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US5395981.Pdf |||||||||||||| USOO5395981A United States Patent (19) 11 Patent Number: 5,395,981 Marker (45. Date of Patent: ck" Mar. 7, 1995 (54) HYDROCARBON CONVERSION BY 4,307,254 12/1981 Smith, Jr. ............................ 568/697 CATALYTC DISTILLATION 4,950,803 8/1990 Smith, Jr. et al. .................. 568/697 5,118,871 6/1992 Cikut et al. ......................... 568/697 75 Inventor: Terry L. Marker, Warrenville, III. 5,258,560 1 1/1993 Marker ................................ 568/697 73 Assignee: UOP, Des Plaines, III. Primary Examiner-Howard T. Mars * Notice: The portion of the term of this patent Stone?igent or Firm-Thomas K. McBride; John F. subsequent to Nov. 3, 2010 has been pears, Jr. disclaimed. 57 ABSTRACT 21 Appl. No.: 112,299 Ethers suitable for use as high octane oxygenate addi 22 Fed: Aug. 27, 1993 tives for motor fuels or other compounds such as alco 22 e llg hols or alkylates are produced in a catalytic distillation Related U.S. Application Data process wherein a. C4-plus isoolefin(s) and an alcohol A present in the catalytic distillation zone overheadWerea 63 Continuation-in-part of Ser. No. 902,179, Jun. 22, 1992, stream are charged to a packed liquid-phase reaction Pat. No. 5,258,560. Zone containing an etherification catalyst before being 51 int. Cl. .............................................. CO7C 41/06 recycled to the overall catalytic distillation zone. The 52 U.S. Cl. ............................. 568/697; 203/DIG. 6; effluent of the liquid-phase reactor is returned to the 568/694; 585/709; 585/446 catalytic distillation zone at a point above the catalyst in 58 Field of Search .................. 568/697; 203/DIG. 6 this zone. The feed(s) to the process passes directly into 56 References Cited the catalytic distillation Zone, without passage through a prereactor, at a point iocated below a majority of U.S. PATENT DOCUMENTS catalyst bed in the catalytic distillation zone. 3,506,408 4/1970 Kageyama et al. ................... 23/288 3,634,535 l/1972 Haunschild ..................... 260/677 A 14 Claims, 1 Drawing Sheet U.S. Patent Mar. 7, 1995 5,395,981 5,395,981 1. 2 tions which are effective to promote both the exother HYDROCARBON CONVERSION BY CATALYTIC mic reaction of said isoolefin and alcohol to form a DISTILLATION product ether and the fractional distillation of the con tents of the catalytic distillation zone into an overhead CROSS REFERENCE TO RELATED APPLICA 5 vapor stream comprising said isoolefin and said alcohol TION and a bottoms stream which is rich in the product ether, This application is a continuation-in-part of my prior with said isoolefin and said alcohol first entering the application Ser. No. 902,179, filed 22 Jun. 1992, now catalytic distillation zone at a point intermediate upper U.S. Pat. No. 5,258,560. first and lower second catalyst retaining zones located O within the catalytic distillation zone; condensing the FIELD OF THE INVENTION overhead vapor stream to produce an overhead liquid The invention relates to a hydrocarbon conversion and passing a first portion of the overhead liquid into process useful in the etherification of isoolefins such as the catalytic distillation zone as reflux; passing a second isobutylene. The invention also relates to the use of portion of the overhead liquid into an external reaction catalytic distillation to perform hydrocarbon conver 15 zone operated at substantially liquid-phase conversion sion reactions. The invention specifically relates to a conditions and producing a reaction zone effluent catalytic distillation process wherein isobutylene is re stream, with the external reaction zone being operated acted with methanol to form methyl tertiary butyl ether in a manner which allows the heat of reaction of the (MTBE). ongoing etherification reaction to heat the reactants present in the external reaction zone; passing the reac RELATED ART tion zone effluent stream into the catalytic distillation U.S. Pat. No. 3,506,408 to O. Kageyama et al. illus Zone; and, removing at least a portion of the bottoms trates the use of catalytic distillation for carrying out stream from the process as a product stream. reversible liquid phase reactions such as the production of acetals and esters by the reaction of two organic feed 25 BRIEF DESCRIPTION OF THE DRAWING compounds. This reference teaches the use of ion ex The drawing is a simplified process flow diagram change resin particles located on shelves with layers of showing a catalytic distillation column 2, and a close packing such as Raschig rings located above the cata coupled liquid-phase reaction zone 15 which discharges lyst. its effluent into the catalytic distillation column 2 via U.S. Pat. No. 3,634,535 to W. Haunschild and the 30 line 17. references incorporated therein show that ethers, in cluding methyl tertiary butyl ether, can be produced by DETAILED DESCRIPTION AND PREFERRED catalytic distillation performed using catalyst located on EMBODIMENTS distillation trays or with catalyst in the form of a resin The continuous quest for more economical processes coating on