Isobutyl alcohol, ether formation

The Degussa process (now owned by Dupont) starts from acrolein, which is hydrated in the presence of an acidic ion exchanger into 3-hydroxypropanal (3HP, Fig. 8.8 a). The latter is subsequently extracted into isobutyl alcohol and hydrogenated over a Ni catalyst [53]. The overall yield does not exceed 85%, due to competing water addition at the 2-position and ether formation in the initial step. It has been announced that Degussa will supply up 10 kt a-1 to Dupont until the fermentative process of the latter company (see below) comes on stream [54]. 

The temperature effect on the dehydration of alcohols in the presence of alumina as has been shown by the work of Sabatier and Mailhe,41 Brown and Reid,°°b and Pease and Yung08 was not checked by Adkins,° b who used what were presumably better conditions experimentally. The rate of dehydration increases in the order of butyl, propyl, isobutyl, ethyl, isopropyl, and secondary butyl alcohols. Although ethanol and ethyl ether give the same rate of dehydration, butyl alcohol gives a faster dehydration late than does butyl ether. Hence, the hypothesis advanced at one time that olefin formation from alcohols was through intermediate ether formation cannot hold. 

Isoamyl isovalerate Isoamyl octanoate Isoamyl phenethyl ether Isoamyl phenylacetate Isoamyl propionate Isoamyl salicylate Isoamyl tiqiate Isoamyl valerate Isobornyl acetate Isobornyl formate Isobornyl isovalerate Isobornyl methyl ether Isobornyl propionate Isobutyl alcohol Isobutyl angelate... 

Ethyl ether Ethyl formate Ethyl oleate Formamide Formic acid Glycerin Glyceryl caprylate/caprate Glyceryl formal Heptane 2-Hexanone Hexylene glycol Hybrid safflower (Carthamus tinctorius) oil Isoamyl alcohol Isobutyl acetate Isobutyl alcohol. 

Erlenmeyer found that the butyl alcohol present in fusel oil yields iso-butyric acid (see below) on oxidation, and is therefore isobutyl alcohol, and he also showed that from isobutyl iodide the same valeric acid is obtained as from the amyl alcohol of fusel oil, which is therefore isoamyl alcohol, derived from dimethylethylmethane. Secondary butyl alcohol was first obtained as hydrate de butylene from erythritol by de Luynes. A. Lieben obtained it from zinc ethyl and dichloroethyl ether, and since he found that on oxidation it gives a ketone he recognised it as secondary butyl alcohol. Lieben and A. Rossi obtained normal butyl alcohol from butyric acid, which was converted into butyraldehyde by distilling calcium butyrate and calcium formate, and a solution of this reduced with a large amount of sodium amalgam. They give structural formulae for the four butyl alcohols, with the boiling-points. 

Isobutyl nitrite Butyl alcohol scc-Butyl alcohol t r -Butyl alcohol Ethyl ether Isobutyl alcohol Ethyl sulfide Pyridine Isovaleraldehyde 3-Methyl 2-butanone Isobutyl formate Isopropyl acetate Methyl isobutyrate Isoamyl nitrite tert-Amyl alcohol Isoamyl alcohol... 

Cyclopropane (0.5) -Propyl chloride (0.3) n-Propyl formate (0.3) Isopropyl chloride (0.3) Isopropyl alcohol (0.6) n-Butyl chloride (0.5) s-Butyl alcohol (0.6) Isobutyl bromide (—) Isobutyl alcohol (1) t-Butyl chloride (1). Butyl chloride (0.5).. t-Butyl alcohol (1.2) i-Butyl alcohol (0.3) t-Butyl alcohol (0.6) 3-Hexene (0.75) 3-Bromohexane (1) 3-Hexyl ether (0.18) Cyclohexene (1.5) Cyclohexyl bromide m.3)... 

Stepanov AG, Romannikov VN, Zamaraev KI. C CP/MAS NMR study of isobutyl alcohol dehydration on H-ZSM-5 zeolite. Evidence for the formation of stable isobutyl silyl ether intermediate. Catal Lett 1992 13 395 05. 

Methyl-1-propanethiol Methyl propionate 3-Methyl-5-propyl-2-cyclohexen-1 -one Methyl propyl ketone 2-Methylpyrazine flavoring agent, synthetic food Methyl salicylate Methyl sorbate 5-Methyl-2-thiophenecarboxyaldehyde 3-Methylthiopropionaldehyde 2-Methyl-3-tolylpropionaldehyde, mixed o-, m-, p-Methyl 9-undecenoate Methyl 2-undecynoate Methyl valerate MSG Musk ambrette Myrcene Myristaldehyde Myristyl alcohol Myrtenol 2-Naphthalenethiol P-Naphthyl ethyl ether P-Naphthyl isobutyl ether d-Neomenthol Nerol Neryl acetate Neryl butyrate Neryl formate Neryl isobutyrate Neryl isovalerate Neryl propionate... 

Isobutyl 2-furanpropionate Isobutyl heptanoate Isobutyl hexanoate Isobutyl isobutyrate 2-lsobutyl-3-methoxy-pyrazine a-lsobutylphenethyl alcohol Isobutyl phenylacetate Isobutyl propionate Isobutyl salicylate 2-lsobutylthiazole Isobutyric acid Isoeugenol Isoeugenyl benzyl ether Isoeugenyl ethyl ether Isoeugenyl formate... 

Hexenal cis-3-Hexenol cis-3-Hexenyl butyrate Hexyl tiglate Homolinalool Homolinalyl acetate Hydrocinnamaldehyde Hydrocinnamic alcohol Hydroxycitronellal diethyl acetal Hydroxycitronellal dimethyl acetal Hydroxycitronellal methyl anthranilate Hyssop (Hyssopus officinalis) oil Isoamyl acetate Isoamyl phenethyl ether Isoamyl salicylate Isobornyl formate Isobutyl anqelate Isobutyl benzoate ,Isobutyl phenylacetate 2-lsobutylquinoline Isobutyl salicylate... 

Polyvinyl isobutyl ether C6H12O2 Amyl formate n-Butyl acetate s-Butyl acetate t-Butyl acetate Caproic acid Diacetone alcohol Diethylacetic acid Ethyl butyrate Ethyl isobutyrate... 

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