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(12) Patent Application Publication (10) Pub. No.: US 2011/0313220 A1 Mamedov Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2011/0313220 A1 Mamedov Et Al US 2011 0313220A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2011/0313220 A1 MamedOV et al. (43) Pub. Date: Dec. 22, 2011 (54) SELECTIVE CATALYTIC HYDROGENATION (30) Foreign Application Priority Data OFALKYNES TO CORRESPONDING ALKENES Dec. 18, 2008 (EP) .................................. O8021964.5 (75) Inventors: Aggadin Kh Mamedov, Sugar Publication Classification Land, TX (US); Saeed Mohammed (51) Int. Cl. Al-Wahabi, Riyadh (SA) C07C 5/05 (2006.01) BOI 2L/02 (2006.01) (73) Assignee: SAUD BASIC INDUSTRIES (52) U.S. Cl. .......... 585/274; 585/271; 502/207: 502/204 CORPORATION, Riyadh (SA) (57) ABSTRACT (21) Appl. No.: 13/140,881 The invention relates to a process for selectively hydrogenat ing an alkyne to the corresponding alkene comprising a step (22) PCT Filed: Dec. 15, 2009 of contacting a gaseous feed comprising hydrogen and 0.1 to 20 mass % of alkyne with a catalyst comprising at least one (86). PCT No.: PCT/EP2009/008962 Group 10 element on a boron-modified support. The process shows high conversion and good selectivity, and can be stably S371 (c)(1), operated also if the feed comprises more than 2 mass % of (2), (4) Date: Sep. 12, 2011 alkyne. US 2011/0313220 A1 Dec. 22, 2011 SELECTIVE CATALYTIC HYDROGENATION presence of hydrogen over a Supported catalyst that have been OFALKYNES TO CORRESPONDING surface modified with Pd and another metal from group IB, ALKENES Such as Ag, and optionally an alkaline or alkaline earth metal. Selective hydrogenation of acetylene is typically carried out CROSS REFERENCE TO RELATED on a feed containing 98% ethylene and 2% acetylene at a APPLICATIONS space velocity of 3300 h". 0007. In U.S. Pat. No. 6,350,717 B1 a catalyst comprising 0001. This application is a 371 of International Applica at least one Group 10 and at least one Group 11 metal in tion No. PCT/EP2009/008962, filed Dec. 15, 2009, which specific ratios on an alumina Support is described, wherein the claims priority to European Application No. 08021964.5.5, Group 10 metals are concentrated in a surface layer of the filed Dec. 18, 2008, both of which are hereby incorporated by Support. The catalyst were used in hydrogenating acetylene in reference in its entirety. a 1/99 mixture with ethylene. 0008 WO03/106020 describes modification of a sup TECHNICAL FIELD ported Pd Ag catalyst with an iodide compound, to improve 0002 The invention relates to a process for selective performance in hydrogenating acetylene in a mixed feed hydrogenation of an alkyne to the corresponding alkene com stream containing up to about 1.5 mass of acetylene. prising a step of contacting a gaseous feed comprising hydro 0009 U.S. Pat. No. 7,153,807B2 discloses supported gen and alkyne with a Supported Group 10 metal catalyst. Ni or Pt catalyst further comprising at least two other elements selected from Groups 8-9 and Groups 11-12, which BACKGROUND show better hydrogenation selectivity on feed streams com 0003. Such a process is known from WO2006/105799. prising up to about 2 mass % of acetylene This document discloses a method for selective hydrogena (0010 U.S. Pat. No. 4,906,800 discloses a process for tion of acetylene to ethylene wherein a feed comprising acety selectively converting a feed stream containing acetylene, lene and hydrogen is contacted with a TiO, Supported Group ethylene and hydrogen into gasoline range hydrocarbons, 10 metal catalyst in a fixed bed reactor, and wherein the wherein acetylene is hydrogenated by contacting with a catalyst is diluted with a linert solid like SiO, ZrO, Al-O or Pd Pb/CaCO catalyst that is made by a process including TiO, preferably at a weight ratio of diluent to supported specific oxidizing/reducing pre-treatment steps. Such a cata catalyst of from about 50 to about 170. The catalyst is lyst would be Suited for treating feed mixtures containing reported to be suitable for converting acetylene in a gas relatively high amounts of acetylene, like a pyrolysis effluent stream that contains up to 20 mass % of acetylene. gas; exemplified by an experiment on a stream containing 2.6 0004 Selective hydrogenation of alkynes to the corre mass % of acetylene. sponding alkenes is industrially important. Numerous docu 0011 EP0689872A1 discloses a catalyst comprising pal ments focus on processes to remove acetylenic impurities, ladium, silver and a Support material useful in a process for typically present in concentrations of 0.5-1 mol %, from selective acetylene hydrogenation. Prior to use, the catalyst is ethylene. contacted with a liquid reducing agent which interalia may be 0005 Ethylene is a major intermediate for various chemi boronhydride. cals, for example as a monomer that is used for the prepara (0012 WO02/16032 discloses a process for selective tion of a large number of polymers. Ethylene is generally