RU2722364C2 - Синтез метакриловой кислоты из алкилметакрилата на основе метакролеина - Google Patents

Синтез метакриловой кислоты из алкилметакрилата на основе метакролеина Download PDF

Info

Publication number
RU2722364C2
RU2722364C2 RU2018113528A RU2018113528A RU2722364C2 RU 2722364 C2 RU2722364 C2 RU 2722364C2 RU 2018113528 A RU2018113528 A RU 2018113528A RU 2018113528 A RU2018113528 A RU 2018113528A RU 2722364 C2 RU2722364 C2 RU 2722364C2
Authority
RU
Russia
Prior art keywords
methacrylic acid
process step
alkyl methacrylate
reactor
methacrolein
Prior art date
Application number
RU2018113528A
Other languages
English (en)
Russian (ru)
Other versions
RU2018113528A (ru
RU2018113528A3 (enExample
Inventor
Штеффен КРИЛЛЬ
Маттиас ГРЁМПИНГ
Александер ЛИГИН
Original Assignee
Рём ГмбХ
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 Рём ГмбХ filed Critical Рём ГмбХ
Publication of RU2018113528A publication Critical patent/RU2018113528A/ru
Publication of RU2018113528A3 publication Critical patent/RU2018113528A3/ru
Application granted granted Critical
Publication of RU2722364C2 publication Critical patent/RU2722364C2/ru

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/75—Reactions with formaldehyde
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C47/22—Acryaldehyde; Methacryaldehyde
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
    • C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03—Monocarboxylic acids
    • C07C57/04—Acrylic acid; Methacrylic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/39—Preparation of carboxylic acid esters by oxidation of groups which are precursors for the acid moiety of the ester
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/44—Preparation of carboxylic acid esters by oxidation-reduction of aldehydes, e.g. Tishchenko reaction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/54—Acrylic acid esters; Methacrylic acid esters
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00583—Features relative to the processes being carried out
    • B01J2219/0059—Sequential processes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
    • C07C2527/03—Acids of sulfur other than sulfhydric acid or sulfuric acid, e.g. halosulfonic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
    • C07C2527/053—Sulfates or other compounds comprising the anion (SnO3n+1)2-
    • C07C2527/054—Sulfuric acid or other acids with the formula H2Sn03n+1
    • 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
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
RU2018113528A 2015-09-16 2016-09-09 Синтез метакриловой кислоты из алкилметакрилата на основе метакролеина RU2722364C2 (ru)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP15185441.1A EP3144291A1 (de) 2015-09-16 2015-09-16 Synthese von methacrylsäure aus auf methacrolein basierenden alkylmethacrylat
EP15185441.1 2015-09-16
PCT/EP2016/071241 WO2017046001A1 (de) 2015-09-16 2016-09-09 Synthese von methacrylsäure aus auf methacrolein basierenden alkylmethacrylat

Publications (3)

Publication Number Publication Date
RU2018113528A RU2018113528A (ru) 2019-10-16
RU2018113528A3 RU2018113528A3 (enExample) 2019-12-02
RU2722364C2 true RU2722364C2 (ru) 2020-05-29

Family

ID=54147092

Family Applications (1)

Application Number Title Priority Date Filing Date
RU2018113528A RU2722364C2 (ru) 2015-09-16 2016-09-09 Синтез метакриловой кислоты из алкилметакрилата на основе метакролеина

Country Status (12)

