마이크로파 공정을 이용한 금속 프탈로시아닌의 무용매 합성

고진필; 신준식; 송승욱; 정현석; 정기석; 권종호; 박성수; Jin Phil Ko; Jun Sik Shin; Seung Wook Song; Hyun Suk Jung; Ki Suck Jung; Jong Ho Kwon; Seong Soo Park

Journal of the Korean Industrial and Engineering Chemistry, Vol.14, No.4, 500-504, June, 2003

Export Citation

마이크로파 공정을 이용한 금속 프탈로시아닌의 무용매 합성

Solvent-free Synthesis of Metal Phthalocyanine Under Microwave Processing

고진필, 신준식, 송승욱, 정현석, 정기석¹, 권종호¹, 박성수 ^†

부경대학교 화학공학부, 부산 608-739
¹(주) 프탈로스, 부산 608-739

Jin Phil Ko, Jun Sik Shin, Seung Wook Song, Hyun Suk Jung, Ki Suck Jung¹, Jong Ho Kwon¹, and Seong Soo Park^†

Division of Chemical Engineering, Pukyong National University, Busan 608-739, Korea
¹Pukyong Technocomplex, Phthalos Co. Ltd., Busan 608-739, Korea

E-mail:

초록

본 연구에서는 청정화학 기술의 일종으로서 ammonium molybdate 촉매의 존재하에서 phthalic anhydride, urea 및 copper (I) chloride를 무용매 상태에서 마이크로파를 조사하는 방식으로 한번에 반응시켜서 금속 프탈로시아닌을 합성하는 효과적인 합성법을 개발하였다. 무용매 기술이 접목된 마이크로파 공정은 재래식 공정에 비하여 짧은 시간, 높은 수율, 청정 반응 및 용이한 작업을 제공함을 알 수 있었다. 여러 온도에서 합성된 최종생성물들의 특성을 X선 회절장치 (XRD), 주사형 전자현미경 (SEM) 및 입도 분석법 (PSA)을 이용하여 비교 분석하였다.

An efficient green method has been developed for the synthesis of metal phthalocyanine through a one-pot reaction where phthalic anhydride and urea react with copper(I) chloride in the presence of ammonium molybdate catalyst under solvent-free condition using microwave irradiation. It was demonstrated that microwave processing combined with solvent-free techniques leads to shorter reaction times, higher yields, cleaner reaction products and easier work-up than classical processing. The products synthesized at various temperatures have been characterized by X-ray diffractometry (XRD), scanning electron microscopy (SEM), and particle size analysis (PSA).

Keywords:phthalocyanine;microwave;solvent-free;phthalic anhydride;urea

[References]

Metaxas AC, Meredith RJ, Industrial Microwave Heating, Peter Peregrinus Ltd., United Kingdom (1993)
Sutton WH, Am. Ceram. Soc. Bull., 67, 1656 (1988)
Caddick S, Tetrahedron, 51, 10403 (1995)
Kingston HM, Haswell SJ, Microwave Enhanced Chemistry, Am. Chem. Soc. Washington D.C. (1997)
Raner KD, Strauss CR, Trainor RW, J. Org. Chem., 60, 2456 (1995)
Strauss CR, Trainor RW, Aust. J. Chem., 48, 1665 (1995)
Perreux L, Loupy A, Tetrahedron, 57, 9199 (2001)
McKeown NB, Phthalocyanine Materials, Cambridge Univ. Press, United Kingdom (1998)
Wu Y, Tian H, Chen K, Liu Y, Zhu D, Dyes Pigments, 37, 317 (1998)
Herbst W, Hunger K, Industrial ORganic Pigments, VCH Publishers, New York (1987)
Law KY, Chem. Rev., 93, 449 (1993)
Kharisov BI, Blanco LM, Torres-Martinez LM, Garcia-Luna A, Ind. Eng. Chem. Res., 38(8), 2880 (1999)
Europian Patent, EP 0443107 A2 (1991)
Jung KS, Ko JP, Park SB, Park CY, Min SK, Kwon JH, Oh IH, Park SS, Polym.(Korea), 25(5), 609 (2001)
Jung KS, Ro JY, Lee JY, Park SS, J. Mater. Sci. Lett., 20(24), 2203 (2001)

[Related Articles]

[1] Metaxas AC, Meredith RJ, Industrial Microwave Heating, Peter Peregrinus Ltd., United Kingdom (1993)

[2] Sutton WH, Am. Ceram. Soc. Bull., 67, 1656 (1988)

[3] Caddick S, Tetrahedron, 51, 10403 (1995)

[4] Kingston HM, Haswell SJ, Microwave Enhanced Chemistry, Am. Chem. Soc. Washington D.C. (1997)

[5] Raner KD, Strauss CR, Trainor RW, J. Org. Chem., 60, 2456 (1995)

[6] Strauss CR, Trainor RW, Aust. J. Chem., 48, 1665 (1995)

[7] Perreux L, Loupy A, Tetrahedron, 57, 9199 (2001)

[8] McKeown NB, Phthalocyanine Materials, Cambridge Univ. Press, United Kingdom (1998)

[9] Wu Y, Tian H, Chen K, Liu Y, Zhu D, Dyes Pigments, 37, 317 (1998)

[10] Herbst W, Hunger K, Industrial ORganic Pigments, VCH Publishers, New York (1987)

[11] Law KY, Chem. Rev., 93, 449 (1993)

[12] Kharisov BI, Blanco LM, Torres-Martinez LM, Garcia-Luna A, Ind. Eng. Chem. Res., 38(8), 2880 (1999)

[13] Europian Patent, EP 0443107 A2 (1991)

[14] Jung KS, Ko JP, Park SB, Park CY, Min SK, Kwon JH, Oh IH, Park SS, Polym.(Korea), 25(5), 609 (2001)

[15] Jung KS, Ro JY, Lee JY, Park SS, J. Mater. Sci. Lett., 20(24), 2203 (2001)