[go: up one dir, main page]

WO2015095997A1 - Procédé de préparation d'un composé polyoxyméthylène diméthyl éther carbonyle et de méthyl méthoxyacétate - Google Patents

Procédé de préparation d'un composé polyoxyméthylène diméthyl éther carbonyle et de méthyl méthoxyacétate Download PDF

Info

Publication number
WO2015095997A1
WO2015095997A1 PCT/CN2013/090214 CN2013090214W WO2015095997A1 WO 2015095997 A1 WO2015095997 A1 WO 2015095997A1 CN 2013090214 W CN2013090214 W CN 2013090214W WO 2015095997 A1 WO2015095997 A1 WO 2015095997A1
Authority
WO
WIPO (PCT)
Prior art keywords
reaction
dimethyl ether
raw material
carbon monoxide
hydrogen
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.)
Ceased
Application number
PCT/CN2013/090214
Other languages
English (en)
Chinese (zh)
Inventor
倪友明
朱文良
刘红超
刘勇
刘中民
孟霜鹤
李利娜
刘世平
周慧
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.)
Dalian Institute of Chemical Physics of CAS
Original Assignee
Dalian Institute of Chemical Physics of CAS
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 Dalian Institute of Chemical Physics of CAS filed Critical Dalian Institute of Chemical Physics of CAS
Priority to PCT/CN2013/090214 priority Critical patent/WO2015095997A1/fr
Publication of WO2015095997A1 publication Critical patent/WO2015095997A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
    • C07C67/37—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by reaction of ethers with carbon monoxide
    • 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
    • C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
    • C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
    • 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
    • C07C29/132—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 an oxygen containing functional group
    • C07C29/136—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 an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—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 an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C07C29/149—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 an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48—Preparation of compounds having groups
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Definitions

