CA2518260A1 - Selective hydrogenation of acetylenes and dienes in a hydrocarbon stream - Google Patents
Selective hydrogenation of acetylenes and dienes in a hydrocarbon stream Download PDFInfo
- Publication number
- CA2518260A1 CA2518260A1 CA002518260A CA2518260A CA2518260A1 CA 2518260 A1 CA2518260 A1 CA 2518260A1 CA 002518260 A CA002518260 A CA 002518260A CA 2518260 A CA2518260 A CA 2518260A CA 2518260 A1 CA2518260 A1 CA 2518260A1
- Authority
- CA
- Canada
- Prior art keywords
- reactor
- boiling point
- liquid
- acetylenes
- dienes
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000001993 dienes Chemical class 0.000 title claims abstract description 20
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 title claims abstract description 19
- 238000005984 hydrogenation reaction Methods 0.000 title claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 title description 7
- 229930195733 hydrocarbon Natural products 0.000 title description 7
- 150000002430 hydrocarbons Chemical class 0.000 title description 7
- 239000007788 liquid Substances 0.000 claims abstract description 26
- 238000009835 boiling Methods 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000001336 alkenes Chemical class 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000008096 xylene Substances 0.000 claims abstract description 5
- 150000003738 xylenes Chemical class 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- 238000004821 distillation Methods 0.000 abstract description 8
- 230000003134 recirculating effect Effects 0.000 abstract description 4
- 239000002245 particle Substances 0.000 abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 150000000475 acetylene derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 102200058451 rs80358203 Human genes 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/08—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of carbon-to-carbon triple bonds
- C07C5/09—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of carbon-to-carbon triple bonds to carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
- C07C5/05—Partial hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/163—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/163—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation
- C07C7/167—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation for removal of compounds containing a triple carbon-to-carbon bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/44—Palladium
Abstract
Acetylenes and dienes in a stream containing hydrogen, methane, C2-C6 olefins and paraffins, C2-C6 acetylenes and dienes, benzene, toluene, xylenes, and other C6+ components are hydrogenated in a downflow boiling point reactor wherein the heat of reaction is absorbed by the liquid in the reactor which produces a vapor. Besides the feed to the reactor there is a recirculating stream which is fed at a rate sufficient to ensure that the catalyst particles within the reactor are wetted. A third stream, which is taken from a downstream distillation column, is fed to provide the make up mass corresponding to the mass evaporated in the reactor. The composition of the this third stream controls the steady state composition of the liquid flowing through the reactor.
Description
SELECTIVE HYDROGENATION OF ACETYLENES
AND DIENES IN A HYDROCARBON STREAM
BACKGROUND OF THE INVENTION
' Field of the Invention The present invention relates to a process for selectively hydrogenating acetylenes and dienes in a hydrocarbon stream. More particularly the invention relates to the selective hydrogenation of acetylenes and dienes in a hydrocarbon stream containing hydrogen, olefins and smaller amounts of acetylenes and dienes using a downflow boiling point reactor.
Related Information The vapor product stream from the quench system of a hydrocarbon steam cracker typically consists mainly of hydrogen, methane, C~-C6 olefins and paraffins, C2-C6 acetylenes and dienes, benzene, toluene, xylenes, and other C6+
components. Separation and recovery of the products according to carbon number is generally accomplished in a sequential distillation sysfiem after the first separation of hydrogen from the methane in a high pressure cold box sysfiem. The design of the distillation system is complicated by the fact that the differences in relative volatility of the olefins, acetylenes, and dienes of the same carbon number are small maleing it difficult to produce the pure olefin products. One method of circumventing this problem is to first separate the carbon number fractions and then to selectively hydrotreat each fraction to convert the acetylene and/or diene to its corresponding olefin or paraffin. This so called "back end" approach requires a separate hydrotreating system for each carbon number fraction as well as the addition of a requisite amount of hydrogen to each system. An alternative method is to hydrotreat the feed stream before separation using the contained hydrogen as the source of hydrogen for the conversion. This so-called "front end" approach has the advantage , of removing a significant portion of the hydrogen from the feed stream to the cold box thereby reducing the size and refrigeration requirements of the cold box.
