聚3-羟基丁酸酯单体的化学合成工艺及基础研究
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摘要
聚3-羟基丁酸酯(PHB)是一种生物可完全降解塑料,β-丁内酯是合成PHB的主要单体,目前尚未工业化生产,因此PHB单体的合成工艺具有重要的实用价值。
本文中,以巴豆酸和溴化氢为原料来制备β-丁内酯。反应主要分为两个部分,首先是中间产物3-溴丁酸的合成反应,其次为3-溴丁酸发生分子内反应生成β-丁内酯。
在3-溴丁酸的合成反应中,考察了溶剂种类、引发剂用量、反应时间以及溶剂用量对收率的影响,确定了该步反应的最佳工艺条件为:乙醚为溶剂,引发剂用量1.50g,溶剂用量200ml,反应时间4天。实验结果表明,在收率达到文献报道水平的基础上,缩短了一半的反应时间。
在β-丁内酯的合成反应中,通过正交实验,研究了反应温度、反应时间和溶剂用量对合成反应的影响;通过外延实验确定了β-丁内酯合成反应的最佳工艺条件,反应平均收率为75.4%,超过了国内外文献报道水平(64%)。
此外,为进行工业化生产,需要生产过程中相关的物性数据,因此,本文同时测定了反应过程中相关物系的密度黏度以及溶解度数据。
在常压下,采用U形振动管密度计和乌氏黏度计测定了巴豆酸-苯、巴豆酸-甲苯和巴豆酸-乙酸乙酯二组分物系在298.15K～343.15K和巴豆酸-丙酮二组分物系在298.15K～323.15K下的密度和黏度。同时对不同组成下的密度与温度、浓度的关系进行了多元回归,对不同温度下的对比黏度ηr与组成的关系按Jones-Doles方程进行了拟合。最大标准偏差分别为0.00017、0.00202和0.0252。
采用激光监测系统,在293.15K～322.15K温度范围内分别测定巴豆酸在苯、甲苯和乙酸乙酯三种溶剂中的溶解度。并采用经验方程、λh方程对溶解度数据进行了回归,给出了相关的模型参数。结果表明经验方程和λh方程均能很好的回归巴豆酸在纯溶剂中的溶解度,最大平均误差分别为1.07%和1.04%。
Poly(3-hydroxybutyrate)(PHB) is the plastic which can be degraded completely by microorganism.β-butyrolactone is the most important raw material of producing PHB. By far, it has not been produced in commercial scale. Therefore, studying the producing method ofβ-butyrolactone is very necessary and of great importance in environmental protection and economy.
In this paper, crotonic acid and HBr were selected as raw materials to synthesizeβ-butyrolactone. There were two steps, one is the preparation of 3-bromoubutyric acid, the next is the preparation ofβ-butyrolactone.
In the first step, effects of solvent kinds, initiator amount, reaction time and solvent amount on yield were investigated. The optimal reaction conditions were solvent being ethyl ether, initiator amount being 1.50g, solvent amount being 200ml, reaction time being 4d. The results showed that on the basis of achieving literature value, the reaction time was reduced one half.
In the second step, orthogonal test was designed to investigate the facts of reaction temperature, reaction time and solvent amount on yield. And the optimal reaction conditions were determined by extension experiment. The average yield was 75.4% which was higher than the literature value of 64%.
In addition, in order to provide fundamental data for Industrialization production, the densities, viscosities and solubilities of correlative reaction systerms were measured in this paper. Densities and viscosities of binary systems of crotonic acid with benzene、toluene and ethyl acetate at the temperatures (298.15～343.15K) and of crotonic acid with acetone at the temperatures ( 298.15～323.15K) were measured under atmospheric pressure by using a vibrating U-shaped sample tube densimeter and Ubbelohde suspended-level viscometer. Density and reduced viscosity were fitted by a multiple regression analysis and Jones-Doles equation respectively, and the maximal average relative deviations were 0.00017, 0.00202 and 0.0252.
By using laser monitoring technique, solid-liquid equilibrium data of crotonic acid in benzene、toluene and ethyl acetate were measured within the temperature range from 293.15K to 322.15K. Empirical formula andλh equation were used to correlate the solubilities of crotonic acid in three solvents and the corresponding parameters were given. The results showed that empirical formula andλh model could correlate the solubility data of crotonic acid in three solvents and the maximal average relative deviations were 1.07% and 1.04%.
