a Russian classmate of Bacyer resulted in Bacyer's accepting Ipatieff as an assistant for joint work. Baeyer suggested that Ipatieff study the structure of the terpene derivative, carone. Based largely on the determination of the structure of the caronic acids formed by permanganate oxida- tion of carone, Ipatieff was able to prove the structure of carone in about four or five months. Baeyer was so pleased by his assistant's work that he told Ipatieff to write up the investigation so they might publish it jointly rather than, as was usually the case, publish in Baeyer's name only with an expression of grati- tude to the young co-worker at the end of the paper. The remainder of Ipatieff's research in Munich was inde- pendent work, to which he turned at Baeyer's suggestion. He chose to finish work on a problem he had started at the Academy, the action of hydrogen bromide on allenes and other dienes. He found that addition of hydrogen bromide to 1,1-dimethyl- allene yielded the same dibromide as did its addition to isoprene. Dehydrobromination of the dibromide prepared from dimethyl- allene yielded isoprene, and Ipatieff was thus the first chemist to synthesize and then prove the structure of isoprene. While in Baeyer's laboratory, Ipatieff met Dr. Richard Willstaetter of Germany, who later became noted for organic research, particularly the synthesis of chlorophyll, and Dr. Moses Gomberg of the United States, who would later discover stable free radicals. They remained lifelong friends. Before returning to St. Petersbur~ in 1897 Inntieff vi~it`,r <~~ ~ ~ -r ~ chemists in Germany and France, including Rudolf Fittig, Pierre Berthelot, and Charles Friedel. He inspected military institutions and discussed ballistics. While in France, he spent four months with Paul Nlielle, discoverer of smokeless gun-

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88 BIOGRAPHICAL MEMOIRS powder, studying the combustion of ballastite at various charg- ing densities to check the accuracy of the parallel layer com- bustion theory. Ipatieff carried out his usual large quantity of research experiments when he returned to the Artillery Academy. He was appointed a member of the Explosives Commission and of the Fifth Section of the Artillery Committee, which dealt with gunpowder and chemical questions. He also accepted appoint- ment as assistant professor at the Institute of Civil Engineers to teach chemistry and to supervise student experiments. Despite all these interests, he found time to attend the Second Inter- national Congress on Pure and Applied Chemistry in Vienna in the spring of 1898 and to write his dissertation on allene hydrocarbons, on the action of nitrosyl chloride and nitrogen oxide on unsaturated compounds, and on the synthesis of iso- prene. Acceptance of his dissertation at a public examination resulted in his being given the title Professor of Chemistry and Explosives. As the first chemistry teacher to hold the rank of professor at the Artillery Academy, Ipatieff redesigned and refurnished the laboratories and wrote textbooks on inorganic (seven revised editions) and organic chemistry (six revised editions). In 1900 he began to prepare a large quantity of butadiene by the only method then knownthe passage of isopentyl al- cohol vapors through a heated tube at about 600C. However, he obtained isovaleraldehyde and hydrogen instead of the ex- pected butadiene, methane, and water. He found that when he used a glass or quartz tube instead of the iron tube he had used in his earlier experiments, there was no reaction unless the temperature was raised to 700 C. Similar experiments showed that passage of other primary alcohols through the hot iron tube (but not the quartz tube) produced aldehyde and hydrogen, secondary alcohols yielded ketones and hydrogen, and tertiary alcohols underwent no reaction other than dehy-

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VLADIMIR NIKOLAEVICH IPATIEFF 89 dration. Ipatieff concluded that the iron wall of the tube caused the dehydrogenation of the alcohols without undergoing any change; in other words, there occurred a new phenomenon, which Russian chemists called a contact reaction and other European chemists called a catalytic reaction. The significance of Ipatieff's work was that he showed that such reactions could occur at high temperatures; it had been assumed that under such conditions there would be complete breakdown of the alcohol and no clean reaction would occur. It had been be- lieved that the conversion of an organic compound could not be directed at temperatures above 250C, certainly not at 500- 600C. IpatieR also showed for the first time the influence of reaction vessel walls on a reaction. He became so interested in this subject that he dropped all other investigations and spent all his research time on catalysis, a field in which he made many outstanding contributions during the next fifty-one years. He showed that easily reducible oxides and the metals (for example, zinc, cupric oxide, and copper) catalyzed the dehy- drogenation of alcohols to ketones and aldehydes. On the other hand, when he used a graphite tube to investigate the effect of carbon, he was astonished to find that a different type of reaction occurred and at a lower temperature; ethyl alcohol was dehydrated to ethylene. Further investigation proved that the effect was due not to the graphite but to the clay binder used in the tube. Finally, Ipatieff showed that the difficult-to- reduce alumina in the clay was the dehydration catalyst. In 1902 he was appointed Professor Ordinary at the Artillery Academy, a considerable promotion both in salary and rank. He also became a lecturer at the University of St. Petersburg, with which he was connected until 1916, taking over a course in general chemistry in 1906. Because the chief function of the Academy was to train officers, Ipatieff found it difficult to find assistants for research. Nevertheless, he was able to discover new catalytic reactions,

