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KR920703482A - Selective diethylation of naphthalene with 2,6-diethylnaphthalene - Google Patents

Selective diethylation of naphthalene with 2,6-diethylnaphthalene

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KR920703482A
KR920703482A KR1019920700896A KR920700896A KR920703482A KR 920703482 A KR920703482 A KR 920703482A KR 1019920700896 A KR1019920700896 A KR 1019920700896A KR 920700896 A KR920700896 A KR 920700896A KR 920703482 A KR920703482 A KR 920703482A
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diethylnaphthalene
naphthalene
ethylnaphthalene
ratio
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디. 펠만 제레
마씨아니 파스칼
엑스너 헤르베르트
알. 웬트렉 폴
제이. 색스톤 로버트
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원본미기재
캐탈리타카 인코오퍼레이티드
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Abstract

내용 없음No content

Description

나프탈렌을 2,6-디에틸나프탈렌으로 선택적으로 디에틸화시키는 방법Selective diethylation of naphthalene with 2,6-diethylnaphthalene

[도면의 간단한 설명][Brief Description of Drawings]

이 실시예는 평행에서 전체 DEN아이소머중의 2, 6/2, 7비와 2, 6퍼센트의 값을 보여준다. 실리카/알루미나로 상기 방법으로 시행한 실험은 나프탈렌에 에틸화에 대해서 이들 값이 1.0 과 각각 17% 내지 22%라는 것여 주었다(제1도).This example shows 2, 6/2, 7 ratios and 2, 6 percent of the total DEN isomers in parallel. Experiments conducted with this method with silica / alumina gave that these values were 1.0 and 17% to 22%, respectively, for ethylation in naphthalene (FIG. 1).

제2도는 모든 이들 촉매를 사용한 디에틸화 반응의 결과비교를 보여준다. ZSM-는 2, 6/2, 7에 대한 최초 값으로 예리한 선택도가 1. 7이라는 것을 명백히 보여준다.2 shows a comparison of the results of the deethylation reaction with all these catalysts. ZSM- is the first value for 2, 6/2, and 7 clearly showing a sharp selectivity of 1. 7.

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

Claims (42)

