Producing c5 olefins from steam cracker c5 feeds

Patent metadata

Field	Value
Publication number	US-2019232249-A1
Application number	US-201916379414-A
Country	US
Kind code	A1
Filing date	Apr 9, 2019
Priority date	Jan 29, 2015
Publication date	Aug 1, 2019
Grant date	—

Abstract

Producing C5 olefins from steam cracker C5 feeds may include reacting a mixed hydrocarbon stream comprising cyclopentadiene, C5 olefins, and C6+ hydrocarbons in a dimerization reactor where cyclopentadiene is dimerized to dicyclopentadiene. The dimerization reactor effluent may be separated into a fraction comprising the C6+ hydrocarbons and dicyclopentadiene and a second fraction comprising C5 olefins and C5 dienes. The second fraction, a saturated hydrocarbon diluent stream, and hydrogen may be fed to a catalytic distillation reactor system for concurrently separating linear C5 olefins from saturated hydrocarbon diluent, cyclic C5 olefins, and C5 dienes contained in the second fraction and selectively hydrogenating C5 dienes. An overhead distillate including the linear C5 olefins and a bottoms product including cyclic C5 olefins are recovered from the catalytic distillation reactor system. Other aspects of the C5 olefin systems and processes, including catalyst configurations and control schemes, are also described.

First claim

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27 . A process for producing C5 olefins from a mixed C5 feed, the process comprising:
feeding hydrogen and a mixed hydrocarbon stream comprising cyclopentadiene, linear C5 olefins, cyclic C5 olefins, and C6+ hydrocarbons to a catalytic distillation reactor system; concurrently in the catalytic distillation reactor system:
separating the linear C5 olefins from the cyclic C5 olefins, C5 dienes, and C6 + hydrocarbons; and
selectively hydrogenating at least a portion of the C5 dienes to form additional linear C5 olefins;
withdrawing a liquid side draw from a stage below a mixed hydrocarbon feed location and a hydrogen feed location and above a main reboiler, at least partially vaporizing the liquid side draw in an intermediate reboiler, and returning the at least partially vaporized liquid side draw to the catalytic distillation reactor system; recovering linear C5 olefins as an overhead distillate from the catalytic distillation reactor system; and recovering cyclic C5 olefins as a bottoms product from the catalytic distillation reactor system.

28 . The process of claim 27 , further comprising operating the main reboiler of the catalytic distillation reactor system at a temperature of less than about 302° F.

29 . A process for the selective hydrogenation of C5 dienes in a mixed C5 hydrocarbon stream, comprising:
feeding hydrogen and a C5 olefin containing stream comprising linear pentenes, dienes, acetylenes, and a diluent compound to a catalytic distillation reactor system; concurrently in the catalytic distillation reactor system:
hydrogenating the acetylenes and dienes; and
fractionating the C5-olefin containing stream;
recovering an overheads fraction comprising the pentenes, recovering a bottoms fraction; wherein the catalytic distillation reactor system has at least three reaction zones, including:
a first reaction zone disposed below a C5-olefin containing stream feed elevation and containing a nickel-based catalyst;
a second reaction zone disposed above the C5-olefin containing stream feed elevation and containing a nickel-based catalyst; and
a third reaction zone disposed above the second reaction zone and containing a palladium-based catalyst.

30 . The process of claim 29 , wherein the nickel-based catalyst comprises from about 5 wt % to about 30 wt % nickel, wherein the nickel-based catalyst is disposed on a diatomaceous earth support, has a BET surface area in the range from about 20 m 2 /g to about 400 m 2 /g, and has a pore volume in the range from about 0.2 ml/g to about 0.7 ml/g, and wherein the palladium-based catalyst comprises from about 0.2 to about 1.0 wt % palladium disposed on an alumina support.

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36 . A process for the selective hydrogenation of C5 dienes in a mixed C5 hydrocarbon stream, comprising:
feeding hydrogen and a C5-olefin containing stream comprising linear pentenes, dienes, acetylenes, and a diluent compound to a catalytic distillation reactor system; concurrently in the catalytic distillation reactor system:
hydrogenating the acetylenes and dienes; and
fractionating the C5-olefin containing stream;
recovering an overheads fraction comprising the pentenes; recovering a bottoms fraction; determining a concentration of the diluent compound at one or more column elevations; and adjusting one or more column operating parameters to maintain a set point concentration or a concentration profile of the diluent compound at the one or more column elevations.

37 . The process of claim 36 , wherein the catalytic distillation reactor system includes an upper catalyst zone above a C5-olefin containing stream feed elevation and a lower catalyst zone below the C5-olefin containing stream feed elevation, the process comprising at least one of:
measuring a concentration of the diluent compound at an elevation below the lower catalyst zone; measuring a concentration of the diluent compound at an elevation intermediate the upper and lower catalyst zones; or measuring a concentration of the diluent compound at an elevation above the upper catalyst zone.

38 . The process of claim 36 , wherein the catalytic distillation reactor system includes an upper catalyst zone above a C5-olefin containing stream feed elevation and a lower catalyst zone below the C5-olefin containing stream feed elevation, the process comprising at least one of:
measuring a density of a liquid fraction at an elevation below the lower catalyst zone and determining the concentration of the diluent compound at the elevation below based upon the measured density; measuring a density of a liquid fraction at an elevation intermediate the upper and lower catalyst zones and determining the concentration of the diluent compound at the elevation intermediate based upon the measured density; or measuring a density of a liquid fraction at an elevation above the upper catalyst zone and determining the concentration of the diluent compound at the elevation above based upon the measured density.

39 . The process of claim 36 , wherein the diluent compound comprises cyclopentane, cyclopentene, or a combination thereof.

40 . The process of claim 36 , wherein the diluent compound comprises one or more hydrocarbons having a normal boiling point in the range from about 100° F. to about 125° F.

41 . The process of claim 36 , wherein the diluent compound comprises one or more hydrocarbons having a specific gravity in the range from about 0.7 to about 0.8.

42 . The process of claim 36 , wherein a sample elevation used in the determining step is disposed proximate an elevation of maximum rate of change in concentration of the diluent compound within the catalytic distillation reactor system.

43 . The process of claim 42 , further comprising determining an elevation of maximum rate of change in concentration of the diluent compound within the catalytic distillation reactor system.

44 . The process of claim 36 , wherein the adjusting comprises at least one of:
decreasing an overhead flow and increasing a reflux flow when a diluent compound concentration profile starts to move up the column and the reflux flow is below a column flooding value; increasing an overhead flow and decreasing reflux flow when a diluent compound concentration profile starts to move down the column and the reflux flow is above a minimum design value; decreasing a reboiler duty and an overhead flow when the diluent compound concentration profile starts to move up the column; or increasing a reboiler duty and an overhead flow when

Assignees

• Lummus Technology Inc

Inventors

• Xu Yongqiang
• Loezos Peter
• Groten Willibrord A
• Lemoine Romain

Classifications

• C07C7/177

  by selective oligomerisation or polymerisation of at least one compound of the mixture · CPC title

• C07C6/04 Primary

  at a carbon-to-carbon double bond · CPC title

• C07C7/167

  for removal of compounds containing a triple carbon-to-carbon bond · CPC title

• C10G50/00

  Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation · CPC title

• C10G9/36

  with heated gases or vapours · CPC title