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United States Patent (19) 11 Patent Number: 5,877,358 Garton Et Al

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United States Patent (19) 11 Patent Number: 5,877,358 Garton Et Al USOO5877358A United States Patent (19) 11 Patent Number: 5,877,358 Garton et al. (45) Date of Patent: Mar. 2, 1999 54 ALCOHOL HYDROGENATION WITH Primary Examiner José G. Dees INTERMEDIATE RECYCLE ASSistant Examiner Barbara Badio Attorney, Agent, or Firm John F. Hunt; Andrew B. Griffis 75 Inventors: Ronald D. Garton; Donald Q. Brown; Magdiel Agosto, all of Baton Rouge, 57 ABSTRACT La. In the process of hydrogenating a crude aldehyde product 73 Assignee: Exxon Chemical Patents Inc., formed from the OXO process into a crude alcohol product, Houston, TeX. which process includes: feeding the crude aldehyde product into a first reactor which contains a hydrogenation catalyst, 21 Appl. No.:717,980 thereby forming a first hydrogenated product; feeding the 9 first hydrogenated product from the first reactor through at 22 Filed: Sep. 23, 1996 least one intermediate reactor, each intermediate reactor 6 being connected in Series and containing a hydrogenation 51) Int. Cl. ..................................................... C07C 29/14 catalyst, thereby forming at least one intermediate hydroge 52) U.S. Cl. .............................................................. 568/882 nated product; and feeding the intermediate hydrogenated 58 Field of Search ..................................... 568/881, 814, product from a last intermediate reactor to a final reactor 568/862, 882 which contains a hydrogenation catalyst, thereby forming the crude alcohol product; the improvement including a step 56) References Cited wherein: at least a portion of the first hydrogenated product U.S. PATENT DOCUMENTS is recycled to the first hydrogenation reactor; or at least a portion of the intermediate hydrogenated product is recycled 4,426,541 1/1984 King - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - 568/881 tO the first hydrogenation reactOr Or an intermediate reactOr 4,451,677 5/1984 Bradley et al. ......................... 568/881 upstream of the intermediate reactor from which the inter 4,658,068 4/1987 Hanin. mediate hydrogenated product is removed. 4,960,960 10/1990 Harrison et al. ........................ 568/881 5,030,774 7/1991 Oswald et al. .......................... 562/885 5,093,535 3/1992 Harrison et al.. 13 Claims, 3 Drawing Sheets U.S. Patent Mar. 2, 1999 Sheet 1 of 3 5,877,358 s U.S. Patent Mar. 2, 1999 Sheet 2 of 3 5,877,358 SD 3. 2 D & 2 D U.S. Patent Mar. 2, 1999 Sheet 3 of 3 5,877,358 5,877,358 1 2 ALCOHOL HYDROGENATION WITH be obtained by recycling the output of one or more of the INTERMEDIATE RECYCLE Serially connected hydrogenation tank reactors back to the crude OXO aldehyde feedstream or, optionally, into a hydro The present invention relates generally to the production genation tank reactor connected in Series with and preceding of oxo alcohols from a crude hydroformylation aldehyde the hydrogenation tank reactor from which the recycle product. In particular, it relates to the recycle of alcohol Stream is taken. hydrogenation intermediates to enhance the yield and qual Other and further objects, advantages and features of the ity of OXO alcohols produced. present invention will be understood by reference to the following Specification in conjunction with the annexed BACKGROUND OF THE INVENTION drawings. Hydroformylation reactions involve the preparation of oxygenated organic compounds by the reaction of carbon SUMMARY OF THE INVENTION monoxide and hydrogen (Synthesis gas) with carbon com A proceSS is disclosed for hydrogenating a crude oxo pounds containing olefinic unsaturation. The reaction is aldehyde product formed by the hydroformylation of an typically performed in the presence of a carbonylation 15 olefinic feedstock with Synthesis gas in the presence of a catalyst and results in the formation of compounds, for catalyst, which includes the following Steps: feeding the example, aldehydes, which have one or more carbon atoms crude OXO aldehyde product and/or a recycled partially in their molecular structure than the Starting olefinic feed hydrogenated product to a first hydrogenation reactor Stock. By way of example, higher alcohols may be produced wherein the crude OXO aldehyde product is converted to a in the so-called “oxo” process by hydroformylation of first partially hydrogenated product; feeding the first par commercial Cs to C olefin fractions to an aldehyde tially hydrogenated product from the first hydrogenation containing OXonation product, which on hydrogenation reactor to a Second hydrogenation reactor wherein the first yields the corresponding C to Ca Saturated alcohols. The partially hydrogenated product is converted to a Second OXO process is the commercial application of the hydro