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Improved Process to Co-Manufacture Acrylonitrile and Hydrogen Cyanide

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Improved Process to Co-Manufacture Acrylonitrile and Hydrogen Cyanide (19) TZZ 4859B_T (11) EP 2 254 859 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C07C 253/34 (2006.01) 09.01.2013 Bulletin 2013/02 (86) International application number: (21) Application number: 09717270.4 PCT/US2009/036111 (22) Date of filing: 05.03.2009 (87) International publication number: WO 2009/111605 (11.09.2009 Gazette 2009/37) (54) IMPROVED PROCESS TO CO-MANUFACTURE ACRYLONITRILE AND HYDROGEN CYANIDE VERBESSERTES VERFAHREN ZUR GEMEINSAMEN HERSTELLUNG VON ACRYLNITRIL UND CYANWASSERSTOFF PROCEDE AMELIORE DE CO-FABRICATION D’ACRYLONITRILE ET DE CYANURE D’HYDROGENE (84) Designated Contracting States: • STIMEK, Richard, T. AT BE BG CH CY CZ DE DK EE ES FI FR GB GR Old Hickory, TN 37138-1016 (US) HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO SE SI SK TR (74) Representative: Towler, Philip Dean Dehns (30) Priority: 05.03.2008 US 74775 St Bride’s House 10 Salisbury Square (43) Date of publication of application: London 01.12.2010 Bulletin 2010/48 EC4Y 8JD (GB) (73) Proprietor: E. I. du Pont de Nemours and Company (56) References cited: Wilmington, DE 19898 (US) US-A- 3 185 636 US-A- 6 084 121 US-B1- 6 296 739 US-B1- 6 355 828 (72) Inventors: • BASHAM, Brent, E. Cordova Tennessee 38016 (US) Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 254 859 B1 Printed by Jouve, 75001 PARIS (FR) 1 EP 2 254 859 B1 2 Description commonly referred to as "synthesis gas" or "syn-gas." The syn-gas then undergoes an additional high temper- FIELD OF THE INVENTION ature reaction to yield methanol. It is desirable to avoid the inefficiencies of an intermediate step to convert meth- [0001] This invention relates to a process for the co- 5 ane to methanol while increasing production of HCN in manufacture of acrylonitrile and hydrogen cyanide with an ACRN reaction system. improved control and efficiency. [0008] Other alcohols and ketones have been added to increase production of HCN in an acrylonitrile process. BACKGROUND OF THE INVENTION While such processes increase the HCN to ACRN ratio, 10 the total pounds of acrylonitrile is reduced, and adding [0002] Acrylonitrile (ACRN) is an important monomer additional alcohols and ketones to the reactor, further for the synthesis of various polymers including acrylic accelerates catalyst deactivation. fibers, synthetic rubbers, nylons, and is the starting ma- [0009] HCN is a highly toxic and flammable gas. At terial for acrylic acids and acrylaminde. Processes to pre- high concentrations, risk increases for exothermic runa- pare acrylonitrile are well known, and include the so-15 way reaction through polymerization and decomposition, called "Sohio Process" in which propylene/ propane react which is a potentially explosive situation. Therefore, it is with ammonia and oxygen (air) over a catalyst at elevated critical in any process which uses and/or produces HCN temperatures ("ammoxidation"). Hydrogen cyanide that safety must be of highest priority. Thus, when in- (HCN) and acetonitrile (CH3CN) are produced as by- creasing concentration of HCN of a process, extreme products. 20 caution is needed to ensure safe operation of the proc- [0003] HCN is a valuable by- product due to it vast uses ess. as a starting material or as an intermediate. HCN is used, [0010] High concentrations of HCN in acrylonitrile sys- for example, as a starting material for the synthesis of tems are relatively unstable, and solid polymeric HCN various polymers, including polyamides, and chemicals. can form in the heads column, reducing column pressure. HCN is the starting material for metal cyanides including 25 The heads column is the distillation column in which HCN sodium cyanide and potassium cyanide, two compounds and ACRN are separated. The pressure drop raises the important in metallurgy for recovery of gold and the hard- column temperature further favoring HCN polymeriza- ening of steel. tion. Solid polymerization products plug equipment, such [0004] To increase HCN yield in the Sohio process, a as relief systems, valves, instruments, and piping, which technique commonly referred to as "methanol injection" 30 in turn, increase risks associated with HCN. may be employed. Methanol injection involves adding [0011] Downtime associated with cleaning of the solids methanol gas to the acrylonitrile reactor or feed to the and other downstream process equipped is increased reactor to increase HCN production. A conventional So- and results in substantial costs and loss production of hio process produces a ratio of acrylonitrile to HCN of ACRN and HCN. In U.S. Patents 6,296,739 and about 9 to 1, whereas using methanol injection, this ratio 35 6,793,776, Godbole discloses methods to reduce the risk can be decreased to 8 to 1. In a typical plant, use of of HCN polymerization based on reducing the amount of methanol injection can result in an increase of about 10 aqueous layer in the heads column. Godbole’s methods million pounds of HCN per year with coproduction of include increasing the reflux ratio of HCN to ACRN by about 360 to 400 million pounds of acrylonitrile per year. adding recycled or pure HCN to the heads column to [0005] Methanol injection has several disadvantages. 