WO2020074750A1 - Alkane oxidative dehydrogenation and/or alkene oxidation - Google Patents
Alkane oxidative dehydrogenation and/or alkene oxidation Download PDFInfo
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- WO2020074750A1 WO2020074750A1 PCT/EP2019/083960 EP2019083960W WO2020074750A1 WO 2020074750 A1 WO2020074750 A1 WO 2020074750A1 EP 2019083960 W EP2019083960 W EP 2019083960W WO 2020074750 A1 WO2020074750 A1 WO 2020074750A1
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- Prior art keywords
- alkane
- alkene
- vol
- catalyst
- oxygen
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- 150000001335 aliphatic alkanes Chemical class 0.000 title claims abstract description 77
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 69
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 title claims abstract description 22
- 230000003647 oxidation Effects 0.000 title claims abstract description 17
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 17
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 66
- 238000000034 method Methods 0.000 claims abstract description 56
- 239000003085 diluting agent Substances 0.000 claims abstract description 47
- 239000003054 catalyst Substances 0.000 claims abstract description 36
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 33
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 33
- 239000001301 oxygen Substances 0.000 claims abstract description 33
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 13
- 229910003455 mixed metal oxide Inorganic materials 0.000 claims abstract description 11
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical group CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 35
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 20
- 239000005977 Ethylene Substances 0.000 claims description 20
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 239000001294 propane Substances 0.000 claims description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 8
- 239000010955 niobium Substances 0.000 claims description 7
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 5
- 229910052750 molybdenum Inorganic materials 0.000 claims description 5
- 239000011733 molybdenum Substances 0.000 claims description 5
- 229910052758 niobium Inorganic materials 0.000 claims description 4
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 4
- 229910052714 tellurium Inorganic materials 0.000 claims description 4
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims description 4
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 43
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000007789 gas Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000012018 catalyst precursor Substances 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- -1 ethylene, propylene, butene Chemical class 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000001354 calcination Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000001694 spray drying Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 229910052756 noble gas Inorganic materials 0.000 description 2
- 150000002835 noble gases Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000007580 dry-mixing Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- FXADMRZICBQPQY-UHFFFAOYSA-N orthotelluric acid Chemical compound O[Te](O)(O)(O)(O)O FXADMRZICBQPQY-UHFFFAOYSA-N 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-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
- C07C5/42—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
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/04—Ethylene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/215—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of saturated hydrocarbyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/25—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring
- C07C51/252—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of unsaturated compounds containing no six-membered aromatic ring of propene, butenes, acrolein or methacrolein
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/08—Acetic acid
-
- 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
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
-
- 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
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/50—Constitutive chemical elements of heterogeneous catalysts of Group V (VA or VB) of the Periodic Table
- B01J2523/55—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
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/60—Constitutive chemical elements of heterogeneous catalysts of Group VI (VIA or VIB) of the Periodic Table
- B01J2523/64—Tellurium
-
- 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
- B01J2523/00—Constitutive chemical elements of heterogeneous catalysts
- B01J2523/60—Constitutive chemical elements of heterogeneous catalysts of Group VI (VIA or VIB) of the Periodic Table
- B01J2523/68—Molybdenum
-
- 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
- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/20—Vanadium, niobium or tantalum
-
- 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
- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/20—Vanadium, niobium or tantalum
- C07C2523/22—Vanadium
-
- 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
- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/24—Chromium, molybdenum or tungsten
- C07C2523/28—Molybdenum
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
- C07C2527/057—Selenium or tellurium; Compounds thereof
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Definitions
- the present invention relates to a process for alkane oxidative dehydrogenation and/or alkene oxidation.
- alkanes such as alkanes containing 2 to 6 carbon atoms, for example ethane or propane resulting in ethylene and propylene, respectively, in an oxidative dehydrogenation (oxydehydrogenation; ODH) process.
- ODH oxidative dehydrogenation
- Mo molybdenum
- V vanadium
- Nb niobium
- Te tellurium
- Such catalysts may also be used in the direct oxidation of alkenes to carboxylic acids, such as in the oxidation of alkenes containing 2 to 6 carbon atoms, for example ethylene or propylene resulting in acetic acid and acrylic acid, respectively.
