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Process for the Preparation of a Caprolactam Precursor from Butadiene

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Process for the Preparation of a Caprolactam Precursor from Butadiene Europäisches Patentamt *EP001223155A1* (19) European Patent Office Office européen des brevets (11) EP 1 223 155 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.7: C07C 45/50, C07C 51/235, 17.07.2002 Bulletin 2002/29 C07C 67/39, C07C 67/36, C07C 227/08, C07C 41/54, (21) Application number: 01200120.2 C07C 67/38 (22) Date of filing: 15.01.2001 (84) Designated Contracting States: • Smits, Hubertus Adrianus AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU 6212 GC Maastricht (NL) MC NL PT SE TR • Spronken, Josephus Marie Hubertus Designated Extension States: 6241 BK Bunde (NL) AL LT LV MK RO SI • Wolters, Henricus Franciscus Wilhelmus 6101 BT Echt (NL) (71) Applicant: DSM N.V. • Boogers, Jeroen Antonius Franciscus 6411 TE Heerlen (NL) 6224 JK Maastricht (NL) • Gelling, Onko Jan (72) Inventors: 6129 HV Urmond (NL) • Sielcken, Otto Erik 6136 BG Sittard (NL) (54) Process for the preparation of a caprolactam precursor from butadiene (57) The invention relates to a process for the prep- presence of an alcohol resulting in a reaction mixture aration of a caprolactam precursor starting from butadi- comprising an acetal of pentenals. The invention further ene, whereby the process comprises a step in which relates to the preparation of methyl-3-pentenoate by ox- butadiene is hydroformylated into a mixture of pentenals idizing a pentenal and/or an acetal of pentenal contain- in the presence of carbon monoxide, hydrogen and a ing reaction mixture. hydroformylation catalyst. The invention also relates to a process in which butadiene is hydroformylated in the EP 1 223 155 A1 Printed by Jouve, 75001 PARIS (FR) EP 1 223 155 A1 Description [0001] The invention relates to a process for the preparation of a caprolactam precursor from butadiene. [0002] Such a process is described in WO-A-9702091. This publication discloses the reaction of butadiene with 5 carbon monoxide and water to 3-pentenoic acid in the presence of hydrogen iodide and a catalyst system comprising iodine, rhodium and an activated carbon support. [0003] A disadvantage of this process is that the use of iodide containing catalysts may result in corrosion of the equipment. [0004] The object of the invention is a process in which the above mentioned disadvantage does not occur or occurs 10 to a lesser degree. [0005] This object is achieved in that the process comprises a step in which butadiene is hydroformylated into a mixture of pentenals in the presence of carbon monoxide, hydrogen and a hydroformylation catalyst. [0006] It has been found that with this process no or less corrosion of the equipment occurs. An advantage of the process of the invention is that it is not necessary to use pure carbon monoxide. Carbonylation processes as for example 15 described in WO-A-9709201 require pure carbon monoxide. Carbon monoxide is usually prepared starting from syn- thesis gas. The derivation of carbon monoxide from synthesis gas is cumbersome because several separation steps, including the separation of carbon monoxide and hydrogen, are needed. A mixture of carbon monoxide and hydrogen is obtained as an intermediate in the preparation of carbon monoxide starting from synthesis gas, which mixture can be used in the process of the invention. A further advantage is that hydrofomylation of butadiene, compared with 20 carbonylation of butadiene, requires lower reaction temperatures (≤100 °C) resulting in higher catalyst stability. [0007] Several attempts have been made in the prior art for preparing methyl-3-pentenoate by reacting butadiene with carbon monoxide and methanol in the presence of a carbonylation catalyst. Although some of the disclosed catalyst systems are less corrosive, compared with the catalyst system as disclosed in WO-A-9702091, a stable catalyst system which is also economically attractive is never disclosed. An additional advantage of the process of the present invention 25 is that compounds formed in situ from butadiene having a boiling point near the boiling point of methyl-3-pentenoate, like for example vinylcyclohexene and octatriene, can be separated from the reaction mixture prior to methyl-3-pen- tenoate synthesis. Vinylcyclohexene and octatriene are undesired by-products as they result in undesired side-reac- tions and/or are potential catalyst poisons in subsequent catalysed reactions of methyl-3-pentenoate. Still another advantage of the process of the invention is that the boiling points of pentenals are lower than the boiling points of 30 methyl pentenoates. This is advantageous as the separation of the catalyst from the product mixture can be performed at a lower temperature resulting in inter alia a higher catalyst stability during separation. [0008] In the process according to the invention butadiene is reacted with carbon monoxide, hydrogen and a hydro- formylation catalyst in a liquid medium. The