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Patent · US9758446B2 · B2 · US

Selective hydrogenation using a flow index

(11) Publication number
US9758446B2
(21) Application number
14/942,816
(22) Filing date
2015-11-16
(30) Priority date
2015-11-16
(43) Publication date
2017-09-12
(45) Date of grant
2017-09-12
(51) IPC
B01J 19/24; C07C 4/04; C07C 5/03; C07C 5/05; C07C 5/09; C10G 45/32; C10G 69/06; C10G 70/02; C10G 9/00
(52) CPC
  • C10G Cracking hydrocarbon oils; production of liquid hydrocarbon mixtures, e.g. by destructive hydrogenation, oligomerisation, polymerisation; recovery of hydrocarbon oils from oil-shale, oil-sand, or gases; refining mixtures mainly consisting of hydrocarbons; reforming of naphtha; mineral waxes: 45/32, 2400/20, 2400/24, 69/06, 70/02, 9/00
  • B01J Chemical or physical processes, e.g. catalysis or colloid chemistry; their relevant apparatus: 19/24, 19/245, 2219/00306, 2219/24
  • B65G Transport or storage devices, e.g. conveyors for loading or tipping, shop conveyor systems or pneumatic tube conveyors: 1/045, 1/0492, 1/065, 1/10, 1/127, 1/137, 1/1371, 1/1373, 1/1378, 47/57
  • C07C Acyclic or carbocyclic compounds: 2521/04, 4/04, 5/05, 5/09
  • Y10S Technical subjects covered by former uspc cross-reference art collections [xracs] and digests: 901/01
(73) Assignee
CHEVRON PHILLIPS CHEMICAL CO LP
(72) Inventors
BERGMEISTER III JOSEPH; CHEUNG TIN-TACK PETER; HONG ZONGXUAN; ODI TIMOTHY O; NOLIDIN CHARLES D; GONZALES THOMAS J; NILL JENNIFER L; DOCKTER DAVID W
(54) Title
Selective hydrogenation using a flow index
(57) Abstract

A process includes hydrogenating, in a reaction zone, a highly unsaturated hydrocarbon received from a hydrocarbon stream to yield a product having an unsaturated hydrocarbon, the hydrogenating step occurring in the presence of a hydrogenation catalyst which has a selectivity for conversion of the highly unsaturated hydrocarbon to the unsaturated hydrocarbon of about 90 mol % or greater based on the moles of the highly unsaturated hydrocarbon which are converted to the product, the hydrogenating step occurring in a reaction zone under conditions which include a flow index (I F) in a range of about 0.09 to about 35, wherein the I F is defined as: I F = F × [CO] V, wherein F is the flow rate of the hydrocarbon stream into the reaction zone in units of kg/h, [CO] is the concentration of carbon monoxide in the hydrocarbon stream in units of mol %, and V is the volume of the reaction zone in units of ft 3.

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Claims (13)

