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A method for preparing 3-isopropyl-5-cresol and carvacrol from 3-carene

A technology of isopropyl and carvacrol, applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., can solve the problems of difficult separation, low selectivity of single product, etc., and achieve high utilization rate of raw materials. Effect

Active Publication Date: 2021-09-17
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A key problem in the oxidation reaction of 3-carene is that the selectivity of single products is relatively low, and they are not easy to separate due to their similar properties. This may be due to the lack of research on the application of components such as 5-carene and 2-carene One of the reasons, so if the oxidation product can be effectively utilized without separation, it is also a good way to realize the value-added utilization of 3-carene

Method used

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  • A method for preparing 3-isopropyl-5-cresol and carvacrol from 3-carene
  • A method for preparing 3-isopropyl-5-cresol and carvacrol from 3-carene
  • A method for preparing 3-isopropyl-5-cresol and carvacrol from 3-carene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1 Preparation of product I

[0048] Weigh 5g of anhydrous CrO 3 , configured as a 5% aqueous solution, weigh 5 g of neutral alumina (100 mesh), add it to the above aqueous solution, stir at room temperature for 24 h, filter, and dry at 110 °C for 6 h; weigh 100 g of 3-carene, 3.0 g of CrO 3 -Al 2 O 3 Add to the reaction flask together, pass oxygen, and control the air intake to be 20mL / min, turn on stirring at room temperature to carry out the reaction; take samples every 1h, separate the catalyst by centrifugation, and conduct gas chromatography analysis; after 10h, gas analysis results: 3-carene 41.28%, 2-careone 11.65%, 4-careone 3.31%, 5-careone 35.60%, analysis results after 11h: 3-carene 39.98%, 2-carene 11.33%, 4-carene 3.87%, 5-careone 35.32%, the reaction was stopped, the reaction solution was centrifuged, and the catalyst was recovered.

Embodiment 2

[0049] Example 2 Preparation of product I

[0050] The catalyst was recycled for the third time, and other process conditions were the same as those in Example 1. The results of gas phase analysis after 10 hours: 3-carene 46.62%, 2-carene 10.83%, 4-carene 2.80%, 5-carene 31.29%.

Embodiment 3

[0051] Example 3 Preparation of product I

[0052] The amount of catalyst added was 5.0 g, and the rest of the process conditions were the same as those of Example 1. The results of gas phase analysis after 10 hours: 39.41% of 3-carene, 11.83% of 2-carene, 3.83% of 4-carene, and 35.03% of 5-carene.

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Abstract

The invention discloses a method for preparing 3-isopropyl-5-cresol and carvacrol from 3-carene. 3‑carene in CrO 3 ‑Al 2 o 3 Under catalysis, it reacts with oxygen at room temperature to form product Ⅰ: the main components include 5-carene, 2-carene and 4-carene, and the selectivity ratio of the three ketone products is about 10.8:3.5:1.0; product Ⅰ 3-carene is recovered by distillation, the recovery rate is greater than 80%, and the recovery purity is greater than 94%; the remaining components are converted into product II at 230°C under the catalysis of 13X molecular sieve: the main components include 3-isopropyl-5-formazan Phenol and carvacrol, the conversion rate of raw materials is 100%, the total selectivity of phenolic products can reach 98%, the selectivity ratio of the two phenolic products is about 2.2:1.0, and the product II is distilled under reduced pressure to obtain a mixed product with a purity greater than 96%. Phenol product; Product II is separated by column chromatography to obtain 3-isopropyl-5-cresol and carvacrol with a purity greater than 97% respectively.

Description

technical field [0001] The invention relates to a method for preparing 3-isopropyl-5-cresol and carvacrol from 3-carene, in particular to a method for preparing 3-isopropyl-5-cresol by oxidation and isomerization of 3-carene respectively. - Method for cresol and carvacrol. Background technique [0002] 3-Isopropyl-5-cresol, also known as 5-isopropyl-3-cresol, 5-thymol, m-thymol, etc., and thymol and carvacrol are isomers of each other, with Special aroma similar to thymol. 3-Isopropyl-5-cresol itself has biological activities such as antiseptic, antioxidant, antibacterial and insecticidal, and is also a key precursor for the synthesis of various other active substances, such as carbamate derivatives of alkyl-substituted cresols It is an important class of pesticides, and due to meta-substitution activity > ortho > para, secondary alkyl activity > tertiary alkyl > n-alkyl, 4 carbon chains > 3 carbon chains or 5 carbon chains > other carbon chains , so the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C39/06C07C37/07C07C49/627C07C45/34B01J23/26
CPCB01J23/002B01J23/26C07C37/07C07C45/34C07C2602/20C07C49/627C07C39/06Y02P20/52
Inventor 王婧赵振东卢言菊徐士超古研陈玉湘毕良武
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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