多环芳基聚硅氧烷的合成及在弹性石英毛细管气相色谱中的应用
|
摘要
本文作者首先研究了多种芳基取代环戊二烯酮合成。芳基取代的环戊二烯酮很早就已经有人研究了,从基本的芳香醛合成偶姻,经催化氧化成偶酰,再与脂肪酮或芳香酮经过一步或两步反应得到相应的芳基取代的环戊二烯酮。但是大家的注意力多集中于全芳基取代环戊二烯酮,很少有人研究含部分脂肪基取代的芳基环戊二烯酮。作者借鉴了过去研究者的方法合成了一系列的芳基取代环戊二烯酮:四苯基环戊二烯酮(Ⅰ):3,4—二(4—甲氧基苯基)—2,5—二苯基环戊二烯酮(Ⅱ);3,4—二(呋喃—2—基)—2,5—二甲基环戊二烯酮(Ⅲ);苊式环戊二烯酮(Ⅳ);2,5—二甲基—3,4—二苯基环戊二烯酮(Ⅴ):3,4—二苯基环戊二烯酮(Ⅵ):2—甲基—3,4—二苯基环戊二烯酮(Ⅶ):2—乙基—3,4—二苯基环戊二烯酮(Ⅷ),并通过红外和核磁对它们进行了表征。其中化合物(Ⅵ)(Ⅶ)(Ⅷ)没有见到文献报道。
作者选择其中的四苯基环戊二烯酮(Ⅰ)与含双键的聚甲基硅氧烷通过Diels-Alder反应合成带有四苯基苯基的聚甲基硅氧烷高分子,在对其进行提纯后,用静态法涂敷在弹性石英毛细管上,对涂敷固定相的弹性石英毛细管柱各个方面进行评价,包括选择性、极性、柱效、内壁惰性、耐温性等。重点考察其对芳烃如苯基取代物、多环芳烃(PAH)的分离选择性。
考察结果表明涂敷四苯基苯基聚甲基硅氧烷固定相的弹性石英毛细管柱具有不低于4000P/m的柱效,有比较好的惰性,属于中等极性的固定相(总相常数为737),最高使用温度为330℃。对液体石蜡、煤焦油和含有多环芳烃样品的分离证明四苯基苯基聚甲基硅氧烷固定相对烷烃和芳烃类物质有较好的分离效果。对于多环芳基取代的聚甲基硅氧烷固定相的研究是有意义的。
At first the synthesis of a various of aryl-substituted cyclopentadienones are studied.Aryl-substituted cyclopentadienones were studied long ago.The benzoins, synthsised from the aromatic aldehydes,change to benzils through catalyzed oxidation.Then the benzils react with aryl- substituted ketones or alkyl- substituted ketones to form the aryl-substituted cyclopentadienones with one or two steps.But much attention were payed to the all aryl-substituted cyclopentadienones,few people studied the part aryl-substituted cyclopentadienones.The author synthesises a serious of aryl-substituted cyclopentadienones with the former researcher methods,such as 2,3,4,5-tetraphenylcyclopenta-2,4-dienone(Ⅰ),3,4-bis(4-methoxyphenyl)- 2,5-diphenylcyclopenta-2,4-dienone(Ⅱ),3,4-di(furan-2-yl)-2,5-dimethyicyclopenta-2, 4-dienone(Ⅲ),7,9-diphenyl-6bH-bicyclo[3.2.0]hepta-1(5),1,4-trieno[6,7-a]-acenaphthylen-8 (9bH)-one(Ⅳ),2,5-dimethyl-3,4-diphenylcyclopenta-2,4-dienone (Ⅴ),3,4-diphenylcyclopenta-2,4-dienone(Ⅵ),2-methyl-3,4-diphenylcyclo-penta-2, 4-dienone(Ⅶ),2-ethyl-3,4-diphenylcyclopenta-2,4-dienone(Ⅷ).They are all analysed with H-NMR and IR.The compounds(Ⅵ)、(Ⅶ)and(Ⅷ)are first peported in literature.
2,3,4,5-Tetraphenylcyclopenta-2,4-dienone(Ⅰ)is choosed to react with vinyl polysiloxane to form tetraphenyl phenyl polysiloxane through Diels-Alder reaction. After purification the product is coated on fused silica capillary columns with static method.Chromatographic properties like selectivity,polarity,separation efficiency, inertness,bleeding and so on of the capillary were evaluated,especially the selectivity of aromatic hydrocarbon such as substitutes of benzene,polycyclic aromatic hydrocarbon(PAH).
