Butyric, hexanoic, octanoic, decanoic, and lauric acids were formed by the peroxide-induced addiion of acetic acid to ethylene in which ethylene and di-t-butyl peroxide were feeded into acetic acid continuously. 2-Ethylbutyric, and 2-ethyloctanoic acids, and neutral substances were also formed. Major neutral substances formed were assumed to be dibutyl and di(2-ethylhexyl) phthalates, and 3, 4-dibutyl-, 3-butyl-4-hexyl-, and 3, 4-dihexyl-2, 5-oxolanediones.
For the purpose of standardizing the method of fat and oil stability test by both some oil mills and oil users, the stability test on autoxidation was taken up as the 1st step, and collaborative tests were implemented by AOM test, oven test, organoleptic evaluation method and weighing method. 1. Results of AOM test In inverse proportion to the length of storage period of soybean oil the induction period became shorter. Comparing capped oil with uncapped oil, there was no deviation in AOM stability between 15 days stored oil and 30 days stored oil. In the case of 108 days stored soybean oil, uncapped stored oil clearly showed much shorter induction period, compared with capped stored oil. Deviations among the collaborators were small. 2. Results of oven test
The fatty acids of the seed oil of Lindera strychnifolia (Sieb. et Zucc.) F. Viii. isolated by distillation, column chromatography and preparative gas chromatography were identified by gas chromatography, infrared, mass and nuclear magnetic resonance spectrometry. The fatty acids identified were decanoic, dodecanoic, cis-4-dodecenoic, tetradecanoic, cis-4-tetradecenoic, hexadecanoic, hexadecenoic, octadecanoic, oleic, linoleic and eicosenolc acid. The major component was cis-4-tetradecenoic acid.
Three well separated peaks assigned to isolated orthophosphate and end, and middle phosphates groups in linear polyphosphoric acid were found in 31p NMR spectra of the reaction mixtures. Relative proportions of these structural building units as well as orthophosphate and unreacted alcohol as a function of the ROH/P4O10 mole ratio were determined. The results obtained were discussed.
Several new polycarboxylic acids containing ether linkages were prepared and their building performances were compared with those of disodium oxadiacetate, disodium tartronate, disodium aminomethyltartronate, disodium (methylamino) methyltartronate and sodium tripolyphosphate (STPP) usingalkylbenzene sulfonate (LAS). The detergency tests were carried out on naturally soiled cotton fablics and the detergency powers were evaluated by Scheffe's method. From the results summarized in Fig.-1, it is evident that trisodium salt of 1, 1, 1-tris (carboxymethoxymethyl) ethane shows a building performance slightly superior to that of STPP, but the corre-sponding tripropionate does not show the good building power. In case of the tri-basic acids, triacetic acids are much more active than tripropionic acids. And the washing efficiency of tetrapropionic acid is about the same as that of tripropionic acids. It seems that their weak building powers are depend upon their relatively weak abilities to catch calcium ions.
Long chain N-acyl amino acids have good surface activities and the application of these surfactants have been expanded. Long chain N-acyl amino acids were usualy prepared by the Schotten-Baumann method but this method was not suitable enough for an industrial detergent production. In this report, the acylation of amino acids by long chain fatty acid-sulfonic acid mixed anhydride (FSA) was described. FSA obtained from long chain fatty acid and sulfur trioxide was unstable and the acylation of amino acids by this FSA resulted in low yields. However, the triethylamine salt of long chain fatty acid-sulfonic acid mixed anhydride (FSAT) obtained by the reaction of long chain fatty acid with sulfur trioxide in the presence of triethylamine was more stable than FSA, and the FSAT was a good acylation reagent. The structure of FSAT was also investigated.
Many natural terpenic compounds are known to have skeltons of 1-4 addition of isoprene. But few terpenic compounds have been synthesized hitherto. We shall now report the synthesis of citronellol VII-a natural monoterpene alcohol-from isoprene. The reaction consists of the f olloouing four steps ; (1) Catalytic dimerization and alcohol addition of isoprene in the presence of (π-allyl PdCI) 2, phos-phine, and NaOMe. The yield of II is up to 97.5% when PPh3 : (π-allyl PdCI) 2=2 : 1 and 2 days reaction at room temperature. (2) Dealcohol reaction of If or V is carried out in the presence of [P (η-Bu) 3] 2 NiCl2 and NaOMe as catalytic system, (3) Selective 1-4 hydrogenation of conjugated diene is carried out in the presence of Cr (CO) 3 (C6H, -COOMe) as a catalyst under hydrogen atmosphere to form IV or VI. (4) Terminal hydration of terminal double bond is carried out by hydroboration and following alkaline hydrolysis to obtain V or VII. Two synthetic routes are practically possible and the overall yield of citronellol is ca. 40% in each case.
Cyclic monomer fraction (β-CMF) was obtained from methyl β-eleostearate heated at 250°C for 10 hour under an inert atmosphere. The composition of β-CMF was identified by comparing its gas chromatogram with those of the synthesized C18 cyclic fatty acid esters. Consequently, a few cyclohexyl compounds, e.g., methyl 8- (2-η-butyl cyclohexyl) η-octanoate, were find out as small peaks on earlier retention time of the gas chromatogram. These results supported that the aromatic compounds were derived from the cyclohexadiene systems by disproportionaion reaction.
One hundred and forty eight kinds of novel quaternary ammonium compounds were prepared by the reaction of tertiary amines with terpenyl monohaloacetic acid esters which were obtained from esterification of terpene alcohols with monochloroacetic acid or monobromo acetic acid. Antimicrobial activities of these quaternary ammonium compounds were investigated. We observed considerable antimicrobial activity for the compounds ,  and .
The fatty acids from seed oil of Canarium album Raeusch, were investigated by means of gas chromatography, mass, nuclear magnetic resonance and infrared spectra. The acids identified were hexanoic, octanoic, decanoic, lauric, myristic, stearic, palmitic. oleic, linoleic and two C18 : 2 acids. The major component was linoleic acid.