Isomerization of vinylidene olefins
OwnerBonnie G. McKinnie, J. Todd Aplin +2inventors
InventorsBonnie G. McKinnie, J. Todd Aplin, Robert U. Lyons, Clinton R. Parham
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Abstract
Process technology for selectively isomerizing vinylidene olefin to tri-substituted olefin is described. The vinylidene olefin, normally in admixture with other types of olefins, especially linear 1-olefins, is treated with anhydrous hydrogen bromide under anhydrous conditions and in the absence of molecular oxygen and free radical initiator. The contacting period, which can be a matter of minutes, is sufficient to selectively isomerize the vinylidene olefin to tri-substituted olefin. If the process is conducted properly, little if any hydrobromination occurs.
Claims27
A process of isomerizing at least one vinylidene olefin to at least one tri-substituted olefin, which process comprises contacting the vinylidene olefin with anhydrous hydrogen bromide under anhydrous conditions and in the absence of molecular oxygen and free radical initiator, said contacting being for a period of time sufficient to isomerize vinylidene olefin to tri-substituted olefin.
A process for selective isomerization of at least one C10-20 vinylidene olefin to tri-substituted olefin in an anhydrous hydrocarbon mixture comprised of (i) at least one C10-20 vinylidene olefin, (ii) at least one C10-20 linear 1-olefin or (iii) at least one C10-20 remotely-branched 1-olefin, or (iv) a combination of (i), (ii) and (iii), and optionally (v) at least one C10-20 internal olefin or (vi) at least one saturated hydrocarbon, or (vii) both of (v) and (vi), while leaving the 1-olefins substantially unaffected during the isomerion, which process comprises contacting the mixture with anhydrous hydrogen bromide under anhydrous conditions and in the absence of molecular oxygen and free radical initiator for a period of time sufficient to selectively isomerize vinylidene olefin to tri-substituted olefin.
In a process for producing amine from a mixture of α-olefins comprising vinylidene olefins and 1-olefins, which process comprises:
- a) subjecting the mixture of olefins to selective isomerization to convert vinylidene olefins to tri-substituted olefins,
- b) hydrobrominating olefin mixture resulting from the isomerization to form bromoalkanes comprising 1-bromoalkanes and secondary bromoalkanes and/or tertiary bromoalkanes;
- c) selectively dehydrobrominating bromoalkanes resulting from b) whereby 1-bromoalkanes are substantially unaffected and secondary and/or tertiary bromoalkanes present are converted to olefins;
- d) aminating bromoalkanes from c) with an amine having at least one replaceable hydrogen atom whereby 1-bromoalkanes are converted to one or more amine hydrobromides;
- and
- e) converting amine hydrobromides from d) into one or more amines;
- the improvement which comprises effecting said selective isomerization by contacting said mixture of α-olefins with anhydrous hydrogen bromide under anhydrous conditions and in the absence of molecular oxygen and free radical initiator for a period of time sufficient to selectively isomerize vinylidene olefin to tri-substituted olefin.
Dependencies are inferred from the claim text.