Octanols manufacture

Beckmann rearrangement of cvc7ohexanone oxime. M.p. 68-70 C, b.p. I39 C/12 mm. On healing it gives polyamides. Used in the manufacture of Nylon[6]. Cyclohexanone oxime is formed from cyclohexane and niirosyl chloride. U.S. production 1978 410 000 tonnes, capryl alcohol See 2-octanol. caiH Uc acid See oclanoic acid. 

Most manufacturers sell a portion of their alcohol product on the merchant market, retaining a portion for internal use, typically for the manufacture of plasticizers. Sterling Chemicals linear alcohol of 7, 9, and 11 carbons is all used captively. Plasticizer range linear alcohols derived from natural fats and oils, for instance, octanol and decanol derived from coconut oil and 2-octanol derived from castor oil, are of only minor importance in the marketplace. 

The by-product of this process, pelargonic acid [112-05-0] is also an item of commerce. The usual source of sebacic acid [111-20-6] for nylon-6,10 [9008-66-6] is also from a natural product, ticinoleic acid [141-22-0] (12-hydroxyoleic acid), isolated from castor oil [8001-79-4]. The acid reacts with excess sodium or potassium hydroxide at high temperatures (250—275°C) to produce sebacic acid and 2-octanol [123-96-6] (166) by cleavage at the 9,10-unsaturated position. The manufacture of dodecanedioic acid [693-23-2] for nylon-6,12 begins with the catalytic trimerization of butadiene to make cyclododecatriene [4904-61-4] followed by reduction to cyclododecane [294-62-2] (see Butadiene). The cyclododecane is oxidatively cleaved to dodecanedioic acid in a process similar to that used in adipic acid production. 

Alkali Fusion. Tha alkaU fusion of castor oil using sodium or potassium hydroxide in the presence of catalysts to spHt the ricinoleate molecule, results in two different products depending on reaction conditions (37,38). At lower (180—200°C) reaction temperatures using one mole of alkah, methylhexyl ketone and 10-hydroxydecanoic acid are prepared. The 10-hydroxydecanoic acid is formed in good yield when either castor oil or methyl ricinoleate [141-24-2] is fused in the presence of a high boiling unhindered primary or secondary alcohol such as 1- or 2-octanol. An increase to two moles of alkali/mole ricinoleate and a temperature of 250—275°C produces capryl alcohol [123-96-6] CgH gO, and sebacic acid [111-20-6] C QH gO, (39—41). Sebacic acid is used in the manufacture of nylon-6,10. 

Several manufacturers introduced products amenable for this solid-supported LLE and for supported liquid extraction (SLE). The most common support material is high-purity diatomaceous earth. Table 1.8 lists some commercial products and their suppliers. The most widely investigated membrane-based format is the supported liquid membrane (SLM) on a polymeric (usually polypropylene) porous hollow fiber. The tubular polypropylene fiber (short length, 5 to 10 cm) is dipped into an organic solvent such as nitrophenyl octylether or 1-octanol so that the liquid diffuses into the pores on the fiber wall. This liquid serves as the extraction solvent when the coated fiber is dipped... 

Isophorone has a water solubility of 12,000 ppm, a log octanol/water partition coefficient of 1.67, a Henry s Law constant of 4.55 X 10 atm m mof, a vapor pressure of 0.3 mm Hg at 20 C, a log sediment sorption coefficient of approximately 1.46, and a log bioconcentration factor (BCF) of 0.85. Isophorone is released to air and water from its manufacturing and use. Based on its water solubility, some isophorone may wash out of the atmosphere however, only limited amounts will be washed out because of the short atmospheric half-life of isophorone. Particularly during the day, when hydroxyl radical (HO) concentrations are highest, very little atmospheric transport will occur due to its fast reaction with HO. ... 

Once mycelia have been separated via continuous filtration from exhausted production media, citric acid may be recovered by using three different methods, such as direct crystallization upon concentration of the filtered liquor, precipitation as calcium citrate tetrahydrate, or liquid extraction. Since molasses are extremely rich in impurities, direct crystallization cannot be applied unless very refined raw materials, such as sucrose syrups or crystals, are used. The precipitation process (that is based on subsequent addition of sulfuric acid and lime to clarified fermentation broths) is used by the great majority of world citric acid manufacturers, including Archer Daniels Midland Co. (ADM) in the United States. Liquid extraction with mixtures of trilaurylamine, n-octanol, and Cio or Cn isoparaffin was used by Pfizer Inc. in Europe and Bayer Co. (formerly Haarmann Reimer Co., subsidiary of Miles) in the Dayton (OH, USA) and Eikhart (IN, USA) plants only (Moresi and Parente, 1999), even if such plants might have been shut down in 1998. 

During the early forties flexible PVC use was mainly limited to military applications, including wire and cable, and various film and sheeting applications, etc. With the conclusion of World War II, new markets for PVC developed rapidly. Aside from DOP, which was commercialized in 1940(4), dicapryl phthalate (DCP) was introduced by Rohm and Haas C5), also in the early forties. With the development of plastisols(6), DCP became a plasticizer of choice because of the favorable balance of properties it imparted — especially low viscosity. However, DCP s subsequent growth has been limited since capryl alcohol (octanol-2), a monohydric secondary alcohol, is a by-product of limited volume sebacic acid manufacture. 

Polychlorinated biphenyls (PCBs) were manufactured as a liquid transformer oil. Due to leakage, PCBs are now found throughout the environment, and this long-lived chemical represents a health hazard. PCBs have been found to be present in the St. Lawrence River at concentrations of about 0.3 ppb (parts per billion by weight). Estimate the likely concentration ot PCBs in fish in this river. The average octanol-water partition coefficient for PCBs is... 

An especially valuable physicochemical property for chemical assessment is the octanol/water partition coefficient, usually expressed on a logarithmic scale (log Kow). This property correlates with partitioning from water to soil and sediment, as well as bioaccumulation in fish and other aquatic organisms. The ability to estimate log Kow from chemical structure provides a powerful tool to developers of new chemicals to model environmental partitioning and bioaccumulation prior to manufacture or even chemical synthesis (18). Log Kow... 

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