Solubility of Pravastatin Sodium in Water, Methanol, Ethanol, 2-Propanol,
上传者:孙文颙|上传时间:2015-05-10|密次下载
Solubility of Pravastatin Sodium in Water, Methanol, Ethanol, 2-Propanol,
2466J.Chem.Eng.Data2008,53,2466–2468
SolubilityofPravastatinSodiuminWater,Methanol,Ethanol,2-Propanol,1-Propanol,and1-Butanolfrom(278to333)K
ChunyanJia,QiuxiangYin,*JingjingSong,GuangyangHou,andMeijingZhang
SchoolofChemicalEngineeringandTechnology,TianjinUniversity,Tianjin300072,People’sRepublicofChina
Thesolubilitiesofpravastatinsodiuminwater,methanol,ethanol,2-propanol,1-propanol,and1-butanolfrom(278to333)Kweremeasured.Alasermonitoringobservationtechniquewasusedtodeterminethedissolutionofthesolidphaseinthesolid+liquidmixture.Theexperimentaldatawerecorrelatedwithasemiempiricalequation.Thesolubilitiesinthesixsolventsdecreaseinthefollowingorder:water>methanol>ethanol>1-propanol>1-butanol>2-propanol.
Introduction
Pravastatin([1S-[1R(??*,γ*)2R,6R,8??(R*),8aR]]-1,2,6,7,8,8a-hexahydro,??,γ,6-trihydroxy-2-methyl-8-(2-methyl-1-oxobutoxy)-1-naphthalene-heptanoicacid),whosechemicalstructureisshowninFigure1,isamemberoftheclassofpharmaceuticalcompoundscalledstatins.Statinscurrentlyarethemosteffectivemedicationsforloweringserumcholesterollevelsinpatientswithatherosclerosisandhypercholesteremia.Pravastatinsodium,themonosodiumsaltofpravastatin,canexistinhydrated,anhydrous,solvated,andunsolvatedforms1(CASRN81131-70-6).
Previously,pravastatinsodiumwasavailableonlyintheamorphousform.Inrecentyears,thepreparationofpravastatinsodiuminthecrystalformhasbeenreported.1,2Incomparisonwiththeamorphousform,thecrystallinesubstanceshavemanyadvantages:theirphysicalaswellaschemicalpropertiesarebetterde?ned,andtheyaremorestable.
Ithasbeenfoundthatdifferentpolymorphicformsofpravastatinsodiumcanbeobtainedinthecrystallizationprocessbyusingdifferentsolvents.1Toselectthepropersolventandtodesignanoptimizedresearchprocess,itisnecessarytoknowthesolubilityofpravastatinsodiumindifferentsolvents.Inthiswork,itssolubilitiesofthetitlecompoundinwater,methanol,ethanol,2-propanol,1-propanol,and1-butanolattemperaturesbetween(298and333)Kweremeasuredusingtheisothermalmethod.3-6Alasermonitoringobservationtechniquewasusedtodeterminethedissolutionofthesolute.
