Pancreatic lipase was purified by dialysis, acetone fractionation, methanol washing and trichloroacetic acid. The reaction of purified lipase and metals was conducted in water at 37°C for 20 hours and obtained its complex. The complex was purified by methanol washing. The metal content and IR spectrum of isolated complex were determined.
From the experimental results, it was found that the formation of lipase-metal complex was easy as well as casein-metal complex. The complex showed the same pattern as the lipase or metal after gel filtration though Sephadex G75, but the metal in lipase-metal complex was not removed by dialysis, acetone fraction and methanol washing etc.. Therefore it seems clear that such a binding between lipase and metal is strong.

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In the previous papers, the authors reported and made clear the easy formation of metal-melanoidin complex in system of aqueous solution.
In this paper, the relationship between the binding ability of melanoidin (M) and metal in oil, or M-metal complex on the rancidification of oil was investigated.
Then the M (prepared from a mixture of glycine and D-xylose by heating at 100°C for 5 hour) was reacted at usual and high temperatures with copper sulfate or ferrous chloridein oil.
From the experimental results, it was found that the formation of M-metal complex and the amount of M-metal complex increased with the longer reaction time in the system of oil.
For the antioxidative effect of these materials it was found that the rancidity of lard was highest in the cases of M and metal mixture and M-metal complex, but in the case of soybean oil the peroxide value remained low.
Consequently, it was recognized that M acted as a potent synergist of antioxidants as well as tocopherol and BHA under certain conditions.

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Isopulegyl acetate [1] and neo-isopulegyl acetate [2] were oxidized with selenium dioxide in aqueous ethanol under reflux. The oxidation of (-) - [1] gave (-) - (1R : 3R : 4S) -8 (10) -p-menthene-3-acetoxy-9-al [1a] and -9-ol [1b]. The oxidation of (+) - [2] gave (+) - (1R : 3S : 4S) -8 (10) -p-menthene-3-acetoxy-9-al [2a], -9-ol [2b], (-) - (1R : 3S : 4S) -8-p-menthene-3-acetoxy-4-ol [2c], (+) - (1R : 3S : 4R) -8-p-menthene-3-acetoxy-4-ol [2d] and (+) - (1R : 3S : 4R) -8 (10) -p-menthene-3-acetoxy-4, 9-diol [2e]. The mechanism of allylic oxidation of olefins with selenium dioxide was visualized in two stages, the first involving the formation of the allylic selenite ester and the second the solvolysis of this ester. In the case of [2], the allylic selenite ester [A] and [B] were produced and then the solvolysis of these esters gave -9-ol [2a] and -4-ols ([2c], [2d]) respectively. In the case of [1] the formation of the allylic selenite ester [C] is required for the production of -4-ol. Since the ester [C] introduces an interaction between acetoxy group and isopropylidene group by eclipsing, the formation of [C] would be unfavorable. In agreement with this, GLC analysis failed to show the presence of any -4-ols. In the solvolysis step of [A], the trans-attack of the water molecule to acetoxy group would be preferable to the alternative cis-attack, since the cis-attack produces a skew-like interaction between acetoxy group and hydroxy group. Indeed the yield of [2d] produced by the trans-attack was twice the yield of [2c] produced by the cis-attack.

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Bis (7, 7-dimethyl-2-oxa-7-silaoctyl) methanol was prepared from epichlorohydrin and 5, 5-dimethyl-5-silahexanol. The polyaddition of ethylene oxide (EO) to the obtained carbinol in the presence of base gave a series of new type nonionics having two hydrocarbon chains terminated with trimethylsilyl groups; [(CH₃) ₃Si (CH₂) 4OCH₂] ₂CHO (C₂H₄O) mH (SiGDE-series). Some properties were compared with those of α, α'-glyceryl dioctyl ether-EO adducts; [CH₃ (CH₂) 7OCH₂] ₂CHO (C₂H₄O) mH (GDE-series) and n-hexadecanol-EO adducts; CH₃ (CH₂) ₁₅O (C₂H₄O) mH (S-series). At the same m, cloud points of SiGDE-series were lower than those of GDE-series. Surface tension lowering abilities of SiGDE-series in aqueous and polyoxyethylene glycol were higher than those of GDE-series. SiGDE-series remarkably lowered interfacial tensions of kerosene and silicone oil-water system. Foaming, wetting and emulsifying powers of SiGDE-series were superioer to those of GDE- and S-series.
These results were discussed from viewpoint of the application to industries.

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The individual removals of linear alkylbenzene sulfonate (LAS), branched alkylbenzene sulfonate (ABS), alpha olefin sulfonate (AOS) and sulfate type surfactants in sewage treatment plants have been examined for one year. This was accomplished by infra-red spectroscopic analysis of anionic surfactants in raw municipal sewage and effluent from sewage treatment plants.
The individual removals of anionic surfactants in sewage treatment plant were ca. 85%, 35%, and 100% for LAS, ABS, and AOS and sulfate-type surfactants, respectively. Then, the removals of biochemical oxygen demand (BOD) and soluble total organic carbon (TOC) were 90 and 68% respectively.

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For the syntheses of d, l-perillaldehyde [6] and l-perillaldehyde [6'], they were prepared by the isomerization and dehydrogenation of d, l-myrtenal [3], l-myrtenol [4], and l-perillyl alcohol [5] with a copper-zinc catalyst, at 215235°C under reduced pressure.
In this method, [6] and [6'] were obtained in high yields almost holding optical purities of starting materials ([3], [4], and [5]) with negligible amount of by-products. This method is, therefore, superior to the conventional one to obtain perillaldehyde from isomerization and dehydrogenation of [3], [4] and [5].

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The samples for gas chromatographic analyses of the representative lower sulfur compounds such as carbonyl sulfide, hydrogen sulfide, carbon disulfide, methyl mercaptan and sulfur dioxide in the exhaust gases from two corn starch factories, i.e., an unautomated and an automated factories, were prepared by direct cold trap with liquid oxygen and detected by the flame photometric detector.
The detected concentration ranges and average values of the five representative lower sulfur compounds in the exhaust gas from the unautomated factory were as follows; carbonyl sulfide 0.020.03ppm (ave. 0.025ppm), hydrogen sulfide 0.52.1ppm (ave. 1.3ppm), carbon disulfide 0.01ppm (ave. 0.01ppm), methyl mercaptan 0.30.6ppm (ave. 0.45ppm), sulfur dioxide 0.10.3ppm (ave. 0.2ppm), or dimethyl sulfide 0.050.1ppm (ave. 0.075ppm).
On the other hand, those from the automated factory were as follows; carbonyl sulfide 0.02ppm, hydrogen sulfide 0.02ppm, carbon disulfide 0.004ppm, methyl mercaptan 0.01ppm, rather high concentration of sulfur dioxide being 680ppm.

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Optimum conditions for the oxidation of dimethylsulfide and dimethylsulfoxide to dimethylsulfone, olefins to epoxides, ketones to esters, and azobenzene to azoxybenzene with peracid type resin have been investigated. The Baeyer-Villiger reaction of cyclohexanone, cyclopentanone and other aliphatic ketones with the resin very rapidly in aqueous medium.

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