The Reaction of Maleic Anhydride With Polynuclear Aromatic Hydrocarbons

Jones, Richard N.; Gogek, C. J.; Sharpe, Robert W.

doi:10.1139/cjr48b-074

Cited by 8 publications

(2 citation statements)

References 1 publication

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“…Also, the attainment of the equilibrium is favored by an increase in temperature, but the latter is limited by the thermal dissociation reaction. The optimum reaction conditions employed in this work followed closely those established by previous investigators (2,14,16), although some modifications were dictated by the occasional interference from asphaltic and tarry reaction products.…”

Section: Reaction With Maleic Anhydridementioning

confidence: 87%

Properties of High Boiling Petroleum Products. Physical and Chemical Characterization Studies with Relation to Polynuclear Aromatic Components

Wanless¹,

Eby²,

Rehner³

1951

Anal. Chem.

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Section: Reaction With Maleic Anhydridementioning

confidence: 87%

Properties of High Boiling Petroleum Products. Physical and Chemical Characterization Studies with Relation to Polynuclear Aromatic Components

Wanless¹,

Eby²,

Rehner³

1951

Anal. Chem.

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“…SEVERAL physical and chemical properties of polycyclic aromatic hydrocarbons have shown limited correlation with carcinogenic activity. These include reactions with perbenzoic acid (7), lead tetraacetate (9), osmium tetraoxide (2, 3,18), p-nitrobenzenediazonium chloride (8), and maleic anhydride (12,18). However, none of these reactions has proved to be particularly useful as a method for predicting the carcinogenic properties of high boiling petroleum fractions.…”

Section: Maynard E Hall1mentioning

confidence: 99%

Properties of High Boiling Petroleum Products

Eby¹,

Priestley²,

Rehner³

et al. 1953

Anal. Chem.

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ANDThe only methods heretofore described for predicting carcinogenic activity have been limited to series of pure aromatic compounds or to high]>-specialized types of petroleum products. After examination of a number of different reactions and properties of polycyclic aromatic compounds, five nonbiological methods have been developed for the prediction of tumor potency of high boiling petroleum products. Each method gave about the same degree of correlation with biological data. These physical-chemical methods are all based upon measurements of certain types of polycyclic aromatic hydrocarbons. The results support the premise t h a t the carcinogenicity is a function qf the concentration of these types of compounds in oils. The methods, therefore, obviate the necessity of isolating or analyzing the actual carcinogenic compounds. The caffeine number method is preferred for routine analytical work. It is based upon a n ultraviolet examination of a n aqueous caffeine extract of the aromatic hydrocarbons. A standard deviation of 8.4 was obtained for the difference between the predicted and the biological tumor potency values of 123 different products. Reproducibility of the caffeine number was better than t h a t of the biological data. Comprehensive analytical data for all five methods are presented for a variety of high boiling petroleum products. These demonstrate t h a t a choice of methods is available, depending upon the particular types of products to be analyzed and the facilities a t hand.

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The Retro–Diels–Alder Reaction PartI.CCDienophiles

Rickborn

1998

Organic Reactions

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The Diels–Alder (“DA”) reaction is so familiar to organic chemists that the retro‐Diels–Alder or retro‐diene reaction (hereafter “rDA”) requires no conceptual introduction. However, a working definition is needed to indicate the coverage of this review. The intent is to include all reported examples of the general skeletal process excluded in this chapter. Any of the atoms in the starting material (cycloadduct) may be carbon or heteroatom, and substituents on all positions are allowed. In addition, any bond order available to the element in any oxidation state is included, as well as bonding to non‐nearest neighbor atoms (bicyclics, etc.). The volume of literature required separation of this review into two parts. Part I covers all expelled C–C dienophiles, i.e. those reactions that generate a new carbon‐carbon double or triple bond in the dienophile that is formed. Part II, to appear later, covers those expelled dienophiles in which one or both atoms is a heteroatom. Certain specific topics are intentionally omitted. These are: rDA reactions invoked under mass spectral conditions; rDA reactions of polymeric substrates; Electrocyclic processes, some of which are arguably very similar to rDA reactions (these are not addressed unless needed for clarification of an rDA sequence); and a thorough discussion of homo‐rDA reactions. CAS‐Online searches resulted in ca. 1,300 references, of which ca. 900 proved pertinent to the rDA topic as defined and delimited above. Active literature searching was halted in April 1995, but occasional more recent articles are included. Over 2,500 pertinent references were eventually found. Most were obtained by perusal of primary literature (articles) and secondary sources (books and reviews). Computer based search success was limited mainly by the failure of authors or abstractors to key‐word this topic, an especially common occurrence when the expelled dienophile was a simple substance such as N 2 or CO 2 . Overall, approximately 3,500 books, chapters, reviews, articles, and abstracts were consulted in an effort to make this review as comprehensive as possible. This was done with the certainty that some pertinent literature would be missed, tempered by the view that these omissions are probably also lost to any future rational search method. Many secondary sources proved valuable not only for in‐depth discussion of certain rDA reaction types, but also for providing comparisons with related topics. To assist the reader, these secondary sources are referenced (alphabetically by first author within broad subject areas) with a title or brief note on the topic(s) addressed. The first group lists earlier reviews with primary focus on rDA reactions, followed by items of Historical/General Interest, reviews that deal with Experimental Methods, DA reactions (general and specific), reviews of Related Topics (these impinge in more or less significant ways on rDA reactions), and general treatments of Theory and Mechanism.

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The Reaction of Maleic Anhydride With Polynuclear Aromatic Hydrocarbons

Cited by 8 publications

References 1 publication

Properties of High Boiling Petroleum Products. Physical and Chemical Characterization Studies with Relation to Polynuclear Aromatic Components

Properties of High Boiling Petroleum Products. Physical and Chemical Characterization Studies with Relation to Polynuclear Aromatic Components

Properties of High Boiling Petroleum Products

The Retro–Diels–Alder Reaction PartI.CCDienophiles

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