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Preparation method of thymol

A technology for thymol and cresol, which is applied in the field of preparation of thymol, can solve the problems of many reaction steps, high reaction temperature and high equipment requirements, and achieves the effects of short reaction route, pollution avoidance and easy removal.

Active Publication Date: 2020-08-07
ZHANGZHOU SHUIXIAN PHARMA CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The process has many reaction steps, the catalytic dehydrogenation catalyst has a short service life, and at the same time, there are few sources of upstream raw material citronellal
3), the focus of current research is mainly focused on using m-cresol as the main raw material to prepare thymol, for example, the preparation method disclosed in Chinese invention patent application CN101402551A is to use m-cresol and isopropylation reagent as the main The raw materials are reacted in a fixed-bed reactor, the reaction temperature is 200-300°C, the reaction time is 4-7h, and an inert gas is used as the carrier gas; this scheme requires a special fixed-bed reactor during preparation, and the reaction The temperature is high, the requirements for the equipment are high, and the loading and replacement of the catalyst are cumbersome

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0027] Add m-cresol (100g, 0.92mol) and isopropyl chloride (79.48g, 1.01mol) into a 250mL sealed tube, add concentrated sulfuric acid (12mL) as a reaction aid, and heat up to 120-130°C for 2 hours; After the reaction was lowered to room temperature, add purified water and 200 mL of n-heptane each, wash the organic phase with 50 mL of water, concentrate the organic phase to 100 mL, cool to -5 ~ 0 ° C, precipitate a solid, and filter to obtain a white crystalline powder 54.60 g (0.363 mol , yield: 39.51%).

[0028] The reaction principle of this embodiment is as figure 1 shown.

Embodiment 2

[0030] Add m-cresol (100g, 0.92mol) and isopropyl chloride (79.48g, 1.01mol) into a 250mL sealed tube, add 12mL of concentrated sulfuric acid and 10mL of pyridine butanesulfonic acid bisulfate ionic liquid, and heat up to React at 120-130°C for 1.5 hours; after the reaction has cooled to room temperature, add purified water and n-heptane 200mL each, wash the organic phase twice with 50mL water, concentrate the organic phase to 100mL, cool to -5-0°C, and precipitate a solid. After filtration, 78.50 g (0.523 mol, yield: 56.80%) of white crystalline powder was obtained.

[0031] The molecular formula of the compound (white crystalline powder) is C 10 h 14 O, the molecular weight is 150.22, and the data measured by the MS spectrum is [M+H] + =151.1 (see attached Figure 4 )as well as 1 H-NMR (see attached image 3 ), consistent with the compound structure of thymol. The reaction principle of this embodiment is as figure 2 shown.

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Abstract

The invention relates to a preparation method of thymol, and belongs to the technical field of medicine synthesis. The preparation method comprises the steps: carrying out coupling promotion on m-cresol and isopropyl chloride by adding a reaction auxiliary agent concentrated sulfuric acid and an ionic liquid, sealing a tube, carrying out a reaction at the temperature of 120-130 DEG C for 2 h, carrying out a reaction, cooling, dissolving the product in n-heptane, washing with water, concentrating and crystallizing to obtain the target product. The byproduct obtained by the method is easy to separate from the product, the production cost of the product is reduced, an expensive catalyst is not needed, the reaction time is short, the method is environment-friendly, the conversion rate of the target product is effectively improved, the purification is easy, the purity of the obtained product is high, and the method can be applied to reference substance research.

Description

technical field [0001] The invention relates to a preparation method of thymol, which belongs to the technical field of medicine synthesis. Background technique [0002] Thymol is also known as thymol, thymol, white crystal or crystalline powder, with the fragrance of thyme oil. The relative density is 0.979, the melting point is 48-51°C, and the boiling point is 223°C. Soluble in organic solvents such as ethanol, slightly soluble in water and glycerin. Thymol is originally an antibacterial active ingredient extracted and isolated from Thymus serpyllum L, a Chinese herbal plant of the Labiatae family. Thymol has a strong bactericidal effect, and its bactericidal ability is stronger than that of phenol, and its toxicity is low. It has bactericidal effect on oral mucosa. 1. Fungicidal effect has antiseptic and local anesthetic effects on carious cavity, and is used for disinfection and sterilization of oral cavity and throat, dermatophytosis, actinomycosis and otitis. [00...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/18C07C37/72C07C37/84C07C39/06
CPCC07C37/18C07C37/72C07C37/84C07C39/06
Inventor 昝广友
Owner ZHANGZHOU SHUIXIAN PHARMA CO LTD
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