KR950032049A - Method for preparing 1-hydroxycyclohexyl phenyl ketone - Google Patents

Method for preparing 1-hydroxycyclohexyl phenyl ketone Download PDF

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KR950032049A
KR950032049A KR1019940010315A KR19940010315A KR950032049A KR 950032049 A KR950032049 A KR 950032049A KR 1019940010315 A KR1019940010315 A KR 1019940010315A KR 19940010315 A KR19940010315 A KR 19940010315A KR 950032049 A KR950032049 A KR 950032049A
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phenyl ketone
hydroxycyclohexyl phenyl
producing
reacting
hydroxycyclohexyl
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KR0129408B1 (en
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신한섭
차응호
이영춘
민경세
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라공묵
코오롱유화 주식회사
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
    • C07C49/245—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings
    • 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
    • C07C45/63—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 introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
    • C07C49/252—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings and other rings
    • 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
    • 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
    • C07C2527/06—Halogens; Compounds thereof
    • C07C2527/08—Halides
    • C07C2527/10—Chlorides
    • C07C2527/11—Hydrogen chloride

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

본 발명은 1-히드록시시클로헥실 페닐 케톤의 제조 방법에 관한 것이다. 좀 더 구체적으로, 본 발명은 불포화 화합물의 광중합반응 및 폴리올레핀의 광화학적 가교반응의 광개시제로서 사용되는 1-히드록시시클로헥실 페닐 케톤을 간편하게 제조할 수 있는 방법에 관한 것이다. 본 발명의 1-히드록시시클로헥실 페닐 케톤의 제조방법은 시클로헥실 페닐 케톤에 무기산 촉매 및 SOxY(전기식에서, x는 1또는 2의 정수이며; 및 Y는 할로겐족 원소이다.)로 표시되는 할로겐화 황산화물을 가하고 반응시켜 1-할로로시클로헥실 페닐 케톤을 제조하는 공정; 및, 전기공정에서 수득한 1-할로로시클로헥실 페닐 케톤에 금속히드록사이드 수용액 및 상전이 촉매를 가하고 반응시키는 공정을 포함한다. 본 발명의 제조방법에 의해 반응시간을 단축시킬 수 있으며, 간편하게 고수율로 불포화 화합물의 광중합반응 및 폴리올레핀의 광화학적 가교반응의 광개시제 등으로 유용한 1-히드록시시클로헥실 페닐 케톤을 제조할 수 있다는 것이 확인되었다.The present invention relates to a process for the preparation of 1-hydroxycyclohexyl phenyl ketone. More specifically, the present invention relates to a process for the simple production of 1-hydroxycyclohexyl phenyl ketones used as photoinitiators for photopolymerization of unsaturated compounds and photochemical crosslinking of polyolefins. The method for producing 1-hydroxycyclohexyl phenyl ketone of the present invention is a halogenated sulfuric acid represented by cyclohexyl phenyl ketone as an inorganic acid catalyst and SOxY (wherein x is an integer of 1 or 2; and Y is a halogen group element). Adding a cargo and reacting to prepare 1-halocyclohexyl phenyl ketone; And a step of adding and reacting an aqueous metal hydroxide solution and a phase transfer catalyst to the 1-halocyclohexyl phenyl ketone obtained in the electrical process. According to the production method of the present invention, the reaction time can be shortened and 1-hydroxycyclohexyl phenyl ketone useful as a photoinitiator for photopolymerization reaction of an unsaturated compound and photochemical crosslinking reaction of a polyolefin can be easily produced in high yield. Confirmed.

