EP0440637A1 - Procede ameliore de transalkylation de polyalkylbenzenes - Google Patents

Procede ameliore de transalkylation de polyalkylbenzenes

Info

Publication number
EP0440637A1
EP0440637A1 EP89906584A EP89906584A EP0440637A1 EP 0440637 A1 EP0440637 A1 EP 0440637A1 EP 89906584 A EP89906584 A EP 89906584A EP 89906584 A EP89906584 A EP 89906584A EP 0440637 A1 EP0440637 A1 EP 0440637A1
Authority
EP
European Patent Office
Prior art keywords
benzene
polyalkylbenzenes
transalkylation
feed
catalyst
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.)
Withdrawn
Application number
EP89906584A
Other languages
German (de)
English (en)
Inventor
George Dan Suciu
Joon Taek Kwon
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lummus Technology LLC
Original Assignee
Lummus Crest Inc
ABB Lummus Crest Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Lummus Crest Inc, ABB Lummus Crest Inc filed Critical Lummus Crest Inc
Publication of EP0440637A1 publication Critical patent/EP0440637A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
    • C07C6/08—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond
    • C07C6/12—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring
    • C07C6/126—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring of more than one hydrocarbon
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
    • C07C6/08—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond
    • C07C6/12—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing 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

Definitions

  • This invention relates to a process for the conversion of a feed comprising polyalkylbenzenes, preferably of a feed comprising benzene and polyalkylbenzenes, in a transalkylation reactor to monoalkylbenzenes in the presence of a catalyst. More particularly, this invention relates to an improved process for the conversion of a feed comprising benzene and polyalkylbenzenes to monoalkylbenzenes wherein said improved conversion is accomplished using a feed having a low benzene to alkyl groups ratio.
  • U.S. Patent No. 4,169,111 discloses transalkylation of polyalkylbenzenes in a fixed bed of an acidic zeolite catalyst.
  • the ratio of benzene to diethylbenzene which is fed to the reactor is approximately 100:1.
  • the catalyst is able to maintain its activity for a long period of time.
  • Applicants' invention relates to an improvement in a process for the transalkylation of a feed comprising at least one polyalkylbenzene in a reactor in the presence of a transalkylation catalyst to produce at least one monoalkylbenzene.
  • the improvement comprises transalkylating said at least one polyalkylbenzene in the presence of hydrogen gas.
  • the said at least one polyalkylbenzene may comprise diisopropylbenzene and/or triisopropylbenzene, or polyethylbenzene.
  • the feed further comprises benzene.
  • the said at least one monoalkylbenzene may be cumene or ethylbenzene.
  • the transalkylation catalyst preferably is a zeolite catalyst.
  • the hydrogen gas may be introduced to the reactor at a molar ratio of hydrogen to alkyl groups of from about 1:10 to about 1:1, preferably at about 1:3.
  • the transalkylation may be performed in either the liquid, vapor, or mixed phases.
  • the alkyl groups contained in each side chain alkyl group of the polyalkylbenzenes have from 1 to 12 carbon atoms.
  • the process of the present invention has the advantage of longer catalyst life with the need for less frequent regenerations, and higher weight hourly space velocities (WHSV's) for a given catalytic conversion.
  • Weight hourly space velocity is defined as the weight of liquid feed passed per hour per unit weight of the catalyst bed. The units are 1/hours (h ⁇ ) .
  • the feed to the transalkylation reactor comprises benzene and at least one polyalkylbenzene
  • the molar ratio of benzene rings to alkyl groups in the feed can be reduced for example to about 8:1, without decreasing the life of the catalyst.
  • the molar ratio of benzene rings to alkyl groups may be from about 4:1 to about 20:1, more preferably from about 6:1 to about 10:1.
  • the drawing is a schematic of an embodiment of a transalkylation process in accordance with the present invention.