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JO BIOGRAPHICAL MEMOIRS such as (in 1903) the isomerization of olefins over alumina or zinc chloride and the conversion of ethyl alcohol to butadiene in the presence of powdered aluminum at 600C. Moreover, in order to study the effect of high pressure on catalytic reac- tions, he designed a rotating autoclave (or "bomb") having a closure consisting of a disk gasket of heat-treated copper or other metal between two knife edges, one on the autoclave top and the other on the bottom of the cover. The usefulness and safety of this piece of apparatus was proved by the many tens of thousands of experiments that were, and are still, carried out . . In it. During the war between Russia and Japan (190~1905), Ipatieff and other officers who had been graduated from the Artillery Academy and continued to work in technical institu- tions received promotions to the same ranks as men who had been graduated at the same time but had gone into active service. He became a colonel. Despite the war and the political unrest that followed, Ipatieff's scientific research continued with little interruption. He investigated the effect of high pressures on such chemical processes as the addition of hydrogen to unsaturated hydrocar- bons (olefins and aromatics>, the destructive hydrogenation of organic compounds, and the polymerization of ethylene. These researches were destined to play an important role in the chem- ical industry. Ipatieff showed that the liquid phase hydrogena- tion of organic compounds is a more rapid reaction and in many cases proceeds farther than the vapor phase hydrogenation at atmospheric pressure, a reaction then being studied in France by Paul Sabatier and J. B. Senderens. In 1906 the Russian Academy of Sciences awarded Ipatieff the 4000-ruble Ivanov Prize in recognition of his scientific work. This increased his prestige and resulted in his being permitted to submit a dissertation, "Catalytic Reactions Under High Pres- sures and Temperatures," to the University of St. Petersburg for

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VLADIMIR NIKOLAEVICH IPATIEFF 91 the Doctor of Chemistry degree. Such permission was necessary because he had never been graduated from a classical gym- nasium. A university regulation of 1884 made it possible to admit to public examination for higher degrees scientists whose achievements had made them famous; permission from the Minister of Education was necessary. Ipatieff received the per- mission, presented his dissertation, was examined publicly in February 1908, and was named a Doctor of Chemistry. In 1909 Ipatieff discovered an important phenomenon, the "promoter effect" of additives on catalysts. He noticed that the high-pressure hydrogenation of olefins in the presence of copper oxide was slow when carried out in a bronze-lined autoclave, but rapid and complete when an iron autoclave was employed. He concluded that the iron wall of the autoclave was a promoter for the hydrogenation. Similarly, he found that complete hy- drogenation occurred in the bronze-lined autoclave, if the added copper oxide was mixed with iron filings. Incorporation of promoters in catalysts is, of course, now widely used. Having taught for twenty-five years, as an "ordinary pro- fessor" for ten, Ipatieff in 1912 was named emeritus professor, a position that permitted him to continue teaching for ten more years at the Academy and to draw a yearly pension of 1500 rubles. His scientific life did not interfere with his military life. In 1910 he was promoted to the rank of major general; in 1914, lieutenant general. However, military factors did interrupt his research. During World War I, he was chairman of the Com- mission for the Preparation of Explosives, which by the end of the war controlled almost the entire chemical industry. In 1916 he was named chairman of the Chemical Committee of the Chief Artillery Administration, formed largely because of the Ger- man's use of poison gas. The Committee had five branches: poison gases, gas masks, explosives, incendiaries and flame throwers, and acids. It was concerned with developing the