40 reduce the likelihood of polymer formation, among oth- Due to the burden placed on the system, overall yield of ers. Common practice is to reduce column pressure thus acrylonitrile can be reduced by as much as 5%. Methanol lowering the column temperature. reduces propylene content of the reactor, resulting in less [0012] There remains a need for co- production of acry- acrylonitrile being produced. High heat released at the lonitrile and HCN, wherein the ratio of ACRN and HCN catalyst surface as methanol reacts leads to catalyst de- 45 is less than that provided in a conventional Sohio proc- activation resulting in more frequent catalyst replace- ess. It is further desired to be able to vary this ratio. It is ment. Methanol can also react with ammoxidation inter- still further desired to avoid any negative effects on the mediates to form reactive intermediates that can lead to acrylonitrile process, such as catalyst deactivation, and polymer formation and fouling in downstream equipment. on downstream recovery and purification operations. It [0006] Methanol also reacts with oxygen in the system, 50 is further desired to have efficient conversion of methane consuming this reagent, and forming undesired by- prod- to HCN, or at least avoid equipment and energy cost of ucts, such as carbon oxides. producing methanol. It is further desired to maintain ef- [0007] Less obvious disadvantages of methanol injec- ficiency of oxygen consumption and to minimize forma- tion process are increased cost for equipment and energy tion of undesired by-products. It is still further desired to due to the need to convert methane to methanol. Meth- 55 use existing acrylonitrile recovery and purification equip- anol is typically produced by reaction of methane with ment. It is further critical that any increase in HCN con- steam under high temperatures and pressures over a centration be performed in a manner that does not com- copper catalyst yielding carbon monoxide and hydrogen, promise safety. The present invention meets these 2 3 EP 2 254 859 B1 4 needs. comprising hydrogen cyanide and the acrylonitrile prod- uct stream in an absorber column with water, to produce SUMMARY OF THE INVENTION a combined product stream, having a ratio of the acrylo- nitrile product stream to the stream comprising hydrogen [0013] 1. The present invention is a process for co- 5 cyanide of about 9 to 1 or less; (d) treating the combined manufacture of acrylonitrile and hydrogen cyanide com- product stream sequentially in a recovery column, a de- prising (a) combining a stream comprising hydrogen cy- canter having an aqueous layer and an organic layer, anide and an acrylonitrile reactor product stream, in an and a heads column, wherein pH is controlled by addition absorber column with water to produce a combined prod- of an acid at pH of 7.0 or less in the absorber column and uct stream, having a ratio of acrylonitrile to hydrogen cy- 10 the recovery column, and at pH less than 4.5 in the de- anide of about 9 to 1 or less; and (b) treating the combined canter and heads column; and (e) separating a crude product stream sequentially in a recovery column, a de- HCN stream from a crude acrylonitrile stream in the canter having an aqueous layer and an organic layer, heads column, treating the crude HCN stream in a HCN and a heads column, wherein pH is controlled by addition distillation column, and treating the crude acrylonitrile of an acid at pH of 7.0 or less in the absorber column and 15 stream in a drying column, wherein pH is controlled in the recovery column, and at pH less than 4.5 in the de- the HCN distillation column at pH less than 4.5. canter and heads column. The ratio of and at pH less than 4.5 in the decanter and heads column; and (e) sep- Acrylonitrile Reactor Product Stream arating a crude HCN stream from a crude acrylonitrile stream in the heads column, treating the crude HCN20 [0018] Acrylonitrile is produced in the present inven- stream in a HCN distillation column, and treating the tion, for example, and preferably, by the Sohio process.
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