Methods of removing carbonyl-containing organic compounds

Patent metadata

Field	Value
Publication number	US-10947175-B2
Application number	US-201916678225-A
Country	US
Kind code	B2
Filing date	Nov 8, 2019
Priority date	Nov 30, 2018
Publication date	Mar 16, 2021
Grant date	Mar 16, 2021

Abstract

Provided are methods of treating a mixture, such as a hydrocarbon mixture, that includes one or more C2-C4 carbonyl containing organic compounds. The methods may include contacting a hydrocarbon mixture with an aqueous liquid including an agent. The agent may reduce the amount of one or more C2-C4 carbonyl containing organic compounds in the mixture.

First claim

What is claimed is:

1. A method of treating a mixture, the method comprising:
providing a hydrocarbon mixture comprising one or more C2-C4 carbonyl-containing organic compounds; and
contacting the hydrocarbon mixture with an aqueous liquid comprising an agent, the agent comprising: (i) sodium sulfite (Na 2 SO 3 ), (ii) sodium bisulfite (NaHSO 3 ), (iii) sodium metabisulfite (Na 2 S 2 O 5 ), (iv) sodium borohydride (NaBH 4 ), (v) dimethylacetamide (CH 3 CN(CH 3 ) 2 ), or (vi) a combination thereof;
wherein the one or more C2-C4 carbonyl-containing organic compounds comprise propanal, propenal, butanone, butenone, butanal, butenal, or a combination thereof, and
wherein the hydrocarbon mixture and the aqueous liquid are present at a volume ratio of about 0.5:1 to about 1.5:1.

2. The method of claim 1 , further comprising separating the hydrocarbon mixture and the aqueous liquid to form a product hydrocarbon mixture.

3. The method of claim 2 , wherein an amount of the one or more C2-C4 carbonyl-containing organic compounds that is present in the product hydrocarbon mixture is about 95% to 100% less than an amount of the one or more C2-C4 carbonyl-containing organic compounds in the hydrocarbon mixture.

4. The method of claim 1 , wherein each of the one or more C2-C4 carbonyl-containing organic compounds is independently present in the hydrocarbon mixture at an amount of about 5 wtppm to about 25 wtppm.

5. The method of claim 1 , wherein the one or more C2-C4 carbonyl-containing organic compounds comprise acetaldehyde, propenal, 3-buten-2-one, crotonaldehyde, or a combination thereof.

6. The method of claim 5 , wherein the acetaldehyde, the propenal, the 3-buten-2-one, and the crotonaldehyde are independently present in the hydrocarbon mixture at an amount of about 5 wtppm to about 25 wtppm.

7. The method of claim 1 , wherein the agent is present in the aqueous liquid at an amount of about 10% to about 30% by weight, based on the total weight of the aqueous liquid and the agent.

8. The method of claim 1 , wherein the agent is present in the aqueous liquid at an amount of about 15% to about 25% by weight, based on the total weight of the aqueous liquid and the agent.

9. The method of claim 1 , wherein the hydrocarbon mixture comprises C4 paraffins, C4 olefins, butadiene, and acetylenes.

10. The method of claim 1 , wherein the contacting of the hydrocarbon mixture with the aqueous liquid comprises mixing the hydrocarbon mixture and the aqueous liquid.

11. A method of treating a mixture, the method comprising:
providing a hydrocarbon mixture, the hydrocarbon mixture comprising [1] about 5 wtppm to about 200 wtppm of acrolein, [2] about 5 wtppm to about 200 wtppm of 3-buten-2-one, [3] about 5 wtppm to about 200 wtppm of crotonaldehyde, or [4] a combination thereof;
contacting the hydrocarbon mixture with an aqueous liquid comprising an agent, the agent comprising: (i) sodium sulfite (Na 2 SO 3 ), (ii) sodium bisulfite (NaHSO 3 ), (iii) sodium metabisulfite (Na 2 S 2 O 5 ), (iv) sodium borohydride (NaBH 4 ), (v) dimethylacetamide (CH 3 CN(CH 3 ) 2 ), or (vi) a combination thereof, wherein the hydrocarbon mixture and the aqueous liquid are present at a volume ratio of about 0.5:1 to about 1.5:1; and
separating the hydrocarbon mixture and the aqueous liquid to form a product hydrocarbon mixture;
wherein the product hydrocarbon mixture comprises at least one of acrolein, 3-buten-2-one, or crotonaldehyde at a concentration of 0 wtppm to about 3 wtppm.

