KR840000469A - A process for producing carboxylic acid esters from an acylium anion produced by carbonylation reaction. - Google Patents

A process for producing carboxylic acid esters from an acylium anion produced by carbonylation reaction. Download PDF

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KR840000469A
KR840000469A KR1019820002510A KR820002510A KR840000469A KR 840000469 A KR840000469 A KR 840000469A KR 1019820002510 A KR1019820002510 A KR 1019820002510A KR 820002510 A KR820002510 A KR 820002510A KR 840000469 A KR840000469 A KR 840000469A
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에프. 파스코 랄프 (외 1)
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티. 진 딜라헌티
애슈랜드 오일 인코포레이팃드
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Abstract

내용 없음No content

Description

카르보닐화반응에 의해 생성된 아실리움 음이온으로부터 카르복실산에스테르류의 제조방법Method for producing carboxylic acid esters from acylium anion produced by carbonylation reaction

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

첨부된 도면은 본 발명의 에스테르화공정 및 분리공정을 나타낸 공정도임.The accompanying drawings are process diagrams illustrating an esterification process and a separation process of the present invention.

Claims (24)

일산화탄소, 불소산(HF)와 염산(HCl)중에서 선택된 무수산 및 일반식(여기서, R는 탄소원자수가 최대 20개인 알킬기이고, R'는 탄소원자수가 2내지 20개인 알킬이다)로 나타내는 에스테르 및 이 에스테르와 아실리움 음이온을 형성할 수 있는 1개 이상의 이중결합을 갖는 탄소원자수가 20개인 올레핀중에서 선택된 일산화탄소와의 반응성이 있는 유기화합물의 반응생성물인 아실리움 음이온 생성물로 이루어진 혼합물을 이 혼합물중의 아실리움 음이온전량을 에스테르화시켜 카르복실산 에스테르로 변환시키는 데 요하는 양이하의 알코올로 20°내지 150℃의 온도 및 1바아(14.7psia)내지 340바아 (5000psia)의 압력하에 아실리움 음이온생성물에 대한 무수산의 초기비율을 아실리움 음이온생성물 99.09내지 4.5중량부에 대하여 0.01내지 95.5중량부의 범위로 하여 에스테르화시키는 것을 특징으로 하는 제조방법.Acid and anhydrous formula selected from carbon monoxide, hydrofluoric acid (HF) and hydrochloric acid (HCl) (Wherein R is an alkyl group having up to 20 carbon atoms and R 'is an alkyl having 2 to 20 carbon atoms) and a carbon source having at least one double bond capable of forming an acylium anion with the ester The amount required to convert the mixture of the acylium anion product, which is a reaction product of an organic compound reactive with carbon monoxide selected from olefins having 20 embroidery, into esterification by converting the total amount of the acylium anion in the mixture into carboxylic acid esters. The initial ratio of the anhydrous acid to the acylium anion product at a temperature of 20 ° to 150 ° C. and a pressure of 1 bar (14.7 psia) to 340 bar (5000 psia) with an alcohol of A method for producing esters, characterized by esterification in the range of 0.01 to 95.5 parts by weight. 상기 제1항기재에 있어서, 상기 유기 화합물이 이소프로필 이소부티르산염, 에틸 이소부티르산염, 이소프로필 프로피온산염 및 에틸 프로피온산염으로 구성된 군에서 선택됨을 특징으로 하는 제조방법.The method according to claim 1, wherein the organic compound is selected from the group consisting of isopropyl isobutyrate, ethyl isobutyrate, isopropyl propionate and ethyl propionate. 상기 제1항기재에 있어서, 상기 유기화합물이 함께 아실리움 음이온생성물을 생성할 수있는 한개 이상의 이중결합을 갖는 탄소원자수 20개까지의 올레핀임을 특징으로 하는 제조방법.The method according to claim 1, wherein the organic compound is an olefin having up to 20 carbon atoms having at least one double bond capable of forming an acylium anion product together. 