含全氟丁基磺酰亚胺基团的聚苯乙烯树脂催化苯酚及对苯二酚的叔丁基化反应
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摘要
本文首次利用了一种新型的Br?nsted酸催化剂-含有全氟丁基磺酰亚胺基团的聚苯乙烯(PPFSI)作为高效的多相催化剂,催化合成多种酚类烷基化产物,例如:2-叔丁基对苯二酚、2,4-叔丁基苯酚和4-叔丁基苯酚等,研究了反应温度、反应时间、溶剂等因素对反应的影响,实验工作内容主要如下:
1.研究了PPFSI催化合成2-叔丁基对苯二酚反应的条件,最佳反应条件为:当对苯二酚加入量为0.330 g (3.0 mmol)时,烷基化试剂为0.332 mL (3.6 mmol)的叔丁醇,反应温度为130℃,反应时间5 h,溶剂1,2-二氯乙烷用量为3.0 mL,催化剂PPFSI用量5 mol%,本文在最佳反应条件基础上进行了反应,反应目标产物TBHQ收率为65.8%,而对苯二酚的转化率和TBHQ的选择性分别为76.7%和85.9%,均优于文献报道。
2.研究了PPFSI催化合成2,4-叔丁基苯酚反应的条件,最佳反应条件为:当苯酚加入量为0.282 g时,反应温度为100℃,反应时间4 h,正庚烷用量为3.0 mL,催化剂PPFSI用量1 mol%,苯酚和叔丁醇摩尔比为1:2左右。本文在最佳反应条件基础上进行了反应,反应结果收率为67.8%,2,4-叔丁基苯酚选择性为69.0%,苯酚转化率为98.3%。
3.研究了全氟磺酰亚胺基团的聚苯乙烯催化下叔丁醇和苯酚反应生成4-叔丁基苯酚的条件,最佳反应条件为:当苯酚加入量为0.282 g时,反应温度为1200C,反应时间3 h,1,2-二氯乙烷用量为3.0 mL,PPFSI催化剂用量3 mol%,叔丁醇与苯酚摩尔比为1.5:1。本文在最佳反应条件基础上进行了反应,苯酚转化率为94.0%,4-叔丁基苯酚的选择性为58.9%,反应结果收率为55.4%。
In this paper, we used polystyrene with pendent perfluoroalkylsulfonylimide groups polymer (PPFSI) as a strong Br?nsted acid catalyst in several tert-butylation reactions.The expected productions are 2-tert-butylhydroquinone (TBHQ), 2,4-ditert-butylphenol and 4-butylphenol, which are valuable organic materials and intermediates in chemical industry to produce drugs and additives.The tert-butylation reactions were studied under the various conditions.Our work was described as follows:
1.The reaction conditions were investigated in detail for the tert-butylation of hydroquinone with tert-butanol (TBA) in the presence of PPFSI, an optimized result was obtained when 0.330 g (3.0 mmol) hydroquinone reacts with 1:1.2 equiv. tert-butanol at 130℃for 5 h in 3 mL 1,2-dichloroethane in the presence of 5 mol% PPFSI. The high yield of 65.8% and selectivity of 85.9% of TBHQ were obtained respectively. The conversion of phenol was as high as 76.7%, which was much better compared with the reported results.
2. The reaction conditions were investigated in detail for the tert-butylation of phenol with tert-butanol (TBA) in the presence of PPFSI, an optimized result was obtained when 0.282 g (3.0 mmol) phenol reacts with 1:2 equiv. tert-butanol at 100℃for 4 h in 3.0 mL n-heptane in the presence of 1 mol% PPFSI. The high yield of 67.8% and selectivity of 69.0% of 2,4-DTBP were obtained respectively. The conversion of phenol was as high as 98.3%.
3. The reaction conditions were investigated in detail for the tert-butylation of phenol with tert-butanol (TBA) in the presence of PPFSI, a optimized result was obtained when 0.282 g (3.0 mmol) phenol reacts with 1:1.5 equiv. tert-butanol at 120℃for 3 h in 3.0 mL 1,2-dichloroethane in the presence of 3 mol% PPFSI. The high yield of 55.4% and selectivity of 58.9% of 4-TBP were obtained respectively. The conversion of phenol was as high as 94.0%.