Table1.SolubilityofPravastatinSodiuminDifferentPureSolventsfrom(278to333)KT/K278.4283288293298303277.8283287.9293297.8278283288293298303278283288293298278283288293298303278.1283288293298303
103x19.1111.9316.2421.6528.5234.3122.4624.4826.9530.0932.623.13.253.463.664.064.290.6050.6840.7530.8180.9032.082.162.192.272.382.741.081.181.271.441.591.78
100(x1-xcalcd/x1)
1.3-1.91-0.880.964.251.212.651.671.341.14-2.14.832.130-0.01-3.33-0.361.363.492.670.2-1-10.6-0.780.48-1.37-7.3-8.2-3.070.52-0.261.61-1.53-5.65
T/K
103x140.8947.7255.2864.1972.384.1437.3241.7549.2158.868.674.634.935.696.927.939.421.031.11.411.641.93.434.496.212.1615.78
100(x1-xcalcd/x1)
-0.436-1.94-2.060.161.166.98-1.37-3.64-0.942.530.061.776.844.50-1.91-1.33-3.340.8-4.33-3.36-1.872.09-4.88-1.173.926.61-4.16
water
308313318323328333methanol
302.9308313318324ethanol
3083133183233283332-propanol
303308318322.9327.91-propanol
3083133183283331-butanol
308313318.2323328
ExperimentalSection
Materials.CrystallinepowderpravastatinsodiumofformAwithamassfractionhigherthan99.5%obtainedfromShanghaiTianweiPharmaceuticalCo.Ltd.(Mw446.52,molecularformulaC23H35NaO7),China,wasusedasreceivedwithoutfurtherpuri?cation.Water,methanol,ethanol,2-propanol,1-propanol,and1-butanol(purchasedfromTianjinChemicalReagentCo.,China)usedforexperimentswereofanalyticalreagentgradeandweredehydratedwithmolecularsievesbeforeuse.Theirmassfractionwashigherthan99.5%.Distilleddeionizedwaterwasused.
ApparatusandProcedure.Thesolubilityofpravastatinsodiumwasmeasuredbytheisothermalmethod,andthe
*Correspondingauthor.Fax:+86-22-27374971.E-mail:qxyin@http://wendang.chazidian.com.
2.232.93.454.084.93-0.28-6.512.16-2.91-8.56
experimentalapparatususedwassimilartothatdescribedindetailintheliterature.6Theexperimentswereperformedinacylindricaldouble-jacketedglassvesselhavingaworkingvolumeof100mL,inwhichthetemperaturewascontrolledto
10.1021/je800196kCCC:$40.75?2008AmericanChemicalSociety
PublishedonWeb09/03/2008
JournalofChemical&EngineeringData,Vol.53,No.10,20082467
x1)
m1?M1
m1?M12?M2
(1)
wherem1andm2representthemassesofthesoluteandsolventandM1andM2arethemolecularweightsofthesoluteandthesolvent,respectively.
ResultsandDiscussion
Figure1.Chemicalstructureofpravastatin
内容需要下载文档才能查看sodium.
beconstantwithin0.05Kthroughathermostattedbath(Wanda/sidainstrumentHC2010,China).Amagneticstirbarwasusedforturbulentmixingofsuspension.Thedissolutionofthesolutewasexaminedbytheintensityofthelaserbeamthatpenetratedthroughthesuspension.Thelasermonitoringsystem(purchasedfromPhysicsDepartmentofPekingUniversity)consistedofalasergenerator(typeJD-3,China),aphotoelectricswitch(typemodel271,China),andalightintensitydisplay.
Themassesofthesamplesandsolventsweredeterminedusingananalyticalbalance(MetlerToledoAB204-N,Switzer-land)withanaccuracyof0.0001g.Thismethodisbasedonsequentiallyaddingknownmassesofsolutetoastirredsolutionkeptata?xedtemperature.Predeterminedmassesofsoluteandsolventweretransferredintothejacketedvessel.Thesolventtransferredintothevesselwasoverweight.Afterstirringata?xedtemperaturefor10min,anadditionalsoluteofknownmass{about(0.1to0.3)mg}wasintroducedintothevesselwithcontinuousstirring.Thisprocedurewasrepeateduntilthesolutewascompletelydissolvedwithintheintervalofadditionof20min.Then,thetotalamountofthesoluteadded(includingthelastaddition)wasusedtocomputethesolubility.Thedissolutionofthesolutewasmonitoredbyalaserbeam.Whenthesolutedissolvedcompletely,thesolutionwasclear,andthelaserintensitythatpenetratedthroughthesolutionattaineditsmaximum.Otherwise,thesolutewasbelievednottobedissolvedcompletely.Thesamesolubilityexperimentwasconductedthreetimes,andthemeanvalueswereusedtocalculatethemolefractionsolubilityx1basedonthefollowingequation
Thesolubilitydataofpravastatinsodiuminwater,methanol,ethanol,2-propanol,1-propanol,and1-butanolfrom(278to333)KarelistedinTable1andmorevisuallygiveninFigure2.Forthesakeofthepracticalapplication,itiscommontodescribethesolid-liquidequilibriumdatawithatheoreticalsemiem-piricalexpression.Ithasbeenfoundthatthemodi?edApelblatequation7can?tthesolubilitydataverywellforseveralsolid-liquidequilibriumsystems.8-11Here,thissemiempiricalequationwastentativelyusedtocorrelatetheexperimentalsolubilitydataofpravastatinsodiuminthesixsolventsunderconsideration.