hydroformylation catalyst may be a solubilized metal-ligand complex cat- alyst. A preferred hydroformylation catalyst is a rhodium-organophosphorous ligand complex catalyst. Exemplary or- 35 ganophosphorous ligands are organophosphines, like for example monodentate and bidentate phosphines, and orga- nophosphites, like for example monodentate and bidentate phosphites. Hydroformylation of butadiene using a rhodium- phosphine or rhodium-phosphite complex catalyst is for example described in WO-A-9740002, EP-A-577042, US-A- 5312996, US-A-5817883, US-A-5821389, EP-A-872483, US-A-5892127 and US-A-5886237, the complete disclosures of which are incorporated as references. US-A-5710344 discloses the use of a complex of rhodium and bidentate 40 phosphorous ligands containing four P-C bonds and two P-O bonds (so called phosphinites) . These publications do not mention or suggest to prepare a caprolactam precursor via pentenals or derivatives thereof. [0009] Rhodium may be applied in any one of a variety of forms. The manner in which rhodium is introduced into the reaction mixture is not critical. As a rule, the catalytically active complexes based on a rhodium precursor such as for example Rh(CO)2(acac) (acac=acetylacetonate), Rh2O3,Rh4(CO)12,Rh6(CO)16, Rh(NO3)2, Rh(Oac)2 (Oac=ace- 45 tate) are formed in the reaction mixture. [0010] The rhodium concentration in the reaction mixture is not specially limited, but is optionally selected so that favorable results can be obtained with respect to catalyst activity and process economics. In general, the concentration of rhodium in the reaction mixture is between 10 and 10000 ppm, calculated as free metal. [0011] The molar ratio of organophosphorous ligands to rhodium is not specially limited. Generally, this ratio is from 50 about 0.5:1 or less to about 1000:1 or greater. [0012] The hydroformylation is carried out at a temperature of between room temperature and 200 °C, preferably from 50 to 120 °C, and most preferred from 90 to 100 °C. [0013] The hydroformylation is carried out at a pressure of between atmospheric pressure (0.1 MPa) to 20 MPa, preferably from 3 to 10 MPa. The pressure is generally equal to the combined hydrogen, carbon monoxide and buta- 55 diene partial pressures. The molar ratio hydrogen:carbon monoxide can be varied within wide limits and is generally between 10:1 and 1:10, preferably between 6:1 and 1:6 and most preferably betweem 2:1 and 1:2. [0014] The hydroformylation reaction is preferably conducted in the presence of an organic solvent for the catalyst system and optionally free ligand. Suitable solvents include those commonly employed in known metal catalysed hy- 2 EP 1 223 155 A1 droformylation reactions. The solvent may be a mixture of reactants, such as the starting unsaturated compound, the aldehyde product and/or by-products. Suitable solvents include saturated hydrocarbons such as kerosene, mineral oil or cyclohexane, ethers such as diphenyl ether, tetrahydrofuran or a polyglycol, ketones such as methyl ethyl ketone and cyclohexanone, nitriles such as acetonitrile, valeronitrile, and benzonitrile, aromatics such as toluene, benzene 5 and xylene, esters such as dimethylformamide, and sulfones such as tetramethylensulfone. [0015] The pentenals which are formed during hydroformylation of butadiene will actually be a mixture of 2-, 3- and 4-pentenal. The 2- and 3-pentenal are present in their cis and trans configuration. 3-Pentenal is represented by the following formula: 10 CH3-CH=CH-CH2-CH=O (I) [0016] It has been found that the pentenals should be prepared under strictly neutral conditions. With neutral con- ditions is meant neither acidic nor basic conditions. It has also been found that a pentenal containing mixture is pref- 15 erably stored at strictly neutral conditions. Performing the preparation and/or storage under acidic or basic conditions results in undesired side-reactions, like for example aldol condensation and isomerisation, resulting in the formation of undesired by-products. [0017] The hydroformylation reaction can be carried out batchwise, semi-continuously or continuously. [0018] In a preferred embodiment of the invention, the hydroformylation is performed in the presence of an alcohol 20 resulting in a reaction mixture comprising an acetal of pentenals. Hydroformylation of butadiene in the presence of an alcohol and a rhodium-phosphine complex catalyst is for example described in EP-A-94748, the complete disclosure of which is incorporated as reference. This disclosure do not mention or suggest to prepare a caprolactam precursor via acetals of pentenal. It has been found that the acetals of pentenal are easier to separate and/or to purify compared to the corresponding pentenals. It has also been found that the acetals of pentenal are less sensitive for the formation 25 of heavy by-products, for example formed through aldol condensation. Performing the hydroformylation in the presence of an alcohol will be referred to as acetalisation. Examples of suitable alcohols are monohydric alcohols and diols.
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