CN107188795A - 一种低温催化氧化法制备糖二酸的方法 - Google Patents

一种低温催化氧化法制备糖二酸的方法 Download PDF

Info

Publication number
CN107188795A
CN107188795A CN201710411845.3A CN201710411845A CN107188795A CN 107188795 A CN107188795 A CN 107188795A CN 201710411845 A CN201710411845 A CN 201710411845A CN 107188795 A CN107188795 A CN 107188795A
Authority
CN
China
Prior art keywords
acid
catalyst
catalytic oxidation
low
reaction substrate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN201710411845.3A
Other languages
English (en)
Inventor
金鑫
闫昊
杨朝合
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
China University of Petroleum East China
Original Assignee
China University of Petroleum East China
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by China University of Petroleum East China filed Critical China University of Petroleum East China
Priority to CN201710411845.3A priority Critical patent/CN107188795A/zh
Publication of CN107188795A publication Critical patent/CN107188795A/zh
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
    • C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/42—Platinum
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
    • B01J23/44—Palladium
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
    • B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/56—Platinum group metals
    • B01J23/63—Platinum group metals with rare earths or actinides
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
    • B01J23/8906—Iron and noble metals
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
    • B01J23/8913—Cobalt and noble metals
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
    • B01J23/8926—Copper and noble metals
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
    • B01J23/8933—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/894—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with rare earths or actinides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

本发明公开了一种低温催化氧化法制备糖二酸的方法，步骤是(1)、金属催化剂、反应底物的摩尔比为1:200至1:5000；(2)、操作温度为20‑150；(3)、操作压力为1‑50个大气压的氧气压力；(4)、反应底物和溶剂的质量比为1:100到1:2；(5)、反应底物与催化剂的接触时间约为5‑50小时；(6)、工艺过程可以为间歇过程或连续过程；本发明具有制备工艺简单、方便，制备效果好，工作效率高等优点。

