CN104177233B - A kind of synthetic method of thymol - Google Patents

A kind of synthetic method of thymol Download PDF

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CN104177233B
CN104177233B CN201410457250.8A CN201410457250A CN104177233B CN 104177233 B CN104177233 B CN 104177233B CN 201410457250 A CN201410457250 A CN 201410457250A CN 104177233 B CN104177233 B CN 104177233B
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thymol
catalyzer
reaction
menthol
gac
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CN104177233A (en
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帅放文
章家伟
王向峰
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HUNAN XIANGYIKANG PHARMACEUTICAL Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/78—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with alkali- or alkaline earth metals

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a kind of synthetic method of thymol, take specifically piperitone as raw material, at activated carbon supported Ni/Na 2siO 3under catalyst action, de-hydroformylation step produces thymol.Under the method reaction conditions gained by product be easy between product be separated the production cost reducing product, without the need to the catalyzer of costliness, and the reaction times is shorter, environmentally friendly.

Description

A kind of synthetic method of thymol
Technical field
The present invention relates to a kind of synthetic method of bulk drug thymol, belong to biomedicine field.
Background technology
Thymol is referred to as again thymol, thymol, chemical name 5-thymol.Thymol has stronger germicidal action, sterilizing ability is stronger than phenol, and toxicity is low, there is sterilization to oral mucosa, fungicidal action has anticorrosion, local anesthetic action to carious tooth chamber, for the disinfection of oral cavity, throat, tinea, actinomycosis and otitis.Can tra cheo-oesophageal voice be promoted, be conducive to the secretion of tracheal mucus, easily play phlegm-dispelling functions, then be added with germicidal action, therefore can be used for treating trachitis, Whooping cough etc.Have very strong acaricidal action, the solution 24h of 1% solution mortality ratio half an hour 100%, 0.03% kills 100%.Also can be used as ascarifuge agent.Thymol 0.05% ~ 0.2% solution has and stronger kills protoscolex effect, and can reach the effect that 100% kills protoscolex in 5 ~ 10min, effect is reliable rapidly, and toxicity is little.
Along with the expansion of product scope taking thymol as development of raw materials, the demand of thymol is also by increasing.China's thymol main source extracts or import from thyme oil, wild marjoram oil, sweet basil wet goods.Because the production cost extracting thymol from plant is high, and process need uses a large amount of acid, alkaline solution, and large to environmental stress, therefore, chemosynthesis thymol has the very large market space.
At present, the chemical synthesis process of thymol mainly contains following several:
Take geraniol as raw material, first catalysis closed loop generates isopulegol, generates thymol in catalytic dehydrogenation.This method technique is simple, and the productive rate of thymol is high, but the preparation process of its dehydrogenation catalyst used is complicated, and catalyzer is short for work-ing life.
α-pinene can obtain pinanone through catalyzed oxidation, thymol is obtained again through catalytic pyrolysis, the productive rate of this method synthetic musk grass phenol is low, and process need perhydronaphthalene or other nonpolar large volume organism are as solvent, although solvent can recycle, certain pollution is still had to environment.
Abroad, the document of report synthetic musk grass phenol method is more, the material containing sec.-propyl such as meta-cresol and 2-Halopropane, propylene or Virahol is mainly adopted to be raw material, carry out the synthesis method of fourier alkylated reaction. before the eighties in 20th century, this method is mainly alkylating reagent with propylene, require to carry out under elevated pressure conditions, and easily generate isomer and many induced by alkyl hydroxybenzene, so that thymol productive rate is lower, the thick product obtained also will through isomer separation and transposition, operation more complicated.Start in the 90's of 20th century, the research of this synthetic method mainly concentrates on the catalyzer aspect found and be applicable to, such one side can improve selection rate and the productive rate of thymol, production process can be made to carry out at ambient pressure on the other hand, and use acid-base solution and organic solvent less. from document in recent years, the catalyzer of selection mainly contains oxide compound and molecular sieve two class solid acid catalyst.
