Method of producing a fuel additive

Patent metadata

Field	Value
Publication number	US-11414611-B2
Application number	US-201917052407-A
Country	US
Kind code	B2
Filing date	Apr 18, 2019
Priority date	May 7, 2018
Publication date	Aug 16, 2022
Grant date	Aug 16, 2022

Abstract

A method of producing a fuel additive includes passing a feed stream comprising C4 hydrocarbons through a methyl tertiary butyl ether unit producing a first process stream; passing the first process stream through a selective butadiene hydrogenation unit transforming greater than or equal to 90% by weight of the butadiene to 1-butene and 2-butene, preferably greater than or equal to 93%, preferably, greater than or equal to 94%, more preferably, greater than or equal to 95% producing a second process stream; passing the second process stream through a hydration unit producing a third process stream and the fuel additive; passing the third process stream through a total hydrogenation unit producing a hydrogenated stream; and passing the hydrogenated stream to a cracker unit.

First claim

What is claimed is:

1. A method of producing a fuel additive, comprising:
passing a feed stream comprising C4 hydrocarbons through a methyl tertiary butyl ether unit producing a first process stream and a methyl tertiary butyl ether product;
passing the first process stream through a selective butadiene hydrogenation unit transforming greater than or equal to 90% by weight of butadiene in the first process stream to 1-butene and 2-butene, producing a second process stream;
passing the second process stream through a hydration unit producing a third process stream and the fuel additive, wherein the second process stream comprises less than or equal to 5.0% by weight butadiene prior to passing through the hydration unit;
passing the third process stream through a total hydrogenation unit producing a hydrogenated stream; and
passing the hydrogenated stream to a cracker unit.

2. The method of claim 1 , wherein a source of the feed stream comprises a product of an olefin cracking process and/or an olefin production process.

3. The method of claim 1 , wherein the feed stream comprises at least one of propane, propylene, ethyl acetylene, vinyl acetylene, 1,3-butadiene, 1,2-butadiene, isobutylene, cis-2-butene, trans-2-butene, 1-butene, isobutane, or n-butane.

4. The method of claim 1 , further comprising contacting the feed stream with a catalyst within the methyl tertiary butyl ether unit, wherein the catalyst comprises an acid-type ion-exchange resin.

5. The method of claim 1 , wherein a temperature within the methyl tertiary butyl ether unit is 15° C. to 150° C. and a pressure within the methyl tertiary butyl ether unit is 500 kiloPascals to 2800 kiloPascals.

6. The method of claim 1 , wherein methanol and isobutylene are present in the methyl tertiary butyl ether unit in a molar ratio of one mole of isobutylene to 0.1 mole to 5 moles of methanol.

7. The method of claim 1 , wherein greater than or equal to 75% by weight of any isobutylene present in the feed stream is converted to methyl tertiary butyl ether within the methyl tertiary butyl ether unit.

8. The method of claim 1 , further comprising withdrawing the methyl tertiary butyl ether product from the methyl tertiary butyl ether unit; and
wherein the purity of the methyl tertiary butyl ether product is greater than or equal to 90%.

9. The method of claim 1 , wherein the second process stream comprises less than or equal to 1.0% by weight butadiene prior to passing through the hydration unit.

10. The method of claim 1 , further comprising contacting the second process stream with a catalyst within the hydration unit, wherein the catalyst comprises at least one of phosphoric acid, hypophosphorous acid, an ion-exchange resin, sulfur, polystyrene, a polymer, or niobium oxide.

11. The method of claim 1 , wherein a temperature within the hydration unit is 30° C. to 250° C. and a pressure within the hydration unit is 500 kiloPascals to 20,000 kiloPascals.

12. The method of claim 1 , wherein greater than or equal to 90% of any butene present in the second process stream is converted to butanol within the hydration unit.

13. The method of claim 1 , further comprising withdrawing a fuel additive product from the hydration unit.

14. The method of claim 13 , wherein the fuel additive product comprises at least one of 1-butanol, 2-butanol, tert-butyl alcohol, or a C4 dimer.

15. The method of claim 13 , wherein a research octane number of the fuel additive product is greater than or equal to 80.

16. The method of claim 13 , wherein a Reid vapor pressure of the fuel additive product is less than or equal to 55 kiloPascals.

17. The method of claim 13 , wherein a research octane number of the fuel additive product is greater than or equal to 85; and
wherein a Reid vapor pressure of the fuel additive product is less than or equal to 25 kiloPascals.

18. The method of claim 1 , wherein greater than or equal to 90% of any butene present in the third process stream is converted to butane within the total hydrogenation unit.

19. The method of claim 1 , wherein passing the first process stream through the selective butadiene hydrogenation unit transforms greater than or equal to 95% by weight of butadiene to 1-butene and 2-butene;
wherein the second process stream comprises less than or equal to 1.0% by weight butadiene prior to passing through the hydration unit; and
wherein greater than or equal to 90% of any butene present in the third process stream is converted to butane within the total hydrogenation unit.

20. A method of producing a fuel additive, comprising:
passing a feed stream comprising hydrocarbons through a cracker unit producing a cracked stream;
passing the cracked stream through a methyl tertiary butyl ether unit to produce a first process stream, wherein methanol and isobutylene are present in the methyl tertiary butyl ether unit in a molar ratio of one mole of isobutylene to 0.1 mole to 5 moles of methanol;
withdrawing a methyl tertiary butyl ether product from the methyl tertiary butyl ether unit;
passing the first process stream through a selective butadiene hydrogenation unit transforming greater than or equal to 90% by weight of butadiene in the first process stream to 1-butene and 2-butene, and producing a second process stream;
passing the second process stream through a hydration unit producing a third process steam, wherein a temperature within the hydration unit is 30° C. to 190° C., a pressure within the hydration unit is 500 kiloPascals to 20,000 kiloPascals, and wherein greater than or equal to 90% of any butene present in the second process stream is converted to butanol within the hydration unit, and wherein the second process stream comprises less than or equal to 5.0% by weight butadiene prior to passing through the hydration unit;
withdrawing a fuel additive product from the hydration unit, wherein the fuel additive product comprises at least one of 1-butanol, 2-butanol, tert-butyl alcohol, or a C4 dimer;
passing the third process stream through a total hydrogenation unit producing a hydrogenated process stream; and
recycling the hydrogenated process stream to a cracker unit;
wherein the fuel additive product comprises 1 to 25 weight percent trimethylpentane, and wherein the fuel additive product comprises less than or equal to 1% by weight diene impurities.

Assignees

• Sabic Global Technologies Bv
• Saudi Arabian Oil Co

Inventors

• Leal Guillermo
• Shaik Kareemuddin Mahaboob
• Al-Otaibi Naif Mohammed Al-Naddah
• Shethna Hiren
• Ansari Mohammed Bismillah
• Zhang Zhonglin

Classifications

• C07C5/05

  Partial hydrogenation · CPC title

• C10G45/32

  Selective hydrogenation of the diolefin or acetylene compounds · CPC title

• C07C4/04

  Thermal processes {(C07C4/025 takes precedence)} · CPC title

• C07C41/06

  by addition of organic compounds only · CPC title

• C07C29/04

  by hydration of carbon-to-carbon double bonds · CPC title