Description

1-히드록시시클로헥실 페닐 케톤의 제조방법Method for preparing 1-hydroxycyclohexyl phenyl ketone

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

Claims (13)

(i)시클로헥실 페닐 케톤에 무기산 촉매 및 SOxY(전기식에서, x는 1또는 2의 정수이며; 및 y는 할로겐족 원소이다.)로 표시되는 할로겐화 황산화물을 가하고 반응시켜 1-히드록시시클로헥실 페닐 케톤을 제조하는 공정; 및(ii)전기공정에서 수득한 1-할로로시클로헥실 페닐 케톤에 금속히드록사이드 수용액 및 상전이 촉매를 가하고 반응시키는 공정을 포함하는 1-히드록시시클로헥실 페닐 케톤에 금속히드록사이드 수용액 및 상전이 촉매를 가하고 반응시키는 공정을 포함하는 1-히드록시시클로헥실 페닐 케톤의 제조방법.(i) 1-hydroxycyclohexyl phenyl by adding and reacting a halogenated sulfur oxide represented by an inorganic acid catalyst and SOxY (wherein x is an integer of 1 or 2; and y is a halogen group element) to a cyclohexyl phenyl ketone. Preparing a ketone; And (ii) adding and reacting the metal hydroxide aqueous solution and the phase transfer catalyst to the 1-halocyclohexyl phenyl ketone obtained in the electrical process, and reacting the metal hydroxide aqueous solution and phase transition to the 1-hydroxycyclohexyl phenyl ketone. A method for producing 1-hydroxycyclohexyl phenyl ketone comprising the step of adding and reacting a catalyst. 제1항에 있어서, 상전이 촉매는 하기 일반긱(I)로 표시되는 화합물인 것을 특징을 하는 1-히드록시시클로헥실 페닐 케톤의 제조방법.The process for producing 1-hydroxycyclohexyl phenyl ketone according to claim 1, wherein the phase transfer catalyst is a compound represented by the following general formula (I). (Ra)(Rb)(Rc)(Rd)N+Z-(I) (R a) (R b) (R c) (R d) N + Z - (I) 상기 식에서, Ra,R,bRc및Rd동일하거나 상이한 직쇄형 또는 측쇄형의 탄소수 3내지 20개의 알킬기 또는 벤질기이며; 및, Z는 할로겐족 원소이다.In which R a, R, b R c and R d are the same or different straight or branched C 3-20 alkyl or benzyl groups; And Z is a halogen group element. 제1항에 있어서, 무기산 촉매로는 황산 및 염산으로 이루어진 그룹으로 부터 선택된 1종 이상을 사용하는 것을 특징으로 하는 1-히드록시시클로헥실 페닐 케톤의 제조방법.The method for preparing 1-hydroxycyclohexyl phenyl ketone according to claim 1, wherein at least one selected from the group consisting of sulfuric acid and hydrochloric acid is used as the inorganic acid catalyst. 제1항에 있어서, 무기산 촉매의 첨가량은 시클로헥실 페닐 케톤 1mol에 대하여 0.01 내지 0.2mol인 것을 특징으로 하는 1-히드록시시클로헥실 페닐 케톤의 제조방법.The method for producing 1-hydroxycyclohexyl phenyl ketone according to claim 1, wherein the amount of the inorganic acid catalyst added is 0.01 to 0.2 mol based on 1 mol of the cyclohexyl phenyl ketone. 제1항에 있어서, 할로겐화 황산화물로는 설퓨릴 클로라이드 밑 티오닐 클로라이드로 이루어진 그룹으로 부터 선택된 1종이상을 사용하는 것을 특징으로 하는 1-히드록시시클로헥실 페닐 케톤의 제조방법.The method for preparing 1-hydroxycyclohexyl phenyl ketone according to claim 1, wherein the halogenated sulfur oxide is one or more selected from the group consisting of thionyl chloride under sulfuryl chloride. 제1항에 있어서, 할로겐화 황산화물의 첨가량은 시클로헥실 페닐 케톤 1mol에 대하여 1 내지 2mol인 것을 특징으로 하는 1-히드록시시클로헥실 페닐 케톤의 제조방법.The method for producing 1-hydroxycyclohexyl phenyl ketone according to claim 1, wherein the amount of halogenated sulfur oxide added is 1 to 2 mol based on 1 mol of cyclohexyl phenyl ketone. 