KR950017904A - 수율이 높은 메타크릴산 에스테르 제조방법 - Google Patents

수율이 높은 메타크릴산 에스테르 제조방법 Download PDF

Info

Publication number
KR950017904A
KR950017904A KR1019940032179A KR19940032179A KR950017904A KR 950017904 A KR950017904 A KR 950017904A KR 1019940032179 A KR1019940032179 A KR 1019940032179A KR 19940032179 A KR19940032179 A KR 19940032179A KR 950017904 A KR950017904 A KR 950017904A
Authority
KR
South Korea
Prior art keywords
alkyl
mixture
esterification
methacrylic acid
isobutyrate
Prior art date
Application number
KR1019940032179A
Other languages
English (en)
Other versions
KR100411499B1 (ko
Inventor
캐롤 돕슨 존
Original Assignee
윌리엄 이. 램버트 3세
롬 앤드 하스 캄파니
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 윌리엄 이. 램버트 3세, 롬 앤드 하스 캄파니 filed Critical 윌리엄 이. 램버트 3세
Publication of KR950017904A publication Critical patent/KR950017904A/ko
Application granted granted Critical
Publication of KR100411499B1 publication Critical patent/KR100411499B1/ko

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/18—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group
    • C07C67/20—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group from amides or lactams
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C67/327—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by elimination of functional groups containing oxygen only in singly bound form

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

본 발명은 반응부산물을 감소시키고 중간물질을 공정에 재순환시킴으로써, 아세톤시안히드린과 황산으로 부터 높은 수율로 α, β-불포화 카르복시산에스테르를 제조하는 방법을 제공한다.

Description

수율이 높은 메타크릴산 에스테르 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (9)

  1. a. ACH로 부터 유도된 2-메타크릴아미드(MAM), α-술페이토이소부티르아미드(SIBAM), α-히드록시이소브티르아미드(HIBAM) 및 메타크릴산(MAA)의 전체 몰수의 합이 최대가 되도록 아세톤 시안히드린을 가수분해하여 2-메타크릴아미드, α-술페이토이소부티르아미드, α-히도록시이소부티르아미드 및 메타크릴산을 포함하는 가수분해 혼합물을 제조하는 단계. b. 상기 가수분해 흔합물을 C1-C12 알킬알코올로 에스테르화하여 C1-Cl2알킬 메타 크릴레이트, C1-C2 알킬 α-히드록시이소부티르레이트, C1-Cl2 알킬-C1-Cl2알콕시 이소부티르레이트 및 C1-Cl2알킬 α-C1-Cl2알콕시이소부티르레이트를 포함하는 에스테르화 혼합물을 제조하는 단계:c. 상기 에스테르화 혼합물을 수성 부분,C1-Cl2 메타크릴레이트를 포함하는 제1유기부분 C1-Cl2알킬 α-히드록시이소부티르레이트, C1-C12 알킬-C1-Cl2 알록시 이소부티르레이트 및 C1-Cl2알킬 β-C1-Cl2알콕시 이소부티르레이트를 포함하는 제2유기부분으로 분리하는 단계:d. 상기 제2유기 부분의 이소부티르레이트-함유 성분을 탈수하여 C1-Cl2알킬 메타 크릴레이트, 메타크릴산, C1-Cl2 알킬 알코올 및 물을 포함하는 재순환 혼합물을 제조하는 단계;e. 상기 재순환 혼합물을 상기 가수분해 흔합물 또는 상기 에스테르화 혼합물과 결합하는 단계;를 포함하는 메닥크릴산 에스테르 제조방법.
  2. 1항에 있어서, 에스테르화 단계 직전의 공전 스트림내의 α-히드록시이소부티르아미드의 농도는 상기 아세톤 시안히드린 출발물질을 기준으로 약 2-20몰%임을 특징으로 하는 방법.
  3. 1항에 있어서, 에스테르화 단계 직전의 공정 스트림내의 α-히드록시이소부티르아미드의 농도는 상기 아세톤 시안히드린 출발물질을 기준으로 약 5-15몰%임을 특징으로 하는 방법.
  4. 1항에 있어서, 에스테르화 단계 직전의 공정 스트림내의 α-술페이토이소부티르아미드의 농도는 상기 아세톤 시안히드린 출발물질을 기준으로 약 1-20몰%임을 특징으로 하는 방법.
  5. 1항에 있어서, 상기 C1-Cl2알킬알코올은 메탄올, 에탄올, n-프로판올, 이소프로판올, n-부탄올 및 이소프로판올로 구성되는 그룹으로 부터 선택됨을 특징으로 하는 방법.
  6. 1항에 있어서, 상기 C1-Cl2알킬 알코올은 메탄올임을 특징으로 하는 방법,
  7. 1항에 있어서, 상기 분리단계는 에스테르화 혼할물의 분별증류를 포함함을 특징으로 하는 방법.
  8. 1항에 있어서, 상기 탈수단계는 결정성 알루미노 실리케이트의 존재하에서 기상(vapor phase)에서 행하여짐을 특징으로 하는 방법.
  9. 8항에 있어서, 상기 결정성 알루미노실리케이트는 알칼리 금속 및 배금족 원소로 변형됨을 특징으로 하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019940032179A 1993-12-02 1994-11-30 수율이높은메타크릴산에스테르제조방법 KR100411499B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/160697 1993-12-02
US08/160,697 US5393918A (en) 1993-12-02 1993-12-02 High yield process for the production of methacrylic acid esters

