n-Hexane has been generally used as the extraction solvent for soybean extraction. In n-hexane extraction, however, it is difficult to remove solvent from the miscella and meal perfectly at low temperature. The solvent removal is usually carried out at a higher temperature of about 100°C., consequently, quality of the oil and meal extracted with n-hexane becomes inferior. Especially, denaturation of protein in the soybean oil occurs more evidently with the elevated temperature during solvent removal. This study has been made to improve the quality of extracted oil and meal by using liquid butane as the extraction solvent and by processing at lower temperature, about 5060°C.
As a result, the liquid butane was useful as the extraction solvent under an optimum extraction condition. Butane-extracted oil has lighter color, low acid value and low lecithin content. The denaturation of protein in the meal does not occur during the solbent-removal process.

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The deterioration and rancidity of the oil are caused by the free radicals formed in oil which have a catalytic and chain reactive character for oxidation.
These free radicals are more accelerated by the frying temperature and metallic fry-fitting.
The objective of this experimental work was to investigate how the oil deterioration is accelerated under the usual additional-frying method which replenishes fresh oil to the loss. Another method is the “Circulation method” whereby oils is not supplied, but rotated fry oils was compared with the usual frying method.
The detail of this experiment was as follows; 6kg of soybean oil, 36kg of fry material (344 persons), 14 batch of fry-times (7hr in total) and 52-day-period. As a result, the usual method was deteriorated more rapidly than the another.
From the carbonyl value and conjugated dienoic acid content, distinction in oil stability between the two type flying-method has been shown in each period.

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This research was carried out to find the configuration of the palm oil, tallow and lard which were most useful natural fats in our fat and oil industries.
Each fat was separated by fractional crystallization and the typical fractions were analyzed by means of pancreatic lipase hydrolysis.
As a result, the main structure of each glyceride was determined.

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With a view to studying the effects of the polar groups of rust inhibitors upon the results of different corrosion tests, we took up in the last installment of this series organic amine soaps and orthophosphate esters as the inhibitors, and using the rust-preventive oils prepared with these inhibitors added to lubricating oils, carried out seven sorts of corrosion tests and measured displacement energies in the interfaces between steel and oil and water.
For the preparation of organic amine soaps, six kinds of amines, i.e. coconut amine, oleyl amine, oleyl imidazoline, aminopropyl tallow amine, condensed composition of oleic acid and diethylene triamine, and rosine amine were employed.
The orthophosphate esters used in the test included those three kinds of esters, i.e. mono, di, and mixed ester which were prepared by the reaction of oleyl and phosphorous pentoxide, and neutralized salts of orthophosphate esters with coconut amine were also prepared for the test.
It was found that organic amine soaps indicated as the special property of that type much better results in the sulfuric acid immersion test than any other type of rust inhibitors did; whereas in the heat stability test and the non-ferrous metal immersion test they were not proved to be effective. It must be noticed too that the discoloration of oil is frequently found on the surface of metal while the metal is in storage with this type of inhibitors applied thereon. It was found further that oleic amine soaps, such as coconut amine, oleyl amine and rosine amine, which are simple in structure, did not yield good results in the humidity cabinet test, the reaction test by potassium ferricyanide and the salt water immersion test as compared with the remaining three, and that they were inferior in their water displacement quality.
As for orthophosphate esters, the anti-corrosion properties of this type of inhibitors were indicated with fairly good effect in the humidity cabinet test and the reaction test by potassium ferricyanide, and their water displacement energies showed minus values. In the salt water immersion test also they yielded rather good results. In the sulfuric acid immersion test, the heat stability test and the non-ferrous metal immersion test, however, they showed very poor results. One of the main defects of amine phosphates is, it is to be understood, that they are prone to cause corrosion during the storage period of steel plates.

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Synthesis of aldehydesulfonates were tried by two methods as follows :
(A) Acetaldehydesulfonate (AS) was obtained by hydrolysis of an oximino-ethanesulfonate, prepared by oxidizing an alkali-solution of taurin with hydrogenperoxide in the presence of Na₂WO₄ as catalyst.
(B) Isobutylaldehydesulfonate (BS) was obtained by decomposing crotonaldehyde-sodiumbisulfite adduct with acid.
The reactions of AS with “alkene”, p-octylphenol and dodecyl amine, were performed. Also the reactions of BS with p-octylphenol and s-amyl-benzene were performed.
It was found that these products were surface active. It was observed that the flocculation of dispersed particules of CaCO₃ was accelerated by addition of the condensation product of BS with p-octylphenol.

