KR930005958A - Method for producing alkyl ester having hindered hydroxyphenyl group - Google Patents

Method for producing alkyl ester having hindered hydroxyphenyl group Download PDF

Info

Publication number
KR930005958A
KR930005958A KR1019910016236A KR910016236A KR930005958A KR 930005958 A KR930005958 A KR 930005958A KR 1019910016236 A KR1019910016236 A KR 1019910016236A KR 910016236 A KR910016236 A KR 910016236A KR 930005958 A KR930005958 A KR 930005958A
Authority
KR
South Korea
Prior art keywords
alcohol
formula
butyl
water
group
Prior art date
Application number
KR1019910016236A
Other languages
Korean (ko)
Other versions
KR950005194B1 (en
Inventor
구본철
김형철
이기호
Original Assignee
김항덕
주식회사 유 공
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 김항덕, 주식회사 유 공 filed Critical 김항덕
Priority to KR1019910016236A priority Critical patent/KR950005194B1/en
Publication of KR930005958A publication Critical patent/KR930005958A/en
Application granted granted Critical
Publication of KR950005194B1 publication Critical patent/KR950005194B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/02—Preparation of carboxylic acid esters by interreacting ester groups, i.e. transesterification

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 저급 알킬 에스터 화합물을 지방족 알콜을 사용하여 알미늄 알콕사이드 촉매로 에스터 교환반응을 시킴으로써, 장애 히드록시 페닐기를 갖는 알킬에스테르를 제조하는 방법에 관한 것으로, 기존방법에는 사용되지 않았던 알루미늄 알콕사이드를 촉매로 이용하여 높은 촉매활성에 의한 전체 수율향상, 촉매 제거과정이 용이하여 별도의 촉매 축출공정이 생략, 원료비가 타촉매에 비하여 저렴한 경제적 잇점 및 인체에 무해한 저독성 효과를 얻었다. 또한, 별도의 장치없이 하나의 반응기에서 반응 및 촉매제거가 가능하게 되었고, 여과 후 곧바로 생성물을 회수할 수 있도록 제조공정을 단순화 하였으며, 저금 알킬알콜 형태의 혼합용매를 재결정 용매로 사용함으로써 부반응물의 제거를 용이하게 하고 생성물의 손실을 최소화할 수 있다.The present invention relates to a method for producing an alkyl ester having a hindered hydroxy phenyl group by transesterifying a lower alkyl ester compound with an aluminum alkoxide catalyst using an aliphatic alcohol. The overall catalyst yield is improved by high catalytic activity, and the catalyst removal process is easy, eliminating the separate catalyst extraction process, and the raw material cost is low economical advantages compared to other catalysts and harmless to human body. In addition, the reaction and catalyst removal can be performed in one reactor without a separate device, and the manufacturing process can be simplified to recover the product immediately after filtration. It is easy to remove and minimize the loss of product.

Description

장애 히드록시페닐기를 갖는 알킬에스테르의 제조방법Method for producing alkyl ester having hindered hydroxyphenyl group

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (16)

