Petroleum. Miscellaneous - Analytical Chemistry (ACS Publications)

SO-SO%. With two of these test engines, one man can make four ON determinations in the time formerly needed for a single measurement. The resulting increase in precision allows optimizing octane specifications with a resulting saving in processing costs. Automatic control of a fractionating column producing an aromatic precursor stream is based on GLC analysis of the stream sample following catalytic hydrogenation, according to Boyd (6L). The automatic removal of dissolved nonvolatile substances from liquid process sample streams to be chromatographed is described by Cayanus and Villalobos (8L). A special 10-port valve simultaneously isolates the sample valve from the column and flushes the sample vaporization area with a measured amount of solvent, which is discarded to a separate vent. Smith and Villalobos (64L) utilize a somewhat similar but simpler scheme to overcome the accumulation of high-boiling residues in the inlet of a process stream GLC instrument. Steam or a suitable solvent is automatically used in each analysis cycle to remove any residue from the tubing section that forms the analyzer inlet. T o pyrolyze samples of polymers and other high-molecular-weight samples prior to GLC analysis of the products, Folmer and Azarraga (BOL) employed a pulsed ruby laser. The resulting chromatograms were simpler and allow greater distinctions to be made between similar substances. Pendry (60L) developed a “StopStart” automatic gas chromatograph for handling 1- to 10-pl samples of multicomponent mixtures; when a peak is eluted the gas flow is stopped and the pressure is equalized to atmospheric, allowing the use of a conventional I R spectrometer to provide high-resolution spectra. A mass spectrometer can be similarly used to characterize the eluted material. A versatile high-speed process chromatograph was described by Sanford et al. (67L), capable of providing 14 component analyses in 4 minutes on each of 8 process streams. Experience with this and similar instruments has shown them to be highly reliable despite their complexity; they are particularly applicable to the automatic control of distillation columns for light hydrocarbons and petrochemical feed stocks. The current trend in design and application of process chromatographs appears to be toward simpler instruments to measure a few key components in only a single stream. Diets (16L) describes a computer-controlled system comprising seven high-accuracy, single stream chromatographs. The computer supervises the operations of the chromatographs, including the operation of sample valves, backflush, and

injection of standard samples. It also performs the needed calculations, employing teletypewriter printout and automatic alarm messages. Laboratory Automation. Linking advanced and automatic laboratory instruments to computers for the purposes of maximum utilization of the instruments and to avoid laborious calculations of results is a major trend. There are as many detailed schemes as there are practitioners. What is becoming increasingly clear is that large analytical service laboratories and quality-control centers can thus achieve marked increases in service capability and data-handling efficiency. Because laboratory automation of this type has entailed little development of instruments so far, a review of the literature is outside the scope of this section. It is to be expected, however, that the wedding of computers to instruments will soon bring forth a new generation of advanced automatic laboratory instruments.

Miscellaneous R. W. King Sun Oil Co., Marcus Hook, Pa.

Contamination Control. This material is intended primarily to cover methods for the analysis of contaminants in petroleum products and in the immediate refinery environment. Although some papers of wider scope are included, it does not attempt to deal comprehensively with the general analytical problems of air and water conservation that may arise from the transportation, storage, and use of petroleum products. These are better handled as a part of the broader subject of environmental pollution. Chovin ( 1 4 N ) has reviewed methods for the analysis of many of the common pollutants of industrial atmospheres. Procedures for sulfur dioxide, hydrogen sulfide, dusts, aerosols, oxides of nitrogen, ammonia, ozone, fluorine compounds, hydrocarbons, tars, carbon monoxide, nitrogen peroxide, and aldehydes are covered. Bethea and Meador (6121) have recommended a chromatographic system of three columns for the analysis of a mixture of nitric and nitrous oxides, nitrogen dioxide, chlorine, hydrogen chloride, fluoride, and sulfide, sulfur dioxide, and carbon dioxide in air. Single columns and tandem combinations are suggested for less complex mixtures. The use of infrared spectrometry for the analysis of ten of the more common gaseous air pollutants, including benzene, sulfur dioxide, hydrogen sulfide, propane, acetylene, and some of their mixtures, has been reported by Steger and Kahl (67iV). The determination of the oxides of sulfur and hydrogen sulfide in both

stack gases and industrial atmospheres has received a great deal of attention. The determination of atmospheric concentrations of sulfuric acid aerosol was described b y Scaringelli and Rehme (6ZM). Schneider (53111) has developed a simple portable apparatus for determining sulfur oxides in flue gases. The sulfur trioxide is trapped in a heated sodium chloride filter, the sulfur dioxide absorbed in hydrogen peroxide solution, and the sulfur oxides are determined as sulfuric acid by titrating with sodium hydroxide. Vasil’eva et al. (6251) use gas chromatography to determine hydrogen sulfide and carbon dioxide in refinery gases. Adams ( 2 M ) described a n automated, sequential subtractive sampling system for the determination of sulfur dioxide, hydrogen sulfide, methanethiol, dimethyl sulfide, and dimethyl disulfide. The gases are analyzed by coulometric titration with bromide ion before and after passage through each subtraction reagent. Two systems that are capable of monitoring hydrogen sulfide in stack gases have been reported in the literature ( 1 O M ) . I n the device developed by Murray and Risk, the sample stream is divided into two parts and the hydrogen sulfide in one catalytically oxidized to sulfur dioxide. Comparison of the ultraviolet spectrum with that of the unoxidized stream gives direct data on the hydrogen sulfide content. The analyzer developed by Thoen and Haas is essentially a modified electrolytic titrator in association with a sampling probe, and has a sensitivity of bet’ter than 5 parts per billion a t 700 O F . The problems of monitoring sulfur dioxide concentrations in stack gases have been reviewed by Kotnick and Scheck (34M). They conclude that instruments based on wet chemical methods have serious drawbacks and describe a number of commercially available monitors based on other detection principles. Jackson and coworkers ($OM) monitor the concentration of sulfur trioxide in stacks with a device that operates by absorbing the sulfur trioxide in aqueous isopropanol, reacting the sulfate ions with solid barium chloranilate, and determining the acid chloranilate ion photometrically. Efforts to reduce atmospheric contamination have resulted in the enactment of a solvent law in Los Angeles County, termed Rule 66. It places limitations on solvent emissions and on solvent formulations used within its jurisdiction, and as a consequence, creates some analytical problems. MacPhee and Kuramoto (4SiV) describe two procedures developed for use in conjunction with the rule. For emissions, a total combustion method is used. For solvent formulations, a column-chromatographic screening is first performed to measure types of

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compounds, e.g., oxygenates, aromatics, olefins, and paraffins. This helps t o select the conditions for a lengthier gas chromatographic method that provides the ultimate analysis of individual compounds. Esposito ( d f M ) has also reported the use of gas chromatography for the determination of the amount of photochemically reactive hydrocarbons (toluene, ethylbenzene) and total aromatics in petroleum solvents and thinners. The testing of industrial effluent waters has assumed considerable importance as we undertake to reverse the deterioration of natural waterways both here and abroad. Methods for the detection and quantitative determination of mineral oil in water have been reviewed b y Lawerenz (38144). Goebgen and Brockmann (dSd1) have also examined methods for the determination of hydrocarbons of both gasoline and gas oil origin. They recommend that the volatile hydrocarbons be determined as carbon dioxide after stripping from the water sample and subsequent combustion. The heavy oils are then determined by thin-layer chromatography. Yoshii et al. (66.11) describe the construction of a n instrument for the automatic determination of the oil content of waste water. The sample is completely emulsified and the oil content estimated from the ratio of the intensities of transmitted and reflected light. They claim a n accuracy of f5% at 100 ppm of oil. Bauer and Driescher ( S X ) use a similar approach, save that in their equipment the oil content is estimated from the intensity of the fluorescence at 365 nanometers. Sher (6451)has successfully used gas chromatography to determine less than 5 ppm of hydrocarbons in cooling tower water. Samples were taken a t atmospheric pressure in glass or low porosity plastic containers, an internal standard was added, and 15-20 microliters were charged to a chromatograph equipped with a n Apiezon L column and flame ionization detector. Taras and Blum (59-11) extended the scope of the standard APHA method for the determination of grease to include emulsifying oils by saturating the acidified sample with sodium chloride before filtration. Petrochemical waste water analysis has received the attention of several investigators. Sugar and Conway (56M) described a scheme for the gas chromatographic separation and identification of complex mixtures of organic compounds in plant effluents b y direct injection onto various types of columns. B y introducing a n intermediate concentration stage in which nitrogen is used to strip the hydrocarbons from the water sample, Krichmar and Stepanenko (35111) were able to effect a 3-4 order-of-magnitude improvement in the sensitivity of gas chromatographic 196R

