Process for preparing 1,3-butadiene from n-butenes by oxidative dehydrogenation

Patent metadata

Field	Value
Publication number	US-10308569-B2
Application number	US-201515514077-A
Country	US
Kind code	B2
Filing date	Sep 14, 2015
Priority date	Sep 26, 2014
Publication date	Jun 4, 2019
Grant date	Jun 4, 2019

Abstract

The invention relates to a process for preparing butadiene from n-butenes, comprising the steps of:
A) providing an input gas stream a comprising n-butenes, B) feeding the input gas stream a comprising n-butenes and a gas containing at least oxygen into at least one oxidative dehydrogenation zone and oxidatively dehydrogenating n-butenes to butadiene, giving a product gas stream b comprising butadiene, unconverted n-butenes, water vapor, oxygen, low-boiling hydrocarbons and high-boiling secondary components, with or without carbon oxides and with or without inert gases; Ca) cooling the product gas stream b by contacting with a cooling medium in at least one cooling zone, the cooling medium being at least partly recycled and having an aqueous phase and an organic phase, Cb) compressing the cooled product gas stream b which may have been depleted of high-boiling secondary components in at least one compression stage, giving at least one aqueous condensate stream c1 and one gas stream c2 comprising butadiene, n-butenes, water vapor, oxygen and low-boiling hydrocarbons, with or without carbon oxides and with or without inert gases; D) removing uncondensable and low-boiling gas constituents comprising oxygen and low-boiling hydrocarbons, with or without carbon oxides and with or without inert gases, as gas stream d2 from the gas stream c2 by absorbing the C 4 hydrocarbons comprising butadiene and n-butenes in an absorbent, giving an absorbent stream laden with C 4 hydrocarbons and the gas stream d2, and then desorbing the C 4 hydrocarbons from the laden absorbent stream, giving a C 4 product gas stream d1, E) separating the C 4 product stream d1 by extractive distillation with a butadiene-selective solvent into a stream e1 comprising butadiene and the selective solvent and a stream e2 comprising n-butenes; F) distilling the stream e1 comprising butadiene and the selective solvent into a stream f1 consisting essentially of the selective solvent and a stream f2 comprising butadiene,
wherein stage Cb) comprises at least two compression stages Cba) and at least two cooling stages Cbb) configured in the form of quench columns, the cooling in the cooling stages being effected by direct contacting with a biphasic cooling medium having an aqueous phase and an organic phase.

First claim

The invention claimed is:

1. A process for preparing butadiene from n-butenes, comprising the steps of:
A) providing an input gas stream a comprising n-butenes,
B) feeding the input gas stream a comprising n-butenes and a gas containing at least oxygen into at least one oxidative dehydrogenation zone and oxidatively dehydrogenating n-butenes to butadiene, giving a product gas stream b comprising butadiene, unconverted n-butenes, water vapor, oxygen, low-boiling hydrocarbons and high-boiling secondary components, with or without carbon oxides and with or without inert gases;
Ca) cooling the product gas stream b by contacting with a cooling medium in at least one cooling zone to form a cooled product gas stream depleted of high-boiling secondary components, the cooling medium being at least partly recycled and, having an aqueous phase and an organic phase,
Cb) compressing the cooled product gas stream depleted of high-boiling secondary components in at least one compression stage, giving at least one aqueous condensate stream c1 and one gas stream c2 comprising butadiene, n-butenes, water vapor, oxygen and low-boiling hydrocarbons, with or without carbon oxides and with or without inert gases;
D) removing uncondensable and low-boiling gas constituents comprising oxygen and low-boiling hydrocarbons, with or without carbon oxides and with or without inert gases, as gas stream d2, and then desorbing the C 4 hydrocarbons from the absorbent stream laden with C 4 hydrocarbons giving C 4 product gas stream d1,
E) separating the C 4 product gas stream d1 by extractive distillation with a butadiene-selective, solvent into a stream e1 comprising butadiene and the selective solvent and a stream e2 comprising n-butenes;
F) distilling the stream e1 comprising butadiene and the selective solvent into a stream f1 consisting essentially of the selective solvent and a stream f2 comprising butadiene,
wherein stage the step Cb) comprises at least two compression stages Cba) and at least two cooling stages Cbb) configured in the form of quench columns, cooling in the at least two cooling stages Cbb) being effected in cooling zones by direct contacting the cooled products gas stream with a biphasic cooling medium having an aqueous phase and an organic phase formed from an organic solvent, wherein the organic solvent is selected from the group consisting of toluene, o-, m- and p-xylene, mesitylene, mono-, di- and triethylbenzene,mono-, di- and triisopropylbenzene and mixtures thereof, and wherein in the at least two cooling stages Cbb), a mass ratio of the aqueous phase to the organic phase in the biphasic cooling medium when it is fed into the cooling zones prior to the contacting with the cooled product gas stream is from 0.15:1 to 10:1 and wherein a coolant having an aqueous phase and an organic phase is fed continuouslyor discontinuously into the at least two compression stages Cba), and wherein the coolant is fed into anintake line of at least one compressor of the at least two compression stages Cba) or into a housing of at leastone compressor of the at least two compression stages Cba).

2. The process according to claim 1 , wherein the step Cb) comprises at least three compression stages Cba) and at least three cooling stages Cbb).

3. The process according to claim 2 , wherein the step Ca) is conducted in three stages Ca1), Ca2) and Ca3) in three cooling zones.

4. The process according to claim 3 , wherein the step D) comprises stages Da) to Dc):
Da) absorbing the C 4 hydrocarbons comprising butadiene and n-butenes in a high-boiling absorbent, giving the absorbent stream laden with C 4 hydrocarbons and the gas stream d2,
Db) removing oxygen from the absorbent stream laden with C 4 hydrocarbons from the stage Da) by stripping with an uncondensable gas stream, and
Dc) desorbing the C 4 hydrocarbons from the absorbent stream laden with C 4 hydrocarbons, giving the C 4 product gas stream d1 comprising less than 100 ppmw of oxygen.

Assignees

• Basf Se
• Linde Ag

Inventors

• Josch Jan Pablo
• Grüne Philipp
• Benfer Regina
• Vicari Maximilian
• Biegner Andre
• BLOCH Gergor
• Boelt Heinz
• Reyneke Hendrik
• Toegel Christine
• Wenning Ulrike

Classifications

• C07C7/08

  by extractive distillation · CPC title

• C07C5/333

  Catalytic processes · CPC title

• C07C7/05

  with the aid of auxiliary compounds · CPC title

• C07C5/48 Primary

  with oxygen as an acceptor · CPC title

• B01D3/40

  Extractive distillation · CPC title