partially hydrogenated product; and feeding at least part of formylation reaction for making higher aldehydes and alco 25 the Second partially hydrogenated product from the Second hols from olefins. The crude product of the hydroformyla hydrogenation reactor to the crude OXO aldehyde product tion reaction will typically contain catalyst, aldehydes, upstream of the first hydrogenation reactor, which proceSS alcohols, unreacted olefin feed, Synthesis gas and generates an OXO alcohol product having higher yield and by-products. quality than a process that does not recycle partially hydro The OXO process is well known in the art and is generally genated product. described in detail in Kirk-Other, Encyclopedia of Chemical In this process, the first partially hydrogenated product Technology, Volume 16, 3rd edition, John Wiley & Sons, pp. may be fed from the first hydrogenation reactor to the Second 637-53, 1981. The teachings of U.S. Pat. No. 5,237,105 to hydrogenation reactor via at least one intermediate hydro Summerlin in regard to the OXO proceSS are also incorporated genation reactor, or part of the Second hydrogenated product herein by reference. 35 may be fed from the Second hydrogenation reactor to at least Prior to the hydrogenation Step, the crude product of the one downstream hydrogenation reactor. OXO proceSS is generally treated to remove the dissolved Degassing Steps for degassing the liquid hydrogenation cobalt catalyst, which for reasons of economy may be product and exhausting the gas from the System prior to recycled to the OXO reactor. 40 recycling the liquid hydrogenation product with the crude “Demetalled” hydroformylation reaction product or crude OXO aldehyde product are also disclosed. In this process, the OXO aldehyde product is the reaction product which is catalyst is a Sulfided catalyst Selected from the group con Substantially depleted of the transition metal cobalt catalyst sisting of NiMo, CoMo, NiCoMo, Mo and mixtures thereof, required for the hydroformylation reaction. Such crude oxo and may further include a carbonaceous Support. The ratio of aldehyde product will generally contain cobalt in an amount 45 the recycled Second partially hydrogenated product to the of from about 0.05 to 3.0 wt.%, calculated as elemental aldehyde product is approximately 10:1, more preferably cobalt. The concentration of aldehyde in the crude oxo 3:1. aldehyde product is generally from about 40 to 90 wt.%. The additional Step of feeding the crude OXO alcohol The next Step in the OXO proceSS is the hydrogenation of product into a Subsequent plug flow reactor to produce a the crude OXO aldehyde product which is typically carried 50 high yield crude OXO alcohol product is also disclosed. out in the presence of hydrogen and at pressures of about A related proceSS is also disclosed for hydrogenating a 6.89 MPa to 31.00 MPa (1000 to 4500 psig) using a crude oxo aldehyde product formed by the hydroformylation hydrogenation catalyst. of an olefinic feedstock with Synthesis gas in the presence of The crude product of the OXO proceSS is recovered then a catalyst, which includes the following Steps: feeding the and, optionally, treated by known means to hydrogenate the 55 crude OXO aldehyde product to a first hydrogenation reactor aldehydes to form additional quantities of the corresponding wherein the crude OXO aldehyde product is converted to a OXO alcohols. These OXO alcohols, in turn, are widely used as first partially hydrogenated product; feeding the first par chemical intermediates in the manufacture of plasticizers, tially hydrogenated product from the first hydrogenation detergents, Solvents and the like. reactor to a Second hydrogenation reactor wherein the first The present inventors have developed a unique proceSS 60 partially hydrogenated product is converted to a Second which is capable of producing a higher yield of alcohols, as partially hydrogenated product; feeding the Second partially well as minimizing the amount of acid byproducts and dimer hydrogenated product from the Second hydrogenation reac materials produced during the hydrogenation of OXO alde tor to a third hydrogenation reactor wherein the Second hydes. The present inventors have discovered that when partially hydrogenated product is converted to a third par hydrogenation is performed on a Sulfided molybdenum 65 tially hydrogenated product; and feeding at least part of the based catalyst such as NiMo, CoMo, NiCoMo, Mo and third partially hydrogenated product from the third hydro mixtures thereof, a higher yield and quality of alcohols can genation reactor to the first hydrogenated product Stream 5,877,358 3 4 upstream of the third hydrogenation reactor, which proceSS gen in the form of H is also fed into conduit 19. Reactor generates an OXO alcohol product having higher yield and tank 11 contains a sulfided bimetallic
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