US20050085677A1 - Method for improved production of cyclohexenyl and alkenyl aromatic compounds - Google Patents
Method for improved production of cyclohexenyl and alkenyl aromatic compounds Download PDFInfo
- Publication number
- US20050085677A1 US20050085677A1 US10/685,633 US68563303A US2005085677A1 US 20050085677 A1 US20050085677 A1 US 20050085677A1 US 68563303 A US68563303 A US 68563303A US 2005085677 A1 US2005085677 A1 US 2005085677A1
- Authority
- US
- United States
- Prior art keywords
- water
- nitrogen
- benzene
- aromatic compound
- compounds
- 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.)
- Abandoned
Links
Classifications
-
- 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
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Definitions
- This invention relates to the preparation of cyclohexenyl and alkenyl aromatic compounds.
- the invention relates to the preparation of styrene.
- Styrene is utilized widely in the plastics industry for the manufacture of plastics, rubber-modified impact polystyrene, acrylonitrile-butadiene-styrene terpolymer, styrene acrylonitrile copolymer, styrene-butadiene type synthetic rubber, and a host of other copolymers, terpolymers, and the like.
- styrene feed which is converted, via alkylation, to ethylbenzene and then, via continuous dehydrogenation, to a process stream comprising styrene, toluene and benzene products.
- the dehydrogenation may be done catalytically in an adiabatic or isothermal reactor.
- Primary products are styrene, unreacted ethylbenzene, and smaller amounts of toluene and benzene.
- the process stream components are then separated via a distillation columns, with the styrene and toluene being recovered as products, and the benzene being recycled to begin the alkylation phase again.
- a problem that is encountered during this process is that additives such as amines for neutralization of carbonic acid in process water and inhibitors to decrease styrene polymerization are added.
- Common stabilizers and neutralizers include amine compounds, which effectively inhibit the styrene homopolymerization and neutralize the carbonic acid but unfortunately byproducts are then retained with the benzene fraction.
- Such nitrogen compounds are undesirable in the benzene fraction because they tend to interfere with the alkylation and/or hydrogenation catalysts when the benzene is recycled in the process. Generally the nitrogen compounds therefore require an additional filtration step of the benzene through a clay or zeolitic bed to absorb them. This bed must be appropriately maintained to ensure continued efficacy in removing the nitrogen compounds.
- the present invention is a process for preparing cyclohexenyl or alkenyl aromatic compounds.
- the process includes alkylation of a cyclohexane or aromatic compound; dehydrogenation of the alkylated cyclohexane or aromatic compound to form a process stream including a cyclohexenyl or alkenyl aromatic compound; and separating the process stream into a cyclohexenyl or alkenyl aromatic compound rich fraction and a cyclohexane or aromatic compound rich fraction.
- the process also includes adding nitrogen-containing compounds at one point in the process and using water to extract the nitrogen-containing compounds, or the break down products of the nitrogen-containing compounds, from the cyclohexane or aromatic compound rich fraction at another point in the process.
- the present invention is a process for preparing styrene.
- the process includes alkylating benzene to form ethylbenzene, dehydrogenating ethylbenzene to form a process stream containing styrene, unreacted ethylbenzene, benzene and toluene products, separating the process streams into styrene, benzene and toluene fractions, and recycling the benzene fraction back into the process.
- the process also includes adding a nitrogen-containing compound at one point in the process and using water to extract the nitrogen-containing compounds, or the break down products of the nitrogen-containing compounds, from the benzene fraction at another point in the process.
- the present invention is, in a process for preparing cyclohexenyl or alkenyl aromatic compounds, wherein the process includes an alkylation of a cyclohexane or aromatic compound; a dehydrogenation of the alkylated cyclohexane or aromatic compound to form a process stream; and a separation of the process stream into a cyclohexenyl or alkenyl aromatic compound rich component and a cyclohexane or aromatic compound rich component; and the process also includes the use of nitrogen-containing compounds, an improvement of using water to extract the nitrogen-containing compounds from the cyclohexane or aromatic compound rich component.
- the present invention is useful in a process for preparing cyclohexenyl and alkenyl aromatic compounds, such as styrene, that include alkylation of benzene to form ethylbenzene, followed by dehydrogenation of ethylbenzene to form a process stream containing styrene, benzene and toluene products, which are then separated into styrene, unreacted ethylbenzene, benzene and toluene fractions, and the benzene fraction is recycled. Nitrogen compounds are employed to prevent homopolymerization of the styrene product.