vapor-liquid packing used to promote distill 35 for the production of petrochemicals is driving the lation. Etherification by catalytic distillation using simi development of etherification and alkylation processes lar methods is also described in U.S. Pat. No. 4,950,803 employing “catalytic distillation'. In these processes issued to L. A. Smith et al. the conversion catalyst is retained within a structure or The first commercial applications of catalytic distilla container capable of promoting substantial vapor-liquid tion to etherification, as per the teachings of references contact and fractional distillation concurrently with the such as U.S. Pat. No. 4,307,254 to L. A. Smith, Jr., in reaction although not normally at the exact point in the which the olefin feed stream is passed directly into the apparatus. The overall apparatus normally resembles a catalytic distillation column reportedly resulted in com fractionation column. This apparatus is provided with mercially unsatisfactory performance. This led to the means to effect reflux and reboiling of the apparatus and adoption of a conventional liquid-phase "prereactor” 45 normally has separate vapor-liquid contacting devices, upstream of the catalytic distillation zone, with the e.g., fractionation trays devoid of catalyst in its upper prereactor-catalytic distillation sequence becoming the and lower ends to perform the desired separations. standard commercial flow as shown in U.S. Pat. No. In the case of exothermic reactions such as alkylation, 5,118,871 issued to J. J. Cikut et ai. the heat released by the reaction is allowed to vaporize 50 a portion of the reactants present in the catalytic distilla BRIEF SUMMARY OF THE INVENTION tion zone. This causes the more volatile reactants to The invention is a hydrocarbon conversion process concentrate in the vapor phase and pass upward for the production of ethers which provides good reac through the overall apparatus while the less volatile tant utilization and ether yields without requiring a product compound(s) flow downward in a liquid phase. prereactor or an excessive amount of catalyst in the 55 This allows a facile method for separating the product catalytic distillation zone. It has been found that the from the reactants. This fractionation within the reac close-coupled reactor of the subject process need only tion zone aids in product recovery but more impor contain 30 percent of the catalyst present in the prior art tantly also tends to drive the reaction to completion by prereactor. The subject process can also be used in a removing the product compound(s) and supplying fresh variety of petrochemical applications including the 60 reactants. A very high degree of conversion can there production of diisopropyl ether and the hydration of fore be achieved for equilibrium limited reactions by olefins. employing catalytic distillation in suitable processes One broad embodiment of the invention may be char including etherification, alkylation and hydration. The acterized as a process for the production of ethers previously cited references describe catalytic distilla which comprises a process for the production of ethers 65 tion in detail. which comprises the steps passing at least one C4 to C6 It was suggested in the past to apply catalytic distilla isoolefin and a C1 or C2 alcohol into a catalytic distilla tion to a wide variety of processes such as butene isom tion zone maintained at mixed-phase conversion condi erization (U.S. Pat. No. 2,403,672 to M. P. Matuzak); 5,395,981 3 4 the hydrolysis of low molecular weight olefin oxides to catalytic distillation zone. That is, the total mass flow of produce mono-alkylene glycols (U.S. Pat. No. 2,839,588 the feed streams fed into the catalytic distillation zone to A. S. Parker); and the production of MTBE as de should be substantially free of the product ether. As scribed above. These early disclosures did not lead to some ether may possibly be present in a stream being commercialization. Catalytic distillation has only re recycled to the catalytic distillation zone, the term sub cently emerged as a commercially viable hydrocarbon stantially free is intended to indicate a concentration conversion and petrochemical processing tool, primar below 1.0 mole percent and preferably below 0.5 mole ily because of a legislated demand for oxygenates for percent. motor fuel in the U.S. The liquid phase reaction zone is "close-coupled' to Advantages attributed to the catalytic distillation O the catalytic distillation zone and is part of a recycle concept, wherein reaction products are continuously loop returning light reactants and some products to the separated from the reactants and removed from the catalytic distillation zone. This allows the process to reaction zone by fractional distillation performed con increase the rate of ether production from an equal currently with the reaction, include a decrease in the amount of catalytic distillation zone packing and to capital cost of the plant needed to perform the process, 15 reduce the height and cost of the required apparatus.
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