SUMMARY OF THE INVENTION
The present invention provides a "front end" hydrotreating system that allows for effective control of the temperature within a bed of catalyst which is hydrogenating acetyleries and dienes in a stream containing hydrogen, methane, C2-C6 olefins and paraffins, C2-C6 acetylenes and dienes, benzene, toluene, xylenes, and other C6+
components. The invention utilizes a downflow boiling point reactor wherein the heat of reaction is absorbed by the liquid in the reactor which produces a vapor.
Besides the feed to the reactor there is a recirculating stream which is fed at a rate sufficient to ensure that the catalyst particles within the reactor are wetted. A third stream, which is taken from a downstream distillation column, is fed to provide the make up mass corresponding to the mass evaporated in the reactor. The composition of the this third stream controls the steady state composition of the liquid flowing through the reactor. The composition of this stream may be controlled by selecting the point from the downstream distillation column from which the stream is drawn. The lower the draw point is in the column, the higher the boiling point of the components in the third stream. The steady state composition of the liquid flowing through the reactor along with the pressure determines the reactor temperature profile.
In a "boiling point reactor" a liquid phase is always maintained, even if the reaction components would be vaporized by the exothermic heat of reaction. In any reaction where the reaction stream is likely to be vaporized, an inert higher boiling component may be added to maintain a liquid phase.
BRIEF DESCRIPTION OF THE DRAWING
FIG. 9 is a flow diagram in schematic form of one embodiment of the invention.
FIG. 2 is graphical representation of the temperature profile in a typical reactor of the present invention.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT
Catalysts which are useful for the selective hydrogenation of acetylenes and dienes include palladium oxide supported on alumina. One such catalyst contains 0.34 wt.% palladium supported on 1/8 inch spheres designated G68C and supplied by Sud-Chemie (formerly United Catalyst Inc.). Another catalyst comprises 0.5 wt.%
palladium supported on 8-12 mesh spheres and designated E144SDU as supplied by Calcicat, Catalyst and Performance Chemicals Division, Mallinckrodt, Inc.
For best results the catalyst is supported in structured packing as disclosed in commonly owned U.S. Pat. No. 5,730,843. The catalyst may, however, be simply loaded into the reactor.
AND DIENES IN A HYDROCARBON STREAM
BACKGROUND OF THE INVENTION
' Field of the Invention The present invention relates to a process for selectively hydrogenating acetylenes and dienes in a hydrocarbon stream. More particularly the invention relates to the selective hydrogenation of acetylenes and dienes in a hydrocarbon stream containing hydrogen, olefins and smaller amounts of acetylenes and dienes using a downflow boiling point reactor.
Related Information The vapor product stream from the quench system of a hydrocarbon steam cracker typically consists mainly of hydrogen, methane, C~-C6 olefins and paraffins, C2-C6 acetylenes and dienes, benzene, toluene, xylenes, and other C6+
components. Separation and recovery of the products according to carbon number is generally accomplished in a sequential distillation sysfiem after the first separation of hydrogen from the methane in a high pressure cold box sysfiem. The design of the distillation system is complicated by the fact that the differences in relative volatility of the olefins, acetylenes, and dienes of the same carbon number are small maleing it difficult to produce the pure olefin products. One method of circumventing this problem is to first separate the carbon number fractions and then to selectively hydrotreat each fraction to convert the acetylene and/or diene to its corresponding olefin or paraffin. This so called "back end" approach requires a separate hydrotreating system for each carbon number fraction as well as the addition of a requisite amount of hydrogen to each system. An alternative method is to hydrotreat the feed stream before separation using the contained hydrogen as the source of hydrogen for the conversion. This so-called "front end" approach has the advantage , of removing a significant portion of the hydrogen from the feed stream to the cold box thereby reducing the size and refrigeration requirements of the cold box.