  • the present invention relates to a process for the preparation of polymethoxy dimethyl ether carbonyl and methyl methoxyacetate as intermediates for the production of ethylene glycol. Background technique
  • Ethylene glycol is an important chemical raw material and strategic material for the manufacture of polyester (which can be used to produce polyester, PET bottles, films), explosives, glyoxal, and as an antifreeze, plasticizer, hydraulic fluid and Solvents, etc.
  • China's ethylene glycol imports exceeded 5.8 million tons. It is estimated that China's ethylene glycol demand will reach 11.2 million tons in 2015, with a production capacity of about 5 million tons, and the supply and demand gap will still reach 6.2 million tons. Therefore, China's ethylene glycol production
  • Internationally, petroleum cracked ethylene is mainly oxidized to obtain epoxy acetamidine, and ethylene epoxide is hydrated to obtain ethylene glycol.
  • coal-based ethylene glycol new coal chemical technology can not only ensure the country's energy security, but also make full use of China's coal resources. It is the most realistic choice for the future coal chemical industry.
  • Polymethoxy dimethyl ether (or polymethoxy acetal, English name Polyoxymethylene dimethyl ethers) has the formula CH 3 0(C3 ⁇ 40) n CH 3 , where n 2 , generally referred to as DMM n (or PODE n :).
  • DMM n or PODE n :
  • DMM 3 ⁇ 4 can be used as a diesel additive.
  • the nature is low. Therefore, it is often necessary to repeatedly separate and re-react the by-products in the preparation process, so that the energy consumption is large and the economy is poor. Therefore, the direct processing of methylal and DMM 2 as by-products into products of higher economic value will increase the economics of this process.
  • An object of the present invention is to provide a process for producing polymethoxy dimethyl ether carbonyl and methyl methoxyacetate as an intermediate for producing ethylene glycol by carbonylation.
  • the present invention provides a process for preparing a polymethoxy dimethyl ether carbonyl compound as an intermediate for producing ethylene glycol by carbonylation, characterized in that the raw material polymethoxy dimethyl ether CH 3 0 ( CH 2 0) n CH 3 with the same carbon oxide and hydrogen passing through the reactor carrying the acidic resin catalyst, the reaction temperature is 60 ⁇ 140 ° C, the reaction pressure is 2 ⁇ 10 MPa, and the mass space velocity of polymethoxy dimethyl ether is 0.2 ⁇
  • the product polymethoxy dimethyl ether carbonyl is prepared by reacting 10.0 without adding other solvent, wherein under the reaction conditions, at least one of the raw material and the product is in a liquid phase, the acidic resin
  • the catalyst is a solid phase, carbon monoxide and hydrogen are in a gas phase such that the reaction process is a gas-liquid-solid three-phase reaction, and the molar ratio of carbon monoxide to the raw material is 2:1 to 20:1, and the molar ratio of hydrogen to the raw material is 1
  • the invention also provides a method for preparing methyl methoxyacetate and polymethoxy dimethyl ether carbonyl as an intermediate for producing ethylene glycol by carbonylation, characterized in that the raw material acetal CH 3 0- CH 2 -OCH 3 is connected to the same carbon oxide and hydrogen through a reactor carrying an acidic resin catalyst at a reaction temperature of 60 to: 140 ° C, a reaction pressure of 2 to: 10 MPa, and a mass space velocity of methylal of 0.2 to 10.0 h" 1 And preparing the product methyl methoxyacetate and polymethoxy dimethyl ether carbonyl by reacting without adding other solvent, wherein at least one of the raw material and the product is liquid under the reaction condition Phase, the acidic resin catalyst is a solid phase, carbon monoxide and hydrogen are in a gas phase to The reaction process is a gas-liquid-solid three-phase reaction, and the molar ratio of carbon monoxide to the raw material is 2:1 to 20:1, and the molar ratio of hydrogen to the raw material
  • the product polymethoxy dimethyl ether carbonyl is -0-C3 ⁇ 4-0- in the molecular chain of polymethoxy dimethyl ether CH 3 0(CH 2 0;) n CH 3
  • the polymethoxy dimethyl ether is dipoly methoxy dimethyl ether CH 3 0(C 3 ⁇ 40) 2 CH 3 .
  • the polymethoxy dimethyl ether carbonyl is one or more of the following:
  • the acidic resin catalyst is a perfluorosulfonic acid resin or a strong acid cation exchange resin.
  • the acidic resin catalyst is a Nafion resin.
  • the strongly acidic cation exchange resin is prepared by first copolymerizing styrene with divinylbenzene by sulfuric acid sulfonation and optionally F, C1 or Br modification.
  • the reaction temperature is 60 to 120 ° C
  • the reaction pressure is 4 to 10 MPa
  • the mass space velocity of the raw material is 0.5 to 3.0 h -
  • the molar ratio of carbon monoxide to the raw material is 2:1 ⁇ 15:1
  • the molar ratio of hydrogen to the raw material is 1:1 to 3:1.
  • the reaction temperature is 60 to 90 ° C
  • the reaction pressure is 5 to 10 MPa
  • the mass space velocity of the raw material is 0.5 to 1.5 h -
  • the molar ratio of carbon monoxide to the raw material is 2:1 ⁇ 10:1
  • the molar ratio of hydrogen to the raw material is 1:1 to 2:1.
  • the reactor is a fixed bed reactor, a tank reactor, a moving bed reactor or a fluidized bed reactor that effects a continuous reaction.
  • the conversion rate of the raw material polymethoxy dimethyl ether or methylal is high, the selectivity of each product is high, the catalyst has a long service life, no external solvent is needed, the reaction condition is mild, and the product can be continuously produced, and has industrial application. potential.
  • the obtained product can be hydrolyzed by hydrogenation Or hydrolyzed to produce ethylene glycol after hydrolysis.
  • the present invention provides a process for preparing a polymethoxy dimethyl ether carbonyl compound, characterized in that a raw material containing polymethoxy dimethyl ether CH 3 O CH 2 C n CH 3 , carbon monoxide and hydrogen is passed through an acid
  • the reactor of the resin catalyst is prepared by reacting at a reaction temperature of 60 to 140 ° C, a reaction pressure of 2 to 10 MPa, a mass space velocity of polymethoxy dimethyl ether of 0.2 to 10.0 h -1 and without adding other solvent.
  • Polymethoxy dimethyl ether carbonyl under the reaction conditions, the raw material polymethoxy dimethyl ether and the product polymethoxy dimethyl ether carbonyl are at least one liquid phase, the catalyst is a solid phase, and the raw materials carbon monoxide and hydrogen are gas phase.
  • the reaction process is a gas-liquid-solid three-phase reaction; in the raw material, the molar ratio of carbon monoxide to polymethoxy dimethyl ether is 2:1 ⁇ 20: 1, and the molar ratio of hydrogen to polymethoxy dimethyl ether is 1: 1 to 5: 1, where n 2 is an integer.
  • the acidic resin catalyst is a perfluorosulfonic acid resin (for example, Nafion resin) or a strongly acidic cation exchange resin.
  • the perfluorosulfonic acid resin is the strongest solid super acid currently known, and has the characteristics of good heat resistance, chemical stability and high mechanical strength.
  • a perfluorovinyl ether monomer having a sulfonic acid group is copolymerized with tetrafluoroethylene to obtain a perfluorosulfonic acid resin. Since the most electronegative fluorine atom is introduced into the Nafion resin, a strong field effect and an inducing effect are generated, so that its acidity increases sharply. Compared with liquid super acid, when used as a catalyst, it is easy to separate, can be used repeatedly, has low corrosivity, causes less pollution, has good selectivity, and is easy to be used in industrial production.
  • the strongly acidic cation exchange resin is a copolymer of styrene and divinylbenzene which is first sulfonated with sulfuric acid or not passed through? Preparation of halogen, Cl, Br and other halogen elements;
  • the highest use temperature of the strong acid cation exchange resin is higher than the reaction temperature, and the dry acid content is not less than 1 mmol/g.
  • the reaction process is a gas-liquid-solid three-phase reaction
  • the reaction temperature is 60 to: 120 ° C
  • the reaction pressure is 4 to 10 MPa
  • the mass space velocity of the polymethoxy dimethyl ether is 0.5 to 3.0 h.
  • the molar ratio of carbon monoxide to polymethoxy dimethyl ether is 2:1 to 15:1, and the preferred molar ratio of hydrogen to polymethoxy dimethyl ether is 1:1 to 3:1.
  • the reaction process is a gas-liquid-solid three-phase reaction
  • the reaction temperature is 60 to 90 ° C
  • the reaction pressure is 5 to: lO MPa