methods for benzene, toluene, ethylbenzene, diethylbenzene, and isopropylbenzene. The spectrophotometric determination of traces of benzene in water was reported by Sono et al. (66111). The procedure involves nitration of the benzene t o m-dinitrobenzene and colorimetric determination of the latter. High temperature pyrolysis of a water sample, followed by a gas chromatographic separation and measurement of methane, a major pyrolytic product, has been used b y Lysyj and coworkers (40144) to detect industrial pollutants. The method is based upon the fact that the yield of methane from common contaminants such as hydrocarbons, alcohols, and other organic compounds is considerably higher than that from the natural organic content of water. Spectrophotometric apparatus for the continuous monitoring of plant effluents has been described b y several authors. Saltzman (51M) reported the use of differential ultraviolet photometry to monitor aromatic compounds, while Cowlin and Coomber (1651) described a device for the continuous determination of oil content that depends upon detection and measurement of the visible fluorescence emitted when the sample stream is subjected to ultraviolet irradiation. The Technicon AutoAnalyzer has become a fairly popular tool for both the automated laboratory application of conventional chemical methods and for continuous monitoring. Casapieri et al. (1 1 M ) discuss the use of the AutoAnalyzer to measure 1-10 ppm sulfide in industrial effluent samples a t the rate of 40 per hour. The determination of Chemical Oxygen Demand (COD) using an AutoAnalyzer has been reported by Hertzog (28111). A very sophisticated system that permits the automatic and simultaneous measurement of up t o 12 stream pollutants was described by Marten (4531). The identification of the source of petroleum pollutants in estuarine waters and on beaches has recently become a n analytical problem of some importance. Kawahara ( S S M ) used comparative ratios of infrared absorbances to distinguish between contaminants, particularly asphalt and heavy residual oil. Hellmann ( 2 7 X ) has discussed the capabilities and limitations of infrared spectrometry in determining mineral oils and fuels in surface waters. Internal reflection infrared spectrometry has been used by Mattson et al. (47M) to distinguish the sources of contamination in the Santa Barbara Channel. The technique has the advantage of being able to accommodate samples contaminated with solids. Maehler and Greenberg (41M) have described in detail a number of qualitative comparative procedures which permit the clear differentiation of petroleum products in water. They suggest a sequential


scheme which includes gas chromatographic analysis of vapor space gas, and solvent extraction followed by infrared and paper chromatographic examination. Matthews (46M) uses a thinlayer chromatographic method for systematic identification of petroleum and coal-tar oils and residues. Guinn and Bellanca (966M) have reported some promising exploratory work t h a t depends upon trace element characterization using neutron activation analysis. The concentrations of V, &In, Na, Co, Sb, As, Cu, and Zn were used to differentiate between a number of marine fuel oils. A more comprehensive study is planned. An analytical scheme for the identification of slop oils was described by Cole ( 1 5 M ) . The procedure uses gas chromatography and infrared spectrometry to produce “finger-prints” of the unknown material which are then compared with a library of chromatograms and spectra. Ramsdale and Wilkinson (4.9111) report that gas chromatography alone can be used to distinguish the three major sources of beach pollution, Le. , materials resulting from the discharge of crude oils, fuel oils, or cargo residues at sea. Samples containing major amounts of sand and/or water can be analyzed rapidly without pretreatment. Brunnock et al. (8111) also depend heavily on gas chromatography, but in addition use measurements of the vanadium, nickel, and sulfur content. Petroleum products intended for use as direct or indirect food additives require careful analytical scrutiny for traces of polycyclic aromatics, and several investigators have directed their attention to this problem. Marletta and Gabrielli (44M) and van Langermeersch ( S S M ) reviewed extensively the separation and determination of polycyclic hydrocarbons, and discussed some applications t o food products, asphalt, tar, and water. Soos and Cieleszky (56M) gave details of a method for the determination of polycyclic aromatics in foods and food-packaging materials involving extraction, column and thinlayer chromatography, and fluorescence spectrometry.

Specifications and Method Standardization. T h e redundancy of petroleum products specifications and test analyses was discussed by Jenkins ( S f M ) who covered the general principles involved in reducing the number of analytical tests; b y Templeman ( 6 0 M ) , and by Chalfant (12~1f)who emphasized the role of stream analyzers, particularly process chromatographs, in the specifications arena. Wernimont (64M) reviewed the role of statistical design in the development and evaluation of specification test methods. The graphical evaluation of the results of interlaboratory testing of a method was described by Becker et al. ( 6 M ) , while

Dyroff (19M) set forth statistical guidelines for resolving product quality disputes. Data Handling. T h e use of computers for the acquisition and calculation of analytical data is expanding rapidly and a number of significant papers have appeared during this review period. Analytical information retrieval was the subject of reports by Erley (20M) who described a fast searching system for the ASTM infrared data file, and by McKinney and coworkers (4231) who developed a system for the storage and retrieval of information from Preston gas chromatography abstract cards. A number of computer programs of general analytical import have been described. Buchanan and Maher (9M) devised a program t o facilitate the analysis of complex mixtures by gas chromatography in conjunction with the successive extraction of compound types from the sample. The input data consist of the total number of peaks, the number of treatments, and the peak areas before and after each treatment. A computer program to convert raw gas chromatographic values into simulated distillation data was reported by Gouw et al. (24M). Chapman (19M) briefly reviewed the application of computers in the study of mass spectral data. The use of computer techniques in highresolution mass spectrometry was the subject of papers by Aczel and coworkers ( 1 M ) , Tunnicliff and Wadsworth (61M) and by Hites and Biemann (29.M). Crawford and Morrison discussed the identification of an unknown by computer searching of a spectral reference library (17M) and the computerassisted identification of molecular class from mass spectral data ( 1 8 X ) . On-line data acquisition and processing systems are now becoming somewhat commonplace. A survey by Jones (%?AI) covers the principles of on-line computers; software for processing instrumental data; applications to gas chromatography, mass spectrometry and NMR spectrometry; and present and future trends. Otcasek (48M) and Bonzom (7121) described systems for the operation of, and logging and computing of data from, an engine test laboratory. The acquisition and processing of gas chromatographic data has been the subject of reports by Hadley and Book (26M), Baumann et al. ( 4 M ) and Raymond and coworkers ( 6 0 M ) . Gill (22M) has discussed the automation of gas chromatography in detail, and stresses the need for improvements in the performance-limiting areas of automatic sampling, retention time reproducibility, and detector performance. General purpose laboratory data acquisition and control systems were described by Lauer and Osteryoung ( 3 7 M ) , by Weihman and coworkers