SUMMARY OF THE INVENTION
The present invention provides a "front end" hydrotreating system that allows for effective control of the temperature within a bed of catalyst which is hydrogenating acetyleries and dienes in a stream containing hydrogen, methane, C2-C6 olefins and paraffins, C2-C6 acetylenes and dienes, benzene, toluene, xylenes, and other C6+
components. The invention utilizes a downflow boiling point reactor wherein the heat of reaction is absorbed by the liquid in the reactor which produces a vapor.
Besides the feed to the reactor there is a recirculating stream which is fed at a rate sufficient to ensure that the catalyst particles within the reactor are wetted. A third stream, which is taken from a downstream distillation column, is fed to provide the make up mass corresponding to the mass evaporated in the reactor. The composition of the this third stream controls the steady state composition of the liquid flowing through the reactor. The composition of this stream may be controlled by selecting the point from the downstream distillation column from which the stream is drawn. The lower the draw point is in the column, the higher the boiling point of the components in the third stream. The steady state composition of the liquid flowing through the reactor along with the pressure determines the reactor temperature profile.
In a "boiling point reactor" a liquid phase is always maintained, even if the reaction components would be vaporized by the exothermic heat of reaction. In any reaction where the reaction stream is likely to be vaporized, an inert higher boiling component may be added to maintain a liquid phase.
BRIEF DESCRIPTION OF THE DRAWING
FIG. 9 is a flow diagram in schematic form of one embodiment of the invention.
FIG. 2 is graphical representation of the temperature profile in a typical reactor of the present invention.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT
Catalysts which are useful for the selective hydrogenation of acetylenes and dienes include palladium oxide supported on alumina. One such catalyst contains 0.34 wt.% palladium supported on 1/8 inch spheres designated G68C and supplied by Sud-Chemie (formerly United Catalyst Inc.). Another catalyst comprises 0.5 wt.%
palladium supported on 8-12 mesh spheres and designated E144SDU as supplied by Calcicat, Catalyst and Performance Chemicals Division, Mallinckrodt, Inc.
For best results the catalyst is supported in structured packing as disclosed in commonly owned U.S. Pat. No. 5,730,843. The catalyst may, however, be simply loaded into the reactor.
Referring now to FIG. 1 selective hydrogenation of acetylenes and diolefins in a hydrocarbon stream containing significantly larger amounts (molar basis) of hydrogen and olefins than the acetylenes and diolefins is carried out in a downflow boiling point reactor. The downflow boiling point reactor, shown as column 10 is a vertically disposed reactor containing the particulate catalyst supported in a structured packing at 12. The gaseous feed stream is fed via flow line 101 to the top of the column 10. Also fed to the top of the reactor is liquid in flow line 104 which is a mixture of circulating stream in flow line 102 and stream in flow line 103 derived from distillation column 40 as more particularly described below. Gas and liquid streams flow concurrently downward through the column with the flow regime being gas continuous. The concurrent flow of gas and liquid eliminates the possibility of a runaway reaction.
The reactor 10 is operated adiabatically so that the heat of reaction is accounted for by preferentially evaporating the lighter liquid phase components.
Effiluent from the reactor in flow line 105 is fed to vapor/liquid separator 20 where the vapor and liquid are separated. The heat content of the vapor in flow line 106 includes the heat of reaction generated in the reactor 10 while its mass rate is equal to the combined flows of the streams in flow lines 101 and 103 less slip stream 107 described below. Liquid in flow line 102 is fed back to the top of the reactor 10. The flow rate of the stream in flow line 102 is a variable and is maintained at least sufficient to ensure that the catalyst particles are fully wetted at all positions in the reactor 10. The stream in flow line 103 provides make up mass corresponding to the mass evaporated in the reactor that leaves the reactor system as part of the stream in flow line 106. The composition of the stream in flow line 103 controls fihe steady state composition of liquid flowing through the reactor 10. This is an important operating parameter that in combination with the reactor pressure determines the reactor temperature profile. A slip stream is taken by flow line 107 to control the liquid inventory in the vapor/liquid separator vessel 20.
