1、第十章 羧酸及其衍生物芳香烃 HCORO分类分类 一元酸一元酸 二元酸二元酸 脂肪酸脂肪酸 饱和酸饱和酸 不饱和酸不饱和酸 脂环酸脂环酸 芳香酸芳香酸 CH3COOH即乙酸 CH3CHCH2COOHCH33-甲基丁酸-(甲基丁酸)CHCCH2COOH3-羟基-3-羧基戊二酸HOOCCH2CCH2COOHOHCOOHCOOHCH3间甲基苯甲酸COONa+HClCOOH+NaClCl3CCOOHCl2CHCOOHClCH2COOHCH3COOH0.651.292.864.76CH3CH2CHCOOHClCH3CHCH2COOHClCH2CH2CH2COOHClCH3CH2CH2COOH2.864.
2、064.524.813.16FCH2COOHClCH2COOHBrCH2COOHICH2COOHCH3COOH2.592.862.904.76pKapKapKaRCOOH+RHCO2脱羧酶H2O丁二酸丁二酸酐+CH2HHOCH2COOOOCH2CCH2COOC己二酸环戊酮+CO2H2O+OHOHCOCH2CH2CH2CH2CH2CH2CH2CH2CCOOCH3CH2CHOHCOOH-羟基丁酸(醇酸)COOHOH邻羟基苯甲酸(酚酸)CH3CHOHCOOHHOOCCHCHOHCOOHOH2-羟基丙酸或-羟基丙酸(乳酸)2,3-二羟基丁二酸(酒石酸)CH3CHOHCH2COOH3-羟基丁酸(-羟基丁
3、酸)COOHOHCOOHOHCOOHOHOHOHCH2OHCOOHCH3COOHpKa3.834.76CH3CHOHCOOHCH2CH2OHCOOHCH3CH2COOHpKa3.874.514.86CH3CHCOOHOHHOCHCOHOCH3OOCH3OOCH3+2H2O-羟基丙酸丙交酯CH3CHCH2COOHOHCH3CHCHCOOH+H2O-羟基丁酸2-丁烯酸CH2CH2CH2COHOHOOO常温-羟基丁酸-丁内酯+H2OOCH2COHCH2OHCH2CH2OO-羟基戊酸-戊内酯+H2OOO+NaOHHOCH2CH2CH2COONa-丁内酯-羟基丁酸钠CH3CHOHCOOH托伦试剂或稀硝酸
4、CH3CCOOHOCH3CHOHCH2COOH稀硝酸CH3CCH2COOHOOHOHCOOHOHCOOHOHCO2+CO2+CH3CHCOOHOHCHCHCOOHOHHOOCOHCOOHOHCOOHOH+(CH3CO)2OCOOHOCOCH3+CH3COOH冰醋酸COOHCHOHCOOHCH2-2HCOOHCOCOOHCH2苹果酸草酰乙酸CH2CCH2COOHHOOCCOOHOHCOOHOHOHOHCH3CCH2OCOOH(丁酮酸)H3CCHOOCO丙酮酸3丁酮酸HOOCCCH2OCOOH丁酮二酸CH3COCOOHCHCOOHCH3OHCH3CH2COOHpKa2.493.864.88CH3C
5、COOHOHCH3CHCOOHOH丙酮酸乳酸RCCOOHO浓RCOHO+COH2SO4CH3CCH2COOHOCH3CCH3O+CO2微热RCCH2OCOOH+2NaOHRCOONa+CH3COONa+H2OCH3CCOOHO150CH3CHO+CO2丙酮酸乙醛稀H2SO4CH3CCOOHOCH3CHCOOHOH丙酮酸乳酸+2H-2HCH3CCH2COOHOCH3CHCH2COOHOH丁酮酸羟基丁酸+2H-2HCOCOOHCH2CH2COOHCH3CH2COOHCH3COOHCOOH乙酸丙酸苯甲酸COCH3CH3CH2COCO乙酰基丙酰基苯甲酰基CCCH2CH2CH2CH2CCOHOHOOOO
6、O+H2O丁二酸酐+HOHClRCORCOOCORRCOORRCONH2RCOOHRCOOHCOOHR+RCOOH+OH-H+或OH-H+或R OHRCOOH+NH3回流冷水酸酐需加热成均相才能迅速反应CORXCOROCORCOROR+HNH2CORNH2+HXCOOHROHRC HCOO C2H5COC H3HC H3CCOO C2H5C HOH酮式烯醇式CH3COCHHCOC2H5OCH3CCH3OCH3COCH2COOC2H5CH3COCH2COCH3COCH2COCH3C6H5CH2CCH3OHCH3CCHCOC2H5OHOCH3CCHCCH3OHOC6H5CCHCCH3OHO酮式烯醇
7、式烯醇式含量(%)0.000157.576.090.0H5C2OCCH2COOOC2H5CHHCOOC2H5COOC2H5NaOC2H5CHCOOC2H5COOC2H5RXNa+-CHRCOOC2H5COOC2H5C2H5ONaRXCRRCOOC2H5COOC2H5CRHCOOHCOOHH2O,H+_CO2H2O,H+CRRCOOHCOOH_CO2CH2COOHRCHRRCOOHH2C2O2CCH2CO2C2H5(1)C2H5ONa(2)CH3CH2CH2BrCH3CH2CH2CH(CO2C2H5)2(1)OH-/H2O(2)H+/CH3CH2CH2-CH2COOH2H5C2O2CCH2CO2
8、C2H52C2H5ONa2(H5C2O2CCHCO2C2H5)BrCH2CH2Br(H5C2O2C)CHCH2CH2CH(CO2C2H5)2(1)OH-/H2O(2)H+/HOOCCH2CH2CH2CH2COOHH5C2O2CCH2CO2C2H5(1)C2H5ONa(2)H5C2O2CCHBrCH3H5C2O2CCHCH(CO2C2H5)2CH3(1)OH-/H2O(2)H+/HOOCCHCH2COOHCH3CO+Cl2活性碳200CClClOCClClOCO2ROHClCOORROHROCOORNH3CNH2NH2O+H2O水解HCl醇解氨解脲(尿素)碳酸 酯+H2OCO2NH3O220MPa180NH2CONH4ONH2CNH2+CO(NH2)2HNO3CO(NH2)2 HNO3硝酸脲CO2NH3CONH2NH2NaOHNa2CO3NH4ClNH3CO2+H2O,HCl,H2OH2O尿素酶+CO22CONH2NH2H2O+HNO22N232CONH2NH2NH3+CONHNH2CONH2+CNHNH2NH2CNNH2HNH2氨基腈胍+CO2CNHNH2NH2H2O+CNHNH2NH22H2CO3The end.