a. 큰 기공구멍 직경이 5.6Å 내지 7.0Å사이에 있는 산성 제올라이트 촉매를 포함하는 알킬화반응기에 나프탈렌 또는 2-에틸나프탈렌 및 에틸화제를 제공하는 단계, b. 상기 나프탈렌 또는 2-에틸나프탈렌의 적어도 일부를 2,6-디에틸나프탈렌으로 전환시키기에 충분한 조건으로, 촉매의 존재하에 상기 알킬화 반응기 중에서 나프탈렌 또는 2-에틸나프탈렌을 에틸화제와 반응시키는 단계로 구성된 것을 특징으로 하는 2,6-디에틸나프탈렌이 풍부한 디에틸나프탈렌의 제조방법.a. Providing a naphthalene or 2-ethylnaphthalene and ethylating agent to an alkylation reactor comprising an acidic zeolite catalyst having a large pore pore diameter between 5.6 kPa and 7.0 kPa, b. Reacting the naphthalene or 2-ethylnaphthalene with an ethylating agent in the alkylation reactor in the presence of a catalyst, under conditions sufficient to convert at least a portion of the naphthalene or 2-ethylnaphthalene to 2,6-diethylnaphthalene. A process for producing diethylnaphthalene, which is rich in 2,6-diethylnaphthalene. 제1항에 있어서, 산성 제올라이트가 ZSM-12, EU-1 및 SAPO-11로부터 선택되는 것을 특징으로 하는 방법.The method of claim 1 wherein the acidic zeolite is selected from ZSM-12, EU-1 and SAPO-11. 제1항에 있어서, 에틸화제가 에틸렌, 에탄올, 에틸에테르 및 염화에틸로부터 선택되는 것을 특징으로 하는 방법.The process of claim 1 wherein the ethylating agent is selected from ethylene, ethanol, ethyl ether and ethyl chloride. 제3항에 있어서, 에틸화제가 에틸렌을 포함하는 것을 특징으로 하는 방법.The method of claim 3 wherein the ethylating agent comprises ethylene. 제2항에 있어서, 디에틸화된 아이소머에서 2,6-디에틸나프탈렌의 퍼센트가 20%이상인 것을 특징으로 하는 방법.The method of claim 2 wherein the percentage of 2,6-diethylnaphthalene in the diethylated isomer is at least 20%. 제5항에 있어서, 반응이 2,6-디에틸나프탈렌 및 2,7-디에틸나프탈렌 양자모두를 제조하고 2,6/2,7아이소머의 비가 1이상인 것을 특징으로 하는 방법.6. The process of claim 5 wherein the reaction produces both 2,6-diethylnaphthalene and 2,7-diethylnaphthalene and the ratio of 2,6 / 2,7 isomer is at least one. 제2항에 있어서, 상기 촉매의 Si/Al비가 약 5 내지 2000사이를 나타내는 것을 특징으로 하는 방법.3. The method of claim 2, wherein the Si / Al ratio of the catalyst is between about 5 and about 2000. 제7항에 있어서, 상기 촉매의 Si/Al비가 약 10 내지 1000사이를 나타내는 것을 특징으로 하는 방법.8. The method of claim 7, wherein the Si / Al ratio of the catalyst is between about 10 and 1000. 제8항에 있어서, 상기 촉매의 Si/Al비가 약 20 내지 500사이를 나타내는 것을 특징으로 하는 방법.The method of claim 8, wherein the Si / Al ratio of the catalyst is between about 20 and 500. 10. 제9항에 있어서, 상기 촉매를 400℃ 내지 1000℃범위의 온도에서 하소하는 것을 특징으로 하는 방법.10. The process of claim 9, wherein the catalyst is calcined at a temperature in the range of 400 ° C to 1000 ° C. 제2항에 있어서, IIIA, IVA, VA족의 할로겐, 수소화 또는 유기 유도체로 구성된 군에서 선택된 비활성화제가 상기 촉매를 접촉시킴으로써 상기 제올라이트 촉매의 외부 표면상의 산성 부위를 비활성시키는 것을 특징으로 하는 방법.3. The method of claim 2, wherein an inactivator selected from the group consisting of halogen, hydrogenated or organic derivatives of groups IIIA, IVA, VA, inactivates the acidic sites on the outer surface of the zeolite catalyst by contacting the catalyst. 제2항에 있어서, 상기 제올라이트 촉매의 외부 표면상의 산성 부위를 이하의 단계로 이루어진 방법으로 비활성화시키는 것을 특징으로 하는 방법.The method according to claim 2, wherein the acidic sites on the outer surface of the zeolite catalyst are deactivated by the following steps. a. 