本文中,以巴豆酸和溴化氢为原料来制备β-丁内酯。反应主要分为两个部分,首先是中间产物3-溴丁酸的合成反应,其次为3-溴丁酸发生分子内反应生成β-丁内酯。
在3-溴丁酸的合成反应中,考察了溶剂种类、引发剂用量、反应时间以及溶剂用量对收率的影响,确定了该步反应的最佳工艺条件为:乙醚为溶剂,引发剂用量1.50g,溶剂用量200ml,反应时间4天。实验结果表明,在收率达到文献报道水平的基础上,缩短了一半的反应时间。
在β-丁内酯的合成反应中,通过正交实验,研究了反应温度、反应时间和溶剂用量对合成反应的影响;通过外延实验确定了β-丁内酯合成反应的最佳工艺条件,反应平均收率为75.4%,超过了国内外文献报道水平(64%)。
此外,为进行工业化生产,需要生产过程中相关的物性数据,因此,本文同时测定了反应过程中相关物系的密度黏度以及溶解度数据。
在常压下,采用U形振动管密度计和乌氏黏度计测定了巴豆酸-苯、巴豆酸-甲苯和巴豆酸-乙酸乙酯二组分物系在298.15K～343.15K和巴豆酸-丙酮二组分物系在298.15K～323.15K下的密度和黏度。同时对不同组成下的密度与温度、浓度的关系进行了多元回归,对不同温度下的对比黏度ηr与组成的关系按Jones-Doles方程进行了拟合。最大标准偏差分别为0.00017、0.00202和0.0252。
采用激光监测系统,在293.15K～322.15K温度范围内分别测定巴豆酸在苯、甲苯和乙酸乙酯三种溶剂中的溶解度。并采用经验方程、λh方程对溶解度数据进行了回归,给出了相关的模型参数。结果表明经验方程和λh方程均能很好的回归巴豆酸在纯溶剂中的溶解度,最大平均误差分别为1.07%和1.04%。
Poly(3-hydroxybutyrate)(PHB) is the plastic which can be degraded completely by microorganism.β-butyrolactone is the most important raw material of producing PHB. By far, it has not been produced in commercial scale. Therefore, studying the producing method ofβ-butyrolactone is very necessary and of great importance in environmental protection and economy.
In this paper, crotonic acid and HBr were selected as raw materials to synthesizeβ-butyrolactone. There were two steps, one is the preparation of 3-bromoubutyric acid, the next is the preparation ofβ-butyrolactone.
In the first step, effects of solvent kinds, initiator amount, reaction time and solvent amount on yield were investigated. The optimal reaction conditions were solvent being ethyl ether, initiator amount being 1.50g, solvent amount being 200ml, reaction time being 4d. The results showed that on the basis of achieving literature value, the reaction time was reduced one half.
In the second step, orthogonal test was designed to investigate the facts of reaction temperature, reaction time and solvent amount on yield. And the optimal reaction conditions were determined by extension experiment. The average yield was 75.4% which was higher than the literature value of 64%.
In addition, in order to provide fundamental data for Industrialization production, the densities, viscosities and solubilities of correlative reaction systerms were measured in this paper. Densities and viscosities of binary systems of crotonic acid with benzene、toluene and ethyl acetate at the temperatures (298.15～343.15K) and of crotonic acid with acetone at the temperatures ( 298.15～323.15K) were measured under atmospheric pressure by using a vibrating U-shaped sample tube densimeter and Ubbelohde suspended-level viscometer. Density and reduced viscosity were fitted by a multiple regression analysis and Jones-Doles equation respectively, and the maximal average relative deviations were 0.00017, 0.00202 and 0.0252.
By using laser monitoring technique, solid-liquid equilibrium data of crotonic acid in benzene、toluene and ethyl acetate were measured within the temperature range from 293.15K to 322.15K. Empirical formula andλh equation were used to correlate the solubilities of crotonic acid in three solvents and the corresponding parameters were given. The results showed that empirical formula andλh model could correlate the solubility data of crotonic acid in three solvents and the maximal average relative deviations were 1.07% and 1.04%.
