The formation of 1, 4-cyclohexadiene by olefin metathesis reaction catalyzed by WCl6-cocatalyst systems was studied in detail. In the reaction of methyl linoleate, the order of the activity of cocatalysts was changed by varying cocatalyst/WCl6 ratio, and the activity of cocatalysts which is expressed by the highest yield of 1, 4-cyclohexadiene and 6-dodecene obtained by varying the ratio decreased in the order; SnBun4>SnMe4>AlEt3>SnEt4. In most reactions at 80°C for 3h the olefin/WCl6 and the SnBun4/WCl6 ratios in the optimum reaction conditions were about 30 and 68, respectively. The highest yields of 1, 4-cyclohexadiene in the reactions catalyzed by WCl6-SnBun4 system were 170 (methyl linoleate without solvents), 24% (methyl linoleate in chlorobenzene), 22% (sufflower oil without solvents), 44% (linseed oil without solvents) and 56% (linseed oil in chlorobenzene).

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In order to develop a useful application of α-olefins, investigation was undertaken to synthesize branched fatty acids by the reaction with water and carbon monoxide generated in situ using sulfuric acid and formic acid with a view to employing these branched acid for solvent extraction of metal.
The highest yield of the branched acid was obtained when 1mol of α-olefin was reacted with 12mol of sulfuric acid and 2mol of formic acid (85%) at 25°C. for 2h.
The solvent extraction of metal such as Cu, Pb, Cd and Zn was conducted using the branched acids derived from 1-hexene, 1-octene, and 1-decene. Experimental results showed that these branched acids exhibited excellent extractability superior to those of straight chain fatty acids such as capric acid.

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Fluorinated nonionic surfactants : CF₃ (CF₂) ₅CH₂O (C₂H₄O) pH, CF₃ (CF₂) ₅CH₂CH₂O (C₂H₄O) pH, and CF₃ (CF₂) ₇CH₂CH₂O (C₂H₄O) p'H (p=1, 3, 5, 10, 20, p'=1, 3) were prepared by the addition of ethylene oxide (EO) to long-chain fluoroalcohols in the presence of a base or an acid catalyst and their physicochemical properties were clarified.
Cloud points of aqueous solutions of those adducts were found to be higher with increase in the number of oxyethylene units. For the same number of oxyethylene units, these cloud points decreased with increase in the carbon chain length of the starting alcohols. Among those adducts, CF₃ (CF₂) ₅-CH₂O (C₂H₄O) pH showed the best surface activities; especially the 10mol EO adduct had a strong emul-sifying power toward xylene, and the 20mol EO adduct exhibited a good foaming property. Aqueous solutions of these adducts generally had low surface tension, and CF₃ (CF₂) ₅CH₂O (C₂H₄O) ₃H showed the lowest aqueous surface tension (15.4dyn/cm) of the adducts. The cmc values for the fluorinated surfactants increased with increase in the number of oxyethylene units.
These results were compared with those reported previously, and discussion was made on the characteristics of the surface activities of the fluoroalcohol- EO adducts.

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Polyurethaneamine (PUA) was prepared from N-methyldiethanolamine and hexamethylenediiso-cyanate. A variety of quaternary ammonium salts of PUA (cationic polymer) were prepared from PUA and alkyl bromides of various chain length (C₂C₁₂) with a view of obtaining good flocculants. In alkylating PUA with alkyl bromides, it was found that alkylation occured to urethane-N as well as quaternization reaction, and using low molecule of urethane as model compound prepared from ethanol and hexamethylenediisocyanate, alkylation to urethane-N was ascertained by the reaction of urethane and dodecyl bromide. The flocculation ability for aqueous suspension of kaoline was investigated in the relation to the structure of cationic polymers by measuring the sedimentation velocity, sedimentation volume, and turbidity. Cationic polymer obtained from PUA and the higher alkyl bromide showed good flocculation effect. The suitable range of degree of quaternization was 4060%. Cationic polymer was most effective for flocculation with increase of acidity. The most clarity of supernatant gave 40ppm turbidity at the dosage of 50ppm using cationic polymer (degree of quaternization 84.4%) obtained from PUA and dodecyl bromide. Interraction (metachromasia) between methyl orange and cationic site of a number of cationic polymers were examined, and cationic polymers with the higher degree of quaternization derived from the higher alkyl bromides and PUA were shown large metachro-masia. Cationic polymers derived from the higher alkyl bromides showed good flocculating ability which are not inferior that of typical commercial products.