  1. A process comprising: hydrogenating, in a reaction zone, a highly unsaturated hydrocarbon received from a hydrocarbon stream to yield a product comprising an unsaturated hydrocarbon, wherein the hydrogenating occurs in the presence of a hydrogenation catalyst which has a selectivity for conversion of the highly unsaturated hydrocarbon to the unsaturated hydrocarbon of about 90 mol % or greater based on the moles of the highly unsaturated hydrocarbon which are converted to the product, wherein the highly unsaturated hydrocarbon comprises acetylene, and wherein the unsaturated hydrocarbon comprises ethylene, and wherein the hydrogenating in the reaction zone occurs under conditions comprising a flow index (I F) in a range of about 0.09 to about 35, wherein the I F is defined as: I F = F × [CO] V, wherein F is the flow rate of the hydrocarbon stream into the reaction zone in units of kg/h, [CO] is the concentration of carbon monoxide in the hydrocarbon stream in units of mol %, and V is the volume of the reaction zone in units of ft 3.
  2. The process of claim 1, wherein the selectivity is defined as: S = 100 × (UH ⁡ (p) - UH ⁡ (f) HUH ⁡ (f) - HUH ⁡ (p)) where S is selectivity in mol %, UH(p) is moles of the unsaturated hydrocarbon in the product, UH(f)is moles of the unsaturated hydrocarbon in the hydrocarbon stream, HUH(f) is the moles of highly unsaturated hydrocarbon in the hydrocarbon stream, and HUH(p) is the moles of the highly unsaturated hydrocarbon in the product.
  3. The process of claim 1, wherein the highly unsaturated hydrocarbon further comprises methylacetylene, propadiene, or both; and wherein the unsaturated hydrocarbon further comprises propylene.
  4. The process of claim 1, further comprising: cracking a feed stream to produce a cracked gas stream comprising the highly unsaturated hydrocarbon, carbon monoxide, and a saturated hydrocarbon.
  5. The process of claim 4, further comprising: fractionating the cracked gas stream to yield a C 3 − stream or C 2 − stream comprising the highly unsaturated hydrocarbon, carbon monoxide, and about 90 mol % or greater of the saturated hydrocarbon contained in the cracked gas stream, wherein at least a portion of the highly unsaturated hydrocarbon in the C 3 − stream or the C 2 − stream is hydrogenated in the presence of the hydrogenation catalyst.
  6. The process of claim 1, wherein the [CO] in the reaction zone is from about 0.0001 mol % to about 0.15 mol %.
  7. The process of claim 1, wherein the hydrogenating step comprises: contacting the hydrogenation catalyst with at least a portion of the highly unsaturated hydrocarbon in the presence of hydrogen.
  8. The process of claim 1, wherein the reaction zone comprises a first stage and a second stage, wherein at least one of the first stage and the second stage of the reaction zone contains the hydrogenation catalyst.
  9. The process of claim 8, wherein: i) the first stage of the reaction zone and the second stage of the reaction zone are contained in a common vessel; or ii) the first stage of the reaction zone is a first reactor, the second stage of the reaction zone is a second reactor, and the first reactor and the second reactor are connected in series.
  10. A process comprising: cracking a feed stream to produce a cracked gas stream comprising acetylene, ethylene, ethane, methane, hydrogen, carbon monoxide, and C 3 + components; fractionating the cracked gas stream into a C 2 − stream and a C 3 + stream, wherein the C 2 − stream comprises acetylene, ethylene, ethane, methane, hydrogen, and carbon monoxide, wherein the C 3 + stream comprises the C 3 + components; hydrogenating at least a portion of the acetylene of the C 2 − stream in the presence of a hydrogenation catalyst to yield a product comprising ethylene, wherein the hydrogenation catalyst has a selectivity for conversion of acetylene to ethylene of about 90 mol % or greater based on the moles of acetylene which are converted to the product, wherein the hydrogenating occurs in a reaction zone under conditions comprising a flow index (I F) in a range of about 0.09 to about 35, wherein the I F is defined as: I F = F × [CO] V, wherein F is the flow rate of the C 2 − stream into the reaction zone in units of kg/h, [CO] is the concentration of carbon monoxide in the C 2 − stream in units of mol %, and V is the volume of the portion of the reaction zone in units of ft 3; removing ethylene from the product; and polymerizing ethylene into one or more polymer products.
  11. The process of claim 10, wherein the selectivity is defined as: S = 100 × (UH ⁡ (p) - UH ⁡ (f) HUH ⁡ (f) - HUH ⁡ (p)) where S is the selectivity in mol %, UH(p) is moles of ethylene in the product, UH(f) is moles of ethylene in the hydrocarbon stream, HUH(f) is the moles of acetylene in the hydrocarbon stream, and HUH(p) is the moles of acetylene in the product.
  12. A process comprising: cracking a feed stream to produce a cracked gas stream comprising a highly unsaturated hydrocarbon, carbon monoxide, and a saturated hydrocarbon; fractionating the cracked gas stream to yield a C 3 − stream or a C 2 − stream comprising the highly unsaturated hydrocarbon, carbon monoxide, and about 90 mol % or greater of the saturated hydrocarbon contain in the cracked gas stream, providing the C 3 − stream or a C 2 31 stream to a reaction zone comprising a hydrogenation catalyst, wherein at least a portion of the highly unsaturated hydrocarbon in the C 3 − stream or the C 2 − is hydrogenated in the presence of the hydrogenation catalyst; and hydrogenating, in the reaction zone, the highly unsaturated hydrocarbon to yield a product comprising an unsaturated hydrocarbon, wherein the hydrogenation catalyst has a selectivity for conversion of the highly unsaturated hydrocarbon to the unsaturated hydrocarbon of about 90 mol % or greater based on moles of the highly unsaturated hydrocarbon which are converted to the product, wherein the hydrogenating step occurs under conditions comprising a flow index (I F;) in a range of about 0.09 to about 35, wherein the I F is defined as: I F = F × [CO] V, wherein F is the flow rate of the hydrocarbon stream into the reaction zone in units of kg/h, [CO] is the concentration of carbon monoxide in the hydrocarbon stream in units of mol %, and V is the volume of the portion of the reaction zone in units of ft 3.
  13. The process of claim 12, wherein the selectivity is defined as: S = 100 × (UH ⁡ (p) - UH ⁡ (f) HUH ⁡ (f) - HUH ⁡ (p)) where S is the selectivity in mol %, UH(p) is moles of the unsaturated hydrocarbon in the product, UH(f) is moles of the unsaturated hydrocarbon in the hydrocarbon stream, HUH(f) is the moles of highly unsaturated hydrocarbon in the hydrocarbon stream, and HUH(p) is the moles of the highly unsaturated hydrocarbon in the product.

