WO2013168113A1 - Procédé de préparation d'alcoxydes de métaux alcalins - Google Patents

Procédé de préparation d'alcoxydes de métaux alcalins Download PDF

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Publication number
WO2013168113A1
WO2013168113A1 PCT/IB2013/053730 IB2013053730W WO2013168113A1 WO 2013168113 A1 WO2013168113 A1 WO 2013168113A1 IB 2013053730 W IB2013053730 W IB 2013053730W WO 2013168113 A1 WO2013168113 A1 WO 2013168113A1
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WO
WIPO (PCT)
Prior art keywords
column
alkali metal
alcohol
distillation column
reactive distillation
Prior art date
Application number
PCT/IB2013/053730
Other languages
English (en)
Inventor
Clarisa MOCCIARO
Carlos H. MENDIONDO
Gabriel I. HOROWITZ
Rodolfo R. CARLEVARIS
Horacio ABADIAS
Original Assignee
Ypf Sociedad Anonima
Invap S.E.
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 Ypf Sociedad Anonima, Invap S.E. filed Critical Ypf Sociedad Anonima
Publication of WO2013168113A1 publication Critical patent/WO2013168113A1/fr

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Classifications

    • 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
    • C07C29/68—Preparation of metal alcoholates
    • C07C29/70—Preparation of metal alcoholates by converting hydroxy groups to O-metal 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
    • Y02P20/10—Process efficiency

Definitions

  • the present invention relates to the preparation of alkali metal alkoxides starting from alcohols and hydroxides of corresponding alkali metals.
  • metal alkoxide is used to designate chemical compounds in which a metal is bonded to one or more alkyl groups by an oxygen atom.
  • alkali metal alkoxide refers to a metal alkoxide where the metal is a metal of the group of alkali metals.
  • Metal alkoxides may be used for a variety of applications. They are useful for obtaining metals in organic solutions, for example in a homogeneous catalytic reaction. Compared to other inorganic metal compounds such as metal carboxylates , alcoxides are advantageous due to their catalytic properties, ease of hydrolysis, solubility in organic solvents and are easily distillable.
  • alkali metal alkoxides hereinafter called simply "alkoxides” are mainly used in the synthesis of numerous organic compounds, where they act as strong bases.
  • Alkali metal alkoxides may be obtained by various processes. In particular, they can be produced from the reaction between an alkali metal hydroxide (MOH) and an alcohol (ROH) . Said reaction can be written
  • This reaction is usually an equilibrium reaction, whereby the produced water must be removed by physical or chemical processes so as to displace the equilibrium reaction towards the production of products .
  • U.S. patent 7,847,133 B2 equivalent to patent application AR 066773 Al describes a method of preparing alkali metal alkoxides by means of a reaction step and a fractionation step in two separate columns.
  • the reaction column the top stream is split and a fraction thereof is condensed and returned as reflux to the column, while the other fraction is fed to a fractionation column using a mechanical vapor compressor .
  • compression when compared to condensation, of the alcohol vapor which leaves the reactive distillation column (to be sent to the rectification column alcohol) significantly reduces the power consumption of the process.
  • the alcohol vapor leaving the last plate of the reactive distillation column carries large amounts of alkaline mist consisting of mixtures of alcohol, water, alkali hydroxides and alkoxides. These mists, formed by droplets, carry pollutants into the rest of the plant and can compromise the performance of other equipment.
