DE2034358A1 - Herstellung von Athylenoxid - Google Patents
Herstellung von AthylenoxidInfo
- Publication number
- DE2034358A1 DE2034358A1 DE19702034358 DE2034358A DE2034358A1 DE 2034358 A1 DE2034358 A1 DE 2034358A1 DE 19702034358 DE19702034358 DE 19702034358 DE 2034358 A DE2034358 A DE 2034358A DE 2034358 A1 DE2034358 A1 DE 2034358A1
- Authority
- DE
- Germany
- Prior art keywords
- ethylene
- mol
- oxygen
- reaction mixture
- oxidation reaction
- 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
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 title claims description 38
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 72
- 239000005977 Ethylene Substances 0.000 claims description 71
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 57
- 239000001301 oxygen Substances 0.000 claims description 47
- 229910052760 oxygen Inorganic materials 0.000 claims description 47
- 238000006243 chemical reaction Methods 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 44
- 239000003112 inhibitor Substances 0.000 claims description 42
- 238000007254 oxidation reaction Methods 0.000 claims description 42
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 37
- 239000003054 catalyst Substances 0.000 claims description 24
- 239000011541 reaction mixture Substances 0.000 claims description 22
- 230000003647 oxidation Effects 0.000 claims description 19
- 229910001882 dioxygen Inorganic materials 0.000 claims description 17
- 239000007789 gas Substances 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 11
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 9
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 5
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 4
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 4
- 229940117389 dichlorobenzene Drugs 0.000 claims description 4
- 230000005764 inhibitory process Effects 0.000 claims description 3
- 229920006389 polyphenyl polymer Polymers 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229920000265 Polyparaphenylene Polymers 0.000 claims 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims 1
- 150000004074 biphenyls Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- -1 polyphenylene Polymers 0.000 claims 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 30
- 230000008569 process Effects 0.000 description 25
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 238000002474 experimental method Methods 0.000 description 18
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 239000001569 carbon dioxide Substances 0.000 description 15
- 229910002092 carbon dioxide Inorganic materials 0.000 description 15
- 229910052786 argon Inorganic materials 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000012495 reaction gas Substances 0.000 description 9
- 238000005755 formation reaction Methods 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000007792 addition Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 229910010271 silicon carbide Inorganic materials 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910000975 Carbon steel Inorganic materials 0.000 description 1
- 241001292396 Cirrhitidae Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000012215 calcium aluminium silicate Nutrition 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000010962 carbon steel Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
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
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
- C07D301/08—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase
- C07D301/10—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase with catalysts containing silver or gold
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84083869A | 1969-07-10 | 1969-07-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2034358A1 true DE2034358A1 (de) | 1971-01-14 |
Family
ID=25283359
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702034358 Pending DE2034358A1 (de) | 1969-07-10 | 1970-07-10 | Herstellung von Athylenoxid |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5238007B1 (enExample) |
| BE (1) | BE752859R (enExample) |
| CS (1) | CS177035B2 (enExample) |
| DE (1) | DE2034358A1 (enExample) |
| FR (1) | FR2054320A6 (enExample) |
| GB (1) | GB1314613A (enExample) |
| IT (1) | IT947038B (enExample) |
| LU (1) | LU61263A1 (enExample) |
| NL (1) | NL7010114A (enExample) |
| SE (1) | SE382633B (enExample) |
| ZA (1) | ZA704771B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3262507D1 (en) * | 1981-01-23 | 1985-04-18 | Ici Plc | Process for the production of ethylene oxide |
| US7193094B2 (en) | 2001-11-20 | 2007-03-20 | Shell Oil Company | Process and systems for the epoxidation of an olefin |
| DE602004009776T2 (de) | 2003-04-01 | 2008-08-28 | Shell Internationale Research Maatschappij B.V. | Olefinepoxidationsverfahren und katalysator zur verwendung bei dem verfahren |
| CA2758818C (en) | 2009-04-21 | 2018-05-29 | Dow Technology Investments Llc | Simplified method for producing alkylene oxides with a high efficiency catalyst as it ages |
| CA2759496C (en) | 2009-04-21 | 2018-05-01 | Dow Technology Investments Llc | Epoxidation reactions and operating conditions thereof |
| US8362284B2 (en) | 2009-04-21 | 2013-01-29 | Dow Technology Investments Llc | Method of achieving and maintaining a specified alkylene oxide production parameter with a high efficiency catalyst |
| AU2012210661B2 (en) | 2011-01-24 | 2015-04-30 | Shell Internationale Research Maatschappij B.V. | Process for the production of ethylene oxide |
| WO2012101092A1 (en) | 2011-01-24 | 2012-08-02 | Shell Internationale Research Maatschappij B.V. | Process for the production of ethylene oxide |
| EP2644604A1 (en) | 2012-03-30 | 2013-10-02 | Shell Internationale Research Maatschappij B.V. | Process for the production of ethylene oxide |
| JP6368118B2 (ja) | 2014-03-31 | 2018-08-01 | 株式会社日本触媒 | エチレンオキシドの製造方法 |
| CA2996656C (en) | 2015-09-18 | 2024-01-16 | Shell Internationale Research Maatschappij B.V. | Alkane oxidative dehydrogenation |
| WO2017134164A1 (en) | 2016-02-04 | 2017-08-10 | Shell Internationale Research Maatschappij B.V. | Conversion of mixed methane/ethane streams |
| TW201943709A (zh) | 2018-04-09 | 2019-11-16 | 荷蘭商蜆殼國際研究公司 | 用於生產環氧乙烷之方法 |
| AR116926A1 (es) | 2018-11-02 | 2021-06-30 | Shell Int Research | Separación de efluente de deshidrogenación oxidativa de etano |
-
1970
- 1970-07-02 BE BE752859D patent/BE752859R/xx active
- 1970-07-06 LU LU61263D patent/LU61263A1/xx unknown
- 1970-07-08 FR FR7025266A patent/FR2054320A6/fr not_active Expired
- 1970-07-08 NL NL7010114A patent/NL7010114A/xx not_active Application Discontinuation
- 1970-07-08 GB GB3314670A patent/GB1314613A/en not_active Expired
- 1970-07-09 SE SE7009528A patent/SE382633B/xx unknown
- 1970-07-10 DE DE19702034358 patent/DE2034358A1/de active Pending
- 1970-07-10 JP JP45060001A patent/JPS5238007B1/ja active Pending
- 1970-07-10 IT IT52048/70A patent/IT947038B/it active
- 1970-07-10 CS CS4889A patent/CS177035B2/cs unknown
- 1970-07-10 ZA ZA704771A patent/ZA704771B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5238007B1 (enExample) | 1977-09-27 |
| CS177035B2 (enExample) | 1977-07-29 |
| BE752859R (fr) | 1971-01-04 |
| LU61263A1 (enExample) | 1972-04-04 |
| NL7010114A (enExample) | 1971-01-12 |
| ZA704771B (en) | 1972-02-23 |
| GB1314613A (en) | 1973-04-26 |
| FR2054320A6 (enExample) | 1971-04-16 |
| IT947038B (it) | 1973-05-21 |
| SE382633B (sv) | 1976-02-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |