By the oxo process

The 13—carbon tridecyl alcohol is usually considered to be a plasticizer range alcohol because of its manufacture by the oxo process and its use in making plasticizers. On the other hand, some types of linear 9- and 11-carbon alcohols find major appHcation in detergents. 

Lighter C —Cg a-olefias and Cg branched olefins are converted by the oxo process into fatty acids containing one carbon number greater than the starting a-olefin. These fatty acids are then used to produce alkenylhen enesulfonic acid products which are used ia the United States and ia Europe as perborate bleach activators ia heavy-duty laundry detergents. 

Hiadered esters are also produced from and Cg a-olefias. These olefias are coaverted iato C —C fatty acids by the oxo process the acids are thea treated with polyols such as peataerythritol and trimethylol propane to produce hindered esters, which find use ia lubricants for jet engines and other high performance appHcations. 

Union Carbide Chemicals and Plastics Company Inc. is the only producer of C-5 oxo derived alcohols (148,150) in the United States. About 75% of the 30,000 t of valeraldehyde and 2-methylbutyraldehyde produced by the oxo process was converted to the isomeric mixture of primary amyl alcohols in 1988 (150). The primary amyl alcohol mixture was available in tank car quantities for 1.02/kg in 1991. The Dow Chemical Company appears to have stopped commercial production of / fZ-amyl alcohol (151). 

The demand for amyl alcohols is expected to remain unchanged until 1993. Competition from other alcohols and limited appHcations limit growth in markets for amyl alcohols. U.S. demand was predicted to grow from 29 x 10 t in 1983 to 32 x Kf t by 1990 (152). In Europe, amyl alcohols account for over 80% of the demand for valeraldehyde (17,000 t in 1984). BASE and Hoechst AG produce both / -valeraldehyde and 2-methylbutyraldehyde from butenes by the oxo process (149). The demand for C-5 in Europe is also predicted not to grow substantially (150). Amyl alcohols are growing at a much lower rate than other oxo alcohols as shown in Table 7. 

The switch from the conventional cobalt complex catalyst to a new rhodium-based catalyst represents a technical advance for producing aldehydes by olefin hydroformylation with CO, ie, by the oxo process (qv) (82). A 200 t/yr CSTR pilot plant provided scale-up data for the first industrial,... 

Unfortunately, secondary and tertiary butyl alcohols (SBA and TBA) cannot be made by the Oxo process. Instead they are produced either by indirect or direct hydration of the corresponding olefin. Normal butylene gives SBA and isobutylene gives TBA. The processes are similar to the corresponding routes to IPA. 

The alcohol used for this ester is known as Alphanol 79 and is produced by the Oxo process. It consists of mixed normal primary and a-methyl substituted primary aliphatic C7. Cs. and Cs alcohols. 

Meanwhile, lower monohydric alcohols were first made by the oxo process. These included n-propanol, n- and isobutanol and amyl alcohol. In PVC, only one of these assumed any importance -n-butanol - mainly in butyl benzyl phthalate. Dibutyl phthalate (DBP) was by this time considered too volatile for use in PVC in the U.S.(10). The so-called coesters - butyl octyl phthalate (BOP), butyl isodecyl phthalate and butyl cyclohexyl phthalate -have been on and off the market for many years but never achieved major success in the U.S. Dibutyl phthalate/DOP blends and BOP have probably been most successful in Japan. Diisobutyl phthalate is used in Brazil and other South American countries even today, because of its low cost. BOP is also offered in Europe, but as in the U.S., it has not been a major success. One reason could be the wide variability of composition from different suppliers. In fact, some BOP s were merely physical blends of DBP and DOP. 

As the decade ended, a new monohydric alcohol phthalate based on mixed C7-C9-C11 straight chain and single methyl branched alcohols was introduced by Monsanto Co. The alcohols are produced by the oxo process from straight chain alpha olefins. The phthalate competed directly with 610P, especially in the automotive upholstery market where it gained rapid acceptance. 

About 8 percent of the propylene converted into chemicals is used to make oxo alcohols such as 1-butanol and 2-ethylhexanol, which are called oxo alcohols because they are derived from olefins by the oxo process, which converts them to aldehydes. (The oxo process was described earlier in this chapter.)... 

The /z-butyraldeliyde may be obtained from acetaldehyde [75-07-0] by aldol addition followed by hydrogenation, or from propylene by the oxo process. This latter process is predominantly favored (Fig. 7). 

The largest use of industrial hydrogen is in ammonia synthesis, in the catalytic hydrogenation of unsaturated liquid vegetable oils to solid, edible fats (margarine), and in the manufacture of bulk organic chemicals, particularly methanol, by the Oxo Process using a cobalt catalyst ... 

Derivation Reduction of coconut-oil fatty acids, from C9olefin and synthesis gas, by the Oxo process. 

CAS 27554-26-3. (C8H17COO)2C6H4. Isomeric esters obtained from phthalic anhydride and the mixed octyl alcohols made by the Oxo process. Properties Nearly colorless, viscous liquid mild odor. Bp 370C, d 0.980-0.983 (20/20C), bulk d 8.20 lb/gal (20C), flash p 450F (232C). Insoluble in water compatible with vinyl chloride resins and some cellulosic resins. Combustible. 

Derivation (1) By reduction of ethyl caproate, (2) from olefins by the Oxo process. 

CAS 26952-21-6. General term applied to any isomer of the formula C7H15CH2OH in which the eight carbon atoms form a branched chain. Usually refers to a mixture of isomers made by the Oxo process. A selected C7 hydrocarbon fraction is reacted with hydrogen and carbon monoxide in the presence of a catalyst at pressures up to 3000 psi. The crude alcohol is recovered and purified. 

Acyclic ketones from hydrocarbons this includes ketones prepared by the Oxo process... 

The Wacker process, the oxidation of ethylene to acetaldehyde, lost its original importance over the past 30 years. While at the beginning more than 40 factories with a total capacity of more than 2 million tons of acetaldehyde per year were installed, acetaldehyde as an industrial intermediate was replaced successively by other processes. For example, compounds such as butyraldehyde/butanol are produced by the oxo process from propylene, and acetic acid by the Monsanto process from methanol and CO or by direct oxidation of ethane. The way via acetaldehyde to these products is dependent on the price of ethylene. Petrochemical ethylene from cracking processes became considerably more expensive during these years. Thus, only few factories would be necessary to meet the demand for other derivatives of acetaldehyde such as alkyl amines, pyridines, glyoxal, and pentaerythritol. 

Other alcohols, produced predominantly by the Oxo-process, can be esterified by this method using phthalic anhydride. 

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