Alcohols 2-ethyl hexanol

The use of alkali metal oxide catalysts for aldol condensation reactions has been examined for the production of 2-ethylhexenal from butanal [34]. When coupled to a hydrogenation catalyst the system can produce the plasticizer alcohol 2-ethyl-hexanol directly. When isobutyraldehyde was used as the feed to a silica-supported sodium oxide catalyst, no products were formed but a significant amount of carbon was deposited on the catalyst and in the reactor (Scheme 21.2). 

Alcohol 2-ethyl hexanol Isooctyl alcohol Nonyl alcohol Hexadecyl alcohol... 

An example with huge economic relevance is the manufacture of 2-propyl-heptanol (2-PH) as a component of plasticizer alcohols and, on a smaller scale, for use in cosmetics [9]. On an industrial scale, the transformation is commonly conducted as a three-step approach starting with the hydroformylation of isomeric butenes, subsequent aldol reaction of formed -valeraldehyde, and, finally, combined hydrogenation of the C-C double bond and aldehyde group [10]. In a similar process, the production of the plasticizer alcohol 2-ethyl-hexanol (2-EH) is carried out [11, 12]. 

OCTYL ALCOHOL - ETHYL HEXANOL - Additive in absorption machines to reduce surface tension in the absorber. 

Properties Gardner 5+ (50% solids in toluene) solid, flakes sol. in aliphatic and aromatic hydrocarbons, long-chain alcohols (ethyl-hexanol), ethylene dichloride, MIBK, and trichloroethylene m.w. 1650 dens. 0.97 kg/l vise. 360 cps (70% solids in toluene) soften, pt. (R B) 100 C acid no. < 1 sapon. no. < 1 flash pt. (COC) 249 C Piccotac 1100 [Eastman]... 

There are many other commercial alcohols besides methanol. This chapter treats the ones traded in the largest volumes ethyl alcohol, isopropyl alcohol (IPA), normal butyl alcohol (NBA), 2-ethyl hexanol (2-EH) and li4-butanediol (BDO). 

Ethyl hexanol, sometimes called 2-ethyl hexyl alcohol, 2-ethyl hex, or more simply 2-EH, is one of the oldest high molecular weight aliphatic alcohols. What does it have in common with NBA Both are made from propylene via the Oxo process, and both have the same aldehyde intermediate— normal butyraldehyde. 

The major commercial acrylates are formed from the alcohols that should by now be familiar to you—methanol, ethanol, butanol, iso-butanol, and 2-ethyl hexanol. The corresponding acrylates are shown in Table 19—1. 

The process to make 2-ethyl hexanol starts with propylene and synthesis gas, but it takes dimerization and hydrogenation to form the proper carbon chain and alcohol group, -OH. 

ETHYL HEXANOL 2-Ethyl- 1-Hexanol, 2-Ethylhexyl Alcohol Combustible Liquid 2 2 0... 

Ethyl acrylate (inhibited) (14) Ethyl acrylate (inhibited) (14) Ethyl acrylate (inhibited) (14) Ethyl alcohol (6) Ethylenediamine (4) Ethylene glycol (6) 2-Ethyl hexanol (6) Voranol CP 4100 (6) Methyl methacrylate (inhibited) (14) Dioctyl phthalate (13)... 

The following solvents are now manufactured on the large scale for industrial purposes ethylene dichloride, di-, tri-, and tetra-chloroethy-lene, tetrachloroethane, dichloroethyl ether, hexahydrobenzene, cyclo-hexanol, tetra- and deca-hydronaphthalene (tetralin and dekalin), triacetin, ethylene glycol, butyl alcohol, diacetone alcohol, ethyl lactate, isopropyl ether, etc. 

This case study investigates the possibility of applying reactive distillation to the synthesis of fatty-acid esters as a generic multiproduct process. As representative species we consider the lauric (dodecanoic) acid and some alcohols the series Q-C8, such as methanol, n-propanol and 2-ethyl-hexanol (isooctanol). The generic reversible chemical reaction is ... 

This section deals with the conceptual design of a catalytic distillation process for the esterification of lauric acid (LA) with 2-ethyl-hexanol (2EtH). Laboratory experiments showed that a superacid sulfated zirconia catalyst exhibits good activity over a large interval, from 130 to 180 °C with no ether formation. On the contrary, the catalyst is sensitive to the presence of free liquid water. Raw materials are lauric acid and 2-ethylhexyl alcohol of high purity. The conversion should be over 99.9%, because the product is aimed at cosmetic applications. 

Further improvement in the technology of methyl fatty ester synthesis can be achieved by dual esterification [4], This takes advantage of the fact that the sulfated zirconia catalyst has similar activity for normal alcohols, over the series C1-C8. However, methanol manifests about twice the activity [20], The removal of water produced by the esterification with methanol is solved simply, by employing a heavy alcohol immiscible with water, such as 2-ethyl-hexanol, which acts simultaneously as a reactant and an entrainer. As a result, the two fatty esters are obtained in the bottom product in the desired ratio by adjusting the feeds. For example, in a preferable operation mode the ratio of fresh feed reactants is acid methanol 2-ethyl-hexanol 1 0.8 0.2. 

The above solution makes sense from the economic viewpoint, because the methyl ester is by far the most demanded, while 2-ethyl-hexanol is a cheap alcohol, in general a waste. The flowsheet in Figure 8.2 is still valid, in which the heavy alcohol is fed on the top stage, as an entrainer. Figure 8.15 shows the liquid concentration, reaction rate and temperature profiles. It can be seen that 2-ethyl-hexanol indeed plays its double role. The concentration of methanol in the top can be maintained at the minimum, such that there is no need for additional columns for methanol recovery and recycle. Note also that the operation takes place at low pressure (1.5 bar), in contrast with 6-12 bar and vacuum with individual light and heavy alcohols. 

