TWI492933B - 抑制萃取精餾過程中乙烯基芳香族化合物聚合的方法 - Google Patents
抑制萃取精餾過程中乙烯基芳香族化合物聚合的方法 Download PDFInfo
- Publication number
- TWI492933B TWI492933B TW099120243A TW99120243A TWI492933B TW I492933 B TWI492933 B TW I492933B TW 099120243 A TW099120243 A TW 099120243A TW 99120243 A TW99120243 A TW 99120243A TW I492933 B TWI492933 B TW I492933B
- Authority
- TW
- Taiwan
- Prior art keywords
- vinyl aromatic
- aromatic compound
- polymerization
- styrene
- aromatic compounds
- Prior art date
Links
- -1 vinyl aromatic compounds Chemical class 0.000 title claims description 53
- 229920002554 vinyl polymer Polymers 0.000 title claims description 34
- 238000006116 polymerization reaction Methods 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 24
- 238000000895 extractive distillation Methods 0.000 title claims description 12
- 230000002401 inhibitory effect Effects 0.000 title claims description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 48
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 13
- 239000003112 inhibitor Substances 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 8
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 description 14
- 238000000197 pyrolysis Methods 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- 150000001491 aromatic compounds Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000356 contaminant Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- MHKBMNACOMRIAW-UHFFFAOYSA-N 2,3-dinitrophenol Chemical class OC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O MHKBMNACOMRIAW-UHFFFAOYSA-N 0.000 description 1
- HOYRZHJJAHRMLL-UHFFFAOYSA-N 2,6-dinitro-p-cresol Chemical compound CC1=CC([N+]([O-])=O)=C(O)C([N+]([O-])=O)=C1 HOYRZHJJAHRMLL-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000003949 liquefied natural gas Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
- B01D3/40—Extractive distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
- C07C7/05—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds
- C07C7/08—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds by extractive distillation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
- C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
- C07C15/46—Styrene; Ring-alkylated styrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/20—Use of additives, e.g. for stabilisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22662809P | 2009-07-17 | 2009-07-17 | |
| US12/705,937 US8771476B2 (en) | 2009-07-17 | 2010-02-15 | Methods for inhibiting polymerization of vinyl aromatic compounds during extractive distillation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201103889A TW201103889A (en) | 2011-02-01 |
| TWI492933B true TWI492933B (zh) | 2015-07-21 |
Family
ID=43449663
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW099120243A TWI492933B (zh) | 2009-07-17 | 2010-06-22 | 抑制萃取精餾過程中乙烯基芳香族化合物聚合的方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8771476B2 (enExample) |
| EP (1) | EP2453999A4 (enExample) |
| KR (1) | KR20120049270A (enExample) |
| CN (1) | CN101955409B (enExample) |
| BR (1) | BR112012001138A2 (enExample) |
| IN (1) | IN2012DN01380A (enExample) |
| RU (1) | RU2531918C2 (enExample) |
| TW (1) | TWI492933B (enExample) |
| WO (1) | WO2011008343A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2460714C1 (ru) * | 2011-06-27 | 2012-09-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Иркутский государственный технический университет" (ФГБОУ ВПО "ИрГТУ") | Способ ингибирования термополимеризации при переработке жидких продуктов пиролиза |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4514261A (en) * | 1984-08-31 | 1985-04-30 | El Paso Products Company | Refining of tertiary butylstyrene |