Thesolubilityofasolidinaliquidmaybeexpressedinaverygeneralmannerby
?Hf,1Tf,1?Cpf,1Tf,1
lnx1)--1--1+
RTf,1TRT
?Cpf,1Tf,1
ln-lnγ1(2)RT
wherex1,γ1,?Hf,1,?Cpf,1,Tf,1,R,andTstandforthemole
fractionofsolute,activitycoef?cient,enthalpyoffusion,differenceinthesoluteheatcapacitybetweenthesolidandliquidatthemeltingtemperature,meltingtemperatureofthesolute,gasconstant,andequilibriumtemperatureinthesaturatedsolution,respectively.Forregularsolutions,theactivitycoef-?cientisgivenby
(
)
(
)
lnγ1)A+
B(T?K)
(3)
whereAandBstandforempiricalconstants.Introducingγ1frompreviousequationsintoeq2withsubsequentrearrange-mentsresultsinthe
内容需要下载文档才能查看equation
Figure2.Molefractionsolubilityofpravastatinsodiuminsixdifferentsolventsbetween(298and333)K.
2468JournalofChemical&EngineeringData,Vol.53,No.10,2008
lnx?Hf,1RT+?Cpf,1
1)
[
(1+lnTf,1R
f,1)-A-[B+(
?Hf,1RT+?Cpf,1)]
T]
1?Cpf,1
f,1-R
lnT(4)
f,1RTwhichcanbewrittenas
lnx1)a+
b
(T?K)
+cln(T?K)(5)
ThedeviationsbetweentheexperimentalandcalculatedresultsarealsopresentedinTable1.Thevaluesofparametersa,b,andcineq5andtheroot-mean-squaredeviations(rmsd)de?nedbyeq6arelistedinTable2.Itcanbeseenthatthecalculatedsolubilitiesshowgoodagreementwiththeexperi-mentalvalues.
{N
calcd21/2
rmsd)
1x1i
-x1iN(6)
i∑)1(x1i
)}
whereNisthenumberofexperimentalpointsandxcalcdandxrepresentthesolubilitycalculatedfromeq5and1thei
experi-1imentalvalue,respectively.
FromTable1,itcanbeseenthatwithinthetemperaturerangeofmeasurementsthesolubilitiesofpravastatinsodiuminwater,methanol,ethanol,2-propanol,1-propanol,and1-butanolin-creasewithincreasingtemperaturewithoutexception.Inaddi-tion,thesolubilitiesofpravastatinsodiuminwaterandmethanolaremuchhigherthanthoseintheotherfoursolvents.Referredtothefactthatthepolaritiesofthesixsolventsusedintheexperimentsdecreaseinthefollowingorder,water(100)>methanol(76.2)>ethanol(65.4)>1-propanol(61.7)>1-bu-tanol(60.2)>2-propanol(54.6),12inaccordwiththesolubilitiesorder,itcanbeconcludedthatthebiggerthepolarityofthesolventused,thehigherthesolubilityofthetitlecompound.
