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Catalytic Removal of Peroxide Contaminants from a Methanol-Tertiary Butyl Alcohol Recycle Stream

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Catalytic Removal of Peroxide Contaminants from a Methanol-Tertiary Butyl Alcohol Recycle Stream Europaisches Patentamt 19 European Patent Office Office europeen des brevets © Publication number : 0 581 530 A1 12 EUROPEAN PATENT APPLICATION © Application number : 93305788.7 © int. ci.5 : C07C 29/132, C07C 29/88, C07C 41/09, C07C 31/12 @ Date of filing : 22.07.93 @ Priority : 28.07.92 US 920742 © Inventor : Sanderson, John Ronald 15290 Faubion Trail (43) Date of publication of application : Leander, Texas 78641 (US) 02.02.94 Bulletin 94/05 Inventor : Knifton, John Frederick 10900 Catskill Trail Austin, Texas 78726 (US) @ Designated Contracting States : DE FR GB © Representative : Green, Mark Charles et al Urquhart-Dykes & Lord, 91 Wimpole Street TEXACO CHEMICAL COMPANY © Applicant : London W1M 8AH (GB) 3040 Post Oak Boulevard Houston, Texas 77056 (US) © Catalytic removal of peroxide contaminants from a methanol-tertiary butyl alcohol recycle stream. © Methanol-tertiary butyl alcohol recycle stream contaminated with residual amounts of peroxide contaminants such as tertiary butyl hydroperoxide, ditertiary butyl peroxide, allyl tertiary butyl peroxide, etc., can be effectively catalytically treated with a catalyst consisting essentially of titania-supported transition met- als to substantially completely decompose the peroxide contaminants to thereby provide a treated methanol-tertiary butyl alcohol product substantially free from contaminating quantities of such peroxides. O CO If) 1iJOujD_i 00 (LOhOK If) LU Jouve, 18, rue Saint-Denis, 75001 PARIS EP 0 581 530 A1 This invention relates to the catalytic purification of peroxides-contaminated methanol-tertiary butyl alco- hol (MeOH/TBA). More particularly, this invention relates to a method for the purification of a MeOH/TBA re- cycle stream formed during the preparation of methyl tertiary butyl ether (MTBE) from methanol and from ter- tiary butyl alcohol prepared by the molybdenum-catalyzed reaction of propylene with tertiary butyl hydroper- 5 oxide. In accordance with the present invention, MeOH/TBA contaminated with peroxides is brought into con- tact with a titanium dioxide (titania) supported transition metal catalyst in order to substantially selectively de- compose the peroxide contaminants. Methyl tertiary butyl ether (MTBE) can be prepared by the catalytic reaction of tertiary butyl alcohol (TBA) with methanol. Normally, an excess of methanol is used. 10 Tertiary butyl alcohol can be prepared from isobutane. Isobutane can be reacted with oxygen to form oxy- gen-containing reaction products, principally tertiary butyl hydroperoxide. The tertiary butyl hydroperoxide can be decomposed (normally in the presence of a catalyst) to form tertiary butyl alcohol. However, the tertiary butyl alcohol will be contaminated with other oxygenated by-products, such as tertiary butyl hydroperoxide, ditertiary butyl peroxide, allyl tertiary butyl peroxide and isopropyl hydroperoxide, that are not easily removable 15 by distillation. Tertiary butyl alcohol prepared in this manner can be used as a feedstock for the present in- vention. It is known to prepare tertiary butyl alcohol by the molybdenum-catalyzed reaction of propylene with ter- tiary butyl hydroperoxide. Thus, tertiary butyl hydroperoxide may be reacted with propylene by a process of the type disclosed in Kollar (US-A-3,351,635) to provide a reaction product comprising unreacted propylene, 20 propylene oxide, tertiary butyl alcohol and residual quantities of oxygenated impurities, such as ditertiary butyl peroxide, tertiary butyl hydroperoxide and allyl tertiary butyl peroxide, that remain dissolved in tertiary butyl alcohol recovered from the reaction mixture. Tertiary butyl alcohol prepared in this manner can also be used as a feedstock for the process of the present invention. Thus peroxide contaminants will be present in the reaction medium that is formed when excess methanol 25 is mixed with the contaminated tertiary butyl alcohol. The contaminants will remain in the MTBE reaction prod- uct formed by the catalytic reaction of the contaminated tertiary butyl alcohol with excess methanol to form methyl tertiary butyl ether. When MTBE is prepared in a continuous process by this method, the MTBE reaction product can be separated by distillation into a distillation fraction containing substantially all of the MTBE formed during the reaction and into a separate fraction comprising water, methanol and tertiary butyl alcohol. The sep- 30 arate fraction, after being dewatered, is suitable for use as a recycle fraction. It has been discovered in accordance with the present invention that when the MeOH/TBA is recovered from the MTBE reaction product for recycle, the peroxide contaminants introduced into the reaction medium with the contaminated tertiary butyl alcohol will be concentrated in the MeOH/TBA recycle stream. As a con- sequence, the recycle stream will be contaminated with minor quantities of peroxides such as ditertiary butyl 35 peroxide, tertiary butyl hydroperoxide and allyl tertiary butyl peroxide. It is an object of the present invention for these peroxides to be removed in order to prevent their accumulation in the reaction medium. In US-A-4,822,921 there is disclosed a method for producing MTBE by reacting tertiary butyl alcohol and methanol in the presence of a catalyst comprising an inert support, such as titania, having a phosphoric acid impregnated thereon. 