IP Library Granted Patent US 11,377,404
Granted Patent B2
US 11,377,404 · App. 17/425,820 · Granted Jul 5, 2022

Process and plant for producing alpha olefins

Inventors: Florian Winkler (Munich, DE); Richard Schneider (Uffing am Staffelsee, DE); Florian Mündl (Otterfing, DE)
Assignee: LINDE GmbH
C07C7/17C07C2/08C07C7/1485
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Quick Facts
Patent No.
US 11,377,404
App. No.
17/425,820
Granted
Jul 5, 2022
Kind
B2
Abstract

A process ( 100 ) for the production of linear alpha-olefins is proposed, wherein ethylene is subjected to catalytic oligomerization ( 1 ) in a feed mixture to obtain a product mixture containing alpha-olefins with different chain length and side compounds. In a primary fractionation ( 2 ), a primary fraction is formed using at least part of the product mixture, and in a secondary fractionation ( 4 ), a secondary fraction is formed using at least part of the primary fraction. The primary fractionation ( 2 ) and the secondary fractionation ( 4 ) are carried out such that the primary fraction and the secondary fraction predominantly contain one of the alpha-olefins and are low in or free of other alpha-olefins, that the primary fraction contains one or more of the side compounds, and that the secondary fraction is depleted relative to the primary fraction in the one or more side compounds. In an intermediate step ( 3 ) between the primary fractionation ( 2 ) and the secondary fractionation ( 4 ), to which at least part of the primary fraction is subjected, the one or more side compounds are at least partly converted to one or more secondary compounds, and the one or more secondary compounds are at least partly separated in the secondary fractionation ( 4 ). The intermediate step ( 3 ) is carried out in such a way that not more than 0.8% of the alpha-olefin predominantly contained in the primary fraction or the part thereof subjected to the intermediate step is reacted. The intermediate step is carried out in the presence of 30 wt.-ppm to 200 wt.-ppm of water as reaction moderator and using a strongly acidic ion exchange resin.

Claims (20)

1. A process ( 100 ) for the preparation of linear alpha-olefins, wherein

ethylene in a feed mixture is subjected to catalytic oligomerization ( 1 ) to obtain a product mixture containing alpha-olefins with different chain lengths and side compounds,

a primary fraction is formed in a primary fractionation ( 2 ) using at least part of the product mixture, and a secondary fraction is formed in a secondary fractionation ( 4 ) using at least part of the primary fraction,

the primary fractionation ( 2 ) and the secondary fractionation ( 4 ) are carried out such that the primary fraction and the secondary fraction predominantly contain one of the alpha-olefins and are low in or free of other alpha-olefins, the primary fraction contains one or more of the side compounds, and the secondary fraction is depleted in or free of the one or more side compounds relative to the primary fraction, and

in an intermediate step ( 3 ) between the primary fractionation and the secondary fractionation, to which at least part of the primary fraction is subjected, the one or more side compounds are at least partly converted to one or more secondary compounds and the one or more secondary compounds are at least partly separated in the secondary fractionation,

wherein the alpha-olefin which the primary fraction and the secondary fraction predominantly contain is 1-hexene, the side compound or one of the side compounds is 2-ethyl-1-butene, and the secondary compound or one of the secondary compounds is 3-methyl-2-pentene, or wherein the alpha-olefin which the primary fraction and the secondary fraction predominantly contain is 1-octene, the side compound or one of the side compounds is 2-ethyl-1-hexene, and the secondary compound or one of the secondary compounds is 3-methyl-1-heptene,

characterized in that

the intermediate step is carried out in the presence of 20 wt.-ppm to 200 wt.-ppm water as reaction moderator and using a strongly acidic ion exchange resin, so that not more than 0.8% of the alpha-olefin predominantly contained in the primary fraction or the part thereof subjected to the intermediate step is reacted.

2. The process of claim 1 , wherein a macroporous sulfocationite is used as the strongly acidic ion exchange resin.

3. The process according to claim 1 , wherein the strongly acidic ion exchange resin has a volume based capacity of at least 4 eq/kg.

4. The process according to claim 1 , in which the intermediate step is carried out at a bed speed of 5 to 40 h −1 .

5. The process according to claim 1 , wherein 0.1 to 0.8% of the alpha-olefin predominantly contained in the primary fraction or its part subjected to the intermediate step is reacted.

6. The process according to claim 1 , in which the intermediate step is carried out at a temperature level of 60° C. to 100° C. and/or is carried out at a pressure level of 1.0 to 4.0 bar absolute pressure.

7. The process according to claim 1 , wherein the product mixture contains the 1-hexene and/or the 1-octene in a content of more than 50, 60, 70, 80 or 90% by weight.

8. The process according to claim 1 , wherein the alpha-olefin that the primary fraction and the secondary fraction predominantly contain is 1-hexene, wherein the content of 1-hexene is more than 90 wt.-%.

9. The process according to claim 1 , wherein the alpha-olefin that the primary fraction and the secondary fraction predominantly contain is 1-octene, wherein the content of 1-octene is more than 90 wt.-%.

10. The process according to claim 7 , wherein the product mixture contains the 1-hexene and/or the 1-octene in a content of more than 60% by weight.

11. The process according to claim 7 , wherein the product mixture contains the 1-hexene and/or the 1-octene in a content of more than 70% by weight.

12. The process according to claim 7 , wherein the product mixture contains the 1-hexene and/or the 1-octene in a content of more than 80% by weight.

13. The process according to claim 7 , wherein the product mixture contains the 1-hexene and/or the 1-octene in a content of more than 90% by weight.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 26, 2021
From: WINKLER, FLORIAN; SCHNEIDER, RICHARD; MÜNDL, FLORIAN
To: LINDE GMBH
Reel/Frame 057043/0847 →
Priority Claims (1)
EP 19154007 · Jan 28, 2019 · regional
Continuity (1)
Related Publication 20220162140A1 · May 26, 2022