US3914332A - Oxidative dehydrogenation of butane - Google Patents

Oxidative dehydrogenation of butane Download PDF

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Publication number
US3914332A
US3914332A US418499A US41849973A US3914332A US 3914332 A US3914332 A US 3914332A US 418499 A US418499 A US 418499A US 41849973 A US41849973 A US 41849973A US 3914332 A US3914332 A US 3914332A
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butane
catalyst
oxygen
process according
percent
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US418499A
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Alan F Dickason
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Sun Ventures Inc
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Sun Ventures Inc
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    • 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
    • C07C5/42—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor
    • C07C5/48—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with a hydrogen acceptor with oxygen as an acceptor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/20—Vanadium, niobium or tantalum
    • B01J23/22—Vanadium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
    • B01J27/053—Sulfates
    • B01J27/055—Sulfates with alkali metals, copper, gold or silver

Definitions

  • Catalyst No. 902 obtainable from W. P. Grace & Co. It will be understood, of
  • butane may effectively be oxidatively dehydrogenated to butenes and butadiene at high space velocities when there is employed a catalyst comprising a mixture of an alkali metal compound, a vanadium oxide, and sulfur dioxide, supported on an SiO carrier.
  • this alkali metal /V.S catalyst permits the use of gaseous hourly space velocities in the range of about l000-20,000hr.- i.e. velocities which are at least 5-10 times those reported in the prior art.
  • the feed stream comprise substantially pure n-butane, but this is not essential.
  • the feed stock may contain a mixture of C to C hydrocarbons rich in n-butane admixed with other C., hydrocarbons as butenes, isobutenes, isobutane, as well as pentane and like compounds derived from straight run fractions, from thermal or catalytic dehydrogenation, and/or from cracking of C and higher hydrocarbons.
  • These other materi- 'als when present, are substantially inert to the conditions of this reaction, and thus act as inert diluents.
  • the butane should in any event, be present in the feed stream in amounts of from about 1 to 50 wt. percent, based on the total weight of the hydrocarbons, oxygen, and inert materials, if any, in said stream.
  • Oxygen either substantially pure or in the form of air, should preferably be present in stoichrometric amounts relative to the amount of butane in the feed stream, i.e. in about a 1:1 mol ratio, although ratios of 0.1:1 to :1 may be employed if desired. However, if the oxygen concentration is increased much beyond this latter range, competing oxidations start to take place with a resultant decrease in yield of desired product and an increase in the formation of C0
  • the oxygen is preferably introduced into the reactor by admixing it with the feed stream before it enters the reactor.
  • the catalyst which has been found to be uniquely effective for this process, as aforementioned, is a vanadium/alkali metal/sulfur catalyst on an SiO support where the alkali metal is preferably potassium.
  • Typical nents may be varied somewhat within the skill of the art while still providing the desired dehydrogenation effect. That is to say, the percentage range of the vanadium, potassium and sulfur components of the abovedescribed catalyst may be determined routinely by'simply noting the effect of the catalyst on the space velocity and selectivity to desired end products. Space velocities in the range of about 1000 to 20,000 hrsf, based on total gaseous feed, which provide selectivities of 50 to percent are considered within the scope of this invention.
  • the catalyst is generally provided in the form of pellets, so that desirably it is used in the reactor in the form of a fixed bed over which the gaseous feed stream is passed.
  • the catalyst may be provided in the form of a fluidized bed, or other conventional arrangements known in the art which permit rapid contact of a gas and/or liquid with a particulate solid catalyst.
  • the reaction is conveniently carried out at temperatures of from about 450to 650C, and preferably from about 500to 600C.
  • the gas hourly space velocity (GHSV), as described above, should be in the range of from about 1000 to 20,000 hr., and preferably above 10,000 hr.”.
  • the pressure in the reactor may be any convenient, practical pressure ranging from 1 to 100 atmospheres absolute.
  • the mol ratio of butane to oxygen, as aforestated, should desirably be 1:1, although somewhat higher amounts of oxygen may be used if desired.
  • a process for the oxidative dehydrogenation of butane to form a mixture of butenes and butadiene which comprises contacting said butane with oxygen in the presence of an oxidative dehydrogenation catalyst having a composition of about 9 wt. percent V about 29 wt. percent K 80 about 12 wt. percent S0 and about 50 wt. percent SiO wherein the reaction is carried out at temperatures of from about 450to 650C and ataGl-ISV of from about 1000 to 20,000 hr, and wherein the ratio of oxygen to butane is in the range of from about 1:1 to :1.
  • the catalyst comprises V 0 K SO and So supported on SiO wherein said catalyst has a surface area of 40 m /g.
  • reaction is carried out at a temperature of from about 500 the hydrocarbons, oxygen, and inerts in said stream.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Butane may be oxidatively dehydrogenated to a mixture of 1-and 2-butenes and butadiene at high space velocities using a catalyst comprising V2O5, K2SO4, SO3 and SiO2.