하기식(Ⅱ)의 에스터 화합물을 하기식(Ⅲ)의 지방족 알콜을 사용하여 용매없이 하기식(Ⅳ)의 알미늄 알콕사이드 촉매로 에스터 교환반응을 시키며, 저급 알킬 카르복실산으로 잔존하는 촉매를 제거해 주고, 물과 저급지방족 알콜의 혼합체로 구성되어지는 용재로 반응 생성물을 회수하는 것을 특징으로 하는 하기식(Ⅰ)의 장애 히드록시 페닐기를 가진 알킬 에스테르를 제조하는 방법에 관한 것이다.The ester compound of formula (II) is transesterified with an aluminum alkoxide catalyst of formula (IV) without solvent using an aliphatic alcohol of formula (III) to remove the remaining catalyst with lower alkyl carboxylic acid. The present invention relates to a method for producing an alkyl ester having a hindered hydroxy phenyl group of formula (I), wherein the reaction product is recovered by a solvent composed of a mixture of water and a lower aliphatic alcohol. (Ⅲ)Ra-OH(Ⅳ)Al(OT)3상기식에서 R1및 R2는 서로 독립해서 1내지 6의 탄소 원자를 갖는 알킬기이고, R3은 6내지 30의 탄소 원자를 갖는 알킬기이고, X는 0내지 6의 정수이며, 또한 R은 탄소수 1내지 6의 저급 알킬이다.(III) R a -OH (IV) Al (OT) 3 wherein R 1 and R 2 are each independently an alkyl group having 1 to 6 carbon atoms, and R 3 is an alkyl group having 6 to 30 carbon atoms , X is an integer of 0 to 6, and R is lower alkyl having 1 to 6 carbon atoms. 제1항에 있어서, R1및 R2가 서로 독립적으로 메틸, 에틸, n-프로필, 이소프로필, n-부틸, 3차 부틸 또는 3차 펜틸기인 것을 특징으로 하는 방법.A process according to claim 1, wherein R 1 and R 2 are independently of each other a methyl, ethyl, n-propyl, isopropyl, n-butyl, tertiary butyl or tertiary pentyl group. 제1항에 있어서, 상기 R2치환체는 히드록시기에 대하여 오르소 또는 메타 위치로 페닐기에 존재하는 것을 특징으로 하는 방법.The method of claim 1 wherein the R 2 substituent is present in the phenyl group in ortho or meta position relative to the hydroxy group. 제1항에 있어서, 상기 R2가 n-헥실, n-옥틸, n-데실, n-도데실, n-헥사데실 또는 n-옥타데실기인 것을 특징으로 하는 방법.The method of claim 1, wherein R 2 is n-hexyl, n-octyl, n-decyl, n-dodecyl, n-hexadecyl or n-octadecyl group. 제1항에 있어서, 상기 R이 에틸, n-프로필, n-부틸 또는 sec-부틸, 이소프로필기인 것을 특징으로 하는 방법.The method of claim 1 wherein R is an ethyl, n-propyl, n-butyl or sec-butyl, isopropyl group. 제1항에 있어서, 상기 저급 알킬 카르복실산이 아세트산인 것을 특징으로 하는 방법.The method of claim 1 wherein the lower alkyl carboxylic acid is acetic acid. 제1항에 있어서, 상기 지방족 알콜이 메틸알콜 에틸알콜, 프로필알콜, 이소프로필알콜, 부틸알콜, sec-부틸알콜, t-부틸알콜 또는 이들의 혼합물인 것을 특징으로 하는 방법.The method of claim 1, wherein the aliphatic alcohol is methyl alcohol ethyl alcohol, propyl alcohol, isopropyl alcohol, butyl alcohol, sec-butyl alcohol, t-butyl alcohol or a mixture thereof. 제1항 또는 제7항에 있어서, 상기 물과 저급지방족 알콜의 혼합체가 10~20wt%의 물을 함유하는 것을 특징으로 하는 방법.8. A method according to claim 1 or 7, wherein the mixture of water and lower aliphatic alcohols contains 10-20 wt% water. 제8항에 있어서, 상기 몰과 저급지방족 알콜의 혼합체가 메틸알콜, 이소프로필알콜 및 물로 구성된 혼합 알콜인 것을 특징으로 하는 방법.The method according to claim 8, wherein the mixture of moles and lower aliphatic alcohols is a mixed alcohol consisting of methyl alcohol, isopropyl alcohol and water. 제9항에 있어서, 상기 물과 저급지방족 알콜의 혼합체가 10~20wt%의 물, 5~15wt%의 메틸알콜 및 70~85wt%의 이소프로필 알콜로 구성된 것을 특징으로 하는 방법.10. The method of claim 9, wherein the mixture of water and lower aliphatic alcohol is comprised of 10-20 wt% water, 5-15 wt% methyl alcohol, and 70-85 wt% isopropyl alcohol. 제1항에 있어서, 상기 식(Ⅱ)의 에스터 화합물에 대해 상기식(Ⅲ)의 지방족 알콜이 1.0~1.5당량으로 사용되는 것을 특징으로 하는 방법.The method according to claim 1, wherein the aliphatic alcohol of formula (III) is used in an amount of 1.0 to 1.5 equivalents based on the ester compound of formula (II). 제1항에 있어서, 알루미늄 알콕사이드의 총량은 상기 식(Ⅰ)의 에스터 화합물에 대해 0.1~10.0몰%인 것을 특징으로 하는 방법.The method according to claim 1, wherein the total amount of aluminum alkoxide is 0.1 to 10.0 mol% based on the ester compound of formula (I). 제1항에 있어서, 반응온도는 70℃~150℃범위내로 유지됨을 특징으로 하는 방법.The method of claim 1, wherein the reaction temperature is maintained in the range of 70 ℃ ~ 150 ℃. 제1항에 있어서, 반응압력은 20~30mmHg범위내로 유지됨을 특징으로 하는 방법.The method of claim 1, wherein the reaction pressure is maintained in the range of 20 to 30mmHg. 제1항 또는 제6항에 있어서, 상기 저급 알킬 카르복실산이 첨가된 촉매에 대하여 2.5~6당량 만큼 첨가되는 것을 특징으로 하는 방법.7. Process according to claim 1 or 6, wherein the lower alkyl carboxylic acid is added in an amount of 2.5 to 6 equivalents relative to the added catalyst. 제1항에 있어서, 아세트산 첨가후 유지되는 온도가 60~100℃인 것을 특징으로 하는 방법.The method according to claim 1, wherein the temperature maintained after acetic acid is 60 to 100 ° C. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019910016236A 1991-09-17 1991-09-17 Preparation of alkylesters with sterically hindered hydroxyphenol KR950005194B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1019910016236A KR950005194B1 (en) 1991-09-17 1991-09-17 Preparation of alkylesters with sterically hindered hydroxyphenol