In addition, application number is the preparation method that refer to a kind of thymol in the patent of 200810219106.5.The method adopts meta-cresol and Virahol to be raw material, reacts in fixed-bed reactor, uses γ-Al 2o 3catalyzer, at temperature of reaction 200-350 DEG C, prepares thymol.The rich raw material sources of this technique, its productive rate is 40%.
Yang Ze elm (synthesis [J] of thymol. catalysis journal, 1990,11 (1)) etc. people develops with geranial is raw material, catalysis closed loop becomes isopulegol, catalytic dehydrogenation becomes the method for room vanilla phenol again, its productive rate can reach more than 80%, but this production method upstream raw material geranial used source is few, its industrial application of limit value.
Enemy the Kunlun (progress [J] of thymol. fragrance flavor and cosmetic, 2008, (2)) etc. people report a kind of with menthol or piperitone for raw material, use Ni to synthesize thymol for catalyzer in a kettle., productive rate is respectively 65% and 63%.
Menthol is the one of lopps monoterpene, is mainly present in mint.Mint is wide in China's distribution, ecological adaptation amplitude is large.Menthol can be separated from spearmint oil and obtain, and also can be manufactured by geranial.Menthol is a kind of important spices.Levorotatory menthol is due to its cooling effect, a large amount of for cigarette, makeup, toothpaste, chewing gum, sweet food and medicine, inuncts, play that local is antipruritic, pain relieving, the effect such as refrigerant (mechanism: the cold receptor on skin irritation but do not cause actual temperature change) and slight local anaesthesia.And synthesize the mixture that menthol is various isomer, be worth little.
Summary of the invention
The object of the invention is to, provide that a kind of condition is simple, environmental protection, can the chemical process of continuous synthesis thymol, overcome the defect that the aspects such as existing thymol production technology Raw, technique and environmental protection exist.
The present invention for starting raw material, obtains menthol gas, under the conveying of carrier gas, with activated carbon supported Ni/ Na through gasification with the menthol of DL 2siO 3catalyzer generation dehydrogenation reaction, namely obtains thymol through condensation, purifying.
Further, the input speed of reaction substrate menthol gasification is 0.1-0.6ml/min.
Further, reaction is using nitrogen as carrier gas, and induction air flow ratio is 18-30ml/min, and in reaction system, temperature is between 547-661K.
Described catalyzer is activated carbon supported Ni/ Na 2siO 3, under the effect of this catalyzer, reaction solution reacts at a certain temperature and generates thymol, and its by product is piperitone or is p-Methylisopropylbenzene.
This catalyzer can be produced by scheme below:
Gac 15%HNO 3after solution soaking one night, filter also with boiling water washing, the remaining acid of removing, is washed till PH>=7 of system.Moist gac at room temperature dries, then is placed in baking oven 393K dried overnight, and then roasting 5h under 673 ~ 773K in retort furnace, for subsequent use.
Nickelous nitrate and water glass are dissolved in appropriate water, add in gac, the mass ratio between three is nickelous nitrate: 18 ~ 25 parts, water glass: 3 ~ 7 parts, gac: 72 ~ 75 parts.At room temperature stir 30min.Then desolventizing is removed through underpressure distillation, solid temperature programming drying in an oven (300K-400K) 10h.Dried solid is used hydrogen reducing 5h under 650-720k, after reduction, obtains activated carbon supported Ni/ Na 2siO 3catalyzer.
Beneficial effect of the present invention is: relative to traditional take meta-cresol as raw material production thyme method, the by product of present method reaction is few, and the boiling point nature difference between by product and product makes greatly product purification difficulty decline, and improves the quality of product.In addition, menthol abundance, can effectively solve raw-material problem.In addition, present method have employed fluidization, can continuous seepage thymol, improves thymol production capacity.By the transformation to single metalNicatalyst, obtain an efficient activated carbon supported Ni/ Na 2siO 3catalyzer.The Ni/ Na that present method adopts 2siO 3water glass in catalyzer can strengthen Ni absorption on the activated carbon, and in the operation of high-temperature bake Na 2siO 3the cavernous structure formed also enhances the catalytic effect of unit mass catalyzer to a certain extent.
Embodiment
Further illustrate the present invention program below by way of several embodiment, should be appreciated that following all embodiments are not limitation of the invention further.
