IP Library › Granted Patent US 12,264,123
Granted Patent B2
US 12,264,123 · App. 17/436,753 · Granted Apr 1, 2025

Method of producing a fuel additive

Inventors: Guillermo Leal (Riyadh, SA); Naif Mohammed Al-Naddah Al-Otaibi (Riyadh, SA); Kareemuddin Mahaboob Shaik (Dhahran, SA); Mohammed Bismillah Ansari (Riyadh, SA); Vijay Dinkar Bodas (Riyadh, SA)
Assignees: SABIC GLOBAL TECHNOLOGIES B.V.; SAUDI ARABIAN OIL COMPANY
C07C29/04B01D3/009C07C4/06C07C5/03C07C5/05C07C7/005C07C7/04C10L1/02C10L1/1824
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Quick Facts
Patent No.
US 12,264,123
App. No.
17/436,753
Granted
Apr 1, 2025
Kind
B2
Abstract

A method of producing a fuel additive includes passing a feed stream comprising C 4 hydrocarbons through a first hydrogenation unit producing a first process stream; passing the first process stream through a distillation unit; withdrawing a 2-butene stream from the distillation unit: passing the 2-butene stream through a second hydrogenation unit producing a 1-butene stream; passing at least a portion of the 1-butene stream through a separation unit; and passing the 1-butene stream through a hydration unit producing the fuel additive.

Claims (50)

1. A method of producing a fuel additive, comprising:

passing a feed stream comprising C 4 hydrocarbons through a first hydrogenation unit producing a first process stream;

passing the first process stream through a distillation unit;

withdrawing a 2-butene stream from the distillation unit;

passing the 2-butene stream through a second hydrogenation unit producing a 1-butene stream;

passing at least a portion of the 1-butene stream produced in the second hydrogenation unit through a separation unit producing a separated 1-butene stream; and

passing the separated 1-butene stream produced in the separation unit through a hydration unit producing the fuel additive,

wherein

the distillation unit comprises a kinetic distillation column,

the method further comprises withdrawing an iso-stream from the distillation unit, passing a raw material stream comprising hydrocarbons through a hydrocarbon cracking unit, withdrawing the feed stream from the cracking unit, and recycling the iso-stream back to the raw material stream, wherein the iso-stream comprises isobutane and isobutylene, and wherein the iso-stream comprises greater than or equal to 90% by weight isobutane and/or isobutylene, based on the total weight of the iso-stream,

the method further comprises withdrawing an iso-stream from the distillation unit, and passing the iso-stream through a propylene and/or ethylene cracking unit, wherein the iso-stream comprises isobutane and isobutylene, and wherein the iso-stream comprises greater than or equal to 90% by weight isobutane and/or isobutylene, based on the total weight of the iso-stream, or

the method further comprises withdrawing a butane stream comprising n-butane and/or isobutane from the separation unit and passing the butane stream through a propylene and/or ethylene cracking unit.

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

3. The method of claim 1 , wherein the feed stream comprises at least one of methyl acetylene, propylene, 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 , wherein the distillation unit comprises a kinetic distillation column.

5. The method of claim 1 , wherein the feed stream comprises butadiene and greater than or equal to 85% by weight of the butadiene present in the feed stream, based on the total weight of the butadiene present in the feed stream, is converted to 1-butene and/or 2-butene within the first hydrogenation unit.

6. The method of claim 1 , further comprising passing a water stream through the hydration unit.

7. The method of claim 1 , further comprising adding tertiary butyl catechol and/or hydrogen to the feed stream prior to passing through the first hydrogenation unit.

8. The method of claim 1 , further comprising withdrawing an iso-stream from the distillation unit, wherein the iso-stream comprises isobutane and isobutylene, and wherein the iso-stream comprises greater than or equal to 90% by weight isobutane and/or isobutylene, based on the total weight of the iso-stream.

9. The method of claim 8 , further comprising passing a raw material stream comprising hydrocarbons through a hydrocarbon cracking unit, withdrawing the feed stream from the cracking unit, and recycling the iso-stream back to the raw material stream.

10. The method of claim 8 , further comprising passing the iso-stream through a propylene and/or ethylene cracking unit.

11. The method of claim 8 , further comprising passing the iso-stream through the hydration unit.

12. The method of claim 1 , further comprising recycling at least a portion of the 1-butene stream back to the distillation unit.

