CN109219598B - 由丙烷制备丙烯和氧化丙烯的综合方法 - Google Patents
由丙烷制备丙烯和氧化丙烯的综合方法 Download PDFInfo
- Publication number
- CN109219598B CN109219598B CN201780030335.XA CN201780030335A CN109219598B CN 109219598 B CN109219598 B CN 109219598B CN 201780030335 A CN201780030335 A CN 201780030335A CN 109219598 B CN109219598 B CN 109219598B
- Authority
- CN
- China
- Prior art keywords
- stream
- propylene
- propane
- column
- propene
- 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.)
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Links
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 title claims abstract description 210
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 157
- 239000001294 propane Substances 0.000 title claims abstract description 78
- 238000000034 method Methods 0.000 title claims abstract description 41
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 88
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 63
- 238000006735 epoxidation reaction Methods 0.000 claims abstract description 47
- 239000003054 catalyst Substances 0.000 claims abstract description 29
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 22
- 239000011541 reaction mixture Substances 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000047 product Substances 0.000 description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 238000000926 separation method Methods 0.000 description 27
- 239000000203 mixture Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 229910052719 titanium Inorganic materials 0.000 description 6
- 239000010936 titanium Substances 0.000 description 6
- 238000004364 calculation method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000000895 extractive distillation Methods 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- -1 methanol Chemical compound 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- WLDGDTPNAKWAIR-UHFFFAOYSA-N 1,4,7-trimethyl-1,4,7-triazonane Chemical compound CN1CCN(C)CCN(C)CC1 WLDGDTPNAKWAIR-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 241000183024 Populus tremula Species 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
-
- 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
- C07C5/321—Catalytic processes
- C07C5/324—Catalytic processes with metals
-
- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
-
- 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
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (5)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP16169840.2A EP3246323A1 (en) | 2016-05-17 | 2016-05-17 | Integrated process for making propene oxide from propane |
EP16169840.2 | 2016-05-17 | ||
PCT/EP2017/061355 WO2017198546A1 (en) | 2016-05-17 | 2017-05-11 | Integrated process for making propene and propene oxide from propane |
Publications (2)
Publication Number | Publication Date |
---|---|
CN109219598A CN109219598A (zh) | 2019-01-15 |
CN109219598B true CN109219598B (zh) | 2022-11-29 |
Family
ID=56008515
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201780030335.XA Active CN109219598B (zh) | 2016-05-17 | 2017-05-11 | 由丙烷制备丙烯和氧化丙烯的综合方法 |
Country Status (8)
Country | Link |
---|---|
US (1) | US10597374B2 (zh) |
EP (1) | EP3246323A1 (zh) |
KR (1) | KR102156001B1 (zh) |
CN (1) | CN109219598B (zh) |
AR (1) | AR110464A1 (zh) |
RU (1) | RU2717556C1 (zh) |
TW (1) | TWI730093B (zh) |
WO (1) | WO2017198546A1 (zh) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3406603A1 (en) | 2017-05-22 | 2018-11-28 | Evonik Degussa GmbH | Process for the epoxidation of propene |
CA3097546A1 (en) * | 2018-04-16 | 2019-10-24 | Swift Fuels, Llc | Process for converting c2-c5 hydrocarbons to gasoline and diesel fuel blendstocks |
US10941357B2 (en) | 2018-04-16 | 2021-03-09 | Swift Fuels, Llc | Process for converting C2—C5 hydrocarbons to gasoline and diesel fuel blendstocks |
MX2022012328A (es) * | 2020-03-31 | 2023-06-22 | Chris Dacosta | Proceso para convertir hidrocarburos de c2-c5 a materiales de mezcla de combustible de gasolina y diesel. |
CN113461474A (zh) * | 2021-06-30 | 2021-10-01 | 中国石油化工股份有限公司 | 一种丙烷工业化连续制备环氧丙烷的系统及方法 |