Description

United States Patent 191 Dickason [451 Oct. 21, 1975 OXIDATIVE DEHYDROGENATION OF BUTANE [75] Inventor: Alan F. Dickason, Chester, Del.
[73] Assignee: Sun Ventures, Inc., St. Davids, Pa.
[22] Filed: Nov. 23, 1973 [21] Appl. N0.: 418,499
[52] US. Cl. 260/680 E; 260/683.3
3,308,196 Bajars 260/680 D 3,308,200 3/1967 Bajars 260/680 D 3,403,192 9/1968 Vadekar et a1. 260/683.3 3,770,812 11/1973 Blood et al. 260/683.3
FOREIGN PATENTS OR APPLICATIONS 998,784 7/1965 United Kingdom 260/680 E Primary ExaminerPaul M. Coughlan, Jr. Attorney, Agent, or FirmGeorge L. Church; Donald R. Johnson; Stanford M. Back 5 7 ABSTRACT Butane may be oxidatively dehydrogenated to a mixture of l-and 2-butenes and butadiene at high space velocities using va catalyst comprising V 0 K SO,,, S0 and-SiO 8 Claims, N0 Drawings This invention relates to a process for the oxidative dehydrogenationof butane. More particularly, it relates to an improved method for the vapor phase oxidaamongst these is a catalyst having the composition, by
weight of 9% V 29% K 80 12% S0 and 50% SiO wherein the catalyst has a surface area of about 40 m /g. One such catalyst is Catalyst No. 902, obtainable from W. P. Grace & Co. It will be understood, of
- course, that the weight percent of the catalyst compotive dehydrogenation of butane to form, a mixture of l- I and 2-butenes and butadiene, employing a catalyst system which permits the use of space velocities substantially higher than those previously demonstrated by prior art.
Four references exemplifying known prior art oxidative dehydrogenation methods for carrying out this process by the use of various catalysts are as follows: French Pat. No. 1,326,396 (sodium or lithium phosphomolybdates); US. Pat. No. 3,119,11 l (lithium phosphomolybdate); British Pat. No. 943,941 (calcium nickel phosphate); and U.S. Pat. No. 3,320,331 (A1 PO -supported molybdenum and vanadium). Each of these methods, while useful in the dehydrogenation of butane, is characterized by relatively low space velocities and selectivities.
SUMMARY OF THE INVENTION It has now been found, in accordance with the present invention, that butane may effectively be oxidatively dehydrogenated to butenes and butadiene at high space velocities when there is employed a catalyst comprising a mixture of an alkali metal compound, a vanadium oxide, and sulfur dioxide, supported on an SiO carrier. When thus employed, this alkali metal /V.S catalyst permits the use of gaseous hourly space velocities in the range of about l000-20,000hr.- i.e. velocities which are at least 5-10 times those reported in the prior art.
DESCRIPTION OF THE INVENTION In carrying out this process, it is desirable that the feed stream comprise substantially pure n-butane, but this is not essential. Thus, the feed stock may contain a mixture of C to C hydrocarbons rich in n-butane admixed with other C., hydrocarbons as butenes, isobutenes, isobutane, as well as pentane and like compounds derived from straight run fractions, from thermal or catalytic dehydrogenation, and/or from cracking of C and higher hydrocarbons. These other materi- 'als, when present, are substantially inert to the conditions of this reaction, and thus act as inert diluents. The butane should in any event, be present in the feed stream in amounts of from about 1 to 50 wt. percent, based on the total weight of the hydrocarbons, oxygen, and inert materials, if any, in said stream.
Oxygen, either substantially pure or in the form of air, should preferably be present in stoichrometric amounts relative to the amount of butane in the feed stream, i.e. in about a 1:1 mol ratio, although ratios of 0.1:1 to :1 may be employed if desired. However, if the oxygen concentration is increased much beyond this latter range, competing oxidations start to take place with a resultant decrease in yield of desired product and an increase in the formation of C0 The oxygen is preferably introduced into the reactor by admixing it with the feed stream before it enters the reactor.