Embodiment 1 catalyst preparing
After taking 15%HNO3 solution soaking one night of gac 7.2g 30ml, filter also with boiling water washing, the remaining acid of removing, is washed till PH >=7 of system.Moist gac at room temperature dries, then is placed in baking oven 393K dried overnight, and then roasting 5h under 673 ~ 773K in retort furnace, for subsequent use.18g nickelous nitrate and 0.3g water glass are dissolved in appropriate water, add in above-mentioned gac.At room temperature stir 30min.Then desolventizing is removed through underpressure distillation, solid temperature programming drying in an oven (300K-400K) 10h.Dried solid is used hydrogen reducing 5h under 650-720k, after reduction, obtains activated carbon supported Ni/ Na2SiO3 catalyzer.
Embodiment 2 catalyst preparing
After taking 15%HNO3 solution soaking one night of gac 7.5g 30ml, filter also with boiling water washing, the remaining acid of removing, is washed till PH >=7 of system.Moist gac at room temperature dries, then is placed in baking oven 393K dried overnight, and then roasting 5h under 673 ~ 773K in retort furnace, for subsequent use.25g nickelous nitrate and 0.7g water glass are dissolved in appropriate water, add in above-mentioned gac.At room temperature stir 30min.Then desolventizing is removed through underpressure distillation, solid temperature programming drying in an oven (300K-400K) 10h.Dried solid is used hydrogen reducing 5h under 650-720k, after reduction, obtains activated carbon supported Ni/ Na2SiO3 catalyzer.
Embodiment 3 catalyst preparing
After taking 15%HNO3 solution soaking one night of gac 7.5g 30ml, filter also with boiling water washing, the remaining acid of removing, is washed till PH >=7 of system.Moist gac at room temperature dries, then is placed in baking oven 393K dried overnight, and then roasting 5h under 673K in retort furnace, for subsequent use.25g nickelous nitrate and 0.3g water glass are dissolved in appropriate water, add in above-mentioned gac.At room temperature stir 30min.Then desolventizing is removed through underpressure distillation, solid temperature programming drying in an oven (300K-400K) 10h.Dried solid is used hydrogen reducing 5h under 650k, after reduction, obtains activated carbon supported Ni/ Na2SiO3 catalyzer.
Embodiment 4
The catalyzer that Example 1 prepares joins reaction fluidized-bed, opens carrier gas N 2get rid of the air in reaction system, logical N 2air-flow 30min.System temperature is risen to 547K after getting rid of by reaction system air, and after system temperature reaches set(ting)value, pass into menthol gas through having gasified and nitrogen to system, the flow velocity of menthol gas is 0.4ml/min, the flow velocity of nitrogen is 23ml/min.The yield 70% of thymol.
Embodiment 5
The catalyzer that Example 1 prepares joins reaction fluidized-bed, opens carrier gas N 2get rid of the air in reaction system, logical N 2air-flow 30min.System temperature is risen to 635K after getting rid of by reaction system air, and after system temperature reaches set(ting)value, pass into menthol gas through having gasified and nitrogen to system, the flow velocity of menthol gas is 0.4ml/min, the flow velocity of nitrogen is 23ml/min.The yield 82% of thymol.
Embodiment 6
The catalyzer that Example 1 prepares joins reaction fluidized-bed, opens carrier gas N 2get rid of the air in reaction system, logical N 2air-flow 30min.System temperature is risen to 661K after getting rid of by reaction system air, and after system temperature reaches set(ting)value, pass into menthol gas through having gasified and nitrogen to system, the flow velocity of menthol gas is 0.4ml/min, the flow velocity of nitrogen is 23ml/min.The yield 79% of thymol.
Embodiment 7
The catalyzer that Example 2 prepares joins reaction fluidized-bed, opens carrier gas N 2get rid of the air in reaction system, logical N 2air-flow 30min.System temperature is risen to 635K after getting rid of by reaction system air, and after system temperature reaches set(ting)value, pass into menthol gas through having gasified and nitrogen to system, the flow velocity of menthol gas is 0.1ml/min, the flow velocity of nitrogen is 23ml/min.The yield 75% of thymol.
Embodiment 8
The catalyzer that Example 2 prepares joins reaction fluidized-bed, opens carrier gas N 2get rid of the air in reaction system, logical N 2air-flow 30min.System temperature is risen to 635K after getting rid of by reaction system air, and after system temperature reaches set(ting)value, pass into menthol gas through having gasified and nitrogen to system, the flow velocity of menthol gas is 0.6ml/min, the flow velocity of nitrogen is 23ml/min.The yield 69% of thymol.
Embodiment 9
