Selective Alcoholysis Products of Methyl 9,9-Dimethoxynonanoate.

Pryde, E. H.; Moore, D. J.; Teeter, H. M.; Cowan, J. C.

doi:10.1021/je60024a021

Cited by 14 publications

(7 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Ester-acetals such as 4 offer the opportunity for selective reactions at either functional group, as we have shown earlier for the acetals of alkyl azelaaldeliydates (8). As already mentioned, saponification of 4a gave 3.…”

Section: Acetalationmentioning

confidence: 54%

ChemInform Abstract: GEMINAL HYDROXYMETHYL COMPOUNDS FROM 9(10)‐FORMYLSTEARIC ACID

Miller¹,

Pryde²

1978

Chemischer Informationsdienst

Self Cite

View full text Add to dashboard Cite

from ABSTRACT AND SUMMARY9(10)-Formylstearic acid and methyl 9(10)formylstearate reacted with formaldehyde in basic methanolic or aqueous medium to undergo the Tollens condensation, followed by a crossed Cannizzaro reaction to give 9,9(10,10)-bis(hydroxymethyl)octadecanoic acid in essentially quantitative yield. This 2,2-disubstituted-l,3-propanediol has been esterified on the carboxyl group and the hydroxymethyl groups have been acetylated and acetalated with acetone to give a series of stable liquids boiling at ca. 200 C/0.005 mm and freezing at <-70 C.

show abstract

Section: Acetalationmentioning

confidence: 54%

ChemInform Abstract: GEMINAL HYDROXYMETHYL COMPOUNDS FROM 9(10)‐FORMYLSTEARIC ACID

Miller¹,

Pryde²

1978

Chemischer Informationsdienst

Self Cite

View full text Add to dashboard Cite

show abstract

“…We have characterized the known as well as the new alkyl azelaaldehydates since published data on the methyl and ethyl esters are not in good agreement (see footnotes, Table I). The diethyl acetal of EAZ is included; the dimethyl acetal of methyl azelaaldehydate and several other azelaaldehydate acetals have previously been satisfactorily characterized (13,15). All the molar refractions determined experimentally are in close agreement with the calculated values except for the isopropyl compound which is 0.43 unit higher than calculated.…”

Section: Alkyl Azelaaldehydates: Physical Propertiesmentioning

confidence: 59%

Alkyl azelaaldehydates of high purity from alkyl soyates: Preparation and properties

Awl¹,

Pryde²,

Weisleder³

et al. 1971

J Americ Oil Chem Soc

Self Cite

View full text Add to dashboard Cite

Reductive ozonolysis of appropriate alkyl soyates in various participating media producted methyl, ethyl,n‐propyl, isopropyl andn‐butyl azelaaldehydates in good yield and high purity (98+%). The participating media examined were: methyl, ethyl,n‐propyl andn‐butyl alcohols; mixtures of an alcohol and acetic acid; water; and mixtures of water and acetic acid. Any combination of solvent and ester, except methanol‐methyl soyate, allowed good separation by fractional distillation of ester and acetal impurities from the azelaaldehydate. A preparative method was developed by which high purity ethyl azelaaldehydate is produced from soybean oil by reductive ozonolysis in water. The only major impurity by this method was ethyl hydrogen azelate, which was easily removed with a bicarbonate wash. After a single fractional distillation with a short Vigreux column, the azelaaldehydate was obtained in 78% yield and 98+% purity. Physical properties and spectral (IR, NMR and mass spectroscopy) and chromatographic data were determined for the pure alkyl azelaaldehydates. Several of these properties were also determined for acetal and diester byproducts.

show abstract

“…Ethylene acetal 8A of Table I was prepared from distilled safflower DMA (acetal 8, Table I) by the transacetalation procedure of Pryde, et al (11,12).…”

Section: Eamentioning

confidence: 99%

Ethylene and dimethyl acetals from hydroformylated linseed, soybean, and safflower methyl esters as plasticizers for polyvinyl chloride

Awl

Frankel

Pryde

et al. 1974

J Americ Oil Chem Soc

Self Cite

View full text Add to dashboard Cite

Dimethyl and ethylene acetals of polyformylated unsaturated fatty esters were prepared, characterized, and evaluated as polyvinyl chloride plasticizers. Dimethyl acetals were prepared with trimethyl orthoformate as a water scavenger in the acid catalyzed acetalation reaction. With ethylene acetals, water was removed azeotropically. Although the acetals prepared were mixtures, molecular distillation gave diacetal esters of 80–90% purity and triacetal esters of 80–95% purity. The samples were characterized by gas liquid chromatography and by IR and NMR spectra. Compared to di‐2‐ethylhexyl phthalate as a plasticizer for polyvinyl chloride, the triacetal esters (both dimethyl and ethylene acetals) gave less migration and at least equivalent volatility characteristics; the triacetals also gave equivalent compatibility and strength, but somewhat less desirable low temperature and heat stability properties. The diacetal esters also had good compatibility, equivalent strength, somewhat better low temperature, but less desirable migration and volatility properties.

show abstract

Selective Alcoholysis Products of Methyl 9,9-Dimethoxynonanoate.

Cited by 14 publications

References 8 publications

ChemInform Abstract: GEMINAL HYDROXYMETHYL COMPOUNDS FROM 9(10)‐FORMYLSTEARIC ACID

ChemInform Abstract: GEMINAL HYDROXYMETHYL COMPOUNDS FROM 9(10)‐FORMYLSTEARIC ACID

Alkyl azelaaldehydates of high purity from alkyl soyates: Preparation and properties

Ethylene and dimethyl acetals from hydroformylated linseed, soybean, and safflower methyl esters as plasticizers for polyvinyl chloride

Contact Info

Product

Resources

About