The catalyst which has been found to be uniquely effective for this process, as aforementioned, is a vanadium/alkali metal/sulfur catalyst on an SiO support where the alkali metal is preferably potassium. Typical nents may be varied somewhat within the skill of the art while still providing the desired dehydrogenation effect. That is to say, the percentage range of the vanadium, potassium and sulfur components of the abovedescribed catalyst may be determined routinely by'simply noting the effect of the catalyst on the space velocity and selectivity to desired end products. Space velocities in the range of about 1000 to 20,000 hrsf, based on total gaseous feed, which provide selectivities of 50 to percent are considered within the scope of this invention.
The catalyst is generally provided in the form of pellets, so that desirably it is used in the reactor in the form of a fixed bed over which the gaseous feed stream is passed. Alternatively, of course, the catalyst may be provided in the form of a fluidized bed, or other conventional arrangements known in the art which permit rapid contact of a gas and/or liquid with a particulate solid catalyst.
The reaction is conveniently carried out at temperatures of from about 450to 650C, and preferably from about 500to 600C. The gas hourly space velocity (GHSV), as described above, should be in the range of from about 1000 to 20,000 hr., and preferably above 10,000 hr.". The pressure in the reactor may be any convenient, practical pressure ranging from 1 to 100 atmospheres absolute. The mol ratio of butane to oxygen, as aforestated, should desirably be 1:1, although somewhat higher amounts of oxygen may be used if desired.
The invention will now be illustrated by the following examples.
EXAMPLE 1 A series of runs was carried out. In the first run 2.0 mls (2.0g) of catalyst was placed in a 6 Xl/4 inches stainless steel reactor and a gaseous mixture of nbutane (1%) and air (99%) was passed over the catalyst bed at 630C and at a GHSV=8100 hr.'. The conversion was 17% while the selectivity to butenes and butadiene was 82% The above procedure was then repeated, varying the concentration and reaction conditions. As will be seen from the above run and those in the following table, the GHSV for the vanadium-potassium-sulfur catalyst system of the invention is at least 5-10 times greater than for known catalyst systems. The practical significance of this substantial increase is an increase in the spacetime-yield or the ability to operate a smaller reactor, depending upon the desires of the operator.
The invention claimed is: I
1 A process for the oxidative dehydrogenation of butane to form a mixture of butenes and butadiene which comprises contacting said butane with oxygen in the presence of an oxidative dehydrogenation catalyst having a composition of about 9 wt. percent V about 29 wt. percent K 80 about 12 wt. percent S0 and about 50 wt. percent SiO wherein the reaction is carried out at temperatures of from about 450to 650C and ataGl-ISV of from about 1000 to 20,000 hr, and wherein the ratio of oxygen to butane is in the range of from about 1:1 to :1. y
2. The process according to claim 1 wherein the catalyst comprises V 0 K SO and So supported on SiO wherein said catalyst has a surface area of 40 m /g.
3. The process according to claim 1 wherein the oxygen is supplied to the reaction in the form of air.
4. The process according to claim 1 wherein the mol ratio of oxygen to butane 'in the feed is about 1:1.
:5. The process according to claim 1 wherein the reaction is carried out at a temperature of from about 500 the hydrocarbons, oxygen, and inerts in said stream.