13. The method of claim 1 , further comprising withdrawing a butane stream comprising n-butane and/or isobutane from the separation unit and passing the butane stream through a propylene and/or ethylene cracking unit.

14. The method of claim 1 , wherein the hydration unit comprises an oscillating baffle reactor, a fixed bed reactor, a fluidized bed reactor, a membrane integrated reactor, or a combination thereof.

15. The method of claim 1 , wherein the 1-butene stream comprises butene and greater than or equal to 0.1% by weight of the butene present in the 1-butene stream, based on the total weight of the butene present in the 1-butene stream, is converted to butanol within the hydration unit.

16. The method of claim 1 , further comprising 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 C 4 dimer.

17. The method of claim 16 , wherein the fuel additive product comprises greater than or equal to 0.01% by weight and less than or equal to 20% by weight trimethylpentane based on the total weight of the fuel additive product, and the total weight of the fuel additive product is 100% by weight.

18. The method of claim 16 , wherein an octane number of the fuel additive product is greater than or equal to 85 in accordance with the Anti-Knock Index, and wherein a Reid vapor pressure of the fuel additive product is less than or equal to 75 kilopascals.

19. A method of producing a fuel additive, comprising:

passing a feed stream comprising C 4 hydrocarbons through a first hydrogenation unit producing a first process stream, wherein greater than or equal to 90% by weight of butadiene present in the feed stream, based on the total weight of the butadiene present in the feed stream, is converted to 1-butene and/or 2-butene within the first hydrogenation unit;

passing the first process stream through a distillation unit and withdrawing a 2-butene stream from the distillation unit;

passing the 2-butene stream through a second hydrogenation unit producing a 1-butene stream;

recycling at least a portion of the 1-butene stream back to the distillation unit;

passing at least a portion of the 1-butene stream through a separation unit and through a hydration unit; and

withdrawing a fuel additive product from the hydration unit, wherein the fuel additive product comprises greater than or equal to 0.5% by weight trimethylpentane based on the total weight of the fuel additive product, and the total weight of the fuel additive product is 100% by weight.

20. A method of producing a fuel additive, comprising:

passing a feed stream comprising C 4 hydrocarbons through a first hydrogenation unit producing a first process stream;

passing the first process stream through a distillation unit;

withdrawing a 2-butene stream from the distillation unit;

passing the 2-butene stream through a second hydrogenation unit producing a 1-butene stream;

passing at least a portion of the 1-butene stream through a separation unit; and

passing the 1-butene stream through a hydration unit producing the fuel additive,

wherein

the distillation unit comprises a kinetic distillation column,

the method further comprises passing a raw material stream comprising hydrocarbons through a hydrocarbon cracking unit, withdrawing the feed stream from the cracking unit, withdrawing an iso-stream from the distillation unit, wherein the iso-stream comprises isobutane and isobutylene, and recycling the iso-stream back to the raw material stream,

the method further comprises withdrawing an iso-stream from the distillation unit, wherein the iso-stream comprises isobutane and isobutylene, and passing the iso-stream through a propylene and/or ethylene cracking unit,

the method further comprises withdrawing a butane stream comprising n-butane and/or isobutane from the separation unit and passing the butane stream through a propylene and/or ethylene cracking unit,

the method further comprises 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 C 4 dimer and the fuel additive product comprises greater than or equal to 0.01% by weight and less than or equal to 20% by weight trimethylpentane based on the total weight of the fuel additive product, and the total weight of the fuel additive product is 100% by weight, or

a combination thereof.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 8, 2021
From: LEAL, GUILLERMO; AL-OTAIBI, NAIF MOHAMMED AL-NADDAH; ANSARI, MOHAMMED BISMILLAH; BODAS, VIJAY DINKAR
To: SABIC GLOBAL TECHNOLOGIES B.V.
Reel/Frame 057408/0539 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 8, 2021
From: SHAIK, KAREEMUDDIN MAHABOOB
To: SAUDI ARABIAN OIL COMPANY
Reel/Frame 057408/0570 →
Continuity (2)
Provisional Application 62815512 · Mar 8, 2019
Related Publication 20220185750A1 · Jun 16, 2022
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