Description

Not applicable.

The present disclosure relates to the production of an unsaturated hydrocarbon, and more particularly to a hydrogenation of compounds using highly selective catalyst.

Unsaturated hydrocarbons such as ethylene and propylene are often employed as feedstocks in preparing value added chemicals and polymers. Unsaturated hydrocarbons can be produced by pyrolysis or cracking of hydrocarbons including hydrocarbons derived from coal, oil, gas, synthetic crude, naphthas, natural gas liquids, raffinate, refinery gases, ethane, propane, butane, and the like. Unsaturated hydrocarbons products produced in these manners usually contain highly unsaturated hydrocarbons such as acetylenes and diolefins that adversely affect the production of subsequent chemicals and polymers. Thus, to form an unsaturated hydrocarbon product such as a polymer grade monoolefin, the amount of acetylenes and diolefins in the monoolefin stream is typically reduced. One technique commonly used to reduce the amount of acetylenes and diolefins in an unsaturated hydrocarbon stream primarily comprising monoolefins involves hydrogenating the acetylenes and diolefins to monoolefins. This process is selective in that hydrogenation of a monoolefin and a highly unsaturated hydrocarbon to the saturated hydrocarbon is minimized. For example, the hydrogenation of ethylene or acetylene to ethane is minimized.

One challenge to the selective hydrogenation process is the potential for a runaway reaction which is uncontrolled hydrogenation of ethylene to ethane. One methodology to minimize runaway reactions is to use a highly selective hydrogenation catalyst.