Column 40 is a C5/C6 splitter. Feed to the column is the vapor from the separator 20 in flow line 106. It is heated by indirect heat exchange in exchanger 30 with the recirculating stream in flow line 103. The column 40 is designed to recover a vapor distillate fraction via flow line 108 which is essentially free of C6+
components and a bottoms liquid product in flow line 109 which is essentially free of C5 and lighter components. The overheads are taken via flow line 130 and passed through partial condenser 50 where the heavier components are condensed. The overheads are collected in receiver separator 60 where liquid hydrocarbon is withdrawn via flow line 120 and returned to the column 40 as reflux. Water is taken out via flow line 110. As noted distillate product is removed via flow line 108.
The draw off position or tray of the recirculating stream in flow line 103 is an operating variable. Moving the take off point further down the column increases the higher boiling components in the stream. Minimum operating pressure forthe reactor 10 at a fixed temperature profile is achieved when the draw off is from the bottom stage of the column 40.
EXAMPLE
Feed to the system depicted in FIG. 1 is the vapor product from the quench tower of an olefins producing steam cracker after compression and acid gas (C~~ and H2S) removal. The reactor is loaded with approximately 14,000 ft3 structured packing loaded with hydrogenation catalyst. Eed dimensions are approximately 15 ft diameter by ~0 ft long. ~perating conditions for the reactor are: reactor top/bottom pressure 250/240 psia; liquid recycle rate (stream in flow line 102) 4,000,000 Ibs./hr.; slip stream in flow line 10'l 2243 Ibs./hr. The distillation column 40 is a column configured with a 16.4 ft diameter 20 stage (theoretical) top section and 10.5 ffi 20 stage (theoretical) bottom section. ~esign conditions for the distillation column 40 are:
reflux ratio 0.18; reflux temperature 136°F, condenser pressure is 238 Asia; column pressure drop is 2 psi; bottom stage side draw; decanter temperature 84°F. Heat and material balance results are given in TALE I. Temperature profile across the reactor is given in FIG. 2.
The reactor 10 is operated adiabatically so that the heat of reaction is accounted for by preferentially evaporating the lighter liquid phase components.
Effiluent from the reactor in flow line 105 is fed to vapor/liquid separator 20 where the vapor and liquid are separated. The heat content of the vapor in flow line 106 includes the heat of reaction generated in the reactor 10 while its mass rate is equal to the combined flows of the streams in flow lines 101 and 103 less slip stream 107 described below. Liquid in flow line 102 is fed back to the top of the reactor 10. The flow rate of the stream in flow line 102 is a variable and is maintained at least sufficient to ensure that the catalyst particles are fully wetted at all positions in the reactor 10. The stream in flow line 103 provides make up mass corresponding to the mass evaporated in the reactor that leaves the reactor system as part of the stream in flow line 106. The composition of the stream in flow line 103 controls fihe steady state composition of liquid flowing through the reactor 10. This is an important operating parameter that in combination with the reactor pressure determines the reactor temperature profile. A slip stream is taken by flow line 107 to control the liquid inventory in the vapor/liquid separator vessel 20.
Column 40 is a C5/C6 splitter. Feed to the column is the vapor from the separator 20 in flow line 106. It is heated by indirect heat exchange in exchanger 30 with the recirculating stream in flow line 103. The column 40 is designed to recover a vapor distillate fraction via flow line 108 which is essentially free of C6+
components and a bottoms liquid product in flow line 109 which is essentially free of C5 and lighter components. The overheads are taken via flow line 130 and passed through partial condenser 50 where the heavier components are condensed. The overheads are collected in receiver separator 60 where liquid hydrocarbon is withdrawn via flow line 120 and returned to the column 40 as reflux. Water is taken out via flow line 110. As noted distillate product is removed via flow line 108.
The draw off position or tray of the recirculating stream in flow line 103 is an operating variable. Moving the take off point further down the column increases the higher boiling components in the stream. Minimum operating pressure forthe reactor 10 at a fixed temperature profile is achieved when the draw off is from the bottom stage of the column 40.