(24B) Kulieva, R. A., Vaisberg, K. M., Portnova, T. N., Ashumov, G. G., Musaev, I. A., Azerb. Khim. Zh., 1969, 50. (25B) Litovchenko, A. Ye., Gazov. KhroLITERATURE CITED matog., 1969 (9), 187; C.A., 72, 4870t Introduction (1970). (26B) Mahmoud, B. H., Ahmed, L. A., (1A) Cambrill, C. M., ANAL.CHEM.,35, J. Chem. U.A.R., 11, 345 (1968); l l l R (1963). C.A., 71, 23432x (1969). (2A) Zbid., 37, 143R (1965). (27B) RIanjarrez, A., Joseph-Nathan, P., (3A) LeTourneau, R. L., ibid., 29, 684 Rivers, J., Berra, R., Rev. Znst. Mez. (1957). Petrol., 1, 59 (1969). (4A) Zbid., 31, 730 (1959). (28B) Markhasin, I. L., Svirskaya, 0. D., (5A) Zbid., 33, 92R (1961). Strade, L. N., Kolload. Zh., 31, 294 (6A) Levin, H. L., ibid 25, 47 (1953). (1969). (7A) Zbid., 27, ,599 (195b). (29B) Mediterranea S. p. A. Raffineria (8A) Tuemmler, F. D., ibid., 39, l57R Italiana Petroli, British Patent 1,125,(1967). 442, May 24, 1966. (9A) Zbid., 41, l52R (1969). 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CHIN., 41, 800 R., Medvedeva, V. D., Talalaev, E. I., ( 1969). Zzv. Akad. Nauk Turkm. S S R , Ser. (1lB) Decastille, &I., Diboun, hI., Fiz.-Tekh., Khim. Geol. Nauk, 1969, 36. Guichard-Loudet, X., Rev. Znst. Fr. Guichard-Loudet. (41B) Sevast’yanova, G. V., Ivchenko, E. Petrole Ann. Combust. Liquides, 24, 1177 G., Tr. Bashkir. Nauch.-Zssled. Znst. ( 1969). Pererab. Nefti, 1968, 14; C.A., 69, (l2B) Diskina, D. E., Gazov. Khromatog., 68745b (1968). 1968 ( 8 ) , 21; C . A . , 71, 62697g (1969). (42B) Sevast’yanova, G. V., Popova, L. (13B) Done, J. N., Reid, W. K., Amer. N., ibid., p 29 ; C.A., 69, 68737a (1968). Chem. SOC.,Diu. Petrol. Chem., Prepr., (43B) Shevchenko, E. F., Kham. Tekhnol. 15, A242 (1970). Topl. Masel, 13 (4), 8 (1968). (14B) Efendieva, Z. G., Satter-Zade, A. (44B) Skripnyak, E. I., Khim. Seraorg. D., Satter-Zade, I. S., Uch. Zap. Azerb. Soedin., Soderzh. Neftyakh Nefteprod., Gos. Univ., Ser. Khim. iVauk, 1968, 33; 8.256 (1968). C.A., 72, 123598~(1970). (4,5B) Slobodin, Ya. >I Kovyazin, ., V. E., (15B) Erwin, A. B., Oal Gas J., 65, (36), Neftekhimiya, 9, 921 (1969). 186 (1967). (46B) Smekhova, L. M., Geol. Nefti (16B) Gorski, L., Janczyszyn, J., Loska, Gaza, 13,28 (1969). L.. Radiochem. Radioanal. Lett.. 1. 99 (47B) Thein. M.. Union Burma J . Sci. ilb69i. Technol.. 1. 187 (1968). (17B.) Hanna, A. H., El-Fayoumy, G. F., (48B) Zbid., p 399. hlahmoud, B. H., J . Chem. U.A.R., 12, (49B) Triems, K., Chem.-Tech. (Berlin), 24.5 (1969); C.A., 71, 126789~(1969). 20,596 (1968). (18B) Hoering, T. C., Carnegie Znst. (50B) Ulm, V. A., Tr. Vses. Neft. Nauch.Washington, Yearb., 1968-1969 (Pub. Zssled. Geologorazved. Znst., 1968, 173; 1970), 303. il9B) Hustiu. G.. Petrol. Gaze (Bucharest). C.A., 72, 57379w (1970). (5lB) Vasil’eva, V. F., Khim. Tekhnol. ’ 20,’73O ( I ~ & I ) ; ’ C . A 72,68&1ih ., (i97oj: Topl. Masel, 14 ( 8 ) , 59 (1969). (20B) Korotkii, A. G., ,Sergienko, S. R., (52B) Zul’fugarly, D. I., Getseu, V. V., Khramova, E. V., Taimova, B. A., Zzv. Uch. Zap. Azerb. Gos. Univ., Ser. Khim. Akad. Nauk Turkm. S S R , Ser. Fiz.Nauk, 1967, 86; C.A., 70, 107950g Tekh., Khim. Geol. Nauk, 1969, 52. (21B) Krayushkin, V. A., Kazakov, S.B., (1969). Nefte azov. Geol. Geojiz., 1968, 25. Engine Fuels (22B) uklinskii, A. Ya., Pushkina, R. A., Tr., Volgograd, 1Vauch.-Zssled. Neft. (IC) Abrysowska, E., Mayer, L., Nafta Gasov. Prom., 1969, 270; C.A., 71, (Katowice),25, 15 (1969). (2C) Aleksandrov, A. N., Tisovskii, G. I., 126783s (1969). (23B) Kuklinskii, A. Ya., Pushkina, R. N A S A Tech. Transl., F-11,855 (1968); A., Filippov, V. P., Neftepererab. NefteA.P.Z.A., 16, 470 (1969). (3C) Amos, R., J. Inst. Petrol., 54, 9 khim. (Moscow), 1968, 6 ; C.A., 69, ( 1968). 88524g (1968).

(63hl) and b y Levine and Sutton (39M).

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ANALYTICAL CHEMISTRY, VOL. 43, NO, 5, APRIL 1971

197 R

(4C) Aronovich, Kh. A,, Neftepererab. Neftekhim. (Moscow), 1969, 6; A.P.Z.A., 17, 5388 (1970). (5C) Ballinger, P. R., Whittemore, I. hl., Amer. Chem., SOC.,Diu. Petrol. Chem., Prepr., 13, 133 (1968). (6C) Bartels, T. T., Wilson, C. E., At. Absorption Newslett., 8, 3 (1969). (7C) Barton, R. K., Lestz, S. S.,Duke, L. C., S A E (SOC.Auto. Eng.) J . , 78, 97 (1970). (8C) Bespolov, I. E., Khaikin, M. D., Komarov, B. I., Medvedev, S. P., Khim. Tekhnol. Topl. Masel, 14 (6), 42 I1 RBR’I. \----,-

(9C) Bol’shakov, G. F., Litvinov, V. L., ibid., 13 (5), 58 (1968). (1OC) Britten, J., ANAL.CHEY.,40. 960 (1968). (1lC) Burt, R., Troth, K. A., S A E (SOC. Auto. Eng.) Meet., 1968, Pap. 680464, 13 PP. (12C) Castello, G., Chzm. Ind. (Mzlan), 51, 700 (1969)) A.PZ.A., 17, 224 (1970). (13C) Chertkov, Ya. B., Ignatov, V. M., Im. Vyssh. Ucheb. Zaved., Nejt Gaz, 12, 49 (1969), A.P.I.A., 16,74.52 (1969). (14C) Chertkov, Ya. B., Zrelov, V. N., hlarinchenko, K. I., Shchagin, V. )I., Rybakov, K. V., Khzm. Seraorg. Soedan. Soderzh. Sejtyakh iyefteprod., 8 , 429 (1968). (15C) Coord Res. Counc. Rep., 412, 87 pp. (July, 1968). (16C) Costa, D. P., Combrtstzon, 39, 18 (Mar., 1968). (l7C) Danilov, I. N., Khzm. Tekhnol. Top/. illasel, 13, (lo), 53 (1968). (18C) Ibzd., 14 ( 8 ) , 45 (1969). (19C) Danilov, I. N., 1Ycftepercrab. N e j t e khzm. (~Woscow),1969, 45; A.P.Z.A., 17,3968 (1970). (20C) Danilov, I. S . , Gorn, F. K., Khzm. Tekhnol. Topl. Masel, 14 (4), 53 (1969). (2lC) Dulaney, C., Nathan, C. C., 0 2 1 Gas J . , 68 (17), 89 (1970). (22C) Ebersole, G. D., zbtd., 67 (45), 234 11969) \--

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(23C) Edwards, F. R., Chem. lnd. (London), 1970, 183. (24C) Fenske, E. R., Johnston, W. C., Mater. Res. Stand., 9 (lo), 32 (1969). (272) Gardner, L., J . Inst. Petrol., 55, 418 ilR6S’i.

(28Cj Girko, I. P.,”Shurupova, 0. V., ibid., 13 (9), 56 (1968). (29C) Hinkamp, J . B., Riggs, R. J., Hydrocarbon Process., 47 ( l l ) , 233 (1968). (30C) Hovemann, F., Graefen, H., Werkst. Korros., 20, 221 (1969). (31C) Instrum. Pract., 24, 194 (1970). (32C) Jenkins, G. I., Ger., Offen. 1,909,486, Sep. 18, 1969. (33C) Jenkins, G. I., J . Inst. Petrol., 54, 14 (1968). (34C) Ibid., p 80. (35’2) Ibid., 55, 166 (1969). (36C) Jenkins, G. I., Walsh, R. P., Hydyocarbon Process., 47 (5), 161 (1968). (37C) Jenkins, G. I., White, M. &I., J . Znst. Petrol., 55, 153 (1969). (38C) Johnston, A. A., Stavinoha, L. L., SAE (SOC.Auto. Eng.) Combined Fuels and Lubric. and Transp. Meet., 1969, Pap. 690758, 8 pp. (39C) Jollivet, J., Znd. Petrol., 36, 81 (1968); A.P.I.A., 16, 1294 (1969). (40C) J . Inst. Petrol., 55, 36 (1969). (41C) Ibid., p 330. (42C) Khlestunov, P. T., Kejiepererab. ,I‘eftekhim. (Moscow), 1969, 34; A.P.I.A.? 17,3967 (1970). (43C) Kyriakopoulos, G. B., J . Znst. Petrol., 54, 369 (1968). 198R