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92 BIOGRAPHICAL MEMOIRS production of these items as well as deciding the best types to manufacture. ~ The personnel of the Chemical Committee remained largely unchanged, even after the Russian Revolution in 1917, because most of its members were nonpartisan and worked only for the good of the country while sincerely regretting the mistakes of the old regime. The Chemical Committee was disbanded when it had relatively little to do after the war was almost over. The Bolshevik leaders asked Ipatieff to help convert the chemical industry from a wartime to a peacetime basis. He was appointed chairman of both the Chemical Committee of the Chief Artil- lery Administration and the Technical Section of the War Council, positions from which he was relieved in June 1918 when he pointed out that he would be more useful if his scientific ability were used. He served as chairman of the Chemical Administration of the Supreme Council of National Economy (S.C.N.E.) during 1921-1926. . He found life in St. Petersburg (now renamed Petrograd) quite unpleasant in 1919-1920. Malnutrition and fuel short- age led to epidemics; typhoid fever raged through the city. Food was rationed. Work in the laboratory ceased in 1918 because water pipes froze and there was no gas supply or heating fuel. About all he did was attend meetings of the Academy of Sciences (to which he had been elected as one of the three chemist members in January 1916) twice each month and give a weekly two-hour lecture at the Artillery Academy to about seven students, who wore overcoats in the unheated classroom. Ipatieff and his family survived the Revolution largely be- cause some of the leaders realized that the country had to make good use of a man with his scientific ability and because he leas friendly with all people, whether revolutionists or peasants. * The work and political affairs of the Commission and the Committee are discussed in a most interesting and detailed manner in Ipatieff's memoirs, The Life of a Chemist, pp. 19~236.

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VLADIMIR NIKOLAEVICH IPATIEFF 131 With H. Pines and E. F. Jenkins. Studies in the terpene series. XVIII. Isomerization accompanying the dehydrogenation of 1,1,3-trimethylcyclohexene and of 1,1,3-trimethyl-x-cyclohexene. J. Am. Chem. Soc., 75:6226. 1954 With H. Pines and H. G. Rodenberg. Dehydroxymethylation of primary alcohols. l. Am. Chem. Soc., 76:771. With H. Pines and A. Rudin. Studies in the terpene series. XIX. Hydroisomerization and hydrogenolysis of cyclohexane, methyl- cyclohexene, and p-menthene in the presence of hydrogenation catalysts. i. Am. Chem. Soc., 76:2640. With H. Pines and N. E. Hoffman. Studies in the terpene series. XX. The thermal isomerization of pinane at atmospheric pres- sures. I. Am. Ghem. Soc., 76:4412. 1955 With H. Pines and B. Kvetinskas. Oxidative condensation of p- cymene, isopropylbenzene, and chloroisopropylbenzene. J. Am. Chem. Soc., 77:343. With H. Pines and J. A. Vesely. Migration of double bonds in olefinic and diolefinic hydrocarbons catalyzed by sodium. Dehy- drogenation of d-limonene to p-cymene. l. Am. Chem. Soc., 77:347. With H. Pines and l. A. Vesely. Sodium catalyzed reactions. II. Side-chain ethylation of alkyl hydrocarbons catalyzed by sodium. I. Am. Chem. Soc., 77: 5~4. 1959 My Life in the United States. Evanston, Illinois: Northwestern Univ. Press. A large number of articles in the Soviet Encyclopedia and other encyclopedias and chapters in books.