Table2.ParametersofEquation2forPravastatinSodiuminDifferentPureSolventssolventabc102rmsdwater437.79-23095.8-63.872.66methanol-264.949800.7740.131.99ethanol-39616190.79593.242-propanol-155.464909.7723.172.461-propanol-1197.3651088.13179.035.531-butanol
-637.02
25916.05
95.42
3.99
Thiscanbeduetotheion-dipoletypeinteractionbetweenthe
saltformsolventsandtheproticsolute.Thisinteractiongetsstrongerasthepolarityofthesolventgetslarger.AscanbeseenfromTable1,thereisasuddenincreaseofthesolubilityin1-propanolathighertemperature.Thereasonforthisismaybethattheaddedpravastatinsodiumreactedwiththesolvent.Thisistobedeterminedinthefollowingstudy.FromFigure1,itcanbeseenthatpravastatinsodiumisacompoundwithhighpolarity,whichisledbytwocarboxylsandthreehydroxylsinthemolecule.Thatistosaythesolubilitybehaviorofpravastatinsodiumjustaccordswiththeempiricalrule,“likedissolveslike”.
LiteratureCited
(1)Keri;Vilmos,S.;Csaba,A.;Nagyne,A.;Judith.Formsofpravastatin
http://wendang.chazidian.com7001919,Feb.21,2000.
(2)P?aum,http://wendang.chazidian.com6740775,
May25,2004.
(3)Nie,Q.;Wang,J.K.;Wang,Y.L.;Wang,S.Solubilityof11R-Hydroxy-16R,17R-EpoxyprogesteroneinDifferentSolventsbetween283Kand323K.J.Chem.Eng.Data2005,50,989–992.
(4)Zhang,H.T.;Wang,J.K.;Chen,Y.;Nie,Q.SolubiliyofSodium
CefotaximeinAqueous2-PropanolMixtures.J.Chem.Eng.Data2006,51,2239–2241.
(5)Liu,B.S.;Gong,J.B.;Wang,J.K.;Jia,C.Y.SolubilityofPotassium
ClavulanateinEthanol,1-Propanol,1-Butanol,2-Propanol,and2-Methyl-1-propanolbetween273Kand305K.J.Chem.Eng.Data2005,50,1684–1686.
(6)Ren,G.B.;Wang,J.K.;Yin,Q.X.;Zhang,M.J.Solubilitiesof
proxetinehydrochloridehemihydratebetween286Kand363K.J.Chem.Eng.Data2004,49,1671–1674.
(7)Apelblat,A.;Manzurola,E.Solubilitiesofo-acetylsalicylic,4-ami-nosalic,3,5-dinitrosalicylic,andp-toluicacid,andmagnesium-DL-aspartateinwaterfromT)(278to348)K.J.Chem.Thermodyn.1999,31,85–91.
(8)Hao,H.X.;Wang,J.K.;Wang,Y.L.SolubilityofDexamethasone
SodiumPhosphateinDifferentSolvents.J.Chem.Eng.Data2004,49,1697–1698.
(9)Wang,L.C.;Wang,F.A.SolubilityofNiacinin3-Picoline+Water
from(287.65to359.15)K.J.Chem.Eng.Data2004,49,155–156.(10)Ren,B.Z.;Yuan,X.L.;Li,C.;Zhao,H.K.SolubilityofTripoly-cyanamideandCyanuricAcidinEthanediol,N,N-Dimethylformamide,andN,N-Dimethylacetamidefrom(301.07to363.35)K.J.Chem.Eng.Data2004,49,890–891.
(11)Wang,L.H.;Cheng,Y.Y.SolubilityofPuerarininWater,Ethanol,
andAcetonefrom(288.2to328.2)K.J.Chem.Eng.Data2005,50,1375–1376.
(12)Smallwood,I.M.HandbookofOrganicSolVentProperties;Arnold:
London,1996.ReceivedforreviewMarch22,2008.AcceptedJuly9,2008.
