Chemistry of hydrocarbon compounds – Purification – separation – or recovery – By addition of extraneous agent – e.g. – solvent – etc.
Reexamination Certificate
1999-05-11
2001-01-16
Utech, Benjamin L. (Department: 1764)
Chemistry of hydrocarbon compounds
Purification, separation, or recovery
By addition of extraneous agent, e.g., solvent, etc.
C585S809000, C585S833000, C585S866000
Reexamination Certificate
active
06175050
ABSTRACT:
1. FIELD OF THE INVENTION
This invention relates to a process for separating functionalized alpha olefins from functionalized internal olefins.
2. BACKGROUND OF THE INVENTION
Many industrial processes produce olefins that are mixtures of functionalized internal olefins and functionalized alpha olefins. Olefins are frequently used in the manufacture of polymers, as drilling mud additives or as intermediates for the production of oil additives and detergents. Functionalized olefins, and in particular functionalized alpha olefins, may be used in applications such as polymers and chemical intermediates.
Depending upon the particular application, it would be desirable to manufacture a functionalized alpha olefin composition having the greatest purity possible. While pure species of functionalized alpha and internal olefins with a narrow carbon number range can be manufactured or produced in small quantities at a great cost, we have found that it would be particularly desirable to economically provide large quantities of separated and purified functionalized alpha and functionalized internal olefins from commercial raw feedstocks containing a mixture of functionalized internal olefins and functionalized alpha olefins. Examples include feeds containing the synthetic reaction products of syn-gas, such as those found in Fisher-Tropsch streams; by the oxidation of unsaturated and saturated hydrocarbons which often form unsaturated by-products; and the dehydrogenation of oxygenated hydrocarbons.
Separating and isolating functionalized alpha olefins from functionalized internal olefins is no easy task, especially when these species have similar or identical molecular weights or carbon numbers or when the only difference in the species one desires to separate is the position of the double bond. Conventional distillation methods are frequently inadequate to separate species of this type, which have such closely related boiling points. The separation problem is further aggravated in that the functionalized alpha olefin species not only needs to be separated from functionalized internal olefins, but also from those species containing differing functional groups and the saturated hydrocarbons.
U.S. Pat. No. 4,946,560 described a process for the separation of internal olefins from alpha olefins by contacting a feedstock with anthracene to form an olefin adduct, separating the adduct from the feedstock, dissociating the olefin adduct through heat to produce anthracene and an olefin composition enriched in alpha olefin, and separating out the anthracene from the alpha olefin. This reference does not suggest the desirability or the capability of anthracene to conduct a separation operation between functionalized alpha olefins and functionalized internal olefins.
3. SUMMARY OF THE INVENTION
This invention relates to a process for separating functionalized alpha olefins from functionalized internal olefins. In particular, there is provided a process for treating a feedstock comprised of functionalized alpha olefins and functionalized internal olefins, comprising:
a) contacting the feedstock with a linear polyaromatic compound under conditions effective to form a reaction mixture comprising a linear polyaromatic compound-functionalized alpha olefin adduct;
b) separating the linear polyaromatic compound-functionalized alpha olefin adduct, and optionally the unreacted linear polyaromatic compound as well, from the reaction mixture, to form a functionalized adducted alpha olefin stream and a functionalized internal olefin stream;
c) dissociating the linear polyaromatic compound-functionalized alpha olefin adduct in said functionalized adducted alpha olefin stream to form a linear polyaromatic compound and a functionalized alpha olefin composition, and optionally
d) separating the linear polyaromatic compound formed in step c) from a functionalized alpha olefin composition;
whereby the concentration of functionalized alpha olefin in said alpha olefin composition is enriched in functionalized alpha olefin over the concentration of functionalized alpha olefin in the feedstock. In another embodiment of the invention, the concentration of functionalized internal olefin in the internal olefin stream is enriched in functionalized internal olefin over the concentration of functionalized internal olefin present in the feedstock.
4. DETAILED DESCRIPTION OF THE INVENTION
As used throughout this specification and in the claims, the term “comprising” means “at least,” such that other unmentioned elements, ingredients, or species are not excluded from the scope of invention.
Functionalized olefins, whether internal or alpha, are lo compounds with at least one double bond located on an aliphatic or cycloaliphatic moiety of the compound, and the olefin has a functional group, other than C—C unsaturation. Examples of chemically reactive functional groups are carboxyl, aldehyde, keto, thio, ester, ether, hydroxyl, and amine. The number of functional groups on a molecule is not limited. The functional groups may be located anywhere along the carbon backbone.
The functionalized olefins may contain aryl moieties along with an aliphatic or cycloaliphatic moiety within the same compound, or may consist solely of an aliphatic, cycloaliphatic, or cycloaliphatic with aliphatic moieties on the compound. Preferably, the functionalized olefin is an aliphatic compound.
The functionalized olefin may be branched or linear. Examples of branching include alkyl, aryl, or alicyclic branches. The number of unsaturation points along the chain is also not limited. The olefin may be a mono-, di-, tri-, etc unsaturated olefin, optionally conjugated.
A functionalized alpha olefin is an olefin whose double bond is located on both of any &agr; and its &bgr; carbon atoms. An &agr; carbon atom is any terminal carbon atom, regardless of how long the chain is relative to other chain lengths in a molecule. The location of any branches or additional functional groups on the functionalized alpha olefin is not limited. Branches or functional groups compatible with double bonds may be located on double bond carbon atoms, on carbon atoms adjacent to the double bond carbon atoms, or anywhere else along the carbon backbone. The functionalized alpha olefin may also be a poly-ene, wherein two or more points of unsaturation may be located anywhere along the molecule, so long as at least one double bond is in the alpha position.
A functionalized internal olefin(s) is an olefin whose double bond is located anywhere along the carbon chain except at any terminal carbon atom. The location of a branch or a functional group on the functionalized internal olefin is not limited. Branches or functional groups may be located on the double bond carbon atoms, on carbon atoms adjacent to the double bond carbon atoms, or anywhere else along the carbon backbone.
Examples of functionalized olefins include unsaturated fatty acids, &agr;,&bgr;-unsaturated acids and esters, &ohgr;-unsaturated acids and esters, C
5
-C
20
alpha or internal primary alcohols, and C
5
-C
20
alpha or internal ketones and aldehydes.
The feedstock olefins used in the process of the invention comprise functionalized alpha olefins and functionalized internal olefins. The feedstock may optionally contain other kinds of olefins, such as linear and/or branched internal and alpha olefins, as well as aromatic compounds and paraffins. The feedstock is generally produced by commercial processes such as the oxidation of saturated and unsaturated hydrocarbons or the dehydrogenation of functionalized hydrocarbons. Alternatively, the feedstock may be produced by the Fisher-Tropsch process, which often contains functionalized species. A Fisher-Tropsch process catalytically hydrogenates CO and advances toward the production of compositions containing aliphatic molecular chains. The most preferred feedstock is that obtained from a Fisher-Tropsch (FT) synthesis.
FT catalysts and reaction conditions can be selected to provide a particular mix of species in the reaction product stream. For example, the particular catalys
Fenouil Laurent Alain
Fong Howard Lam-Ho
Slaugh Lynn Henry
Carmen Dennis V.
Nguyen Tam M.
Shell Oil Company
Utech Benjamin L.
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