- Amine compounds are also injected into the process to neutralize carbonic acid in the water phase of the process.
- the invention provides an improvement comprising intimately contacting the benzene fraction with water and then removing the water containing nitrogen compounds from the benzene fraction prior to alkylation of the recycled benzene fraction.
- the present invention thus includes many possible embodiments, since the water can be injected at more than one possible point during the process, and can likewise be removed at more than one point, and via more than one means.
- the water is injected with the fresh benzene prior to alkylation, which is also prior to the entry of the recycled benzene; the fresh and recycled benzenes are thoroughly mixed; and then they are passed through a drying column which removes the water and the entrained nitrogen compounds and passes the now-dry benzene on to the alkylation unit.
- styrene is continuously mass produced in a dehydrogenation process of ethylbenzene in any type of reactor conventionally employed for a continuous mass styrene production process.
- a reactor is charged with ethylbenzene under dehydrogenation conditions and a styrene-, unreacted ethylbenzene-, benzene- and toluene-containing process stream is formed.
- Neutralizing amines such as morpholine as added to the stream to increase the pH of the co-existing water phase.
- Stabilizing compounds that contain nitrogen, such as 2,6-dinitro-p-cresol, 4-tert-butylcatechol, 7-substituted quinone methides, phenyldiamine, 2,6-dinitro-p-cresol, N,N-bis(hydroxypropyl)hydroxylamine, and other amine compounds, may then be added to the organic phase of the process stream to prevent homopolymerization of the styrene and then the process stream passes to a separation unit where the three products are separated into fractions and removed, with the stabilizing compounds retained primarily with the tar fraction.
- nitrogen such as 2,6-dinitro-p-cresol, 4-tert-butylcatechol, 7-substituted quinone methides, phenyldiamine, 2,6-dinitro-p-cresol, N,N-bis(hydroxypropyl)hydroxylamine, and other amine compounds
- the benzene fraction can include nitrogen compounds and/or their breakdown products. It can therefore be desirable to treat the benzene fraction in some way to remove the nitrogen compounds prior to recycling the benzene fraction back into the process. Such treatment may include passing through an absorbent bed that includes as the absorbent material at least one adsorbent such as a zeolite, activated carbon, clay, alumina, and the like. Other possible treatments include further distillation, fractionation, or additional separation steps. Following removal of the nitrogen compounds, the benzene fraction is ready for recycle to the alkylation phase of the process, where it is to be first mixed with fresh benzene or added directly to the process as a separate stream.
- adsorbent such as a zeolite, activated carbon, clay, alumina, and the like.
- Other possible treatments include further distillation, fractionation, or additional separation steps.
- the method of the present invention finds particular use in commercial systems where economics represent a driving factor. It has been found that when the benzene containing the nitrogen compounds is intimately mixed with water, the major portion of the nitrogen compounds preferentially entrain with the water, and therefore can be easily removed simply by removing the water. Thus, the need for use of an absorbent bed is greatly minimized, thus reducing maintenance and replacement requirements, and addition of water is a relatively negligible cost. This combination makes application of the present invention highly desirable in commercial styrene production at most of the world's styrene production facilities.
- water can be injected at a point in the process that is shortly after the separation of the dehydrogenation product fractions, styrene, toluene and benzene in the case of styrene production.
- the water will achieve an intimate mixing with the benzene fraction.
- the water, containing the now-entrained nitrogen compounds is then removed via, for example, use of a simple separation unit designed to remove water based upon differentiation of density; a distillation unit; conventional stripping or other drying means; and the like.
- the “cleaned” benzene can then be routed to the alkylation unit where it can be, optionally, mixed with fresh benzene, and then converted into more ethylbenzene.
- the nitrogen-containing benzene that has been separated from the styrene and toluene is refluxed directly for mixing with the fresh benzene, and water is added at the same point.
- the nitrogen compounds quickly and preferentially transport into the water phase.
- the benzene/water process stream can be passed through a distillation unit, drying column, fixed adsorbent bed, or other means to remove the water and, therefore, the nitrogen compounds.