(11D) Berthold, P. H., Drescher, K., (44C) Ibid., p 376. Freiberg. Forschungsh., 1966, 15. (45C) Kyuregyan, S. K., Marenova, M. (12D) Bley, W., Erdoel Kohle, 22, 205 AI., Zh. Prikl. Spektrosk., 10,313 (1969); (1969). B.A.A., 18,4148 (1970). (13D) Bohlmann, H., Saxe, H., Thomas, (46C) Lando, J. L., Oakley, H. T., W. D., Schmierstoffe Schmierungstech., Amer. Chem. SOC.,Diu. Petrol. Chem., 1968,38; C.A., 71,72596n (1969). Prepr., 14, 33 (1969). (14D) Bondarchuk, Yu. V., Barannik, (47C) LePera, 31. E., J . Gas Chromatogr., V. P., Izv. Vyssh. Ucheb. Zaved., Neft 6, 335 (1968). Gaz, 11, 82 (1968); A.P.I.A., 15, 10182 (48C) Lisnyanskii, L. I., Bol’shakov, G. F., Khim. Seraorg. Soedin., Soderzh. (1968). (l5D) Bondy, C., Robin, G., Vidal, J. P., Nejtyakh Nefteprod., 8, 438 (1968). French Patent 1,500,048, Nov. 3, 1967. (49C) Rtaynard, J. B., Sanders, W. K., (16D) Butler, J. hI., Wheeler, G., Jr., J . Air Pollut. Contr. Ass., 19, 505 (1969). ROSS, W. D., ANAL. CHEY.,40, 466 (BOC) Nikolaeva, V. G., Dukhnina, A . Y., (1968). Levinson, G. I., Tr., Vses. Nauch.(17D) Buttlar, R. O., Cantley, R. E., Issled. Inst. Pererab. s e f t i , 1967, 109; NLGZ Spokesman, 33, 18 (1969). C.A., 68, 4194.5j (1968). (18D) Carroll, J. G., Lubric. Eng., 24, (51C) Nottes, E. G., Erdoel Kohle, 22, 359 11968). 404 (1969). (19D) ‘Cueilar, J. P., Ku, P. hi., ASME, (32C) Oil Gas J . , 65 (32), 139 (1967). (Amer. SOC.Nech. Eng.)-ASLE (Amer. (53C) Peters, H., Erdoel Kohle, 22, 541 SOC. Lubric. Eng.) Lubric. Conf., (1969). Atlantic City, 1968. (54C) Podlipskii, L. A., Ropyanaya, 11. (20D) DeLuca, B., Riv. Eng., 1969, 713. A,, Kruglova, L. I., Khim. Tekhnol. (21D) Dromgold, L. D., Rodman, S., Topl. Masel, 14 (l),61 (1969). Lubric. Eng., 26, 26 (1970). (55C) Prohaska, G., Xafta (Zagreb), 19, (22D) Dunken, H., Winter, H., Boeck, 461 (1968). E., Trzebowski, N., Schmierstoffe (56C) Richterova, V., Ropa Uhlie, 10, Schmierungstech., 1968, 27; C.A., 419 (1969); C.A., 70,21319m (1969). 71, 103776~(1969). (57C) Sadykhov, I. I)., Zeinalov, A. Ya., (23D) Elliott, J. S., Jayne, G. J. J., RIaksimov, S. I., Khim. Tekhnol. Topl. Barber, R. I., J . Inst. Petrol., 55, 271 illasel, 14 ( 5 ) , 59 (1969). (1969). (58C) Sawabe, H., Ohgake, R., Sekiyu (24D) Esposito, G. G., Jamison, R. G., Gakkai Shi, 12, 525 (1969). U.S. Clearinghouse Fed. Sca. Tech. (59C) Schoeller, F., Habel, L., Gas, Inform., AD-694360 (1969). Wasser, Wawme, 23, 8 (1969). (25D) Ewbank, W. J., Waring, R. L., (60C) Zbid., p 29. NLGZ Spokesman, 33, 13 (1969). (61C) Schwartz, F. G., Allbright, C. S., 126D) Faville. F. A,. Faville. W. .~ A.. Ward, C. C., U.S., Bur. Mines, Rep. ‘ Lubric. Eng:, 24, 349 (1968). Invest., 7197, 28 pp. (Dec. 1968). (27D) Fofanov, G. A., Tr. Vses. .Vauch.(62C) Sobolev, E. P., Rubinshtein, I. A., Issled. Inst. Zheleznodorozh. Transp., Smirnov, M. S., Koznov, G. G., Khim. 1968, 210; C.A., 72, 14421m (1970). Tekhnol. T o p l . Masel, 13 (9), 54 (1968). (280) Forbes, E. S., Wood, J. AI., Ind. (63C) Soulages, X. L., ANAL.CHI~M., 39, Eng. Chem., Prod. Res. Develop., 8, 48 1340 (1967). (1969). (64C) Soulnges, X . L., J . Gas. Chro(29D) Francis, H. A., Presland, A. E. B., matogr., 6, 356 (1968). J . Sei. Instrum., 1, 1234 (1968). (6FjC) Spengler, G., Pahl, E., Brennst.(30D) Freund, M., Zatai, A., Pallay, I., Chem., 50, 324 (1969). Szirmai, W., Magy. Asvany. Foldgaz 166C) Suleimanova. F. G.. Bashaev. V. Kiserl. Zntez. Koslem., 10, 191 (1969); E., Khiger, V . ‘ F., Piisadki Smaz, C.A.. 72. 91941h 11970). dfaslam, 1969, 180. (31D) Friberg, S., ‘Rydhag, L., Atterby, (67C) Suleimanova, F. G., Efendiev, 11. P., Tribology, 3, 39 (1970). L., Gabel, K. N., ibid., p 197. (32D) Fujikawa, Y., Asami, K., Junkatsu, (68C) Tao, F. F., Appeldoorn, J. K., 12, 155 (1967); C.A., 69, 60486x ASLE (Amer.Soc. Lubric. Eno.) Trans.. (1968). 11,345 (1968). (33D) Griffin, J. R., S A E (SOC.Auto. (69C) Thouvard, H., Reo. Ass. Fr. Tech. Eng.) Spec. Publ., 350 (1969). Petrole, 1968, 107. (34D) Hall, P. C., Pearson, R., Wash(70C) Uchinuma, K., Nakajima, K., brook, C. C., Lubric. Eng., 24, 262 Tsunemi, LI.,Inoue, K., Sekiyu Gakkai I 1 RBR ). Shi, 12, 940 (1969). (35D) Harris, T. A., J . Lubric. Technol., 91, 294 (1969). Lubricants, Oils, and Greases (36D) Henshaw, J. E., J . Znst. Petrol., 54, 115 (1968). (1D) Abbott, A. D., Farley, L. L., (37D) Hopkins, V., Schroeder, R. J., Lubric. Eng., 24, 422 (1968). Lubric. Eng., 25, 360 (1969). (21)) Adamenko, S. P., Khim. Tekhnol. Topl. Masel, 14 (2), 23 (1969). 138D) Kaealer. S. H.. Morell. G.. Erdoel ‘ Kohle, 22; 399 (1969). i3D) Allum. K. G.. Forbes. E. S..ASLE (Amer. Soc. Lubiic. Eng.) Trans., 1 1 , (39D) Kalaszi, I., Rezek, O., Acta Tech. 162 11968). (Budapest).66, 417 (1969). (4D) Amos,’R., Z . Anal. Chem., 236, 330 (40D) Kempe, J,, Chem. Tech. (Berlin), (1968). 20, 691 (1968). (5D) Armstrong, E. L., Lindeman, >I. A . , 141D) Kichkin. G. I.. Lashkhi. V. L.. Wayne, H. J., NLGI Spokesman, 33, ‘ Zaskal’ko, P. P., Neftepererab. 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ANALYTICAL CHEMISTRY, VOL. 43, NO. 5 , APRIL 1971