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The aqueous solutions of the nonionic surfactants consisting of polyethenoxy ether, when aqueous solution of iodine is dropped into them, become turbid. Authors named the volumes of 0.05% aqueous solution of iodine required to produce turbidness of 5ml of 0.5% surfactants solutions to be the “Iodine Number”.
The Iodine Number and the number of mols of ethylene-oxide added in the surfactant are in a linear relation (Fig. 1).
When I and n represent the Iodine Number at 20°C and the number of mols of ethylene-oxide added in the surfactant respectively, the following relations are obtained :
in octyl-phenyl series I=-0.10n+6.2
in nonyl-phenyl series I=-0.09n+6.8
in cetyl series I=-0.18n+11.2
Negative value of coefficient n means that the Iodine Number decreases with increase of the number of mols of ethylene-oxide added. The coefficients are equivalent to Iodine Number decrease caused by every one mole addition of ethylene-oxide for a homologous surfactant series. And the coefficients in octyl-phenyl and nonyl-phenyl series are nearly equal, but in cetyl series it is about double of them.
The 2nd term of above equations is constant for each homologous series and corresponds to the Iodine Number of those whereby the number of mols of ethylene-oxide added is zero, and also it increases with the increase of lipophillic property of the hydrophobic radical in the surfactants series. Therefore, from these terms, it is considered that the lipophillic property decreases in the following order :
Cetyl radical>Nonyl-phenyl radical>Octyl-phenyl radical
Iodine Number increases rapidly with rise in temperature at titration (Fig. 2).
Iodine Number increases slowly when the surfactant's concentration decreases from 0.5% to 0.25%, and increases rapidly below 0.25% (Fig. 3).
When sodium chloride is added, Iodine Number increases at first, but decreases when the salt is added further beyond a maximum point (Fig. 4).
In order to determine hydrophile-lipophile-balance (HLB), water number method, dimethyl-formamide method and phenol titration method are practically used at present. But in these method it is difficult to determine HLB of compounds to which higher number of mols of ethylene-oxide have been added, because these method will result to be almost the same constant for those compounds. This Iodine Number method, however, takes an advantage that it enables clear determination for HLB of higher mole adduct of ethylene-oxide by using the linear relaction between I and n.
As different lipophillic radical shows different tendency, it can be utilized for the distinction of the structure of surfactants.

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A method for quantitative determination of anionics and nonionics, especially of low HLB values, in vinyl emulsions was investigated with polystyrene or polymethyl methacrylate emulsions. After extraction of surfactants in hot methanol, anionics could be determined by “Methylene Blue Partition Backtitration Method”, and nonionics by precipitation in hydrochloric acid solution with phosphotungstic acid and barium chloride, after sorption of anionics and initiator decomposition products on anion exchange resin. Further, it was found that the quantities of nonionics in vinyl emulsions could be estimated nearly equal with those used for synthesizing the emulsions initially. This result may be attributed to the fact that the chain transfer constant for nonionics is too small to be diminished by chain transfer reaction during radical polymerization.

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From the analytical data of commercial polyoxyethylene (POE) sorbitan fatty acid esters, Tweens (ATLAS POWDER Co., USA), author studied the constitutions of sorbitan fatty acid esters used as raw material and amount of ethyleneoxide (EO) added.
Based on these results, various POE sorbitan fatty acid esters were synthesized. Addition-polymerization of EO was performed in an autoclave, whereby reaction temperature was optimum at about 130140°C. As the catalyst of polymerization, CH₃ONa, remained in the raw sorbitan fatty acid esters as the catalyst of esterification, was satisfactory without further addition of new catalyst.
Analytical figures of sorbitan fatty acid esters used as the raw material and amount of EO added (expressed as “times by weight” of raw sorbitan fatty acid esters) were as follows : sorbitan monolaurate with saponification value (S.V.) 160 and hydroxyl value (OH.V.) 360 as the analytical result, 2.5 times of EO; sorbitan monopalmitate (S.V. 150, OH.V. 270), 2.1 times EO; sorbitan monostearate (S.V. 145150, OH.V. 260270), 2.1 and 0.5 times EO; sorbitan tristearate (S.V. 175180, OH.V. 90100), equal weight of EO; sorbitan monooleate (S.V. 150, OH.V. 220230), 2.2 and 0.5 times of EO; sorbitan trioleate (S.V. 175180, OH.V. 80), equal weight of EO. Reaction products obtained were nearly equal to the analytical data of Tween 20, 40, 60, 61, 65, 80, 81 and 85 respectively.

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We have examined the activity of the pilled copper-chromium-manganese oxide catalyst which was made by the ordinary pilling machine from the copper-chromium-manganese oxide powder (improved Adkin's type catalyst) mixed with a small amount of water glass, for the hydrogenation of nitrobenzene to aniline in the vapor phase.
As the results, we have found that nitrobenzene has been easily hydrogenated to aniline in almost quantitative yields.
The optimum hydrogenation conditions are as follows; reaction temperature : 200300°C, liquid space velocity of nitrobenzene to the volume of catalyst (L.H.S.V.) : 0.6, the mol ratio of nitrobenzene to hydrogen is 1 : 2030.
But we have observed that at the higher reaction temperature (about 300°C) very small amount of unidentified by-products have been produced during the hydrogenation of nitrobenzene.

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Synthesis of fatty acid chlorides with dimethylformamide (I), phosphorous oxychloride (II) and fatty acids (III) such as palmitic, stearic and lauric acid were studied.
The reaction seems to contain two steps; at the beginning one mol of (III) reacts with one mol of (I) and (II) to form acid chloride and intermediate, then the intermediate combines another mol of (III) to produces another acid chloride.
The optimum conditions, considered economical, were about 0.5mol of (I) and 0.7mol of (II) to a mol of (III), the reaction temperature being a few degrees above the melting point of fatty acids with reaction time of one hour.
It is economically advantageous to use the lower layer produced at the end of the reaction for the next run.
The fatty acid chlorides produced by this procedure contain less than 1% of free fatty acids and very small quantity of phosphorous compounds. The quality of alkyl ketene dimer synthesized from fatty acid chloride produced by this procedure was identical to that from distilled fatty acid chloride.

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