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Method of preparing 3-isopropyl-5-cresol and carvacrol with 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 low selectivity of single products, difficult to separate, etc., and achieves the realization of reusable, High utilization rate of raw materials and easy recovery

Active Publication Date: 2019-01-18
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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  • Method of preparing 3-isopropyl-5-cresol and carvacrol with 3-carene
  • Method of preparing 3-isopropyl-5-cresol and carvacrol with 3-carene
  • Method of preparing 3-isopropyl-5-cresol and carvacrol with 3-carene

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Experimental program
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Effect test

Embodiment 1

[0047] Embodiment 1 prepares product I

[0048] Weigh 5g anhydrous CrO 3 , configured as a 5% aqueous solution, weighed 5g of neutral alumina (100 mesh), added to the above aqueous solution, stirred at room temperature for 24h, filtered, and dried at 110°C for 6h; weighed 100g of 3-carene, 3.0g of CrO 3 -Al 2 o 3 Add them together into the reaction flask, pass oxygen, and control the air intake to 20mL / min, and start stirring at room temperature to react; take samples every 1h, centrifuge the catalyst, and perform gas chromatography analysis; after 10h, the gas phase analysis results: 3-carene 41.28%, 2-carene 11.65%, 4-carene 3.31%, 5-carene 35.60%, analysis results after 11 hours: 3-carene 39.98%, 2-carene 11.33%, 4-carene 3.87%, 5-carene 35.32%, stop the reaction, the reaction solution is centrifuged, and the catalyst is recovered.

Embodiment 2

[0049] Embodiment 2 prepares product I

[0050] Catalyst is recycled for the 3rd time, other technological conditions are the same as embodiment 1, gas phase analysis result after 10h: 3-carene 46.62%, 2-carene 10.83%, 4-carene 2.80%, 5-carene 31.29%.

Embodiment 3

[0051] Embodiment 3 prepares product I

[0052] Catalyst addition 5.0g, all the other technological conditions are the same as embodiment 1, gas phase analysis result after 10h: 3-carene 39.41%, 2-carene 11.83%, 4-carene 3.83%, 5-carene 35.03%.

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Abstract

The invention discloses a method of preparing 3-isopropyl-5-cresol and carvacrol with 3-carene. The method comprises the following steps that 3-carene is reacted with oxygen at a room temperature to produce a product I under the catalysis of CrO3-Al2O3, wherein the product I is prepared from the main components including 5-carone, 2-carone and 4-carone with the selectivity ratio being about 10.8 to 3.5 to 1.0; the product I is distilled to recover 3-carene, wherein the recovery rate is larger than 80 percent, and the recovery purity is larger than 94 percent; the residual components are converted to a product II at 230 DEG C under catalysis of a 13X type molecular sieve, and reduced pressure distillation is performed on the product II to obtain a mixed phenol product with the purity largerthan 96 percent, wherein the product II is prepared from the main components including 3-isopropyl-5-cresol and carvacrol, the raw material conversion rate is 100 percent, the total selectivity of phenolic products can reach 98 percent, and the selectivity ratio of the two phenolic products is about 2.2 to 1.0; and column chromatography isolation is performed on the product II to obtain 3-isopropyl-5-cresol and carvacrol with the purities larger than 97 percent 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 and carvacrol through oxidation and isomerization of 3-carene respectively. - Cresol and carvacrol method. Background technique [0002] 3-isopropyl-5-cresol, also known as 5-isopropyl-3-cresol, 5-thymol, m-thymol, etc., is isomers with thymol and carvacrol, and has Special aroma similar to thymol. 3-isopropyl-5-cresol itself has biological activities such as anti-corrosion, anti-oxidation, antibacterial and insecticidal, and is also a key precursor for the synthesis of other active substances, such as carbamate derivatives of alkyl-substituted cresols It is an important class of pesticides, and due to the meta-substitution activity > ortho > para, secondary alkyl activity > tertiary alkyl > n-alkyl, 4-carbon chain > 3-carbon chain or 5-carbon chain > other carbon chains , so...

Claims

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Application Information

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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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