상기 촉매의 결정내 빈 기공 부피를 탄화수소로 충전하여 내부적으로 보호된 촉매를 얻는 단계, b. 결정내 기공내에 포함된 탄화수소에 불용성인 수성 산 또는 착화제로 상기 내부적으로 보호된 촉매를 처리하는 단계, c. 상기 탄화수소를 제거하여 상기 촉매를 회수하는 단계.a. Filling the empty pore volume in the crystal of the catalyst with a hydrocarbon to obtain an internally protected catalyst, b. Treating said internally protected catalyst with an aqueous acid or complexing agent that is insoluble in the hydrocarbons contained within the pores in the crystals, c. Recovering the catalyst by removing the hydrocarbon. 제2항에 있어서, 외부 산성부위를 예비코우크스화하여 비활성화시키는 것을 특징으로 하는 방법.The method of claim 2, wherein the external acidic site is precoked to inactivate it. 제2항에 있어서, 2,6-디에틸나프탈렌을 산화시켜 2,6-디카르복시나프탈렌을 제조하는 단계를 더 포함하는 것을 특징으로 하는 방법.The method of claim 2, further comprising oxidizing 2,6-diethylnaphthalene to produce 2,6-dicarboxynaphthalene. a. 산성 제올라이트 ZSM-12를 포함하는 알킬화반응기에 나프탈렌 또는 2-에틸나프탈렌 및 에틸화제를 제공하는 단계, b. 상기 나프탈렌 또는 2-에틸나프탈렌의 적어도 일부를 2,6-디에틸나프탈렌으로 전환시키기에 충분한 조건으로, 촉매의 존재하에 상기 알킬화 반응기중에서 나프탈렌 또는 2-에틸나프탈렌을 에틸화제와 반응시키는 단계로 구성된 것을 특징으로 하는 2,6-디에틸나프탈렌이 풍부한 디에틸나프탈렌의 제조방법.a. Providing naphthalene or 2-ethylnaphthalene and an ethylating agent to an alkylation reactor comprising an acidic zeolite ZSM-12, b. Consisting of reacting naphthalene or 2-ethylnaphthalene with an ethylating agent in the alkylation reactor in the presence of a catalyst, under conditions sufficient to convert at least a portion of the naphthalene or 2-ethylnaphthalene to 2,6-diethylnaphthalene. A process for producing diethylnaphthalene, which is rich in 2,6-diethylnaphthalene. 제15항에 있어서, 에틸화제가 에틸렌, 에탄올, 에틸에테르 및 염화에틸로 부터 선택되는 것을 특징으로 하는 방법.The process of claim 15 wherein the ethylating agent is selected from ethylene, ethanol, ethyl ether and ethyl chloride. 제16항에 있어서, 에틸화제가 에틸렌을 포함하는 것을 특징으로 하는 방법.The method of claim 16 wherein the ethylating agent comprises ethylene. 제15항에 있어서, 디에틸화된 아이소머에서 2,6-디에틸나프탈렌의 퍼센트가 20%이상인 것을 특징으로 하는 방법.16. The method of claim 15, wherein the percent of 2,6-diethylnaphthalene in the diethylated isomer is at least 20%. 제18항에 있어서, 반응이 2,6-디에틸나프탈렌 및 2,7-디에틸나프탈렌 양자모두를 제조하고 2,6/2,7아이소머의 비가 1이상인 것을 특징으로 하는 방법.19. The method of claim 18, wherein the reaction produces both 2,6-diethylnaphthalene and 2,7-diethylnaphthalene and the ratio of 2,6 / 2,7 isomer is at least one. 제15항에 있어서, 상기 촉매의 Si/A1비가 약 10 내지 1000사이를 나타내는 것을 특징으로 하는 방법.16. The method of claim 15, wherein the Si / A1 ratio of the catalyst is between about 10 and 1000. 제20항에 있어서, 상기 촉매의 Si/Al비가 약 20 내지 500사이를 나타내는 것을 특징으로 하는 방법.21. The method of claim 20, wherein the Si / Al ratio of the catalyst is between about 20 and 500. 제21항에 있어서, 상기 촉매를 400℃ 내지 1000℃범위의 온도에서 하소하는 것을 특징으로 하는 방법.The method of claim 21, wherein the catalyst is calcined at a temperature in the range of 400 ° C. to 1000 ° C. 23. 제15항에 있어서, IIIA, IVA, IVB 및 VA족의 할로겐, 수소화 또는 유기 유도체로 구성된 군에서 선택된 비활성화제와 상기 촉매를 접촉시킴으로써 상기 제올라이트 촉매의 외부 표면상의 산성 부위를 비활성시키는 것을 특징으로 하는 방법.16. The acidic site on the outer surface of the zeolite catalyst according to claim 15, characterized in that the catalyst is contacted with an inactivating agent selected from the group consisting of halogen, hydrogenated or organic derivatives of groups IIIA, IVA, IVB and VA. Way. 