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132 BIOGRAPHICAL MEMOIRS UNITED STATES PATENTS 1933 1,895,329 With Carl Freitag. Process of Producing Phosphoric Acid and Hydrogen. 1934 1,960,631 Treatment of Hydrocarbon Gases. 1935 1,993,512 Treatment of Hydrocarbons. 1,993,513 Treatment of Hydrocarbons. 1,994,249 With Aristid V. Grosse. Synthesis of Hydrocarbons. 2,001,906 Treatment of Hydrocarbon Oils. 2,001,907 Treatment of Motor Fuel. 2,001,908 Treatment of Hydrocarbons. 2,001,909 Treatment of Hydrocarbons. 2,001,910 Treatment of Hydrocarbon Oils. 2,005,861 Manufacture of Hydrocarbons. 2,006,695 Treatment of Hydrocarbon Oil. 2,018,065 Catalysts. 2,018,066 Treatment of Hydrocarbon Oils. 2,020,649 Treatment of Hydrocarbons. 1936 2,035,889 Purification of Gases. 2,037,789 Treatment of Hydrocarbon Oils. 2,037,790 Treatment of Hydrocarbon Oils. 2,037,791 Treatment of Hydrocarbon Oils. 2,037,792 Treatment of Hydrocarbon Oils. 2,039,798 Treatment of Hydrocarbon Oils. 2,039,799 Treatment of Hydrocarbons. 2,046,900 Manufacture of Alkyl Phenols. 2,051,859 With Vasili Komarewsky. Polymerization of Olefins. 2,057,432 With Aristid V. Grosse. Treatment of Hydrocarbon Oils. 2,057,433 Treatment of Hydrocarbon Oils. 2,058,881 Treatment of Inhibitors. 2,061,871 Manufacture of Hydrocarbons. 2,062,312 Manufacture of Alkyl Phosphates. 2,063,933 Conversion of Hydrocarbon Oil.

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VLADIMIR NIKOLAEVICH IPATIEFF 133 1937 2,067,764 Treatment of Hydrocarbons. 2,081,357 Method of Improving Gasoline. 2,088,598 With Aristid V. Grosse. Manufacture of Alkylated Cyclic Hydrocarbons. 2,098,045 With Vasili Komarewsky. Treatment of Hydrocarbons. 2,098,046 With Vasili Komarewsky. Treatment of Hydrocarbons. 2,099,738 Alkylation of Trihydric Phenols. 2,101,857 With Raymond E. Schaad. Manufacture of Motor Fuels. 2,102,073 With Raymond E. Schaad. Treatment of Hydrocarbons. 2,102,074 With Raymond E. Schaad. Treatment of Hydrocarbons. 1938 2,104,424 With Aristid V. Grosse. Manufacture of Aromatic De- . . rlvatlves. 2,107,794 With Vasili Komarewsky. Manufacture of Alcohols. 2,112,846 With Herman Pines. Treatment of Hydrocarbons. 2,112,847 With Herman Pines. Treatment of Hydrocarbons. 2,113,654 With Ben B. Corson. Treatment of Catalysts. 2,116,151 With Ben B. Corson. Manufacture of Motor Fuels. 2,120,702 With Raymond E. Schaad. Manufacture of Catalysts. 2,131,806 With Vasili Komarewsky. Treatment of Hydrocarbons. 1939 2,145,657 With Vasili Komarewsky. Process for the Hydrogenation of Hydrocarbon Oils. 2,147,256 With Herman Pines. Process for Alkylating Phenols. 2,157,208 With Raymond E. Schaad. Polymerization and Catalyst Therefor. 2,169,494 With Herman Pines. Treatment of Butane. 2,170,306 With Herman Pines. Treatment of Hydrocarbons. 2,174,883 With Herman Pines. Treatment of Hydrocarbons. 2,179,092 Manufacture of Ethers. 2,181,942 With Herman Pines. Polymerization of Olefins. 1940 2,187,034 With Herman Pines. Treatment of Hydrocarbons. 2,197,872 With George S. Monroe. Treatment of Hydrocarbons.

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134 BIOGRAPHICAL MEMOIRS 2,199,564 With Herman Pines. Hydrocarbon Reactions. 2,202,104 With Raymond E. Schaad. Manufacture of Motor Fuels. 2,211,207 With Louis Schmerling. Treatment of Catalysts. 2,211,208 With Ben B. Corson. Manufacture of Catalysts. 2,214,463 With Raymond E. Schaad. Treatment of Hydrocarbons. 2,217,019 With Aristid V. Grosse. Treatment of Hydrocarbons. 2,225,782 With Ben B. Corson. Reaction of Metal Catalysts. 1941 2,236,099 With Herman Pines. Treatment of Paraffin Hydrocar- bons. 2,253,034 With Raymond E. Schaad. Manufacture of Ketones and Aldehydes. 2,267,735 With Ben B. Corson. Manufacture of Catalysts. 2,267,736 With Ben B. Corson. Treatment of Catalysts. 2,267,737 With Vladimir Haensel. Treatment of Hydrocarbons. 1942 2,270,302 With Raymond E. Schaad. Manufacture of Hydrocar loons. 2,270,303 Hydrogenation of Hydrocarbons. 2,271,299 With Herman Pines. Manufacture of Catalysts. 2,273,041 With Herman Pines. Treatment of Hydrocarbons. 2,273,042 With Herman Pines. Treatment of Hydrocarbons. 2,273,043 With Herman Pines. Treatment of Hydrocarbons. 2,273,320 With Aristid V. Grosse. Hydrocarbon Reactions. 2,275,181 With Ben B. Corson. Process for Hydrogenating Hydro- carbons. 2,275,182 With Raymond E. Schaad. Manufacture of Catalysts. 2,283,142 With Herman Pines. Isomerization of Normal Butane. 2,283,143 With Herman Pines. Isomerization of Normal Butane. 2,290,189 With Herman Pines. Conversion of Straight Chain Ole- fins to Isoparaffins. 2,291,254 With Herman Pines. Conversion of Hydrocarbons. 2,297,769 With Vladimir Haensel. Hydrogenation of Alkyl Aryl Ketones. 2,298,383 With Herman Pines. Treatment of Hydrocarbons.