EXAMPLE
Feed to the system depicted in FIG. 1 is the vapor product from the quench tower of an olefins producing steam cracker after compression and acid gas (C~~ and H2S) removal. The reactor is loaded with approximately 14,000 ft3 structured packing loaded with hydrogenation catalyst. Eed dimensions are approximately 15 ft diameter by ~0 ft long. ~perating conditions for the reactor are: reactor top/bottom pressure 250/240 psia; liquid recycle rate (stream in flow line 102) 4,000,000 Ibs./hr.; slip stream in flow line 10'l 2243 Ibs./hr. The distillation column 40 is a column configured with a 16.4 ft diameter 20 stage (theoretical) top section and 10.5 ffi 20 stage (theoretical) bottom section. ~esign conditions for the distillation column 40 are:
reflux ratio 0.18; reflux temperature 136°F, condenser pressure is 238 Asia; column pressure drop is 2 psi; bottom stage side draw; decanter temperature 84°F. Heat and material balance results are given in TALE I. Temperature profile across the reactor is given in FIG. 2.
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Claims (9)
1. A process for the hydrogenation of acetylenes and dienes in a stream containing hydrogen, methane, C2-C6 olefins and paraffins, C2-C6 acetylenes and dienes, benzene, toluene, xylenes, and other C6+ components comprising passing said stream over a hydrogenation catalyst contained in a downflow boiling point reactor wherein the reactor is operated at the boiling point of the mixture in the reactor and the heat of reaction is absorbed by the boiling liquid and where a portion of the acetylenes and dienes are converted to their corresponding olefins and paraffins of the same carbon number.
2. The process according to claim 1 wherein the liquid and vapor in the effluent from said downflow boiling point reactor is separated and a portion of the liquid is recycled back to the top of said downflow boiling point reactor.
3. The process according to claim 2 wherein the amount of the liquid being recycled is maintained sufficient to ensure that the catalyst is fully wetted at all positions within said downflow boiling point reactor.
4. The process according to claim 2 wherein the vapor in said effluent is fed to a C5/C6 splitter where C5 and lighter material are taken as overheads and C6 and heavier material is taken as bottoms.
5. The process according to claim 4 wherein a side draw is taken from said C5/C6 splitter and fed to the top of said downflow boiling point reactor.
6. The process according to claim 5 wherein the steady state composition of the liquid flowing in said downflow boiling point reactor is controlled by the location of the draw point of said side draw along the height of said C5/C6 splitter.
7. The process according to claim 6 wherein said side draw is taken from the bottom stage of said C5/C6 splitter.
8. A process for the hydrogenation of acetylenes and dienes in a stream containing hydrogen, methane, C2-C6 olefins and paraffins, C2-C6 acetylenes and dienes, benzene, toluene, xylenes, and other C6+ components comprising the steps of:
(a) passing said stream over a hydrogenation catalyst contained in a downflow boiling point reactor wherein the reactor is operated at the boiling point of the mixture in the reactor and the heat of reaction is absorbed by the boiling liquid and where a portion of the acetylenes and dienes are converted to their corresponding olefins and paraffins of the same carbon number;
(b) separating the liquid and vapor contained in the effluent from said downflow boiling point reactor;
(c) returning a portion of the separated liquid to the top of said downflow boiling point reactor;
(d) maintaining the amount of the liquid being returned to ensure that the catalyst is fully wetted at all positions within said downflow boiling point reactor;
(e) feeding the vapor in said effluent to a C5/C6 splitter where C5 and lighter material are taken as overheads and C6 and heavier material are taken as bottoms;
(f) taking a side draw from said C5/C6 splitter and feeding said side draw to the top of said downflow boiling point reactor; and (g) controlling the steady state composition of the liquid flowing in said downflow boiling point reactor by selecting the position of said side draw along the height of said C5/C6 splitter.