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Air Transp. Meet., 1968, Pap. 680322,9 PP. (46D) Lee, W. R., Lewis, L. L., ANAL. CHEM.,42, 103 (1970). (47D) LePera, M. E., U.S. Clearinghouse Fed. Sci. Tech. Inform., AD-663816 (1967). (48D) LePera, M. E., Pigliacampi, J., ibid., AD-697027 (1969). (49D) Leutner, R., Erdoel, Erdgaz Z., 85,527 (1969). (50D) Lieser, J. E., West, C. H., Lubric. Eng., 24, 399 (1968). (51D) Luneva, V. S., Neftepererab. Neftekhim. (Moscow), 1968, 13; C.A., 69, 108345e (1969). (52D) Manoliu, C., Ionita, S., Mihailescu, M., Rev. Chim. (Bucharest), 19, 360 (1968). (53D) Markeeva, L. I., Shestakova, N. M., Nejtepererab. Nejtekhim. (Moscow), 1969, 51; A.P.I.A., 16, 14435 (1969). (fi4D) Marvillet. J.. DuParauet. J.. NLGI

(1968). (58D) hfikheev, V. A,, Klimov, K. I., Nejtepererab. Neftekhim. (Moscow), 1969, 16; C.A., 70, 107999e (1969). (59D) blikheev, V. A,, Semenov, K. A., Chernikova, T. P., Khim. Tekhnol. Topl. Masel, 14 (lo), 44 (1969). (60D) Ibid., (12), 49 (1969). (61D) Motor Veh. Fuel. Lubric., and Equip. Res. Comm. of the Coord. Res. Coun., Inc., Coord. Res. Coun. Rep., . . 426, 30 pp (1969). (02D) Murph C. hl., SAE (SOC.Auto. Eng.) Air '&ramp. Meet., 1968, Pap. 680320,9 pp. (63D) Nambu, M., Yukagaku, 18, 2 (1969); C.A., 70, 89349m (1969). (64D) Perin, Yu. I., Sedykin, F. V., Zavod. Lab., 35. -53 (1969): C.A.,, 70.. . ,, 79702g (1969). ' (65D) Pie Contiioch. 0.. Cortes Rubio. ' A.,'Rev. Inst. Gez. Petrol., 1, 90 (1969): (66D) Pliev, T. N., Glavati, 0. L., Popovich, T. D., Vysokomol. Soedin., 12, 31 (1970); C.A., 72, 91934hj1970). (67D) Przvbvlski, Z., Kotowski, M., Chem. A-nil. (Warsaw), 14, 643 (1969); (68D) Przybylski, Z., Lichowska, K., Nafta (Katowzce),24, 45 (1968). (69D) Quigley, D. A., Davies, D. G., Evans, H. L., Lab. Pract., 18, 421 (1969). (70D) Reynolds, H. W., Jr., SAE (Soc. Auto. Eng.) Air Transp. Meet., 1968, Pap. 680321, 6 pp. (71D) Rozenberz. Y. A,. Kodin. A. A.. ' Karamnova, P., Khim. Tekhnol: Topl. Masel, 15 ( l ) , 52 (1970). (72D) Sato, Rf., Kagaku Keisatsu Kenkyusho Hokoku, 20, 180 (1967). . . (73D) Ibid., 22, 4,5 (i969). (74D) Schermann, W., Energie, 21, 202 (1969). (75D) Shields, S. E., Herring, W. M., Bourne, E. J., S A E (SOC.Auto. Eng.) Spec. Publ., 350 (1969). (76D) Shimizu, I., Yukagaku, 18, 36 (1969); C.A., 70. 69849w (1969). (77D) Simon, F., i c t a Chi;. (Bidapest), 59,57 (1969). (78D) Slobodin, Ya. M., Malysheva, T. G., Khim. Tekhnol. Topl. Masel, 13 (4), 55 (1968). (79D) Smith, E. A., Ind. Lubric., 19, 332 (1967). (80D)'Stavinoha, L. L., Wright, B. R., SAE (SOC.Auto. Eng.) Combined Fuels and Lubric. and Transp. Meet., 1969, Pap. 690776, 19 pp.

v.

(81D) Stoll, P., Vuillemier, C., Elektrotech. Z., 90, 176 (1969). (82D) Strong, S. B., NLGI Spokesman, 32,426 (1969). (83D) Suleimanova, F. G., Gurylev, G. G., Liksha, V. B., Suleimanova, L. G., Abdullaev, B. I., Abdullaev, A. M., Azerb. Neft. Khoz., 47, 42 (1968); C.A., 69, 37618h (1968). (84D) Texaco, Inc., Lubrication, 54, 97 (1968). (85D) Ibid., 55, 77 (1969). (86D) Thoenes, H. W., Bauer, K., Erdoel Kohle, 21, 543 (1968). (87D) Tooke, P. B., Wilde, A. J., J . Inst. Petrol., 55, 343 (1969). (88D) Turnquest, B. W., Culliney, P. G., SAE (SOC.Auto. Eng.) Combined Fuels and Lubric. and Transp. Meet., 1969, Pap. 690775, 6 pp. (89D) Uchinuma, K., Toida, F., et a/., Sekiyu Gakkaz Shz, 12, 627 (1969). (901)) Uchinuma, K., Toida, F., Kinomiya, S., ibid., p 632. (91D) Vajta, L., Adonyi, Z., Vajta, S., Acta Chim. (Budapest), 58, 207 (1968). (92D) Vesely, V., Ropa Uhlie, 11, 297 (1969); C.A., 72 4895e (1970). (93D) Vipper, A. B., Tarasov, V. A., Neftepererab. h'eftekhim. (Moscow), 1969 23; C . A . , 72, 23141x (1970). (94D) Walker, F. I)., Mater. Res. Stand., 9 (2), 28 (1969). (95D) Webster, P. V., Wilson, J. N., Franks, &I. C., J . Inst. Petrol., 56, 50 (1970). (96D) Winney, P. E., J . Sci. Instrum., 1, 767 (1968). (97D) Wisken, A., Weinbeber, W.,Honsch, G., British Patent 1,138,708, Jan. 1, 1969. (98D) Wislicki, B., Karpinski, W., Schmierstoffe Schmierungstech., 1968, 80; C . A . , 71, 9 3 2 6 0 ~ ;(1969). wax

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(20E) Rakos, hl., Collect. Czech. ?hem. Commun.. 34.3136 119691. (21E) Reutner,' F., 'Fette,' Seifen, Anstrichm., 70, 162 (1968). (22E) Sojak, L.. Bucinska. A.. RoDa Uhlie. io, 572-(1968j; ~ . ~ . ~ . , ' 1 8 , ' 1 7 (1970): 5'9 (23E) Streibl, AI., Stransky, K., Fette, Seifen, Anstrichm., 70,543 (1968). (24E) Szergenyi, I., Period. Polytech., 13, 61 (1969); C . A . , 72, 14431q (1970). Asphalt

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(lG).Barbul, R l . , Zirna, I., Ghejan, I., Baicoianu, L., Petrol. Gaze (Bucharest), 19,99 (1967); C.A., 69 108303q (1968). (2G) Beruto, D., Ferraiolo, G., Reverbert, A., Ann. Chim. (Rome), 58, 931 (1968). (3G) Bjorklund, I. S., Dygert, J. C., AICHE (Amer. Inst. Chem. Eng.) J . , 14,553 (1968). (4G) Cotiga, &I., Rev. Chim. (Bucharest), 19.615 (1968). (3G)' Crawley, D. F. C., J . Sci. Instrum., 1,576 (1968). (6G) Danforth, J. D., U.S. Patent 3,431,077, Nar. 4, 1969. (7G) Fortina, L., hlaggiore, R., Toscano, G., ilnn. Chim. (Rome), 59, 121 (1969). (8G) Goldstein, RI. S., RIorgan, T. R., J . Catal., 16, 232 (1970). (9G) Haftka, F. J., Z. Anal. Chem., 231, 321 (1967). (10G) Henderson, D. S.,Ciapetta, F. G., Amer. Chem. SOC.,Diu. Petrol. Chem.. Prepr., 12, 83 (1967). ( l l G i Hillar. S. A.. Mannoris. .I. - - C.. -. Peiera, J. ' RI., R&. Fac. Ing. Quim.: Univ. Xac. Litoral., 36, 153 (1967). (12G) Joly, J. P., Vaillant, D., Ponsolle, L., Bull. SOC.Chim.Fr., 1967, 3181. (13G) Kiezel. L.. Rutkowski. Mi.. Tomasik, Z., Chem. Stosow., Ser: A , 121 407 (1968); C.A., 70, 594472 (1969). (14G) Ksenzhek, 0. S., Kalinovskii, E. A., Zh. Fiz. Khim., 41, 1602 (1967). (15G) Leppard, C. J., Spencer, D. H. T., J . Sci. Instrum., 1, 573 (1968). (16G) Rlacek, J., blalecha, J., AXAL. CHEM.,41, 442 (1969). (17G) Rlanoliu, C., Plisculescu, M., Tomi, B., Rev. Chim. (Bucharest), 19, 416 (1968). ~~. ._, (18G) Marsh, W. W., Xyers, G., Anal. Cham. Acta, 43, 511 (1968). (19G) Matano, N., Ono, K., Fiyii, T., Jap. Anal., 17, 560 (1968). (20G) Medema, J., Houtman, J. P., R., ANAL.CHEM.,41, 208 (1969). (21G) RIeffert, A., Langenfeld, A., Z . ilnal. Chem., 238, 187 (1968). (22G) hlishchenko, A. P., Rodicheva, R l . F., Zh. Anal. Khim., 22, 1536 (1967). (23G) Palazov, A., Shopov, D., Izv. Otd. Kham. Saukz, Bulg., Akad. iYauk, 1, 175 (1968). (24G) Pickler, H., Kater, E., Brennst.Chem., 50, 373 (1969). (25G) Popescu, S., Papagheorge, &I., Rev. Chzm. (Bucharest), 19, 737 (1968). (26G) Rayburn, K. A., Appl. Spectrosc., 22,726 (1968). (27G) Rees, T. D., Hill, S. R., Talanta, 15,1312 (1968). (28G) Serbanescu, A., Fedin, T., Petrol. Gaze (Bucharest), 20, 47 (1969); C.A., 70, 1168263. (1969). (29G) Shmulyakovskii, Ya. E., Anisimova, A. A,, Kznet. Katal., 10, 881 (1969). ~o------,