The investigation reveals that the fused silica capillary columns coated with tetraphenyl phenyl polysiloxane posseses superior separation efficiency(no less than 4000 P/m)and high intemess.It belongs to medium polar stationary phase(the constant of overall polarity is 737),the maximum allowable operating temperature is 330℃.The separation of the liquid paraffin,coal tar and polycyclic aromatic hydrocarbon confirms that tetraphenyl phenyl polysiloxane stationary phase has superior separation efficiency to alkanes and aromatic hydrocarbon compounds.It is significative to study the polysiloxane with polycyclic aromatic group.
作者选择其中的四苯基环戊二烯酮(Ⅰ)与含双键的聚甲基硅氧烷通过Diels-Alder反应合成带有四苯基苯基的聚甲基硅氧烷高分子,在对其进行提纯后,用静态法涂敷在弹性石英毛细管上,对涂敷固定相的弹性石英毛细管柱各个方面进行评价,包括选择性、极性、柱效、内壁惰性、耐温性等。重点考察其对芳烃如苯基取代物、多环芳烃(PAH)的分离选择性。
考察结果表明涂敷四苯基苯基聚甲基硅氧烷固定相的弹性石英毛细管柱具有不低于4000P/m的柱效,有比较好的惰性,属于中等极性的固定相(总相常数为737),最高使用温度为330℃。对液体石蜡、煤焦油和含有多环芳烃样品的分离证明四苯基苯基聚甲基硅氧烷固定相对烷烃和芳烃类物质有较好的分离效果。对于多环芳基取代的聚甲基硅氧烷固定相的研究是有意义的。
At first the synthesis of a various of aryl-substituted cyclopentadienones are studied.Aryl-substituted cyclopentadienones were studied long ago.The benzoins, synthsised from the aromatic aldehydes,change to benzils through catalyzed oxidation.Then the benzils react with aryl- substituted ketones or alkyl- substituted ketones to form the aryl-substituted cyclopentadienones with one or two steps.But much attention were payed to the all aryl-substituted cyclopentadienones,few people studied the part aryl-substituted cyclopentadienones.The author synthesises a serious of aryl-substituted cyclopentadienones with the former researcher methods,such as 2,3,4,5-tetraphenylcyclopenta-2,4-dienone(Ⅰ),3,4-bis(4-methoxyphenyl)- 2,5-diphenylcyclopenta-2,4-dienone(Ⅱ),3,4-di(furan-2-yl)-2,5-dimethyicyclopenta-2, 4-dienone(Ⅲ),7,9-diphenyl-6bH-bicyclo[3.2.0]hepta-1(5),1,4-trieno[6,7-a]-acenaphthylen-8 (9bH)-one(Ⅳ),2,5-dimethyl-3,4-diphenylcyclopenta-2,4-dienone (Ⅴ),3,4-diphenylcyclopenta-2,4-dienone(Ⅵ),2-methyl-3,4-diphenylcyclo-penta-2, 4-dienone(Ⅶ),2-ethyl-3,4-diphenylcyclopenta-2,4-dienone(Ⅷ).They are all analysed with H-NMR and IR.The compounds(Ⅵ)、(Ⅶ)and(Ⅷ)are first peported in literature.
2,3,4,5-Tetraphenylcyclopenta-2,4-dienone(Ⅰ)is choosed to react with vinyl polysiloxane to form tetraphenyl phenyl polysiloxane through Diels-Alder reaction. After purification the product is coated on fused silica capillary columns with static method.Chromatographic properties like selectivity,polarity,separation efficiency, inertness,bleeding and so on of the capillary were evaluated,especially the selectivity of aromatic hydrocarbon such as substitutes of benzene,polycyclic aromatic hydrocarbon(PAH).
The investigation reveals that the fused silica capillary columns coated with tetraphenyl phenyl polysiloxane posseses superior separation efficiency(no less than 4000 P/m)and high intemess.It belongs to medium polar stationary phase(the constant of overall polarity is 737),the maximum allowable operating temperature is 330℃.The separation of the liquid paraffin,coal tar and polycyclic aromatic hydrocarbon confirms that tetraphenyl phenyl polysiloxane stationary phase has superior separation efficiency to alkanes and aromatic hydrocarbon compounds.It is significative to study the polysiloxane with polycyclic aromatic group.
