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Supported Catalyst, Preparation Method Therefor (19) TZZ¥Z _T (11) EP 3 056 269 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: B01J 27/138 (2006.01) B01J 37/22 (2006.01) 24.04.2019 Bulletin 2019/17 C07C 11/09 (2006.01) C07C 1/26 (2006.01) B01J 29/40 (2006.01) (21) Application number: 14859617.4 (86) International application number: (22) Date of filing: 28.10.2014 PCT/CN2014/089683 (87) International publication number: WO 2015/067133 (14.05.2015 Gazette 2015/19) (54) SUPPORTED CATALYST, PREPARATION METHOD THEREFOR AND USE THEREOF, AND METHOD FOR PREPARATION OF ISOBUTYLENE FROM HALOMETHANE GETRÄGERTER KATALYSATOR, HERSTELLUNGSVERFAHREN DAFÜR UND VERWENDUNG DAVON SOWIE VERFAHREN ZUR HERSTELLUNG VON ISOBUTYLEN AUS HALOMETHAN CATALYSEUR SUPPORTÉ, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION, ET PROCÉDÉ DE PRÉPARATION D’ISOBUTYLÈNE À PARTIR D’UN HALOMÉTHANE (84) Designated Contracting States: • ZHANG, Xiwen AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Fushun GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO Liaoning 113001 (CN) PL PT RO RS SE SI SK SM TR • SUN, Xiaodan Fushun (30) Priority: 07.11.2013 CN 201310546339 Liaoning 113001 (CN) • LI, Jie (43) Date of publication of application: Fushun 17.08.2016 Bulletin 2016/33 Liaoning 113001 (CN) • NI, Xiangqian (73) Proprietors: Fushun • China Petroleum & Chemical Corporation Liaoning 113001 (CN) Beijing 100728 (CN) • Fushun Research Institute of Petroleum and (74) Representative: Hoffmann Eitle Petrochemicals, Sinopec Corp. Patent- und Rechtsanwälte PartmbB Fushun, Liaoning 113001 (CN) Arabellastraße 30 81925 München (DE) (72) Inventors: • FANG, Xiangchen (56) References cited: Fushun EP-A1- 1 421 992 CN-A- 1 502 411 Liaoning 113001 (CN) CN-A- 86 107 833 CN-A- 101 342 494 • ZHANG, Shudong US-A- 4 091 038 US-A- 4 154 969 Fushun US-A1- 2009 163 749 Liaoning 113001 (CN) • ZHANG, Xinwei Fushun Liaoning 113001 (CN) 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 3 056 269 B1 Printed by Jouve, 75001 PARIS (FR) EP 3 056 269 B1 Description Field of the Invention 5 [0001] The present invention relates to a supported catalyst, method for its preparation and use thereof, and a method for preparation of isobutylene from halomethane by using this supported catalyst. Background of the Invention 10 [0002] Isobutylene is an important basic organic chemical raw material. It has numerous derivatives. Its upstream and downstream industrial chains are complex. Its consumption structure is in diversified trends. From isobutylene, many products with high added value may be prepared, such as: butyl rubber, polyisobutylene, methyl tertiary-butyl ether, isoprene, polymethyl methacrylate and many other organic chemical raw materials and fine chemical products. As the market size of isobutylene downstream products keeps expanding, the imbalance between supply and demand will get 15 more prominent. Particularly, under the background of increasing depletion of petroleum resources, the output of iso- butylene has become a critical bottleneck holding back the development of downstream industry. Therefore, it is urgent to develop an isobutylene preparation route rather than a petroleum route. [0003] Methane is a main component of natural gas, so methane conversion and utilization becomes an important research content of natural gas chemical technology. Particularly, in the recent years, under the general background of 20 shale gas development and utilization, if isobutylene can be made from methane, it will be a new way to obtain isobutylene. However, methane has stable properties and is not easily activated, so it turns to be a bottleneck of chemical utilization of methane. Many domestic and foreign researchers have carried out the research of methane activation and conversion. The technology of halogen functionalization and then conversion of methane hopefully will become an important break- through to the technical problem of methane conversion. 25 [0004] From halomethane, many chemical products may be prepared. CN101041609A and CN101284232A disclose a method of converting methane into bromomethane under the action of oxygen and HBr/H2O and then taking further reaction of bromomethane to generate C3∼C13 mixed high-carbon hydrocarbons. The selectivity of hydrocarbons of C 5 or higher is 70%. HBr is used to bromize methane in the first reactor and released in the second reactor. After recovery, it is used in the first reaction again to realize cyclic use of HBr. Wang Ye et al (Jieli He, Ting Xu, Zhihui Wang, et.al. 30 Angew.Chem. Int. Ed. 2012, 51,2438-2442) discloses amodified molecular sieve catalystof propylene from halomethane and preparation method thereof. By using a molecular sieve modified and treated with fluorinated compound to obtain an acidic catalyst containing an appropriate micropore structure, this catalyst may effectively catalyze halomethane