Description

一种低温催化氧化法制备糖二酸的方法
技术领域
本发明涉及的是一种低温催化氧化法制备糖二酸的方法。
背景技术
葡萄糖二酸(四羟基己二酸)是在植物和哺乳动物中早已发现的化合物。近年来，在美国国家再生能源研究所关于需要由生物物质制作的高附加值化学品的报告(非专利文献1)中举出了葡萄糖二酸作为前12名以内的化合物。在该报告中作为可以以葡萄糖二酸为原料制备出的葡萄糖二酸衍生物还示例出了葡糖二酸-γ-内酯、葡糖二酸-δ-内酯或葡糖二酸二内酯等内酯类(可期待其作为溶剂的用途)；多羟基聚酰胺类(可期待其作为新型尼龙的用途)等。此外，该报告中还推测可利用淀粉的硝酸氧化反应或碱性漂白剂存在下的催化氧化反应作为已知的葡萄糖二酸制造方法。
现有的糖二酸制备方法普遍存在比较复杂、制备困难等缺陷。
发明内容
本发明的目的在于针对现有技术的缺陷和不足，提供了一种低温催化氧化法制备糖二酸的方法。
为实现上述目的，本发明采用的技术方案是：
一种低温催化氧化法制备糖二酸的方法，其步骤是：
1.金属催化剂、反应底物的摩尔比为1:200至1:5000；
2.操作温度为20-150℃；
3.操作压力为1-50个大气压的氧气压力；
4.反应底物和溶剂的质量比为1:100到1:2；
5.反应底物与催化剂的接触时间约为5-50小时；
6.工艺过程可以为间歇过程或连续过程。
进一步，所述金属催化剂包括PtCu、PtCo、PtPd、PdCu、PdAu和AuCu双金属催化剂，还包括PtCuPd、PtCuPd、PtFePd、AuCuPd等三金属催化剂。
采用上述结构后，本发明的有益效果为：本发明具有制备工艺简单、方便，制备效果好，工作效率高等优点。
具体实施方式
为了使本发明的目的、技术方案及优点更加清楚明白，以下结合具体实施方式，对本发明进行进一步详细说明。应当理解，此处所描述的具体实施方式仅用以解释本发明，并不用于限定本发明。
一、葡萄糖酸氧化反应
表1.葡萄糖酸在Pt和Pd催化剂上氧化反应结果
括号内的数字为金属负载量，例如Pt(2)TiO2:2w％Pt含量，TiO2载体.反应条件:3.0g葡萄糖酸钠,1.00g of NaOH,H2O作为溶剂,总反应体积为50mL,1bar of O2压力,反应时间为6小时.GcA:葡萄糖二酸，TarA:甘油二酸,LA:乳酸,GlyA:甘油酸,GloA:乙醇酸,OxA:乙二酸。
表2.葡萄糖单酸在Pt和Pd催化剂上氧化反应结果
括号内的数字为金属负载量，例如Pt(2)TiO2:2w％Pt含量，TiO2载体.反应条件:3.0g葡萄糖酸钠,1.00g of NaOH,H2O作为溶剂,总反应体积为50mL,2bar of O2压力.GcA:葡萄糖二酸，TarA:甘油二酸,LA:乳酸,GlyA:甘油酸,GloA:乙醇酸,OxA:乙二酸。二、葡萄糖氧化转化
表3.葡萄糖在Pt和Pd等催化剂上氧化反应结果
括号内的数字为金属负载量，例如Pt(2)TiO2:2w％Pt含量，TiO2载体.反应条件:3.0g葡萄糖,1.50g of NaOH,H2O作为溶剂,总反应体积为50mL,2bar of O2压力.GcA:葡萄糖二酸，TarA:甘油二酸,LA:乳酸,GlyA:甘油酸,GloA:乙醇酸,OxA:乙二酸.
表4.葡萄糖在Pt、Pd和Au催化剂上氧化反应结果
括号内的数字为金属负载量，例如Pt(2)TiO2:2w％Pt含量，TiO2载体.反应条件:3.0g葡萄糖,1.50g of NaOH,H2O作为溶剂,总反应体积为50mL,2bar of O2压力.GcA:葡萄糖二酸，TarA:甘油二酸,LA:乳酸,GlyA:甘油酸,GloA:乙醇酸,OxA:乙二酸.
三、甘油氧化反应
表5.甘油在Pt和Pd催化剂上反应结果
Pt(2)TiO2:2w％Pt含量，TiO2载体.反应条件:3.0g甘油,1.00g of NaOH,H2O作为溶剂,总反应体积为50mL,1bar of O2压力.GcA:葡萄糖二酸，TarA:甘油二酸,LA:乳酸,GlyA:甘油酸,GloA:乙醇酸,OxA:乙二酸.
表6.甘油在Pt、Pd和Au催化剂上氧化反应结果
括号内的数字为金属负载量，例如Pt(2)TiO2:2w％Pt含量，TiO2载体.反应条件:3.0g甘油,1.50g of NaOH,H2O作为溶剂,总反应体积为50mL,2bar of O2压力.TarA:甘油二酸,LA:乳酸,GlyA:甘油酸,GloA:乙醇酸,OxA:乙二酸。
对于本领域技术人员而言，显然本发明不限于上述示范性实施例的细节，而且在不背离本发明的精神或基本特征的情况下，能够以其他的具体形式实现本发明。因此，无论从哪一点来看，均应将实施例看作是示范性的，而且是非限制性的，本发明的范围由所附权利要求而不是上述说明限定，因此旨在将落在权利要求的等同要件的含义和范围内的所有变化囊括在本发明内。
此外，应当理解，虽然本说明书按照实施方式加以描述，但并非每个实施方式仅包含一个独立的技术方案，说明书的这种叙述方式仅仅是为清楚起见，本领域技术人员应当将说明书作为一个整体，各实施例中的技术方案也可以经适当组合，形成本领域技术人员可以理解的其他实施方式。

Claims (2)

1.一种低温催化氧化法制备糖二酸的方法，其特征在于：步骤是：
(1)、金属催化剂、反应底物的摩尔比为1:200至1:5000；
(2)、操作温度为20-150℃；
(3)、操作压力为1-50个大气压的氧气压力；
(4)、反应底物和溶剂的质量比为1:100到1:2；
(5)、反应底物与催化剂的接触时间约为5-50小时；
(6)、工艺过程可以为间歇过程或连续过程。
2.根据权利要求1所述的一种低温催化氧化法制备糖二酸的方法，其特征在于：所述金属催化剂包括PtCu、PtCo、PtPd、PdCu、PdAu和AuCu双金属催化剂，还包括PtCuPd、PtCuPd、PtFePd、AuCuPd等三金属催化剂。
CN201710411845.3A 2017-06-05 2017-06-05 一种低温催化氧化法制备糖二酸的方法 Pending CN107188795A (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201710411845.3A CN107188795A (zh) 2017-06-05 2017-06-05 一种低温催化氧化法制备糖二酸的方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201710411845.3A CN107188795A (zh) 2017-06-05 2017-06-05 一种低温催化氧化法制备糖二酸的方法

Publications (1)

Publication Number Publication Date
CN107188795A true CN107188795A (zh) 2017-09-22

Family

ID=59877044

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201710411845.3A Pending CN107188795A (zh) 2017-06-05 2017-06-05 一种低温催化氧化法制备糖二酸的方法

Country Status (1)