引文
1 J.C.Giddings,"Unified Separation Science".John Wiley & Sons,Inc.,New York,NY,P.1,1991
2 G.B.Levy,Amer.Lab.,18(12),62(1986)
3 James A T,Martin A J P.Biochem J,1952,50:679;Analyst,1952,77:915
4 Deemter J J Van,Zuiderweg F J,Klinkenberg A.Chem Eng Sci,1956,5:271
5 Giddings J C,Robinson R A.Anal Chem,1962,34:885
6 Giddings J C.Anal Chem,1963,35:2215
7 Giddings J C.In:Gas Chromatography,1964.Goldup A ed.London:Butterworths,1964.3
8 Golay M J E.In:Gas Chromatography,1958.Desty D H.ed.London:Butterworths,1958.36;Ana Chem,1957,29:298
9 M.J.E.Golay,"Progress Report of Gas Chromatographic Experimental work for September and October 1956" Perkin-Elmer Corp,Norwalk,Conn,Nov.15,1956Reprinted on L.S.Ettre,"Open-Tubular Columns in Gas Chromatography";Ple Press,New York,p.3(1965)
10 M.J.E.Golay,"Gas Chromatography(1957 Lansing Symp.)" V.J.Coates,H.J.Noebds,I.S.Fagerson,eds,Academic Press,New York p.1-13(1958).
11 Lee M L,Wright B M.J Chromatogr,1980,184:234
12 Lee M L,Yang F J,Bartle K D.Open Tubular Column Gas Chromatography.New York:John Wiley & Sons,Inc,1984.2
13 Dandeneau R,Bente P.Rooney T,et al.Am Lab,1979,11(9):61
14 McNair H M,Ogden M W,Hensley J L.Am Lab,1985,17(8):15
15 Kaiser MA,Klee M S.J Chromatogr Sci,1986,24:369
16 Koenig W A,J HRC & CC,1982,5:588
17 Witkiewicz Z.J Chromatogr,1982,251:311;1989,466:37
18 傅若农.色谱,1988,6:273
19 傅若农.色谱,1992,(1),10:14
20 Grob K.Making and Manipulating Capillary Columns for Gas Chromatography.Berlin:Dr Alfred Huethig Verlag,1986
21 Wang D.X.,Chong S L,Malik A.Sol-Gel Column Technology for Single-Step Deactivation,Coating,and Stationary-phase Immobilization in High-Resolution Capillary Gas Chromatography.Anal Chem[J],1997,69(22):4566-4576;
22 傅若农.色谱,1990,8:16
23 K.Grob and G.Grob,J.High Resoln.Chromatogr.Commun.2,109(1979).
24 M.L.Lee and B.W.Wright,J.Chromatogr.Sci.18,345(1980)
25 G.Schomburg,J High Resoln.Chromatogr.5,103(1967).
26 L.S.Ettrre and E.W.March,J.Chromatogr.91,5(1974)
27 Sehupp O E,et al.Gas Chromatographic Data Compilation Suppplement I,ASTM 25AS-1,1972.
28 顾惠祥、阎宝石主编,《气相色谱实用手册》,北京,化学工业出版社,p.1-28,1990
29 J.A.Yancey,J.Chromatogr.Sci.,32(8).349-357(1994)
30 J.A.Yancey,J.Chromatogr.Sci.,32(9).403-413(1994)
31 V.Schurig,J.Chromatogr.A,666(1+2),111-129(1994)
32 傅若农.色谱,1988,6:273
33 Lee M L,Yang F J,Bartle K D.Open Tubular Column Gas Chromatography.New York:John Wiley & Sons,1984.50
34 Kaiser M A,Klee M S.J Chromatogr Sci.,1986,24:369
35 周良模,王清海,王光华.化学试剂,1986,8:25
36 傅若农.色谱,1990,8:16
37 Dawes P,Cumbers M.Am Lab,1989(5):103
38 Hawkes S.Prefered stationary liquid for gas chromatography[J].J.Chromatogr.Sci.,1975,13:1152120.
39 Haken J K.J.Chromatogr.,1977,141:247
40 Haken J K.J.Chromatogr.,1984,30:1
41 Blomberg L.G,Markides K E.J HRC & CC,1982,5:520
42 Blomberg L.J HRC & CC,1982,5:520
43 Blomberg L.G,Markides K E.J HRC & CC,1982,5:520
44 Bemgard A,et al.J HRC & CC,1987,10:302
45 Noll W.Chemistry and Technology of Silicones.New York:Academic Press,1968.
46 Grob K.Chromatographia,1977,10:625
47 Strrala S S,Reich L.Polym Eng Sci,1980,20:654
48 Mayer,B.X.;Kaehlig,H.;Rauter,W.Analyst 2003,128(10),1238-1242.
49 Hinshaw J V.Response to the 2003 gas chromatography user study--Trends in column use andtechniques[J].LC-GC North America,2003,21(10):9602966.
