WO2018157817A1 - Catalyseur d'hydrogénation sélective, son procédé de préparation et procédé d'évaluation pour la préparation catalytique d'alcool 2-méthylallyle - Google Patents

Catalyseur d'hydrogénation sélective, son procédé de préparation et procédé d'évaluation pour la préparation catalytique d'alcool 2-méthylallyle Download PDF

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Publication number
WO2018157817A1
WO2018157817A1 PCT/CN2018/077562 CN2018077562W WO2018157817A1 WO 2018157817 A1 WO2018157817 A1 WO 2018157817A1 CN 2018077562 W CN2018077562 W CN 2018077562W WO 2018157817 A1 WO2018157817 A1 WO 2018157817A1
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Prior art keywords
selective hydrogenation
hydrogenation catalyst
carrier
reaction
precious metal
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PCT/CN2018/077562
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English (en)
Chinese (zh)
Inventor
张然
王杰华
冯春峰
明卫星
杨伟光
苑颖
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武汉凯迪工程技术研究总院有限公司
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Publication of WO2018157817A1 publication Critical patent/WO2018157817A1/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/03—Catalysts comprising molecular sieves not having base-exchange properties
    • B01J29/0308—Mesoporous materials not having base exchange properties, e.g. Si-MCM-41
    • B01J29/0341—Mesoporous materials not having base exchange properties, e.g. Si-MCM-41 containing arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
    • C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
    • C07C29/153—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used
    • C07C29/156—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used containing iron group metals, platinum group metals or compounds thereof
    • C07C29/157—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases characterised by the catalyst used containing iron group metals, platinum group metals or compounds thereof containing platinum group metals or compounds thereof
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N31/00—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods
    • G01N31/10—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using catalysis
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
    • B01J2229/10—After treatment, characterised by the effect to be obtained
    • B01J2229/18—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself

Definitions

  • the selective hydrogenation of ⁇ , ⁇ -unsaturated aldehydes to unsaturated alcohols is one of the common synthetic steps in the fields of organic synthesis, fine chemicals, chemical medicine, etc., and the synthesis of a large number of fine chemicals, especially in the fields of perfumery, perfumery and pharmaceuticals. Both involve the selective reduction of unsaturated aldehyde groups.
  • 2-Methylallyl alcohol (commonly known as "carbon tetraol”) is a very important organic intermediate which can undergo self-polymerization and copolymerization. Methacrylic acid and esters can be prepared starting from 2-methylallyl alcohol. In addition, 2-methylallyl alcohol can also form an allyl ester with other organic acids.
  • Step 1 Weigh a part of the carrier in a beaker, and weigh another part of the carrier as a carrier for impregnation. Under stirring, deionized water is added to the beaker until the carrier in the beaker is just saturated, and the deionization is recorded.
  • Step 800 repeating the operations of steps 200-700 until the chromatographic analysis result of step 600 shows that the selective hydrogenation catalyst loses reactivity and the selectivity of the product 2-methylallyl alcohol, and the cycle of the selective hydrogenation catalyst is investigated. The number of times applied, that is, the life test.
  • Step 2 the precious metal precursor is dissolved in water, heated at 45 ⁇ 55 ° C for 0.5 ⁇ 2.0 hours until the precious metal precursor is completely dissolved, labeled as solution A;
  • the preparation method of the mesoporous silicon material SBA-15 is as follows:
  • the SBA-15 used in the present invention is prepared according to the preparation method provided by the reference (Science, 1998, 279 (5350): 548-552).
  • Polyoxyethylene ether-polyoxypropylene ether-polyoxyethylene ether (P123) was used as a template in the preparation process, and the average molecular weight was 5,800.
  • 0.25 g of P123, 0.55 g of TEOS, 1.3 ml of hydrochloric acid and 6.22 mL of deionized water were mixed, stirred at 30 ° C for 24 hours, and then the obtained product was transferred to a crystallization vessel and crystallized at 100 ° C. hour.
  • Step 4 Mix solution A and solution B uniformly, dilute to 4.0 mL with water, and mark as immersion liquid C.
  • the molar concentration of noble metal atoms in immersion liquid C is 0.015 mol/L, and the molar concentration of non-precious metal atoms is 0.01 mol/L. ;
  • the life test of the catalyst was carried out in a 50 mL batch reactor.
  • the 4% Ir-MoO 3 / SBA- 15 ( 0.1) catalyst and solvent water after one reaction were not taken out from the polytetrafluoro liner, and fresh 2-methylacrolein and the internal standard compound n-hexane were directly re-added.
  • the reactor was ventilated using high purity nitrogen, and the air in the reactor was removed, and the operation was repeated three times. Then switch to hydrogen to ventilate the reactor, replace the nitrogen, and repeat the operation three times.
  • the reactor was then charged with 2.0 MPa of hydrogen.
  • the reaction kettle was placed in a heating mantle to be heated to 60 ° C, and the reaction was stirred for 8 hours.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Immunology (AREA)
  • Pathology (AREA)
  • Molecular Biology (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Catalyseur d'hydrogénation sélective, son procédé de préparation et procédé d'évaluation pour la préparation catalytique d'alcool 2-méthylallyle. Le catalyseur d'hydrogénation sélective est constitué de deux parties, à savoir un support et un composant actif, selon lesquelles le composant actif comprend un matériau de métal précieux et un matériau métallique non précieux, et le support est un matériau de silicium mésoporeux, où le matériau de métal précieux est le métal précieux Ir, et le matériau de métal non précieux est l'un des métaux non précieux Mo, W, Ni et Co, et le rapport atomique du matériau de métal non précieux sur le matériau de métal précieux est de 0,1-1. Le catalyseur peut réduire catalytiquement un aldéhyde insaturé en un alcool insaturé dans des conditions de réaction relativement modérées et dans de l'eau.
PCT/CN2018/077562 2017-03-01 2018-02-28 Catalyseur d'hydrogénation sélective, son procédé de préparation et procédé d'évaluation pour la préparation catalytique d'alcool 2-méthylallyle WO2018157817A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201710117225.9A CN106902862A (zh) 2017-03-01 2017-03-01 选择性加氢催化剂和制备方法及其生成2‑甲基烯丙醇的催化评价方法
CN201710117225.9 2017-03-01