1.研究了PPFSI催化合成2-叔丁基对苯二酚反应的条件,最佳反应条件为:当对苯二酚加入量为0.330 g (3.0 mmol)时,烷基化试剂为0.332 mL (3.6 mmol)的叔丁醇,反应温度为130℃,反应时间5 h,溶剂1,2-二氯乙烷用量为3.0 mL,催化剂PPFSI用量5 mol%,本文在最佳反应条件基础上进行了反应,反应目标产物TBHQ收率为65.8%,而对苯二酚的转化率和TBHQ的选择性分别为76.7%和85.9%,均优于文献报道。
2.研究了PPFSI催化合成2,4-叔丁基苯酚反应的条件,最佳反应条件为:当苯酚加入量为0.282 g时,反应温度为100℃,反应时间4 h,正庚烷用量为3.0 mL,催化剂PPFSI用量1 mol%,苯酚和叔丁醇摩尔比为1:2左右。本文在最佳反应条件基础上进行了反应,反应结果收率为67.8%,2,4-叔丁基苯酚选择性为69.0%,苯酚转化率为98.3%。
3.研究了全氟磺酰亚胺基团的聚苯乙烯催化下叔丁醇和苯酚反应生成4-叔丁基苯酚的条件,最佳反应条件为:当苯酚加入量为0.282 g时,反应温度为1200C,反应时间3 h,1,2-二氯乙烷用量为3.0 mL,PPFSI催化剂用量3 mol%,叔丁醇与苯酚摩尔比为1.5:1。本文在最佳反应条件基础上进行了反应,苯酚转化率为94.0%,4-叔丁基苯酚的选择性为58.9%,反应结果收率为55.4%。
In this paper, we used polystyrene with pendent perfluoroalkylsulfonylimide groups polymer (PPFSI) as a strong Br?nsted acid catalyst in several tert-butylation reactions.The expected productions are 2-tert-butylhydroquinone (TBHQ), 2,4-ditert-butylphenol and 4-butylphenol, which are valuable organic materials and intermediates in chemical industry to produce drugs and additives.The tert-butylation reactions were studied under the various conditions.Our work was described as follows:
1.The reaction conditions were investigated in detail for the tert-butylation of hydroquinone with tert-butanol (TBA) in the presence of PPFSI, an optimized result was obtained when 0.330 g (3.0 mmol) hydroquinone reacts with 1:1.2 equiv. tert-butanol at 130℃for 5 h in 3 mL 1,2-dichloroethane in the presence of 5 mol% PPFSI. The high yield of 65.8% and selectivity of 85.9% of TBHQ were obtained respectively. The conversion of phenol was as high as 76.7%, which was much better compared with the reported results.
2. The reaction conditions were investigated in detail for the tert-butylation of phenol with tert-butanol (TBA) in the presence of PPFSI, an optimized result was obtained when 0.282 g (3.0 mmol) phenol reacts with 1:2 equiv. tert-butanol at 100℃for 4 h in 3.0 mL n-heptane in the presence of 1 mol% PPFSI. The high yield of 67.8% and selectivity of 69.0% of 2,4-DTBP were obtained respectively. The conversion of phenol was as high as 98.3%.
3. The reaction conditions were investigated in detail for the tert-butylation of phenol with tert-butanol (TBA) in the presence of PPFSI, a optimized result was obtained when 0.282 g (3.0 mmol) phenol reacts with 1:1.5 equiv. tert-butanol at 120℃for 3 h in 3.0 mL 1,2-dichloroethane in the presence of 3 mol% PPFSI. The high yield of 55.4% and selectivity of 58.9% of 4-TBP were obtained respectively. The conversion of phenol was as high as 94.0%.
引文
[1]张鸣九,我国对叔丁基苯酚生产及应用开发,精细石油化工,1990,1 :20 .
[2] D. D. DesMarteau,Superacids--It's a Lot About Anions, Science, 2000, 289: 72～73
[3] Nie J,Zhao Z J, Xu J, et al. Lanthanide Bis[bis (1,1,1,3,3,3-hexafluoro-2-propoxy) sulfonyl]amide as a Novel Effective Acylation Catalyst, J. Chem. Res.(s)., 1999, 160～161
[4]张正波;周三一;聂进;高分子负载Yb(NTf2)3催化酯化及硝化反应应用化学, 2006,23,8
[5] Yubin Yuan, Jin Nie, Zhengbo Zhang, MCM-41 supported metal bis[(perfluoroalkyl)sulfonyl]imides as heterogeneous catalysts for aromatic nitration, Appl. Catal. A, 2005, 295(2):170～176.