Claims (8)

1. A PROCESS FOR THE OXIDATIVE DEHYDROGENATION OF BUTANE TO FORM A MIXTURE OF BUTENES AND BUTADIENE WHICH COMPRISES CONTACTING SAID BUTANE WITH OXYGEN IN THE PRESENCE OF AN OXIDATIVE DEHYDROGENATION CATALYST HAVIN A COMPOSITION OF ABOUT 9WT. PERCENT V2O5, ABOUT 29WT. PERCENT K2SO4, ABOUT 12WT. PERCENT SO2, AND ABOUT 50WT. PERCENT SIO2, WHEREIN THE REACTION IS CARRIED OUT AT TEMPERATURES OF FROM ABOUT 450* TO 650*C AND AT A GHSV OF FROM ABOUT 1000 TO 20,000 HR-1, AND WHEREIN THE RATIO OF OXYGEN TO BUTANE IS IN THE RANGE OF FROM ABOUT 1:1 TO 20:1.
2. The process according to claim 1 wherein the catalyst comprises V2O5 , K2SO4and SO2supported on SiO2, wherein said catalyst has a surface area of 40 m2/g.
3. The process according to claim 1 wherein the oxygen is supplied to the reaction in the form of air.
4. The process according to claim 1 wherein the mol ratio of oxygen to butane in the feed is about 1:1.
5. The process according to claim 1 wherein the reaction is carried out at a temperature of from about 500* to 600*C.
6. The process according to claim 1 wherein the GHSV is from 5000 to 15,000 hr. 1.
7. The process according to claim 1 wherein the butane is admixed with other C4to C6hydrocarbons.
8. The process according to claim 1 wherein the butane is present in the feed stream in amounts of from about 1 to 50wt. percent, based on the total weight of the hydrocarbons, oxygen, and inerts in said stream.
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Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4166916A (en) * 1977-03-23 1979-09-04 International Flavors & Fragrances Inc. Substituted bicyclooctenemethanols
EP0078247A3 (en) * 1981-10-21 1983-06-01 Monsanto Company Process and catalysts for vapor phase nitration of aromatic compounds
US4454245A (en) * 1981-12-07 1984-06-12 Union Oil Company Of California Catalyst and process for producing conjugated dienes
US4455388A (en) * 1981-12-07 1984-06-19 Union Oil Company Of California Catalyst and process for producing diolefins
US4555584A (en) * 1981-12-07 1985-11-26 Union Oil Company Of California Process for producing conjugated dienes
US4562269A (en) * 1981-12-07 1985-12-31 Union Oil Company Of California Method of producing maleic anhydride
US4564603A (en) * 1981-12-07 1986-01-14 Union Oil Company Of California Oxidative-dehydrogenation catalyst and process
US4567314A (en) * 1981-12-07 1986-01-28 Union Oil Company Of California Process for producing diolefins
US4599477A (en) * 1981-08-03 1986-07-08 Union Oil Company Of California Oxidative-dehydrogenation process
US4604371A (en) * 1981-06-19 1986-08-05 Union Oil Company Of California Oxidation catalyst
US4639530A (en) * 1981-06-19 1987-01-27 Union Oil Company Of California Process for making maleic anhydride
US4801567A (en) * 1981-06-19 1989-01-31 Union Oil Company Of California Oxidation catalyst
US8927455B2 (en) 2011-10-06 2015-01-06 Samsung Total Petrochemicals Co., Ltd. Single-step precipitation method of producing magnesia-zirconia complex carrier for catalyst for oxidative dehydrogenation of n-butane, magnesium orthovanadate catalyst supported on magnesia-zirconia complex carrier, and method of producing n-butene and 1,3-butadiene using said catalyst
WO2016075065A1 (en) * 2014-11-14 2016-05-19 Basf Se Method for producing 1,3-butadiene by dehydrogenating n-butenes, a material flow containing butanes and 2-butenes being provided
WO2016132293A1 (en) 2015-02-19 2016-08-25 Sabic Global Technologies B.V. Systems and methods related to the production of polyethylene
WO2016132292A1 (en) 2015-02-19 2016-08-25 Sabic Global Technologies B.V. Systems and methods related to the production of methyl tert-butyl ether
WO2016139594A1 (en) 2015-03-05 2016-09-09 Sabic Global Technologies B.V. Systems and methods related to the production of ethylene oxide, ethylene glycol, and/or ethanolamines
US9522383B2 (en) 2012-01-20 2016-12-20 Hanwha Total Petrochemical Co., Ltd. Method for preparing magnesia-zirconia composite carrier for catalyzing oxidative dehydration of normal-butane, method for preparing magnesium orthovanadate catalyst supported by magnesia-zirconia composite carrier prepared thereby, and method for preparing normal-butene and 1,3-butadiene using magnesium orthovanadate catalyst
US10358399B2 (en) 2014-11-03 2019-07-23 Basf Se Process for preparing 1,3-butadiene from n-butenes by oxidative dehydrogenation
US10927058B2 (en) 2015-05-15 2021-02-23 Sabic Global Technologies B.V. Systems and methods related to the syngas to olefin process
US10941348B2 (en) 2015-05-15 2021-03-09 Sabic Global Technologies B.V. Systems and methods related to syngas to olefin process