제15항에 있어서, 상기 제올라이트 촉매의 외부 표면상의 산성 부위를 이하의 단계로 이루어진 방법으로 비활성화시키는 것을 특징으로 하는 방법.The method according to claim 15, wherein the acidic sites on the outer surface of the zeolite catalyst are deactivated by the following steps. a. 상기 촉매의 결정내 빈 기공 부피를 탄화수소로 충전하여 내부적으로 보호된 촉매를 얻는 단계, b. 결정내 기공내에 포함된 탄화수소에 불용성인 수성 산 또는 산화제로 상기 내부적으로 보호된 촉매를 처리하는 단계, c. 상기 탄화수소를 제거하여 상기 촉매를 회수하는 단계.a. Filling the empty pore volume in the crystal of the catalyst with a hydrocarbon to obtain an internally protected catalyst, b. Treating said internally protected catalyst with an aqueous acid or oxidant insoluble in hydrocarbons contained within pores in said crystals, c. Recovering the catalyst by removing the hydrocarbon. 제15항에 있어서, 외부 산성부위를 예비코우크스화하여 비활성화시키는 것을 특징으로 하는 방법.16. The method of claim 15, wherein the external acidic site is precoked to inactivate it. 제15항에 있어서, 상기 촉매의 입자 직경이 4.0㎛이하인 것을 특징으로 하는 방법.The method according to claim 15, wherein the catalyst has a particle diameter of 4.0 mu m or less. 제26항에 있어서, 입자 직경이 0.1㎛ 내지 3.75㎛사이인 것을 특징으로 하는 방법.The method of claim 26, wherein the particle diameter is between 0.1 μm and 3.75 μm. 제15항에 있어서, 2,6-디메틸나프탈렌을 산화시켜 2,6-디카르복시나프탈렌을 제조하는 단계를 부가적으로 포함하는 것을 특징으로 하는 방법.The method of claim 15, further comprising oxidizing 2,6-dimethylnaphthalene to produce 2,6-dicarboxynaphthalene. a. 기공구멍 치수가 5.1 내지 7.0Å인 형상 선택적 촉매로 이루어진 촉매를 포함하는 알킬화반응기에 나프탈렌 또는 2-에틸나프탈렌 및 에틸화제를 제공하는 단계, b. 상기 나프탈렌 또는 2-에틸나프탈렌의 적어도 일부를 2,6-디에틸나프탈렌의 퍼센트가 20%이상인 스트림으로 전환시키기에 충분한 조건으로, 촉매의 존재하에 상기 알킬화반응기 중에서 나프탈렌 또는 2-에틸나프탈렌을 에틸화제와 반응시키는 단계로 구성된 것을 특징으로 하는 2,6-디에틸나프탈렌이 풍부한 디에틸나프탈렌의 제조방법.a. Providing a naphthalene or 2-ethylnaphthalene and an ethylating agent to an alkylation reactor comprising a catalyst consisting of a shape-selective catalyst having a pore pore size of 5.1 to 7.0 microns; Under conditions sufficient to convert at least a portion of the naphthalene or 2-ethylnaphthalene to a stream having a percentage of 2,6-diethylnaphthalene of at least 20%, the naphthalene or 2-ethylnaphthalene is ethylated in the alkylation reactor in the presence of a catalyst. A method for producing diethylnaphthalene rich in 2,6-diethylnaphthalene, characterized in that the step of reacting with. 제29항에 있어서, 에틸화재가 에틸렌, 에탄올, 에틸에테르 및 염화에틸로 부터 선택되는 것을 특징으로 하는 방법.30. The process of claim 29 wherein the ethylenate is selected from ethylene, ethanol, ethylether and ethyl chloride. 제30항에 있어서, 에틸화제가 에틸렌을 포함하는 것을 특징으로 하는 방법.31. The method of claim 30, wherein the ethylating agent comprises ethylene. 제29항에 있어서, 반응이 2,6-디에틸나프탈렌 및 2,7-디에틸나프탈렌 양자모두를 제조하고 2,6/2,7아이소머의 비가 1이상인 것을 특징으로 하는 방법.30. The method of claim 29, wherein the reaction produces both 2,6-diethylnaphthalene and 2,7-diethylnaphthalene and the ratio of 2,6 / 2,7 isomer is at least one. 