CA3029396A1 - Process for the conversion of methane into propanal - Google Patents
Process for the conversion of methane into propanal Download PDFInfo
- Publication number
- CA3029396A1 CA3029396A1 CA3029396A CA3029396A CA3029396A1 CA 3029396 A1 CA3029396 A1 CA 3029396A1 CA 3029396 A CA3029396 A CA 3029396A CA 3029396 A CA3029396 A CA 3029396A CA 3029396 A1 CA3029396 A1 CA 3029396A1
- Authority
- CA
- Canada
- Prior art keywords
- reactor
- ethylene
- stream
- syngas
- water
- 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.)
- Pending
Links
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title claims abstract description 127
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 title claims abstract description 88
- 238000000034 method Methods 0.000 title claims abstract description 55
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 52
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 77
- 239000005977 Ethylene Substances 0.000 claims abstract description 77
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 50
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims abstract description 41
- 239000003054 catalyst Substances 0.000 claims abstract description 32
- 239000007789 gas Substances 0.000 claims abstract description 32
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 27
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000001301 oxygen Substances 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 238000005691 oxidative coupling reaction Methods 0.000 claims abstract description 9
- 239000000376 reactant Substances 0.000 claims abstract description 6
- 238000010574 gas phase reaction Methods 0.000 claims abstract description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 39
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 37
- 238000004227 thermal cracking Methods 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 5
- 239000012530 fluid Substances 0.000 claims description 4
- 238000003303 reheating Methods 0.000 claims description 4
- 238000011144 upstream manufacturing Methods 0.000 claims 2
- 238000007037 hydroformylation reaction Methods 0.000 description 44
- 239000000047 product Substances 0.000 description 21
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 15
- 229910001882 dioxygen Inorganic materials 0.000 description 15
- 238000000926 separation method Methods 0.000 description 9
- 238000002407 reforming Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 238000005336 cracking Methods 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000004088 simulation Methods 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 229910052976 metal sulfide Inorganic materials 0.000 description 3
- 239000003345 natural gas Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 239000003039 volatile agent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- -1 for example Chemical compound 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000006709 oxidative esterification reaction Methods 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- PXXVOLRLZXINTK-UHFFFAOYSA-N propanal Chemical compound CCC=O.CCC=O PXXVOLRLZXINTK-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
- C07C45/505—Asymmetric hydroformylation
-
- 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
- B01J6/00—Heat treatments such as Calcining; Fusing ; Pyrolysis
- B01J6/008—Pyrolysis reactions
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B3/00—Hydrogen; Gaseous mixtures containing hydrogen; Separation of hydrogen from mixtures containing it; Purification of hydrogen
- C01B3/02—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen
- C01B3/06—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of inorganic compounds containing electro-positively bound hydrogen, e.g. water, acids, bases, ammonia, with inorganic reducing agents
- C01B3/12—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of inorganic compounds containing electro-positively bound hydrogen, e.g. water, acids, bases, ammonia, with inorganic reducing agents by reaction of water vapour with carbon monoxide
- C01B3/16—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of inorganic compounds containing electro-positively bound hydrogen, e.g. water, acids, bases, ammonia, with inorganic reducing agents by reaction of water vapour with carbon monoxide using catalysts
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B3/00—Hydrogen; Gaseous mixtures containing hydrogen; Separation of hydrogen from mixtures containing it; Purification of hydrogen
- C01B3/02—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen
- C01B3/32—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide, air
- C01B3/34—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide, air by reaction of hydrocarbons with gasifying agents