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(30G) Sieh, R. H. W., Staub, Reinhalt. Lujt, 28, 480 (1968). (31G) Spencer, D. H. T., Fereday, F., Chem. Ind. (London),1968,847. (32G) Strel'nikova, Zh. V., Emel'yanova, G. I., Lebedev, V. P., Zh. Fiz. Khim., 41.2299 (1967). (33G') Svajgl, O:, Chem. Prum., 19, 404 (1969); C..4., 71, 103758~(1969). (34G) Urbain, H., Bacaud, R., Charcosset, H., Tournayan, L., Chim. Anal. (Paris),50, 242 (1968). (33G) Vajta, L., Mandy, T., Moser, M., Schay, Z., Szebenyi, I., Period. Polytech., 13, 19 (1969); C . A . , 72, 23106q (1970). (36G) Ward, J. W., Hansford, R. C., J . Catal., 13, 154 (1969). (37G) Winter, D. G., Chem. Ind. (London), 1969, 233; B.A.A., 18, 3654 (1970). Physical Properties

(1H) Abas-Zade, A. K., Kuliev, R. Sh,, Kevarkova, I. S., Zakirov, R., Anisimova, A. M., Dokl. A4kad. Yauk Tadzh. SSR, 12 (3), 22 (1969). (2H) Affens, W. A., McLaren, G. W., Amer. Chem. SOC.,Diu. Petrol. Chem., Prepr., 14, 4.5 (1969). (3H) Auckland, &I.H. T., Charnock, D. J., J . Inst. Petrol., 55 322 (1969). (4H) Barnett, J. D., Bosco, C. D., J . A p p l . Phys., 40, 3144 (1969). (5H) Becker, F., Chem.-Ing.-Tech., 40, 933 (1968). (6H) Belousov, V. P., Ponner, V., Zh. Ftz. Khzm., 42, 2124 (1968). (7H) Cheng, D. C. H., Chem. Eng. Sca., 23, S9;i (1968). (8H) Chulkov, P. V., Khim. Tekhnol. Topl. Masel, 13 (l),59 (1968). (9H) Coord. Res. Coun. Rep., 414, 13 pp (1968). (10H) Zbzd., 409, 66 pp (1968). (11H) Costa, 11. P., Lubric. Eng., 23, 39.5 (1967). (12H) Dubovkin, N. F., Malanicheva, V. G., Kuznetsova, &I. N., Kham. Tekhnol. Topl. Masel, 14 (12), 55 (1969). (13H) Eggertsen, F. T., Seibert, E. E., Stross, F. H., ANAL.CHEM.,41, 1175 11969) \ - I _ _

(14H) Gabibov, A. B., Tsaturyants, A. B., Dokl. Akad iVauk Azerb., 24, 19 (1968). (1SH) Galimberti, M., Campbell, J. M., Oil Gas J.. 67 1441. 64 (1969). (16H) Ganiev, Yu. 'A.,Grigor'ev, B. A., Izv. Vussh. L'cheb., Zaved., Sejt Gaz, 11, 14 (1968). (17H) Geller, V. Z., Khim. Tekhnol. Topl. '$fusel, 14 (9), 33 (1969). (18H) Geller, V. Z., Rastorguev, Yu. L., Zzv. Vussh. Ucheb. Zaved.. Neft. Gaz., 11., 60 Cl9881. (19H) Gonzalez, &I. H., Lee, A. L., J . Chem. Eng. Data, 13, 172 (1968). (20H) Gonzalez, AI. H., Subramaniam, T. K., Kao, R. L., Lee, A. L., Proc. 1 s t Znt. Conf. L S G (Lzauefied Satur. Gas). Pap., 5121, 38 pp (ig68). (21H) Hankinson, It. W., Thomas, L. K., Phillips, K. A., Hydrocarbon Process., 48, (4), 106 (1969). (22H) Hoffman, E. J., J . Mater., 4, ( l ) , I

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28 (~ 1 R-6-F -) \ " , .

(23H) Ibid., 5 (l),37 (1970). (24H) Jensen, R. H., Kurata, F., J . Petrol. Technol., 21, 683 (1969). (25H) Jentoft, R. E., Carlstrom, A. A., Gouw. T. H.. ANAL.CHEM..40. 1014 (ig68j. (26H) Johnson, D. W.,Colver, C. P., Hydrocarbon Process., 48 (3), 113 (1969). (27H) Klosek, J., McKinley, C., Proc. 1st Int. Conf. LLVG (Liquefied Natur. Gas), Pap., 5/22, 15 p (1968). Panova, E. S., (28H) Kollerov, D. Tr. Metrol. Inst. SSSR, 1968, 123. ,

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(29H) Korol'chenko, A. Ya., Bobkov, A. S., Zhuravlev, V. S., Lantukhova, L. V., Khim. Tekhnol. Topl. Masel, 14 (8), 16 (1969). (30H) Kurtz, S. S.,Jr., Amer. Chem. SOC.,Dav. Petrol. Chem., Prepr., 13, 139 (19681.

(33H) glanovyan, A. K., Tr. Grozn. Nejt. Nauch.-Issled. Inst., 1968 (22), 96. (34H) Ibid., p 108. (35H) Manovyan, A. K., Khachaturova, D. A., ibid., p 119. (36H) Manovyan, A. K., Odintsov, 0. K., ibid., (24), 21. (37H) Manovyan, A. K., Khachaturova, D. A., Khim. Tekhnol. Topl. Masel, 15 (l),23 (1970). (38H) McDuffie, G. E., Barr, T., Rev. Sci. Instrum., 40,653 (1969). (39H) Morawetz, E., Acta Chem. Scand., 22,1509 (1968). (40H) Naziev, Ya. N., Abasov, A. A., Izv. Vyssh. Ucheb. Zaved., Nejt Gaz, 11, 65 (1968). (41H) Nelson, W. L., Oil Gas J., 67 (47), 111 (1969). (42H) O'Donnell, R. J., Mater. Res. Stand., 9 (5), 25 (1969). (43H) Pecsok, It. L., Windsor, M. L., ANAL.CHEM.,40, 1238 (1968). (44H) Plundo, R. A., Strom, J. R., Hydrocarbon Process., 48 (ll),270 (1969). (45H) Popescu, R., Blidisel, I., Grigoriu, D., Petrol. Gaze, 19, 167 (1967). (46H) Prikryl, R., Miglieriniova, K., Holotik, S., Ropa Uhlie, 11, 238 (1969); C.A., 71, 32004m (1969). (47H) Iteches, F., Unav. Cincinnati, Diss., (1967). (48H) Rein, R. G., Jr., Sliepcevich, C. M., J . A p p l . Phys., 40, 131 (1969). (49H) Rieger, F., Chem. Eng. Sci., 25, 219 (1970). (5OH) Sastri, S. R. S., Gokhale, M. V., Chem. Process Eng. (London), 50, 77 (1969). (5lH) Schuringa, A., J . Sci. Instrum., Ser. 2, 2, 1093 (1969). (52H) Shitikov, L. I., Nejteprom. Delo, Nauch.-Tekh. Sb., 1968, 26. (53H) Smirnov, A. S., Nejt. Khoz., 47 (4), 60 (1969). (54H) Synder, H. A., Rev. Sci. Instrum., 40,992 (1969). (55H) Stanley, E. hl., Batten, R. C., ANAL.CHEM.,40, 1751 (1968). (56H) Stech, W., Schmiertecknik, 16, 157 (1969). (57H) Thomas, L. H., Smith, H., Meatyard, R., J . Sca. Instrum., Ser. I,1, (58H) 1119Varushchenko, (1968). R. hl., Gal'chenko, G. L., Skuratov, S.hl., Zh. Fiz. Khim., 44,283 (1970). (59H) White, M. S., Solomons, C., Rev. Sci. Instrum., 40, 339 (1969). (60H) Wichterle, I., Boublikova, L., Znd. Eng. Chem., Fundam., 8,585 (1969). (61H) Wright, W. A., J. Mater., 4 ( l ) , 19 (19691. (62Hj Zanker, A., Brit. Chem. Eng., 14, 359 (1969). Hydrocorbons