[6] Xiao jiezhan, Zhang zhengbo, Nie jin, Preparation, characterization and catalytic activity of polystyrene with pendent perfluoroalkylsulfonylimide groups. J. Mol. Catal. A. 236 (2005) 119–124
[7]聂进,王新增,张正波,含全氟烷基磺酰亚胺侧链的高分子聚合物及其合成方法。专利申请号200410061384.4
[8] K.Ishihara,A.Hasegawa;Polystyrene-Bound Tetrafluorophenylbis (triflyl)methane as an Organic-Solvent-Swellable and Strong Bronsted Acid Catalyst, Angew. Chem. Int. Ed. 2001,40(21): 4077～4079
[9] M.D. Shahid, US Pat. 6,525,146.
[10] M. Blum and M. Roitberg, US Pat. 5,958,479.
[11] Kaitaranta, Jukka K.. Control of lipid oxidation in fish oil with various antioxidative compounds. J. Am. Oil. Chem. Soc,1992, 69(8), 810-13.,
[12] A. Knop , L.A. Pilato, Phenolic Resins Chemistry, Springer, Berlin, 1985.
[13] G.D.Yadav,N.S.Doshi ,Alkylation of hydroquinone with methyl tert-butyl ether andtert-butanol ,Catal Today 2000,60 ,263-273.
[14]许东颖,廖正福,曾汉维,油脂抗氧剂的介绍,广西师院学报〔自然科学版〕,1998, 15(3):58-61.
[15]郭建明,郭祀远,蔡妙迎等,抗氧剂TBHQ的研究,郑州粮食学院学报, 1998, 19 (4):51- 53.
[16] Diaz-Guerra, Luis M.; Ocana, Blanca; Half-wave potentials of 1-aza and 1,8-diazaanthraquinones. Bulletin des Societes Chimiques Belges 1995, 104(12), 683-90.
[17] H. Nakamura, Jap. Patent 6,281,341
[18] H. Nakamura, Jap. Patent 6,281,342
[19] F. Wataru and K. Shoji, Jap. Pat. 59-112935.
[20] S.M. Dougherty, S.D. DeBord and R.J. Maleski, US Pat.6,255,538.
[21] Y. Kamitori, M. Hojo, R. Masuda, et al, Silica gel as an effective catalyst for the alkylation of phenols and some heterocyclic aromatic compounds, J. Org. Chem., 1984, 49(22): 4161～4165.
[22] G. D. Yadav, H. Manyar, Novelties of synthesis of acetoveratrone using heteropoly acid supported on hexagonal mesoporous silica, Micropor. Mesopor. Mat., 2003, 27(1-3): 85～96.
[23] G. D.Yadav, N. S. Doshi, Alkylation of hydroquinone with methyl-tert-butyl-ether and tert-butanol, Catal Today, 2000, 60(3-4): 263～273.
[24] G. D.Yadav, N. S. Doshi, Alkylation of phenol with methyl-tert-butyl ether and tert-butanol over solid acids: efficacies of clay-based catalysts, Appl. Catal. A: Gen., 2002, 236(1-2): 129～147.
[25] G. D.Yadav, M. S. M. M. Rahuman, Efficacy of solid acids in the synthesis of butylated hydroxy anisoles by alkylation of 4-methoxyphenol with MTBE, Appl. Catal. A: Gen., 2003, 253(1): 113～123.
[26] Binjun Xu, Weiming Hua, Yinghing Yue,Alkylation of hydroquinone with tert-butanol over AlSBA-15 mesoporous molecular sieves Catal. Lett.2005,100,95.
[27] Bogdan C. Gagea, Andrei N. Parvulescu, Georges ,Alkylation of Hydroquinone with tert-butanol over Silica-immobilized Triflate Derivatives Catal Lett. 2005,105, 3–4,
[28] Anil Wali, Jagannath Das,Tert-butylation of hydroquinone with tert-butylphenols catalyzed by H-MCM-41 ,J. Mol. Catal. A: 2004, 214 ,253–256
[29] B.E.Firth. US Patent; 4 323 713,1982
[30]张威,异丁烯的利用,精细石油化工,1992 , 2 :57。
[31]韩引,对叔丁基苯酚合成技术的研究,高桥石化,2004,19(2),18。
[32] Jianzhou Gui , Hongyan Ban, Xiaohui Cong, Selective alkylation of phenol with tert-butyl alcohol catalyzed by Br¨onsted acidic imidazolium salts,J. Mol. Catal. A:, 2005,225 , 27–31.
