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A/ Žervy Fivy Patented June 28, 1949 2,474,568 UNITED STATES PATENT OFFICE 2,474,568

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A/ Žervy Fivy Patented June 28, 1949 2,474,568 UNITED STATES PATENT OFFICE 2,474,568 June 28, 1949. L. A. BANNON ETAL 2,474,568 DILUTION AND HYDROLYSIS OF DIETHYL SULFATE SOLUTIONS Filed June 11, 1946 -e- -mser STRONG VENT GAS VENT GAS ACID INLET 25, 26 WATER INET YN r R W O ALK Ali sts, WATER INET HSEEE /S O 23 2 ABSORBER GENERATOR 3. g else \- 24 AS S. E) W. 22 29 d 7 es ea HEATER SS E32. EXTRACT . -se as MXER 8. - 6 3. HYDROLYZER 2 720- -e- 4. y --WATER wn s 6 g St SECOND N g.is () sizeis (VENT2SE2 FEED GAS INLET EXTRACT COOLER RECYCLE STRONG ACID s STRONG ACD ACD OLUTE OR OLEUM NET CONCENTRATOR ALCOHOL TANK Za-wys /2 23a7/VMOM, 1/Y42 Ca/aaalas A. M7o/e/ea a 4. A/ Žervy fivy Patented June 28, 1949 2,474,568 UNITED STATES PATENT OFFICE 2,474,568. OLUTIONANDHYDROLYSIS OF DETHY, SULFATE SOLUTIONS Lewis A. Bannon, Baton Rouge, La., and; Charles E: Morrell, Westfield, N.J., assignors to Standa ard Oil Development Company, a corporation of Delaware Applieation June 11, 1946, Serial No. 676,078. 9, Claims: (C. 260-639) 1. 2. This, invention relates to the production of hydrolysis of the diethylistilfate:according to this alcohols by hydrolysis of sulfuric acid extracts of: invention, it is accordingly possible to carry, re normally gaseous, olefins, and is particularly ap action)3 to virtual completion before 4 can cont. plicable to the preparation of pure ethyl alcohol. tribute large concentrations of alcohol for re When solefins such as: ethylete are absorbed in: 5 action 1. In this manner, formation of ether strong sulfuric acid; the: resulting solution con from the diethylistilfate is greatly suppressed. tains ethylhydrogen sulfate, sulfuric acid, and Also, reactions2.igreatly limits:the time permitted also diethylsulfate; and tethyl alcohol. The:COn for the hydrolysis of the ethylsulfate and for this"; position approaches equilibrium which varies with . reason it has been proposed that this reaction be the acid strength. Under the conditions, nor 0 carried out' by feeding: the extract to a tower mally used for absorbing ethylene.in strong: sul countercurrent to stripping steam, which removes. furic acid}of about:90 to 100:weight percent con the alcohol as fast, as it is formed. However, as centration, the resulting solution will, contain a indicated above, such extract. fed to the tower substantial proportion of, diethyl, sulfate. This must be: Substantially, free of diethyl sclfate in compound. (B.P. 208° C.) issvolatile: with steam, 15 order to keep this volatie: compound outs of the hence is... carried overhead in steam:stripping of alcohol distillate. alcohol; from the partially hydrolyzed extract. It has...also been: found that the hydrolysis of It is an objectionable: impurity in the resulting the diethyl sulfate: in the original acid extract alcohol, aS.it liberates:sulfuric acidiby hydrolysis, can be carried out much more completely than causing corrosion and imparting: a bad odor. to 20 heretofore possible by thes use of two separate the alcohol. Hence, it is: desirable to remove.'di hydrolysis: Zones: prior to the steam stripper and ethyl sulfate as completely as: possible from the preferably by providing for stream-line:flow. of acid extract before distilling-off the alcohol. This extract through at least the:second of these zones. is normally, attempted by: hydrolysis, but, such Under such conditions a major portion, and pref continuous operations: as:;have: heretofore been 25 erably about .75 to .90% ; of the diethyl sulfate is: described either...involve-incomplete hydrolysis of: hydrolyzed in the first zone, fort which a conven the diethyl Sulfate, or else involve excessive for- - tional mixing: attoclave may be used, and the mation of diethyl ether. For example, when the: final: hydrolysis sis' conditicted in a second stage hydrolysis is conducted by passing:Water, and acid: in which preferably no mixing:of the feed stream extract continuously into a hydrolyzer. With mix 30 with the outlet stream is permitted. This second ing, and withdrawing to a steam stripper: a con stager hydrolysis is spreferably carried out',in a tinuous stream of the -hydrolyzed" material, the tower or pipe: coil of c relatively. Small diameter latter Will always contain sonne-diethyl-sulfate, compared to its length, in order, to prevent by even though a very long. residence time-is-per passing. It', may also be conducted in... vessels mitted in the hydrolyzer. If ther mixer is oper 35 suitably provided with baffles - to divide the re ated batchwise, and a sufficiently long time is action Spacerinto a number of separate zones and permitted to hydrolyze-the-diethyl sulfate.com . to cause the extract to flow progressively through: pletely, very large- equipment is required. In: these. Zonesis with no by-passing from initial to final Zones