Citations (18)

  • US2002004622A1
  • US2004192983A1
  • US2005256281A1
  • US2007161833A1
  • US2010228065A1
  • US2012209042A1
  • US2013172641A1
  • US4404124A
  • US4484015A
  • US4517395A
  • US5475173A
  • US5489565A
  • US5510550A
  • US5585318A
  • US5587348A
  • US7038096B2
  • US7141709B2
  • US8633127B2
Record as JSON 
{
  "publication_number": "US9758446B2",
  "country": "US",
  "kind": "B2",
  "title": "Selective hydrogenation using a flow index",
  "abstract": "A process includes hydrogenating, in a reaction zone, a highly unsaturated hydrocarbon received from a hydrocarbon stream to yield a product having an unsaturated hydrocarbon, the hydrogenating step occurring in the presence of a hydrogenation catalyst which has a selectivity for conversion of the highly unsaturated hydrocarbon to the unsaturated hydrocarbon of about 90 mol % or greater based on the moles of the highly unsaturated hydrocarbon which are converted to the product, the hydrogenating step occurring in a reaction zone under conditions which include a flow index (I F) in a range of about 0.09 to about 35, wherein the I F is defined as: I F = F × [CO] V, wherein F is the flow rate of the hydrocarbon stream into the reaction zone in units of kg/h, [CO] is the concentration of carbon monoxide in the hydrocarbon stream in units of mol %, and V is the volume of the reaction zone in units of ft 3.",
  "claims": [
    "1. A process comprising: hydrogenating, in a reaction zone, a highly unsaturated hydrocarbon received from a hydrocarbon stream to yield a product comprising an unsaturated hydrocarbon, wherein the hydrogenating occurs in the presence of a hydrogenation catalyst which has a selectivity for conversion of the highly unsaturated hydrocarbon to the unsaturated hydrocarbon of about 90 mol % or greater based on the moles of the highly unsaturated hydrocarbon which are converted to the product, wherein the highly unsaturated hydrocarbon comprises acetylene, and wherein the unsaturated hydrocarbon comprises ethylene, and wherein the hydrogenating in the reaction zone occurs under conditions comprising a flow index (I F) in a range of about 0.09 to about 35, wherein the I F is defined as: I F = F × [CO] V, wherein F is the flow rate of the hydrocarbon stream into the reaction zone in units of kg/h, [CO] is the concentration of carbon monoxide in the hydrocarbon stream in units of mol %, and V is the volume of the reaction zone in units of ft 3.",
    "2. The process of claim 1, wherein the selectivity is defined as: S = 100 × (UH ⁡ (p) - UH ⁡ (f) HUH ⁡ (f) - HUH ⁡ (p)) where S is selectivity in mol %, UH(p) is moles of the unsaturated hydrocarbon in the product, UH(f)is moles of the unsaturated hydrocarbon in the hydrocarbon stream, HUH(f) is the moles of highly unsaturated hydrocarbon in the hydrocarbon stream, and HUH(p) is the moles of the highly unsaturated hydrocarbon in the product.",
    "3. The process of claim 1, wherein the highly unsaturated hydrocarbon further comprises methylacetylene, propadiene, or both; and wherein the unsaturated hydrocarbon further comprises propylene.",
    "4. The process of claim 1, further comprising: cracking a feed stream to produce a cracked gas stream comprising the highly unsaturated hydrocarbon, carbon monoxide, and a saturated hydrocarbon.",
    "5. The process of claim 4, further comprising: fractionating the cracked gas stream to yield a C 3 − stream or C 2 − stream comprising the highly unsaturated hydrocarbon, carbon monoxide, and about 90 mol % or greater of the saturated hydrocarbon contained in the cracked gas stream, wherein at least a portion of the highly unsaturated hydrocarbon in the C 3 − stream or the C 2 − stream is hydrogenated in the presence of the hydrogenation catalyst.",
    "6. The process of claim 1, wherein the [CO] in the reaction zone is from about 0.0001 mol % to about 0.15 mol %.",
