Wayne M. Stalick

Synthesis of Novel Functionalized N -Tosylaldimines

Abstract Condensation of a variety of aromatic aldehydes with p-toluenesulfonamide in the presence of Lewis acids affords novel functionally varied aromatic N-tosylaldimines in good yields. A diverse array of aromatic aldehydes was examined, each containing a unique functionality. The new method reported here allows for incorporation of functionalities that are unavailable by existing methods.

Biofuel: An alternative to fossil fuel for alleviating world energy and economic crises

The time has come when it is desirable to look for alternative energy resources to confront the global energy crisis. Consideration of the increasing environmental problems and the possible crisis of fossil fuel availability at record high prices dictate that some changes will need to occur sooner rather than later. The recent oil spill in the Gulf of Mexico is just another example of the environmental threats that fossil fuels pose. This paper is an attempt to explore various bio-resources such as corn, barley, oat, rice, wheat, sorghum, sugar, safflower, and coniferous and non-coniferous species for the production of biofuels (ethanol and biodiesel). In order to assess the potential production of biofuel, in this paper, countries are organized into three groups based on: (a) geographic areas; (b) economic development; and(c) lending types, as classified by the World Bank. First, the total fossil fuel energy consumption and supply and possible carbon emission from burning fossil fuel is projected for these three groups of countries. Second, the possibility of production of biofuel from grains and vegetative product is projected. Third, a comparison of fossil fuel and biofuel is done to examine energy sustainability issues.

THE SYNTHESIS OF ACETALS AND KETALS OF THE REDUCED SUGAR MANNOSE AS FUEL SYSTEM ICING INHIBITORS.

ABSTRACT The current fuel system icing inhibitor additives used in both the military and commercial airlines are ethylene glycol monomethyl ether (EGME) and diethylene glycol monomethyl ether (DiEGME)These deicing compounds are toxic at the concentrations that are required for effective deicing. When fuel system sumps, filters and storage tanks are drained, they contain EGME/DiEGME and create a personnel hazard. Acetals and ketals of reduced sugars represent viable alternatives to glycol based additives. They are inexpensive, fuel stable for at least one year and show similar icing inhibitor characteristics. This paper summarizes the synthesis and fuel studies for these compounds.

FUEL INSTABILITY STUDIES: THE SYNTHESIS OF LONG CHAIN ALKYL SUBSTITUTED INDOLES

ABSTRACT The reactions that are responsible for fuel instability are complex and not well understood. GC/MS analysis of many different middle distillate and fuel oils showed that substituted indoles were always present in both the fuel itself and in the sediments formed by these fuels. The alkyl chain length of substitution of indoles found in fuels varies with distillation range. Indoles found in the middle distillate fraction have an average alkyl chain length of one to eight carbons while in fuel oils, the alkyl side chain can be up to twelve or fourteen carbons in length. Commercially, only short chain alkyl substituted indoles are available. This paper presents our results for the synthesis of long alkyl chain substituted indoles to be used for instability studies.

Computational study of the environmental fate of selected aircraft fuel system deicing compounds

The current fuel system icing inhibitor (FSII) additives used for commercial and military aircraft are ethylene glycol mono methyl ether (EGME) and diethylene glycol mono methyl ether (DiEGME). Propylene glycol is used for wing deicing. Fuel deicing additives are required in military fuels an optional in commercial fuels with wing deicing being weather dependent. The acetals and ketals of reduced sugars are being synthesized and modeled computationally because they are less toxic and more environmentally benign than EGME and DiEGME. Each compound is being studied with an emphasis on deicing effectiveness, human toxicity, and environmental hazard. This paper reports on three compounds derived from the sugar mannose.

Fuel instability studies : The reaction of 3-methyl indole with aryl sulfonic acids

ABSTRACT Incompatibility reactions in middle distillate fuels can be ascribed to the presence of specific polar heteroatomic compounds or species containing oxygen, sulfur, and nitrogen. It has been proposed that the observed sediment and/or gum formation results from the interaction of heteroatomic species with the acids contained in fuels. Recent studies have shown that the addition of non-basic nitrogen heterocycles such as indoles to a fuel increases deposit formation dramatically. Therefore, an attempt was made to identify the structure of the sediment. This paper reports on the reaction of 3-methyl indole with aryl sulfonic acids. The results of this study were accomplished by identifying the nature and the structure of the sediments formed using elemental analysis and various instrumental techniques.

Fuel system icing inhibitors : The synthesis of esters of oxaacids

ABSTRACT Currently ethylene glycol mono methyl ether (EGME) and diethylene glycol mono methyl ether (DiEGME) are used as fuel system icing inhibitor additives in both military and commercial aircraft. These compounds are toxic at the concentrations that required for effective deicing When fuel systems sumps, filters and storage tanks are drained, they contain EGME/DiEGME and create hazards for personnel. Ethyl esters synthesized from oxaacids have been identified as possible fuel system icing inhibitor additive replacements. These compounds were synthesized from oxaacids and ethanol by an acid catalyzed Fischer esterfication method The products were identified by infrared spectrometry, nuclear magnetic resonance spectrometry, and elemental analysis Physical characterization included boiling point determination and refractive index. The tested oxaesters were found to be fuel stable for at least two years by accelerated storage tests. Octanol-water partition coefficients were determined and indicate the com...

ELECTROCHEMICAL STUDIES OF QUINONE OXYGEN

Asphaltenes are a chemically complex mixture of aromatic and heteroaromatic compounds. This material contains oxygen in various functional groups. The distribution includes esters, carboxylic acids, phenolic and most probably quinone type oxygen functionalities. The present work details the complete electrochemical behaviour of quinone type oxygen. The method is quinone specific. A condensed aromatic quinone, 9,10-anthraquinone, was selected as representative of complex quinones. By this method quinones can be determined in the presence of other oxygen functional groups, alcohols, carboxylic acids, ethers, and other carbonyls.

Pyrolysis of tetralin at 450°C

Abstract Tetralin was pyrolyzed at a temperature and pressure regimen similar to the petroleum refining process known as delayed coking. Conditions employed were: temperature 450°C, pressure 600 kPa and reaction times of 60 to 300 min. The product composition was analyzed by combined capillary column gas chromatography-mass spectrometry. For all reaction time periods, naphthalene was the major product observed. Other significant products included: 1,2-dihydronaphthalene, 1-methylindan, n -butylbenzene and a tetralin-1-methylindan adduct. Minor products included: indene, decalin,toluene, ethylbenzene, styrene and n -propylbenzene. Gas analysis showed hydrogen, methane, ethene and propene as additional reaction products. The mechanisms of both major and minor product formation are described.

Terbic ion as a sensitive probe: The dimerization of norbornene

Abstract Norbornene photodimerizes in the presence of the triplet sensitizer p-methoxyacetophenone. In the present work, the photodimerization of norbornene in degassed isopropyl alcohol in the presence of an added triplet quencher (Tb +3 ) was investigated. The terbium ion acceptor emits measurable fluorescence and was used for a quantitative evaluation of the transfer process. The quantum efficiency of Tb +3 fluorescence varied from 0.05 to 0.47 while the quantum yield of norbornene dimerization reached a maximum value of 0.1.