Publications (2)

Publication Number Publication Date
KR950017904A true KR950017904A (ko) 1995-07-20
KR100411499B1 KR100411499B1 (ko) 2004-03-20

Family

ID=22578043

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019940032179A KR100411499B1 (ko) 1993-12-02 1994-11-30 수율이높은메타크릴산에스테르제조방법

Country Status (13)

Country Link
US (1) US5393918A (ko)
EP (1) EP0656343B1 (ko)
JP (1) JP3860234B2 (ko)
KR (1) KR100411499B1 (ko)
CN (1) CN1041410C (ko)
BR (1) BR9404473A (ko)
CA (1) CA2135438A1 (ko)
CZ (1) CZ303494A3 (ko)
DE (1) DE69403883T2 (ko)
ES (1) ES2104288T3 (ko)
RU (1) RU2131867C1 (ko)
SG (1) SG81884A1 (ko)
TW (1) TW319774B (ko)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9802662D0 (en) * 1998-02-10 1998-04-01 Ici Plc Unsaturated compounds
EP0999200B1 (en) 1998-11-04 2002-07-17 Rohm And Haas Company Process for the high yield production of methyl methacrylate or methacrylic acid
EP1186592A1 (en) * 2000-09-11 2002-03-13 Mitsubishi Gas Chemical Company, Ltd. Production of methacrylates
TWI254648B (en) * 2002-05-01 2006-05-11 Rohm & Haas Process for manufacturing high purity methacrylic acid
ZA200303241B (en) * 2002-05-01 2003-11-04 Rohm & Haas Improved process for methacrylic acid and methcrylic acid ester production.
CN100584822C (zh) * 2004-04-02 2010-01-27 西巴特殊化学水处理有限公司 由α或β-羟基羧酸制备丙烯酸衍生物
DE102006058251A1 (de) * 2006-12-08 2008-06-12 Evonik Röhm Gmbh Verfahren und Vorrichtung zur Herstellung von Methacrylsäurealkylestern
DE102006060161A1 (de) * 2006-12-18 2008-06-26 Evonik Röhm Gmbh Verfahren zur adsorptiven Aufreinigung von Methacrylsäurealkylestern
JP5432852B2 (ja) 2009-09-30 2014-03-05 ローム アンド ハース カンパニー メタクリル酸メチルの精製によって生じる流れから価値のある化合物を回収する方法
WO2012047883A1 (en) 2010-10-07 2012-04-12 Rohm And Haas Company Process for production of methacrylic acid ester
DE102011076642A1 (de) * 2011-05-27 2012-11-29 Evonik Röhm Gmbh Verfahren zur Herstellung von Methacrylsäure
US9815097B2 (en) 2011-09-27 2017-11-14 Rohm And Haas Company Method for cleaning a (meth)acrylate ester process tank
US9199910B2 (en) 2012-06-04 2015-12-01 Rohm And Haas Company Process for production of methacrylic acid esters
US9260368B2 (en) * 2012-09-28 2016-02-16 Rohm And Haas Company Process for producing MMA and/or MAA from acetone cyanohydrin and sulfuric acid
CN103130671B (zh) * 2013-03-28 2015-06-17 重庆紫光化工股份有限公司 一种清洁的甲基丙烯酰胺的制备和提纯方法
US20160102043A1 (en) * 2013-06-26 2016-04-14 Rohm And Haas Company Process for production of methacrylic acid esters
AU2015332509B2 (en) 2014-10-14 2020-05-21 Gevo, Inc. Methods for conversion of ethanol to functionalized lower hydrocarbons and downstream hydrocarbons
EP3735401B1 (en) 2018-01-04 2023-04-26 GEVO, Inc. Upgrading fusel oil mixtures over heterogeneous catalysts to higher value renewable chemicals
JP2023547392A (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メタクリル酸（ｍａｓ）および／またはアルキルメタクリレートの最適化された製造方法
US20230399286A1 (en) 2020-10-23 2023-12-14 Röhm Gmbh Improved process for preparing methyl methacrylate and/or methacrylic acid by reduced back mixing during conversion
EP4045479B1 (de) 2020-10-23 2022-10-26 Röhm GmbH Optimiertes verfahren zur herstellung von alkylmethacrylat durch reduzierung störender nebenprodukte
WO2023117754A1 (de) 2021-12-23 2023-06-29 Röhm Gmbh Verfahren zur herstellung von alkylmethacrylaten mit verbesserter ausbeute und verminderten emissionen flüchtiger organischer verbindungen
WO2023169810A1 (de) 2022-03-11 2023-09-14 Röhm Gmbh Verfahren zur herstellung von alpha-hydroxyisobuttersäuremethylester und dessen anwendung in der elektronik-industrie