[33] H.-Y. Shen, Z, M. A. Judeh, C. B. Ching, Selective alkylation of phenol with tert-butyl alcohol catalyzed by [bmim]PF6, Tetrahedron Lett., 2003, 44(5): 981983.
[34] Hao-Yu Shen, Zaher M.A. Judeh, Chi Bun Ching, Comparative studies on alkylation of phenol with tert-butyl alcohol in the presence of liquid or solid acid catalysts in ionic liquids, J. Mol. Catal. A: 2004,212, 301–308.
[35] Biju M. Devassy, G.V. Shanbhag, S.P. Mirajkar, Silicotungstate-modified zirconia as an efficientcatalyst for phenol tert-butylation,J. Mol. Catal. A:,2005,233,141-146.
[36] Ajit B. Shinde, Nilesh B. Shrigadi, Shriniwas D. amant,tert-Butylation of phenols using tert-butyl alcohol in the presence of FeCl3-modified montmorillonite K10,Appl. Catal. A:,2004,276 , 5–8.
[37] P.N.Urmi,Mkylation of Phenol with Isobutene Catalysed by Cation Exchange Resin:a Kinetic Study, J.Chem.Tech Biotechno1,1983,33A(1),1—11
[38] Merger Frani Dipl Chem Dr,German,DE2526644,1976—12—30.
[39] Gaharwar Raghubir Singh,,India, IN143026,1977—09—24
[40] S.E. Dapurkar and P. Selvam, Mesoporous H-GaMCM-48: A remarkable solid acid catalystfor tertiary butylation of phenol,J Catal ,2004, 224,178–186
[41] Kui Zhang,Changhua Huang,Huabin Zhang, Alkylantion of phenol with tert-butyl alcohol catalysed by zeolite Hβ,Appl. Catal. A:1998,166,89-95.
[42] Subramaniam,AnupamMitra,C.V.V.Satyanarayana, Para-selective butylation of phenol over silicoaluminophosphate molecular sieve SAPO-11 catalyst,Appl. Catal. A,1997,159 ,229-240.
[43]吴淑杰,黄家辉,吴通好, A1-SBA-15介孔分子筛的合成、表征及其在苯酚叔丁基化反应中的催化性能,催化学报,2006, 27(1),9。
[44]程能林,胡声闻,溶剂手册,(第一版)北京:化学工业出版社,1986.
[45]谢国梅,周小虹,班景昭,分析化学实验,1998, 11: 119
[46] I. Rabia; J. Zerouk; M. Kerkouche; M. Belkhodja, Chemical and textual characteristics of porous styrene-divinylbenzene copolymers as a function of chlorosulfonation reaction parameters, Reac& Func Poly. 1996,28:279～285
[47]余以刚,黄伟,林华山等,特丁基对苯二酚(TBHQ)应用与检测,粮食与油脂,2003, (3): 42～43.
[48]郭建明,郭祀远,蔡妙颜等,叔丁基对苯二酚的气相色谱分析,郑州粮食学院学报,1998, 19(4): 51～53.
[49]岳振锋,蓝芳,谢丽琪,气相色谱-质谱法测定XO酱油中BHA、BHT和TBHQ,中国粮油学报,2004, 19(5): 83～85.
[50]薛为齐,路风辉,邓国才,HPLC法分析叔丁基对苯二酚的纯度,天津化工,2003, 17(5): 52～55.
