Comparing Amide-Forming Reactions Using Green Chemistry Metrics in an Undergraduate Organic Laboratory

被引：46

作者：

Fennie, Michael W. ^{[1
]}

Roth, Jessica M. ^{[1
]}

机构：

[1] Univ Scranton, Dept Chem, Scranton, PA 18510 USA

来源：

JOURNAL OF CHEMICAL EDUCATION | 2016年 / 93卷 / 10期

关键词：

Upper-Division Undergraduate; Organic Chemistry; Laboratory Instruction; Hands-On Learning/Manipulatives; Inquiry-Based/Discovery Learning Amides; Catalysis; Green Chemistry; NEXT-GENERATION GREEN; ATOM ECONOMY; PHARMACEUTICAL-INDUSTRY; CONFCHEM CONFERENCE; PERSPECTIVE; CURRICULUM; EFFICIENCY; REAGENT; COURSES;

D O I：

10.1021/acs.jchemed.6b00090

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this laboratory experiment, upper-division undergraduate chemistry and biochemistry majors investigate amide-bond-forming reactions from a green chemistry perspective. Using hydrocinnamic acid and benzylamine as reactants, students perform three types of amide-forming reactions: an acid chloride derivative route; a coupling reagent, promoted method; and a boric acid catalyzed condensation. After isolation of the common product, students assess the reactions using the 12 Principles of Green Chemistry and several green chemistry metrics: atom economy; reaction mass efficiency; process mass intensity; and the EcoScale. In addition to assessing what route is the greenest, students also compare the metrics to discern what aspects of green chemistry each metric captures. In order to extend sustainability to economic considerations, the projected "front-end" cost of synthesizing a kilogram of the amide is calculated based on data from each reaction. The experimental work is-conducted over two 3 h laboratory periods.

引用

页码：1788 / 1793

页数：6

共 43 条

[1] Direct and waste-free amidations and cycloadditions by organocatalytic activation of carboxylic acids at room temperature [J].