  • benzene and an olefin are fed to alkylator 10 through line 12.
  • the olefin is passed through line 13 to line 12 where it is combined with benzene.
  • the olefin and the benzene are reacted in alkylator 10, which has two stages 14 and 15, to form a product comprising at least one monoalkylbenzene.
  • each stage 14 and 15 is a bed of zeolite catalyst.
  • alkylator 10 may contain any number of stages and the catalyst beds may be either fixed beds or moving beds.
  • the olefin which is fed to alkylator 10 may be any olefin. Specific examples of olefins which may be used include ethylene and propylene, which may be reacted with benzene in alkylator 10 to produce a desired ethylbenzene or cumene product, respectively.
  • Catalytic conversion conditions for alkylation of benzene with olefin in stages 14 and 15 of alkylator 10 may be carried out at an outlet temperature of from about 150° to about 900°F, preferably from about 200° to about 550°F, at a pressure of from about 150 psig to about 2,000 psig, preferably from about 250 psig to about 1,000 psig, and at a total LHSV from about 2 to about 1,000 preferably from about 4 to about 100 h ⁇ .
  • benzene column 20 benzene is distilled off through line 22, whereas a bottoms fraction is withdrawn through line 24, and passed to monoalkylbenzene column 28.
  • a portion of the benzene in line 22 is diverted from line 22 to line 38, and passed to transalkylator 42.
  • the remaining benzene in line 22 is passed to line 11 as recycle benzene which is passed to line 12, whereby a mixture of fresh and recycle benzene may be passed, along with olefin to alkylator 10.
  • the recycle benzene may be purified of light and heavy ends before re-entering alkylator 10.
  • a monoalkylbenzene distillate is distilled off through line 29 from monoalkylbenzene column 28.
  • the monoalkylbenzene distillate may consist of ethylbenzene, cumene, or any other monoalkylbenzene distillate product depending upon the olefin which is fed to alkylator 10.
  • a bottoms fraction is withdrawn from monoalkylbenzene column 28 through line 30 and enters polyalkylbenzene column 34.
  • polyalkylbenzene column 34 polyalkylbenzenes are distilled off and withdrawn through line 35.
  • the polyalkylbenzene distillate may, for example, be polyethylbenzenes, diisopropylbenzene, triisopropylbenzene, or a mixture of diisopropylbenzene and triisopropylbenzene.
  • the polyalkylbenzenes distilled off depend upon the olefin which is reacted in the alkylator 10.
  • Heavy ends are withdrawn through line 39.
  • the heavy ends may comprise, for example, one or more diphenylalkanes, which if desired may be processed further.
  • the polyalkylbenzenes in line 35 are passed to line 38, whereby the polyalkylbenzenes are combined with benzene in line 38, and the mixture of benzene and polyalkylbenzenes is passed through line 40 to transalkylator 42.
  • a stream of hydrogen gas from line 41 is passed into line 38 in order to be co-fed with the mixture of benzene and polyalkylbenzenes being introduced into transalkylator 42.
  • the hydrogen gas may be passed from line 41 directly to transalkylator 42, wherein the hydrogen gas is co-fed into transalkylator 42 with the mixture of benzene and polyalkylbenzenes being introduced from line 38.
  • the hydrogen gas is co-fed with the mixture of benzene and polyalkylbenzenes into transalkylator 42 at a molar ratio of hydrogen to alkyl groups of from about 1:10 to about 1:1, preferably at .about 1:3.
  • the molar ratio of benzene to alkyl groups in the feed is from about 4:1 to about 20:1, preferably from about 6:1 to about 10:1.
  • the addition of hydrogen gas to the mixture of benzene and polyalkylbenzenes enables one to use a feed of benzene and polyalkylbenzenes having a lower benzene to alkyl groups ratio, to use a smaller transalkylation reactor and recovery system, and to maintain a longer catalyst life with fewer regenerations of the catalyst.
  • transalkylator 42 the mixture of benzene and polyalkylbenzenes are reacted in the presence of a catalyst, preferably a zeolite catalyst, to form a product comprising monoalkylbenzenes.
  • the catalyst bed may be a fixed bed or a moving bed.