| US5446220A (en) * | 1994-08-24 | 1995-08-29 | Betz Laboratories, Inc. | Methods for inhibiting vinyl aromatic monomer polymerization |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1274784A (en) * | 1969-02-17 | 1972-05-17 | Toray Industries | Recovery of aromatic hydrocarbons |
| JPS5021B1 (enExample) * | 1970-07-18 | 1975-01-06 | ||
| US4033829A (en) * | 1974-12-26 | 1977-07-05 | Monsanto Company | Process for inhibiting polymerization of styrene during distillation |
| US4105506A (en) * | 1977-02-24 | 1978-08-08 | Cosden Technology, Inc. | Polymerization inhibitor for vinyl aromatic compounds |
| US4182658A (en) | 1977-11-23 | 1980-01-08 | Cosden Technology, Inc. | Emergency polymerization inhibitor system for vinyl aromatic compounds |
| DD135377A1 (de) * | 1978-02-23 | 1979-05-02 | Rainer Holm | Verfahren zur polymerisationsinhibierung bei der styrol-extraktivdestillation |
| US4252615A (en) * | 1978-07-18 | 1981-02-24 | Cosden Technology, Inc. | Polymerization inhibitor for vinyl aromatic compounds |
| US4596655A (en) * | 1983-08-17 | 1986-06-24 | The Dow Chemical Company | Process for separating an ethylenically unsaturated hydrocarbon from a hydrocarbon mixture |
| DE19513838A1 (de) * | 1994-05-02 | 1995-11-09 | Basf Ag | Verfahren zur Destillation von Styrol |
| ZA972966B (en) | 1996-05-21 | 1997-11-21 | Glitsch Int Inc | Recovery of styrene from purolysis gasoline by extractive distillation. |
| US5877385A (en) | 1996-05-21 | 1999-03-02 | Hfm International, Inc. | Process including extractive distillation and/or dehydrogenation to produce styrene from petroleum feedstock including ethyl-benzene/xylene mixtures |
| US5910232A (en) * | 1998-06-10 | 1999-06-08 | Nalco/Exxon Energy Chemicals, L.P. | Method for inhibiting polymer formation in styrene processing |
| US6395943B1 (en) * | 1999-08-10 | 2002-05-28 | Uop Llc | Process for inhibiting the polymerization of vinyl aromatic compounds |
| US6348136B1 (en) * | 2000-02-29 | 2002-02-19 | Fina Technology, Inc. | Method and apparatus for the purification of vinyl aromatic compounds |
-
2010
- 2010-02-15 US US12/705,937 patent/US8771476B2/en not_active Expired - Fee Related
- 2010-04-23 CN CN201010158962.1A patent/CN101955409B/zh not_active Expired - Fee Related
- 2010-05-22 BR BR112012001138A patent/BR112012001138A2/pt not_active IP Right Cessation
- 2010-05-22 KR KR1020127004130A patent/KR20120049270A/ko not_active Ceased
- 2010-05-22 EP EP10800200A patent/EP2453999A4/en not_active Withdrawn
- 2010-05-22 WO PCT/US2010/035889 patent/WO2011008343A1/en not_active Ceased
- 2010-05-22 RU RU2012105429/04A patent/RU2531918C2/ru not_active IP Right Cessation
- 2010-05-22 IN IN1380DEN2012 patent/IN2012DN01380A/en unknown
- 2010-06-22 TW TW099120243A patent/TWI492933B/zh not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4514261A (en) * | 1984-08-31 | 1985-04-30 | El Paso Products Company | Refining of tertiary butylstyrene |
| US5446220A (en) * | 1994-08-24 | 1995-08-29 | Betz Laboratories, Inc. | Methods for inhibiting vinyl aromatic monomer polymerization |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101955409B (zh) | 2014-11-26 |
| EP2453999A4 (en) | 2013-01-23 |
| IN2012DN01380A (enExample) | 2015-06-05 |
| RU2531918C2 (ru) | 2014-10-27 |
| EP2453999A1 (en) | 2012-05-23 |
| TW201103889A (en) | 2011-02-01 |
| KR20120049270A (ko) | 2012-05-16 |
| US20110015462A1 (en) | 2011-01-20 |
| CN101955409A (zh) | 2011-01-26 |
| RU2012105429A (ru) | 2013-08-27 |
| WO2011008343A1 (en) | 2011-01-20 |
| US8771476B2 (en) | 2014-07-08 |
| BR112012001138A2 (pt) | 2016-02-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |