Method for production of conjugated diolefin

Patent metadata

Field	Value
Publication number	US-10329224-B2
Application number	US-201214383479-A
Country	US
Kind code	B2
Filing date	Mar 13, 2012
Priority date	Mar 13, 2012
Publication date	Jun 25, 2019
Grant date	Jun 25, 2019

Abstract

An object of the present invention is to provide a method for production of a high purity conjugated diolefin. The method for production of a conjugated diolefin of the present invention comprises steps of supplying a source gas containing a C4 or higher monoolefin and an oxygen-containing gas into a reactor, bringing a catalyst into contact with the gas mixture, compressing a gas containing a conjugated diolefin produced by an oxidative dehydrogenation reaction to obtain a liquefied gas and rinsing the liquefied gas with water.

First claim

What is claimed is:

1. A method for production of a conjugated diolefin, wherein said method comprises the following steps of (1) to (6) in this order:
step (1): a step of supplying a source gas containing a C4 or higher monoolefin and an oxygen-containing gas into a reactor to form a gas mixture and bringing a catalyst into contact with the gas mixture to obtain a gas containing a conjugated diolefin by an oxidative dehydrogenation reaction,
step (2): a step of cooling the gas containing the conjugated diolefin in a quench column,
step (3): a step of allowing the gas containing the conjugated diolefin to be absorbed in a solvent, subsequently stripping the gas containing the conjugated diolefin from the solvent, followed by compressing the gas to obtain a liquefied gas, wherein the solvent for absorbing the gas containing the conjugated diolefin is toluene, m-xylene, o-xylene, p-xylene, or mixed xylene,
step (4): a step of rinsing the liquefied gas with water,
step (5): a step of removing the water from the liquefied gas by distillation, and
step (6): a step of removing a high boiling component from the liquefied gas, wherein
in the step (1), an oxygen concentration of the gas containing the conjugated diolefin is in a range of 0.01 to 2.0% by volume.

2. The method for production of the conjugated diolefin according to claim 1 ,
wherein the liquefied gas obtained in the step (3) contains acetaldehyde, and
the acetaldehyde is dissolved in the water in the step (4).

3. The method for production of the conjugated diolefin according to claim 1 , further comprising, before the step (4) and/or after the step (6), a step of:
allowing the liquefied gas to be absorbed in a high polarity solvent having a higher polarity than the solvent of the step (3), subsequently stripping the gas containing the conjugated diolefin from the high polarity solvent, followed by compressing the gas to obtain a liquefied gas.

4. The method for production of the conjugated diolefin according to claim 3 , wherein the high polarity solvent contains at least one selected from the group consisting of N-alkyl-substituted lower fatty acid amide, a nitrile compound and a heterocyclic compound.

5. The method for production of the conjugated diolefin according to any one of claims 1 and 2 - 4 , wherein the source gas contains n-butene.

6. The method for production of the conjugated diolefin according to claim 1 ,
wherein the source gas and the oxygen-containing gas are independently supplied into the reactor in the step (1).

7. The method for production of the conjugated diolefin according to claim 1 ,
wherein the catalyst is represented by a following formula:
Mo 12 Bi p Fe q A a B b C c D d E e O x ,

where A is at least one element selected from the group consisting of nickel and cobalt; B is at least one element selected from the group consisting of alkali metal elements; C is at least one element selected from the group consisting of magnesium, calcium, strontium, barium, zinc, and manganese; D is at least one rare earth element; E is at least one element selected from the group consisting of chromium, indium, and gallium; O is oxygen; p, q, a, b, c, d, e, and x represent an atomic ratio of bismuth, iron, A, B, C, D, E, and oxygen, respectively, to 12 molybdenum atoms; 0.1≤p≤5, 0.5≤q≤8, 0.1≤a≤10, 0.02≤b≤2, 0≤c≤5, 0≤d≤5, and 0≤e≤5 are satisfied; and x is an atomic number of oxygen required for satisfying a valence requirement of the other elements.

8. The method for production of the conjugated diolefin according to claim 1 , wherein the step (4) of rinsing the liquefied gas with water is performed at an operation temperature of 5 to 45° C.

9. The method for production of the conjugated diolefin according to claim 1 , wherein the solvent for absorbing the gas containing the conjugated diolefin is m-xylene, o-xylene, p-xylene, or mixed xylene.

10. The method for production of the conjugated diolefin according to claim 1 , wherein the step (4) of rinsing the liquefied gas with water is operated at a pressure of 0.25 to 0.7 MPaG.

11. The method for production of the conjugated diolefin according to claim 1 , wherein the step (5) of removing the water from the liquefied gas by distillation is operated at a pressure of 0.3 to 0.7 MPaG.

12. The method for production of the conjugated diolefin according to claim 1 , wherein the step (5) of removing the water from the liquefied gas by distillation is operated at a column top temperature of 40 to 60° C. and a column bottom temperature of 45 to 65° C.

13. The method for production of the conjugated diolefin according to claim 1 , wherein the step (5) of removing the water from the liquefied gas by distillation is performed in a packed column or a plate column.

14. The method for production of the conjugated diolefin according to claim 1 , wherein the step (5) of removing the water from the liquefied gas by distillation further comprises adding a polymerization inhibitor.

15. The method for production of the conjugated diolefin according to claim 14 , wherein the polymerization inhibitor comprises at least one of hydroquinone, 4-methoxyphenol, phenothiazine, 2,6-di-tert-butyl-p-cresol, 2,6-di-tert-butylhydroquinone, 4-tert-butylcatechol, and bisphenol A.

16. The method for production of the conjugated diolefin according to claim 1 , wherein the step (6) of removing the high boiling component from the liquefied gas is operated at a pressure of 0.25 to 0.7 MPaG.

17. The method for production of the conjugated diolefin according to claim 1 , wherein the step (6) of removing the high boiling component from the liquefied gas is operated at a column top temperature of 40 to 60° C. and a column bottom temperature of 50 to 70° C.

18. The method for production of the conjugated diolefin according to claim 1 , wherein the step (6) of removing the high boiling component from the liquefied gas is performed in a packed column or a plate column.

19. The method for production of the conjugated diolefin according to claim 1 , wherein the step (6) of removing the high boiling component from the liquefied gas further comprises adding a polymerization inhibitor.

20. The method for production of the conjugated diolefin according to claim 19 , wherein the polymerization inhibitor comprises at least one of hydroquinone, 4-methoxyphenol, phenothiazine, 2,6-di-tert-butyl-p-cresol, 2,6-di-tert-butylhydroquinone, 4-tert-butylcatechol, and bisphenol A.

Assignees

• Takagaki Kazuhiro
• Yano Hiroyuki
• Asahi Kasei Chemicals Corp

Inventors

• Takagaki Kazuhiro
• Yano Hiroyuki

Classifications

• B01J2523/00

  Constitutive chemical elements of heterogeneous catalysts · CPC title

• C07C2523/10

  of rare earths · CPC title

• B01J23/8872

  Alkali or alkaline earth metals · CPC title

• C07C2523/755

  Nickel · CPC title

• C07C2521/08

  Silica · CPC title