JE800196K
下载文档
热门试卷
- 2016年四川省内江市中考化学试卷
- 广西钦州市高新区2017届高三11月月考政治试卷
- 浙江省湖州市2016-2017学年高一上学期期中考试政治试卷
- 浙江省湖州市2016-2017学年高二上学期期中考试政治试卷
- 辽宁省铁岭市协作体2017届高三上学期第三次联考政治试卷
- 广西钦州市钦州港区2016-2017学年高二11月月考政治试卷
- 广西钦州市钦州港区2017届高三11月月考政治试卷
- 广西钦州市钦州港区2016-2017学年高一11月月考政治试卷
- 广西钦州市高新区2016-2017学年高二11月月考政治试卷
- 广西钦州市高新区2016-2017学年高一11月月考政治试卷
- 山东省滨州市三校2017届第一学期阶段测试初三英语试题
- 四川省成都七中2017届高三一诊模拟考试文科综合试卷
- 2017届普通高等学校招生全国统一考试模拟试题(附答案)
- 重庆市永川中学高2017级上期12月月考语文试题
- 江西宜春三中2017届高三第一学期第二次月考文科综合试题
- 内蒙古赤峰二中2017届高三上学期第三次月考英语试题
- 2017年六年级(上)数学期末考试卷
- 2017人教版小学英语三年级上期末笔试题
- 江苏省常州西藏民族中学2016-2017学年九年级思想品德第一学期第二次阶段测试试卷
- 重庆市九龙坡区七校2016-2017学年上期八年级素质测查(二)语文学科试题卷
- 江苏省无锡市钱桥中学2016年12月八年级语文阶段性测试卷
- 江苏省无锡市钱桥中学2016-2017学年七年级英语12月阶段检测试卷
- 山东省邹城市第八中学2016-2017学年八年级12月物理第4章试题(无答案)
- 【人教版】河北省2015-2016学年度九年级上期末语文试题卷(附答案)
- 四川省简阳市阳安中学2016年12月高二月考英语试卷
- 四川省成都龙泉中学高三上学期2016年12月月考试题文科综合能力测试
- 安徽省滁州中学2016—2017学年度第一学期12月月考高三英语试卷
- 山东省武城县第二中学2016.12高一年级上学期第二次月考历史试题(必修一第四、五单元)
- 福建省四地六校联考2016-2017学年上学期第三次月考高三化学试卷
- 甘肃省武威第二十三中学2016—2017学年度八年级第一学期12月月考生物试卷
网友关注
- 世纪花园项目部QC小组成果
- 控制钢筋闪光对焊质量qc成果
- 土木设计计算书
- 水泥粉煤灰碎石桩复合地基工程检验批质量验收记录表GD24010312
- 工程竣工验收总结报告(2009)
- QC小组活动成果
- 建筑设计公司
- 建筑工程项目管理练习题
- 现代规模养猪设计图预算
- 标准QC工程表34669
- 模板拆除工程检验批
- 浅谈建筑施工企业QC小组活动的开展
- 建筑企业QC小组活动成果问题分析
- 场地设计-场地总平面设计概述-总图
- 工程施工组设计样版[教学]
- QC提高现浇混凝土板表面观感质量.doc
- 桥隧工(城轨)_5级_操作技能鉴定要素细目表
- 高层住宅结构设计经验体会
- 砂加气砌块墙体裂缝控制QC
- 质量保证措施检查记录
- 临汾西站施工组织设计 3
- QC课题-地下车库地面施工质量控制
- QC小组活动成果
- 混凝土空心砌块墙体开裂的质量控制措施
- 民用建筑设计-平面设计
- 建筑设计
- 丰富多彩的客厅隔断造型
- 陕西省建筑节能设计导则
- 某建筑施工企业各种质量管理制度(最新最全)2590590053
- 龙湖地产设计管理标准及核心价值创造
网友关注视频
- 北师大版数学 四年级下册 第三单元 第二节 小数点搬家
- 冀教版小学英语五年级下册lesson2教学视频(2)
- 沪教版八年级下次数学练习册21.4(2)无理方程P19
- 三年级英语单词记忆下册(沪教版)第一二单元复习