제1항에 있어서, 시클로헥실 페닐 케톤과 할로겐화 황산화물은 40 내지80℃의 반응 온도에서 3 내지 5시간 동안 반응시키는 것을 특징으로 하는 1-히드록시시클로헥실 페닐 케톤의 제조방법.The method for preparing 1-hydroxycyclohexyl phenyl ketone according to claim 1, wherein the cyclohexyl phenyl ketone and the halogenated sulfur oxide are reacted at a reaction temperature of 40 to 80 ° C. for 3 to 5 hours. 제1항에 있어서, 금속 히드록사이드는 알칼리 금속의 히드록사이드 또는 알칼리토금속의 히드록사이드인 것을 특징으로 하는 1-히드록시시클로헥실 페닐 케톤의 제조방법.The method for producing 1-hydroxycyclohexyl phenyl ketone according to claim 1, wherein the metal hydroxide is a hydroxide of an alkali metal or a hydroxide of an alkaline earth metal. 제1항에 있어서, 금속 히드록사이드의 첨가량은 1-할로로시클로헥실 페닐 케톤 1mol에 대하여 1 내지 2mol인 것을 특징으로 하는 1-히드록시시클로헥실 페닐 케톤의 제조방법.The method for producing 1-hydroxycyclohexyl phenyl ketone according to claim 1, wherein the addition amount of the metal hydroxide is 1 to 2 mol based on 1 mol of 1-halocyclohexyl phenyl ketone. 제1항 또는 제2항에 있어서, 상전이 촉매로는 테트라메틸암모늄 클로라이드, 테트라메틸암모늄 브로마이드, 테트라메틸암모늄 이오다이드, 테트라부틸암모늄 클로라이드, 테트라부틸암모늄 브로마이드 및 테트라부틸암모늄 이오다이드로 이루어진 그룹으로부터 선택된 1종 이상을 사용하는 것을 특징으로 하는 1-히드록시시클로헥실 페닐 케톤의 제조방법.The method of claim 1 or 2, wherein the phase transfer catalyst is selected from the group consisting of tetramethylammonium chloride, tetramethylammonium bromide, tetramethylammonium iodide, tetrabutylammonium chloride, tetrabutylammonium bromide and tetrabutylammonium iodide. A process for producing 1-hydroxycyclohexyl phenyl ketone, characterized in that at least one selected is used. 제1항에 있어서, 상전이 촉매의 첨가량은 1-할로로시클로헥실 페닐 케톤 1mol에 대하여 0.001 내지 0.01mol인 것을 특징으로 하는 1-히드록시시클로헥실 페닐 케톤의 제조방법The method for preparing 1-hydroxycyclohexyl phenyl ketone according to claim 1, wherein the amount of the phase transfer catalyst is 0.001 to 0.01 mol based on 1 mol of 1-halocyclohexyl phenyl ketone. 제1항에 있어서, 1-할로로시클로헥실 페닐 케톤과 금속 히드록사이드 수용액은 50 내지 100℃의 반응온도에서 4 내지 5시간 동안 반응시키는 것을 특징으로 하는 1-히드록시시클로헥실 페닐 케톤의 제조방법The preparation of 1-hydroxycyclohexyl phenyl ketone according to claim 1, wherein the 1-halocyclohexyl phenyl ketone and the metal hydroxide aqueous solution are reacted at a reaction temperature of 50 to 100 ° C. for 4 to 5 hours. Way 시클로헥실 페닐 케톤에 무기산 촉매 및 SOxY(전기식에서, x는 1또는 2의 정수이며; 및 Y는 할로겐족 원소이다.)로 표시되는 할로겐화 황산화물을 가하고 반응시켜 1-히드록시시클로헥실 페닐 케톤을 제조한 다음, 1-히드록시시클로헥실 페닐 케톤에 금속 히드록사이드 수용액 및 상전이 촉매를 가하고 반응시켜 제조한 1-히드록시시클로헥실 페닐 케톤To the cyclohexyl phenyl ketone, an inorganic acid catalyst and a halogenated sulfur oxide represented by SOxY (wherein x is an integer of 1 or 2; and Y is a halogen group element) are added and reacted to prepare 1-hydroxycyclohexyl phenyl ketone. Then, 1-hydroxycyclohexyl phenyl ketone prepared by adding a metal hydroxide aqueous solution and a phase transfer catalyst to 1-hydroxycyclohexyl phenyl ketone and reacting the same ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019940010315A 1994-05-11 1994-05-11 Process for preparation of 1-hydroxycyclohexylphenyl ketone KR0129408B1 (en)

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