- US20160326070 disclose a process for oxydehydrogenating an alkane to a corresponding alkene comprising: providing a feed of at least an alkane and oxygen as oxidizing agent to a reactor; converting the alkane to a product stream which includes the corresponding alkene by oxydehydrogenation of the alkane with oxygen in the reactor in the presence of a catalyst, wherein the feed further includes a diluent
- An “overall conversion” of a compound “A” is generally defined as (moles of A reacted overall)/ (mole of fresh feed), whereas a “conversion per pass” is defined as (moles of A reacted in a single pass) /(mole of A fed to the reactor) .
- a relatively high ratio of recycle unconverted reactant to fresh reactant is needed to keep the conversion per pass low to safeguard a certain desired selectivity.
- one or more of the above- mentioned objects may be achieved by contacting an alkane and/or alkene with oxygen in the presence of a catalyst comprising a mixed metal oxide and one or more diluents selected from the group consisting of carbon dioxide, carbon monoxide and steam, wherein the conversion of the alkane and/or alkene is at least 40%.
- the present invention relates to a process of the oxidative dehydrogenation of an alkane containing 2 to 6 carbon atoms and/or the oxidation of an alkene containing 2 to 6 carbon atoms, wherein the alkane and/or alkene is contacted with oxygen in the presence of a catalyst
- composition or stream used in said process are described in terms of “comprising”, “containing” or “including” one or more various described steps and components, they can also “consist essentially of” or “consist of” said one or more various described steps and components.
- composition or stream comprises two or more components
- these components are to be selected in an overall amount not to exceed 100%.
- substantially no means that no detectible amount of the component in question is present in the composition or stream.
- fresh alkane reference is made to alkane which does not comprise unconverted alkane.
- unconverted alkane reference is made to alkane that was subjected to the process of the present invention for the first time, but which was not converted. Similar definitions for "fresh alkene” and “unconverted alkene” apply.
- alkane oxidative dehydrogenation and/or alkene oxidation process
- an alkane containing 2 to 6 carbon atoms hereinafter the "alkane”
- alkene an alkane containing 2 to 6 carbon atoms
- the oxidation of an alkene containing 2 to 6 carbon atoms hereinafter the alkene
- alkene is contacted with oxygen in the presence of a catalyst comprising a mixed metal oxide and one or more diluents selected from the group consisting of carbon
- the conversion of the alkane and/or alkene is at least 40%.
- conversion per pass is defined as (moles of alkane and/or alkene reacted in a single pass)/ (mole of alkane and/or alkene fed to the reactor) .
- conversion per pass can be controlled by varying one or more parameters. Such parameters include temperature, pressure, nature of the catalyst, amount of the catalyst and amount of oxygen .
- the conversion per pass of the alkane and/or alkene is controlled to be at least 40%. It has appeared that at such relatively high conversion per pass, the selectivity to the desired product (s) may still be relatively high in the presence of a diluent selected from the group consisting of carbon dioxide, carbon monoxide and steam. Thus, advantageously, in the present invention wherein such diluent is used, the conversion per pass can be
- the desired products comprise ethylene and acetic acid
- the desired product comprises acetic acid
- the conversion per pass of the alkane and/or alkene is controlled to be at least 45%, more preferably at least 50%, more preferably at least
- said conversion per pass is at most 99%, more preferably at most 95%, more preferably at most 90%, more preferably at most
- the alkane is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl
- containing 2 to 6 carbon atoms is a linear alkane in which case said alkane may be selected from the group consisting of ethane, propane, butane, pentane and hexane. Further, preferably, said alkane contains 2 to 4 carbon atoms and is selected from the group consisting of ethane, propane and butane. More preferably, said alkane is ethane or propane. Most preferably, said alkane is ethane. In case an alkane is used, the present invention is referred to as an alkane oxidative dehydrogenation process.