(11) Arakelyan, V. G., Sarycheva, L. S., Evdakov. V. P.. Zh. Anal. Khim... 23,. 109 (1968). (21) Araki, S., Hobo, T., Bunseki Kagaku, 1968, 148; C..4., 69, 32837u (1968). (31) Archer, E. D., Lubrication, 55, 13 (1969). (41) -Arich, G., Volpe, S., J . Gas Chromatogr., 6, 384 (1968).

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(431) Dikun, P. P., Krasnitskaya, N. D., Gorelova, N. D., Kalinina, I. A., Zh. Prikl. Xpektrosk., 8, 406 (1968); C.A. 69, 64470k (1968). (441) Dimov, N., Shopov, D., J . Chromatogr., 44, 170 (1969). (451) Dunning, R. W., Leonard, J. A,, Chromatographia, 1969, 293. (461) Eisenbrand, J., Becker, G., Z . Anal. Chem., 242,145 (1968). (471) Fant'er, D. L., Walker, J. Q., Wolf, C. J. ANAL.CHEM.,40, 2168 (1968). (481) gauvet, J . E., Pazdzerski, A,, Blouri, B., Bull. SOC.Chim. Fr., 1967, 4732. (491) Fedoseeva, G. E., Khesina, A. Y., Zh. Prikl. Spektrosk., 9, 282 (1968); B.A.A., 17, 3554 (1968). (501) Ferhat, blaman, Valdener, Method Phys. Anal., 5,379 (1969). (511) Fett,, E. it., Christoffersen, D. J., Snyder, L. R., J . Gas Chromatogr., 6, 572 (1968). (521) Fitzgerald, M. E., PIIoirano, J. L., Morgan, H., Cirillo, V. A., Appl. Spectrosc., 24, 106 (1970). (531) Fleet, B., Jee, It. D., Talanta, 16, 1561 (1969). (541) Fleet', B., Keliher, P. N., Kirkbright, G. F., Pickford, C. J., Analyst (London),94,847 (1969). (551) Fleet, B., Kirkbright, G. F., Pickrord, C. J., Talanta, 15,566 (1968). (561) Forsey, R. R., J . Gas Chromatogr., 6,555 (1968). (571) Franc, J., Senkyrova, J., Mikes, F., Placek, K., J . Chromatogr 43, 1 (1969). (581) Fritz, J. S., Wood, 6. E., ANAL. CHEM.,40, 134 (1968). (591) Fuhrmann, R., Jeralomon, D., J . Chromatogr., 22, 468 (1966). (601) Gallegos, E. J., J . Phys. Chem., 72, 3452 (1968). (611) Geiss, F., Versino, B., Schlitt, H. Chromatographia, 1968, 9. (621) Ghosh, S. K., Saha, N. C., Technology, 5, 220 (1968). (631) Gilyazetdinov, L. P.,Khim. Tekhno(. Topl. Masel, 13 (6), 57 (1968). (641) Coma, G., Method Phys. Anal., 5, 239 (1969). (651) Gough, T. A,, Walker, E. A., J . Chromatogr.Sci., 8, 134 (1970). (661) Groenendijk, H., van Kemenade, A. W. C., Chromatographia, 1, 472 (1968). (671) Guillemin, C. L., Auricourt, RI. F., J . Chromatogr. Sci., 7, 493 (1969). (681) Guillot, J., Bottazzi, H., Guyot. A., Trambouze, Y ., J . Gas Chromatogr., 6, 605 (1968). (691) Gul'ko, G. I., Azerb. Neft. Khoz., 4 , 44 (1968); B.A.A., 17, 1466 (1969). (701) Gul'ko, G. I., Vyakhirev, D. A., Aliev, hl. I., Kozeiko, T. A., Neftepererab. Neftekhim. (Moscow), 1969, 29; C.A., 71,56482s (1969). (711) Gump, B., J . Chromatogr. Sci., 7, 755 (1969). (721) Hachenberg, H., Gutberlet,, J., Brennst.-Chem., 49, 279 (1968). (731) Halasz, I., Sebestian, I., ilngezo. Chem., Int. Ed. Engl., 8, 433 (1969). (741) Hammerstrand, K., Juntunen, J. SI.,Hennes, A. R., Anal. Biochem., 27, 172 (1969). (751) Hendrickson, J. G., J . Chromatogr., 32,543 (1968). (761) Herrin, C. B., J . Gas Chromatogr., 6,470 (1968). (771) Hively, R. A., Hinton, R. E., ibid., p 203. (781) Hofman, J., Tomanek, O., Vodicka, L., Landa, S., Collect. Czech. Chem. Commun., 33,2276 (1968). (791) Zbid., 34, 1042 (1969). (801) Ivanov, A., Eisen, O., Eesti NSV Tead. Akad. Toim., Keem. Geol., 18, 296 (1969).

(811) Ivanova, M. D., Sidorov, R. I., Petrova, V. I., Gazov. Khromatogr., 1968 ( 8 ) ,35. (821) Jaeger, J., Atmos. Environ., 2, 293 (1968). (831)Jentoft, It. E., GOUW,T. H., ANAL. CHEM.,40, 923 (1968). (841) Ibid., 1787. (851) JentoK, it. E., GOUW, T. H., J . Chromatogr. Sci., 8, 138 (1970). (861) Joly, D., 2. Anal. Chem., 236, 259 i1968). (871) Kajdas, C., Erdoel Kohle, 22, 459 (1969). (881) Kajdas, C., Tuemmler, R., Chem.Tech. Ind., 65, 2j9 (1969). (891) Kaiikawa. AI.. Amari. T. Fllknshima,"C., Bunseiz Kagadu, k, 1245 (1969); C . A . , 72, 3395la (1970). (901) Kantor, &I.,Magy. Asvany, Foldgaz Kiserl. Zntez. Kozlem., 9, 23 (1968); C.A.. 71. 35771v (19691. (911) Kendall, R. F., Spectrochim. ilcta, A , 24, 1839 (1968). (921) Kerr, G. P. S., ANAL. - .-T., - -Landis, .- CHEM.,40, 1176 [lY68). (931) Kessler, T., Sharkey, A. G., Hickam, W. M.,Sweeney, G. G., Appl. Spectrosc., 21. X 1 11967). , (94Ij Kioussis, D., Chem. Chron., Epistem. Ekdosis, 34, 6 (1969). (951) Kiselev, A. V., Migunova, I. A., Savinov, I. M., Yabhin, Y. I., Neftekhimiya, 8, 643 (1968). (!361) Klesment, I., J . Chromatogr., 31, 28 (1967). (!371) Kol'kovski. P., 2. Anal. Khim.. 22. 456 (1967). (981) Konyashina, R. A., Lozovai, A. V., Malkova, S. S., Nikiforova, T. S., Neftepererab. lVeftekhim. (Moscow), 1968, 4; C . A . , 69, 885544 (1QfiX) - - --,' (991) Krakow,. B.,, ANAL.CHEM.. , 41.. 815 (1969). (1001) Kramer, K., Erdoel Kohle, 22, 270 ( 1969). (1011) Krasaychenko, M. I., AIikhnovskaya, A. A., Morozova, 0. E., Petrov, -4.A., iYeftekhimiya, 8, 663 (1968). (1021) Ibid., 9, 651 (1969). (1031) Kuklinskii, A. A., Simonov, .4.A., Filippov, V. P., Pushkina, R. A., Zimina, K. I., Khim. Tekhnol. Topl. itfuse/., 13 (lo), 15 (1968). (1041) Zbid., (8), 32 (1968). (1051) Zbid., ( 3 ) , 53 (1968). (1061) Kvitkovskii, L. N., Balinskii, I. S., ibid., 14 (7), 53 (1969). (1071) Landault, C., Guiochon, G., Chromatographia, 1968, 119. (1081) Langner, E. H., S.i l f r . J . Agr. Sci., 11, 187 (1968). (1091) Lavalette, D., Nuel, B., HubertHabart, AX., Ilene, L., Lat'arjet, R., J . Chim. Phys., 65,2144 (1968). (1101) Liberman, A. L., Furman, D. B., Neftekhimiya, 8, 811 (1968). (1111) Zbid., 9, 803 (1969). (1121) Liberti, A., Nota, G., Goretti, G., J . Chromatogr., 38, 282 (1968). (1131) Libickova, V., Stuchlik, hl., Krasnec, L., ibid., 45, 278 (1969). (1141) Lindeman, L. P., Amer. Chem. SOC., Diu. Petrol. Chem., Prepr., 14, B186 (1969). (1151) Lipatova, L. F., Bednov, V. &I., Koks Khim., 1968,47. (1161) Locke, D. E., J . Chromatogr., 35, 24 119681. (117Ij Lowenguth, J. C., Tourres, D. A., Z . Anal. Chem., 236, 170 (1968). (1181) Lumpkin, H. E., 7th World Petrol. Congr. Proc., 1967, 9. 23. (119Ij SIcCarthy, E. D., Han, J., Calvin, M.,ABAL.CHEM.,40, 1475 (1968). (1201) Macke, G. F., J . Chromatogr., 36, 537 11968). ( 1 2 l I ) ' ~ c K i n n e y R. , W., Jordan, R. L., J . Gas Chromatogr., 5, 501 (1967). ~