  • Transalkylation conditions may be at a temperature of from about 150°F to about 900°F, preferably from about 300°F to about 550 F, at a pressure of from about 150 to about 2,000 psig, preferably from about 250 psig of about 1,000 psig and at a total WHSV of from about 1 to 1,000 preferably from about 2 to about 100.
  • the transalkylation may take place in either the liquid, vapor, or mixed phases.
  • the monoalkylbenzenes produced by the transalkylation reaction depend upon the polyalkylbenzenes which are fed to transalkylator 42.
  • cumene may be the monoalkylbenzene product.
  • polyethylbenzenes are fed to transalkylator 42, ethylbenzene is the monoalkylbenzene product.
  • the alkyl groups of the polyalkylbenzenes fed to transalkylator 42 have from 1 to 12 carbon atoms.
  • the feed to transalkylator 42 does not have to consist exclusively of benzenes distilled off from benzene column 20, polyalkylbenzenes distilled off from polyalkylbenzene column 34, and hydrogen gas.
  • the feed may also include other aromatic and aliphatic compounds from other sources.
  • heavy ends such as diphenylalkanes, withdrawn from polyalkylbenzene column 34 through line 39, may be sent to a diphenylalkane converter (not shown) to produce benzene and/or lighter aromatics.
  • diphenylalkane converter not shown
  • These products may be combined with the benzene distilled off from benzene column 20 and the polyalkylbenzenes distilled off from polyalkylbenzene column 34, as well as the hydrogen gas, and introduced into transalkylator 42.
  • the effluent which contains a monoalkylbenzene product
  • the effluent is withdrawn through line 43, and may be passed to benzene column 20 for further distillation, wherein the monoalkylbenzene product will eventually be withdrawn from monoalkylbenzene column 28 through line 29.
  • the transalkylation process of the present invention is not to be limited to the distillation apparatus shown in the drawing.
  • fresh benzene and fresh polyalkylbenzenes may be co-fed with hydrogen gas directly to a transalkylator, with effluent being processed for recovery of monoalkylbenzenes.
  • a feed of polyalkylbenzenes may be fed to what is known as an "integral" transalkylator, wherein the feed of polyalkylbenzenes are co-fed to the transalkylator with an effluent from an alkylation reactor which may comprise benzene, monoalkylbenzene, and polyalkylbenzenes.
  • an alkylation reactor which may comprise benzene, monoalkylbenzene, and polyalkylbenzenes.
  • a stream of hydrogen gas may be co-fed with the polyalkylbenzenes and the effluent from the alkylation reactor to "integral" transalkylator in the same manner as in the alkylation-distillation-transalkylation apparatus shown in the drawing.
  • This example describes a transalkylation process outside the scope of the present invention.
  • a mixture of diisopropylbenzene and benzene consisting of 88.9% benzene, 0.6% cumene, 10.3% of diisopropylbenzene (DIPB) isomers, 0.2% of triisopropylbenzenes (TIPB) and small amounts of other aromatic and aliphatic compounds was passed through a transalkylation reactor having an internal diameter of 1/2 inch, and containing a zeolite catalyst at a WHSV of 4 hr ⁇ , and a pressure of 500 psig.
  • the feed has an overall molar ratio of benzene rings to propyl groups, B/P, of 8.9.
  • the catalyst activity measured by the conversion of DIPB is given as a function of time on stream since the start of the test.
  • This example describes a transalkylation process in accordance with the present invention.
  • the transalkylation reactor described in Example 1 was fed with a mixture of 11% p-diisopropylbenzene in benzene, which has a molar ratio of benzene to isopropyl groups of 8.9. Concomitantly with this liquid feed, a stream of hydrogen gas was introduced in order to achieve a molar ratio of hydrogen to isopropyl groups of 1:3.
  • Table 2 The results of the transalkylation reaction are listed in Table 2 below.
  • the balance of the effluent composition is benzene. Conversion of DIPB's and the selectivity of cumene are calculated on the basis of the isopropyl groups which reacted among benzene rings.
  • Example 2 show that the process of the present invention gives improved conversion of polyalkylbenzenes to monoalkylbenzenes and increased catalyst life.