상기 제1항기재에 있어서, 상기 올레호이 에틸렌임을 특징으로 하는 제조방법.The method according to claim 1, wherein the oleho is ethylene. 상기 제1항기재에 있어서, 상기 올레핀이 프로필렌임을 특징으로 하는 제조방법.The method according to claim 1, wherein the olefin is propylene. 상기 제1항, 제2항, 제3항, 제4항 또는 제5항기재에 있어서, 상기 알코올이 메탄올임을 특징으로 하는 제조방법.The method according to claim 1, 2, 3, 4 or 5, wherein the alcohol is methanol. 상기 제6항기재에 있어서, 상기 생성된 카르복실산 에스테르를 함유하는 에스테르화 반응생성물의 혼합물로부터 1내지 100%의 무수산을 분리하고, 이들 분리된 무수산을 일산화탄소 및 유기화합물과 반응시켜 보다 많은 아실리움 음이온생성물을 제조하기 위하여 재순환시키는 것을 특징으로 하는 제조방법.The method according to claim 6, wherein 1 to 100% of anhydrous acid is separated from the mixture of the esterification reaction product containing the produced carboxylic acid ester, and the separated anhydrous acid is reacted with carbon monoxide and an organic compound. A process for recycling a large number of acylium anion products. 상기 제6항기재에 있어서, 상기 에스테르화 반응생성물의 혼합물로부터 카르복실산 에스테르 1내지 100%를 분리시키는 단계와 이들로부터 카르복실산 에스테르를 분리시킨 후 잔유하는 에스테르화반응생성물의 혼합물 1내지 100%를 재순환시켜 보다 많은 아실리움 음이온생성물을 제조하는 단계의 공정을 더 추가시킴을 특징으로 하는 제조방법.The method according to claim 6, wherein 1 to 100% of the carboxylic acid ester is separated from the mixture of the esterification reaction product and 1 to 100 mixture of the esterification reaction product remaining after separating the carboxylic acid ester therefrom. Recycling the% further to produce more acylium anion products. 상기 제6항기재에 있어서, 무수산이 HF임을 특징으로 하는 제조방법.The method according to claim 6, wherein the anhydrous acid is HF. 상기 제9항기재에 있어서, 아실리움 음이온생성물(불화아실)에 대한 무수 HF의 초기양이 아실리움 음이온생성물(불화아실)의 90내지 10중량부에 대해 무수 HF의 10내지 90중량부임을 특징으로 하는 제조방법.The method according to claim 9, wherein the initial amount of anhydrous HF to the acyl anion product (acyl fluoride) is 10 to 90 parts by weight of anhydrous HF relative to 90 to 10 parts by weight of the acyl anion product (acyl fluoride). Manufacturing method. 상기 제7항기재에 있어서, 무수산이 HF임을 특징으로 하는 제조방법.The method according to claim 7, wherein the anhydrous acid is HF. 상기 제8항기재에 있어서, 상기 무수산이 HF임을 특징으로 하는 제조방법.The method according to claim 8, wherein the anhydrous acid is HF. 상기 제1항기재에 있어서, 상기 혼합물이 일산화탄소, 무수 HF 및 불화이소부티릴로 조성되며, 상기 알코올이 메탄올이며, 초기에 가한 메탄올의 양이 불화이소부티릴의 70내지 99%이며, 에스테르화되어질 상기 혼합물에서 무수 HF의 양은 불화이소부티릴 1몰에 대해서 무수 HF 10내지 20몰의 범위내로 사용함을 특징으로 하는 제조방법.The method of claim 1, wherein the mixture is composed of carbon monoxide, anhydrous HF, and isobutyryl fluoride, wherein the alcohol is methanol, and the amount of methanol initially added is 70 to 99% of isobutyryl fluoride, to be esterified. The amount of anhydrous HF in the mixture is used in the range of 10 to 20 moles of anhydrous HF per 1 mole of isobutyryl fluoride. 상기 제13항기재에 있어서, 상기 에스테르화반응 3.3바아(50ptia)내지 6.7바아(100psia)의 압력범위 및 40℃내지 70℃의 온도범위내에서 수행함을 특징으로 하는 제조방법.The method according to claim 13, wherein the esterification reaction is carried out within a pressure range of 3.3 bar (50 ptia) to 6.7 bar (100 psia) and a temperature range of 40 ℃ to 70 ℃. 