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201 R

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(44M) Marletta, G. P., Gabrielli, L. F., Tec. Jtal., 34,307 (1969). (45M) Marten. J. F.. Ind. Chim. Belae. 32.. 1319 (1967). (46M) Matthews, P. J., J. A p p l . Chem. (London), 20, 87 (1970). (47M) Mattson, J. S., Mark, H. B., Jr., Kolpack, R. L., Schutt, C. E., ANAL. CHEM.,42, 234 (1970). (48M) Otcasek, It. A., S A E (SOC.Auto. Eng.) Spec. Publ., 350, (1969). (49M) Ramsdale, S. J., Wilkinson, R. E., J. Inst. Petrol., 54, 315 (1968). (50M) Raymond, A. J., Lawrey, I). M. G., Mayer, T. J., J . Chromutogr. Sci., 8 , l(1970). (5lM) Saltzman, R. S., Anal. Instrumen., 6,79 (1968). (52hI) Scaringelli, F. P., Rehme, K. A,, ANAL.CHEM.,41,707 (1969). (.53M) Schneider, W., Chem. Tech. (Berlin),20, 299 (1968). (54M) Sher, J. A., Oil Gas J . , 66 (36), 93 119681. (55hI) Sono, K., Iwashige, H., Kyushin, S., Kogyo Kagaku Zasshi, 72, 801 (1969). I

,

\ - - - - , -

(56M) SOOS, K., Cieleszky, V., K o ~ . Ert., 11, 100 (1969). (57M) Steger, E., Kahl, H., Chem. Tech. (Berlin),21, 483 (1969). (58M) Sugar, J. W., Conwa , R. A,, J . Water Pollut. Contr. F e z 40, 1622 (19681. \---_,

(.59M) Taras, M. J., Blum, K. A,, ibid., p R405. (60M) Templeman, G. C., ASTM (Amer. Soc. Test. Mater.) Comm. D-2 Symp., New Orleans, 1968, Preprint, 32 pp. (6lM) Tunnicliff, D. D., Wadsworth, P. A., ANAL.CHEM.,40, 1826 (1968). (62M) Vasil’eva, V. V., Nikolaeva, N. G., Ivanova, T. S., Nejtepererab. Neftekhim. (Moscow), 1969, 52; A.P.I.A., 16, 14438 (1969). (63M) Weihman, K. F., Davis, E. N., Wertzler, R., Nat. Petrol. Refiners Ass. Computer Conf., Phila., 1968, Pap. CC68-94,21 pp. (64M) Wernimont, G., ASTM (Amer. SOC.Test. Mater.) Comm. D-2 Symp., New Orleans, 1968, Preprint, 64 pp. (65M) Yoshii, T., Katsuda, K., Ueda, K., Kogyo Yosui, 1967, 72.

Pharmaceuticals and Related Drugs 1. W. Sutherland,

D. E.

Williamson, and I. G. Theivagt,

Analytical Research Department, Abbott laboratories, North Chicago, 111.

T

HIS SURVEY INCLUDES analytical methods and related topics of pharmaceutical interest that have appeared since the last published review (1500), or were not included in the previous reviews, and covers t h e literature to June 1970. The same tabular format is retained from the last review. References to the analysis of pharmaceuticals in biological media are denoted b y a superscript B. Such references are restricted to the determination of administered drugs and metabolites. Numerous reviews of interest to analytical chemists working in the drug field have appeared. Automated techniques in pharmaceutical analysis were presented, including both continuous flow and discontinuous analysis (1136). I n the fundamental analytical reviews on chromatography (2549), ion exchange (1150), and electrophoresis (1985), applications of the respective techniques to pharmaceuticals were discussed. Pertsev (1568) has presented a general review of thin-layer chromatography and its use in pharmaceutical analysis. Many references to drugs are found in Haywood’s (805) and Stahl’s (1948) books on thin-layer chromatography. Several applications of chromatography to drugs are described in books by Smith (1924) and blarinetti (1258). Still presented in the Journal of Chromatography are the bibliography and chromatographic sec-

206 R

0

tions which frequently list current applications of the various chromatographic techniques to pharmaceuticals. Comprehensive reviews have appeared on gas chromatography in pharmaceutical analysis (1127, 1329). Kroman and Bender, in their book “Theory and Application of Gas Chromatography in Industry and Medicine,” discuss applications in drug research, toxicology, drug metabolism, and new drugs (1113). The increasing use of derivatization for previously nonchromatographable compounds is exemplified by Sennello’s application to vitamins (1839). Reviews on nonaqueous titrimetry applied to drug analysis have appeared (651, lS43). The applications of spectrophotometric titrations (1884) and high-frequency titrations (1711) to pharmaceuticals have also been reviewed. Recent developments in the field of ultraviolet spectrometry have been reviewed, including applications to pharmaceutical analysis (404). Photometry in the analysis of drugs was reviewed b y Yaskina and Lirova (2311). I n Bouche’s review of infrared spectrophotometry in drug analysis (248), he discussed the place of infrared spectrophotometry in pharmacopeias and other official texts on pharmaceuticals. The fluorometric analysis of vitamins, steroids, hormones, and other pharmaceuticals was reported in the review by White


and Weissler (8258). An introduction to fluorometry with applications for determining pharmaceuticals was described by Xirau-Vayreda (2278). The spectroscopy of amines of pharmaceutical interest was reviewed by Eisdorfer, Warren, and Zarembo (509). Both the qualitative and quantitative aspects of the various techniques, UV, I R , NMR, Raman and mass, were described. The applications of modern electroanalytical techniques to pharmaceutical chemistry was covered by Adams ( 5 ) . Discussed were the fundamentals of voltametry, comparison of potentiometry and voltammetry, response characteristics of electrodes, and potentialities and shortcomings of electroanalytical techniques. General articles, discussing the present status and progress of pharmaceutical analysis, are presented in a number of papers (548, 1006, 1007, 1589, 1590, 1591, 1593, 1595, 1840, 2106). Schmitt and Mathis have provided a survey on the analytical methods for antibiotics reported during the last ten years (1815). The identification of drugs has received attention with the recent publications by Clarke (367),Fulton (618),and Sunshine (8002). Even though written for the toxicologist, all three books have a wealth of information useful to those concerned with drug identification and analysis in general.

Petroleum. Miscellaneous - Analytical Chemistry (ACS Publications)

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