Conversion of Naphthenic Acids to Naphthene Hydrocarbons CHEMICAL CONSTITUTION

Goheen, Gilbert E.

doi:10.1021/ie50364a013

Cited by 8 publications

(6 citation statements)

References 5 publications

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“…This may be seen clearly in Table XI, where with similar amounts of oxygen absorbed the viscosity increase in the presence of phosphite was only half as great, and the proportion of the absorbed oxygen recovered as water was 15 per cent higher, than in its absence. The lower viscosity increase is an anticipated result of either reaction a or c, since acids and alcohols are far more viscous than the corresponding esters and unsaturated hydrocarbons (6).…”

Section: Dmentioning

confidence: 98%

Oxidation of Lubricating Oils. Factors Controlling Oxidation Stability

Fenske¹,

Stevenson²,

Lawson³

et al. 1941

Ind. Eng. Chem.

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A study of the oxygen absorption characteristics and the nature of the products obtained from oils oxidizing under controlled conditions has permitted the evaluation of a number of factors involved in lubricating oil deterioration.Investigation of selected fractions of a distillate stock has shown considerable variations in reactivity toward oxygen.The rate of oxygen absorption approximately doubles for each 100 C. temperature increase over the interval 140°to 180°C ., provided it is not limited by physical factors. The presence or absence of water vapor in the oxidizing atmosphere has little effect on the oxidation of one type of oil.The oxidation of certain oils can be reduced greatly by adding natural or synthetic inhibitors.

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Section: Dmentioning

confidence: 98%

Oxidation of Lubricating Oils. Factors Controlling Oxidation Stability

Fenske¹,

Stevenson²,

Lawson³

et al. 1941

Ind. Eng. Chem.

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“…Carboxyl groups were converted to methyl groups to facilitate separation and identification. Different methods for this conversion involving rather harsh conditions have been described in the past (36)(37)(38)(39)(40)(41)(42)(43). To minimize structural rearrangements while obtaining nearly quantitative conversions, the three-step transformation (44, 45) outlined in Figure 2 was developed for a mixture of crude oil carboxylic acids.…”

Section: Sulfur Compounds Benzdinaphthenesmentioning

confidence: 99%

Analysis of crude oil carboxylic acids after conversion to their corresponding hydrocarbons

Seifert¹,

Teeter²,

Howells³

et al. 1969

Anal. Chem.

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A new and comprehensive approach has been developed for the identification of carboxylic acids in virgin crude oil. Knowledge of the structures of these acids is relevant to questions concerning the origin of petroleum and the origin of life. The identification involves initial conversion of acids, via the corresponding alcohols and their p-toluene sulfonate esters, to hydrocarbons. The hydrocarbons are separated by a combination of silica gel and gel permeation chromatography and identified by ultraviolet, infrared, and high resolution mass spectrometry. For the acidhydrocarbon conversion, proof was obtained for the maintenance, on an average statistical basis, of most of the carbon skeletal structures of the original acids. The structure determination of the hydrocarbons and the retention of carbon skeleton during conversion permits identification of many classes of carboxylic acids not previously discovered in virgin crude oil. These classes include polycyclic naphthenic, mono-, di-, and polynuclear aromatic, mono-and dibenzthiophenic, carbazolic, and phenolic types. This identification procedure affords the first semiquantitative assessment of carboxylic acid classes in a crude oil relative to all of the acids present.

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“…15,23 Reduction of the iodides is usually carried out over zinc dust, in the presence of hydrochloric acid. 17, 18 The final reduction of other intermediates is often a repetition of the first step using LAH.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Synthetic routes adopted previously for conversion of NA to their hydrocarbon counterparts consisted of three-step transformations: reduction of the carboxylic acids or their methyl − or ethyl esters to the corresponding primary alcohols, followed by formation of tosyl or other derivatives and reduction of the tosyl, mesyl, , or iodide − intermediates to the hydrocarbons. An alternate, direct deoxygenation of petroleum acids was attempted by hydrogenolysis of the methyl esters over a nickel catalyst .…”

Section: Resultsmentioning

confidence: 99%

Structural Identification of Petroleum Acids by Conversion to Hydrocarbons and Multidimensional Gas Chromatography-Mass Spectrometry

Wilde

Rowland

2015

Anal. Chem.

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Identification of individual petroleum acids ("naphthenic" acids, NA) has proved challenging for decades, due to the extreme complexity of many petroleum acid mixtures. This has hindered detailed understanding of the role of NA in petroleum generation and oil production processes, refinery corrosion, as wood preservatives, and as environmental toxicants. Some recent advances have been made due to improved chromatographic separation of esters of the acids by multidimensional gas chromatography-mass spectrometry (GC × GC-MS), but relatively few reference spectra of esters are available for comparison. Here we report a complementary method based on a combination of a modified historical approach of converting NA to the corresponding hydrocarbons, followed by analysis by GC × GC-MS. Many published spectra exist for reference hydrocarbons making comparisons of reference spectra with those of the unknowns, much more feasible. As an example, we report identification of over 30 individual bicyclic naphthenic acids as the bicyclane hydrocarbons. These include both fused and bridged acids possessing methyl, dimethyl, and ethyl alkyl substituents as well as some terpenoid-derived acids. The study provides the most comprehensive analysis of one of the major classes of NA (the bicyclic acids) to date. There is now clear potential for this method to be used for the structural elucidation of other unknown acids (e.g., oil sands acids) and functionalized biomarkers in complex mixtures.

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Conversion of Naphthenic Acids to Naphthene Hydrocarbons CHEMICAL CONSTITUTION

Cited by 8 publications

References 5 publications

Oxidation of Lubricating Oils. Factors Controlling Oxidation Stability

Oxidation of Lubricating Oils. Factors Controlling Oxidation Stability

Analysis of crude oil carboxylic acids after conversion to their corresponding hydrocarbons

Structural Identification of Petroleum Acids by Conversion to Hydrocarbons and Multidimensional Gas Chromatography-Mass Spectrometry

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