acetylene hydrogenation using a catalyst comprising an inor obtained by a hydrocarbon pyrolysis or steam cracking pro ganic Support material, a palladium component, a silver com cess, followed by separation steps. Polymer grade ethylene ponent and a promoter component "XYF, wherein said needs to be of high purity, and maximum allowable acetylene promoter component is a fluorine-comprising compound fur level is about 10 or even 5 ppm. One of the techniques used to ther consisting of an alkaline metal element and a further free ethylene from any acetylene impurities is to selectively element which interalia may be boron. hydrogenate acetylene to ethylene over a palladium based 0013 There remains a need in industry of a catalyst sys catalyst Supported on a suitable Support Such as alumina. A tem showing high activity and selectivity, and good stability general problem with Such metal based catalysts is that when in hydrogenating alkynes in mixed feeds, also in feeds con the operating conditions are such as to permit complete elimi taining relatively high amounts of alkynes. nation of the acetylene, a proportion of ethylene is also hydro genated and converted to ethane. In addition, these single SUMMARY metal catalysts generally have relatively low stabilities due to 0014. The object of the invention is therefore to provide the formation of a large amounts of oligomers formed, often Such a selective catalytic hydrogenation process for hydroge referred to as green oil, which gradually cover the catalyst nating alkynes in mixed feeds. Surface under operating conditions, thereby requiring fre 0015 The objective is achieved according to the invention quent regeneration of the catalyst by Some controlled oxida as defined in the Claims, especially with a process for selec tion process. A further disadvantage is that Such catalyst may tively hydrogenating an alkyne to the corresponding alkene be quickly deactivated if used to hydrogenate acetylene in comprising a step of contacting a gaseous feed comprising feed streams that contain relatively high amounts of acety hydrogen and 0.1-20 mass % of alkyne with a catalyst com lene, that is up to 10 or even 20 mass %. prising at least one Group 10 element on a boron-modified 0006. Several other documents also address improving the Support. performance of esp. Pd-based supported catalysts in hydro genation of alkynes like acetylene. For example U.S. Pat. No. DETAILED DESCRIPTION 5,648,576 discloses a process for selective hydrogenation in the gas phase of acetylene compounds containing 2 or 3 0016. In the context of the present invention, the term carbon atoms to the corresponding ethylene compounds in "element on a boron-modified support” is meant to describe US 2011/0313220 A1 Dec. 22, 2011 that the element is deposited on a Support that was modified operating the process according to the invention, the feed has with boron prior to the deposition of said element on the been obtained by thermal pyrolysis of a hydrocarbon like Support. Accordingly, a “catalyst comprising at least one methane. Group 10 element on a boron-modified support as employed 0022. The gaseous feed used in the process according to in the process of the present invention represents a catalyst the invention contains hydrogen and alkyne, which may be which is characterized in that at least one Group 10 element is present in widely varying amounts, for example in a molar deposited on a boron-modified Support. ratio of from 0.5 to 10. It is an advantage that the process can be operated with high hydrogen concentrations without nega 0017 Surprisingly, the process of present invention allows tively affecting selectivity. Preferably, the feed contains more selective hydrogenation of an alkyne like acetylene in to an hydrogen than is stoichiometrically required for completing alkene, eg ethylene, with higher conversion, and the catalyst the hydrogenation reaction, that is the molar ratio of hydrogen showing better stability than prior art processes using cata to alkyne is preferably at least 1.0, 1.1 or 1.2, and at most 8, 6. lysts without a boron-modified support. The catalyst shows 5, 4, or 3. high activity, enabling relatively short contact times, i.e. high 0023 The inventors surprisingly found that the catalyst space velocities, also referred to as GHSV, which enables applied in the process according to the invention shows said integration of the process with other known processes such as advantageous performance if a suitable Support if first modi methane reforming or methane pyrolysis generally used for fied with a boron compound, and then with the Group 10 ethylene synthesis, with typically only very short contact metal. Preferably, the support is surface modified with boron, times and thus high flow rates. It is a further advantage of the more preferably predominantly the surface of the support is process of the present invention that the activity of the inven modified.
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