- the proportion of water can be important in some embodiments of the present invention, particularly where the levels of nitrogen compounds are comparatively high. Desirably the water is employed in an amount that is sufficient to optimize entrainment of the undesirable nitrogen compounds, but not of such an excess that removal of the water becomes unnecessarily problematic. In one embodiment a proportion of water ranging from about 1 percent to about 10 percent, based on weight of benzene, is employed, which is equivalent to from about 10,000 ppm water to about 30,000 ppm of water in benzene. In another embodiment the proportion of water ranges from about 2 percent to about 4 percent, based on weight of benzene. Most consistent performance is generally found when the water is deionized water, boiler feed water, or steam condensate which reduces potentially adverse side reactions accruing from the presence of even very low amounts of conventional water treatment compounds.
- the intimate contact is maintained for at least about 1 minute. In another embodiment the intimate contact is maintained for at least about 5 minutes. Generally, longer times promote increased nitrogen compound removal, with the goal being to remove at least about 90 percent of such compounds.
- the benefits of the present invention include, in particular, the need for less frequent regeneration of the alkylation catalyst or catalysts, and also less frequent change-out of the absorbent beds currently used to remove most of the nitrogen compounds from the benzene fraction prior to recycle. While it may still be desirable to employ such beds with the present invention, they will thus require significantly less maintenance, and the amount of nitrogen compounds that do ultimately reach the alkylation catalyst in the recycled benzene will be greatly minimized in comparison with recycled benzene which has not been subjected to the practice of the present invention.
- the equilibrium concentration of nitrogen compounds in water in contact with a benzene fraction that has been separated from a stabilized styrene-, benzene-, and toluene-containing process stream is determined using a gas chromatography method utilizing the ANTEK 7090 SCD/NCLD with automated gas and/or liquid sampling valves.
- the ANTEK 7090 SCD/NCLD is available from ANTEK Instruments L.P.
- the equilibrium concentration is determined to be 18.0 ppm.
- Water is injected at two different rates, 0.1 gal/min [0.3785 l/min] and 0.2 gal/min [0.7516 l/min], into a flow line containing the benzene fraction process stream and then recovered and analyzed using the same method of above.
- the nitrogen concentration of the sample taking during the 0.1 gal/min water injection is 17.0 ppm.
- the nitrogen concentration of the sample taking during the 0.2 gal/min water injection is 19.0 ppm.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/685,633 US20050085677A1 (en) | 2003-10-15 | 2003-10-15 | Method for improved production of cyclohexenyl and alkenyl aromatic compounds |
EP04784337A EP1727860A4 (en) | 2003-10-15 | 2004-09-17 | PROCESS FOR THE IMPROVED PRODUCTION OF CYCLOHEXENYL AND ALKENYL AROMATIC COMPOUNDS |
CNB2004800303920A CN100486943C (zh) | 2003-10-15 | 2004-09-17 | 环己烯基和链烯基芳族化合物的改进的生产方法 |
JP2006535500A JP4654192B2 (ja) | 2003-10-15 | 2004-09-17 | シクロヘキセニルおよびアルケニル芳香族化合物の改良された製造法 |
BRPI0415377-4A BRPI0415377A (pt) | 2003-10-15 | 2004-09-17 | método para melhoria da produção de compostos aromáticos de ciclohexenila ou alquenila |
PCT/US2004/030447 WO2005040266A2 (en) | 2003-10-15 | 2004-09-17 | Method for improved production of cyclohexenyl and alkenyl aromatic compounds |
CA002542187A CA2542187A1 (en) | 2003-10-15 | 2004-09-17 | Method for improved production of cyclohexenyl and alkenyl aromatic compounds |