CN113387906B (zh) * | 2021-06-30 | 2022-09-06 | 中国石油化工股份有限公司 | 一种丙烷连续生产环氧丙烷衍生物的方法 |
Citations (2)
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US5599956A (en) * | 1996-02-22 | 1997-02-04 | Uop | Integrated process for the production of propylene oxide |
WO2004020423A1 (de) * | 2002-08-30 | 2004-03-11 | Basf Aktiengesellschaft | Integriertes verfahren zur synthese von propylenoxid |
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BE1011577A3 (fr) | 1997-11-27 | 1999-11-09 | Solvay | Catalyseur d'epoxydation, son utilisation et procede d'epoxydation en presence de catalyseur. |
DE19936547A1 (de) | 1999-08-04 | 2001-02-15 | Basf Ag | Verfahren zur Umsetzung einer organischen Verbindung mit einem Hydroperoxid |
DE19944839A1 (de) | 1999-09-18 | 2001-03-22 | Degussa | Verfahren zur Herstellung von Epoxiden aus Olefinen |
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EP1247805A1 (en) | 2001-03-05 | 2002-10-09 | Degussa AG | Process for the epoxidation of olefins |
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ITMI20010859A1 (it) | 2001-04-24 | 2002-10-24 | Enichem Spa | Procedimento integrato per la produzione di ossidi olefinici |
EP1285915A1 (en) | 2001-08-16 | 2003-02-26 | Degussa AG | Continuous process to make epoxide from olefins and hydrogen peroxide |
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DE10233385A1 (de) | 2002-07-23 | 2004-02-12 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Propylenglykolen |
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DE10249377A1 (de) | 2002-10-23 | 2004-05-06 | Basf Ag | Verfahren zu kontinuierlichen Herstellung von Epoxiden aus Olefinen und Hydroperoxiden an einem suspendierten Katalysator |
DE10249378A1 (de) | 2002-10-23 | 2004-05-06 | Basf Ag | Verfahren zur kontinuierlichen Rückführung des bei der Oxidation von Olefinen mit Hydroperoxiden nicht umgesetzten Olefins mittels Verdichtung und Druckdestillation |
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EP3059230A1 (en) | 2015-02-17 | 2016-08-24 | Evonik Degussa GmbH | Method for the epoxidation of propene with hydrogen peroxide |
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JP6824269B2 (ja) | 2015-11-25 | 2021-02-03 | エボニック オペレーションズ ゲーエムベーハー | プロペンおよび過酸化水素から1,2−プロパンジオールを製造するための方法 |
EA033968B1 (ru) | 2015-11-26 | 2019-12-16 | Эвоник Дегусса Гмбх | Способ эпоксидирования олефина |
TWI707847B (zh) | 2015-11-26 | 2020-10-21 | 德商贏創運營有限公司 | 丙烯之環氧化方法 |
CN108430983B (zh) | 2015-11-26 | 2022-02-22 | 赢创运营有限公司 | 用于丙烯的环氧化的方法和反应器 |
HUE050560T2 (hu) | 2016-01-19 | 2020-12-28 | Evonik Operations Gmbh | Eljárás olefin epoxidálására |
EA035906B1 (ru) | 2016-03-21 | 2020-08-28 | Эвоник Оперейшнс Гмбх | Способ эпоксидирования пропилена |
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2016
- 2016-05-17 EP EP16169840.2A patent/EP3246323A1/en not_active Withdrawn
-
2017
- 2017-05-11 RU RU2018143581A patent/RU2717556C1/ru active
- 2017-05-11 WO PCT/EP2017/061355 patent/WO2017198546A1/en active Application Filing
- 2017-05-11 US US16/302,099 patent/US10597374B2/en active Active
- 2017-05-11 CN CN201780030335.XA patent/CN109219598B/zh active Active
- 2017-05-11 KR KR1020187036303A patent/KR102156001B1/ko active IP Right Grant
- 2017-05-12 TW TW106115856A patent/TWI730093B/zh active
- 2017-05-17 AR ARP170101310A patent/AR110464A1/es unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5599956A (en) * | 1996-02-22 | 1997-02-04 | Uop | Integrated process for the production of propylene oxide |
WO2004020423A1 (de) * | 2002-08-30 | 2004-03-11 | Basf Aktiengesellschaft | Integriertes verfahren zur synthese von propylenoxid |
Also Published As
Publication number | Publication date |
---|---|
WO2017198546A1 (en) | 2017-11-23 |
KR102156001B1 (ko) | 2020-09-16 |
RU2717556C1 (ru) | 2020-03-24 |
TW201815774A (zh) | 2018-05-01 |
EP3246323A1 (en) | 2017-11-22 |
TWI730093B (zh) | 2021-06-11 |
KR20190008895A (ko) | 2019-01-25 |
US10597374B2 (en) | 2020-03-24 |
US20190276419A1 (en) | 2019-09-12 |
CN109219598A (zh) | 2019-01-15 |
AR110464A1 (es) | 2019-04-03 |
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