12. The method of claim 11 , wherein the product hydrocarbon mixture comprises [1] 0 wtppm to about 3 wtppm of acrolein, [2] 0 wtppm to about 3 wtppm of 3-buten-2-one, and [3] 0 wtppm to about 3 wtppm of crotonaldehyde.

13. The method of claim 11 , wherein the product hydrocarbon mixture comprises at least one of acrolein, 3-buten-2-one, or crotonaldehyde at a concentration of 0 wtppm to about 1 wtppm.

14. The method of claim 11 , wherein the product hydrocarbon mixture comprises [1] less than about 3 wtppm of acrolein, [2] less than about 3 wtppm of 3-buten-2-one, and [3] less than about 3 wtppm of crotonaldehyde.

15. The method of claim 11 , wherein the contacting of the hydrocarbon mixture with the aqueous liquid comprises mixing the hydrocarbon mixture and the aqueous liquid.

16. The method of claim 15 , wherein the hydrocarbon mixture and the aqueous liquid are present at a volume ratio of about 0.8:1 to about 1.2:1.

17. A method of treating a mixture, the method comprising:
providing a hydrocarbon mixture, the hydrocarbon mixture comprising one or more C2-C4 carbonyl-containing organic compounds, wherein at least one of the one or more C2-C4 carbonyl-containing organic compounds is present at a concentration of about 5 wtppm to about 200 wtppm;
contacting the hydrocarbon mixture with an aqueous liquid comprising an agent, the agent comprising: (i) sodium sulfite (Na 2 SO 3 ), (ii) sodium bisulfite (NaHSO 3 ), (iii) sodium metabisulfite (Na 2 S 2 O 5 ), (iv) sodium borohydride (NaBH 4 ), (v) dimethylacetamide (CH 3 CN(CH 3 ) 2 ), or (vi) a combination thereof, and wherein the hydrocarbon mixture and the aqueous liquid are present at a volume ratio of about 0.5:1 to about 1.5:1;
separating the hydrocarbon mixture and the aqueous liquid to form a product hydrocarbon mixture;
wherein the product hydrocarbon mixture comprises 0 wtppm to about 3 wtppm of the C2-C4 carbonyl-containing organic compound that was present in the hydrocarbon mixture at the concentration of about 5 wtppm to about 200 wtppm.

18. The method of claim 17 , wherein the product hydrocarbon mixture comprises 0 wtppm to about 1 wtppm of the C2-C4 carbonyl-containing organic compound that was present in the hydrocarbon mixture at the concentration of about 5 wtppm to about 200 wtppm.

19. The method of claim 17 , wherein the agent is present in the aqueous liquid at an amount of about 10% to about 30% by weight, based on the total weight of the aqueous liquid and the agent.

20. The method of claim 17 , wherein the contacting of the hydrocarbon mixture with the aqueous liquid comprises mixing the hydrocarbon mixture and the aqueous liquid.

Assignees

• Lyondell Chemical Tech Lp

Inventors

• Zhang Lei
• White Daniel F

Classifications

• C07C7/17 Primary

  with acids or sulfur oxides · CPC title

• C07C7/152

  by forming adducts or complexes · CPC title

• C07C7/14875

  with organic compounds (organo-metallic compounds C07C7/173) · CPC title

• C07C7/14858

  with inorganic compounds not provided for before (acids, sulfur oxides C07C7/17) · CPC title

• C07C45/86 Primary

  Use of additives, e.g. for stabilisation · CPC title