(a) passing said stream over a hydrogenation catalyst contained in a downflow boiling point reactor wherein the reactor is operated at the boiling point of the mixture in the reactor and the heat of reaction is absorbed by the boiling liquid and where a portion of the acetylenes and dienes are converted to their corresponding olefins and paraffins of the same carbon number;
(b) separating the liquid and vapor contained in the effluent from said downflow boiling point reactor;
(c) returning a portion of the separated liquid to the top of said downflow boiling point reactor;
(d) maintaining the amount of the liquid being returned to ensure that the catalyst is fully wetted at all positions within said downflow boiling point reactor;
(e) feeding the vapor in said effluent to a C5/C6 splitter where C5 and lighter material are taken as overheads and C6 and heavier material are taken as bottoms;
(f) taking a side draw from said C5/C6 splitter and feeding said side draw to the top of said downflow boiling point reactor; and (g) controlling the steady state composition of the liquid flowing in said downflow boiling point reactor by selecting the position of said side draw along the height of said C5/C6 splitter.
9. The process according to claim 8 wherein said side draw is taken from the bottom stage of said C5/C6 splitter.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/385,677 US6867338B2 (en) | 2002-03-15 | 2003-03-12 | Selective hydrogenation of acetylenes and dienes in a hydrocarbon stream |
| US10/385,677 | 2003-03-12 | ||
| PCT/US2004/006535 WO2004081149A2 (en) | 2003-03-12 | 2004-03-04 | Selective hydrogenation of acetylenes and dienes in a hydrocarbon stream |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2518260A1 true CA2518260A1 (en) | 2004-09-23 |
Family
ID=32987306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002518260A Abandoned CA2518260A1 (en) | 2003-03-12 | 2004-03-04 | Selective hydrogenation of acetylenes and dienes in a hydrocarbon stream |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US6867338B2 (en) |
| EP (1) | EP1618082A2 (en) |
| JP (1) | JP2006522120A (en) |
| KR (1) | KR20050106112A (en) |
| CN (1) | CN100371305C (en) |
| AR (1) | AR043554A1 (en) |
| AU (1) | AU2004219723A1 (en) |
| BR (1) | BRPI0400329A (en) |
| CA (1) | CA2518260A1 (en) |
| EG (1) | EG23539A (en) |
| MX (1) | MXPA05009270A (en) |
| PL (1) | PL378808A1 (en) |
| RU (1) | RU2325429C2 (en) |
| WO (1) | WO2004081149A2 (en) |
Families Citing this family (12)
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|---|---|---|---|---|
| US20040030207A1 (en) * | 2002-08-08 | 2004-02-12 | Catalytic Distillation Technologies | Selective hydrogenation of acetylenes |
| US7022645B2 (en) * | 2003-08-04 | 2006-04-04 | Catalytic Distillation Technologies | Ni hydrogenation catalysts, manufacture and use |
| US20060173224A1 (en) * | 2005-02-01 | 2006-08-03 | Catalytic Distillation Technologies | Process and catalyst for selective hydrogenation of dienes and acetylenes |
| JP4845172B2 (en) * | 2005-03-30 | 2011-12-28 | 月島機械株式会社 | Method and apparatus for adiabatic cooling crystallization of organic compounds |
| US7408090B2 (en) * | 2005-04-07 | 2008-08-05 | Catalytic Distillation Technologies | Method of operating downflow boiling point reactors in the selective hydrogenation of acetylenes and dienes |