- the alkene containing 2 to 6 carbon atoms is a linear alkene in which case said alkene may be selected from the group consisting of ethylene, propylene, butene, pentene and hexene. Further, preferably, said alkene contains 2 to 4 carbon atoms and is selected from the group consisting of ethylene, propylene and butene. More preferably, said alkene is ethylene or
- alkene oxidation process the present invention is referred to as an alkene oxidation process.
- the product of said alkane oxidative dehydrogenation process may comprise the dehydrogenated equivalent of the alkane, that is to say the corresponding alkene.
- the dehydrogenated equivalent of the alkane is initially formed in said alkane oxidative dehydrogenation process.
- said dehydrogenated equivalent may be further oxidized under the same conditions into the corresponding carboxylic acid which may or may not contain one or more unsaturated double carbon-carbon bonds.
- containing 2 to 6 carbon atoms is ethane or propane.
- ethane the product of said alkane oxidative
- dehydrogenation process may comprise ethylene and/or acetic acid, preferably ethylene.
- product of said alkane oxidative dehydrogenation process may comprise propylene and/or acrylic acid, preferably acrylic acid.
- the product of said alkene oxidation process comprises the oxidized equivalent of the alkene.
- said oxidized equivalent of the alkene is the corresponding carboxylic acid.
- Said carboxylic acid may or may not contain one or more unsaturated double carbon-carbon bonds.
- the alkene containing 2 to 6 carbon atoms is ethylene or propylene.
- the product of said alkene oxidation process may comprise acetic acid.
- the product of said alkene oxidation process may comprise acrylic acid .
- the alkane and/or alkene, oxygen (0 2) and the one or more diluents may be fed to a reactor.
- Said components may be fed to the reactor together or separately. That is to say, one or more feed streams, suitably gas streams, comprising one or more of said
- one feed stream comprising oxygen, the alkane and/or alkene and diluent may be fed to the reactor.
- two or more feed streams, suitably gas streams, may be fed to the
- feed streams may form a combined stream inside the reactor.
- one feed stream comprising oxygen, another feed stream comprising the alkane and/or alkene and still another feed stream comprising diluent may be fed to the reactor separately.
- the alkane and/or alkene, oxygen and diluent are suitably fed to a reactor in the gas phase.
- the temperature is of from 300 to 500 °C. More preferably, said temperature is of from 310 to 450 °C, more preferably of from 320 to 420 °C, most
- typical pressures are 0.1-30 or 0.1-20 bara (i.e. "bar absolute") .
- said pressure is of from 0.1 to 15 bara, more preferably of from 1 to 12 bara, most preferably of from 2 to 12 bara. Said pressure refers to total pressure.
- a diluent is used.
- the diluent comprises one or more diluents selected from the group consisting of carbon dioxide (CO2) , carbon monoxide (CO) and steam (H2O) .
- CO2 carbon dioxide
- CO carbon monoxide
- H2O steam
- the diluent comprises carbon dioxide.
- the diluent may comprise carbon dioxide and
- diluents selected from the group consisting of methane, nitrogen, carbon monoxide and steam, preferably steam and/or nitrogen.
- the diluent may comprise carbon monoxide and optionally one or more diluents selected from the group consisting of carbon dioxide,
- methane nitrogen and steam, preferably steam and/or
- diluent is also fed to the present process.
- carbon dioxide is fed to the present process as a diluent
- one or more additional diluents selected from the group consisting of the noble gases, nitrogen, steam and methane, suitably nitrogen and methane, may be fed to the present process.
- the proportion of the overall feed stream to the present process which is attributable to a diluent is in the range from 5 to 90 vol.%, preferably from 25 to 75 vol.%. Said proportion may be at least 5 vol.% or at least 10 vol.% or at least 15 vol.% or at least 20 vol.% or at least 25 vol.% and may be at most 90 vol.% or at most 80 vol.% or at most 70 vol.% or at most 60 vol.% or at most 50 vol.% or at most 45 vol.% or at most 40 vol.% or at most 35 vol.%.
