Richard Sasin

Evaluation of Long-Chain Phosphorus Compounds as Lubricity Additives

Two and 5% blends of a series of new long chain phosphates and phosphonates were examined for suitability as lubricity additives in bis(2-ethylhexyl) sebacate and mineral oil. The most effective anti-wear agents were diethyl stearoxyethyl-, dibutyl lauroxyethyl- and di (2-ethyl-hexyl) lauroxyethylphosphonate and dibutyl lauroxypropyl phosphate, the most promising extreme pressure agents were di(2-ethylhexyl) lauroxyethyl phosphonate, diethyl oleoxyethyl, diethyl oleoxybutyl, and dibutyl lauroxypropyl phosphates. Coefficient of friction measurements using steel on steel varied from that of the base fluid to 0.04. The latter was obtained with dibutyl lauroxypropyl, diethyl oleoxyethyl, and diethyl oleoxybutyl phosphates. The lubricity properties of the long chain phosphorus additives compare favorably with the values determined on presently used hypoid gear oils. The phosphorus derivatives also improved the oxidation stability of the diester but there appeared to be no improvement in rust prevention in eith...

Thiol esters of long-chain acids and long-chain alkanethiols

Summaryn-Nonyl throughn-octadecyl thiol esters of lauric, myristic, palmitic, and stearic acids are being reported for the first time. The four series of thiol esters show an alternation of melting points. The melting points of the even members fall on a single ascending curve. The melting points of the odd members fall on two separate ascending curves.

Benzamides, p-nitrobenzamides, benzenesulfonamides,p-toluene-sulfonamides, and acetamides as identification derivatives of long-chain amines

SummaryBenzamides, p-nitrobenzamides, benzenesulfonamides,p-toluenesulfonamides, p-nitrobenzenesulfonamides, and acetamides of dodecyl, tetradecyl, hexadecyl, and octadecyl amines were synthesized and evaluated as identification derivatives. Acetamides melt approximately 7° apart and the benzene sulfonamides approximately 6° apart. Seventeen previously unreported compounds were prepared.

X-ray diffraction powder data of some thiol esters of long chain fatty acids

SummaryX-ray diffraction powder data were obtained for 14 thiol esters of long chain fatty acids including benzyl, β-naphthyl,n-amyl, andn-hexyl thiol myristates; thiol palmitates; thiol stearates; and in some cases thiol laurates. All the individual compounds can be readily distinguished and identified by the diffraction data. Long spacings increase regularly with increase in hydrocarbon chain length. The benzyl and β-naphthyl thiol esters crystallize in tilted bimolecular layers while then-amyl andn-hexyl thiol derivatives crystallize in tilted monomolecular layers.

Phosphorus derivatives of fatty acids. The addition of dialkyl phosphonates to unsaturated acids and the synthesis of some 11-dialkylphosphonoundecanoamides

A series of dialkylphosphonoundecanoic acids and 9(10)-dialkylphosphonostearic acids was prepared by the addition of dialkylphosphonates to 10-undecenoic acid and oleic acid under free radical conditions in 58–66% yield. The phosphonates used were: dimethyl, diethyl, di-n-butyl, di-n-hexyl and di-2-ethylhexyl. All of the products are colorless, odorless, thermally stable liquids, insoluble in water and soluble in organic solvents. The dialkylphosphonoundecanoic acids were converted into the corresponding acid chlorides by reaction with oxalyl chloride. The acid chlorides were then converted into the corresponding amides by addition of ammonia. All of the amides are white waxy solids except the 2-ethylhexyl derivative which is a high-boiling liquid. Two of the dialkylphosphonoundecanoic acids were converted into the N-decyl substituted amides by heating withn-decylamine. The N-n-decyl-11-dialkylphosphonoundecanoamides are white waxy solids.

Solidification points of some binary mixtures of derivatives of stearic acid

SummaryThe solidification points of binary mixtures of stearic acid-stearamide, stearic acid-stearonitrile, stearic acid-1-octadecanol, and stearonitrile-stearamide were determined.

X-ray diffraction study of some normal alkyl thiolesters of long chain acids

SummaryX-ray diffraction-powder data are reported for 39n-alkyl thiolesters comprising four different series, namely, lauric, myristic, palmitic, and stearic acids. All individual compounds can be identified and distinguished by the X-ray diffraction data. Compounds containing the same total number of carbon atoms in the molecule have the same long and side spacings but differ in the relative intensities of the various orders of the long spacings. The esters crystallize in tilted monomolecular layers. The long spacing is a function of the total carbon content of the molecule and forms two series, one for the odd members and one for the even members. A change in the structure-type definitely occurs in the odd series on decreasing alkyl chain-length below 9 carbons.

Viscosity studies of some long-chain thiol esters

Viscosity studies of thiolaurates, thiomyristates, thiopalmitates and thiostearates of the normal C6, C7, C14, C16, C18; C6, C8, C10, C11, C13, C14, C15, C16, C18; C9, C10, C11, C12, C13, C14, C16, C17, C18 and C4, C9, C10, C11, C12, C14, C16 and C18, respectively, were made. In addition,n-propyl andn-heptyl thioacetates as well asn-heptyl thiohexanoate were studied. Viscosities of thiol esters increase with increasing chain length. These increases are not linear. For each compound, the viscosity decreases with increasing temp. Activation energies for viscous flow were calculated. The activation energies increase as the chains increase. These increases are not linear.

Substituted sulfonamides, ureas, and alkyl-3-nitrophthali-mides as identification derivatives of pentyl-, hexyl-, heptyl-, octyl-, and decylamines

Summaryp-Bromo-,m-nitro-,p-nitrobenzenesulfonamides,p-toluenesulfonamides,p-tolyl-, anda-naphthylureas, and 3-nitrophthalimide derivatives of pentyl-, hexyl-, heptyl-, octyl-, and decylamines were prepared.m-Nitrobenzenesulfonamides,p-nitrobenzensulfonamides, andp-tolylureas appear to be the most satisfactory derivatives for the identification of these amines.

X-ray diffraction powder studies of some dithiol diesters of long chain acids

X-ray diffraction powder data are reported for 25 mono- and dithiol diesters of straight chain aliphatic acids where the acid portion of the molecule consists of one of the following acids: octanoic, decanoic, dodecanoic, tetradecanoic, hexadecanoic or octadecanoic acids, and where the thiol portion consists of one of the following: 2-mercaptoethane, 1,2-ethanedithiol, 1,3-propanedithiol, 1,4-butanedithiol or 1,5-pentanedithiol. The individual compounds can be identified and distinguished by the long spacing data. The compounds crystallize in tilted monomolecular layers.