KR101256964B1 - 탈수소화에 의해 알킬화 촉매 독물들의 처리 - Google Patents
탈수소화에 의해 알킬화 촉매 독물들의 처리 Download PDFInfo
- Publication number
- KR101256964B1 KR101256964B1 KR1020077019187A KR20077019187A KR101256964B1 KR 101256964 B1 KR101256964 B1 KR 101256964B1 KR 1020077019187 A KR1020077019187 A KR 1020077019187A KR 20077019187 A KR20077019187 A KR 20077019187A KR 101256964 B1 KR101256964 B1 KR 101256964B1
- Authority
- KR
- South Korea
- Prior art keywords
- dehydrogenation
- alkylation
- output stream
- offtest
- catalyst
- Prior art date
Links
- 238000006356 dehydrogenation reaction Methods 0.000 title claims abstract description 52
- 238000005804 alkylation reaction Methods 0.000 title claims abstract description 34
- 230000029936 alkylation Effects 0.000 title claims abstract description 32
- 239000003054 catalyst Substances 0.000 title claims abstract description 32
- 231100000614 poison Toxicity 0.000 title claims description 6
- 238000000034 method Methods 0.000 claims abstract description 43
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000012535 impurity Substances 0.000 claims abstract description 14
- 230000000694 effects Effects 0.000 claims abstract description 3
- 231100000419 toxicity Toxicity 0.000 claims abstract description 3
- 230000001988 toxicity Effects 0.000 claims abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 33
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 22
- -1 alkyl aromatic hydrocarbon Chemical class 0.000 claims description 22
- 238000000926 separation method Methods 0.000 claims description 17
- 239000002574 poison Substances 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 229910021536 Zeolite Inorganic materials 0.000 claims 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims 1
- 239000002808 molecular sieve Substances 0.000 claims 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims 1
- 239000010457 zeolite Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 7
- 238000011084 recovery Methods 0.000 description 5
- 238000009835 boiling Methods 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- 238000010555 transalkylation reaction Methods 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 description 2
- 150000002830 nitrogen compounds Chemical class 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 1
- DYPHJEMAXTWPFB-UHFFFAOYSA-N [K].[Fe] Chemical compound [K].[Fe] DYPHJEMAXTWPFB-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- ZHXNYTNBAFVFPG-UHFFFAOYSA-N cesium iron(2+) oxygen(2-) Chemical compound [O-2].[Fe+2].[Cs+] ZHXNYTNBAFVFPG-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
Images
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
-
- 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
-
- 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
- B01J38/00—Regeneration or reactivation of catalysts, in general
-
- 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
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Description
Claims (17)
- 알킬 방향족 탄화수소를 탈수소화 시스템으로 도입하는 단계;비닐 방향족 탄화수소를 포함하는 탈수소화 출력 스트림을 형성하기 위해 알킬 방향족 탄화수소를 탈수소화 촉매와 접촉시키는 단계;제1 분리 컬럼 및 적어도 하나의 추가의 분리 컬럼을 포함하는 분리 시스템에 탈수소화 출력 스트림의 적어도 일부를 통과시키는 단계;탈수소화 공정으로부터 스티렌을 포함하는 오프테스트(offtest)를 회수하는 단계; 및상기 오프테스트를 추가의 분리 컬럼들 중의 적어도 하나 내로 도입하는 단계를 포함하는 탈수소화 방법.
- 제1항에 있어서, 상기 분리 시스템은 3개의 분리 컬럼들을 포함하는 것인 방법.
- 제1항에 있어서, 상기 탈수소화 시스템 내로 스팀을 도입하는 것을 추가로 포함하는 방법.
- 제3항에 있어서, 상기 스팀 대 알킬 방향족 탄화수소 중량비는 0.01:1 내지 15:1인 방법.
- 제1항에 있어서, 상기 알킬 방향족 탄화수소는 에틸벤젠을 포함하는 것인 방법.
- 제5항에 있어서, 상기 비닐 방향족 탄화수소는 스티렌을 포함하는 것인 방법.
- 제6항에 있어서, 상기 출력 스트림은 에틸벤젠을 추가로 포함하는 것인 방법.
- 제1항에 있어서, 상기 제1 분리 컬럼으로부터 오버헤드 분획을 알킬화 시스템으로 통과시키는 단계 및 제1 분리 컬럼으로부터 바닥 분획을 적어도 하나의 추가의 분리 컬럼으로 통과시키는 단계를 추가로 포함하는 방법.
- 제8항에 있어서, 상기 오버헤드 분획은 알킬화 시스템 내에서 알킬화 촉매와 접촉하는 것인 방법.
- 제9항에 있어서, 상기 알킬화 촉매는 분자체 촉매를 포함하는 것인 방법.
- 제9항에 있어서, 상기 오버헤드 분획은 벤젠 및 불순물을 포함하는 것인 방법.
- 제11항에 있어서, 상기 불순물은 질소 함유 화합물들을 포함하는 것인 방법.
- 제8항에 있어서, 상기 오버헤드 분획은 제1 분리 컬럼으로 공급된 오프테스트를 갖는 동일한 시스템 내의 오버헤드 분획보다 적은 불순물을 포함하는 것인 방법.
