WO2014047000A1 - Fluides appauvris en naphtalène - Google Patents

Fluides appauvris en naphtalène Download PDF

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Publication number
WO2014047000A1
WO2014047000A1 PCT/US2013/059916 US2013059916W WO2014047000A1 WO 2014047000 A1 WO2014047000 A1 WO 2014047000A1 US 2013059916 W US2013059916 W US 2013059916W WO 2014047000 A1 WO2014047000 A1 WO 2014047000A1
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WO
WIPO (PCT)
Prior art keywords
naphthalene
overhead
product
tower
fractionation
Prior art date
Application number
PCT/US2013/059916
Other languages
English (en)
Inventor
Thomas A. Gribschaw
Brian W. ROBERTS
Andrew R. Witt
Original Assignee
Exxonmobil Chemical Patents 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 Exxonmobil Chemical Patents Inc. filed Critical Exxonmobil Chemical Patents Inc.
Priority to US14/405,710 priority Critical patent/US20150183696A1/en
Publication of WO2014047000A1 publication Critical patent/WO2014047000A1/fr

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00Purification; Separation; Use of additives
    • C07C7/04Purification; Separation; Use of additives by distillation
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01DSEPARATION
    • B01D3/00Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/14Fractional distillation or use of a fractionation or rectification column
    • B01D3/143Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00Purification; Separation; Use of additives
    • C07C7/005Processes comprising at least two steps in series
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00002Chemical plants
    • B01J2219/00004Scale aspects
    • B01J2219/00006Large-scale industrial plants