- the proportion of the overall feed stream to the present process which is attributable to a diluent is in the range from 5 to 90 vol.%, preferably from 25 to 75 vol.% and more preferably from 40 to 60 vol.%.
- the proportion of the overall feed stream to the present process which is attributable to a diluent is in the range from 50 to 95 vol.%, preferably from 60 to 90 vol.% and more preferably from 70 to 85 vol.%.
- the diluent as fed to the present process comprises from 1 to 100 vol.%, more preferably 5 to 100 vol.%, more preferably 10 to 100 vol.%, more preferably 20 to 100 vol.%, more preferably 40 to 100 vol.%, more preferably 60 to 100 vol.%, more preferably 80 to 100 vol.%, more preferably 90 to 100 vol.%, more preferably 95 to 100 vol.%, and most preferably 99 to 100 vol.% of carbon dioxide, the balance consisting of one or more other diluents, selected from the group consisting of the noble gases, nitrogen, steam and methane. Diluents other than carbon dioxide may be used in any desired ratio relative to each other.
- the upper limit for the proportion of carbon dioxide in the diluent may be 20 vol.%, preferably 40 vol.%, more preferably 60 vol.%, more preferably 80 vol.%, more preferably 90 vol.%, more preferably 95 vol.%, and most preferably 99 vol.%.
- the oxygen as fed to the present process is an oxidizing agent, thereby resulting in oxidative dehydrogenation (ODH) of the alkane or oxidation of the alkene.
- Said oxygen may originate from any source, such as for example air.
- the molar ratio of oxygen to the alkane and/or alkene is of from 0.05 to 0.5, more
- the molar ratio of oxygen to the alkane and/or alkene is of from 0.5 to 1.1, more suitably of from 0.53 to 1, most suitably of from 0.55 to 0.9. Said ratio of oxygen to alkane and/or alkene is the ratio before oxygen and the alkane and/or alkene are
- said ratio of oxygen to the alkane and/or alkene is the ratio of oxygen as fed to the alkane and/or alkene as fed.
- said "alkane and/or alkene" in said molar ratio of oxygen to the alkane and/or alkene comprises both fresh alkane and/or alkene and recycled (unconverted) alkane and/or alkene.
- pure or substantially pure oxygen (0 2) is used as oxidizing agent in the process of the present
- pure or substantially pure oxygen reference is made to oxygen that may contain a relatively small amount of one or more
- N2 nitrogen
- N2 nitrogen
- N2 nitrogen
- N2 nitrogen
- ppmv 7,000 parts per million by volume
- ppmv 8,000 ppmv
- ppmv 1,000 ppmv
- 500 ppmv more suitably at most 300 ppmv
- 200 ppmv more suitably at most 200 ppmv
- 100 ppmv more suitably at most 50 ppmv
- 30 ppmv most suitably at most 10 ppmv .
- air or oxygen-enriched air it is also possible to use air or oxygen-enriched air as oxidizing agent in the present
- Such air or oxygen-enriched air would still comprise nitrogen (N 2) , in an amount exceeding 1 vol.% up to 78 vol.% (air), suitably of from 1 to 50% vol.%, more suitably 1 to 30 vol.%, more suitably 1 to 20 vol.%, more suitably 1 to 10 vol.%, most suitably 1 to 5 vol.%. Said nitrogen would function as (additional) diluent.
- the catalyst is a catalyst comprising a mixed metal oxide.
- the catalyst is a heterogeneous catalyst.
- the catalyst is a mixed metal oxide catalyst containing molybdenum, vanadium, niobium and optionally tellurium as the metals, which
- a, b, c and n represent the ratio of the molar amount of the element in question to the molar amount of molybdenum (Mo) ;
- a (for V) is from 0.01 to 1, preferably 0.05 to 0.60, more preferably 0.10 to 0.40, more preferably 0.20 to 0.35, most preferably 0.25 to 0.30;
- b (for Te) is 0 or from >0 to 1, preferably 0.01 to 0.40, more preferably 0.05 to 0.30, more preferably 0.05 to 0.20, most preferably 0.09 to 0.15;
- c (for Nb) is from >0 to 1, preferably 0.01 to 0.40, more preferably 0.05 to 0.30, more preferably 0.10 to 0.25, most preferably 0.14 to 0.20;
- n (for 0) is a number which is determined by the valency and frequency of elements other than oxygen.