40 US-A-4,827,048 discloses a method for producing MTBE by reacting tertiary butyl alcohol and methanol in the presence of a catalyst comprising a heteropoly acid such as 12-tungstophosphoric acid or 12-molybdo- phosphoric acid on an inert support, such as titania. Sanderson et al US-A-4,547,598 discloses the use of unsupported cobalt borate and cobalt borate sup- ported on titanium dioxide to decompose organic hydroperoxides to alcohols. It has also been proposed to re- 45 move the residual hydroperoxide contaminants from tertiary butyl alcohol through the use of a heterogeneous cobalt oxide catalyst containing a copper oxide promoter as shown, for example, by Coile US-A-4,059,598. Al- lison et al in US-A-3,505,360 have more generically taught that alkenyl hydroperoxides can be decomposed catalytically through the use of a catalyst based on a metal or compound of a metal of group IV-A, V-A or VI- A. so in DE-A-3248465 a two-step process is disclosed wherein isobutane is oxidized noncatalytically with air to a conversion of about 48-90% to form the corresponding hydroperoxide, which is then catalytically decom- posed under hydrogenation conditions in the presence of a supported catalyst such as palladium, platinum, copper, rhenium, ruthenium or nickel to form tertiary butyl alcohol. The decomposition product obtained using 1.3% palladium on lithium spinel as a catalyst contained significant quantities of acetone, water and methanol. 55 A process for the decomposition of peroxides, such as a mixture of tertiary butyl hydroperoxide and tertiary butyl alcohol formed by the noncatalyzed oxidation of isobutane is disclosed in Taylor et al US-A-4,551,553 wherein the decomposition is catalyzed with a catalytic system composed of chromium and ruthenium which is soluble in the hydroperoxide. 2 EP 0 581 530 A1 Sanderson et al also disclose catalytic methods for the purification of t-butyl alcohol contaminated with residual quantities of tertiary butyl hydroperoxide and ditertiary butyl peroxide using catalysts composed of mixtures of nickel, copper, chromia and iron (US-A-4,704,482), catalysts composed of mixtures of iron, copper, chromia and cobalt (US-A-4,705,903), catalysts composed of mixtures of nickel, copper, chromium and barium 5 (US-A-4,873,380), or catalysts composed of metals selected from group VIB orVIIIB of the Periodic Table (US- A-4,742,179). This invention relates to a method for the removal of residual quantities of peroxide contaminants, such as ditertiary butyl peroxide, tertiary butyl hydroperoxide and allyl tertiary butyl peroxide, from MeOH/TBA wherein MeOH/TBA contaminated with peroxides is brought into contact with a titanium dioxide (titania) sup- 10 ported transition metal catalyst in order to substantially completely decompose the peroxide contaminants. More particularly, this invention relates to a process for continuously treating a peroxides-contaminated MeOH/TBA stream prior to use of the stream as a recycle stream in the continuous reaction of methanol with tertiary butyl alcohol (TBA) to form methyl tertiary butyl ether wherein MeOH/TBA contaminated with perox- ides is brought into contact with a titanium dioxide (titania) supported transition metal catalyst in order to sub- is stantially completely decompose the peroxide contaminants. Still more particularly, this invention relates to a continuous process (a) wherein peroxides-contaminated tertiary butyl alcohol is continuously mixed with excess methanol to form a reaction medium (b) wherein the reaction medium is continuously charged to a reaction zone containing an et herif ication catalyst to continuously convert a portion of the methanol and tertiary butyl alcohol in the reaction medium into MTBE and water and 20 to form an MTBE reaction product, (c) wherein the MTBE reaction product is continuously separated into an MTBE distillation fraction and a second fraction comprising water, unreacted methanol, unreacted tertiary butyl alcohol and peroxide contaminants, (d) wherein the second fraction is continuously dewatered to form a MeOH/TBA recycle fraction, (e) wherein the MeOH/TBA recycle fraction (which is contaminated with peroxides) is continuously brought into contact
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