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WO2018157817A1 true WO2018157817A1 (fr) 2018-09-07

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WO (1) WO2018157817A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106902862A (zh) * 2017-03-01 2017-06-30 武汉凯迪工程技术研究总院有限公司 选择性加氢催化剂和制备方法及其生成2‑甲基烯丙醇的催化评价方法
CN106925267A (zh) * 2017-03-01 2017-07-07 武汉凯迪工程技术研究总院有限公司 选择性加氢催化剂和制备方法及其生成异丁醛的催化评价方法
CN109225316B (zh) * 2018-10-08 2020-03-31 中自环保科技股份有限公司 一种尾气处理催化剂及其制备方法和用途

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1275441A (zh) * 1999-05-26 2000-12-06 中国科学院大连化学物理研究所 一种α、β－不饱和醛选择加氢反应催化剂
US6294696B1 (en) * 1997-10-31 2001-09-25 Institut Francais Du Petrole Process for hydrogenating organic functions
CN101570469A (zh) * 2009-06-15 2009-11-04 上海华谊丙烯酸有限公司 一种由甲基丙烯醛加氢连续生产异丁醇的方法
CN102351667A (zh) * 2011-09-21 2012-02-15 上海华谊（集团）公司 一种甲基丙烯醛选择加氢制备异丁醛的方法
CN106582635A (zh) * 2016-12-08 2017-04-26 上海华谊（集团）公司 α、β不饱和醛选择加氢制不饱和醇的催化剂及其制备方法
CN106902862A (zh) * 2017-03-01 2017-06-30 武汉凯迪工程技术研究总院有限公司 选择性加氢催化剂和制备方法及其生成2‑甲基烯丙醇的催化评价方法
CN106925267A (zh) * 2017-03-01 2017-07-07 武汉凯迪工程技术研究总院有限公司 选择性加氢催化剂和制备方法及其生成异丁醛的催化评价方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120271076A1 (en) * 2010-02-05 2012-10-25 Soled Stuart L Iridium-Containing Catalysts, Their Production and Use
CN102614868B (zh) * 2012-02-22 2015-03-25 西安凯立化工有限公司 一种负载型贵金属加氢催化剂及其制备方法
CN105903488A (zh) * 2016-04-27 2016-08-31 武汉凯迪工程技术研究总院有限公司 用于生产生物柴油的选择性加氢催化剂及其制备方法和应用

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6294696B1 (en) * 1997-10-31 2001-09-25 Institut Francais Du Petrole Process for hydrogenating organic functions
CN1275441A (zh) * 1999-05-26 2000-12-06 中国科学院大连化学物理研究所 一种α、β－不饱和醛选择加氢反应催化剂
CN101570469A (zh) * 2009-06-15 2009-11-04 上海华谊丙烯酸有限公司 一种由甲基丙烯醛加氢连续生产异丁醇的方法
CN102351667A (zh) * 2011-09-21 2012-02-15 上海华谊（集团）公司 一种甲基丙烯醛选择加氢制备异丁醛的方法
CN106582635A (zh) * 2016-12-08 2017-04-26 上海华谊（集团）公司 α、β不饱和醛选择加氢制不饱和醇的催化剂及其制备方法
CN106902862A (zh) * 2017-03-01 2017-06-30 武汉凯迪工程技术研究总院有限公司 选择性加氢催化剂和制备方法及其生成2‑甲基烯丙醇的催化评价方法
CN106925267A (zh) * 2017-03-01 2017-07-07 武汉凯迪工程技术研究总院有限公司 选择性加氢催化剂和制备方法及其生成异丁醛的催化评价方法

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