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Process for the Production of Methyl Acetate by Esterifying Methanol With

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Process for the Production of Methyl Acetate by Esterifying Methanol With Europâisches Patentamt European Patent Office (jî) Publication number: 0 060 719 Office européen des brevets B1 EUROPEAN PATENT SPECIFICATION (§) Date of publication of patent spécification: 27.11.85 ® Int. ci.4: C 07 C 69/14, C 07 C 67/08 ® Application number: 82301333.9 @ Dateoffiling: 16.03.82 (54) Process for the production of methyl acétate by esterifying methanol with acetic acid. (M) Priority: 17.03.81 GB 8108336 (73) Proprietor: BP Chemicals Limited Belgrave House 76 Buckingham Palace Road London, SW1W 0SU (GB) Date of publication of application: 22.09.82 Bulletin 82/38 Inventor: Yeomans, Bertram BP Chemicals Limited Saltend (§) Publication of the grantof the patent: Hedon Hull, HU12 8DS (GB) 27.11.85 Bulletin 85/48 @ Représentative: Harry, John et al (§) Designated Contracting States: c/o The British Petroleum Company pic Patents BEDE FR GB ITNL Division Chertsey Road Sunbury-on-Thames Middlesex TW16 7LN (GB) (5Ï) Références cited: FR-A-1 194 137 US-A-2 787 636 m o> o o o Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall CL be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been LU paid. (Art. 99(1) European patent convention). Courier Press, Leamington Spa, England. recovering from the product an overhead fraction comprising methyl acetate characterised in that The present invention relates to an improved from an intermediate point in the column there is process for the production of methyl acetate by removed a liquid sidestream fraction comprising esterifying methanol with acetic acid. water and entrainer. Methyl acetate, besides retaining its usefulness The entrainer may suitably be added to the in solvent applications, is gaining importance as esterification reaction vessel or to a suitable point an intermediate in the production of other in the distillation column. The process may be valuable products. Owing to its unfavourable operated batchwise or continuously preferably physical properties (viz. composition of azeo- continuously. tropes and solubility in water) pure methyl A preferred embodiment is characterised in that acetate containing low concentrations of the methanol and acetic acid are continuously fed methanol and water is not readily obtainable to the esterification reaction vessel containing using conventional processes. A conventional entrainer, acetic acid and esterification catalyst to esterification process which may be used for the produce a product comprising entrainer, un- production of methyl acetate comprises the reacted methanol, methyl acetate and water, addition of a feed mixture comprising excess distilling from the product in the distillation methanol and acetic acid to an esterifier contain- column an overhead fraction comprising methyl ing aqueous acetic acid and a strong acid catalyst acetate, removing from the intermediate point in (e.g. toluene-para-sulphonic acid) under reflux the column a liquid sidestream fraction compris- conditions. A mixture of methyl acetate, reaction ing water, entrainer and methyl acetate, separat- water and the excess methanol is taken overhead ing methyl acetate and entrainer in the side- as a distillate product. A typical ester distillate stream fraction from water and returning product obtained by use of a 2:1 molar ratio feed separated methyl acetate and entrainer to a point of methanol:acetic acid should theoretically lower in the column than the sidestream fraction comprise 59.9% w/w methyl acetate, 26% w/w removal point. methanol and 14.5% w/w water. Conventionally The esterification reaction vessel may be purification of such a crude ester distillate is separate from the distillation column or integral effected in a multi-stage process which typically therewith. Preferably the vessel is a kettle at the incorporates hydroselection (for removal of base of the distillation column, which suitably methanol) and azeotropic drying (for removal of may contain not less than 8 theoretical plates and water). Additional distillation steps are required preferably from 15 to 50 theoretical plates. When- to recover methanol from the hydroselection base ever, the reaction vessel is separate from the product and methyl acetate from the decanter distillation column it is preferred to recycle the water phase/entrainer for recycle. residue from the base of the column to the US 2,787,636 describes the addition of an reaction vessel. auxiliary liquid, for example butyl acetate, to an Preferably the feed comprises equimolar esterification process. However, in this case the amounts of methanol and acetic acid. auxiliary liquid allows