[51] J. Foropoulos; D.D. DesMarteau, Synthesis,Properties, and Reactions of Bis ((trifluoromethyl) sulfonyl)Imide, (CF3SO2)2NH , Inorg. Chem. 1984, 23: 3720～3723
[52] L.Q. Hu, D.D. DesMarteau, Synthesis of Perhaloalkanesulfonyl Halides and Their Sulfonimide Derivatives, Inorg. Chem. 1993, 32: 5007～5010
[2] D. D. DesMarteau,Superacids--It's a Lot About Anions, Science, 2000, 289: 72～73
[3] Nie J,Zhao Z J, Xu J, et al. Lanthanide Bis[bis (1,1,1,3,3,3-hexafluoro-2-propoxy) sulfonyl]amide as a Novel Effective Acylation Catalyst, J. Chem. Res.(s)., 1999, 160～161
[4]张正波;周三一;聂进;高分子负载Yb(NTf2)3催化酯化及硝化反应应用化学, 2006,23,8
[5] Yubin Yuan, Jin Nie, Zhengbo Zhang, MCM-41 supported metal bis[(perfluoroalkyl)sulfonyl]imides as heterogeneous catalysts for aromatic nitration, Appl. Catal. A, 2005, 295(2):170～176.
[6] Xiao jiezhan, Zhang zhengbo, Nie jin, Preparation, characterization and catalytic activity of polystyrene with pendent perfluoroalkylsulfonylimide groups. J. Mol. Catal. A. 236 (2005) 119–124
[7]聂进,王新增,张正波,含全氟烷基磺酰亚胺侧链的高分子聚合物及其合成方法。专利申请号200410061384.4
[8] K.Ishihara,A.Hasegawa;Polystyrene-Bound Tetrafluorophenylbis (triflyl)methane as an Organic-Solvent-Swellable and Strong Bronsted Acid Catalyst, Angew. Chem. Int. Ed. 2001,40(21): 4077～4079
[9] M.D. Shahid, US Pat. 6,525,146.
[10] M. Blum and M. Roitberg, US Pat. 5,958,479.
[11] Kaitaranta, Jukka K.. Control of lipid oxidation in fish oil with various antioxidative compounds. J. Am. Oil. Chem. Soc,1992, 69(8), 810-13.,
[12] A. Knop , L.A. Pilato, Phenolic Resins Chemistry, Springer, Berlin, 1985.
[13] G.D.Yadav,N.S.Doshi ,Alkylation of hydroquinone with methyl tert-butyl ether andtert-butanol ,Catal Today 2000,60 ,263-273.
[14]许东颖,廖正福,曾汉维,油脂抗氧剂的介绍,广西师院学报〔自然科学版〕,1998, 15(3):58-61.
[15]郭建明,郭祀远,蔡妙迎等,抗氧剂TBHQ的研究,郑州粮食学院学报, 1998, 19 (4):51- 53.
[16] Diaz-Guerra, Luis M.; Ocana, Blanca; Half-wave potentials of 1-aza and 1,8-diazaanthraquinones. Bulletin des Societes Chimiques Belges 1995, 104(12), 683-90.
[17] H. Nakamura, Jap. Patent 6,281,341
[18] H. Nakamura, Jap. Patent 6,281,342
[19] F. Wataru and K. Shoji, Jap. Pat. 59-112935.
[20] S.M. Dougherty, S.D. DeBord and R.J. Maleski, US Pat.6,255,538.
[21] Y. Kamitori, M. Hojo, R. Masuda, et al, Silica gel as an effective catalyst for the alkylation of phenols and some heterocyclic aromatic compounds, J. Org. Chem., 1984, 49(22): 4161～4165.
[22] G. D. Yadav, H. Manyar, Novelties of synthesis of acetoveratrone using heteropoly acid supported on hexagonal mesoporous silica, Micropor. Mesopor. Mat., 2003, 27(1-3): 85～96.
[23] G. D.Yadav, N. S. Doshi, Alkylation of hydroquinone with methyl-tert-butyl-ether and tert-butanol, Catal Today, 2000, 60(3-4): 263～273.
[24] G. D.Yadav, N. S. Doshi, Alkylation of phenol with methyl-tert-butyl ether and tert-butanol over solid acids: efficacies of clay-based catalysts, Appl. Catal. A: Gen., 2002, 236(1-2): 129～147.
[25] G. D.Yadav, M. S. M. M. Rahuman, Efficacy of solid acids in the synthesis of butylated hydroxy anisoles by alkylation of 4-methoxyphenol with MTBE, Appl. Catal. A: Gen., 2003, 253(1): 113～123.
[26] Binjun Xu, Weiming Hua, Yinghing Yue,Alkylation of hydroquinone with tert-butanol over AlSBA-15 mesoporous molecular sieves Catal. Lett.2005,100,95.