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US2973371A (en) * 1957-11-20 1961-02-28 American Cyanamid Co Phthalic anhydride catalysts of high surface area
US3218368A (en) * 1961-09-14 1965-11-16 Distillers Co Yeast Ltd Process for the preparation of unsaturated hydrocarbons
US3308196A (en) * 1965-10-22 1967-03-07 Petro Tex Chem Corp Oxidative dehydrogenation process
US3308191A (en) * 1965-10-22 1967-03-07 Petro Tex Chem Corp Oxidative dehydrogenation process
US3308200A (en) * 1965-10-22 1967-03-07 Petro Tex Chem Corp Oxidative dehydrogenation process
US3403192A (en) * 1965-03-29 1968-09-24 Exxon Research Engineering Co Sulfur-promoted oxidative dehydrogenation process
US3770812A (en) * 1970-05-28 1973-11-06 Eastman Kodak Co Catalytic formation of double bonds

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2973371A (en) * 1957-11-20 1961-02-28 American Cyanamid Co Phthalic anhydride catalysts of high surface area
US3218368A (en) * 1961-09-14 1965-11-16 Distillers Co Yeast Ltd Process for the preparation of unsaturated hydrocarbons
US3403192A (en) * 1965-03-29 1968-09-24 Exxon Research Engineering Co Sulfur-promoted oxidative dehydrogenation process
US3308196A (en) * 1965-10-22 1967-03-07 Petro Tex Chem Corp Oxidative dehydrogenation process
US3308191A (en) * 1965-10-22 1967-03-07 Petro Tex Chem Corp Oxidative dehydrogenation process
US3308200A (en) * 1965-10-22 1967-03-07 Petro Tex Chem Corp Oxidative dehydrogenation process
US3770812A (en) * 1970-05-28 1973-11-06 Eastman Kodak Co Catalytic formation of double bonds

