n-HEPTYL ALCOHOL

1926 ◽  
Vol 6 ◽  
pp. 52 ◽  
Keyword(s):  
Heptyl Alcohol

Facile synthesis of amino bicyclo[2.2.1]heptyl alcohol and its application for enantioselective additions of diethylzinc to aldehydes

2000 ◽  
Vol 41 (23) ◽  
pp. 4587-4590 ◽  
Author(s):  
Naoto Hanyu ◽  
Takashi Mino ◽  
Masami Sakamoto ◽  
Tsutomu Fujita
Keyword(s):  
Facile Synthesis ◽  
Heptyl Alcohol

V. On the constitution of capryl alcohol from castor-oil

1868 ◽  
Vol 16 ◽  
pp. 376-381
Keyword(s):  
Boiling Point ◽  
Castor Oil ◽  
Cold Water ◽  
Fractional Distillation ◽  
Oxidation Products ◽  
Acid Reaction ◽  
Concentrated Solution ◽  
Characteristic Odour ◽  
Oily Liquid ◽  
Heptyl Alcohol

There is perhaps no other compound known which has been so often and so fully investigated by different chemists, and yet whose constitution is clouded in so much obscurity, as the alcohol which is obtained by distilling castor-oil soap with caustic alkalies. From the time of its discovery until recently, this compound has been alternately considered by one investigator to be capryl or octyl alcohol, and by another to consist of œnanthyl or heptyl alcohol. As a proof that it is capryl alcohol, Bouis states that, by the moderate action of nitric acid, a small quantity of caprylic acid is produced, the greater part of the alcohol, however, being oxidized to lower members of the fatty acid series; and Kolbe concludes, from the formation of these acids, that it is a secondary or isoalcohol, probably methyl-hextl carbinol, C { CH 3 C 6 H 13 H OH. As I shall show in this paper, Kolbe’s view is correct; by moderate oxidation, the alcohol loses two atoms of hydrogen, and is converted into the corresponding acetone, methyl œnanthol, the same compound which is generally obtained as a byeproduct in the preparation of the alcohol. The alcohol which I used was prepared by distilling a mixture of castor-oil soap and caustic soda in a flask of thin copper-sheeting as quickly as possible. The distillate was repeatedly rectified over fused caustic potash, the portion boiling below 200° C. only being collected. The alcohol was isolated from this liquid by fractional distillation; its corrected boiling-point was 181° C. The portions having a lower boiling-point consist of hydrocarbons, which combine with bromine, probably members of the olefine series, amongst which octylene, boiling at 125° C., preponderates. A considerable quantity of liquid distilled above 160°, the boiling-point remaining somewhat constant at 170° C. Neither this fraction nor any other distillate contained an acetone, as none combined with hydrogen-sodium sulphite. According to Chapman, the liquid boiling at 170° consists chiefly of heptyl alcohol. In order to isolate this alcohol, I acted upon the liquid boiling between 160°-175° with iodine and phosphorus. The product, subjected to fractional distillation, was found to consist of isoctyl iodide, boiling at 210°-215°, and of hydrocarbons, distilling below 160°; the portion which came over between 160° and 210° was very small, and diminished after each further distillation. This shows that no heptyl alcohol was present, and that the original liquid boiling at 170° was a mixture of isoctyl alcohol and hydrocarbons, which could not be separated by simple fractioning. To obtain the oxidation products of isoctyl alcohol, I acted upon it with a solution consisting of 3 parts of sulphuric acid, 2 parts of potassium bichromate, and 10 parts of water, the reaction being moderated by surrounding the vessel with cold water. As soon as no further action was observed, the liquid was distilled. The distillate consisted of an aqueous liquid, which had a slight acid reaction, and a light oily fluid; it was neutralized with sodium carbonate, and the oil treated again with the oxidizing mixture, which, however, had hardly any action upon it m the cold. This oily liquid is methyl œnauthol; it has the characteristic odour of that compound, and when shaken with a concentrated solution of hydrogensodium sulphite, solidifies to a mass of pearly white crystals. These were dried between blotting-paper, and decomposed by a dilute solution of cans soda. The oil which separated was dried over calcium chloride; it distilled completely between 170°-172°, the boiling-point of methyl œnantnol being 171°.