引文
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[3]王禧,国内外降解塑料的现状及发展方向,江苏化工,2002,30(2):7～11
[4]李星,刘东辉,黄云华,我国可降解塑料的现状和发展趋势化工生产与技术,2004,11(4):26～31
[5]唐赛珍,我国可降解塑料的研究与进展,现代化工,2002,(1):2～7
[6]黄发荣,环境可降解塑料的研究与开发,材料导报,2000,7(14):40～44
[7] Lemoigne M, The identification of poly(3-hydroxybutyric acid), Ann. Inst Pasteur. Paris,1925,36:144～145
[8]戈进杰,生物降解高分子材料及其应用,北京:化学工业出版社, 2003, 227～228
[9]成国祥,开发聚羟基丁酸酯新技术,天津科技,2004,31(2):20～20
[10]朱奇,陈彦,郭善利等,生物降解塑料PHB的研究概况,生物学通报,2004,39(6):9～10
[11]任杰,可降解与吸收材料,北京:化学工业出版社,2003,114～273
[12]于冬梅,微生物法生产聚β-羟基丁酸酯概述,大化科技,2002(3):1～2
[13]王加宁,聚3-羟基丁酸酯化学合成工艺的研究:博士学位论文,天津大学,2002
[14] Hubbs J C, Marti N, Composition and process for the production of poly(3-hydroxyalkanoates),U.S.,5563239,October 8,1996
[15] Ohta T,Miyake T,Takaya H,An efficient synthesis of optically active 4-methyloxetan-2-one:asymmetric hydrogenation of diketene catalyzed by binapruthenium(Ⅱ) complexes [binap=2,2’-bis(diphenylphoshpino)-1,1’–binaphthyl], J Chem Soc, Chem Commum,1992,(23):1725～1726
[16]罗玲,张大洋,赵鸣玉,聚3-羟基丁酸酯的单体3-丁内酯的制备,沈阳化工学院学报,2000,14(3):164～167
[17]刘俊,化学合成法制被3-羟基丁酸酯及其共聚物的研究[D],天津大学:2006,1
[18] Lee L S, Chung M L, Excess volumes of cyclohexane with 2-propanone, 2-butanont systems, J. Chem. Eng. Data, 1997, 42(5):850～853
[19] JoséT, Concepcion D, Densities and tefractive indices for 1-hexene +o-xylene + m-xylene + p-xylene and + ethylbenzene, J. Chem. Eng. Data, 1995, 40:96～98
[20] Hatschek E, The Viscosity of liquids, New York: D. Van Nostrand Co, 1963, 406～520
[21] Alejandro E B, Juan F J, Gustava A, Experimental liquid viscosities of decane and octane + decane from 298.15K to 373.15K and up to 25MPa, J. Chem. Eng. Data, 1998, 43(3):441～446
[22] Dymond J H, Robertson J, Isdale J D, Transport Properties of nonelectrolyte liquid mixtures, Int. J. Thermophys, 1981, 2(3):223～236
[23] Harrison D E, Gosser R B, Rolling ball viscometer for use at temperatures to 400℃under pressures to 5 kilobar, Rev. Sci. Instrum.,1965, 36(12):1840～1843
[24] Isade J D, Spence C M, A self-centring falling body viscometer for high pressures, NEL. Report, 1975, No 592
[25] Welber B, Qumby S L, Measurement of the product of viscosity and density of liquid helium with a torsional crystal, Phys. Rev., 1957, 107(3):645～646
[26] De Bock A, Grevendonk W, Awouters H, Pressure dependence of the viscosity of liquid argon liquid oxygen measured by means of a torsionally vibrating quartz Crystal, Physica, 1967, 34(1):49～52
[27] Alfred H K, Jan V S, Viscosity of liquid toluene at temperatures from 25 to 150℃and at pressure up to 30 MPa, J. Chem. Eng. Data, 1992, 37(3):349～355
[28] Itterbeek A V, Zink H, Hellemans M J, Viscosity of liquid gases at pressures above one atmosphere, Physica, 1966, 32(2):489～493
[29] Knapstad B, Skj?isvik P A, ?ye H A, Viscosity of pure hydrocarbons, J. Chem. Eng. Data, 1989, 34:37～43
[30] Kao J T F, Kobayashi R, Theory and design of an absolute viscometer for low temperature-high pressure applications, Rev. Sci. Instrum., 1968, 39(3):824～834
[31] Assale M J, Papadaki M, Wakeham W A, Measurements of viscosity of benzene, toluene, and m-xylene at pressure up to 80 MPa, Int. J. Thermophys, 1991, 12(3):449～457
[32] Pádua A A H, Fareleira J M N A, Wakeham W A, A vibrating-wire densimeter for liquids at high pressures, Int. J. Thermophys, 1994, 15(2):229～243
[33] Crande T, Julsrad S, Oscillating-cup viscometer over an extended viscosity and temperature range, Int. J. Thermophys, 1993, 14(2):276～282
[34] Claire B, Jean L L, Test apparatus recent developments in shear rheometry of uncured rubber compounds, Polym. Test, 2000, 19(1):177～191
[35]陈惠钊,黏度测量,北京:中国计量出版社,1994
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