CA2726533C - Process for the production of styrene monomer by improving energy efficiency - Google Patents
Process for the production of styrene monomer by improving energy efficiency Download PDFInfo
- Publication number
- CA2726533C CA2726533C CA2726533A CA2726533A CA2726533C CA 2726533 C CA2726533 C CA 2726533C CA 2726533 A CA2726533 A CA 2726533A CA 2726533 A CA2726533 A CA 2726533A CA 2726533 C CA2726533 C CA 2726533C
- Authority
- CA
- Canada
- Prior art keywords
- ethylbenzene
- gaseous
- vaporizer
- carbon dioxide
- styrene monomer
- 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.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 48
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 19
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims abstract description 322
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 104
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 52
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 50
- 238000009835 boiling Methods 0.000 claims abstract description 32
- 239000007788 liquid Substances 0.000 claims abstract description 31
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 239000006200 vaporizer Substances 0.000 claims description 62
- 239000007789 gas Substances 0.000 claims description 51
- 239000008246 gaseous mixture Substances 0.000 claims description 13
- 230000003197 catalytic effect Effects 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
- 229910052786 argon Inorganic materials 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000011261 inert gas Substances 0.000 description 6
- 239000007800 oxidant agent Substances 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-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
- C07C5/32—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
- 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
-
- 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
- Y02P20/141—Feedstock
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (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 |
|---|---|---|---|
| US12/139,456 US7910784B2 (en) | 2008-06-14 | 2008-06-14 | Process for the production of styrene monomer by improving energy efficiency and injecting a recycle gas into the EB vaporizer |
| US12/139,456 | 2008-06-14 | ||
| PCT/US2009/047214 WO2009152438A1 (en) | 2008-06-14 | 2009-06-12 | Process for the production of styrene monomer by improving energy efficiency |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2726533A1 CA2726533A1 (en) | 2009-12-17 |
| CA2726533C true CA2726533C (en) | 2013-07-30 |
Family
ID=41415400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2726533A Expired - Fee Related CA2726533C (en) | 2008-06-14 | 2009-06-12 | Process for the production of styrene monomer by improving energy efficiency |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7910784B2 (enExample) |
| EP (1) | EP2303811A4 (enExample) |
| JP (1) | JP2011524370A (enExample) |
| KR (1) | KR101241504B1 (enExample) |
| CN (1) | CN102056871A (enExample) |
| AR (1) | AR074152A1 (enExample) |
| BR (1) | BRPI0914853A2 (enExample) |
| CA (1) | CA2726533C (enExample) |
| CL (1) | CL2009001403A1 (enExample) |
| MX (1) | MX2010013718A (enExample) |
| RU (1) | RU2443667C1 (enExample) |
| TW (1) | TW201010966A (enExample) |
| WO (1) | WO2009152438A1 (enExample) |
| ZA (1) | ZA201008779B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101130922B1 (ko) * | 2010-01-06 | 2012-03-28 | 삼성토탈 주식회사 | 복수의 단열반응기들이 직렬 연결된 스티렌 제조 반응시스템에서의 생산성 및 공정안정성 개선 방법 |
| KR101888261B1 (ko) * | 2015-12-22 | 2018-08-13 | 주식회사 엘지화학 | 에너지가 절감된 스타이렌과 알파메틸스타이렌의 동시 제조 방법 및 장치 |
| KR101997814B1 (ko) * | 2015-12-22 | 2019-07-08 | 주식회사 엘지화학 | 스타이렌과 알파메틸스타이렌의 동시 제조 방법 및 장치 |
