Blubber Oil Research Articles

(37)抹香鯨皮油の高壓還元による高級アルコールの製造

(37)抹香鯨皮油の高壓還元による高級アルコールの製造

The use of low ‐ temperature crystallization in the determination of component acids of liquid fats. IV. Marine animal oils. The component acids and glycerides of a grey (atlantic) seal

AbstractPreliminary crystallization of the mixed fatty acids of marine animal oils from acetone at —60°, followed by ether at —30° or —40°, resolves them into groups, differing widely in unsaturation, which can then be esterified and fractionally distilled. This procedure has great advantages compared with the lithium and lead salt separations which were previously employed. The method has been applied to the component acids, and also to the component glycerides, of the blubber oil of a grey seal (Halichoerus grypus). The composition of the fatty acids of seal blubber oil varies over a somewhat wider range than obtains in the fatty oils of some other marine species. The glycerides belong to the extremely ‘“mixed” type characteristic of marine animal oils. The seal liver contained less than 3% of lipids, which consisted of 29%’ phosphatides, 21% unsaponifiable matter and 50% glycerides 5 the liver glycerides contained a less unsaturated mixture of fatty acids than the blubber glycerides and also a higher content of saturated fatty acids.

鯨油の性状

Physical properties, such as colour, specific gravity, viscosity and refractive index, as well as chemical properties, such as acid, saponification and iodine values, contents of unsaponified matter, and that of various fatty acids were determined with whale oils:-Blubber. head and bone oil of Physeter maerocephalus, blubber and tangue oil of Balaenoptera borealis, and blubber oil of Hyperaodon rostratum.

Eicosanol and Eicosenol in Sperm Blubber Oil

Eicosanol and Eicosenol in Sperm Blubber Oil

Researches on Unsaponifiable Matters in Sperm Blubber Oil

(1) 抹香鯨皮油不鹸化物中に飽和及不飽和アルコール,第三級アルコール炭化水素混合エーテルの存在を知れり.(2) 飽和アルコールC8のSpermyl alcoholはOctanol (1), C10のCachalotyl alcoholはDecanol (1), C12なるCatodontidaeyl alcoholはLauryl alcoholに一致し, Catodontidaeyl alcoholの異性體と思はるるIsocatodontidaeyl alcoholの存在を認めたり.(3) 不飽和アルコールはC8のAgorophyl alcohol, C10のMacrocephalyl alcohol, C12のOdontocetyl alcohol並にUndecen-(2)-ol-(1)を含む.(4) 第三級アルコールは不飽和アルコールにして臭化物は相當臭素含量多く脱臭素によりて新炭化水素を生ず.(5) 抹香鯨エーテルは第三級アルコールに混入し芳香を有し混合不飽和エーテルなり.(6) 多量の炭化水素を含有す.當研究に際し4-Iodo-biphenylyl-4-isocyanateの製法使用に川合博士の御好意並に實驗上終始助力せられし米勢千鶴男氏に深謝の意を表す.

THE HIGHLY UNSATURATED ALCOHOLS IN SPERM BLUBBER OIL

Abstract The high boiling fraction of the unsaponifiable matter of sperm blubber oil was brominated in ethereal solution, and the ether insoluble bromide was separated and then debrominated to regenerate the highly unsaturated alcohols. These were converted into acetates, and the latter were fractionated. An examination of the resulting fractions showed that the highly unsaturated alcohols of sperm blubber oil contained two individual alcohols C20H34O and C22H36O as chief components.

TETRADECENOIC AND DODECENOIC ACIDS IN SPERM OIL. I. TETRADECENOIC AND DODECENOIC ACIDS IN SPERM BLUBBER OIL

Abstract Tetradecenoic acid C14H26O2 and dodecenoic acid C12H22O2 have been separated from sperm blubber oil. They are converted into dihydroxymyristic acid C14H28O4 and dihydroxylauric acid C12H24O4 respectively, and the methyl esters of these hydroxy-derivatives are subjected to the permanganate oxidation in acetone. From the results of an examination of the oxidation products, the following constitutions have been established: Tetradecenoic acid CH3·(CH2)7·CH=CH·(CH2)3·COOH, Dodecenoic acid CH3·(CH2)5·CH=CH·(CH2)3·COOH. It is thus seen that tetradecenoic acid in sperm blubber oil is identical with physeteric acid (Δ5:6-tetradecenoic acid) in sperm head oil, whilst dodecenoic acid in sperm blubber oil, to which the name denticetic acid is assigned, is Δ5:6-acid and is an isomer of linderic acid (Δ4:5-dodecenoic acid) in the seed oil of Lindera obtusiloba.

HEXADECENOL IN SPERM BLUBBER OIL

Abstract Hexadecenol has been separated, in a very small yield, from the unsaponifiable matter of sperm blubber oil, and its constitution has been established as CH3·(CH2)5·CH=CH·(CH2)7·CH2OH. Hence, hexadecenol in sperm blubber oil is proved to be identical with zoomaryl alcohol (Δ9:10-hexadecenol) previously found in sperm head oil.

TETRADECENOIC AND DODECENOIC ACIDS IN SPERM OIL. II. DODECENOIC ACID IN SPERM HEAD OIL

Abstract Dodecenoic acid C12H22O2 has been isolated from sperm head oil, and methyl dihydroxylaurate C13H26O4 prepared from it has been subjected to permanganate oxidation in acetone. On examining the oxidation products the constitution of dodecenoic acid has been proved to be CH3·(CH2)5·CH=CH·(CH2)3·COOH. It is thus seen that dodecenoic acid in sperm head oil is identical with denticetic acid (Δ5:6-dodecenoic acid) in sperm blubber oil described in the preceding paper.

The Highly Unsaturated Alcohols in Sperm Blubber Oil

The high boiling fraction of the unsaponifiable matter of sperm blubber oil was brominated in ethereal solution, and the ether insoluble bromide was separated and then debrominated to regenerate the highly unsaturated alcohols. These were converted into acetates, and the latter were fractionated. An examination of the resulting fractions showed that the highly unsaturated alcohols of sperm blubber oil contained two individual alcohols C20H34O and C22H36O as chief components.

製革工業と魚油及海獸油

製革工業と魚油及海獸油