  • the mass space velocity of the polymethoxy dimethyl ether is 0.5 to 1.5.
  • h" 1 the molar ratio of carbon monoxide to polymethoxy dimethyl ether is 2:1 ⁇ 10:1
  • the preferred molar ratio of hydrogen to polymethoxy dimethyl ether is 1:1 ⁇ 2:1.
  • both the conversion of polymethoxy dimethyl ether and the selectivity of polymethoxy dimethyl ether carbonyl are calculated based on the moles of polymethoxy dimethyl ether carbon:
  • the invention also provides a preparation method of methyl methoxyacetate and polymethoxy dimethyl ether carbonyl, which comprises raw materials containing methylal CH 3 0-CH 2 -OCH 3 , carbon monoxide and hydrogen. passed through the reactor containing acidic resin catalyst, at a reaction temperature of 60 ⁇ 140 ° C, a reaction pressure of 2 ⁇ 10 MPa, WHSV methylal is 0.2 ⁇ 10.0 h "1 without adding any other solvent under the reaction conditions, the preparation of Methyl methoxyacetate and polymethoxy dimethyl ether carbonyl; under the reaction conditions, the raw material methyl acetal and the product methyl methoxyacetate and polymethoxy dimethyl ether carbonyl are at least one liquid phase, catalyst For the solid phase, the raw materials carbon monoxide and hydrogen are in the gas phase, and the reaction process is a gas-liquid solid three-phase reaction; in the raw material, the molar ratio of carbon monoxide to methylal is 2: 1 ⁇ 20: 1, and the m
  • the acidic resin catalyst is a strongly acidic perfluoro Nafion resin.
  • the reaction process is a gas-liquid-solid three-phase reaction
  • the reaction temperature is 60 to: 120 ° C
  • the reaction pressure is 4 to: 10 MPa
  • the mass space velocity of the methylal is 0.5 to 3.0 h - carbon monoxide and
  • the molar ratio of methylal is 2:1 to 15: 1, and the preferred molar ratio of hydrogen to methylal is 1:1 to 3:1.
  • the reaction process is a gas-liquid-solid three-phase reaction
  • the reaction temperature is 60 to 90 ° C
  • the reaction pressure is 5 to: 10 MPa
  • the mass space velocity of the methylal is 0.5 to 1.5 h - carbon monoxide and carbon
  • the molar ratio of acetal is 2:1 to 10:1
  • the preferred molar ratio of hydrogen to methylal is 1:1 to 2:1.
  • the conversion of methylal and the selectivity of the product are calculated based on the methylal number of methylal:
  • Methylal conversion [(Methyl acetal in the feed: M): (Met acetal carbon mole in the discharge) Number)] ⁇ (molar carbon in the feed) X (100%)
  • Methyl methoxyacetate selectivity (molar number of carbon after removal of carbonyl by methyl methoxyacetate in the discharge) ⁇ [(moles of methyl acetal in the feed) 1 (methyl acetal in the discharge) Number)] ⁇ ( ⁇ %)
  • Polymethoxy dimethyl ether carbonyl selectivity (Molar number of carbons after removal of carbonyl by polymethoxy dimethyl ether carbonyl in the discharge:) ⁇ [(in the feed) The number of moles of aldehyde carbon:) one (molar number of methyl acetal in the discharge)] X (100%)
  • the polymethoxy dimethyl ether carbonyl is in the molecular chain of polymethoxy dimethyl ether
  • the product of the -o-c3 ⁇ 4-(co)-o-structural unit, the polymethoxy dimethyl ether carbonyl compound contains one or more carbonyl groups.
  • the polymethoxy dimethyl ether carbonyl compound produced in the examples may be one or more of the following:
  • CH 3 -0-(CO) -CH 2 -0-CH 2 -0-CH 3 is abbreviated as C5-1,
  • CH 3 -0 -CH 2 -(CO)-0-CH 2 -0-CH 3 is abbreviated as C5-2,
  • CH 3 -0-(CO)-CH 2 -0-(CO)-CH 2 -0-CH 3 is abbreviated as C6-1,
  • CH 3 -0-(CO)-CH 2 -0-CH 2 -(CO)-0-CH 3 is abbreviated as C6-2.
  • the product of the present invention methyl methoxyacetate or polymethoxy dimethyl ether carbonyl, can be hydrolyzed by hydrogenation or hydrolyzed to obtain ethylene glycol. Further, the product can also be used as a steam and diesel additive.
  • the reaction process for the formation of ethylene glycol by diethylene dimethyl ether (DMM 2 ) CH 3 0(C3 ⁇ 40) 2 C3 ⁇ 4 is as follows:
  • the reactor is a continuous flow fixed bed reactor, a kettle Reactor, moving bed reactor or fluidized bed reactor.
  • the invention is described in detail below by way of examples, but the invention is not limited to the examples.
  • the reaction results are shown in Table 1.
  • Table 1 Catalytic reaction results of Buying Examples 1 to 8 and Comparative Examples 1 to 2
  • the reaction results are shown in Table 2.