    "7. The process of claim 1, wherein the hydrogenating step comprises: contacting the hydrogenation catalyst with at least a portion of the highly unsaturated hydrocarbon in the presence of hydrogen.",
    "8. The process of claim 1, wherein the reaction zone comprises a first stage and a second stage, wherein at least one of the first stage and the second stage of the reaction zone contains the hydrogenation catalyst.",
    "9. The process of claim 8, wherein: i) the first stage of the reaction zone and the second stage of the reaction zone are contained in a common vessel; or ii) the first stage of the reaction zone is a first reactor, the second stage of the reaction zone is a second reactor, and the first reactor and the second reactor are connected in series.",
    "10. A process comprising: cracking a feed stream to produce a cracked gas stream comprising acetylene, ethylene, ethane, methane, hydrogen, carbon monoxide, and C 3 + components; fractionating the cracked gas stream into a C 2 − stream and a C 3 + stream, wherein the C 2 − stream comprises acetylene, ethylene, ethane, methane, hydrogen, and carbon monoxide, wherein the C 3 + stream comprises the C 3 + components; hydrogenating at least a portion of the acetylene of the C 2 − stream in the presence of a hydrogenation catalyst to yield a product comprising ethylene, wherein the hydrogenation catalyst has a selectivity for conversion of acetylene to ethylene of about 90 mol % or greater based on the moles of acetylene which are converted to the product, wherein the hydrogenating occurs in a reaction zone under conditions comprising a flow index (I F) in a range of about 0.09 to about 35, wherein the I F is defined as: I F = F × [CO] V, wherein F is the flow rate of the C 2 − stream into the reaction zone in units of kg/h, [CO] is the concentration of carbon monoxide in the C 2 − stream in units of mol %, and V is the volume of the portion of the reaction zone in units of ft 3; removing ethylene from the product; and polymerizing ethylene into one or more polymer products.",
    "11. The process of claim 10, wherein the selectivity is defined as: S = 100 × (UH ⁡ (p) - UH ⁡ (f) HUH ⁡ (f) - HUH ⁡ (p)) where S is the selectivity in mol %, UH(p) is moles of ethylene in the product, UH(f) is moles of ethylene in the hydrocarbon stream, HUH(f) is the moles of acetylene in the hydrocarbon stream, and HUH(p) is the moles of acetylene in the product.",
    "12. A process comprising: cracking a feed stream to produce a cracked gas stream comprising a highly unsaturated hydrocarbon, carbon monoxide, and a saturated hydrocarbon; fractionating the cracked gas stream to yield a C 3 − stream or a C 2 − stream comprising the highly unsaturated hydrocarbon, carbon monoxide, and about 90 mol % or greater of the saturated hydrocarbon contain in the cracked gas stream, providing the C 3 − stream or a C 2 31 stream to a reaction zone comprising a hydrogenation catalyst, wherein at least a portion of the highly unsaturated hydrocarbon in the C 3 − stream or the C 2 − is hydrogenated in the presence of the hydrogenation catalyst; and hydrogenating, in the reaction zone, the highly unsaturated hydrocarbon to yield a product comprising an unsaturated hydrocarbon, wherein the hydrogenation catalyst has a selectivity for conversion of the highly unsaturated hydrocarbon to the unsaturated hydrocarbon of about 90 mol % or greater based on moles of the highly unsaturated hydrocarbon which are converted to the product, wherein the hydrogenating step occurs under conditions comprising a flow index (I F;) in a range of about 0.09 to about 35, wherein the I F is defined as: I F = F × [CO] V, wherein F is the flow rate of the hydrocarbon stream into the reaction zone in units of kg/h, [CO] is the concentration of carbon monoxide in the hydrocarbon stream in units of mol %, and V is the volume of the portion of the reaction zone in units of ft 3.",