| CN114436744B (zh) * | 2020-10-20 | 2024-06-28 | 中国石油化工股份有限公司 | 乙苯脱氢制备苯乙烯的方法和系统 |
| CN114456027B (zh) * | 2020-10-21 | 2024-06-28 | 中国石油化工股份有限公司 | 一种乙苯脱氢制苯乙烯的装置和方法 |
| CN114456037B (zh) * | 2020-10-21 | 2024-06-28 | 中国石油化工股份有限公司 | 乙苯脱氢制苯乙烯的原料气化方法 |
| CN116410050A (zh) * | 2023-03-27 | 2023-07-11 | 江苏常青树新材料科技股份有限公司 | 一种co2氧化甲乙苯脱氢制备甲基苯乙烯的工艺方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3904484A (en) * | 1972-09-07 | 1975-09-09 | Badger Co | Ethylbenzene-styrene separation |
| US4628136A (en) * | 1985-12-17 | 1986-12-09 | Lummus Crest, Inc. | Dehydrogenation process for production of styrene from ethylbenzene comprising low temperature heat recovery and modification of the ethylbenzene-steam feed therewith |
| US4765398A (en) * | 1987-05-06 | 1988-08-23 | Lummus Crest, Inc. | Vaporization of liquids |
| US5053572A (en) * | 1989-05-11 | 1991-10-01 | Amoco Corporation | Multistage ethylbenzene dehydrogenation process with split-flow hydrocarbon feed |
| JPH0639437B2 (ja) * | 1989-09-21 | 1994-05-25 | 出光石油化学株式会社 | スチレンの製造方法 |
| KR100331021B1 (ko) * | 1993-01-04 | 2002-11-27 | 셰브론케미칼컴파니 | 탈수소화방법 |
| JP3032816B2 (ja) * | 1997-08-13 | 2000-04-17 | 工業技術院長 | スチレンモノマーの製造方法 |
| JP4154877B2 (ja) * | 2000-08-18 | 2008-09-24 | 三菱化学株式会社 | スチレンの製造方法 |
| JP2002097162A (ja) * | 2000-09-19 | 2002-04-02 | Idemitsu Petrochem Co Ltd | スチレンの製造方法および製造装置 |
| JP3950952B2 (ja) * | 2001-03-08 | 2007-08-01 | 独立行政法人産業技術総合研究所 | スチレンモノマーの製造方法 |
| ITMI20012709A1 (it) * | 2001-12-20 | 2003-06-20 | Snam Progetti | Composizione catalitica per la deidrogenazione di idrocarburi alchilaromatici |
| KR20030072541A (ko) | 2002-03-04 | 2003-09-15 | 한국화학연구원 | 이산화탄소 산화제를 사용한 알킬방향족 탄화수소의탈수소화 방법 |
| MY135793A (en) * | 2002-07-12 | 2008-06-30 | Basf Ag | Method for the production of butadiene from n-butane |
| KR100665759B1 (ko) | 2005-02-17 | 2007-01-09 | 삼성토탈 주식회사 | 개선된 에너지 효율을 갖는 스티렌의 제조방법 |
| CA2857176C (en) | 2006-03-23 | 2016-08-30 | Velocys, Inc. | Process for making styrene using microchannel process technology |
-
2008
- 2008-06-14 US US12/139,456 patent/US7910784B2/en not_active Expired - Fee Related
-
2009
- 2009-06-12 CA CA2726533A patent/CA2726533C/en not_active Expired - Fee Related
- 2009-06-12 EP EP09763726.8A patent/EP2303811A4/en not_active Withdrawn
- 2009-06-12 CN CN2009801216195A patent/CN102056871A/zh active Pending
- 2009-06-12 TW TW098119680A patent/TW201010966A/zh unknown
- 2009-06-12 BR BRPI0914853A patent/BRPI0914853A2/pt not_active IP Right Cessation
- 2009-06-12 JP JP2011513729A patent/JP2011524370A/ja not_active Ceased
- 2009-06-12 RU RU2011101358/04A patent/RU2443667C1/ru not_active IP Right Cessation
- 2009-06-12 CL CL2009001403A patent/CL2009001403A1/es unknown
- 2009-06-12 KR KR1020107027125A patent/KR101241504B1/ko not_active Expired - Fee Related
- 2009-06-12 MX MX2010013718A patent/MX2010013718A/es active IP Right Grant
- 2009-06-12 WO PCT/US2009/047214 patent/WO2009152438A1/en not_active Ceased
- 2009-06-16 AR ARP090102176A patent/AR074152A1/es not_active Application Discontinuation
-
2010
- 2010-12-07 ZA ZA2010/08779A patent/ZA201008779B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2303811A4 (en) | 2014-04-30 |
| US20090312590A1 (en) | 2009-12-17 |
| WO2009152438A1 (en) | 2009-12-17 |
| BRPI0914853A2 (pt) | 2015-10-27 |
| US7910784B2 (en) | 2011-03-22 |
| EP2303811A1 (en) | 2011-04-06 |
| JP2011524370A (ja) | 2011-09-01 |
| CL2009001403A1 (es) | 2010-01-04 |
| RU2443667C1 (ru) | 2012-02-27 |
| KR101241504B1 (ko) | 2013-03-11 |
| MX2010013718A (es) | 2011-04-11 |
| CA2726533A1 (en) | 2009-12-17 |
| CN102056871A (zh) | 2011-05-11 |
| KR20110031279A (ko) | 2011-03-25 |
| TW201010966A (en) | 2010-03-16 |
| AR074152A1 (es) | 2010-12-29 |
| ZA201008779B (en) | 2012-01-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20150612 |