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VLADIMIR NIKOLAEVICH {PATIEFF 135 1943 2,311,232 With Herman Pines. Manufacture of Catalysts. 2,315,078 With Herman Pines. Conversion of Hydrocarbons. 2,316,247 With Herman Pines. Isomerization of Paraffins. 2,316,248 With Herman Pines. Isomerization of Paraffins. 2,318,225 With Herman Pines. Production of Isobutane. 2,318,226 With Herman Pines. Production of Isobutane. 2,318,781 With Herman Pines. Treatment of Hydrocarbons. 2,322,025 With Aristid V. Grosse. Conversion of Hydrocarbons. 2,325,122 With Herman Pines. Treatment of Butane. 2,327,188 With Herman Pines. Treatment of Paragons. 2,327,189 With Vladimir Haensel. Treatment of Hydrocarbons. 2,329,858 With Louis Schmerling. Treatment of Hydrocarbons. 2,332,467 With Carl B. Linn. Production of Ethers. 2,334,099 With Herman Pines. Treatment of Hydrocarbons. 2,334,100 With Vladimir Haensel. Hydrogenation of Ketones. 2,335,246 With Vladimir Haensel. Hydrocarbon Conversion. 1944 2,340,557 With Herman Pines. Conversion of Hydrocarbons. 2,341,782 With Louis Schmerling. Treatment of Hydrocarbon Oils. 2,342,865 With Herman Pines. Alkylation of Hydrocarbons. 2,345,751 Production of Diolefinic Hydrocarbons. 2,346,701 With Herman Pines. Treatment of Propane. 2,347,266 With Louis Schmerling. Isomerization of Para~nic Hy- drocarbons. 2,348,700 With Herman Pines. Treatment of Butane. 2,348,702 With Louis Schmerling. Hydrogenation of Hydrocarbon Materials. 2,349,834 With Louis Schmerling. Treatment of Hydrocarbons. 2,352,199 With George S. Monroe. Production of Toluene. 2,352,200 With George S. Monroe. Production of Toluene. 2,353,899 With Herman Pines. Isomerization of Paraffin Hydro- carbons. 2,355,219 With Vladimir Haensel. Hydrogenation of Aryl Car- boxylic Acids. 2,356,001 With Herman Pines. Conversion of Hydrocarbons.