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)
  • Polyesters Or Polycarbonates (AREA)

Abstract

Procédé amélioré de transalkylation de polyalkylbenzènes en monoalkylbenzènes dans un réacteur, en présence d'un catalyseur. L'amélioration réside dans la transalkylation d'une charge comprenant des polyalkylbenzènes, de préférence du benzène et des polyalkylbenzènes, introduite dans un réacteur de transalkylation, en présence d'hydrogène gazeux. Un tel procédé accroît la durée de vie du catalyseur et permet d'utiliser une charge, dans le réacteur de transalkylation, présentant un rapport benzène/groupes alkyle plus faible.
EP89906584A 1988-06-23 1989-05-19 Procede ameliore de transalkylation de polyalkylbenzenes Withdrawn EP0440637A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US21073788A 1988-06-23 1988-06-23
US210737 1988-06-23

Publications (1)

Publication Number Publication Date
EP0440637A1 true EP0440637A1 (fr) 1991-08-14

Family

ID=22784084

Family Applications (1)

Application Number Title Priority Date Filing Date
EP89906584A Withdrawn EP0440637A1 (fr) 1988-06-23 1989-05-19 Procede ameliore de transalkylation de polyalkylbenzenes

Country Status (6)

Country Link
EP (1) EP0440637A1 (fr)
JP (1) JPH03501975A (fr)
KR (1) KR900701699A (fr)
ES (1) ES2013683A6 (fr)
MX (1) MX171611B (fr)
WO (1) WO1989012613A1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5087783A (en) * 1988-04-27 1992-02-11 Lummus Crest, Inc. Transalkylation of benzene in a moving bed
EP0532548B1 (fr) * 1990-06-08 1994-08-10 Abb Lummus Crest Inc. Transalkylation en presence d'une boue catalytique
BE1006675A3 (fr) 1993-02-02 1994-11-16 Fina Research Procede de production d'essences a haut indice d'octane.
KR100601744B1 (ko) 1996-08-20 2006-07-19 다우 글로벌 테크놀로지스 인크. 알킬화 벤젠의 제조방법
US6462248B1 (en) * 1998-09-09 2002-10-08 Toray Industries, Inc. Method for producing aromatic compounds having alkyl group with at least three carbon atoms
US9150469B2 (en) 2009-05-18 2015-10-06 Uop Llc Aromatic alkylation process with reduced byproduct formation
BR102014002154A2 (pt) 2014-01-28 2015-10-27 Whirlpool Sa processo de produção de composto alquilaromático, processo de transalquilação de polialquilaromáticos para produção seletiva de composto monoalquilaromático, e, processo de alquilação e transalquilação de compostos aromáticos e/ou poliaromáticos
IT201900015066A1 (it) * 2019-08-27 2021-02-27 Versalis Spa Procedimento per il trattamento di idrocarburi polialchilaromatici.

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2349834A (en) * 1941-04-12 1944-05-30 Universal Oil Prod Co Treatment of hydrocarbons
US3410921A (en) * 1966-06-27 1968-11-12 Universal Oil Prod Co Transalkylation of polyalkylated aromatic compounds using a crystalline aluminosilicate catalyst
GB1292228A (en) * 1970-06-05 1972-10-11 British Petroleum Co Improvements relating to the production of cumene
JPS5915695B2 (ja) * 1977-02-24 1984-04-11 東亜燃料工業株式会社 芳香族炭化水素変換用触媒の処理方法
JPS62228031A (ja) * 1981-06-03 1987-10-06 Toray Ind Inc 芳香族炭化水素の変換方法
JPH0788315B2 (ja) * 1987-06-01 1995-09-27 出光興産株式会社 炭化水素油の製造方法
JPH0788316B2 (ja) * 1987-06-01 1995-09-27 出光興産株式会社 炭化水素油の製造法
EP0308097B1 (fr) * 1987-09-02 1992-01-29 Mobil Oil Corporation Procédé de transalkylation d'hydrocarbures(polyalkyl)aromatiques

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8912613A1 *

Also Published As

Publication number Publication date
MX171611B (es) 1993-11-09
ES2013683A6 (es) 1990-05-16
JPH03501975A (ja) 1991-05-09
KR900701699A (ko) 1990-12-04
WO1989012613A1 (fr) 1989-12-28

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