KR1020067007238A KR20070029112A (ko) | 2003-10-15 | 2004-09-17 | 사이클로헥세닐 및 알케닐 방향족 화합물의 개선된 생산방법 |
TW093129074A TW200526545A (en) | 2003-10-15 | 2004-09-24 | Method for improved production of cyclohexenyl and alkenyl aromatic compounds |
US11/412,244 US7569741B2 (en) | 2003-10-15 | 2006-04-26 | Petrochemical feedstock purification |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/685,633 US20050085677A1 (en) | 2003-10-15 | 2003-10-15 | Method for improved production of cyclohexenyl and alkenyl aromatic compounds |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/412,244 Continuation-In-Part US7569741B2 (en) | 2003-10-15 | 2006-04-26 | Petrochemical feedstock purification |
Publications (1)
Publication Number | Publication Date |
---|---|
US20050085677A1 true US20050085677A1 (en) | 2005-04-21 |
Family
ID=34520646
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/685,633 Abandoned US20050085677A1 (en) | 2003-10-15 | 2003-10-15 | Method for improved production of cyclohexenyl and alkenyl aromatic compounds |
US11/412,244 Expired - Fee Related US7569741B2 (en) | 2003-10-15 | 2006-04-26 | Petrochemical feedstock purification |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/412,244 Expired - Fee Related US7569741B2 (en) | 2003-10-15 | 2006-04-26 | Petrochemical feedstock purification |
Country Status (9)
Country | Link |
---|---|
US (2) | US20050085677A1 (ja) |
EP (1) | EP1727860A4 (ja) |
JP (1) | JP4654192B2 (ja) |
KR (1) | KR20070029112A (ja) |
CN (1) | CN100486943C (ja) |
BR (1) | BRPI0415377A (ja) |
CA (1) | CA2542187A1 (ja) |
TW (1) | TW200526545A (ja) |
WO (1) | WO2005040266A2 (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2110368A1 (en) | 2008-04-18 | 2009-10-21 | Total Petrochemicals France | Alkylation of aromatic substrates and transalkylation process |
CN101914179B (zh) * | 2010-07-30 | 2012-01-25 | 宁波镇洋化工发展有限公司 | 芳香烃-不饱和腈-n-取代马来酰亚胺-环烯烃耐热共聚物的制备方法 |
CN101914178B (zh) * | 2010-07-30 | 2012-05-16 | 宁波镇洋化工发展有限公司 | 芳香烃-不饱和腈-环烯烃耐热共聚物的制备方法 |
WO2014082838A1 (en) | 2012-11-29 | 2014-06-05 | Exxonmobil Chemical Patents Inc. | Processes for treating olefin feedstreams and related oligomerization processes |
Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4003800A (en) * | 1976-01-02 | 1977-01-18 | Gulf Research & Development Company | Styrene purification process |
US4009217A (en) * | 1975-05-06 | 1977-02-22 | Universal Oil Products Company | Process for production and dehydrogenation of ethylbenzene |
US4104318A (en) * | 1977-05-27 | 1978-08-01 | Gulf Research & Development Company | Process for removing organic oxygen-containing impurities from an organic composition in the presence of steam |
US4165441A (en) * | 1977-06-06 | 1979-08-21 | Mitsubishi Chemical Industries, Ltd. | Process for the preparation of styrene |
US4250344A (en) * | 1978-10-25 | 1981-02-10 | Chem Systems Inc. | Cracking process for styrene |
US4287375A (en) * | 1979-03-13 | 1981-09-01 | Metallgesellschaft Aktiengesellschaft | Process of converting ethylbenzene to styrene by catalytic dehydrogenation |
US4319066A (en) * | 1980-08-01 | 1982-03-09 | The Standard Oil Company | Preparation of alkenyl aromatic compounds |
US5994606A (en) * | 1995-03-08 | 1999-11-30 | Mitsubishi Chemical Corporation | Method for dehydrogenation of hydrocarbon |
US6395946B1 (en) * | 1998-02-18 | 2002-05-28 | Shell Oil Company | Process for the preparation of styrenes |
US6420621B2 (en) * | 1997-10-20 | 2002-07-16 | China Petro-Chemical Corp. | Optimized process for the preparation of olefins by direct conversion of multiple hydrocarbons |
US6437207B1 (en) * | 1998-05-11 | 2002-08-20 | Shell Oil Company | Process for the preparation of styrenes |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS53103428A (en) * | 1977-02-21 | 1978-09-08 | Uop Inc | Method of dehydrogenating alkyl aromatic hydrocarbon |