| US8471082B2 (en) * | 2008-03-14 | 2013-06-25 | Catalytic Distillation Technologies | Process for converting methane to ethylene |
| EP2223987A1 (en) * | 2009-02-17 | 2010-09-01 | ISP Marl GmbH | Purification of an aromatic fraction containing acetylenes by selective hydrogenation of the acetylenes |
| US20120209042A1 (en) | 2011-02-10 | 2012-08-16 | Saudi Basic Industries Corporation | Liquid Phase Hydrogenation of Alkynes |
| US9695096B2 (en) * | 2012-07-12 | 2017-07-04 | Lummus Technology Inc. | More energy efficient C5 hydrogenation process |
| JP6298438B2 (en) * | 2014-11-28 | 2018-03-20 | 旭化成株式会社 | Process for producing hydrocarbons |
| FR3045651B1 (en) * | 2015-12-22 | 2018-01-19 | IFP Energies Nouvelles | METHOD FOR SELECTIVE HYDROGENATION OF OLEFINIC LOADS WITH A MAIN REACTOR THRESHOLD AND A REDUCED SIZE REACTION REACTOR |
| RU2673550C1 (en) * | 2018-05-15 | 2018-11-28 | Публичное Акционерное Общество "Нижнекамскнефтехим" | Method for coproduction of cyclohexane and hexane solvent |
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| US2918425A (en) * | 1958-03-27 | 1959-12-22 | Universal Oil Prod Co | Conversion process and apparatus therefor |
| US3560167A (en) * | 1968-12-18 | 1971-02-02 | Air Prod & Chem | Upflow catalytic reactor for fluid hydrocarbons |
| US3702237A (en) * | 1970-07-02 | 1972-11-07 | Universal Oil Prod Co | Hydrocarbon conversion apparatus |
| US4126539A (en) * | 1977-12-05 | 1978-11-21 | Mobil Oil Corporation | Method and arrangement of apparatus for hydrogenating hydrocarbons |
| US4194964A (en) * | 1978-07-10 | 1980-03-25 | Mobil Oil Corporation | Catalytic conversion of hydrocarbons in reactor fractionator |
| US4171260A (en) * | 1978-08-28 | 1979-10-16 | Mobil Oil Corporation | Process for reducing thiophenic sulfur in heavy oil |
| US4283271A (en) * | 1980-06-12 | 1981-08-11 | Mobil Oil Corporation | Manufacture of hydrocracked low pour lubricating oils |
| US5190730A (en) * | 1982-11-17 | 1993-03-02 | Chemical Research & Licensing Company | Reactor for exothermic reactions |
| US4484983A (en) * | 1983-05-23 | 1984-11-27 | Shell Oil Company | Distillation and vapor treatment process |
| US4990242A (en) * | 1989-06-14 | 1991-02-05 | Exxon Research And Engineering Company | Enhanced sulfur removal from fuels |
| US5011593A (en) * | 1989-11-20 | 1991-04-30 | Mobil Oil Corporation | Catalytic hydrodesulfurization |
| US5409599A (en) * | 1992-11-09 | 1995-04-25 | Mobil Oil Corporation | Production of low sulfur distillate fuel |
| US5714640A (en) * | 1994-01-21 | 1998-02-03 | Mobil Oil Corporation | Vapor pocket reactor |
| US5510568A (en) * | 1994-06-17 | 1996-04-23 | Chemical Research & Licensing Company | Process for the removal of mercaptans and hydrogen sulfide from hydrocarbon streams |
| US5554275A (en) * | 1994-11-28 | 1996-09-10 | Mobil Oil Corporation | Catalytic hydrodesulfurization and stripping of hydrocarbon liquid |
| US5779883A (en) * | 1995-07-10 | 1998-07-14 | Catalytic Distillation Technologies | Hydrodesulfurization process utilizing a distillation column realtor |
| US5961815A (en) * | 1995-08-28 | 1999-10-05 | Catalytic Distillation Technologies | Hydroconversion process |
| US5597476A (en) * | 1995-08-28 | 1997-01-28 | Chemical Research & Licensing Company | Gasoline desulfurization process |
| CA2244374C (en) | 1996-02-02 | 2005-04-12 | Exxon Research And Engineering Company | Selective hydrodesulfurization catalyst and process |