- the amount of the catalyst in the present invention is not essential.
- a catalytically effective amount of the catalyst is used, that is to say an amount sufficient to promote the reaction.
- the ODH reactor that may be used in the present process may be any reactor, including fixed-bed and fluidized-bed reactors.
- the reactor is a fixed-bed reactor.
- oxydehydrogenation processes including catalysts and process conditions, are for example disclosed in above-mentioned US7091377, W02003064035, US20040147393, W02010096909 and US20100256432, the disclosures of which are herein incorporated by reference.
- the work-up of the product stream resulting from the present process may be carried out in any known way. Further, unconverted alkane and/or alkene may be recycled to the present process. Preferably, diluent is also recycled, in particular carbon dioxide. Such work-up and recycle may for example be carried out in a way as disclosed in above- mentioned US20160326070, the disclosure of which is herein incorporated by reference. Further, for example, in the case of methane and/or carbon monoxide in the product stream, such methane and/or carbon monoxide may be separated in a
- demethanizer as a top stream and then recycled to the present process for use as diluent.
- the present invention is further illustrated by the following Examples.
- a mixed metal oxide catalyst containing molybdenum (Mo) , vanadium (V) , niobium (Nb) and tellurium (Te) was prepared, for which catalyst the molar ratio of said 4 metals was
- Solution 1 was obtained by dissolving 15.8 parts by weight (pbw) of ammonium niobate oxalate and 4 pbw of oxalic acid dihydrate in 160 pbw of water at room temperature.
- Solution 2 was prepared by
- solution 2 into solution 1 under vigorous stirring, which yielded an orange gel-like precipitate (suspension) having a temperature of about 45 °C.
- This suspension was then aged for about 15 minutes.
- the suspension was then dried by means of spray drying to remove the water, which yielded a dry, fine powder (the catalyst precursor) .
- Precipitation and spray drying were executed portion wise at a scale to yield 1 kg of dried material per portion. Said spray drying was carried out by using an air temperature of around 180 °C resulting in a solid temperature of around 80 ° C .
- pre-calcination was carried out in a static ventilated oven wherein the dried catalyst precursor was contacted with air.
- 250 g portions of catalyst precursor were heated from room temperature to 325 °C at a rate of 100 °C/hour and kept at 325 °C for 2 hours and then cooled down.
- the cooled catalyst precursor was then removed from the oven and further calcined in a nitrogen (N 2 ) stream in a retort oven.
- the catalyst precursor was heated from room temperature to 600 °C at a rate of 100 °C/hour and kept at 600 °C for 2 hours, after which the catalyst was cooled down to room temperature.
- the flow of the stream in this calcination step was 150 Nl/hr.
- Bindzil CC301 a 30 wt . % suspension of silanized silica particles
- the catalyst thus prepared was used in experiments involving ethane oxidative dehydrogenation within a pilot plant unit comprising a vertically oriented, cylindrical, stainless steel reactor having an inner diameter of 19 mm. 1.96 kg of the catalyst were loaded in the reactor. The catalyst bed height was 5.6 m.
- the flow rates in the 1 st row are in Nl/hour, wherein “Nl” stands for “normal litre” as measured at standard temperature and pressure, namely 32 °F (0 °C) and 1 bara (100 kPa) .
- the flow rate for "Total Diluent” is the sum of the flow rates for CPU, CO2 and N2.
- volume percentages for flow rates in the 2 nd row for each experiment are based on the overall feed stream, including all flow rates for CH4, CO2, N2, C2H6 and O2.
- XC2H6 refers to conversion (per pass) of ethane (%) .
- SC2H4 refers to selectivity towards ethylene (%) .
- sAA refers to selectivity towards acetic acid (%) .
