Removal of alkyne impurities from diolefin containing mixtures through cracking over CuO/Al2O3 based materials

Patent metadata

Field	Value
Publication number	US-10906852-B2
Application number	US-201816500573-A
Country	US
Kind code	B2
Filing date	Apr 26, 2018
Priority date	Apr 27, 2017
Publication date	Feb 2, 2021
Grant date	Feb 2, 2021

Abstract

Processes to selectively crack alkyne compounds from a hydrocarbon stream including olefinic and di-olefinic compounds are described. The process includes contacting the hydrocarbon stream with a supported CuO catalyst under conditions sufficient to crack the alkynes to form a product stream that included cracked compounds and further separating the cracked organic compounds from the hydrocarbon stream.

First claim

The invention claimed is:

1. A process for removal of alkyne compounds from a hydrocarbon stream, the process comprising:
contacting a hydrocarbon stream comprising 5 to 10 wt. % C 4 mono-olefins and di-olefins, 30 to 50 wt. % C 5 mono-olefins and di-olefins, 39 to 64 wt. % aromatics and paraffins, and up to 3 wt. % alkynes with a supported CuO catalyst under conditions sufficient to crack the alkynes to form a product stream comprising cracked compounds; and
recovering the product stream comprising the cracked compounds.

2. The process of claim 1 , wherein the conditions sufficient to crack the alkynes to form the product stream comprising the cracked compounds comprise a temperature of 100 to 125° C. and a pressure of 0.5 MPa to 2.5 MPa at a liquid hourly space velocity of 5 to 15 h −1 .

3. The process of claim 2 , wherein the hydrocarbon stream comprises 0.2 to 0.3 wt. % of the alkynes.

4. The process of claim 1 , wherein the conditions sufficient to crack the alkynes to form the product stream comprising the cracked compounds comprise a temperature of a temperature of 160 to 185° C. and a pressure of 0.05 MPa to 0.5 MPa at a gas hourly space velocity of 280 to 400 h −1 .

5. The process of claim 4 , wherein the hydrocarbon stream comprises 0.2 to 0.3 wt. % of the alkynes.

6. The process of claim 1 , wherein the hydrocarbon feed comprises 6.5 to 7.8 wt. % C 4 mono-olefins and di-olefins, 34 to 42 wt. % C 5 mono-olefins and di-olefins, 39 to 43 wt. % C 5 paraffins, 10 to 14 wt. % isoprene, 0.2 to 0.9 wt. % alkynes, and 0.1 wt. % C 6+ compounds.

7. The process of claim 1 , wherein a support of the supported CuO catalyst comprises alumina, carbon, silica or zirconia or combinations thereof.

8. The process of claim 1 , where the supported CuO catalyst is a CuO/Al 2 O 3 catalyst.

9. The process of claim 1 , where the supported CuO catalyst further comprises one or more promoters and/or co-active compounds.

10. The process of claim 9 , wherein the promoters comprise silver (Ag), platinum (Pt), palladium (Pd), manganese (Mn), cobalt (Co), nickel (Ni), chromium (Cr), molybdenum (Mo), or mixtures thereof.

11. The process of claim 1 , wherein the hydrocarbon stream further comprises an optional inhibitor to inhibit polymerization of the C 4 and/or C 5 di-olefins.

12. The process of claim 1 , wherein the contacting further produces coke.

13. The process of claim 1 , wherein the contacting further produces hydrogen gas.

14. The process of claim 1 , wherein the alkynes comprise 2-butyne, 1-butyne, propyne, pentyne or isomers thereof, or combinations thereof.

15. The process of claim 1 , wherein the cracked compounds comprise alkanes.

16. The process of claim 15 , wherein the alkanes are methane, ethane, ethene, or mixtures thereof.

17. The process of claim 1 , wherein a di-olefin loss from the hydrocarbon stream is less than 1 wt. %.

18. The process of claim 17 , wherein the di-olefin loss is an isoprene loss.

19. The process of claim 1 , wherein the hydrocarbon stream comprises 0.2 to 0.3 wt. % of the alkynes.

Assignees

• Sabic Global Technologies Bv

Inventors

• Supronowicz Wojciech

Classifications

• C07C2523/72

  Copper · CPC title

• C07C7/1485 Primary

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

• C10G2300/1092

  C2-C4 olefins · CPC title

• C10G2300/4012

  Pressure · CPC title

• C07C2521/04

  Alumina · CPC title