The Conversion of Acetone to Isoprene

Taylor, Hugh S.; Shenk, W. J.

doi:10.1021/ja01855a073

Cited by 9 publications

(5 citation statements)

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“…Another product of this reaction is the glycol, 2,5-dimethyl-3-hexvne-2,5-diol. This side reaction was minimized by passing acetylene into the liquid ammonia solution until after the acetone addition was complete (1,7). When this precaution was used in the present study, it was found that the carbon-14 content of the dimethylethvnylcarbinol was much less than should have been obtained.…”

Section: Methodsmentioning

confidence: 79%

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Determination of Unsaturation in Butyl Rubber Using Carbon-14-Labeled Isoprene

McNall¹,

Eby²

1957

Anal. Chem.

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Section: Methodsmentioning

confidence: 79%

“…EXPERIMENTAL Carbon-14-Labeled Isoprene. Isoprene was prepared from acetylene and acetone by the method of Taylor and Shenk (7). Radioactivity was introduced into the isoprene molecule by using carbon-14-labeled acetylene as a starting material.…”

Section: Methodsmentioning

confidence: 99%

Determination of Unsaturation in Butyl Rubber Using Carbon-14-Labeled Isoprene

McNall¹,

Eby²

1957

Anal. Chem.

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“…Sodium acetylide in particular has been used widely in the preparation of mono-and di-alkylacetylenes and related compounds (28,30,31,49,53,79,85,174,179,188,195,223,229,268,272,273,282,296,297,327,328,329,387,390,391, 409, 434), using, for example, alkyl halides, sulfates, or esters as the alkylation agents. Condensation of acetylides with aldehydes, ketones, and the like has been used extensively in the preparation of acetylenic carbinols (1,13,36,51,53,91,135,164,165,167,168,171,178,184,198,199,208,228,264,265,266, 287, 290,337,348,386,387). Acetylenic acids ...…”

Section: E Acetylenic Hydrocarbonsmentioning

confidence: 99%

Reactions of Organic and Organometallic Compounds with Solutions of Metals in Liquid Ammonia.

Watt¹

1950

Chem. Rev.

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“…Previous work published by us and by other research teams has shown that the selective production of isoprene from prenol is challenging under relatively mild conditions (<150°C) and often results in a mixture of products, such as ethers, ketones, and isomers of prenol in the presence of both homogenous and heterogeneous catalysts ( Marton et al, 1989 ; Bianchini et al, 2001 ; Todd and Bielawski, 2013 ; Cosimbescu et al, 2022 ). Notably, Taylor and Shenk reported selective production of isoprene from prenol isomeric alcohol under harsh conditions (300°C) ( Taylor and Shenk, 2002 ). However, in their study, the alcohol was prepared in 50% yield by the reduction of its butyne precursor, 2-methylbut-3-yne-2-ol, with a large excess of copper zinc dust.…”

Section: Introductionmentioning

confidence: 99%

Solvent-Induced Selectivity of Isoprene From Bio-Derived Prenol

2022

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In this work we demonstrate the selective catalytic conversion of prenol, which is an allylic alcohol that can be prepared from renewable resources to isoprene. The catalyst is an inexpensive molybdenum complex (Molyvan L) designed and used as an additive for lubricants. Isoprene is generated under relatively mild reaction parameters at 130–150°C, for 2 h, under vapor pressure conditions that do not exceed 50 psi. Two cases were studied: one in which Molyvan L was dissolved in a base oil at 1% concentration (weight/weight) and then mixed with a solvent and prenol and the other in which neat Molyvan L was introduced in the reaction and the base oil was replaced with the solvent and prenol. We investigated the selectivity of the reaction using the following solvents in both cases: dodecane, dodecanol, isododecane, octane, blendstock for oxygenate blending (BOB3), a fuel surrogate, a polyalphaolefin (PAO4), and methoxy polyethylene glycol (methoxy PEG350). Although conversion of prenol was above 94% in all experiments, isoprene was formed with various degrees of efficiency alongside a prenol isomeric alcohol, diprenyl ether and mixed ether via intramolecular and intermolecular dehydration reactions. Dodecane appeared to have the highest level of selectivity initially in base oil so we studied the effect of various dodecane-like solvents on isoprene yield and product profile. Surprisingly, octane (similar to dodecane) and isododecane (branched alkane) generated insignificant amounts of byproducts, essentially providing the highly desired isoprene with a very high selectivity. Branching of the solvent does not appear to have an effect on selectivity. Another advantage of this catalyst is the low loadings required to effect the transformation; that is, 0.25% (weight/volume) in the cases using neat Molyvan L and 0.5% (weight/volume) in the cases using Molyvan L dissolved in the base oil. Provided that prenol can be produced in large scale from bioresources, this work would enable the sustainable production of isoprene, in good yield, and with very high selectivity.

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The Conversion of Acetone to Isoprene

Cited by 9 publications

References 0 publications

Determination of Unsaturation in Butyl Rubber Using Carbon-14-Labeled Isoprene

Determination of Unsaturation in Butyl Rubber Using Carbon-14-Labeled Isoprene

Reactions of Organic and Organometallic Compounds with Solutions of Metals in Liquid Ammonia.

Solvent-Induced Selectivity of Isoprene From Bio-Derived Prenol

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