Definitions

  • the invention relates to the production of naphthalene-depleted heavy aromatics, the naphthalene-depleted heavy aromatic product made thereby, and to an apparatus adapted for said production.
  • FIG. 1 is a schematic illustrating conventional production of useful fluids, including naphthalene- depleted fluids, from reformate.
  • topped reformate 1 is introduce into the first tower 2, and by progression through a second tower 5, third tower 8, and fourth tower 11, fluidly connected through conduits 4, 7, and 10, respectively, leading to recovering naphthalene as an overhead stream 9 and useful products such as 3 Aromatic 100 Fluid (CAS Registry No.
  • Aromatic 150 ND Fluid (CAS Registry No. 70693-06-0; distillation range of 184-195°C; Flash Point 65°C; 99.7 wt% aromatics), naphthalene, 12 Aromatic 200 ND Fluid (CAS Registry No. 68477-31-6; distillation range of 235-278°C; 106°C; 99.5 wt% aromatics), and heavy byproduct 13.
  • the distillation range is taken from the initial boiling point (IBP) to dry point (DP), terms defined further hereinbelow.
  • Aromatic 100 Fluid, Aromatic 150 ND Fluid, Aromatic 200 ND Fluid are all well-known fluids available from ExxonMobil Chemical Company, Baytown, TX, USA and/or Sarnia, Canada.
  • the designation "ND” indicates naphthalene-depleted and, as used herein, the designation "ND” and the term “naphthalene-depleted” means a fluid having less than 1.0 wt% naphthalene content based on the total weight of the fluid.
  • Topped reformate is reformate having BTX - benzene, toluene, and xylene - removed.
  • IBP Initial Boiling Point
  • DP Dry Point
  • Solutions offered by the prior art include introduction of a diluent with the feed or in the tower overhead system resulting in energy inefficiencies and/or the warming cooling medium to assure temperatures are maintained above the freezing point.
  • Specific examples of fractionation processes involving naphthalene include the following.
  • U.S. Patent No. 3, 193,952 teaches a method of making naphthalene wherein, in an embodiment, the product naphthalene is taken as a bottoms product but the overheads are recycled to extinction.
  • CN 1 112539A discloses a three tower batch rectification for the production of isopropyl naphthalene.
  • Tower I is used for dewatering and removal of naphthalene and monoisopropyl naphthalene.
  • Tower II is for producing tri-isopropyl naphthalene and the tower III for producing fine di-isopropyl naphthalene.
  • JP 62167736A teaches naphthalene preparation from cracking gas, comprising (1) removing naphthalene-rich fraction as side-cut from gasoline fractionating tower, and (2) separating naphthalene from side-cut.
  • GB 2299342A teaches a process for efficiently controlling the bottom temperature of a primary fractionator column, particularly for the purpose of avoiding blocking by crystallization of diaromatics and more particularly naphthalene, comprising: (a) withdrawing at least one oil fraction stream from the primary fractionator column and cooling; (b) separating remaining liquid and precipitate; and (c) returning remaining liquid to fractionator.
  • JP 60013723A teaches that crude naphthalene oil is introduced in a column where it is subjected to atmospheric distillation; the bottom liquid is removed as a heavy oil, and vapour of the overhead fraction is fed via a partial condensation reboiler to a light oil separating column, where it is distilled under reduced pressure, and a light oil is recovered from the column top while naphthalene is recovered from the column bottom.
  • the partial condensation reboiler condenses at least part of the overhead fraction from the heavy oil separating column so that the obtained heat may be used as a heat source for the light oil separating column.
  • the residual constituent obtained when the vapour is partially condensed is fed to the light oil separating column.
  • naphthalene from a mixture comprising naphthalene and alkylbenzenes is disclosed in US 7, 189,887.
  • the process described therein comprises: feeding a stream containing naphthalene and alkylbenzenes to a distillation column reactor containing a bed of trans alky lation catalyst and contacting the naphthalene with the alkylbenzenes in the presence of the alkylation catalyst and separating the unreacted alkylbenzenes from the unreacted naphthalene and alkyl naphthalene by fractional distillation.
  • Naphthalene is said to accumulate in the reaction zone until it is converted to alky lnaphthalenes .
  • naphthalene is prepared from petroleum fractions by blending the reformate feedstock with the effluent from the hydrodealkylation reactor in the presence of a catalyst. The resulting mixture is separated into 4 fractions, the lightest being gasoline. Naphthalene is separated from the second lightest cut by fractional crystallization and the other liquor recirculated to a hydrodealkylation zone. The third fraction is also recirculated to the hydrodealkylation zone. A fourth fraction is used for fuel oil.
  • JP 1 198687A teaches recovering light oils and naphthalene, in a method comprising distilling an oil having absorbed the light oils and naphthalene from coke oven gas, in a tower containing a reboiler in the bottom.
  • JP 60067438A teaches a method involving: (a) directly introducing benzene- containing oil to a benzene removing tower without dehydration; (b) steam stripping with steam from the bottom while dehydrating; (c) refluxing the fraction from the middle stage of the benzene removing tower and recovering crude benzene from the top and crude naphthalene from the middle stage of the tower.
  • the dehydrating tower used in known processes is not required.
  • JP 60013723 teaches separating crude naphthalene into a naphthalene product having a purity of at least 95 wt% and a light oil product.
  • the invention is directed to a method of providing naphthalene-depleted aromatic product, and to an apparatus adapted therefor.
  • Fractionation towers and fluid connections are configured to provide a system that ultimately takes off naphthalene as a bottom stream, where it can be assured to be above its freezing point (80°C for pure naphthalene), and at least one, and preferably plural naphthalene-depleted aromatic fluids are also taken off as products. Taking naphthalene off as a bottoms product also ensures a higher level of impurities, thereby depressing the freezing point and making it easier to avoid freezing of the bottoms product in the lines.
  • Figure 1 is a prior art configuration of plural towers to provide naphthalene- depleted solvents.
  • Figure 2 is an embodiment of an apparatus according to the present invention, and adapted for the process of according to the present invention, to produce the product according to the present invention.
  • towers and fluid connections associated therewith are arranged so that naphthalene is taken off as a bottoms product and at least one and preferably plural naphthalene-depleted aromatic fluids are also taken off.
  • taken off and taking off it is meant that at least a portion of the identified product(s) is/are removed from the system.
  • the naphthalene product taken off is typically less than 90 wt% napththalene, such as from 25-85 wt% or 30-70 wt% or 40-60 wt%, with ranges from any lower amount listed to any higher amount listed also being contemplated, e.g., 30-60 wt%. While higher purity naphthalene may be recovered by further processing out of the system shown in Figure 2, below, conventionally the naphthalene recovered from this system is used as fuel.
  • FIG. 2 is a schematic of a process according to the present invention, and an apparatus adapted therefor. It will be appreciated that the process and apparatus therefor may be practiced other than as specifically recited in the following specific example. Various valves, heat exchangers, and other details of such an apparatus are not shown for convenience of view, but would be apparent to one of ordinary skill in the art in possession of the present disclosure.
  • topped reformate 101 is provided to a fractionation tower 102 and a light aromatic hydrocarbon such as Aromatic 100 Fluid is taken off as overheads 103.
  • the bottoms product 104 is passed to a second fractionation tower 105 and an overhead 106 is passed to a third fractionation tower 108. which in turns provides a naphthalene-depleted fluid taken off as overhead 109, such as Aromatic 150 ND Fluid, and naphthalene is taken off as a bottoms product 110; this is a highly advantageous aspect of the invention.
  • the bottoms product 107 of fractionation tower 105 is passed to a fourth tower 111 to be separated into a heavy bottoms product 113 and an overhead 112, such as Aromatic 200 ND Fluid.
  • tower 105 typically will be under a couple of pounds of pressure, such as from 1-6 psig (gauge pressure), or in embodiments, 3-6 psig (corresponding to about 0.0069 - 0.0414 Mpa-gauge, and 0.021 to 0.0414 Mpa-gauge, respectively).
  • the temperature regime of tower 105 in advantageous embodiments, will range from 370 to 525°F (188 - 274C°) from the bottom of the tower to the top of the tower.
  • conduit 106 may pass through a cooler and the overhead split, with a portion continuing on to tower 108 and a portion being recycled to tower 105. and likewise conduit 107 may pass through a heater, with a portion of the bottoms product continuing on to tower 111 and a portion being recycled to tower 105.