[27] Bogdan C. Gagea, Andrei N. Parvulescu, Georges ,Alkylation of Hydroquinone with tert-butanol over Silica-immobilized Triflate Derivatives Catal Lett. 2005,105, 3–4,
[28] Anil Wali, Jagannath Das,Tert-butylation of hydroquinone with tert-butylphenols catalyzed by H-MCM-41 ,J. Mol. Catal. A: 2004, 214 ,253–256
[29] B.E.Firth. US Patent; 4 323 713,1982
[30]张威,异丁烯的利用,精细石油化工,1992 , 2 :57。
[31]韩引,对叔丁基苯酚合成技术的研究,高桥石化,2004,19(2),18。
[32] Jianzhou Gui , Hongyan Ban, Xiaohui Cong, Selective alkylation of phenol with tert-butyl alcohol catalyzed by Br¨onsted acidic imidazolium salts,J. Mol. Catal. A:, 2005,225 , 27–31.
[33] H.-Y. Shen, Z, M. A. Judeh, C. B. Ching, Selective alkylation of phenol with tert-butyl alcohol catalyzed by [bmim]PF6, Tetrahedron Lett., 2003, 44(5): 981983.
[34] Hao-Yu Shen, Zaher M.A. Judeh, Chi Bun Ching, Comparative studies on alkylation of phenol with tert-butyl alcohol in the presence of liquid or solid acid catalysts in ionic liquids, J. Mol. Catal. A: 2004,212, 301–308.
[35] Biju M. Devassy, G.V. Shanbhag, S.P. Mirajkar, Silicotungstate-modified zirconia as an efficientcatalyst for phenol tert-butylation,J. Mol. Catal. A:,2005,233,141-146.
[36] Ajit B. Shinde, Nilesh B. Shrigadi, Shriniwas D. amant,tert-Butylation of phenols using tert-butyl alcohol in the presence of FeCl3-modified montmorillonite K10,Appl. Catal. A:,2004,276 , 5–8.
[37] P.N.Urmi,Mkylation of Phenol with Isobutene Catalysed by Cation Exchange Resin:a Kinetic Study, J.Chem.Tech Biotechno1,1983,33A(1),1—11
[38] Merger Frani Dipl Chem Dr,German,DE2526644,1976—12—30.
[39] Gaharwar Raghubir Singh,,India, IN143026,1977—09—24
[40] S.E. Dapurkar and P. Selvam, Mesoporous H-GaMCM-48: A remarkable solid acid catalystfor tertiary butylation of phenol,J Catal ,2004, 224,178–186
[41] Kui Zhang,Changhua Huang,Huabin Zhang, Alkylantion of phenol with tert-butyl alcohol catalysed by zeolite Hβ,Appl. Catal. A:1998,166,89-95.
[42] Subramaniam,AnupamMitra,C.V.V.Satyanarayana, Para-selective butylation of phenol over silicoaluminophosphate molecular sieve SAPO-11 catalyst,Appl. Catal. A,1997,159 ,229-240.
[43]吴淑杰,黄家辉,吴通好, A1-SBA-15介孔分子筛的合成、表征及其在苯酚叔丁基化反应中的催化性能,催化学报,2006, 27(1),9。
[44]程能林,胡声闻,溶剂手册,(第一版)北京:化学工业出版社,1986.
[45]谢国梅,周小虹,班景昭,分析化学实验,1998, 11: 119
[46] I. Rabia; J. Zerouk; M. Kerkouche; M. Belkhodja, Chemical and textual characteristics of porous styrene-divinylbenzene copolymers as a function of chlorosulfonation reaction parameters, Reac& Func Poly. 1996,28:279～285
[47]余以刚,黄伟,林华山等,特丁基对苯二酚(TBHQ)应用与检测,粮食与油脂,2003, (3): 42～43.
[48]郭建明,郭祀远,蔡妙颜等,叔丁基对苯二酚的气相色谱分析,郑州粮食学院学报,1998, 19(4): 51～53.
[49]岳振锋,蓝芳,谢丽琪,气相色谱-质谱法测定XO酱油中BHA、BHT和TBHQ,中国粮油学报,2004, 19(5): 83～85.
[50]薛为齐,路风辉,邓国才,HPLC法分析叔丁基对苯二酚的纯度,天津化工,2003, 17(5): 52～55.
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