Zur katalytischen Umesterung fetter Oele durch alkoholische Kalilauge

Kurz, Hans

doi:10.1002/lipi.19370440405

Cited by 29 publications

(4 citation statements)

References 1 publication

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“…Attempts to prepare methyl esters by reaction of metallic soaps (Ca, Pb, Ag) with methyl iodide or dimethyl sulphate resulted in low yields or incomplete methylation. Direct methanolysis of castor oil either with alkaline (26,44) or acidic (4) catalysts occurred to the extent of 90% as determined by the estimation of the separated glycerol, thus the product contained about 10% of unconverted glycerides. Similarly the methyl esters were contaminated with unconverted glycerides when the procedure of Young and Craig (45) was tried.…”

Section: Methodsmentioning

confidence: 99%

Studies on castor oil. I. Fatty acid composition of castor oil

Sreenivasan

Kamath

Kane

1956

J Americ Oil Chem Soc

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Summary Methyl esters of castor oil were prepared by saponifying the oil with potassium hydroxide in methanol, splitting the potassium soapsin situ with an excess of hydrochloric acid, and esterifying at room temperature. The esters had hydroxyl values comparable with those of the parent oils. The methyl esters were quantitatively resolved into hydroxy and nonhydroxy esters after reacting with succinic anhydride in toluene. The composition of castor oil was calculated from a) amount of nonhydroxy esters, b) methyl linoleate content of methyl esters determined spectro‐photometrically, c) iodine value of the methyl esters determined by the Wijs method at 15–20°C., and d) iodine value of the nonhydroxy esters determined by the Woburn method. This composition was confirmed by the estimation of saturated acids in one sample and dihydroxystearic acid in all. Castor oil was readly hydrogenated with Raney nickel in alcohol at room temperature (30–33°C.) without any hydrogenolysis of the hydroxyl groups. Methyl dihydroxystearate content of the methyl esters of this hydrogenated oil was determined by reaction with 80–100% excess periodic acid at 15–20°C.

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Section: Methodsmentioning

confidence: 99%

Studies on castor oil. I. Fatty acid composition of castor oil

Sreenivasan

Kamath

Kane

1956

J Americ Oil Chem Soc

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“…7, curve A. The fat is olive oil, the methyl esters being prepared by the inter-esterification technique (Kurz, 1937). The unmodified esters (8 mg.) consist of a mixture of at least fourteen components.…”

Section: Some Applicatios Of the Techniquementioning

confidence: 99%

“…Siliconerubber gaskets must be used on the columns at 1970 instead of natural rubber. The methyl esters of the acids present in olive oil were obtained by inter-esterification in ethyl ether with methanol in the presence of KOH as described by Kurz (1937).…”

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confidence: 99%

Gas–liquid chromatography: the separation and identification of the methyl esters of saturated and unsaturated acids from formic acid to n-octadecanoic acid

James

Martin

1956

Biochemical Journal

345

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“…Several investigators (4,6,9), employing conditions o t h e r than those described above, have f o u n d that when alcohol, fat, and alkali are allowed to interact, the aeetyl value of the fatty portion obtainable from such a mixture increases to a m a x i m m n value and then decreases with time; and there is agreenlent as to the different types of compom~ds to be f o u n d in a reacting' mixture. It has been claimed by Toyama and Tsuchiya (11) t h a t the a c e t y l value o f the reac- tion p r o d u c t is independent of the extent of alcoholysis.…”

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confidence: 99%

Modification of vegetable oils. VII. Alkali catalyzed interesterification of peanut oil with ethanol

Feuge

Gros

1949

J Americ Oil Chem Soc

113

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T H E alkali-catalyzed displacement of the glycerol in a fat b y methanol or ethanol is a n import a n t reaction in fat and oil technology. Besides producing monoesters f o r use as such, the reaction simplifies the manufacture of some soaps, especially anhydrous soaps (2, 3); a n d it is valuable in conjunction with processes f o r fraetionating fatty acids. Potentially the reaction is important in producing mono-a n d diglyeerides of unsaturated acids, and it presents interesting possibilities in the field o f "tailor-made" f a t s .In a typical large-scale operation alcoholysis (the type of interesterification u n d e r discussion) is carried out in a n open kettle b y mixing substantially n e u t r a l fat with approximately 1.6 equivalents of anhydrous methanol or ethanol in which has been dissolved a fraction of 1% (on a n oil basis) o f sodium o r potassium hydroxide. Mixing is discontinued when the solutions become homogeneous. A f t e r standing a n hour or two a t 80°C. the free glycerol which has separated and settled to the b o t t o m of the t a n k is withdrawn, and the monoesters are purified by washing with water. The alcoholysis reaction as described above has been discussed in several publications; however, a n u m b e r of interesting questions have been left unanswered, and some of the conclusions reported are a t variance with those reached by the present authors. Toyama a n d co-workers (10) f o u n d t h a t the reaction rate of alcoholysis increases with temperature, b u t no quantitative data were offered to indicate the extent of this acceleration o r its effect on the composition o f the reaction product. W r i g h t , et al. (14), investig a t e d the ethanolysis of cottonseed a n d coconut oil with the idea of establishing the effeet of the variables, ethanol, water, and alkali, on the yield of glycerol Their primary interest was to show exactly how various amounts o f w a t e r lowered the glycerol yield and how excess sodium hydroxide and/0r alcohol compensated in some measure f o r the presence o f water. They did not report reaction times and temp e r a t u r e s ; and, like Toyama and co-workers, stated the reactions were complete in a n hour o r two. Bradshaw (2) described the process of alcoholysis in connection with the preparation of soaps and recovery o f glycerol b u t presented very little experimental d a t a .Several investigators (4, 6, 9), employing conditions o t h e r than those described above, have f o u n d that when alcohol, fat, and alkali are allowed to interact, the aeetyl value of the fatty portion obtainable from such a mixture increases to a m a x i m m n value and then decreases with time; and there is agreenlent as to the different types of compom~ds to be f o u n d in a reacting' mixture. It has been claimed by Toyama and Tsuchiya (11) t h a t the a c e t y l value o f the reac-

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Zur katalytischen Umesterung fetter Oele durch alkoholische Kalilauge

Cited by 29 publications

References 1 publication

Studies on castor oil. I. Fatty acid composition of castor oil

Studies on castor oil. I. Fatty acid composition of castor oil

Gas–liquid chromatography: the separation and identification of the methyl esters of saturated and unsaturated acids from formic acid to n-octadecanoic acid

Modification of vegetable oils. VII. Alkali catalyzed interesterification of peanut oil with ethanol

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