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2416756A (en) * 1941-10-23 1947-03-04 Du Pont Continuous production of esters of methacrylic acid
US2786739A (en) * 1954-05-10 1957-03-26 Allied Chem & Dye Corp Continuous process for the production of methacrylic acid esters and ammonium sulphate
US3027328A (en) * 1958-12-09 1962-03-27 Degussa Process for the preparation of acetonecyanohydrin/sulfuric acid mixtures
JPS5767534A (en) * 1980-10-16 1982-04-24 Mitsui Toatsu Chem Inc Preparation of alpha,beta-unsaturated carboxylic ester and alpha,beta-unsaturated carboxylic acid
US4529816A (en) * 1984-02-13 1985-07-16 E. I. Du Pont De Nemours And Company Process for producing alkyl methacrylates
ES2012539A6 (es) * 1987-08-20 1990-04-01 Du Pont Procedimiento para la produccion de acido metacrilico y sus esteres dealquilo.
JP2727618B2 (ja) * 1989-01-26 1998-03-11 三菱瓦斯化学株式会社 不飽和カルボン酸エステルの製造方法
JP2778131B2 (ja) * 1989-07-14 1998-07-23 三菱瓦斯化学株式会社 メタクリル酸メチルの製造方法
JP2884638B2 (ja) * 1989-11-28 1999-04-19 三菱瓦斯化学株式会社 不飽和カルボン酸エステルの製造法
JP2884639B2 (ja) * 1989-11-28 1999-04-19 三菱瓦斯化学株式会社 不飽和カルボン酸エステルの製造法
JPH03264551A (ja) * 1990-03-15 1991-11-25 Kuraray Co Ltd メタクリル酸メチルの回収方法

Also Published As

Publication number Publication date
CN1109865A (zh) 1995-10-11
RU94042228A (ru) 1996-10-10
EP0656343B1 (en) 1997-06-18
SG81884A1 (en) 2001-07-24
TW319774B (ko) 1997-11-11
CN1041410C (zh) 1998-12-30
KR100411499B1 (ko) 2004-03-20
BR9404473A (pt) 1995-07-25
EP0656343A1 (en) 1995-06-07
JPH07196576A (ja) 1995-08-01
RU2131867C1 (ru) 1999-06-20
DE69403883T2 (de) 1998-02-12
ES2104288T3 (es) 1997-10-01
CA2135438A1 (en) 1995-06-03
JP3860234B2 (ja) 2006-12-20
CZ303494A3 (en) 1995-11-15
US5393918A (en) 1995-02-28
DE69403883D1 (de) 1997-07-24

Similar Documents

Publication Publication Date Title
KR950017904A (ko) 수율이 높은 메타크릴산 에스테르 제조방법
MX9700896A (es) Preparacion continua de esteres de alquil del acido (met)acrilico.
AU2002218298A1 (en) Method for producing esters of multibasic acids
NZ539737A (en) Methods for producing fatty acid alkyl esters
MX9700899A (es) Preparacion continua de esteres de alquilo del acido (met) acrilico.
KR900014294A (ko) 메틸메타크릴레이트의 정재 및 제조방법
DK0609127T3 (da) Forbedret fremgangsmåde til fremstilling af alkyl(meth)acrylater ved direkte esterificering
TW472039B (en) Process for esterifying (meth)acrylic acid with alkanol
ATE322499T1 (de) Verfahren zur herstellung von 2-keto-l-gulonsäure-c-4 c-10 /sb -alkylestern
AU689356B2 (en) Process for preparation of cinnamate sunscreen agents
MY123466A (en) Method for esterifying (meth) acrylic acid with an alkanol.
KR970015557A (ko) 알칸올을 사용한 (메트) 아크릴산의 에스테르화 방법
US2816921A (en) Production of alpha-alkoxy alkanoic acids
GB953775A (en) Processes for the preparation of sorbic acid and alkyl esters of sorbic acid
ES8707174A1 (es) Un procedimiento para preparar esteres de acido trans-beta-benzoilacrilico
SK59893A3 (en) Method of production of tetronic acid alkylester
US6545175B1 (en) Ester compounds and their use in forming acrylates
KR880009898A (ko) (r)-2-하이드록시-4-페닐부티르산 및 에스테르의 제조 및 분리방법
GB668285A (en) Improvements in or relating to method of producing alkyl esters of alpha-beta unsaturated monocarboxylic acids
US6175024B1 (en) Synthesis of functionalized esters
US3170939A (en) Carboxylated derivatives of oleyl alcohol and method for their production
US4433163A (en) Process for the production of 3,3-dimethylglutaric acid or its esters
US3169140A (en) Carboxylated derivatives of oleyl alcohol and method of preparation
RU94036281A (ru) Способ получения 2-метил-2-этил-1,3-диоксолан-4-ил-метилметакрилата /изобутилиденглицерилметакрилата/
GB760078A (en) Production of derivatives of cyclo-octane having strong cholagogic activity

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20061128

Year of fee payment: 4

LAPS Lapse due to unpaid annual fee