  • thermocompressor • a separation step, carried out in a fractionation column in which water is separated from the vapors containing the alkoxide and the unreacted alcohol, where said vapors obtained in the reactive distillation column are fed to the fractionation column using a thermocompressor;
  • thermocompressors instead of mechanical compressors.
  • the thermocompressors utilize the principle of drag produced by a jet of high pressure steam, which compresses the alcohol vapor stream. This process is carried out in equipment called ejectors, involving very simple construction with no moving parts. The use of these devices dramatically reduces capital costs, shutdowns and maintenance costs .
  • thermocompression reduces power consumption in a range between 30% and 60% compared to processes where the alcohol vapor is condensed before being sent by pumps to the column rectification of alcohol. This is due to a reduced consumption of steam by the reboiler of the fractionating column and the elimination of the need to use a condenser for overhead vapors from the reactive distillation column, which in turn reduces the corresponding consumption of cooling water, and the corresponding costs.
  • an alkaline mist separator located inside the reactive distillation column, between the last plate and the vapor outlet, is used.
  • the use of alkaline mist separator is aimed to retain with high efficiency droplets from the last plate of the reactive distillation column, thereby preventing them from being dragged out to other equipment within the plant.
  • Figure 1 shows a process flow diagram of the method of the present invention.
  • Figure 2 shows a process flow diagram of a method of the traditional configuration.
  • Figure 1 shows a process in which an aqueous solution of alkali metal hydroxides fed through the pipe (8) is previously heated in the equipment (9) and introduced through the pipe (10) to the top of the reactive distillation column (12), which carries an alkaline mist separator (11) near its upper end.
  • An aqueous solution of alkali metal alkoxide (14) is obtained from the bottom, and a stream (18) is obtained from the top of the reactive distillation column (12), being stream 18 a mixture of water vapor and unreacted alcohol.
  • thermocompressor (1) which operates by means of a jet of steam at high pressure.
  • This compression process allows the introduction of the vapors in the alcohol rectification column (2) through the stream (19), in order to remove process water and purify the alcohol that is recycled to the reactive distillation column (12) .
  • a water stream (3) is obtained from the bottom of the rectification column (2), which stream is separated from the unreacted alcohol.
  • Said purified alcohol is obtained from the top of the column in stream (7), which is recycled to the reactive distillation column. Part of this stream from the top, stream (6), is condensed and recycled to the tower.
  • Reactive distillation column (12) operates at a pressure lower than that of the alcohol rectification column (2) .
  • Column (2) is also equipped with a partial condenser which allows recirculation of part of the alcohol as a liquid and sends the rest in vapor form to the reactive distillation column ( 12 ) .
  • Fresh alcohol can be introduced upstream of the reboiler (16), through the stream (15a) or in the recycle stream of column 2 through the stream (15b) .
  • thermocompressor (1) a plant corresponding to the present invention in which a thermocompressor (1) is used, is shown in Figure 1, so that steam from top of column (12) is recompressed and injected in gaseous state to the dehydration column ( 2 ) .
  • thermocompressor of the plant schematized in Figure 1 consists of a steam ejector with commercial characteristics .