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Priority Applications (12)
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CA3119825A CA3119825A1 (en) | 2018-12-11 | 2019-12-06 | Alkane oxidative dehydrogenation and/or alkene oxidation |
EP19813857.0A EP3894379A1 (en) | 2018-12-11 | 2019-12-06 | Alkane oxidative dehydrogenation and/or alkene oxidation |
EA202191626A EA202191626A1 (en) | 2018-12-11 | 2019-12-06 | OXIDATIVE ALKANE DEHYDRATION AND / OR ALKENE OXIDATION |
PE2021000841A PE20212191A1 (en) | 2018-12-11 | 2019-12-06 | OXIDATIVE DEHYDROGENATION OF ALKANES AND/OR OXIDATION OF ALKENE |
AU2019356177A AU2019356177B2 (en) | 2018-12-11 | 2019-12-06 | Alkane oxidative dehydrogenation and/or alkene oxidation |
MX2021006545A MX2021006545A (en) | 2018-12-11 | 2019-12-06 | Alkane oxidative dehydrogenation and/or alkene oxidation. |
CN201980081190.5A CN113165999A (en) | 2018-12-11 | 2019-12-06 | Alkane oxidative dehydrogenation and/or alkene oxidation |
KR1020217017340A KR20210102893A (en) | 2018-12-11 | 2019-12-06 | Oxidative dehydrogenation of alkanes and/or oxidation of alkenes |
JP2021533207A JP2022511934A (en) | 2018-12-11 | 2019-12-06 | Oxidative dehydrogenation of alkanes and / or oxidation of alkenes |
US17/311,535 US20220055972A1 (en) | 2018-12-11 | 2019-12-06 | Alkane oxidative dehydrogenation and/or alkene oxidation |
BR112021009809-7A BR112021009809A2 (en) | 2018-12-11 | 2019-12-06 | process of the oxidative dehydrogenation of an alkane containing 2 to 6 carbon atoms and/or the oxidation of an alkene containing 2 to 6 carbon atoms |
IL283766A IL283766B1 (en) | 2018-12-11 | 2019-12-06 | Alkane oxidative dehydrogenation and/or alkene oxidation |
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CN (1) | CN113165999A (en) |
AR (1) | AR117679A1 (en) |
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BR (1) | BR112021009809A2 (en) |
CA (1) | CA3119825A1 (en) |
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WO2021250492A1 (en) * | 2020-06-09 | 2021-12-16 | Nova Chemicals (International) S.A. | Forming acetic acid by the selective oxidation of light hydrocarbons |
EP4015495A1 (en) | 2020-12-18 | 2022-06-22 | Linde GmbH | Method and system for producing a target connection |
DE102021202495A1 (en) | 2021-03-15 | 2022-09-15 | Clariant International Ltd. | METHOD AND EQUIPMENT FOR ESTABLISHING A TARGET CONNECTION |
EP4059595A1 (en) | 2021-03-15 | 2022-09-21 | Linde GmbH | Production of ethylene by oxidative dehydrogenation of ethane |
EP4116283A1 (en) | 2021-07-06 | 2023-01-11 | Linde GmbH | Method and system for producing vinyl acetate |
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2019
- 2019-12-06 BR BR112021009809-7A patent/BR112021009809A2/en unknown
- 2019-12-06 US US17/311,535 patent/US20220055972A1/en not_active Abandoned
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- 2019-12-06 EP EP19813857.0A patent/EP3894379A1/en not_active Withdrawn
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- 2019-12-06 AU AU2019356177A patent/AU2019356177B2/en active Active
- 2019-12-06 CA CA3119825A patent/CA3119825A1/en active Pending
- 2019-12-06 WO PCT/EP2019/083960 patent/WO2020074750A1/en active Search and Examination
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EA202191626A1 (en) | 2021-09-10 |
TW202021936A (en) | 2020-06-16 |
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IL283766A (en) | 2021-07-29 |
AR117679A1 (en) | 2021-08-25 |
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US20220055972A1 (en) | 2022-02-24 |
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