4-비닐시클로헥센을 이용한 에틸벤젠의 제조

주영제; 원정임; 김창민; 박광천; 이상옥; 김홍석

Journal of the Korean Industrial and Engineering Chemistry, Vol.7, No.2, 326-333, April, 1996

Export Citation

4-비닐시클로헥센을 이용한 에틸벤젠의 제조

Production of Ethylbenzene from 4-Vinylcyclohexene

주영제, 원정임, 김창민, 박광천, 이상옥, 김홍석

초록

1,3-부타디엔의 이량체인 4-비닐시클로헥센(4-vinylcyclohexene; 4-VCH)을 불균일계 촉매인 활성탄에 지지된 팔라듐과 수소주개 용매인 알콜 또는 물과 함께 니트로화합물류, 과산화수소, 염소산계[NaCln (n=1∼4)], 산도등과 같은 산화제를 사용하는 촉매 수소전달반응을 응용하여 탈수소화시켜 에틸벤젠을 제조하였다. 반응온도는 70∼110℃, 4-VCH와 니트로화합물(니트로기가 한개 또는 두개 있는 지방족 또는 방향족 화합물)의 몰비는 1:0.02에서 1:0.5로, 4-VCH와 과산화수소, 염소산계의 몰비는 1:0.1에서 1:3을 사용하였다.

Dehydrogenation of 4-vinylcyclohexene(4-VCH) to ethylbenzene is elucidated via catalytic transfer hydrogenation with the heterogeneous catalyst of Pd/C. Hydrogen-donor solvent is ethanol or water. Oxidizers of the catslytic dehydrogenation reaction are mono- or dinitro compounds, H₂O₂, NaClOn (n= 1∼4), or oxygen at 70∼110℃. The ratio of 4-VCH/Nitro compounds is 1:0.02 to 1:0.5 and 4-VCH vs. H₂O₂, or NaClOn (n=1∼4) is 1:0.1 to 1:3.

[References]

Gerhartz W, "Ullmann's Encyclopedia of Industrial Chemistry," A4, 431-446, VCH, Weinheim (1985)
Chauvel A, Lefebvre G, "Petrochemical Processes: Technical and Economic Characteristics," 1, 199-208, Technip. Paris (1989)
Kim HS, Kim DI, Kim CS, Joo YJ, J. Korean Ind. Eng. Chem., 5(5), 871 (1994)
주영제, 김창민, 김홍석, 한국 특허출원 94-21631 (1994)
McKetta JJ, "Encyclopedia of Chemical Processing and Design," 5, 101 ~ 109, Marcel Dekker, New York (1977)
"Kirk-Othmer Encyclopedia of Chemical Technology," 3rd ed., 4, 313 ~ 337, John Wiley & Sons, Inc., New York (1978)
Patterson JA, Crawford WC, Wilson JR, U.S. Patent, 4,163,761 (1979)
Patterson JA, Crawford WC, Wilson JR, U.S. Patent, 4,233,244 (1980)
Cihonski JL, U.S. Patent, 4,246,202 (1981)
Cihonski JL, U.S. Patent, 4,300,010 (1981)
Patterson JA, Crawford WC, Wilson JR, U.S. Patent, 4,322,556 (1982)
Patterson JA, Crawford WC, Wilson JR, U.S. Patent, 4,339,622 (1982)
Hart DW, Slaugh LH, U.S. Patent, 4,375,571 (1983)
Suzuka H, Hattori H, Appl. Catal., 47, L7 (1989)
Diesen RW, U.S. Patent, 5,276,257 (1994)
Diesen RW, U.S. Patent, 5,300,719 (1994)
Davis CS, U.S. Patent, 5,321,180 (1994)
Hucul DA, U.S. Patent, 5,336,822 (1994)
Davis CS, 일본 공개특허 평6-329563 (1994)
일본 공개특허 평7-41436 (1995)
Diesen RW, WO 94/01385
Hucul DA, WO 94/29248
Heaton DE, U.S. Patent, 5,096,870 (1992)
Diesen RW, Burdett KA, Dixit RS, King SST, Olken MM, U.S. Patent, 5,196,621 (1993)
Diesen RW, Burdett KA, Dixit RS, King SST, Olken MM, U.S. Patent, 5,329,057 (1994)

[1] Gerhartz W, "Ullmann's Encyclopedia of Industrial Chemistry," A4, 431-446, VCH, Weinheim (1985)

[2] Chauvel A, Lefebvre G, "Petrochemical Processes: Technical and Economic Characteristics," 1, 199-208, Technip. Paris (1989)

[3] Kim HS, Kim DI, Kim CS, Joo YJ, J. Korean Ind. Eng. Chem., 5(5), 871 (1994)

[4] 주영제, 김창민, 김홍석, 한국 특허출원 94-21631 (1994)

[5] McKetta JJ, "Encyclopedia of Chemical Processing and Design," 5, 101 ~ 109, Marcel Dekker, New York (1977)

[6] "Kirk-Othmer Encyclopedia of Chemical Technology," 3rd ed., 4, 313 ~ 337, John Wiley & Sons, Inc., New York (1978)

[7] Patterson JA, Crawford WC, Wilson JR, U.S. Patent, 4,163,761 (1979)

[8] Patterson JA, Crawford WC, Wilson JR, U.S. Patent, 4,233,244 (1980)

[9] Cihonski JL, U.S. Patent, 4,246,202 (1981)

[10] Cihonski JL, U.S. Patent, 4,300,010 (1981)

[11] Patterson JA, Crawford WC, Wilson JR, U.S. Patent, 4,322,556 (1982)

[12] Patterson JA, Crawford WC, Wilson JR, U.S. Patent, 4,339,622 (1982)

[13] Hart DW, Slaugh LH, U.S. Patent, 4,375,571 (1983)

[14] Suzuka H, Hattori H, Appl. Catal., 47, L7 (1989)

[15] Diesen RW, U.S. Patent, 5,276,257 (1994)

[16] Diesen RW, U.S. Patent, 5,300,719 (1994)

[17] Davis CS, U.S. Patent, 5,321,180 (1994)

[18] Hucul DA, U.S. Patent, 5,336,822 (1994)

[19] Davis CS, 일본 공개특허 평6-329563 (1994)

[20] 일본 공개특허 평7-41436 (1995)

[21] Diesen RW, WO 94/01385

[22] Hucul DA, WO 94/29248

[23] Heaton DE, U.S. Patent, 5,096,870 (1992)

[24] Diesen RW, Burdett KA, Dixit RS, King SST, Olken MM, U.S. Patent, 5,196,621 (1993)

[25] Diesen RW, Burdett KA, Dixit RS, King SST, Olken MM, U.S. Patent, 5,329,057 (1994)