Country Link
CN (1) CN107188795A (zh)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108383717A (zh) * 2018-04-18 2018-08-10 中国石油大学(华东) 一种生物质基丙二酸的制备方法
CN113493379A (zh) * 2020-04-03 2021-10-12 山东惠生堂生物医药有限公司 葡萄糖二酸钙的制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101486639A (zh) * 2009-02-18 2009-07-22 南京林业大学 一种混合葡萄糖衍生物的新型合成方法
CN102971074A (zh) * 2010-06-11 2013-03-13 莱诺维亚公司 包括铂和金纳米颗粒的催化剂和其用于氧化葡萄糖的用途以及此催化剂的制备方法
CN105777535A (zh) * 2014-08-18 2016-07-20 现代自动车株式会社 用于制备葡糖二酸的方法
EP3088377A1 (en) * 2015-04-30 2016-11-02 Rhodia Operations Process for the preparation of an aldaric acid or a salt thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101486639A (zh) * 2009-02-18 2009-07-22 南京林业大学 一种混合葡萄糖衍生物的新型合成方法
CN102971074A (zh) * 2010-06-11 2013-03-13 莱诺维亚公司 包括铂和金纳米颗粒的催化剂和其用于氧化葡萄糖的用途以及此催化剂的制备方法
CN105777535A (zh) * 2014-08-18 2016-07-20 现代自动车株式会社 用于制备葡糖二酸的方法
EP3088377A1 (en) * 2015-04-30 2016-11-02 Rhodia Operations Process for the preparation of an aldaric acid or a salt thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
XIN JIN，ET AL: "Exceptional performance of bimetallic Pt1Cu3/TiO2 nanocatalysts for oxidation of gluconic acid and glucose with O2 to glucaric acid", 《JOURNAL OF CATALYSIS》 *
王珊珊等: "碳纳米管负载铂高效催化葡萄糖氧化制葡萄糖二酸", 《中国科技论文在线》 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108383717A (zh) * 2018-04-18 2018-08-10 中国石油大学(华东) 一种生物质基丙二酸的制备方法
CN108383717B (zh) * 2018-04-18 2021-05-11 中国石油大学(华东) 一种生物质基丙二酸的制备方法
CN113493379A (zh) * 2020-04-03 2021-10-12 山东惠生堂生物医药有限公司 葡萄糖二酸钙的制备方法

Similar Documents

Publication Publication Date Title
Cattaneo et al. Gold catalysts for the selective oxidation of biomass‐derived products
Villa et al. Glycerol oxidation using gold-containing catalysts
Wojcieszak et al. Advances in base-free oxidation of bio-based compounds on supported gold catalysts
Besson et al. Conversion of biomass into chemicals over metal catalysts
Derrien et al. Aerobic oxidation of glucose to glucaric acid under alkaline-free conditions: Au-based bimetallic catalysts and the effect of residues in a hemicellulose hydrolysate
EP2322275B1 (en) Tungsten carbide catalyst, its preparation method and its use in obtaining ethylene glycol by cellulose
Sankar et al. Oxidation of glycerol to glycolate by using supported gold and palladium nanoparticles
Hirasawa et al. Selective oxidation of glycerol to dihydroxyacetone over a Pd–Ag catalyst
CN102527377B (zh) 一种浸渍-可控还原法制备的CO羰化制草酸酯用高效纳米Pd催化剂
Qu et al. Hydrogenation of carboxylic acids, esters, and related compounds over heterogeneous catalysts: a step toward sustainable and carbon-neutral processes
Ryabenkova et al. The selective oxidation of 1, 2-propanediol by supported gold-based nanoparticulate catalysts
Villa et al. Bismuth modified Au-Pt bimetallic catalysts for dihydroxyacetone production
CN102617519B (zh) 由乙酰丙酸加氢制备γ-戊内酯的方法
Arcanjo et al. Glycerol valorization: Conversion to lactic acid by heterogeneous catalysis and separation by ion exchange chromatography
US20140179950A1 (en) Method of making adipic acid using nano catalyst
CN103055851A (zh) 一种co气相氧化偶联合成草酸酯的催化剂及其制备和应用方法
CN102249892B (zh) 一种1,2-丙二醇催化氧化制备乳酸的方法
CN107188795A (zh) 一种低温催化氧化法制备糖二酸的方法
Mimura et al. Liquid phase oxidation of glycerol in batch and flow-type reactors with oxygen over Au–Pd nanoparticles stabilized in anion-exchange resin
CN109422632B (zh) 一种催化氧化异戊烯醇制异戊烯醛的方法
Machado et al. Catalysts and processes for gluconic and glucaric acids production: A comprehensive review of market and chemical routes
CN108191635B (zh) 一种催化氧化制备葡萄糖酸的方法
JPH04356436A (ja) カルボニル化合物の製造方法
KR102526165B1 (ko) 아디프산 제조용 스피넬 구조 촉매 및 그를 이용한 아디프산의 제조방법
CN106807366B (zh) 甘油制取乳酸和丙酮酸的核壳型催化剂及其制备和应用

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
RJ01 Rejection of invention patent application after publication
RJ01 Rejection of invention patent application after publication

Application publication date: 20170922