Methods for making linear internal olefins from mixtures of linear and branched olefins
US-2024051900-A1 · Feb 15, 2024 · US
US9284237B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-9284237-B2 |
| Application number | US-201314105357-A |
| Country | US |
| Kind code | B2 |
| Filing date | Dec 13, 2013 |
| Priority date | Dec 13, 2013 |
| Publication date | Mar 15, 2016 |
| Grant date | Mar 15, 2016 |
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Methods and apparatuses for processing hydrocarbons are provided. In one embodiment, a method for processing hydrocarbons includes providing a stream of olefins including normal olefins and non-normal olefins. The method includes separating the normal olefins from the non-normal olefins to form a stream of normal olefins. Further, the method polymerizes the stream of normal olefins to form a stream of polymerized normal olefins. The method also includes saturating the stream of polymerized normal olefins to form a stream of normal paraffins.
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What is claimed is: 1. A method for processing hydrocarbons, the method comprising the steps of: providing a stream of olefins including normal olefins and non-normal olefins; separating the normal olefins from the non-normal olefins to form a stream of normal olefins; polymerizing the stream of normal olefins to form a stream of polymerized normal olefins; saturating the stream of polymerized normal olefins to form a stream of normal paraffins; and reforming the stream of normal paraffins to form a stream of aromatics. 2. The method of claim 1 wherein saturating the stream of polymerized normal olefins to form a stream of normal paraffins comprises forming the stream of normal paraffins comprising at least about 75 wt % normal compounds. 3. The method of claim 1 wherein saturating the stream of polymerized normal olefins to form a stream of normal paraffins comprises forming the stream of normal paraffins comprising at least about 90 wt % normal compounds. 4. The method of claim 1 wherein polymerizing the stream of normal olefins to form a stream of polymerized normal olefins comprises polymerizing at least about 50 wt % of the normal olefins. 5. The method of claim 1 wherein polymerizing the stream of normal olefins to form a stream of polymerized normal olefins comprises polymerizing at least about 75 wt % of the normal olefins. 6. The method of claim 1 wherein providing a stream of olefins including normal olefins and non-normal olefins comprises providing a stream of mixed C4 olefins, and wherein separating the normal olefins from the non-normal olefins to form a stream of normal olefins comprises: converting a portion of the stream of mixed C4 olefins to a C5 species; and separating the C5 species from unconverted C4 olefins. 7. The method of claim 1 wherein providing a stream of olefins including normal olefins and non-normal olefins comprises providing a stream of mixed C4 olefins, and wherein separating the normal olefins from the non-normal olefins to form a stream of normal olefins comprises: converting isobutene to methyl tertiary butyl ether (MTBE); and separating the MTBE from unconverted C4 olefins. 8. The method of claim 1 wherein: providing a stream of olefins including normal olefins and non-normal olefins comprises providing a stream of mixed C4 olefins; and polymerizing the stream of normal olefins to form a stream of polymerized normal olefins comprises forming the stream of polymerized normal olefins comprising at least about 50 wt % normal octene. 9. The method of claim 1 wherein: providing a stream of olefins including normal olefins and non-normal olefins comprises providing a stream of mixed C4 olefins; and polymerizing the stream of normal olefins to form a stream of polymerized normal olefins comprises forming the stream of polymerized normal olefins comprising at least about 50 wt % normal octene and at least about 10 wt % normal dodecene. 10. A method for processing hydrocarbons, the method comprising the steps of: introducing a stream of mixed C4 olefins to a reaction zone; converting a portion of the stream of mixed C4 olefins to a C5 species; separating the C5 species from unconverted C4 olefins; polymerizing the unconverted C4 olefins to form C8 olefins; and saturating the C8 olefins to form C8 paraffins. 11. The method of claim 10 further comprising reforming the C8 paraffins to form aromatics. 12. The method claim 10 wherein converting a portion of the stream of mixed C4 olefins to a C5 species comprises converting isobutene to methyl tertiary butyl ether (MTBE). 13. The method of claim 10 wherein saturating the C8 olefins to form C8 paraffins comprises saturating non-polymerized C4 olefins to form C4 paraffins. 14. The method of claim 10 wherein: separating the C5 species from unconverted C4 olefins comprises forming a stream of normal C4 olefins; polymerizing the unconverted C4 olefins to form C8 olefins comprises forming normal C8 olefins; and saturating the C8 olefins to form C8 paraffins comprises forming normal C8 paraffins. 15. The method of claim 10 wherein polymerizing the unconverted C4 olefins to form C8 olefins comprises polymerizing at least about 50 wt % of the unconverted C4 olefins into C8 olefins. 16. The method of claim 15 wherein polymerizing the unconverted C4 olefins to form C8 olefins comprises polymerizing at least about 10 wt % of the unconverted C4 olefins into C12 olefins. 17. The method of claim 10 wherein: separating the C5 species from unconverted C4 olefins comprises forming a stream of normal C4 olefins; polymerizing the unconverted C4 olefins to form C8 olefins comprises forming a stream of polymerized olefins; and saturating the C8 olefins to form C8 paraffins comprises saturating the stream of polymerized olefins to form a stream of saturated paraffins comprising at least about 75 wt % normal compounds. 18. The method of claim 10 wherein: separating the C5 species from unconverted C4 olefins comprises forming a stream of normal C4 olefins; polymerizing the unconverted C4 olefins to form C8 olefins comprises forming a stream of polymerized olefins; and saturating the C8 olefins to form C8 paraffins comprises saturating the stream of polymerized olefins to form a stream of saturated paraffins comprising at least about 90 wt % normal compounds. 19. An apparatus for processing hydrocarbons comprising: a separation zone configured to receive a stream of olefins including normal olefins and non-normal olefins and to separate the normal olefins from the non-normal olefins to form a stream of normal olefins; a polymerization zone configured to polymerize the stream of normal olefins to form a stream of polymerized normal olefins; and a saturation zone configured to saturate the stream of polymerized normal olefins to form a stream of normal paraffins. 20. A method for processing hydrocarbons, the method comprising the steps of: providing a stream of mixed C4 olefins including normal olefins and non-normal olefins; separating the normal olefins from the non-normal olefins to form a stream of normal olefins by converting a portion of the stream of mixed C4 olefins to a C5 species; and separating the C5 species from unconverted C4 olefins; polymerizing the stream of normal olefins to form a stream of polymerized normal olefins; and saturating the stream of polymerized normal olefins to form a stream of normal paraffins. 21. A method for processing hydrocarbons, the method comprising the steps of: providing a stream of mixed C4 olefins including normal olefins and non-normal olefins; separating the normal olefins from the non-normal olefins to form a stream of normal olefins by converting isobutene to methyl tertiary butyl ether (MTBE) and separating the MTBE from unconverted C4 olefins; polymerizing the stream of normal olefins to form a stream of polymerized normal olefins; and saturating the stream of polymerized normal olefins to form a stream of normal paraffins. 22. A method for processing hydrocarbons, the method comprising the steps of: providing a stream of mixed C4 olefins including normal olefins and non-normal olefins; separating the normal olefins from the non-normal olefins to form a stream of normal olefins; polymerizing the stream of normal olefins to form a stream of polymerized normal olefins comprising at least about 50 wt % normal octene; and saturating the stream of polymerized normal olefins to form a stream of normal p
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