- 탈수소화 시스템 내에 탈수소화 출력 스트림을 형성하도록 에틸벤젠을 탈수소화 촉매와 접촉시키는 단계; 및탈수소화 출력 스트림의 적어도 일부가 알킬화 촉매와 접촉하는 알킬화 시스템에 탈수소화 출력 스트림의 적어도 일부를 통과시키는 단계를 포함하고,탈수소화 출력 스트림의 적어도 일부는 스티렌을 포함하는 오프테스트(offtest)로부터 기인하는 불순물을 포함하는데, 상기 오프테스트로부터 기인한 불순물이 알킬화 촉매의 수명에 미치는 효과는 상기 오프테스트가 없는 알킬화 시스템과 비교하여 차이가 없는 것을 특징으로 하는 알킬화 촉매 유독성의 감소 방법.
- 제14항에 있어서, 상기 탈수소화 출력 스트림은 벤젠을 포함하는 것인 방법.
- 제14항에 있어서, 상기 알킬화 촉매는 제올라이트 알킬화 촉매를 포함하는 것인 방법.
- 제1항에 있어서, 상기 오프테스트는 상기 추가의 분리 컬럼들 중의 적어도 하나를 통과하게 되고 그리고 상기 탈수소화 시스템으로 재순환되며, 상기 오프테스트에 존재하는 독물(poisons)은 상기 탈수소화 시스템에서 태워지는(burned) 것인 방법.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US65646405P | 2005-02-25 | 2005-02-25 | |
US60/656,464 | 2005-02-25 | ||
PCT/US2006/005406 WO2006093672A2 (en) | 2005-02-25 | 2006-02-15 | Treatment of alkylation catalyst poisons with dehydrogenation |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20070107057A KR20070107057A (ko) | 2007-11-06 |
KR101256964B1 true KR101256964B1 (ko) | 2013-04-26 |
Family
ID=36941608
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020077019187A KR101256964B1 (ko) | 2005-02-25 | 2006-02-15 | 탈수소화에 의해 알킬화 촉매 독물들의 처리 |
Country Status (7)
Country | Link |
---|---|
US (2) | US20060194992A1 (ko) |
EP (1) | EP1853535A4 (ko) |
KR (1) | KR101256964B1 (ko) |
CN (1) | CN101124187B (ko) |
CA (1) | CA2595689C (ko) |
TW (1) | TWI395620B (ko) |
WO (1) | WO2006093672A2 (ko) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008130553A1 (en) * | 2007-04-16 | 2008-10-30 | Mallinckrodt Inc. | Novel opiate reduction utilizing catalytic hydrogen transfer reaction |
WO2014084810A1 (en) | 2012-11-27 | 2014-06-05 | Badger Licensing Llc | Production of styrene |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3525776A (en) * | 1968-11-12 | 1970-08-25 | Universal Oil Prod Co | Alkylation-dehydrogenation process |
US7094939B1 (en) * | 2002-09-23 | 2006-08-22 | Uop Llc | Styrene process with recycle from dehydrogenation zone |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4009217A (en) * | 1975-05-06 | 1977-02-22 | Universal Oil Products Company | Process for production and dehydrogenation of ethylbenzene |
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 |
US4914249A (en) * | 1988-12-29 | 1990-04-03 | Uop | Dehydrogenation of dehydrogenatable hydrocarbons |
US6376729B1 (en) * | 2000-12-04 | 2002-04-23 | Fina Technology, Inc. | Multi-phase alkylation process |
FR2844790B1 (fr) * | 2002-09-20 | 2004-10-22 | Inst Francais Du Petrole | Procede de coproduction de paraxylene et de styrene |
-
2006
- 2006-02-15 CA CA2595689A patent/CA2595689C/en not_active Expired - Fee Related
- 2006-02-15 EP EP06735188A patent/EP1853535A4/en not_active Withdrawn
- 2006-02-15 CN CN2006800055101A patent/CN101124187B/zh not_active Expired - Fee Related
- 2006-02-15 KR KR1020077019187A patent/KR101256964B1/ko not_active IP Right Cessation
- 2006-02-15 WO PCT/US2006/005406 patent/WO2006093672A2/en active Application Filing
- 2006-02-21 TW TW095105806A patent/TWI395620B/zh not_active IP Right Cessation
- 2006-02-24 US US11/361,817 patent/US20060194992A1/en not_active Abandoned
-
2008
- 2008-12-03 US US12/327,682 patent/US7696394B2/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3525776A (en) * | 1968-11-12 | 1970-08-25 | Universal Oil Prod Co | Alkylation-dehydrogenation process |
US7094939B1 (en) * | 2002-09-23 | 2006-08-22 | Uop Llc | Styrene process with recycle from dehydrogenation zone |
Also Published As
Publication number | Publication date |
---|---|
CN101124187B (zh) | 2012-05-23 |
EP1853535A2 (en) | 2007-11-14 |
KR20070107057A (ko) | 2007-11-06 |
TW200635664A (en) | 2006-10-16 |
TWI395620B (zh) | 2013-05-11 |
CN101124187A (zh) | 2008-02-13 |
CA2595689A1 (en) | 2006-09-08 |
EP1853535A4 (en) | 2010-08-25 |
US20090149685A1 (en) | 2009-06-11 |
WO2006093672A3 (en) | 2007-09-07 |
US20060194992A1 (en) | 2006-08-31 |
WO2006093672A2 (en) | 2006-09-08 |
CA2595689C (en) | 2013-04-23 |
US7696394B2 (en) | 2010-04-13 |
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