    "13. The process of claim 12, wherein the selectivity is defined as: S = 100 × (UH ⁡ (p) - UH ⁡ (f) HUH ⁡ (f) - HUH ⁡ (p)) where S is the selectivity in mol %, UH(p) is moles of the unsaturated hydrocarbon in the product, UH(f) is moles of the unsaturated hydrocarbon in the hydrocarbon stream, HUH(f) is the moles of highly unsaturated hydrocarbon in the hydrocarbon stream, and HUH(p) is the moles of the highly unsaturated hydrocarbon in the product."
  ],
  "description_excerpt": "Not applicable.\n\nThe present disclosure relates to the production of an unsaturated hydrocarbon, and more particularly to a hydrogenation of compounds using highly selective catalyst.\n\nUnsaturated hydrocarbons such as ethylene and propylene are often employed as feedstocks in preparing value added chemicals and polymers. Unsaturated hydrocarbons can be produced by pyrolysis or cracking of hydrocarbons including hydrocarbons derived from coal, oil, gas, synthetic crude, naphthas, natural gas liquids, raffinate, refinery gases, ethane, propane, butane, and the like. Unsaturated hydrocarbons products produced in these manners usually contain highly unsaturated hydrocarbons such as acetylenes and diolefins that adversely affect the production of subsequent chemicals and polymers. Thus, to form an unsaturated hydrocarbon product such as a polymer grade monoolefin, the amount of acetylenes and diolefins in the monoolefin stream is typically reduced. One technique commonly used to reduce the amount of acetylenes and diolefins in an unsaturated hydrocarbon stream primarily comprising monoolefins involves hydrogenating the acetylenes and diolefins to monoolefins. This process is selective in that hydrogenation of a monoolefin and a highly unsaturated hydrocarbon to the saturated hydrocarbon is minimized. For example, the hydrogenation of ethylene or acetylene to ethane is minimized.\n\nOne challenge to the selective hydrogenation process is the potential for a runaway reaction which is uncontrolled hydrogenation of ethylene to ethane. One methodology to minimize runaway reactions is to use a highly selective hydrogenation catalyst.",
  "cpc": [
    "C10G 45/32",
    "B01J 19/24",
    "B01J 19/245",
    "B01J 2219/00306",
    "B01J 2219/24",
    "B65G 1/045",
    "B65G 1/0492",
    "B65G 1/065",
    "B65G 1/10",
    "B65G 1/127",
    "B65G 1/137",
    "B65G 1/1371",
    "B65G 1/1373",
    "B65G 1/1378",
    "B65G 47/57",
    "C07C 2521/04",
    "C07C 4/04",
    "C07C 5/05",
    "C07C 5/09",
    "C10G 2400/20",
    "C10G 2400/24",
    "C10G 69/06",
    "C10G 70/02",
    "C10G 9/00",
    "Y10S 901/01"
  ],
  "ipc": [
    "B01J 19/24",
    "C07C 4/04",
    "C07C 5/03",
    "C07C 5/05",
    "C07C 5/09",
    "C10G 45/32",
    "C10G 69/06",
    "C10G 70/02",
    "C10G 9/00"
  ],
  "assignees": [
    "CHEVRON PHILLIPS CHEMICAL CO LP"
  ],
  "inventors": [
    "BERGMEISTER III JOSEPH",
    "CHEUNG TIN-TACK PETER",
    "HONG ZONGXUAN",
    "ODI TIMOTHY O",
    "NOLIDIN CHARLES D",
    "GONZALES THOMAS J",
    "NILL JENNIFER L",
    "DOCKTER DAVID W"
  ],
  "filing_date": "2015-11-16",
  "publication_date": "2017-09-12",
  "grant_date": "2017-09-12",
  "priority_date": "2015-11-16",
  "application_number": "US-201514942816-A",
  "family_id": "57392078",
  "citations": [
    "US2002004622A1",
    "US2004192983A1",
    "US2005256281A1",
    "US2007161833A1",
    "US2010228065A1",
    "US2012209042A1",
    "US2013172641A1",
    "US4404124A",
    "US4484015A",
    "US4517395A",
    "US5475173A",
    "US5489565A",
    "US5510550A",
    "US5585318A",
    "US5587348A",
    "US7038096B2",
    "US7141709B2",
    "US8633127B2"
  ]
}

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