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136 BIOGRAPHICAL MEMOIRS 2,358,011 With Louis Schmerling. Treatment of Hydrocarbons. 2,361,065 With Louis Schmerling. Alkylation of Aromatic Hydro- carbons. 2,366,126 With Herman Pines. Production of Cycloolefinic Hydro- carbons and Aromatic Hydrocarbons. 1945 2,366,531 2,366,731 2,366,736 2,369,495 2,369,691 2,374,433 2,374,600 2,375,041 2,381,828 2,382,318 2,382,881 2,382,882 2,384,337 2,385,300 2,386,007 2,386,468 2,386,957 2,388,937 2,389,780 2,391,508 2,391,509 With Vladimir Haensel. Dehydrogenation of Hydrocar- bons. With Carl B. Linn. Alkylation of Isoparaffins. With Carl B. Linn. Alkylation of Isoparaffins. With Louis Schmerling. Treatment of Aromatic Hydro- carbons. With Louis Schmerling. Catalyst Manufacture. Production of Butadiene. With Louis Schmerling. Alkylation of Aromatic Hydro- carbons. With Louis Schmerling. Alkylation of Aromatic Hydro- carbons. With Carl B. Linn. Conversion of Hydrocarbons. With Raymond E. Schaad. Alkylation of Benzene. With Herman Pines. Isomerization of Saturated Hydro- carbons. With Herman Pines. Isomerization of Saturated Hydro- carbons. With Herman Pines. Manufacture of Catalysts. With Herman Pines. Conversion of Hydrocarbons. With Louis Schmerling. Production of Aromatic Ke- tones. With Raymond E. Schaad. Process for Isomerizing Nor- mal Butenes to Isobutene. With Vladimir Haensel. Dehydrocyclization of Aliphatic Hydrocarbons. With Louis Schmerling. Treatment of Hydrocarbon Oils. With Vladimir Haensel. Conversion of Ethylene. With Herman Pines. Manufacture of Butadiene. With Herman Pines. Manufacture of Butadiene

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VLADIMIR NIKOLAEVICH {PATIEFF 137 1946 2,392,924 With Herman Pines. Production of Isobutane. 2,394,691 With Herman Pines. Destructive Hydrogenation of Poly- cyclic Hydrocarbons. 2,399,224 With Vladimir Haensel. Conversions of Hydrocarbons. 2,399,741 With Herman Pines. Conversion of Dicyclic Dihydro- terpenes to Cyclopentene Hydrocarbons and Pentameth- ylene Hydrocarbons. 2,401,636 With Vladimir Haensel. Process for Reducing the Olefin Content of an Olefinic Distillate. 2,402,051 With Louis Schmerling. Catalysts. 2,402,847 With Louis Schmerling. Alkylation of Aromatics with a Ferrous Chloride Catalyst. 2,403,439 With George S. Monroe. Process for Isomerizing Mono- olefins. 2,404,498 With George S. Monroe. Production of Toluene. 2,404,536 With Louis Schmerling. Alkylation of Hydrocarbons. 2,404,537 With Louis Schmerling. Treatment of Hydrocarbons. 2,404,538 With Louis Schmerling. Manufacture of Arylalkene Hy- drocarbons. 2,404,927 With Louis Schmerling. Manufacture of Isoparaffins. 2,406,630 With Herman Pines. Production of Cycloolefinic Hy- drocarbons and Aromatic Hydrocarbons. 2,406,631 With Herman Pines. Production of Cycloolefinic Hy- drocarbons and Aromatic Hydrocarbons. 2,406,632 With Herman Pines. Production of Cycloolefinic Hy- drocarbons and Aromatic Hydrocarbons. 2,406,639 With Louis Schmerling. Catalytic Reactions. 2,410,445 With Herman Pines. Production of Diolefinic Hydro- carbons by Reaction of an Alcohol with an Acetylenic Hydrocarbon. 2,410,553 With Louis Schmerling. Manufacture of Alkylated Aro- matic Compounds. 2,410,554 With Herman Pines. Production of Aromatic Com- pounds. 2,411,047 With Carl B. Linn. Alkylation of Aromatics. 2,412,012 With Louis Schmerling. Preparation of Aldehydes and Acetals.

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138 2,419,142 2,419,690 2,420,749 2,421,936 2,421,946 BIOGRAPHICAL MEMOIRS 1947 2,416,106 With Carl B. Linn. Polymerization of Olefinic Hydro- carbons in the Presence of Boron Fluoride and an Acid Fluoride of a Metal. With Carl B. Linn. Treatment of Alkyl Ketones to Form Condensation Products Thereof. With Herman Pines. Conversion of Hydrocarbons. With Herman Pines. Treatment of Monocyclic Olefinic Hydrocarbons. With Vladimir Haensel. Production of Octenes. With Carl B. Linn. Polymerization of Olefinic Hydro- carbons. 2,422,435 With Herman Pines. Manufacture of Cyclohexene Ox- ides. 2,422,670 With Vladimir Haensel. Selective Demethylation of Paraffinic Hydrocarbons. 2,422,671 With Vladimir Haensel. Process for Lowering the Molecular Weight of Non-Aromatic Hydrocarbons. 2,422,672 With Vladimir Haensel. Selective Demethylation of Tri- methylpentanes to Form Triptane. 2,422,673 With Vladimir Haensel. Treatment of Alkyl Aromatic Hydrocarbons. 2,422,674 With Vladimir Haensel. Selective Demethylation of Saturated Hydrocarbons. 2,422,675 With Vladimir Haensel. Selective Demethylation of Saturated Hydrocarbons. 2,427,791 With Louis Schmerling. Hydrogenation of Halogenated Hydrocarbons. 2,428,279 With Carl B. Linn. Alkylation of Aromatics. 2,430,190 With Louis Schmerling. Alkylation of Phenols. 2,431,754 With Carl B. Linn. Condensation of Alkyl Ketones in Presence of Aqueous Ammonium Halide Solutions. 2,431,756 With Herman Pines. Treatment of Terpenic Hydrocar- bons. 1948 2,434,409 With Carl B. Linn. Process for Purifying a Hydrocarbon Mixture Containing Small Amounts of Organic Fluorine Compounds.