In the case of esterification of lauric acid with methanol, the RCM analysis shows two alternatives (1) reflux of alcohol, but secondary methanol distillation, and (2) acid reflux (reactive absorption instead reactive distillation). The last alternative seems to be generic for any type of alcohol, but in practice it is limited by low volatility of fatty acids and high sensitivity to operating conditions. A better alternative is offered by dual reactive distillation, in which 2-ethyl-hexanol is added in the top as a coreactant and a mass-separation agent. 

Example 6.5. Olefin hydroformylation with phosphine-substituted cobalt hydrocarbonyl catalyst [30], The pathway 6.9 of olefin hydroformylation with the "oxo" catalyst, HCo(CO)4, has been shown in Example 6.2 in Section 6.3. For phosphine-substituted catalysts, HCo(CO)3Ph (Ph = organic phosphine), the pathway olefin — aldehyde is essentially the same. However, these catalysts also promote hydrogenation of aldehyde to alcohol (Examples 7.3 and 7.4) and of olefin to paraffin (Example 7.5). Moreover, straight-chain primary aldehydes under the conditions of the reaction undergo to some extent condensation to aldol, which is subsequently dehydrated and hydrogenated to yield an alcohol of twice the carbon number (e.g., 2-ethyl hexanol from n-butanal see Section 11.2). The entire reaction system is... 

SYNS 2-ETHYLBUTANOL-l 2-ETHYL-l-BLTANOL 2-ETHYLBUTYL ALCOHOL sec-HEXANOL pOT) sec-HEXYL ALCOHOL 3-METHYLOLPENTANE sec-PENTYLCARBINOL 3-PENTYLCARBINOL PSEL DOHEXYL ALCOHOL... 

Excellent n-propyl alcohol (30% by volume aqueous solution), n-hexyl alcohol, 2-ethyl-l-butanol, 2-ethyl-l-hexanol, lauryl alcohol, cyclo-hexanol... 

Glycerol Cyclohexanol Ethylene Glycol 2-Ethyl hexanol n-Amyl alcohol n Butanol... 

Propanol Amyl alcohol Decanol Acetone 2-Ethyl hexanol Diethyl amine Triethyl amine... 

The high thermal stability of the Deloxan ASP catalysts is also a key factor when looking at the achieved conversion rates in the esterification of phthalic anhydride with various alcohols, e.g. 1-octanol or 2-ethyl-hexanol, to yield di-octyl-phthalates (reaction 1) that are used as plasticizers. Product yields of > 99% for the diester are obtained for residence times between 30-50 minutes, at temperatures between 150°C and 180°C. 

The main volatiles in wines are the higher aliphatic alcohols, ethyl esters, and acetates formed from yeasts during fermentation. Acetates are very important flavors characterized by fruity notes, C4-Ci0 fatty acid ethyl esters manly confer fruity scents to the wine. Other wine aroma compounds are C6 alcohols, such as 1-hexanol and cis- and trans-3-hexen-l-ol, 2-phenylethanol, and 2-phenylethyl acetate. Contents of these compounds in wine are linked to the winemaking processes used fermentation temperature, yeast strain type, nitrogen level in must available for yeasts during fermentation, clarification of wine (Rapp and Versini, 1991). Much literature on the wine aroma compounds was reported in reviews by Schreier (1979) and Rapp (1988). 

Apart from propylene, which can be used as a raw material for the production of 2-ethyl hexanol, the mam olefins employed in the Oxo synthesis of higher alcohols result from ... 

Tables 9.15 and 9.16 summarize the main economic data available in the literature or recalculated, concerning the production of 2-ethyl hexanol, isooctanols in mixtures, or higher alcohols by different industrial processes.

These acrylates are usually manufactured in batches, because of the low tonnages required. Moreover, the corresponding alcohols are generally insoluble in water and thus difficult to recover by extraction ir-butanol, 2-ethyl hexanoL for example). They are obtained either by direct esterification of acrylic acid, or by transesterification of low molecular weight acrylates (methyl and ethyl acrylates). 

OTHER COMMENTS mostly used in alcoholic beverages in suitable dilutions also used as a solvent for resins, fats, fatty acids, oils and hydrocarbons other uses include the manufacture of acetaldehyde, acetic acid, ethylene, butadiene, 2-ethyl hexanol, dye, pharmaceuticals, elastomers, detergents, cleaning preparations, surface coatings, cosmetics, and explosives useful as an octane booster in gasoline. 

The consumption of 0x0 alcohol products in the United States, western Europe, and Japan for 1993 is shown in Table 7 [33], Table 7 shows that more than 50% of the total demand for 0x0 product is for n-butyraldehyde. Most is used to produce 2 ethyl hexanol. This is followed by demand for detergent alcohols, plasticizers, and the rest. The highest volume products have the lowest margin. The most profitable are the specialty 0x0 products which constitute the lower volumes. Most of the future growth is expected to be in the specialty products as well. 

Amyl alcohol Furfural 2-Ethyl hexanol Sulpholane... 

Synonyms /Mcohol C, 2-EH 2-Ethyl-1-hexanol 2-Ethylhexan-1-ol 2-Ethylhe) alcohol 1-Hexanol, 2-ethyl Classification Alcohol Empirical C,H 0 Formula CH,(CH2),CHC2H3CH20H... 

---