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1019910016236A KR950005194B1 (en) 1991-09-17 1991-09-17 Preparation of alkylesters with sterically hindered hydroxyphenol

Publications (2)

Publication Number Publication Date
KR930005958A true KR930005958A (en) 1993-04-20
KR950005194B1 KR950005194B1 (en) 1995-05-19

Family

ID=19320060

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019910016236A KR950005194B1 (en) 1991-09-17 1991-09-17 Preparation of alkylesters with sterically hindered hydroxyphenol

Country Status (1)

Country Link
KR (1) KR950005194B1 (en)

Also Published As

Publication number Publication date
KR950005194B1 (en) 1995-05-19

Similar Documents

Publication Publication Date Title
CA2431365A1 (en) Process for the simultaneous coproduction and purification of ethyl acetate and isopropyl acetate
US4526725A (en) Catalyst composition and method for the manufacture of esters
US20030166962A1 (en) Method for preparing hydroxyphenyl carboxylic acid esters
KR930005958A (en) Method for producing alkyl ester having hindered hydroxyphenyl group
GB2194944A (en) Preparation of unsaturated carboxylic acid esters
EP0044510B1 (en) Process for the preparation of diaryl esters
JP2904543B2 (en) Method for producing ester
Haslam et al. 1019. Synthesis of 3-O-p-coumaroylquinic acid
US4663477A (en) Process for the hydrolysis of dialkyl carbonates
DE3901095A1 (en) METHOD FOR PRODUCING GUERBET ALCOHOLS
CA1333615C (en) Transesterification of alkoxyesters
US3941811A (en) Oxidation process
US2164154A (en) Hydrogenation of mono nitrated alkoxy benzenes
US4111993A (en) Process for racemization of allethrolone
US2476053A (en) Process for producing esters
US2935525A (en) Esterification of organic acids
US3920746A (en) Preparation of tertiary-butyl aryl ethers
SU621313A3 (en) Method of extracting propylene glycol dicarboxylate
US5011977A (en) Transesterification of alkoxyesters
US3448146A (en) Process for purifying terephthalic acid
JP3489594B2 (en) Method for producing hydroxypivalic acid ester
US3026349A (en) Production of trans-beta-styrylthioglycolic acid
US2801262A (en) Production of phenols and alkanoates thereof
Matsumoto et al. Abnormal Reduction of 2-Methoxy-5-hydroxy-1-naphthylacetic Acid
JPH0678262B2 (en) Process for producing α-hydroxyketones

Legal Events

Date Code Title Description
A201 Request for examination
G160 Decision to publish patent application
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20080519

Year of fee payment: 14

LAPS Lapse due to unpaid annual fee