环己醇制备环己酮的实验改进

doi:10.3866/PKU.DXHX202011045

Abstract

Abstract:

In this paper, the organic chemistry experiment "cyclohexanol oxidation to cyclohexanone" was improved by two green oxidants: potassium bisulfate (Oxone) and trichloroisocyanuric acid (TCCA). A by-product was found in the oxidation with Oxone, and the structure of the by-product was determined by GC-MS. The contents of the target product and by-product under different conditions were studied. When TCCA was used as oxidant to prepare cyclohexanone from cyclohexanol, the higher pure target product was obtained (93%), which can be used to replace the original sodium dichromate oxidation of cyclohexanol to cyclohexanone. Through the introduction of the concept of green chemistry, the students can learn the importance of green chemistry in organic synthesis, and be stimulated the interest in scientific research. It is more important to guide students to pay attention to new discoveries in chemical experiments and to search for the causes or processes of new discoveries, and find out new solutions.

Key words: Green chemistry, Cyclohexanol, Cyclohexanone, Oxone, TCCA

MSC2000:

Wenbin Chen, Yueyang Chen, Bo Chen. Improvement on Preparation of Cyclohexanone from Cyclohexanol[J].University Chemistry, 2021, 36(8): 2011045.

Figures/Tables 8

References 18

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Entry	Cyclohexanol : Oxone : NaBr物质的量之比	环己醇含量/%	副产物(溴代环己酮)含量/%	环己酮含量/%
1	1 : 0.5 : 0.3	22.8	13.2	64.1
2	1 : 0.5 : 0.4	23.2	20.4	53.7
3	1 : 0.5 : 0.5	17.8	24.1	55.9
4	1 : 0.6 : 0.3	12.3	26.1	61.6
5	1 : 0.6 : 0.4	9.6	30.8	59.6
6	1 : 0.6 : 0.5	10.5	52.5	37.0
7	1 : 0.7 : 0.05	72.7	15.0	12.2
8	1 : 0.7 : 0.05 (pH = 7)	57.8	24.4	17.8
9	1 : 0.7 : 0.1	65.9	16.6	17.5
10	1 : 0.7 : 0.1 (pH = 7)	24.7	19.3	56.0
11	1 : 0.7 : 0.3	0.0	36.2	61.5
12	1 : 0.7 : 0.3 (pH = 7)	9.1	11.9	79.0
13	1 : 0.7 : 0.4	0.7	54.2	45.1
14	1 : 0.7 : 0.5	1.1	52.0	46.9

Entry	环己醇/TCCA/碱的物质的量之比	碱	环己醇含量/%	副产物含量/%	环己酮含量/%
1	1 : 0.43 : 1.2	吡啶	0	5.5	93.5
2	1 : 0.43 : 1.2	K₂CO₃	9.9	84.4	7.6

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Improvement on Preparation of Cyclohexanone from Cyclohexanol

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