- C01B3/36—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide, air by reaction of hydrocarbons with gasifying agents using oxygen or mixtures containing oxygen as gasifying agents
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B3/00—Hydrogen; Gaseous mixtures containing hydrogen; Separation of hydrogen from mixtures containing it; Purification of hydrogen
- C01B3/02—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen
- C01B3/32—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide, air
- C01B3/34—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide, air by reaction of hydrocarbons with gasifying agents
- C01B3/48—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide, air by reaction of hydrocarbons with gasifying agents followed by reaction of water vapour with carbon monoxide
-
- 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
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/76—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen
- C07C2/82—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen oxidative coupling
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/76—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen
- C07C2/82—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen oxidative coupling
- C07C2/84—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation of hydrocarbons with partial elimination of hydrogen oxidative coupling catalytic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
-
- 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
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
-
- 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
- C07C5/32—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by dehydrogenation with formation of free hydrogen
- C07C5/327—Formation of non-aromatic carbon-to-carbon double bonds only
- C07C5/333—Catalytic processes
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B2203/00—Integrated processes for the production of hydrogen or synthesis gas
- C01B2203/02—Processes for making hydrogen or synthesis gas
- C01B2203/0283—Processes for making hydrogen or synthesis gas containing a CO-shift step, i.e. a water gas shift step
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B2203/00—Integrated processes for the production of hydrogen or synthesis gas
- C01B2203/06—Integration with other chemical processes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Combustion & Propulsion (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662356786P | 2016-06-30 | 2016-06-30 | |
| US62/356,786 | 2016-06-30 | ||
| PCT/US2017/037159 WO2018005074A1 (en) | 2016-06-30 | 2017-06-13 | Process for the conversion of methane into propanal |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3029396A1 true CA3029396A1 (en) | 2018-01-04 |
Family
ID=59216020
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA3029396A Pending CA3029396A1 (en) | 2016-06-30 | 2017-06-13 | Process for the conversion of methane into propanal |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US10519087B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3478631B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6920023B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR102379397B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN109311666B (cg-RX-API-DMAC7.html) |
| BR (1) | BR112018075821B1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA3029396A1 (cg-RX-API-DMAC7.html) |
| MX (1) | MX2018015552A (cg-RX-API-DMAC7.html) |
| SA (1) | SA518400731B1 (cg-RX-API-DMAC7.html) |
| SG (1) | SG11201811444YA (cg-RX-API-DMAC7.html) |
| WO (1) | WO2018005074A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10519087B2 (en) | 2016-06-30 | 2019-12-31 | Dow Global Technologies Llc | Process for the conversion of methane into propanal |
| EP3976661A4 (en) | 2019-05-24 | 2023-03-29 | Eastman Chemical Company | CELLULOSIC ESTERS WITH RECYCLED CONTENT |
| US11946000B2 (en) | 2019-05-24 | 2024-04-02 | Eastman Chemical Company | Blend small amounts of pyoil into a liquid stream processed into a gas cracker |
| WO2020247192A1 (en) | 2019-05-24 | 2020-12-10 | Eastman Chemical Company | Recycle content cracked effluent |
| US11365357B2 (en) | 2019-05-24 | 2022-06-21 | Eastman Chemical Company | Cracking C8+ fraction of pyoil |
| EP3976573A4 (en) * | 2019-05-24 | 2023-07-05 | Eastman Chemical Company | PROPIONALDEHYDE WITH RECYCLED CONTENT |
| DE102019119540A1 (de) * | 2019-07-18 | 2021-01-21 | Linde Gmbh | Verfahren und Anlage zur Herstellung einer Zielverbindung |
| DE102019119543A1 (de) * | 2019-07-18 | 2021-01-21 | Linde Gmbh | Verfahren und Anlage zur Herstellung einer Zielverbindung |
| DE102019119562A1 (de) * | 2019-07-18 | 2021-01-21 | Linde Gmbh | Verfahren und Anlage zur Herstellung einer Zielverbindung |