and convert it into propylene. In the preparation and conversion of propylene from bromomethane, the single-pass bro- momethane conversion rate of the prepared catalyst is 35-99% and the selectivity of propylene is 27-70%; in the prep- 35 aration and conversion of propylene from chloromethane, the single-pass chloromethane conversion rate is 30-99% and the selectivity of propylene is 15-70%. Ivan M. Lorkovic et al (Ivan M. Lorkovic, Aysen Yilmaz, Gurkan A. Yilmaz, et al. Catalysis Today, 2004, 98, 317-322) also put forth a bromine circulation of using bromine to react with hydrocarbons in natural gas to generate bromo-hydrocarbons, then converting bromo-hydrocarbons into dimethyl ether, methanol and metal bromide on a metal oxide catalyst, and regenerating metal bromide by oxygen to obtain metal oxide and release 40 simple substance bromine. [0005] At present, the target products of halomethane conversion in the existing literature are methanol, dimethyl ether, acetic acid, high-carbon hydrocarbon, ethylene and propylene. In the technologies in which low-carbon olefins with high added value are target products, the selectivity of a single product is not high. So far there is no report on highly selective synthesis of isobutylene from bromomethane. 45 [0006] US 4,091,038 describes a process for producing dihydroxy diphenyl ethane which comprises reacting phenol with a 1,2-dihaloethane in which the halogen is chlorine, bromine or iodine in at least the stoichiometric proportions of 2/1 in contact with a zinc-containing catalyst at a temperature of from about 125 to 225°C and in the presence of iodine as promoter for the reaction. [0007] US 4,154,969 describes employing a combination of zinc oxide and zinc bromide as catalyst for the reaction 50 between phenol and a 1,2-dihaloethane. [0008] EP 1,421,992 discloses a method for producing a zinc chloride-loaded support in which zinc chloride is loaded on a solid support, comprising a step of bringing a mixture of the solid support and zinc oxide into contact with water vapor containing a hydrogen chloride gas or a hydrogen chloride gas so that said zinc oxide is chemically converted into zinc chloride. 55 [0009] US 2009/0163749 discloses a process for converting methane into higher hydrocarbons comprising contacting methane with a source of oxygen and hydrogen bromide to form one or more methane bromide compounds, in the presence of a first catalyst within a first reactor, converting the methane bromides into C 3-13 hydrocarbons and hydrogen bromide in the presence of a second catalyst within a second reactor. 2 EP 3 056 269 B1 Summary of the Invention [0010] To address the shortcomings of prior art, the present invention provides a supported catalyst for highly selective generation of isobutylene from halomethane and its preparation method and use. 5 [0011] According to one aspect of the present invention, the present invention provides a supported catalyst, wherein the catalyst contains a support and a metallic active component supported on the support; the metallic active component contains zinc oxide and zinc halide, and the content of zinc oxide is 0.5 wt.%-20 wt.%, the content of zinc halide is 10 wt.%-50 wt.%, and the content of the support is 40 wt.%-88 wt.% based on the total weight of the catalyst. [0012] According to the second aspect of the present invention, the present invention provides a method for preparing 10 a supported catalyst, wherein the method includes the steps as defined in the claims. According to the third aspect of the present invention, the present invention provides a use of the supported catalyst of the present invention in preparation of isobutylene. [0013] According to the fourth aspect of the present invention, the present invention provides a method for preparation of isobutylene from halomethane, wherein the method includes carrying out hydrogen reduction activation of the sup- 15 ported catalyst of the present invention to make the content of halogen in the activated catalyst be 20 wt.%-90 wt.% of the total content of halogen in the supported catalyst without reduction, then contacting halomethane with the activated catalyst to prepare isobutylene. Compared with prior art, the catalyst of the present invention may convert halomethane into isobutylene with high selectivity. The reaction for conversion and preparation of isobutylene from bromomethane is conducted by the method of the present invention. The bromomethane conversion rate is 90% or more and the selectivity 20 of isobutylene is 80% or more. The preparation method of this catalyst is simple and can be easily industrialized. The method for preparation and conversion of isobutylene from bromomethane in the present invention has such advantages as moderate reaction conditions and high product selectivity, can be easily industrialized and has a broad application prospect.
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