Country Link
US (1) US10479754B2 (enExample)
EP (2) EP3144291A1 (enExample)
JP (1) JP6824253B2 (enExample)
KR (1) KR102638806B1 (enExample)
CN (1) CN108137474B (enExample)
BR (1) BR112018005075B8 (enExample)
ES (1) ES2738990T3 (enExample)
RU (1) RU2722364C2 (enExample)
SA (1) SA518391122B1 (enExample)
SG (1) SG11201802077QA (enExample)
TW (1) TWI707842B (enExample)
WO (1) WO2017046001A1 (enExample)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX2019013522A (es) * 2017-05-25 2020-02-13 Rohm & Haas Proceso para preparar metacroleina.
CN108440281B (zh) * 2018-03-16 2021-03-02 上海载正化工科技发展有限公司 化学反应装置及其应用
FR3080623B1 (fr) * 2018-04-27 2021-01-08 Arkema France Valorisation de resine (meth)acrylique par depolymerisation et hydrolyse
EP3587390A1 (de) * 2018-06-26 2020-01-01 Röhm GmbH Verfahren zur herstellung von mma in hohen ausbeuten
EP3608305A1 (en) * 2018-08-10 2020-02-12 Röhm GmbH Process for producing methacrylic acid or methacrylic acid esters
EP3760608A1 (de) * 2019-07-05 2021-01-06 Röhm GmbH Verfahren zur herstellung von alkylmethacrylaten und optional methacrylsäure
EP3786148A1 (de) 2019-08-28 2021-03-03 Röhm GmbH Vereinfachte aufarbeitung des reaktoraustrags einer oxidativen veresterung
EP3798202A1 (de) * 2019-09-25 2021-03-31 Röhm GmbH Verfahren zur aufreinigung von methylmethacrylat von leichtsiedenden komponenten
EP3798206A1 (de) 2019-09-25 2021-03-31 Röhm GmbH Verfahren zur herstellung von alkylmethacrylaten mit verbesserter wasser- und säureführung
KR102735575B1 (ko) * 2019-10-01 2024-11-27 주식회사 엘지화학 (메트)아크릴산 및 메틸메타크릴레이트의 제조 방법
JP2023547391A (ja) * 2020-10-23 2023-11-10 レーム・ゲーエムベーハー 不要な副産物の低減によるアルキルメタクリレートの最適化された製造方法
WO2023059681A1 (en) 2021-10-08 2023-04-13 Dow Global Technologies Llc Process for methacrylic acid production
EP4605365A1 (en) 2022-12-08 2025-08-27 Rohm and Haas Company Process for concurrent methyl methacrylate and methacrylic acid production

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU668592A3 (ru) * 1971-12-06 1979-06-15 Дзе Стандарт Ойл Компани (Фирма) Способ совместного получени акриловой или метакриловой кислот и их с -с -алкиловых эфиров
DE102011076642A1 (de) * 2011-05-27 2012-11-29 Evonik Röhm Gmbh Verfahren zur Herstellung von Methacrylsäure
WO2014170223A1 (de) * 2013-04-19 2014-10-23 Evonik Industries Ag Verfahren zur herstellung von methylmethacrylat

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH430691A (de) 1963-09-17 1967-02-28 Lonza Ag Verfahren zur Herstellung von Methacrylverbindungen
DE3106557A1 (de) 1981-02-21 1982-09-16 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von (alpha)-alkylacroleinen
DE3213681A1 (de) 1982-04-14 1983-10-27 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von (alpha)-alkylacroleinen
JP2959121B2 (ja) 1990-11-28 1999-10-06 三菱瓦斯化学株式会社 メタクリル酸の製造法
JP3681285B2 (ja) * 1997-07-08 2005-08-10 旭化成ケミカルズ株式会社 メタクリル酸メチルの製造方法
JPH11246453A (ja) * 1998-03-04 1999-09-14 Asahi Chem Ind Co Ltd メタクロレイン及びメタノールの回収方法
JP2003113132A (ja) * 2001-10-05 2003-04-18 Asahi Kasei Corp メタクロレインの製造方法
ZA200303241B (en) 2002-05-01 2003-11-04 Rohm & Haas Improved process for methacrylic acid and methcrylic acid ester production.
CN1214865C (zh) * 2003-01-22 2005-08-17 中国科学院过程工程研究所 一种用于甲基丙烯醛一步氧化酯化生产甲基丙烯酸甲酯的新型催化剂
MY139387A (en) * 2004-11-17 2009-09-30 Asahi Kasei Chemicals Corp Oxidation catalyst and oxidation method
EP1995231B1 (en) * 2007-05-25 2013-11-20 Evonik Röhm GmbH Process for preparation of methyl methacrylate using recycled methanol
CN101074192A (zh) * 2007-06-20 2007-11-21 天津大学 以甲醛为原料制备甲基丙烯酸甲酯的方法
RU89631U1 (ru) 2009-08-12 2009-12-10 Открытое акционерное общество Конструкторско-производственное предприятие "Авиамотор" Устройство для привода исполнительного механизма
US20140206897A1 (en) * 2013-01-22 2014-07-24 Saudi Basic Industries Corporation Method for making methyl methacrylate from propionaldehyde and formaldehyde via oxidative esterification
CN103254091B (zh) * 2013-05-21 2015-04-08 重庆紫光化工股份有限公司 一种甲基丙烯酰胺、甲基丙烯酸甲酯和甲基丙烯酸的联合生产方法
WO2015043861A1 (de) * 2013-09-26 2015-04-02 Evonik Industries Ag Verfahren zur herstellung von methacrolein und dessen konditionierung/entwässerung für die direkte oxidative veresterung
CN103846104A (zh) 2014-02-17 2014-06-11 河南颖泰农化股份有限公司 以丙醛、甲醛为原料合成异丁烯醛用催化剂及其应用