상기 제14항기재에 있어서, 상기 에스테르화반응생성 혼합물로부터 생성된 이소부티르산의 80내지 100%를 분리시키기 위하여 증류공정을 추가시킴을 특징으로 하는 제조방법.The method according to claim 14, wherein a distillation process is added to separate 80 to 100% of isobutyric acid produced from the esterification reaction mixture. 상기 제15항기재에 있어서, 증류 및 에스테르화반응이 동시에 일어남을 특징으로 하는 제조방법.The process according to claim 15, wherein distillation and esterification occur simultaneously. 상기 제16항기재에 있어서, 메틸이소부티르산의 90내지 100%를 상기 에스테르화반응생성물의 혼합물로부터 분리시킴을 특징으로 하는 제조방법.The process according to claim 16, wherein 90 to 100% of methylisobutyric acid is separated from the mixture of the esterification reaction product. 아실리움 음이온생성물로 구성되는 혼합물과 이 아실리움 음이온을 메틸 프로피온산염 및 메틸 이소부티르산염으로 구성된 군중에서 선택된 대응하는 에스테르로 에스테르화시키는 데요구되는 양보다 적은 양의 메탄올을 상기 카르복실산 에스테르가 생성되고 상기 음이온으로부터 상기 산이 재생되는 무수조건하에서 에스테르화시키고;The carboxylic acid ester generates less than the amount of methanol required to esterify the mixture consisting of the acylium anion product and the corresponding acyl anion with a corresponding ester selected from the group consisting of methyl propionate and methyl isobutyrate. And esterified under anhydrous conditions in which the acid is regenerated from the anion; 상기 에스테르를 분리하여, 증기상의 에스테르를 메틸 아크릴산염 또는 메틸 메타클리산염의 대응하는 불포화카르복실산 에스테르로 옥시탈수소화시키며;The esters are separated to oxydehydrogenate the vaporized esters to the corresponding unsaturated carboxylic esters of methyl acrylate or methyl methacrylate; 상기 아실리움 음이온생성물은 일산화탄소, 에틸렌 및 프로필렌으로 구성된 군중에서 선택된 올레핀 및 무수산을 아실리움 음이온이 생성되는 조건하에서 반응시킴으로써 생성되며; 상기 무수산은 불화수소(HF) 및 염화수소(HCl)로 구성된 군중에서 선택함을 특징으로 하는 메틸 아크릴산염 및 메틸 메타클리산염으로 구성된 군중에서 선택된 불포화카르복실산 에스테르를 제조하는 방법.The acylium anion product is produced by reacting an olefin and an anhydride selected from the group consisting of carbon monoxide, ethylene and propylene under conditions in which an acylium anion is produced; Wherein said anhydrous acid is selected from the group consisting of hydrogen fluoride (HF) and hydrogen chloride (HCl). The method of preparing an unsaturated carboxylic acid ester selected from the group consisting of methyl acrylate and methyl methacrylate. 상기 제18항기재에 있어서, 상기 무수산이 불화수소임을 특징으로 하는 제조방법.The method according to claim 18, wherein the anhydrous acid is hydrogen fluoride. 상기 제19항기재에 있어서, 상기 올레핀이 프로필렌임을 특징으로 하는 제조방법.The method according to claim 19, wherein the olefin is propylene. 상기 제18항, 19항 또는 20항기재에 있어서, 상기 옥시탈수소반응의 단계에 실험식 Fe Px Oz (여기서 1원자의 Fe에 대해서 x는 0.25내지 3.5원자의 인을 표시하며, z는 본 촉매의 원자가충 족시키는데 요구된 산소 원자수를 나타냄)로 정의된 철, 인, 및 산소로 조성된 촉매를 사화함을 특징으로 하는 제조방법.The method according to claim 18, 19 or 20, wherein in the step of the oxydehydrogenation reaction, the formula Fe Px Oz (where x represents 0.25 to 3.5 atoms of phosphorus for 1 atom of Fe, and z represents Producing a catalyst composed of iron, phosphorus, and oxygen, defined as the number of oxygen atoms required to satisfy the atom. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR8202510A 1981-07-10 1982-06-04 Process for the preparation of carboxylic esters from isobutyryl fluoride formed by carbonylation KR850001915B1 (en)

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