n-Heptyl Alcohol

2003 ◽  
pp. 52-52
Author(s):  
H. T. Clarke ◽  
E. E. Dreger
Keyword(s):  
Heptyl Alcohol

scholarly journals X. Normal primary heptyl alcohol

1873 ◽  
Vol 21 (139-147) ◽  
pp. 393-394
Keyword(s):  
Acetic Acid ◽  
Castor Oil ◽  
Starting Point ◽  
Normal Acid ◽  
Heptyl Alcohol

One of us has shown that by oxidizing the primary heptyl alcohol from normal heptane acid is formed, which is identical with acid from œnanthol. Œnanthylic acid is therefore a normal acid; and as by the distillation of castor-oil any quantity of œnanthol may be obtained, this aldehyde appears to be the best starting-point for the preparation of the hitherto almost unknown normal heptyl compounds. Some years ago Bouis and Carlet found that, by the action of zinc and acetic acid on œnanthol, a heptyl acetate is formed, which yielded a heptyl alcohol boiling at 165°.

scholarly journals XLIII.—Oenanthylic acid and normal heptyl alcohol

1873 ◽  
Vol 26 (0) ◽  
pp. 1073-1082
Author(s):  
Harry Grimshaw ◽  
Carl Schorlemmer
Keyword(s):  
Heptyl Alcohol

scholarly journals I. On the normal paraffins

1878 ◽  
Vol 26 (179-184) ◽  
pp. 325-326
Keyword(s):  
Acetic Acid ◽  
General Formula ◽  
Butyric Acid ◽  
Normal Paraffin ◽  
Boiling Points ◽  
First Results ◽  
Normal Hexane ◽  
Heptyl Alcohol ◽  
Bromine Vapour

In the first paper of this subject it was shown that by the action of chlorine on a normal paraffin a primary chloride and a secondary one of the general formula C n H 2n+1 CH 3 } CHCL are formed simultaneously. It appeared of interest also to examine the action of bromine on the paraffins. The present paper contains the first results of this research. I. Normal Hexane.—When bromine vapour is passed into the vapour of the boiling hydrocarbon, in the daylight, its colour disappears quickly and substitution products are formed which are partly decomposed by distillation. The portion distilling without decomposition consists of a hexyl bromide, which was converted into the acetate and the alcohol. The latter yielded on oxidation acetic acid and normal butyric acid , showing that it is methylbutyl carbinol . The boiling-points of the different compounds are as follows:— The heptyl alcohol is methylpentyl carbinol , because on oxidation it was resolved into acetic acid and normal pentylic acid .

scholarly journals II. Note on the amyl-compounds derived from petroleum

1867 ◽  
Vol 15 ◽  
pp. 131-132 ◽  
Keyword(s):  
Specific Gravity ◽  
Azelaic Acid ◽  
Boiling Point ◽  
Fusel Oil ◽  
Boiling Points ◽  
Heptyl Alcohol

In a former communication I have shown that the hydride of heptyl obtained from petroleum has a higher specific gravity than its isomers ethyl-amyl, and hydride of heptyl from azelaic acid. The same is the case with their derivatives, and some of these isomeric compounds also show considerable differences in their boiling-points. I could not compare the different heptyl-compounds which I prepared with those of heptyl-alcohol formed by fermentation, as the latter substance is very little known, and I therefore considered it interesting to compare the amyl-compounds from fusel-oil with those obtained from petroleum. From the latter substance I prepared a considerable quantity of pure hydride of amyl, which boiled constantly at 33°—35°C. ; and I did not succeed in lowering the boiling-point any further. From this hydride other amyl-compounds were obtained in exactly the same way as the heptyl-compounds. Pure amyl-compounds from fusel-oil were also prepared with the greatest care, and their specific gravities and boiling-points compared, under exactly the same circumstances, with the compounds prepared from petroleum. The results of this investigation are contained in the following Table:—

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