50 Trestiamu S,et al.J HRC&CC,1981,8:771
51 Buijten J,et al.J Chromatogr,1982,237;465
52 P.A.Peaden,B.W.Wright,M.L.Lee,Chromatographia 1982,15,335-340
53 B.X.Mayer,Peter Zollner,E.Lorbeer,Walfried Rauter,J.sep.Sci.2002,25,60-66
54 L.G.Blomberg,LC-GC Int.,1998,11,760-762.
55 L.G.Blomberg,LC-GC Eur.,2001,14(2),106-112.
56 Ronald E.Majors LCGC North America New Chromatography Columns and Accessories at the 2002 Pittcon Conference:Part Ⅱ
57 Ronald E.Majors LCGC North America New Chromatography Columns and Accessories at the 2003 Pittcon Conference:Part Ⅱ
58 Ronald E.Majors LCGC North America New Chromatography Columns and Accessories at the 2004 Pittcon Conference:Part Ⅱ
59 Ronald E.Majors LCGC North America New-Chromatography Columns and Accessories at the 2005 Pittcon Conference:Part Ⅱ
60 Ronald E.Majors LCGC North America New Chromatography Columns and Accessories at the 2006 Pittcon Conference:Part Ⅱ
61 Roger Adams and C.S.Marvel.Organic Syntheses,Coll.Vol.1,p.94;Vol.1,p33
62 张国升,程俊,孙玉亮,钟永 安徽中医院学报 2003,22,6
63 Walter Ide,Buck Johannes.The Synthsis of Benzoin[J].Organic reaction,1948,(4):269
64 娄桂芹,吴振刚,陈圭文 华北煤炭医学院学报2004,6(5):570
65 王爱丽 化学通报,2002,(1):60
66 Bosler,Ber.,1881,14,323
67 Organic Syntheses,Coll.Vol.I,John Wiley and Sons,Inc.,New York,N.Y.,1941,p87
68 Marvin Weiss,Mildred Appel J.Am.Chem.Soc.,1948,70:3666
69 田勇,于伟民,李猛,郑锋 化学与粘合 2000,4,184
70 俞善信 化学试剂 1992;14(6):3691
71 陈毅平 中国药科工业杂志 1999,30(5):233
72 Walther Dilthey,and F.Quint,J.Prakt.Chem.1930,139,128
73 Walther Dilthey,W.Braun and O.Trosken,J.Prakt.Chem.1933,139,1-19
74 Walther Dilthey,O.Trosken,K.Plum and W.Schommer,J.Prakt.Chem.1934,141,331-49
75 S.B.Coan,D.E.Trucker,and E.I.Becker,J.Am.Chem.Soc.,77,60(1955)
76 Allen C F H,Vanallen J A.J.Am.Chem.Soc.,1950,72:5165
77 Bergmann P,Paul H.Chem.Ber.,1967,100:828
78 Stephen B.Coan,Donald E.Trucker,Ernest I.Becker.J.Am.Chem.Soc.,1954,77:60
79 Thomas A.Perfetti,Michael A.Ogliaruso Am.Chem.Soc.,1978,43(5):884
80 Elliot L.Shapiro,Ernest I.Becker J.Am.Chem.Soc.,1953,75:4769
81 Yamashita Y,Masumura M.Heterocycles,1980,14(1):29
82 吕洪舫,刘宗林,李尚听 化学试剂,1994,16(3),174-177
83 吕洪舫,有机硅化合物的双烯合成反应研究(硕士论文).1992,山东大学:济南
84 冯圣玉,陈剑华,杜作栋,四苯(基)苯基多乙烯基硅油的合成及结构测定.高分子学报,1987(6):p.471-4
85 姜志刚,耐辐照硅橡胶研究(博士论文).2007,山东大学:济南
86 B.X.Mayer.Peter Zollner,E.Lorbeer,Walfried Rauter,J.sep.Sci.2002,25,60-66
87 Morton and Stevens, J. Am. Chem. Soc, 52, 2031 (1930)
88 Henry Gilman and H. Smith Broandbent, J. Am. Chem. Soc. 70, 2619-21 (1948)
89 A. SCHONBERG and O. KRAEMER. Ber. 558B, 1174-94 (1922)
90 Ogden M W,McNair H M.J HRC & CC, 1985, 8: 326
91 Grob K. Making and Manipulating Capillary Columns for Gas Chromatography. Berlin: Huethig Verlag,1976.