- 小学英语单词
- 沪教版牛津小学英语(深圳用) 四年级下册 Unit 2
- 外研版英语三起6年级下册(14版)Module3 Unit2
- 精品·同步课程 历史 八年级 上册 第15集 近代科学技术与思想文化
- 外研版八年级英语下学期 Module3
- 二年级下册数学第一课
- 冀教版小学数学二年级下册第二周第2课时《我们的测量》宝丰街小学庞志荣
- 二次函数求实际问题中的最值_第一课时(特等奖)(冀教版九年级下册)_T144339
- 苏教版二年级下册数学《认识东、南、西、北》
- 冀教版小学数学二年级下册第二单元《租船问题》
- 30.3 由不共线三点的坐标确定二次函数_第一课时(市一等奖)(冀教版九年级下册)_T144342
- 苏科版数学七年级下册7.2《探索平行线的性质》
- 沪教版八年级下册数学练习册20.4(2)一次函数的应用2P8
- 北师大版八年级物理下册 第六章 常见的光学仪器(二)探究凸透镜成像的规律
- 青岛版教材五年级下册第四单元(走进军营——方向与位置)用数对确定位置(一等奖)
- 【部编】人教版语文七年级下册《过松源晨炊漆公店(其五)》优质课教学视频+PPT课件+教案,辽宁省
- 化学九年级下册全册同步 人教版 第25集 生活中常见的盐(二)
- 第19课 我喜欢的鸟_第一课时(二等奖)(人美杨永善版二年级下册)_T644386
- 七年级下册外研版英语M8U2reading
- 外研版英语七年级下册module3 unit2第二课时
- 冀教版小学数学二年级下册第二单元《有余数除法的简单应用》
- 【部编】人教版语文七年级下册《老山界》优质课教学视频+PPT课件+教案,安徽省
- 3.2 数学二年级下册第二单元 表内除法(一)整理和复习 李菲菲
- 第8课 对称剪纸_第一课时(二等奖)(沪书画版二年级上册)_T3784187
- 外研版英语七年级下册module1unit3名词性物主代词讲解
- 冀教版小学数学二年级下册第二单元《有余数除法的竖式计算》
精品推荐
- 2016-2017学年高一语文人教版必修一+模块学业水平检测试题(含答案)
- 广西钦州市高新区2017届高三11月月考政治试卷
- 浙江省湖州市2016-2017学年高一上学期期中考试政治试卷
- 浙江省湖州市2016-2017学年高二上学期期中考试政治试卷
- 辽宁省铁岭市协作体2017届高三上学期第三次联考政治试卷
- 广西钦州市钦州港区2016-2017学年高二11月月考政治试卷
- 广西钦州市钦州港区2017届高三11月月考政治试卷
- 广西钦州市钦州港区2016-2017学年高一11月月考政治试卷
- 广西钦州市高新区2016-2017学年高二11月月考政治试卷
- 广西钦州市高新区2016-2017学年高一11月月考政治试卷
分类导航
- 互联网
- 电脑基础知识
- 计算机软件及应用
- 计算机硬件及网络
- 计算机应用/办公自动化
- .NET
- 数据结构与算法
- Java
- SEO
- C/C++资料
- linux/Unix相关
- 手机开发
- UML理论/建模
- 并行计算/云计算
- 嵌入式开发
- windows相关
- 软件工程
- 管理信息系统
- 开发文档
- 图形图像
- 网络与通信
- 网络信息安全
- 电子支付
- Labview
- matlab
- 网络资源
- Python
- Delphi/Perl
- 评测
- Flash/Flex
- CSS/Script
- 计算机原理
- PHP资料
- 数据挖掘与模式识别
- Web服务
- 数据库
- Visual Basic
- 电子商务
- 服务器
- 搜索引擎优化
- 存储
- 架构
- 行业软件
- 人工智能
- 计算机辅助设计
- 多媒体
- 软件测试
- 计算机硬件与维护
- 网站策划/UE
- 网页设计/UI
- 网吧管理