the esterification reaction The elevated temperature may vary over a to be carried out at an elevated temperature. The moderately wide range but must be sufficient, in auxiliary liquid also remains in the esterification the case where the reaction vessel is integral with reactor throughout the reaction and does not act the distillation column, to distil methyl acetate, as an entrainer. water and entrainer out of the reaction mixture. French Patent 1,194,137 also described an Thus at atmospheric pressure suitable reaction esterification process using, for example, butyl temperatures are in the range 100° to 120°C, acetate as an entrainer but in this patent the preferably 105° to 115°C. To achieve the elevated entrainer is removed overhead from the distilla- temperature the reaction vessel may be provided tion column and not at an intermediate point. with, for example, steam coils, or other forms of We have now found that methyl acetate of heating. improved purity in terms of methanol and water The reflux necessary for successful fractiona- content and hence of greater suitability as a tion may suitably be provided by condensing the feedstock in certain reactions, such as the produc- overhead fraction in a vertical condenser and tion of acetic anhydride by reaction with carbon returning a portion of the condensate to the monoxide, can be produced in a simpler manner column (primary reflux), the remainder of the than hitherto. condensate being removed as methyl acetate Accordingly, the present invention provides a product. The primary reflux ratio may suitably be process for the production of methyl acetate in the range 1:2 to 10:1, preferably from 1:1 to which process comprises reacting in an esterifica- 5:1. tion reaction vessel methanol at elevated In the embodiment in which the reaction vessel temperature with acetic acid in the presence of an constitutes the kettle of the distillation column the esterification catalyst and an entrainer which is reflux ratio is preferably sufficient to maintain the sparingly soluble in water and which forms a water content of the reaction vessel at not more minimum boiling point azeotrope therewith to than 10% by weight of the reactor contents and form a product comprising entrainer, methyl preferably not more than 3% by weight. acetate and water, and in a distillation column, Operating at atmospheric pressure the side- stream fraction is preferably removed at a point in tive adsorption using a molecular sieve and/or by the column at which the column temperature is reaction with acetic anhydride. between 75 and 90°C. In terms of theoretical With respect to the reactants, it is immaterial plates this point should be not less than 5 and whether the methanol and/or acetic acid contain preferably not less than 10 theoretical plates from water. the base of the column. In addition to water and The entrainer may be any hydrocarbon, ether, entrainer, the liquid sidestream fraction may ester or ketone which is sparingly soluble in water additionally comprise methyl acetate. This may and which forms a minimum boiling point azeo- be separated, suitably by decantation, into an trope with water. Examples of suitable entrainers upper organic phase comprising methyl acetate are toluene, diisobutyl ether, normal- and iso- and entrainer which may be recycled back to the butyl acetate and methyl isobutyl ketone. Prefer- column and a lower aqueous phase comprising ably the entrainer is an acetic acid ester such as water. The aqueous phase may suitably be dis- n-butyl acetate. An advantage of using an acetic carded. acid ester is that it can be formed 'in situ', for The distillation column may suitably incor- example n-butyl acetate can be formed by porate means for facilitating the removal of a incorporating n-butanol in the reaction mixture. liquid sidestream fraction which means may take Methyl acetate (boiling point 57°C) and butyl the form of a deep weir or chimney tray located acetate (boiling point 126°C) can be readily immediately below the point in the column from separated by distillation. which the sidestream fraction is removed. Using The amount of entrainer present may suitably such means it may be possible to maximise the be greater than 1 %, preferably from 20 to 60% by concentration of water in the sidestream fraction weight based on the total weight of the reaction by facilitating phase separation within the mixture. column, thereby saving energy. The esterification catalyst may suitably be a Since substantially all the entrainer remains mineral acid such as sulphuric acid or an organic within the column, only small amounts being lost acid such as toluene-para-sulphonic acid, of in the overhead fraction and the sidestream which toluene-para-sulphonic acid is preferred.
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