92 M. Novotny, K.D. Bartle, Chromatographia 1974, 7,122-127.
93 T. Welsch, W. Engewald, C. Klaucke, Chromatographia 1977, 10, 22-24.
94 T. Welsch, R. Muller, W. Engewald, G Werner, J. Chromatogr. 1982, 241,41 -48.
95 T. Welsch, U. Teichmann, J. High Resol. Chromatogr. 1991, 14, 153-159.
96 J. Buijten, L. Blomberg, K. Markides, T. Wannman, J. Chromatogr. 1982,237,465 -468.
97 H. Moser, H. Reinhard, H. Arm, J. High Resol. Chromatogr. 1986, 9, 761.
98 B.X. Mayer, E. Lorbeer, J. Chromatogr. A 1977, 758,235-242.
99 B.X. Mayer, Peter Zollner, E. Lorbeer, Walfried Rauter, J. sep. Sci. 2002, 25,60- 66
100 P.A. Peaden, B.W. Wright, M.L. Lee, Chromatographia 1982,15, 335-340.
101 Bouche J, Verzele M. J Gas Chromatogr, 1968, 6: 501
102 Grob K. Making and Manipulating Capillary Columns for Gas Chromatography. Berlin: Huethig Verlag, 1976
103 Kong R C, Lee M L. J HRC&CC, 1983,6:319
104 Kong R C, Lee M L. Chromatographia, 1983,17:451
105 Dijkstra G, de Goey J. In: Gas Chromatography, Desty D H, ed. 1958, New York: Academic Press, 1958.56
106 Blomberg L. Chromatographia, 1975,8: 324
107 Levy R L, et al. Anal Chem, 1968,40:459
108 Van Dalen J P J. Chromatographia, 1972, 5: 354
109 McCannell M L, Novotny M. J Chromatogr, 1975, 112: 559
110 Schomburg G, et al. Novotny M. J Chromatogr, 1974, 99: 93
111 Rutten G A F M, Luyten J A. J. Chromatogr, 1972, 74: 177
112 固侃英,王昌时.色谱,1986,4,1-2
113 Grob K,et al.J Chromatogr,1981,213:211
114 C.Madani,E.M.Chambaz,et al.,J.Chromatogr.,126,161(1976)
115 L.Blomberg,J.Buijten,et al.,Chromatographia,11,521(1978)
116 Noll W.Chemistry and Technology of Sillcones.New York:Academic Press,1968
117 Grob K,Grob G.J Chromatogr,1981,213:211
118 Sandra P,et al.J HRC & CC,1981,4:411
119 Blomberg L,et al.J HRC & CC,1981,4:578
120 Peaden P A,et al.Chromatographia,1982,15:335
121 Wright B,et al.J Chromatogr,1982,248:17
122 Grob,K.,and Grob,G.,and Grob,K.,J.Chromatogr.156,1(1978)
123 G.Schomburg,H.Husmann and F.Weeke,Chromatographia,10,580(1970)
124 S.R.Lipsky,HRC&CC,6,359(1983)
125 P.Sandre and M.Verzele,Chromatographia,10,419(1977)
126 K.Grob Jr,G.Grob and K.Grob,HRC &CC,2,31(1979)
127 S.P.Cram,F.J.Tang and A.C.Brown,Chromatographia,10,397,(1977)
128 Th.Welsch,W.Engewald et al.,Chromatographia,10,22(1977)
129 Rohrschneider L.J Chromatogr,1966,22:6
130 McReynolds W O.J Chromatogr Sci,1970,8:685
131 沙逸仙,常理文.色谱手册.北京:科学出版社,1977
132 吉林化工研究院.实用气相色谱手册.北京:化学工业出版社,1979
133 苏皮纳 WR.气相色谱填充柱.詹益兴译.长沙:湖南科技出版社,1981
134 吴其灿,闫宝石,王文芳等,石油化工.12,835(1980)
135 Poole C F,Poole S K.Chem Rev,1989,69:377
136 Walter Jennings.玻璃毛细管柱气相色谱.徐秉玖,官宜文译.孙亦樑校.北京:北京大学出版社 1982,12
137 吴波、周重光、马晨等,山东省科学计划厅项目(鲁科1994110216):新型高质量弹性石英毛细管气相色谱柱,1994.1-1996.12,已鉴定.
