Process and plant for producing alpha olefins

Patent metadata

Field	Value
Publication number	US-11377404-B2
Application number	US-202017425820-A
Country	US
Kind code	B2
Filing date	Jan 28, 2020
Priority date	Jan 28, 2019
Publication date	Jul 5, 2022
Grant date	Jul 5, 2022

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.

First claim

The invention claimed is:

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.

Assignees

• Linde Gmbh

Inventors

• Winkler Florian
• Schneider Richard
• Mündl Florian

Classifications

• C07C7/1485

  oxides; hydroxides; salts (C07C7/156 takes precedence) · CPC title

• C07C2/08

  Catalytic processes · CPC title

• C07C2/06 Primary

  of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond · CPC title

• C07C7/17 Primary

  with acids or sulfur oxides · CPC title

• C07C11/107

  with six carbon atoms · CPC title