[Description of the course] In this course, the instructor will give instructions on basic tasks of chemical experiments for sophomore students who studied Chemical Engineering and Industrial Chemistry Laboratories I a/b and I b/a, to cultivate their skills in experimental tasks and their understanding of organic chemistry, inorganic chemistry, and analytical chemistry. From the viewpoint of a practical chemical industry education, the following three themes are set; (1) “Organic synthesis I” for learning a basic organic reaction, nucleophilic substitution reaction, (2) “Organic synthesis II: aldehyde and ketone discrimination, nucleophilic addition” for learning a reaction using a Grignard reagent, which is a typical organic metal compound, and (3) “ε-Caprolactam” for learning the preparation of nylon, which is a typical synthetic fiber.
[Aim of the course] To understand the connection of basic chemistry to material society, it is essential to deeply examine the experimental results obtained by synthesis reaction through analyses and comprehension. One must learn the fundamental tasks with certainty and then approach the experiments with the underlying principles of reactions and safety. In this experiment, students first learn the essentials of fundamental tasks in a lecture and experimental presentation. Then, they practice the fundamental tasks while going through the three themes. Examinations of basic knowledge and practical thinking as well as writing experimental reports for each theme will enable the students to acquire correct synthetic and analytical techniques and to cultivate discussion skills.
At the end of this course, students will be able to:
1) apply fundamental tasks such as filtration, washing, drying, vacuum distillation, and so on to a number of unit processes.
2) complete a general style of the experimental report including results, discussions, and survey details.
3) explain the historical background and practical materials related to each theme.
4) acquire systematic knowledge from experiments and to develop a plan for a safe and productive chemical experiment.
(Organic synthesis I) nucleophilic substitution reactions, elimination reactions, Williamson ether synthesis
(Organic synthesis II) nucleophilic addition, reduction, functional group discrimination, organometallic chemistry, gas chromatography,
(ε-Caprolactam) oximation reactions, Beckmann rearrangement, recrystallization, ring-opening polymerization, 6-nylon
|✔ Specialist skills||Intercultural skills||Communication skills||Critical thinking skills||✔ Practical and/or problem-solving skills|
In this course, all the students will start with (1) experimental presentation. Then, the students are divided into three groups to learn the following three experiments in turn: (2) Organic synthesis I: butyl isopropyl ether, (3) Organic synthesis II: aldehyde and ketone discrimination, nucleophilic addition, and (4) ε-Caprolactam. In the last day, exercise problems and interpretation of the answers will be given to assess the students’ level of understanding.
|Course schedule||Required learning|
|Class 1||Guidance of experimental outline and fundamental operations||Understand an outline of an experiment and draw up a plan|
|Class 2||Experimental presentations of the fundamental operations||Understand an outline of an experiment and draw up a plan|
|Class 3||Synthesis of organic compounds I: halogenation reaction・steam distillation||Learn skills for halogenations of alcohols and steam distillation.|
|Class 4||Synthesis of organic compounds I: halogenation reaction・distillation||Learn skills for distillation of an organic halide and analysis by gas chromatography.|
|Class 5||Synthesis of organic compounds I: Williamson ether synthesis||Learn skills for Williamson ether synthesis.|
|Class 6||Synthesis of organic compounds I: Williamson ether synthesis・distillation||Characterize raw ether product and discuss the nucleophilic substitution.|
|Class 7||Organic Synthesis I I: characterization of carbonyl functional groups||Characterize carbonyl functional groups.|
|Class 8||Organic Synthesis II: nucleophilic addition, reduction||Synthesize alcohols by using hydride reagents.|
|Class 9||Organic Synthesis II: distillation under reduced pressure, analysis||Purify the products by distillation and analyze the pure compounds.|
|Class 10||Organic Synthesis II: nucleophilic addition - introduction to organometallic chemistry||Synthesize alcohols by the Grignard reagents.|
|Class 11||ε-Caprolactam: nucleophilic addition||Synthesize oximes from carbonyl compounds.|
|Class 12||ε-Caprolactam: Beckmann rearrangement||Synthesize amides by Beckmann rearrangement.|
|Class 13||ε-Caprolactam: recrystallization||Purify ε-ｃaprolactam by recrystallization.|
|Class 14||ε-Caprolactam: ring-opening polymerization||Prepare 6-nylon by ring-opening polymerization.|
|Class 15||Exercise problems to assess the students’ level of understanding and interpretation of the answers||Use the exercise problems to better understand the topics covered, and evaluate one’s own progress.|
Textbook for the Chemical Engineering and Industrial Chemistry Laboratory II 2016 (In Japanese), edited by committee for the chemical engineering and industrial chemistry laboratory (Tokyo Institute of Technology, School of Materials and Chemical Technology, Department of Chemical Science and Engineering). This textbook will be distributed during the first class.
In order to safely perform the experiments (continued), -Basin Operations and Basic Measurements (In Japanese)", 4th Ed., edited by Kagakudojin (Kagakudojin Co., Ltd.), ISBN: 978-4-7598-1834-5
Students will be assessed on their achievements of learning outcomes based on the quality of reports on three themes (83%) and examination (17%).
A student may fail the course if he/she repeatedly comes to class late or does not submit assignments too often.
This is the prerequisite course to take "Chemical Engineering and Industrial Chemistry Laboratory II b/a".
Students must have successfully completed both Chemical Engineering and Industrial Chemistry Laboratory I a/b (CAP.B201.R) and Chemical Engineering and Industrial Chemistry Laboratory I b/a (CAP.B202.R) or have equivalent knowledge.
Takashi Ishizone: tishizon[at]polymer.titech.ac.jp
Hideyuki Otsuka: otsuka[at]polymer.titech.ac.jp
Akira Ohtomo: aohtomo[at]apc.titech.ac.jp
Tetsuro Murahashi: mura[at]apc.titech.ac.jp
Shigekazu Ito: ito.s.ao[at]m.titech.ac.jp
Eiichi Suzuki: esuzuki.e.ac[at]m.titech.ac.jp
Masataka Oishi: moishi[at]o.cc.titech.ac.jp
Toshiki Sawada: tsawada[at]polymer.titech.ac.jp
Raita Goseki: rgoseki[at]polymer.titech.ac.jp
Kohei Yoshimatsu: k-yoshi[at]apc.titech.ac.jp
Contact by e-mail in advance to schedule an appointment.