138 B.X.Mayer,E.Lorbeer,J.High Resol.Chromatogr.1995,18,504-506.
139 B.Mayer,PhD dissertation,University of Vienna 1997.
140 李占雄,王标兵,欧育湘.耐高温聚合物.北京:化学工业出版社,2007.1
141 Colin F.Poole,Salwa K.Poole,J.Chromatogr.A 1184(2008)254-280.
142 E.Kaal,H.-G.Janssen,J.Chromatogr.A 1184(2008)43-60.
2 G.B.Levy,Amer.Lab.,18(12),62(1986)
3 James A T,Martin A J P.Biochem J,1952,50:679;Analyst,1952,77:915
4 Deemter J J Van,Zuiderweg F J,Klinkenberg A.Chem Eng Sci,1956,5:271
5 Giddings J C,Robinson R A.Anal Chem,1962,34:885
6 Giddings J C.Anal Chem,1963,35:2215
7 Giddings J C.In:Gas Chromatography,1964.Goldup A ed.London:Butterworths,1964.3
8 Golay M J E.In:Gas Chromatography,1958.Desty D H.ed.London:Butterworths,1958.36;Ana Chem,1957,29:298
9 M.J.E.Golay,"Progress Report of Gas Chromatographic Experimental work for September and October 1956" Perkin-Elmer Corp,Norwalk,Conn,Nov.15,1956Reprinted on L.S.Ettre,"Open-Tubular Columns in Gas Chromatography";Ple Press,New York,p.3(1965)
10 M.J.E.Golay,"Gas Chromatography(1957 Lansing Symp.)" V.J.Coates,H.J.Noebds,I.S.Fagerson,eds,Academic Press,New York p.1-13(1958).
11 Lee M L,Wright B M.J Chromatogr,1980,184:234
12 Lee M L,Yang F J,Bartle K D.Open Tubular Column Gas Chromatography.New York:John Wiley & Sons,Inc,1984.2
13 Dandeneau R,Bente P.Rooney T,et al.Am Lab,1979,11(9):61
14 McNair H M,Ogden M W,Hensley J L.Am Lab,1985,17(8):15
15 Kaiser MA,Klee M S.J Chromatogr Sci,1986,24:369
16 Koenig W A,J HRC & CC,1982,5:588
17 Witkiewicz Z.J Chromatogr,1982,251:311;1989,466:37
18 傅若农.色谱,1988,6:273
19 傅若农.色谱,1992,(1),10:14
20 Grob K.Making and Manipulating Capillary Columns for Gas Chromatography.Berlin:Dr Alfred Huethig Verlag,1986
21 Wang D.X.,Chong S L,Malik A.Sol-Gel Column Technology for Single-Step Deactivation,Coating,and Stationary-phase Immobilization in High-Resolution Capillary Gas Chromatography.Anal Chem[J],1997,69(22):4566-4576;
22 傅若农.色谱,1990,8:16
23 K.Grob and G.Grob,J.High Resoln.Chromatogr.Commun.2,109(1979).
24 M.L.Lee and B.W.Wright,J.Chromatogr.Sci.18,345(1980)
25 G.Schomburg,J High Resoln.Chromatogr.5,103(1967).
26 L.S.Ettrre and E.W.March,J.Chromatogr.91,5(1974)
27 Sehupp O E,et al.Gas Chromatographic Data Compilation Suppplement I,ASTM 25AS-1,1972.
28 顾惠祥、阎宝石主编,《气相色谱实用手册》,北京,化学工业出版社,p.1-28,1990
29 J.A.Yancey,J.Chromatogr.Sci.,32(8).349-357(1994)
30 J.A.Yancey,J.Chromatogr.Sci.,32(9).403-413(1994)
31 V.Schurig,J.Chromatogr.A,666(1+2),111-129(1994)
32 傅若农.色谱,1988,6:273
33 Lee M L,Yang F J,Bartle K D.Open Tubular Column Gas Chromatography.New York:John Wiley & Sons,1984.50
34 Kaiser M A,Klee M S.J Chromatogr Sci.,1986,24:369
35 周良模,王清海,王光华.化学试剂,1986,8:25
36 傅若农.色谱,1990,8:16
37 Dawes P,Cumbers M.Am Lab,1989(5):103
38 Hawkes S.Prefered stationary liquid for gas chromatography[J].J.Chromatogr.Sci.,1975,13:1152120.
39 Haken J K.J.Chromatogr.,1977,141:247
40 Haken J K.J.Chromatogr.,1984,30:1
41 Blomberg L.G,Markides K E.J HRC & CC,1982,5:520
42 Blomberg L.J HRC & CC,1982,5:520
43 Blomberg L.G,Markides K E.J HRC & CC,1982,5:520
44 Bemgard A,et al.J HRC & CC,1987,10:302
45 Noll W.Chemistry and Technology of Silicones.New York:Academic Press,1968.
46 Grob K.Chromatographia,1977,10:625
47 Strrala S S,Reich L.Polym Eng Sci,1980,20:654
48 Mayer,B.X.;Kaehlig,H.;Rauter,W.Analyst 2003,128(10),1238-1242.
49 Hinshaw J V.Response to the 2003 gas chromatography user study--Trends in column use andtechniques[J].LC-GC North America,2003,21(10):9602966.