제29항에 있어서, 상기 촉매의 실리카/알루미나 비가 약 5 내지 2000사이를 나타내는 것을 특징으로 하는 방법.30. The method of claim 29, wherein the silica / alumina ratio of the catalyst is between about 5 and 2000. 제33항에 있어서, 상기 촉매의 실리카/알루미나 비가 약 10 내지 1000사이를 나타내는 것을 특징으로 하는 방법.34. The method of claim 33, wherein the silica / alumina ratio of the catalyst is between about 10 and 1000. 제34항에 있어서, 상기 촉매의 실리카/알루미나 비가 약 20 내지 500사이를 나타내는 것을 특징으로 하는 방법.35. The method of claim 34, wherein the silica / alumina ratio of the catalyst is between about 20 and 500. 제29항에 있어서, 상기 촉매를 400℃ 내지 1000℃범위의 온도에서 하소하는 것을 특징으로 하는 방법.30. The method of claim 29, wherein the catalyst is calcined at a temperature in the range of 400 ° C to 1000 ° C. 제29항에 있어서, IIIA, IVA, IVB족 및 VA족의 할로겐, 수소화 또는 유기 유도체로 구성된 군에서 선택된 비활성화제와 상기 촉매를 접촉시킴으로써 상기 제올라이트 촉매의 외부 표면상의 산성 부위를 비활성시키는 것을 특징으로 하는 방법.30. The acidic site according to claim 29, wherein said catalyst is inactivated by contacting said catalyst with an inactivating agent selected from the group consisting of halogen, hydrogenated or organic derivatives of groups IIIA, IVA, IVB and VA. How to. 제29항에 있어서, 상기 제올라이트 촉매의 외부 표면상의 산성 부위를 이하의 단계로 이루어진 방법으로 비활성화시키는 것을 특징으로 하는 방법.30. The method of claim 29, wherein the acidic sites on the outer surface of the zeolite catalyst are deactivated by the following steps. a. 상기 촉매의 결정내 빈 기공 부피를 탄화수소로 충전하여 내부적으로 보호된 촉매를 얻는 단계, b. 결정내 기공내에 포함된 탄화수소에 불용성인 수성 산 또는 산화제로 상기 내부적으로 보호된 촉매를 처리하는 단계, c. 상기 탄화수소를 제거하여 상기 촉매를 회수하는 단계.a. Filling the empty pore volume in the crystal of the catalyst with a hydrocarbon to obtain an internally protected catalyst, b. Treating said internally protected catalyst with an aqueous acid or oxidant insoluble in hydrocarbons contained within pores in said crystals, c. Recovering the catalyst by removing the hydrocarbon. 제29항에 있어서, 외부 산성부위률 예비코우크스화하여 비활성화시키는 것을 특징으로 하는 방법.30. The method according to claim 29, characterized in that it is deactivated by external acid site precoking. 제29항에 있어서, 상기 촉매의 입자 직경이 4.0㎛이하인 것을 특징으로 하는 방법.30. The method of claim 29, wherein the catalyst has a particle diameter of 4.0 μm or less. 제40항에 있어서, 입자 직경이 0.1㎛ 내지 3.75㎛사이인 것을 특징으로 하는 방법.The method of claim 40, wherein the particle diameter is between 0.1 μm and 3.75 μm. 제29항에 있어서, 2,6-디메틸나프탈렌을 산화시켜 2,6-디카르복시나프탈렌을 제조하는 단계를 부가적으로 포함하는 것을 특징으로 하는 방법.The method of claim 29, further comprising oxidizing 2,6-dimethylnaphthalene to produce 2,6-dicarboxynaphthalene. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019920700896A 1989-10-17 1990-10-16 Selective diethylation of naphthalene with 2,6-diethylnaphthalene Withdrawn KR920703482A (en)

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US3832449A (en) * 1971-03-18 1974-08-27 Mobil Oil Corp Crystalline zeolite zsm{14 12
US4026959A (en) * 1976-05-07 1977-05-31 American Cyanamid Company Low temperature isomerization process for isopropylnaphthalene (100 percent sieve catalyst)
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