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The moisture regain of textile fibers and the water content in solution equilibrated together with then were determined in the presence of various amounts of water solubilized by 0.1M Aerosol OT in perchloroethylene at 10°C, 20°C and 30°C. Simultaneously, the vapor pressure of solubilized water was measured at each temperature. Rayon, wool, nylon and acryl were used as test fabrics.
The differential heat of absorption of water vapor (ΔHV) on the fabrics was calculated from the slope of linear plots of logarithm of the vapor pressure against the reciprocal of the absolute tempera-ture at given regains. ΔHV decreased with increase of moisture regain of the fabrics and with increase of solvent relative humidity in the solution. When the fabric and solution were in equilibrium with atmosphere, ΔHV was explained by the sum of the heat of solubilization (ΔHS) and the heat of solvation (ΔHH) of water. The decrease in free energy and the entropy change accompanying the absorption of water on the fabrics were also calculated approximately from the present data. It was concluded that the water was held by the fabrics in two different states; i.e., bound water and free water, near-by 75% solvent relative humidity in nonaqueous solution.

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3-Hydroxy acids were synthesised in good yield from ketones and carboxylic acids using lithium naphthalenide in the presence of diethylamine. From cyclohexanone and propionic acid, 2- (1-hydroxy- cyclohexyl) propionic acid (3) was obtained in 98% yield. 3-Hydroxy acids were treated with various acidic reagents to give 3, 4-unsaturated carboxylic acids and γ-butyrolactones. From the reaction of (3) with p-toluenesulphonic acid, 2- (1-cyclohexenyl) propionic acid (4) was obtained (yield 98%) and with 97% sulphuric acid 2- (2-hydroxycyclohexyl) propionic acid lactone (5) was formed (93% yield).
We have found that an 2, 3-unsaturated δ-lactone or spirolactone could be prepared from the reaction of 3-hydroxy acid with 1, 3, 5-trioxane or paraformaldehyde. When a mixture of the compound (3), 1, 3, 5-trioxane, and sulfuric acid was refluxed in acetic acid, 2- (2-hydroxymethylcyclohexylidene) propionic acid lactone (6) was obtained in 88% yield; interestingly, at 25°C, only 2, 5-dimethyl-4, 6-dioxa-3-oxo spirobicyclohexane (7) was obtained in 71% yield.
3, 4-Unsaturated acids were condensed with paraformaldehyde in boiling acetic acid containing a small amount of aluminium chloride to afford 2, 3-unsaturated δ-lactones. From 2- (1-cyclohexenyl) octanoic acid (8) and paraformaldehyde, 2- (2-hydroxylmethylcyclohexylidene) octanoic acid lactone (9) was obtained in up to 93% yield.

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The synthetic reaction of alkyl chloroacetates (1) with ethylene oxide (EO) in N, N-dimethylacet-amide (DMA) was studied. EO was inserted into the C-Cl bond of t-butyl, hexyl, octyl, 1-methyl-heptyl and decyl chloroacetates to form novel compounds, alkyl 2-chloroethoxyacetates (2), although the insertion of EO into the C-Cl bond of 1-chlorooctane did not occur under the same conditions. Zinc chloride and lithium halide were effective catalysts in the present reaction. Optimum amounts of DMA and of zinc chloride to (1) were equimolar and 1/30-1/10 molar, respectively, and optimum temperature was at 110120°C. The effect of the structure of alkyl group of (1) on the yield of (2) was studied. The branching and increasing of alkyl chain diminished the yield of (2).

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Sodium N-cyclohexyl-N-n-alkylaminopropan (or ethane) -1-sulfonates (alkyl : butyl-, hexyl-, octyl-) were prepared, separated, refined, and identified. Studies on some physicochemical properties of these aqueous samples solutions were carried out. From these obtained results, it is concluded that these samples were good as surface active and bufferring agents.

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