50 Trestiamu S,et al.J HRC&CC,1981,8:771
51 Buijten J,et al.J Chromatogr,1982,237;465
52 P.A.Peaden,B.W.Wright,M.L.Lee,Chromatographia 1982,15,335-340
53 B.X.Mayer,Peter Zollner,E.Lorbeer,Walfried Rauter,J.sep.Sci.2002,25,60-66
54 L.G.Blomberg,LC-GC Int.,1998,11,760-762.
55 L.G.Blomberg,LC-GC Eur.,2001,14(2),106-112.
56 Ronald E.Majors LCGC North America New Chromatography Columns and Accessories at the 2002 Pittcon Conference:Part Ⅱ
57 Ronald E.Majors LCGC North America New Chromatography Columns and Accessories at the 2003 Pittcon Conference:Part Ⅱ
58 Ronald E.Majors LCGC North America New Chromatography Columns and Accessories at the 2004 Pittcon Conference:Part Ⅱ
59 Ronald E.Majors LCGC North America New-Chromatography Columns and Accessories at the 2005 Pittcon Conference:Part Ⅱ
60 Ronald E.Majors LCGC North America New Chromatography Columns and Accessories at the 2006 Pittcon Conference:Part Ⅱ
61 Roger Adams and C.S.Marvel.Organic Syntheses,Coll.Vol.1,p.94;Vol.1,p33
62 张国升,程俊,孙玉亮,钟永 安徽中医院学报 2003,22,6
63 Walter Ide,Buck Johannes.The Synthsis of Benzoin[J].Organic reaction,1948,(4):269
64 娄桂芹,吴振刚,陈圭文 华北煤炭医学院学报2004,6(5):570
65 王爱丽 化学通报,2002,(1):60
66 Bosler,Ber.,1881,14,323
67 Organic Syntheses,Coll.Vol.I,John Wiley and Sons,Inc.,New York,N.Y.,1941,p87
68 Marvin Weiss,Mildred Appel J.Am.Chem.Soc.,1948,70:3666
69 田勇,于伟民,李猛,郑锋 化学与粘合 2000,4,184
70 俞善信 化学试剂 1992;14(6):3691
71 陈毅平 中国药科工业杂志 1999,30(5):233
72 Walther Dilthey,and F.Quint,J.Prakt.Chem.1930,139,128
73 Walther Dilthey,W.Braun and O.Trosken,J.Prakt.Chem.1933,139,1-19
74 Walther Dilthey,O.Trosken,K.Plum and W.Schommer,J.Prakt.Chem.1934,141,331-49
75 S.B.Coan,D.E.Trucker,and E.I.Becker,J.Am.Chem.Soc.,77,60(1955)
76 Allen C F H,Vanallen J A.J.Am.Chem.Soc.,1950,72:5165
77 Bergmann P,Paul H.Chem.Ber.,1967,100:828
78 Stephen B.Coan,Donald E.Trucker,Ernest I.Becker.J.Am.Chem.Soc.,1954,77:60
79 Thomas A.Perfetti,Michael A.Ogliaruso Am.Chem.Soc.,1978,43(5):884
80 Elliot L.Shapiro,Ernest I.Becker J.Am.Chem.Soc.,1953,75:4769
81 Yamashita Y,Masumura M.Heterocycles,1980,14(1):29
82 吕洪舫,刘宗林,李尚听 化学试剂,1994,16(3),174-177
83 吕洪舫,有机硅化合物的双烯合成反应研究(硕士论文).1992,山东大学:济南
84 冯圣玉,陈剑华,杜作栋,四苯(基)苯基多乙烯基硅油的合成及结构测定.高分子学报,1987(6):p.471-4
85 姜志刚,耐辐照硅橡胶研究(博士论文).2007,山东大学:济南
86 B.X.Mayer.Peter Zollner,E.Lorbeer,Walfried Rauter,J.sep.Sci.2002,25,60-66
87 Morton and Stevens, J. Am. Chem. Soc, 52, 2031 (1930)
88 Henry Gilman and H. Smith Broandbent, J. Am. Chem. Soc. 70, 2619-21 (1948)
89 A. SCHONBERG and O. KRAEMER. Ber. 558B, 1174-94 (1922)
90 Ogden M W,McNair H M.J HRC & CC, 1985, 8: 326
91 Grob K. Making and Manipulating Capillary Columns for Gas Chromatography. Berlin: Huethig Verlag,1976.
92 M. Novotny, K.D. Bartle, Chromatographia 1974, 7,122-127.
93 T. Welsch, W. Engewald, C. Klaucke, Chromatographia 1977, 10, 22-24.
94 T. Welsch, R. Muller, W. Engewald, G Werner, J. Chromatogr. 1982, 241,41 -48.