  • T 120 °C
  • CO: DMM: H 2 15:1:4
  • P 4.7 MPa
  • WHSV 0.5 h - 1
  • the catalyst used in the process of the present invention is an acid resin catalyst
  • the raw material is polymethoxy dimethyl ether or methylal with a mixed gas of the same oxidized carbon and hydrogen.
  • the raw material can stably and efficiently produce the product polymethoxy dimethyl ether carbonyl or methyl methoxyacetate as an intermediate for producing ethylene glycol through the catalyst, and the reaction process is gas-liquid solid three-phase. reaction.
  • the carbonylation reaction of methoxy dimethyl ether or methylal is a strong exothermic reaction.
  • the reaction temperature is relatively low, and the liquid heat capacity and the latent heat of phase change are well, and the reaction temperature can be well controlled to prevent industrial production.
  • the gas-liquid-solid three-phase reaction adopted by the invention can be operated at a high concentration of polymethoxy dimethyl ether or methylal, which improves the single-pass reaction productivity in industrial production, and reduces the energy during compression, circulation and separation. Consumption, improve economic performance.
  • the conversion ratio of the raw material polymethoxy dimethyl ether or methylal is high, and the product polymethoxy dimethyl ether carbonyl or methyl methoxyacetate has high selectivity and long catalyst life.
  • the liquid phase starting material reactant or product itself is an excellent solvent, and no additional solvent is required.
  • the liquid phase reactant or product can dissolve the pre-carbon deposit material in the catalytic reaction process, which is beneficial to improving the activity and stability of the catalyst, the reaction condition is mild, the continuous production can be realized, and the industrial application potential is obtained.
  • a carbonylation reaction uses a mixed gas of carbon monoxide and hydrogen as a gas phase, and a high-purity carbon monoxide is required in comparison with the existing coal chemical production ethylene glycol technology.
  • the present invention does not require high-purity carbon monoxide, and can greatly reduce the separation gas of synthesis gas. Consumption, improve the economics of the production process.
  • the addition of hydrogen to the reaction gas can also increase the conversion of polymethoxy dimethyl ether or methylal and the selectivity of polymethoxy dimethyl ether carbonyl or methyl methoxyacetate to prolong the life of the catalyst.
  • polymethoxy dimethyl ether carbonyl or methyl methoxyacetate produced in the present invention can be produced by hydrohydrolysis or post-hydrolysis to produce ethylene glycol.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un procédé de préparation d'un composé polyoxyméthylène diméthyl éther carbonyle et/ou de méthyl méthoxyacétate servant d'intermédiaire pour produire de l'éthylène glycol, lequel procédé comprend les étapes consistant à : faire passer une substance brute polyoxyméthylène diméthyl éther ou diméthoxyméthane avec du monoxyde de carbone et de l'hydrogène gazeux à travers un réacteur renfermant un catalyseur à base de résine acide, et préparer des produits correspondants par réaction dans des conditions de réaction appropriées sans ajout d'autre solvant, le procédé de réaction étant une réaction en trois phases gaz-liquide-solide. Selon le procédé, le taux de conversion de la substance brute de olyoxyméthylène diméthyl éther ou diméthoxyméthane est élevé, la sélectivité des produits est élevée, la durée de vie utile du catalyseur est allongée, la nécessité d'un solvant supplémentaire est éliminée, les conditions de réaction sont relativement douces, une production en continu est autorisée et des possibilités d'application industrielle sont offertes. De plus, les produits obtenus peuvent soit être hydrogénés puis hydrolysés soit être hydrolysés puis hydrogénés pour produire de l'éthylène glycol.
PCT/CN2013/090214 2013-12-23 2013-12-23 Procédé de préparation d'un composé polyoxyméthylène diméthyl éther carbonyle et de méthyl méthoxyacétate Ceased WO2015095997A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/CN2013/090214 WO2015095997A1 (fr) 2013-12-23 2013-12-23 Procédé de préparation d'un composé polyoxyméthylène diméthyl éther carbonyle et de méthyl méthoxyacétate

