Heptyl alcohol

In a 12-1. flask fitted with a mechanical stirrer and a short reflux condenser are placed 1800 g. (32.2 moles) of iron filings (Note i), 3 1. (52.5 moles) of glacial acetic acid, 3 1. of water, and 450 g. (3.95 moles) of heptaldehyde (Note 2). The mixture is heated on the steam bath, with stirring, for six to seven hours (Note 3). The flask is then fitted to an apparatus for steam distillation (Org. Syn. 2, 80) and the mixture distilled in a current of steam (Note 4) until no more oil passes over (7-8 1. of distillate). The oil is then separated, and the aqueous part distilled to recover a small quantity of dissolved or suspended heptyl alcohol. 

The combined product is mixed with i 1. of 20 per cent sodium hydroxide solution and stirred on the steam bath for four hours, in order to hydrolyze a small proportion of heptyl acetate. The oil is then separated and distilled, and the portion boiling at 172-176° collected. The residue in the flask is mixed with about 100 cc. of water and distilled, whereupon a further small quantity of oil passes over with the steam. This distillate and the forerun are freed of the bulk of the water in a separatory funnel, and distilled from a smaller flask. In this way the total yield of -heptyl alcohol boiling at 172-176° (uncorr.) is 350-370 g. (75-81 per cent of the theoretical amount). The alcohol may be redistilled under reduced pressure, and it passes over almost without loss at 7i-72°/i2 mm. 

The Iron filings used were free of grease and ore. Ninety-five per cent of the filings passed an 8o-mesh screen and 6o per cent passed a loo-mesh screen. Grade D iron supplied by the Master Builders Company, Cleveland, Ohio, is ready for use and very satisfactory. 

The heptaldehyde should be a freshly distilled product, boiling at 154-156°. 

The reaction may be successfully carried out without a stirrer, but the time of heating must then be lengthened to twelve to fifteen hours. 

Boiling point at 76S mm Freezing point Refractive index at 20 C, n Specific gravity at 20/4 C 

HEPTYL ALCOHOL FORMS BINARY AZEOTROPES WITH  

---

Referring to Fig. IV-4, the angles a and /3 for a lens of isobutyl alcohol on water are 42.5° and 3°, respectively. The surface tension of water saturated with the alcohol is 24.5 dyn/cm the interfacial tension between the two liquids is 2.0 dyn/cm, and the surface tension of n-heptyl alcohol is 23.0 dyn/cm. Calculate the value of the angle 7 in the figure. Which equation, IV-6 or IV-9, represents these data better Calculate the thickness of an infinite lens of isobutyl alcohol on water. 

Calculate the limiting thickness of a lens of n-heptyl alcohol on water at 20°C. 

A further small quantity of n-heptyl alcohol may be obtained from the alkaline solution by mixing it with 50 ml. of water and distilling the distillate is saturated with salt, the oil separated, dried aad distilled from a small flask. 

The spectmm of oxo products ia Japan is far less diverse. Nearly 75% of Japan s total oxo capacity of 733,000 t is dedicated to the hydroformylation of propylene. 2-EH derived from -butyraldehyde is by far the dominant product. Other products iaclude linear alcohols and higher branched alcohols. Additionally, Japan is the world s principal source of branched heptyl alcohol. The three ptincipal Japanese oxo producers having slightly more than 70% of Japan s total oxo capacity are Mitsubishi Kasei, Kyowa Yuka, and Japan Oxocol. 

Pyrolytic Decomposition. The pyrolytic decomposition at 350—460°C of castor oil or the methyl ester of ricinoleic acid spHts the ricinoleate molecule at the hydroxyl group forming heptaldehyde and undecylenic acids. Heptaldehyde, used in the manufacture of synthetic flavors and fragrances (see Elavors and spices Perfumes) may also be converted to heptanoic acid by various oxidation techniques and to heptyl alcohol by catalytic hydrogenation. When heptaldehyde reacts with benzaldehyde, amyl cinnamic aldehyde is produced (see Cinnamic acid, cinnamaldehyde, and cinnamyl... 

Heptyl alcohol has been prepared by the reduction of heptaldehyde with zinc dust and acetic acid,i with sodium amalgam and acetic acid, with sodium in toluene and acetic acid, and with hydrogen and a platinum catalyst. Heptaldehyde has also been reduced biochemically by adding it to a fermenting sugar solution. Heptyl alcohol has been prepared by the reduction of heptoamide with sodium and amyl alcohol. ... 

It has been frequently noted that certain lots of iron filings are not satisfactory for the reduction of heptaldehyde to heptyl alcohol in acetic acid solution. E. E. Reld and J. R. Ruhoff have found that the addition of a solution of 20 g. of nickel cliloride hexahydrate in 50 cc. of water immediately after the addition of the aldehyde will cause the reaction to start at once and wiU greatly accelerate the rate of reaction so that it is complete in two hours instead of the usual six to seven hours. The checkers have found this to be the case even with a lot of iron which could not be made to react when reduced in hydrogen. It is also recommended that the reaction mixture be divided between two 12-I. flasks and that 3 1. of water be added to each half immediately at the end of the reaction. This prevents the mixture from setting to a hard mass in case the steam distillation is not carried out at once, and also reduces the amount of foaming. 

C7H160 HEPTYL-ALCOHOL -338.701 7.0060E-01 5.7147E-05 -124.18 362 C8H180 BUTYL-ETHER -337.796 8.1490E-01 6.4263E-05 -88.53... 

Cracking of the ester at about 500°C leads to the formation of the undecylenic acid ester together with such products as heptyl alcohol, heptanoic acid and heptaldehyde. Undecylenic acid may then be obtained by hydrolysis of the ester. Treatment of the acid by HBr in the presence of a peroxide leads to w-bromoundecanoic acid together with the 10-isomer, which is removed. Treatment of the w-bromo derivative with ammonia leads to w-aminoundecanoic acid, which has a melting point of 50°C (Figure 18.8). 

Chemical Designations - Synonyms. Enanthic alcohol 1-HeptanoI Heptyl alcohol 1-Hydroxyheptane Chemical Formula CH3(CHj)jCH20H. 

Heptyl alcohol, TsOH, benzene, reflux, 66-92% yield. ... 

One of the heptyl alcohols, methyl-amyl carbinol, of the formula... 

Of these phenyl-amyl alcohol has a pleasant, but somewhat evanescent lemon-like odour phenyl-hexyl alcohol has a very similar odour to this and phenyl-heptyl alcohol has a slight, but extremely agreeable odour [Pg.129]

METHYL-2,4-HEPTANEDIONE, 55, 127 3-Methyl-3-heptyl alcohol, 58, 78 3-Methyl-4-heptyl alcohol, 58, 78 3-Methyl-3-heptyl fluoride, 58, 78 3-Methyl4-heptyl fluoride, 58, 78 7V-(4-Methyl-2,4-hexadienoyl)pyrolidine,... 

Hemimellitic acid, b29 Heptaldehyde, h3 vec-Heptyl alcohol, hi2 Heptyl bromide, b343 Heptyl chloride cl47 Heptyl iodide, i34 Heptyl mercaptan, h8 Heptyl methyl ketone, n99... 

C soluble in water, ether, or alcohol used as a chemical Intermediate, as a solvent, and in cosmetics. Also known as heptyl alcohol. wan hep ta,n6l ( 3-heptanol orgchem CH3CH2CH(OH)C4H9Analcohol a liquid boiling at l56 C Used as a coating, solvent, and diluent, as a chemical Intermediate, and as a flotation frother. thre hep-t3,noI )... 

---