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4166916A (en) * 1977-03-23 1979-09-04 International Flavors & Fragrances Inc. Substituted bicyclooctenemethanols
US4604371A (en) * 1981-06-19 1986-08-05 Union Oil Company Of California Oxidation catalyst
US4639530A (en) * 1981-06-19 1987-01-27 Union Oil Company Of California Process for making maleic anhydride
US4801567A (en) * 1981-06-19 1989-01-31 Union Oil Company Of California Oxidation catalyst
US4599477A (en) * 1981-08-03 1986-07-08 Union Oil Company Of California Oxidative-dehydrogenation process
EP0078247A3 (en) * 1981-10-21 1983-06-01 Monsanto Company Process and catalysts for vapor phase nitration of aromatic compounds
US4454245A (en) * 1981-12-07 1984-06-12 Union Oil Company Of California Catalyst and process for producing conjugated dienes
US4455388A (en) * 1981-12-07 1984-06-19 Union Oil Company Of California Catalyst and process for producing diolefins
US4555584A (en) * 1981-12-07 1985-11-26 Union Oil Company Of California Process for producing conjugated dienes
US4562269A (en) * 1981-12-07 1985-12-31 Union Oil Company Of California Method of producing maleic anhydride
US4564603A (en) * 1981-12-07 1986-01-14 Union Oil Company Of California Oxidative-dehydrogenation catalyst and process
US4567314A (en) * 1981-12-07 1986-01-28 Union Oil Company Of California Process for producing diolefins
US8927455B2 (en) 2011-10-06 2015-01-06 Samsung Total Petrochemicals Co., Ltd. Single-step precipitation method of producing magnesia-zirconia complex carrier for catalyst for oxidative dehydrogenation of n-butane, magnesium orthovanadate catalyst supported on magnesia-zirconia complex carrier, and method of producing n-butene and 1,3-butadiene using said catalyst
US9522383B2 (en) 2012-01-20 2016-12-20 Hanwha Total Petrochemical Co., Ltd. Method for preparing magnesia-zirconia composite carrier for catalyzing oxidative dehydration of normal-butane, method for preparing magnesium orthovanadate catalyst supported by magnesia-zirconia composite carrier prepared thereby, and method for preparing normal-butene and 1,3-butadiene using magnesium orthovanadate catalyst
US10358399B2 (en) 2014-11-03 2019-07-23 Basf Se Process for preparing 1,3-butadiene from n-butenes by oxidative dehydrogenation
WO2016075065A1 (en) * 2014-11-14 2016-05-19 Basf Se Method for producing 1,3-butadiene by dehydrogenating n-butenes, a material flow containing butanes and 2-butenes being provided
EA034435B1 (en) * 2014-11-14 2020-02-07 Басф Се Method for producing 1,3-butadienes by dehydrogenating n-butenes, a material flow containing butanes and 2-butenes being provided
US10384990B2 (en) 2014-11-14 2019-08-20 Basf Se Method for producing 1,3-butadiene by dehydrogenating n-butenes, a material flow containing butanes and 2-butenes being provided
CN107001186A (en) * 2014-11-14 2017-08-01 巴斯夫欧洲公司 Process for preparing 1,3-butadiene by dehydrogenation of n-butenes and providing a butane- and 2-butene-containing stream
US9969667B2 (en) 2015-02-19 2018-05-15 Sabic Global Technologies B.V. Systems and methods related to the production of methyl tert-butyl ether
US10308733B2 (en) 2015-02-19 2019-06-04 Sabic Global Technologies B.V. Systems and methods related to the production of polyethylene
WO2016132292A1 (en) 2015-02-19 2016-08-25 Sabic Global Technologies B.V. Systems and methods related to the production of methyl tert-butyl ether
WO2016132293A1 (en) 2015-02-19 2016-08-25 Sabic Global Technologies B.V. Systems and methods related to the production of polyethylene
WO2016139594A1 (en) 2015-03-05 2016-09-09 Sabic Global Technologies B.V. Systems and methods related to the production of ethylene oxide, ethylene glycol, and/or ethanolamines
US10604496B2 (en) 2015-03-05 2020-03-31 Sabic Global Technologies B.V. Systems and methods related to the production of ethylene oxide, ethylene glycol, and/or ethanolamines
US10927058B2 (en) 2015-05-15 2021-02-23 Sabic Global Technologies B.V. Systems and methods related to the syngas to olefin process
US10941348B2 (en) 2015-05-15 2021-03-09 Sabic Global Technologies B.V. Systems and methods related to syngas to olefin process

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