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/CN2013/090214 WO2015095997A1 (fr) 2013-12-23 2013-12-23 Procédé de préparation d'un composé polyoxyméthylène diméthyl éther carbonyle et de méthyl méthoxyacétate

Publications (1)

Publication Number Publication Date
WO2015095997A1 true WO2015095997A1 (fr) 2015-07-02

Family

ID=53477280

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2013/090214 Ceased WO2015095997A1 (fr) 2013-12-23 2013-12-23 Procédé de préparation d'un composé polyoxyméthylène diméthyl éther carbonyle et de méthyl méthoxyacétate

Country Status (1)

Country Link
WO (1) WO2015095997A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114436845A (zh) * 2020-10-20 2022-05-06 中国石油化工股份有限公司 一种甲醛羰基化合成甲氧基乙酸甲酯的方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0078162A1 (fr) * 1981-10-23 1983-05-04 Toa Nenryo Kogyo Kabushiki Kaisha Procédé de production de méthoxyacétate de méthyle
CN102701977A (zh) * 2012-06-21 2012-10-03 东莞市同舟化工有限公司 一种甲氧基乙酸甲酯的连续合成方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0078162A1 (fr) * 1981-10-23 1983-05-04 Toa Nenryo Kogyo Kabushiki Kaisha Procédé de production de méthoxyacétate de méthyle
CN102701977A (zh) * 2012-06-21 2012-10-03 东莞市同舟化工有限公司 一种甲氧基乙酸甲酯的连续合成方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CELIK, FUAT E.: "Vapor-phase carbonylation of dimethoxymethane over H-Faujasite.", ANG CHEM. INT. ED., vol. 48, 31 December 2009 (2009-12-31), pages 4813 - 4815 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114436845A (zh) * 2020-10-20 2022-05-06 中国石油化工股份有限公司 一种甲醛羰基化合成甲氧基乙酸甲酯的方法
CN114436845B (zh) * 2020-10-20 2024-01-30 中国石油化工股份有限公司 一种甲醛羰基化合成甲氧基乙酸甲酯的方法

Similar Documents

Publication Publication Date Title
CN101768057B (zh) 聚甲醛二甲醚的合成方法
CN104725230B (zh) 制备聚甲氧基二甲醚羰化物及甲氧基乙酸甲酯的方法
WO2016150371A1 (fr) Dispositif de traitement et procédé de synthèse d'éther polyméthoxydiméthylique et désacidification
CN104725229B (zh) 制备聚甲氧基二甲醚羰化物及甲氧基乙酸甲酯的方法
KR20150056645A (ko) 사이클로헥사놀 및 알카놀을 동시생산하는 방법 및 장치
CN106349019B (zh) 一种生产环己醇的方法
CN104725224B (zh) 制备聚甲氧基二甲醚羰化物及甲氧基乙酸甲酯的方法
CN103360224A (zh) 一种制备聚甲氧基二甲醚的组合工艺
CN105622383A (zh) 一种丙烯酸的合成方法
CN104725225B (zh) 制备聚甲氧基二甲醚羰化物及甲氧基乙酸甲酯的方法
CN106220481A (zh) 一种连续生产聚甲醛二甲醚的工艺
CN103709019A (zh) 一种酸性离子液体催化合成低碳多醚类化合物的方法
WO2015096009A1 (fr) Procédé pour préparer un composé de polyoxyméthylène-diméthyléther-carbonyle et du méthoxyacétate de méthyle
CN104529783A (zh) 一种高效安全的氧化羰基合成碳酸酯的方法
WO2015095997A1 (fr) Procédé de préparation d'un composé polyoxyméthylène diméthyl éther carbonyle et de méthyl méthoxyacétate
CN102731305A (zh) 一种乙醇酸甲酯的制备方法
CN107118100A (zh) 一种一氧化碳深度偶联催化反应合成草酸酯的方法
CN110903181B (zh) 双催化体系制备对苯醌化合物的方法
CN106542977B (zh) 一种合成聚甲氧基二甲醚的方法
CN105272810A (zh) 一种分离乙烯/丙烯混合气体的方法
CN111097540A (zh) 合成乙醇酸甲酯的催化剂及其制备方法
CN100387338C (zh) 一种酯交换催化剂及其应用
WO2015095999A1 (fr) Procédé pour préparer un composé de polyoxyméthylène-diméthyléther-carbonyle et du méthoxyacétate de méthyle
CN101693646B (zh) 一种甘油氯化法制备二氯丙醇的方法
CN104449898B (zh) 一种车用醚类掺烧燃料及其制备方法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 13900433

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 13900433

Country of ref document: EP

Kind code of ref document: A1