and vice versa. both operations: the formation of ether is exces 40 The drawing: is a diagrammatic-illustration in sive, as the following reactions occur: partial sectional elevation of one suitable type, of equipment, for carrying out the process of this invention, and indicatess the flow of mate rials. Stitable conditions for there various ab (2) C2H5HSO4--C2H5OH=C2H5OC2H5-H2SO4 : 45 Sorption, hydrolysis and distillation operations: Hence, it has been found desirable to limit the are also given in the following: detailed descrip time during-hydrolysis in which substantial con tion, which is presented for purposer of 'illustra centrations of diethylsulfate and ethyl alcohol tion and not in limitation of this invention. are permitted to be in contact with each other, Referring to the drawing; strong:sulfuric acid in order to avoid reaction 1 50 of about 90-100% concentration, preferably The desired reactions' in hydrolysis of the ex 96-100%, is passed by liner through heater 2. into the upper-portion of an absorption tower 3 at a temperature of about 40 to 50° C. A feed gase containing ethylene such as a Ca fraction of 55 gas-obtained by cracking gas-oil attemperatures Reactions 3 and 1 have been found to be much of about 650 to 760. C. in the presence of steam more rapid than 2 or 4 in .40.55% acid attem and-containing 25 to 50% ethylene, is passed by peratures below about 90°C. In the two-stage lirae 4 into the lower portion of the tower 3 at a 2,474,568 3. 4. pressure of about 400 to 500 pounds per Square drolyzed extract free of diethyl sulfate. Addi inch. The tower contains suitable bubble trayS tional water to further dilute the extract to a or other packing for providing intimate liquid sulfuric acid concentration of about 40 to 45 gas contact and is also provided with Suitable weight percent (hydrocarbon-free basis) may be heat exchangers (not shown) distributed added by line S. This second hydrolysis Zone throughout the tower to remove the heat of re is preferably maintained at a temperature be action and to maintain the temperature in the tween about 80 and 90 or 95° C. With Sufficient tower at about 70 to 85 or 90 C. residence time for the extract therein to permit Under such conditions more than 90% of the substantially complete hydrolysis of the entering ethylene is dissolved in the resulting acid extract 0 diethyl sulfate. This time is Suitably about 20 which contains about 1.3 mols of ethylene per to 30 minutes, depending upon the temperature mol of sulfuric acid, of which about 2% is in the of the vessel and the diethyl sulfate content of forth of diethyl sulfate. This extract is renowed the extract supplied thereto. This time does not from the absorber by line 5 and is passed through require particularly close control because of the cooler 6 and then, at a temperature of about 45° 5 low concentration of diethyl sulfate present. C., into an extract mixer and first hydrolysis The resulting extract, substantially free of di stage , suitably by a number of jets 8 arranged ethyi sulfate and containing ethyl hydrogen Sul on the extract feed pipe in order to provide thor fate and ethyl alcohol, is passed by line 9 to a ough mixing in this hydrolyzer, which is main suitable alcohol generator 28 in which the extract tained at a pressure of about 50 pounds per Square 20 is stripped with steam or other suitable gases for inch gauge and at a temperature of about 80 to distilling off the ethyl alcohol. The generator 29 90° C. also acts as a third hydrolysis Zone in which the The physically dissolved gases which are re hydrolysis of ethyl hydrogen Sulfate is com leased from the extract in this mixer due to the pleted. In order to reduce ether formation, it reduction in pressure are vented from the upper 25 is desirable to remove the alcohol from the extract portion of the vessel through line 9 and are as rapidly as possible, as by stripping the extract washed in the vent gas scrubber With Water in a tower countercurrent to steam. The tower supplied by line , this water then being passed 23 contains suitable packing or distributing plates by line 2 and pump f3 into the vessel in Order for providing intimate liquid-gas contact between to dilute the extract therein. Sufficient Water 30 the down-flowing extract and steam which is Sup is supplied to maintain a Sulfuric acid concen plied to the lower portion of the tower by line 2. tration in this first hydrolyzer of about 40 to 55 The steam-alcohol vapor mixture leaves the top Weight percent (hydrocarbon-free basis). That of the tower through a dephlegmator 22 and then is, the Weight percent of Sulfuric acid is calculated is passed by line 23 into a scrubbing tower 24 in on the basis of the total equivalent weights of which it is scrubbed first with aqueous alkali Sup sulfuric acid and water present in free and com plied by line 25 and then with Water Supplied by bined form, the hydrocarbon content of the ex line 23.
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