| US5925799A (en) * | 1996-03-12 | 1999-07-20 | Abb Lummus Global Inc. | Catalytic distillation and hydrogenation of heavy unsaturates in an olefins plant |
| US5807477A (en) * | 1996-09-23 | 1998-09-15 | Catalytic Distillation Technologies | Process for the treatment of light naphtha hydrocarbon streams |
| US5837130A (en) * | 1996-10-22 | 1998-11-17 | Catalytic Distillation Technologies | Catalytic distillation refining |
| US5925685A (en) * | 1996-11-18 | 1999-07-20 | Catalytic Distillation Technologies | Method for carrying out heterogeneous catalysis |
| US5863419A (en) * | 1997-01-14 | 1999-01-26 | Amoco Corporation | Sulfur removal by catalytic distillation |
| US5897768A (en) | 1997-02-28 | 1999-04-27 | Exxon Research And Engineering Co. | Desulfurization process for removal of refractory organosulfur heterocycles from petroleum streams |
| US6083378A (en) * | 1998-09-10 | 2000-07-04 | Catalytic Distillation Technologies | Process for the simultaneous treatment and fractionation of light naphtha hydrocarbon streams |
| US6413413B1 (en) * | 1998-12-31 | 2002-07-02 | Catalytic Distillation Technologies | Hydrogenation process |
| FR2810991B1 (en) * | 2000-06-28 | 2004-07-09 | Inst Francais Du Petrole | PROCESS FOR HYDROGENATING CUTS CONTAINING HYDROCARBONS AND IN PARTICULAR UNSATURATED MOLECULES CONTAINING AT LEAST TWO DOUBLE LINKS OR AT LEAST ONE TRIPLE LINK |
| US6416658B1 (en) * | 2000-10-19 | 2002-07-09 | Catalytic Distillation Technologies | Process for simultaneous hydrotreating and splitting of naphtha streams |
-
2003
- 2003-03-12 US US10/385,677 patent/US6867338B2/en not_active Expired - Lifetime
-
2004
- 2004-03-04 EP EP04717376A patent/EP1618082A2/en not_active Withdrawn
- 2004-03-04 KR KR1020057016922A patent/KR20050106112A/en not_active Application Discontinuation
- 2004-03-04 CA CA002518260A patent/CA2518260A1/en not_active Abandoned
- 2004-03-04 PL PL378808A patent/PL378808A1/en not_active Application Discontinuation
- 2004-03-04 CN CNB2004800064972A patent/CN100371305C/en not_active Expired - Fee Related
- 2004-03-04 WO PCT/US2004/006535 patent/WO2004081149A2/en active Application Filing
- 2004-03-04 RU RU2005131579/04A patent/RU2325429C2/en not_active IP Right Cessation
- 2004-03-04 MX MXPA05009270A patent/MXPA05009270A/en unknown
- 2004-03-04 AU AU2004219723A patent/AU2004219723A1/en not_active Abandoned
- 2004-03-04 JP JP2006509063A patent/JP2006522120A/en not_active Withdrawn
- 2004-03-09 EG EG2004030104A patent/EG23539A/en active
- 2004-03-10 BR BR0400329-2A patent/BRPI0400329A/en not_active IP Right Cessation
- 2004-03-11 AR ARP040100788A patent/AR043554A1/en unknown
- 2004-11-08 US US10/983,433 patent/US7368617B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| RU2325429C2 (en) | 2008-05-27 |
| KR20050106112A (en) | 2005-11-08 |
| PL378808A1 (en) | 2006-05-15 |
| RU2005131579A (en) | 2006-02-10 |
| AR043554A1 (en) | 2005-08-03 |
| EP1618082A2 (en) | 2006-01-25 |
| CN100371305C (en) | 2008-02-27 |
| US6867338B2 (en) | 2005-03-15 |
| MXPA05009270A (en) | 2005-10-19 |
| JP2006522120A (en) | 2006-09-28 |
| CN1759083A (en) | 2006-04-12 |
| EG23539A (en) | 2006-04-26 |
| US20050090701A1 (en) | 2005-04-28 |
| AU2004219723A1 (en) | 2004-09-23 |
| US7368617B2 (en) | 2008-05-06 |
| WO2004081149A2 (en) | 2004-09-23 |
| US20030233017A1 (en) | 2003-12-18 |
| BRPI0400329A (en) | 2005-01-04 |
| WO2004081149A3 (en) | 2005-01-13 |
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