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU668592A3 (ru) * 1971-12-06 1979-06-15 Дзе Стандарт Ойл Компани (Фирма) Способ совместного получени акриловой или метакриловой кислот и их с -с -алкиловых эфиров
DE102011076642A1 (de) * 2011-05-27 2012-11-29 Evonik Röhm Gmbh Verfahren zur Herstellung von Methacrylsäure
WO2014170223A1 (de) * 2013-04-19 2014-10-23 Evonik Industries Ag Verfahren zur herstellung von methylmethacrylat

Also Published As

Publication number Publication date
KR20180052741A (ko) 2018-05-18
WO2017046001A1 (de) 2017-03-23
JP2018527376A (ja) 2018-09-20
BR112018005075B1 (pt) 2021-06-29
EP3350152A1 (de) 2018-07-25
ES2738990T3 (es) 2020-01-28
JP6824253B2 (ja) 2021-02-03
TWI707842B (zh) 2020-10-21
TW201722901A (zh) 2017-07-01
CN108137474A (zh) 2018-06-08
EP3350152B1 (de) 2019-06-12
RU2018113528A (ru) 2019-10-16
US10479754B2 (en) 2019-11-19
KR102638806B1 (ko) 2024-02-20
BR112018005075A8 (pt) 2018-10-02
BR112018005075A2 (pt) 2018-10-02
BR112018005075B8 (pt) 2021-10-05
US20180251418A1 (en) 2018-09-06
SG11201802077QA (en) 2018-04-27
SA518391122B1 (ar) 2022-05-08
CN108137474B (zh) 2021-09-17
EP3144291A1 (de) 2017-03-22
RU2018113528A3 (enExample) 2019-12-02

Similar Documents

Publication Publication Date Title
CN108137474B (zh) 从基于甲基丙烯醛的甲基丙烯酸烷基酯合成甲基丙烯酸
RU2645214C2 (ru) Способ получения метакролеина и его кондиционирование/обезвоживание для прямой окислительной этерификации
CN112521283B (zh) 含钠盐的mma-甲醇混合物的提取处理
US5187309A (en) Process for the continuous preparation of lower acrylates
JP7502422B2 (ja) 低沸点成分からメチルメタクリレートを精製する方法
KR102331106B1 (ko) 개선된 알킬 (메트)아크릴레이트의 제조 방법
JP2021529192A (ja) 軽質アクリレートを精製するための方法
TW202302513A (zh) 藉由甲基丙烯酸甲酯之催化水解而連續製備甲基丙烯酸之新穎方法
TW202528284A (zh) 利用甲基丙烯酸烷酯的水解以連續製備甲基丙烯酸之方法
JP2024506199A (ja) 高純度アルキルアクリレートを製造するための改善された方法
KR101392435B1 (ko) 알킬(메트)아크릴레이트의 제조 방법
JP2026511119A (ja) 軽質アルキルアクリレートを精製するための方法
KR20240050334A (ko) 고순도 부틸 아크릴레이트의 개선된 제조 방법
JP2024543443A (ja) メタクロレインの直接酸化的エステル化における煩雑な二次生成物を除去する方法
JP2000290217A (ja) アセトンの精製方法
JP2022549484A (ja) 水および酸の制御が改善されたアルキルメタクリレートの製造方法
JP2003252832A (ja) (メタ)アクリル酸エステル製造時の副生物の分解方法

Legal Events

Date Code Title Description
HZ9A Changing address for correspondence with an applicant
PD4A Correction of name of patent owner