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  • 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)

Abstract

L'invention concerne la production d'aromatiques lourds appauvris en naphtalène, le produit d'aromatiques lourds appauvris en naphtalène préparé ainsi et un appareil conçu pour ladite production.
PCT/US2013/059916 2012-09-20 2013-09-16 Fluides appauvris en naphtalène WO2014047000A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US14/405,710 US20150183696A1 (en) 2012-09-20 2013-09-16 Naphthalene-Depleted Fluids

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201261703300P 2012-09-20 2012-09-20
US61/703,300 2012-09-20

Publications (1)

Publication Number Publication Date
WO2014047000A1 true WO2014047000A1 (fr) 2014-03-27

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2013/059916 WO2014047000A1 (fr) 2012-09-20 2013-09-16 Fluides appauvris en naphtalène

Country Status (1)

Country Link
WO (1) WO2014047000A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5302769A (en) * 1992-12-07 1994-04-12 Mobil Oil Corporation Process for making alkylated polycyclic aromatics
US5321182A (en) * 1990-07-27 1994-06-14 Nippon Steel Chemical Co., Ltd. Process for preparing 2-alkyl-6-ethylnaphthalene
US7189887B2 (en) * 2004-12-13 2007-03-13 Catalytic Distillation Technologies Process for removing naphthalene from alkylaromatics
US7241930B2 (en) * 2003-04-16 2007-07-10 Exxonmobil Chemical Patents Inc. Transalkylation of aromatic fluids

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5321182A (en) * 1990-07-27 1994-06-14 Nippon Steel Chemical Co., Ltd. Process for preparing 2-alkyl-6-ethylnaphthalene
US5302769A (en) * 1992-12-07 1994-04-12 Mobil Oil Corporation Process for making alkylated polycyclic aromatics
US7241930B2 (en) * 2003-04-16 2007-07-10 Exxonmobil Chemical Patents Inc. Transalkylation of aromatic fluids
US7189887B2 (en) * 2004-12-13 2007-03-13 Catalytic Distillation Technologies Process for removing naphthalene from alkylaromatics

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