| US12338211B2 (en) | 2019-07-29 | 2025-06-24 | Eastman Chemical Company | Recycle content (C4)alkanal |
| CN114641555A (zh) | 2019-10-31 | 2022-06-17 | 伊士曼化工公司 | 用于回收废物的热解方法和系统 |
| US11945998B2 (en) | 2019-10-31 | 2024-04-02 | Eastman Chemical Company | Processes and systems for making recycle content hydrocarbons |
| US11319262B2 (en) | 2019-10-31 | 2022-05-03 | Eastman Chemical Company | Processes and systems for making recycle content hydrocarbons |
| EP4054997A4 (en) | 2019-11-07 | 2024-02-21 | Eastman Chemical Company | ALPHA-OLEFINS AND FAT ALCOHOLS WITH RECYCLING CONTENT |
| WO2021092305A1 (en) | 2019-11-07 | 2021-05-14 | Eastman Chemical Company | Recycle content mixed esters and solvents |
| CN118851872A (zh) * | 2019-11-07 | 2024-10-29 | 伊士曼化工公司 | 回收成分丙醇 |
| EP3922621B1 (de) | 2020-06-10 | 2023-08-30 | Linde GmbH | Prozess zur herstellung von propylen |
| EP4015495A1 (de) * | 2020-12-18 | 2022-06-22 | Linde GmbH | Verfahren und anlage zur herstellung einer zielverbindung |
| KR102536935B1 (ko) * | 2020-12-31 | 2023-05-26 | 주식회사 카카오 | 사용자 프로필 관리 방법 및 장치 |
| US12195674B2 (en) | 2021-09-21 | 2025-01-14 | Eastman Chemical Company | Using spent caustic solution from pygas treatment to neutralize halogens from liquified waste plastic |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR19980701460A (ko) | 1995-01-18 | 1998-05-15 | 보덴 피터 챨스 | 하이드로포르밀화 공정(hydroformylation process) |
| CA2261269A1 (en) * | 1996-04-01 | 1997-10-09 | Barbara Knight Warren | Processes for the manufacture of methylmercaptopropanal |
| CN1298859A (zh) * | 1999-12-09 | 2001-06-13 | 中国科学院成都有机化学研究所 | 一种天然气旋焰乙炔炉余热喷油产混合气的使用方法 |
| CN100551884C (zh) * | 2005-12-02 | 2009-10-21 | 四川大学 | 一种由甲烷氧化偶联和气相氧化耦合制取丙醛原料的方法 |
| US20120065412A1 (en) * | 2009-05-20 | 2012-03-15 | Basf Se | System and process for producing higher-value hydrocarbons from methane |
| EP2499111B1 (en) | 2009-11-11 | 2018-07-04 | Dow Global Technologies LLC | Reductive hydroformylation of an alkylene to an alkanol |
| DE102010030209A1 (de) * | 2010-06-17 | 2011-12-22 | Evonik Oxeno Gmbh | Energieeffiziente Synthese von aliphatischen Adelhyden aus Alkanen und Kohlendioxid |
| CN102442894B (zh) * | 2010-09-30 | 2014-08-06 | 中国石油化工股份有限公司 | 一种利用炼厂干气中乙烯制备丙醛的方法 |
| CA2828727A1 (en) | 2011-03-02 | 2012-09-07 | Mark Allen Nunley | Methods for integrated natural gas purification and products produced therefrom |
| US9012694B2 (en) * | 2011-12-27 | 2015-04-21 | Shell Oil Company | Process for the production of alcohols |
| AU2013355038B2 (en) | 2012-12-07 | 2017-11-02 | Lummus Technology Llc | Integrated processes and systems for conversion of methane to multiple higher hydrocarbon products |
| US20160107143A1 (en) | 2013-03-15 | 2016-04-21 | Siluria Technologies, Inc. | Catalysts for petrochemical catalysis |
| BR112016006652B1 (pt) * | 2013-09-30 | 2020-12-01 | Dow Global Technologies Llc | processo e processo de duas etapas |
| WO2015057753A1 (en) * | 2013-10-16 | 2015-04-23 | Saudi Basic Industries Corporation | Method for converting methane to ethylene |
| US10351643B2 (en) | 2013-11-29 | 2019-07-16 | Dic Corporation | Polymerizable compounds, compositions, polymers, optically anisotropic articles, liquid crystal display devices and organic EL devices |
| US10519087B2 (en) | 2016-06-30 | 2019-12-31 | Dow Global Technologies Llc | Process for the conversion of methane into propanal |
-
2017
- 2017-06-13 US US16/304,469 patent/US10519087B2/en active Active
- 2017-06-13 MX MX2018015552A patent/MX2018015552A/es unknown
- 2017-06-13 CA CA3029396A patent/CA3029396A1/en active Pending
- 2017-06-13 JP JP2018565774A patent/JP6920023B2/ja active Active
- 2017-06-13 KR KR1020197001767A patent/KR102379397B1/ko active Active
- 2017-06-13 BR BR112018075821-3A patent/BR112018075821B1/pt active IP Right Grant
- 2017-06-13 CN CN201780039024.XA patent/CN109311666B/zh active Active
- 2017-06-13 WO PCT/US2017/037159 patent/WO2018005074A1/en not_active Ceased
- 2017-06-13 EP EP17733247.5A patent/EP3478631B1/en active Active
- 2017-06-13 SG SG11201811444YA patent/SG11201811444YA/en unknown
-
2018
- 2018-12-23 SA SA518400731A patent/SA518400731B1/ar unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2019519547A (ja) | 2019-07-11 |
| SG11201811444YA (en) | 2019-01-30 |
| US10519087B2 (en) | 2019-12-31 |
| BR112018075821A2 (pt) | 2019-03-26 |
| KR102379397B1 (ko) | 2022-03-28 |
| BR112018075821B1 (pt) | 2022-11-16 |
| EP3478631B1 (en) | 2020-04-22 |
| SA518400731B1 (ar) | 2021-12-12 |
| MX2018015552A (es) | 2019-06-06 |
| CN109311666A (zh) | 2019-02-05 |
| JP6920023B2 (ja) | 2021-08-18 |
| US20190292122A1 (en) | 2019-09-26 |
| CN109311666B (zh) | 2022-07-19 |
| WO2018005074A1 (en) | 2018-01-04 |
| EP3478631A1 (en) | 2019-05-08 |
| KR20190024967A (ko) | 2019-03-08 |
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