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VLADIMIR NIKOLAEVICH IPATIEFF 139 2,435,443 With Herman Pines. Separation of Gem Cyclic Hydro- carbons from Nongem Cyclic Hydrocarbons by Selective Dehydrogenation. 2,438,215 With Louis Schmerling. Treatment of Polyalkyl Aro- matics. 2,439,982 With George S. Monroe. Production of Dehydrated Castor Oil. 2,441,663 With Vladimir Haensel. Process for Purifying Saturated Hydrocarbons Involving Selective Demethylation. 2,442,878 With Louis Schmerling. Manufacture of Alkylated Aro- matic Hydrocarbons. 2,443,732 With Carl B. Linn. Dehydration of Alkyl Ketones. 2,444,509 With Vladimir Haensel. Composition of Matter. 1949 2,465,475 With Herman Pines. Purification of Cyclic Olefinic Ke- tones. 2,476,416 With Herman Pines. Isomerization of Paraffin Hydro- carbons by Contact with Catalyst Comprising Aluminum Chloride and Ferric Chloride. With George S. Monroe. Dehydration of Alcohols. With Herman Pines. Manufacture of Bicycloalkyl Aro- matic Compounds and Hydrocarbons. 2,478,270 2,480,268 1950 2,502,569 With Herman Pines. Manufacture of Alkylcyclopentane Hydrocarbons. 2,514,546 With Herman Pines. Production of Cycloalkylperhy- droindan Hydrocarbons. 2,519,576 With Herman Pines. Production of Arylindans. 2,519,577 With Herman Pines. Production of Arylindan Hydro- carbons. 2,526,895 With Herman Pines. Production of Polycyclic Aromatic Hydrocarbons. 2,526,896 With Herman Pines. Production of Diaryl Alkanes. 2,526,897 With Herman Pines. Production of Aryl Indans. 1951 2,538,248 With George S. Monroe. Isomerization of Olefins.

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140 BIOGRAPHICAL MEMOIRS 2,557,505 With Herman Pines. Production of Diarylalkanes. 2,563,037 With George S. Monroe. Conversion of Aromatic Amines to Aromatic Hydrocarbons. 2,578,207 With Herman Pines. Di-(Alkylphenyl)-Alkenes. 1952 2,584,103 With Herman Pines. Alkylation of Aromatic Hydrocar- bons. 2,586,535 With Herman Pines. Catalytic Hydrogenation of Aro- matic Hydrocarbons in a Stainless Steel Reactor. 2,587,577 With Herman Pines. Production of Arylindanes. 2,622,110 With Herman Pines. Di~cycloalkyl~alkanes. 1953 2,630,460 With Herman Pines. 4-Alkylbiphenyls. 2,631,174 With Herman Pines. Polycyclic Benzene Hydrocarbons. 1954 2,671,114 With Herman Pines. Bis~hydronopyl) Ether. 2,671,120 With Herman Pines and Bruno Kvetinskas. Noncatalytic Isomerization of Aromatic Compounds. 2,694,730 With Herman Pines. Bicyclooctene Derivatives. 1956 2,750,261 With George S. Monroe. Hydrogen. 2,751,406 With Herman Pines. Oxidative Condensation. 2,758,140 With Herman Pines and Bruno Kvetinskas. Noncatalytic Condensation of Aromatic Compounds with Unsaturated Hydrocarbons.

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