Preparation, characterization and evaluation of mono‐and diesters of carboxystearic acid

Methyl mono‐, di‐, and tricarboxystearates were prepared by either a two‐step hydroformylation‐oxidation reaction or direct hydrocarboxylation of unsaturated vegetable oil methyl esters. Procedures were developed for preparing alkyl dicarbomethoxy‐, dicarboethoxy‐, and dicarbobutoxystearates. These triesters, along with some di‐ and tetraesters from mono‐ and tricarboxystearic acids, were evaluated as primary plasticizers for polyvinyl chloride (PVC). Except for butyl carbobutoxystearate, the esters were compatible at the 32% level and had properties equal or superior to those of dioctyl phthalate. Methyl and butyl diesters of carboxystearic acid had undesirable migration and volatility properties. The migration and volatility properties of some tri‐ and tetraalkyl esters were equal to or better than the controls. Of the various esters tested, methyl dicarbomethoxystearate containing 13–49% methyl tricarbomethoxystearate was an efficient plasticizer for PVC at the 32% level.

Section: Plasticizer Evaluationsupporting

confidence: 83%

Section: Di- Tri- and Tetraestersmentioning

confidence: 99%

Section: Plasticizer Evaluationmentioning

confidence: 99%

Section: Plasticizer Evaluationmentioning

confidence: 99%

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Some esters of mono‐, di‐, and tricarboxystearic acid as plasticizers: Preparation and evaluation

Dufek

Thomas

Frankel

et al. 1976

“…Kinetic studies of the esterification of distilled C19 dicarboxylic acid followed the procedure of Roe et al (11). VPC of the methyl esters was done on a 6 ftx 1/4 in.…”

Section: Mechanism Of the Koch Reactiorhmentioning

confidence: 99%

The preparation of C₁₉ dicarboxylic acid by the koch reaction

Lawson¹,

Cheng²,

Slezak

1977

AND SUMMARYThis paper describes the preparation of C19 dicarboxylic acid by the Koch reaction with carbon monoxide and sulfuric acid of oleic, tall oil fatty, and partially hydrogenated tall oil fatty acids. The effects of changing reaction conditions upon the yield and purity of the product were examined. With the best conditions, it was possible to prepare light-colored, heat-stable C19 dicarboxylic acid in 83% overall weight yield at 96% purity, containing 75% tertiary isomers and 25% secondary.

Lubricants and lubricant additives: I. Performance characteristics of N‐mono and N,N‐Disubstituted fatty amides and modified fatty amides

Magne

Mod

Sumrell

et al. 1974

A number of N‐mono and N,N‐disubstituted amides of substituted and unsubstituted C18 fatty acids have been prepared and evaluated as base lubricants and lubricant additives. The neat epithioamides possess extreme pressure lubricant characteristics and are noncorrosive at normal temperatures. The epithioamides also frequently function as extreme pressure additives and antiwear agents for paraffinic or diester base oils, sometimes in both capacities for both base oils. The intensiveness of these properties correlated directly with the degree of thiirane substitution in the compound. Performance in both these capacities at the same levels of epithioation was dependent upon the N‐ or N,N‐substituent groups present.