Hydrodearylation Reactor

Patent metadata

Field	Value
Publication number	US-2021106971-A1
Application number	US-201916597752-A
Country	US
Kind code	A1
Filing date	Oct 9, 2019
Priority date	Oct 9, 2019
Publication date	Apr 15, 2021
Grant date	—

Abstract

A system and method including providing a feed having alkyl-bridged multi-aromatic compounds to a tubular reactor, heating the tubular reactor, and cleaving an alkyl bridge of the alkyl-bridged multi-aromatic compounds.

First claim

What is claimed is:

1 . A method of processing alkyl-bridged multi-aromatic compounds, comprising:
providing a feed comprising an alkyl-bridged multi-aromatic compound to a coiled tubular reactor, the alkyl-bridged multi-aromatic compound comprising a first aromatic ring coupled via an alkyl bridge to a second aromatic ring, wherein the alkyl bridge comprises at least two carbons; heating the coiled tubular reactor; and cleaving the alkyl bridge in the coiled tubular reactor to separate the alkyl-bridged multi-aromatic compound into a first aromatic compound comprising the first aromatic ring and a second aromatic compound comprising the second aromatic ring.

2 . The method of claim 1 , comprising flowing a reaction mixture comprising the feed and hydrogen through the coiled tubular reactor, wherein cleaving the alkyl bridge in the coiled tubular reactor is performed in absence of catalyst in the coiled tubular reactor, and wherein cleaving the alkyl bridge comprises breaking a bond between two carbons of the at least two carbons.

3 . The method of claim 1 , wherein the feed comprises hydrogen, wherein cleaving the alkyl bridge is performed in presence of hydrogen, and wherein residence time of a reaction mixture comprising the alkyl-bridged multi-aromatic compound and hydrogen in the coiled tubular reactor is less than 60 seconds.

4 . The method of claim 1 , wherein heating the coiled tubular reactor comprises heating the coiled tubular reactor with a furnace, wherein at least a portion of the coiled tubular reactor is disposed in the furnace, wherein an operating temperature of the coiled tubular reactor is at least 550° C., and wherein cleaving the alkyl bridge comprises hydrodearylation.

5 . The method of claim 1 , comprising performing hydrodealkylation on mono-aromatic compounds in the coiled tubular reactor in presence of hydrogen, wherein the mono-aromatic compounds comprise the first aromatic compound or the second aromatic compound, or both, and wherein the mono-aromatics comprise mono-aromatic compounds from the feed.

6 . The method of claim 1 , comprising preheating the feed in a heat exchanger upstream of the coiled tubular reactor or in an inlet portion of the coiled tubular reactor, or both, wherein the coiled tubular reactor comprises coiled piping, and wherein the inlet portion comprises straight piping upstream of the coiled piping.

7 . The method of claim 6 , comprising discharging an effluent from the coiled tubular reactor to a separation system comprising a separation vessel, wherein average molecular weight of compounds in the effluent is less than average molecular weight of compounds in the feed, and wherein preheating comprises heating the feed in the heat exchanger with the effluent.

8 . The method of claim 1 , comprising:
discharging a product effluent from the coiled tubular reactor, wherein heating the coiled tubular reactor comprises heating contents of the coiled tubular reactor to a temperature in a range of 450° C. to 600° C., and wherein cleaving the alkyl bridge comprises hydrodearylation; introducing the product effluent to a second coiled tubular reactor; heating contents of the second coiled tubular reactor to greater than 600° C.; and performing hydrodealkylation on aromatic compounds in the second coiled tubular reactor.

9 . A method of processing alkyl-bridged multi-aromatic compounds, comprising:
feeding alkyl-bridged multi-aromatic compounds each comprising an alkyl bridge to a coiled tubular reactor, wherein the coiled tubular reactor does not comprise catalyst; feeding hydrogen to the coiled tubular reactor; providing heat from a furnace to heat the coiled tubular reactor, wherein at least a portion of the coiled tubular reactor is disposed in the furnace; and performing hydrodearylation on the alkyl-bridged multi-aromatic compounds in the coiled tubular reactor via the hydrogen and via the heat provided by the furnace, the hydrodearylation comprising breaking a carbon-carbon bond of the alkyl bridge of at least some of the alkyl-bridged multi-aromatic compounds.