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)

Abstract

La présente invention concerne un procédé de préparation de solutions d'alcoxydes de métaux alcalins, au moyen d'une colonne de distillation réactive et d'une colonne de déshydratation d'alcool. Le procédé est caractérisé par l'utilisation d'un thermocompresseur, qui permet une économie considérable d'énergie et de coût de fonctionnement lors du procédé, et éventuellement d'un séparateur de brouillard alcalin situé au sommet de la colonne de distillation réactive, qui évite une contamination lors du procédé.
PCT/IB2013/053730 2012-05-10 2013-05-08 Procédé de préparation d'alcoxydes de métaux alcalins WO2013168113A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201261645480P 2012-05-10 2012-05-10
US61/645,480 2012-05-10

Publications (1)

Publication Number Publication Date
WO2013168113A1 true WO2013168113A1 (fr) 2013-11-14

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2013/053730 WO2013168113A1 (fr) 2012-05-10 2013-05-08 Procédé de préparation d'alcoxydes de métaux alcalins

Country Status (2)

Country Link
AR (1) AR093211A1 (fr)
WO (1) WO2013168113A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016083175A1 (fr) * 2014-11-24 2016-06-02 Basf Se Production d'un alcoxyde métallique par distillation réactive
CN111100008A (zh) * 2020-01-21 2020-05-05 山西中科惠安化工有限公司 一种酯交换法合成碳酸二甲酯过程中甲醇碱金属盐催化剂的再生回收装置和方法
WO2022117803A1 (fr) 2020-12-04 2022-06-09 Basf Se Procédé intégré pour la production en parallèle de méthoxydes de métaux alcalins
CN115215727A (zh) * 2021-04-16 2022-10-21 赢创功能性解决方案有限公司 碱金属醇盐的高能效制备方法
JP2022164649A (ja) * 2021-04-16 2022-10-27 エボニック ファンクショナル ソリューションズ ゲー・エム・ベー・ハー アルカリ金属アルコキシドのエネルギー効率の良い製造のための方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1910331A (en) 1931-06-24 1933-05-23 Wacker Chemie Gmbh Process of preparing alkali metal aliphatic monohydroxy alcoholates
US2877274A (en) 1958-01-21 1959-03-10 Du Pont Production of sodium methoxide
US4895989A (en) 1987-07-14 1990-01-23 Metallgesellschaft Aktiengesellschaft Process for producing alkali metal alcoholates
US6759560B2 (en) 1999-12-08 2004-07-06 Basf Aktiengesellschaft Method for producing alkali methylates
AR066773A1 (es) 2007-06-01 2009-09-09 Evonik Degussa Gmbh Proceso para preparar alcoxidos de metales alcalinos
WO2010097318A1 (fr) * 2009-02-26 2010-09-02 Basf Se Procédé de traitement par distillation d'un mélange méthanol/eau et procédé de préparation de méthylates alcalins

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1910331A (en) 1931-06-24 1933-05-23 Wacker Chemie Gmbh Process of preparing alkali metal aliphatic monohydroxy alcoholates
US2877274A (en) 1958-01-21 1959-03-10 Du Pont Production of sodium methoxide
US4895989A (en) 1987-07-14 1990-01-23 Metallgesellschaft Aktiengesellschaft Process for producing alkali metal alcoholates
US6759560B2 (en) 1999-12-08 2004-07-06 Basf Aktiengesellschaft Method for producing alkali methylates
AR066773A1 (es) 2007-06-01 2009-09-09 Evonik Degussa Gmbh Proceso para preparar alcoxidos de metales alcalinos
US7847133B2 (en) 2007-06-01 2010-12-07 Evonik Degussa Gmbh Process for preparing alkali metal alkoxides
WO2010097318A1 (fr) * 2009-02-26 2010-09-02 Basf Se Procédé de traitement par distillation d'un mélange méthanol/eau et procédé de préparation de méthylates alcalins

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
"Ludwig's applied process design for chemical and petroleum plants", 1 January 1995, ELSEVIER GULF, article LUDWIG LUDWIG: "Ludwig's applied process design for chemical and petroleum plants", pages: 343 - 398, XP055027613 *
"Managing CO2 Emissions in the Chemical Industry", 2010, WILEY -VCH VERLAG GMBH & CO. KGAA, ISBN: 978-3-527-32659-4, article ANDREAS JUPKE: "Energy Efficient Unit Operations and Processes", pages: 223 - 270, XP002699958 *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016083175A1 (fr) * 2014-11-24 2016-06-02 Basf Se Production d'un alcoxyde métallique par distillation réactive
CN111100008A (zh) * 2020-01-21 2020-05-05 山西中科惠安化工有限公司 一种酯交换法合成碳酸二甲酯过程中甲醇碱金属盐催化剂的再生回收装置和方法
WO2022117803A1 (fr) 2020-12-04 2022-06-09 Basf Se Procédé intégré pour la production en parallèle de méthoxydes de métaux alcalins
CN115215727A (zh) * 2021-04-16 2022-10-21 赢创功能性解决方案有限公司 碱金属醇盐的高能效制备方法
JP2022164648A (ja) * 2021-04-16 2022-10-27 エボニック ファンクショナル ソリューションズ ゲー・エム・ベー・ハー アルカリ金属アルコキシドのエネルギー効率の良い製造のための方法
JP2022164649A (ja) * 2021-04-16 2022-10-27 エボニック ファンクショナル ソリューションズ ゲー・エム・ベー・ハー アルカリ金属アルコキシドのエネルギー効率の良い製造のための方法
JP7411711B2 (ja) 2021-04-16 2024-01-11 エボニック オペレーションズ ゲーエムベーハー アルカリ金属アルコキシドのエネルギー効率の良い製造のための方法
JP7411710B2 (ja) 2021-04-16 2024-01-11 エボニック オペレーションズ ゲーエムベーハー アルカリ金属アルコキシドのエネルギー効率の良い製造のための方法
CN115215727B (zh) * 2021-04-16 2024-03-01 赢创运营有限公司 碱金属醇盐的高能效制备方法

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