JPS63230659A (ja) * | 1987-03-19 | 1988-09-27 | Nippon Steel Chem Co Ltd | 重合防止剤の回収方法 |
JPH05117178A (ja) * | 1991-08-21 | 1993-05-14 | Nippon Steel Chem Co Ltd | スチレンの製造方法 |
WO2002031085A2 (en) * | 2000-10-09 | 2002-04-18 | Sasol Technology (Pty) Ltd. | Separation of oxygenates from a hydrocarbon stream |
US6768035B2 (en) * | 2002-01-31 | 2004-07-27 | Chevron U.S.A. Inc. | Manufacture of high octane alkylate |
US6743962B2 (en) * | 2002-01-31 | 2004-06-01 | Chevron U.S.A. Inc. | Preparation of high octane alkylate from Fischer-Tropsch olefins |
-
2003
- 2003-10-15 US US10/685,633 patent/US20050085677A1/en not_active Abandoned
-
2004
- 2004-09-17 KR KR1020067007238A patent/KR20070029112A/ko not_active Application Discontinuation
- 2004-09-17 BR BRPI0415377-4A patent/BRPI0415377A/pt not_active IP Right Cessation
- 2004-09-17 CA CA002542187A patent/CA2542187A1/en not_active Abandoned
- 2004-09-17 CN CNB2004800303920A patent/CN100486943C/zh not_active Expired - Fee Related
- 2004-09-17 EP EP04784337A patent/EP1727860A4/en not_active Withdrawn
- 2004-09-17 WO PCT/US2004/030447 patent/WO2005040266A2/en active Application Filing
- 2004-09-17 JP JP2006535500A patent/JP4654192B2/ja not_active Expired - Fee Related
- 2004-09-24 TW TW093129074A patent/TW200526545A/zh unknown
-
2006
- 2006-04-26 US US11/412,244 patent/US7569741B2/en not_active Expired - Fee Related
Patent Citations (11)
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 |
US4003800A (en) * | 1976-01-02 | 1977-01-18 | Gulf Research & Development Company | Styrene purification process |
US4104318A (en) * | 1977-05-27 | 1978-08-01 | Gulf Research & Development Company | Process for removing organic oxygen-containing impurities from an organic composition in the presence of steam |
US4165441A (en) * | 1977-06-06 | 1979-08-21 | Mitsubishi Chemical Industries, Ltd. | Process for the preparation of styrene |
US4250344A (en) * | 1978-10-25 | 1981-02-10 | Chem Systems Inc. | Cracking process for styrene |
US4287375A (en) * | 1979-03-13 | 1981-09-01 | Metallgesellschaft Aktiengesellschaft | Process of converting ethylbenzene to styrene by catalytic dehydrogenation |
US4319066A (en) * | 1980-08-01 | 1982-03-09 | The Standard Oil Company | Preparation of alkenyl aromatic compounds |
US5994606A (en) * | 1995-03-08 | 1999-11-30 | Mitsubishi Chemical Corporation | Method for dehydrogenation of hydrocarbon |
US6420621B2 (en) * | 1997-10-20 | 2002-07-16 | China Petro-Chemical Corp. | Optimized process for the preparation of olefins by direct conversion of multiple hydrocarbons |
US6395946B1 (en) * | 1998-02-18 | 2002-05-28 | Shell Oil Company | Process for the preparation of styrenes |
US6437207B1 (en) * | 1998-05-11 | 2002-08-20 | Shell Oil Company | Process for the preparation of styrenes |
Also Published As
Publication number | Publication date |
---|---|
CA2542187A1 (en) | 2005-05-06 |
WO2005040266A3 (en) | 2007-02-22 |
CN1997612A (zh) | 2007-07-11 |
EP1727860A2 (en) | 2006-12-06 |
CN100486943C (zh) | 2009-05-13 |
WO2005040266A2 (en) | 2005-05-06 |
US20060194993A1 (en) | 2006-08-31 |
KR20070029112A (ko) | 2007-03-13 |
JP4654192B2 (ja) | 2011-03-16 |
JP2007516958A (ja) | 2007-06-28 |
BRPI0415377A (pt) | 2006-12-12 |
US7569741B2 (en) | 2009-08-04 |
TW200526545A (en) | 2005-08-16 |
EP1727860A4 (en) | 2010-03-24 |
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Legal Events
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AS | Assignment |
Owner name: FINA TECHNOLOGY INC, TEXAS Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:BUTLER, JAMES R.;MERRILL, JAMES;REEL/FRAME:014611/0540 Effective date: 20030930 |
|
STCB | Information on status: application discontinuation |
Free format text: EXPRESSLY ABANDONED -- DURING EXAMINATION |