10 . The method of claim 9 , comprising:
performing hydrodealkylation on aromatic compounds in the coiled tubular reactor; operating the coiled tubular reactor as a continuous reactor, wherein residence time through the coiled tubular reactor is less than 100 seconds; and discharging a product effluent from the coiled tubular reactor.

11 . The method of claim 9 , comprising feeding steam to the coiled tubular reactor, thereby reducing coke formation in the coiled tubular reactor or reducing plugging of the coiled tubular reactor, or both.

12 . The method of claim 9 , comprising feeding at least one of alkyl sulfide or disulfides to the coiled tubular reactor, or both, thereby reducing coke formation in the coiled tubular reactor.

13 . A method of operating a hydrodearylation reactor, comprising:
preheating a hydrocarbon feed comprising alkyl-bridged multi-aromatic compounds; flowing the hydrocarbon feed and hydrogen through a coiled tubular reactor; heating the coiled tubular reactor with a furnace, wherein at least a portion of the coiled tubular reactor is disposed in the furnace; breaking a carbon-carbon bond of an alkyl bridge in the coiled tubular reactor in absence of catalyst; and discharging an effluent from the coiled tubular reactor.

14 . The method of claim 13 , wherein heating the coiled tubular reactor with the furnace comprises heating contents of the coiled tubular reactor to at least 550° C., and wherein residence time through the coiled tubular reactor is less than 50 seconds.

15 . The method of claim 13 , comprising injecting steam into the hydrocarbon feed or directly into the coiled tubular reactor, or both, thereby reducing coke formation in the coiled tubular reactor or reducing plugging of the coiled tubular reactor, or both, wherein preheating the hydrocarbon feed comprises heating the hydrocarbon feed with the effluent.

16 . The method of claim 13 , comprising adding at least one of alkyl sulfide or disulfides to the hydrocarbon feed or directly to the coiled tubular reactor, or both, thereby reducing coke formation in the coiled tubular reactor and protecting an interior metal surface of the coiled tubular reactor.

17 . The method of claim 13 , comprising performing hydrodealkylation in the coiled tubular reactor, wherein heating the coiled tubular reactor with the furnace comprises the preheating of the hydrocarbon feed in a straight-run section of the coiled tubular reactor disposed in the furnace.

18 . A method of operating a hydrodearylation reactor system, comprising:
providing a feed comprising an alkyl-bridged multi-aromatic compound to a first coiled tubular reactor, the alkyl-bridged multi-aromatic compound comprising a first aromatic ring coupled via an alkyl bridge to a second aromatic ring, wherein the alkyl bridge comprises at least two carbons; heating contents of the first coiled tubular reactor to a first temperature in a range of 450° C. to 600° C.; cleaving the alkyl bridge in the first coiled tubular reactor to separate the alkyl-bridged multi-aromatic compound into a first aromatic compound comprising the first aromatic ring and a second aromatic compound comprising the second aromatic ring, wherein cleaving the alkyl bridge comprises hydrodearylation; and introducing a product effluent from the first coiled tubular reactor to a second coiled tubular reactor; and heating contents of the second coiled tubular reactor to a second temperature greater than

Assignees

• Saudi Arabian Oil Co

Inventors

• Koseoglu Omer Refa
• Hodgkins Robert Peter

Classifications

• C07C4/14

  splitting taking place at an aromatic-aliphatic bond · CPC title

• C07C4/12

  from hydrocarbons containing a six-membered aromatic ring, e.g. propyltoluene to vinyltoluene · CPC title

• C07C4/16

  Thermal processes · CPC title

• C07C4/24

  by splitting polyarylsubstituted aliphatic compounds at an aliphatic-aliphatic bond, e.g. 1,4-diphenylbutane to styrene · CPC title

• B01J19/243 Primary

  spirally, concentrically or zigzag wound · CPC title