95 T. Welsch, U. Teichmann, J. High Resol. Chromatogr. 1991, 14, 153-159.
96 J. Buijten, L. Blomberg, K. Markides, T. Wannman, J. Chromatogr. 1982,237,465 -468.
97 H. Moser, H. Reinhard, H. Arm, J. High Resol. Chromatogr. 1986, 9, 761.
98 B.X. Mayer, E. Lorbeer, J. Chromatogr. A 1977, 758,235-242.
99 B.X. Mayer, Peter Zollner, E. Lorbeer, Walfried Rauter, J. sep. Sci. 2002, 25,60- 66
100 P.A. Peaden, B.W. Wright, M.L. Lee, Chromatographia 1982,15, 335-340.
101 Bouche J, Verzele M. J Gas Chromatogr, 1968, 6: 501
102 Grob K. Making and Manipulating Capillary Columns for Gas Chromatography. Berlin: Huethig Verlag, 1976
103 Kong R C, Lee M L. J HRC&CC, 1983,6:319
104 Kong R C, Lee M L. Chromatographia, 1983,17:451
105 Dijkstra G, de Goey J. In: Gas Chromatography, Desty D H, ed. 1958, New York: Academic Press, 1958.56
106 Blomberg L. Chromatographia, 1975,8: 324
107 Levy R L, et al. Anal Chem, 1968,40:459
108 Van Dalen J P J. Chromatographia, 1972, 5: 354
109 McCannell M L, Novotny M. J Chromatogr, 1975, 112: 559
110 Schomburg G, et al. Novotny M. J Chromatogr, 1974, 99: 93
111 Rutten G A F M, Luyten J A. J. Chromatogr, 1972, 74: 177
112 固侃英,王昌时.色谱,1986,4,1-2
113 Grob K,et al.J Chromatogr,1981,213:211
114 C.Madani,E.M.Chambaz,et al.,J.Chromatogr.,126,161(1976)
115 L.Blomberg,J.Buijten,et al.,Chromatographia,11,521(1978)
116 Noll W.Chemistry and Technology of Sillcones.New York:Academic Press,1968
117 Grob K,Grob G.J Chromatogr,1981,213:211
118 Sandra P,et al.J HRC & CC,1981,4:411
119 Blomberg L,et al.J HRC & CC,1981,4:578
120 Peaden P A,et al.Chromatographia,1982,15:335
121 Wright B,et al.J Chromatogr,1982,248:17
122 Grob,K.,and Grob,G.,and Grob,K.,J.Chromatogr.156,1(1978)
123 G.Schomburg,H.Husmann and F.Weeke,Chromatographia,10,580(1970)
124 S.R.Lipsky,HRC&CC,6,359(1983)
125 P.Sandre and M.Verzele,Chromatographia,10,419(1977)
126 K.Grob Jr,G.Grob and K.Grob,HRC &CC,2,31(1979)
127 S.P.Cram,F.J.Tang and A.C.Brown,Chromatographia,10,397,(1977)
128 Th.Welsch,W.Engewald et al.,Chromatographia,10,22(1977)
129 Rohrschneider L.J Chromatogr,1966,22:6
130 McReynolds W O.J Chromatogr Sci,1970,8:685
131 沙逸仙,常理文.色谱手册.北京:科学出版社,1977
132 吉林化工研究院.实用气相色谱手册.北京:化学工业出版社,1979
133 苏皮纳 WR.气相色谱填充柱.詹益兴译.长沙:湖南科技出版社,1981
134 吴其灿,闫宝石,王文芳等,石油化工.12,835(1980)
135 Poole C F,Poole S K.Chem Rev,1989,69:377
136 Walter Jennings.玻璃毛细管柱气相色谱.徐秉玖,官宜文译.孙亦樑校.北京:北京大学出版社 1982,12
137 吴波、周重光、马晨等,山东省科学计划厅项目(鲁科1994110216):新型高质量弹性石英毛细管气相色谱柱,1994.1-1996.12,已鉴定.
138 B.X.Mayer,E.Lorbeer,J.High Resol.Chromatogr.1995,18,504-506.
139 B.Mayer,PhD dissertation,University of Vienna 1997.
140 李占雄,王标兵,欧育湘.耐高温聚合物.北京:化学工业出版社,2007.1
141 Colin F.Poole,Salwa K.Poole,J.Chromatogr.A 1184(2008)254-280.
142 E.Kaal,H.-G.Janssen,J.Chromatogr.A 1184(2008)43-60.
© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号 地址：北京市海淀区学院路29号 邮编：100083 电话：办公室：(+86 10)66554848；文献借阅、咨询服务、科技查新：66554700 |