The catalyzer that Example 2 prepares joins reaction fluidized-bed, opens carrier gas N 2get rid of the air in reaction system, logical N 2air-flow 30min.System temperature is risen to 635K after getting rid of by reaction system air, and after system temperature reaches set(ting)value, pass into menthol gas through having gasified and nitrogen to system, the flow velocity of menthol gas is 0.4ml/min, the flow velocity of nitrogen is 18ml/min.The yield 75% of thymol.
Embodiment 10
The catalyzer that Example 3 prepares joins reaction fluidized-bed, opens carrier gas N 2get rid of the air in reaction system, logical N 2air-flow 30min.System temperature is risen to 635K after getting rid of by reaction system air, and after system temperature reaches set(ting)value, pass into menthol gas through having gasified and nitrogen to system, the flow velocity of menthol gas is 0.4ml/min, the flow velocity of nitrogen is 30ml/min.The yield 73% of thymol.
Embodiment 11
The catalyzer that Example 3 prepares joins reaction fluidized-bed, opens carrier gas N 2get rid of the air in reaction system, logical N 2air-flow 30min.System temperature is risen to 635K after getting rid of by reaction system air, and after system temperature reaches set(ting)value, pass into menthol gas through having gasified and nitrogen to system, the flow velocity of menthol gas is 0.4ml/min, the flow velocity of nitrogen is 23ml/min.The yield 75% of thymol.
Embodiment 12
The catalyzer that Example 3 prepares joins reaction fluidized-bed, opens carrier gas N 2get rid of the air in reaction system, logical N 2air-flow 30min.System temperature is risen to 635K after getting rid of by reaction system air, and after system temperature reaches set(ting)value, pass into menthol gas through having gasified and nitrogen to system, the flow velocity of menthol gas is 0.4ml/min, the flow velocity of nitrogen is 23ml/min.The yield 73% of thymol.
Embodiment 13
The catalyzer that Example 3 prepares joins reaction fluidized-bed, opens carrier gas N 2get rid of the air in reaction system, logical N 2air-flow 30min.System temperature is risen to 635K after getting rid of by reaction system air, and after system temperature reaches set(ting)value, pass into menthol gas through having gasified and nitrogen to system, the flow velocity of menthol gas is 0.4ml/min, the flow velocity of nitrogen is 23ml/min.The yield 80% of thymol.
Comparative example 1
The catalyzer that Example 3 prepares joins reaction fluidized-bed, opens carrier gas N 2get rid of the air in reaction system, logical N 2air-flow 30min.System temperature is risen to 635K after getting rid of by reaction system air, and after system temperature reaches set(ting)value, pass into menthol gas through having gasified and nitrogen to system, the flow velocity of menthol gas is 0.6ml/min, the flow velocity of nitrogen is 33ml/min.The yield 61% of thymol.
Comparative example 2
The catalyzer that Example 1 prepares joins reaction fluidized-bed, opens carrier gas N 2get rid of the air in reaction system, logical N 2air-flow 30min.System temperature is risen to 690K after getting rid of by reaction system air, and after system temperature reaches set(ting)value, pass into menthol gas through having gasified and nitrogen to system, the flow velocity of menthol gas is 0.4ml/min, the flow velocity of nitrogen is 23ml/min.The yield 65% of thymol.
Comparative example 3
The catalyzer that Example 2 prepares joins reaction fluidized-bed, opens carrier gas N 2get rid of the air in reaction system, logical N 2air-flow 30min.System temperature is risen to 635K after getting rid of by reaction system air, and after system temperature reaches set(ting)value, pass into menthol gas through having gasified and nitrogen to system, the flow velocity of menthol gas is 0.8ml/min, the flow velocity of nitrogen is 23ml/min.The yield 65% of thymol.

Claims (1)

1. a production method for thymol, comprises step raw material, carrier gas and catalyzer catalyzed reaction in reaction vessel being obtained finished product thymol, it is characterized in that, take menthol as raw material, menthol gas is obtained, under the conveying of carrier gas, with activated carbon supported Ni/Na through gasification 2siO 3catalyzer generation dehydrogenation reaction, namely obtains thymol through condensation, purifying;
The preparation of described catalyzer is prepared by the following method: (1) gac 15%HNO 3after solution soaking one night, filter also with boiling water washing, the remaining acid of removing, is washed till PH>=7 of system; Moist gac at room temperature dries, then is placed in baking oven 393K dried overnight, and then roasting 5h under 673 ~ 773K in retort furnace, for subsequent use;
(2) nickelous nitrate and water glass are dissolved in appropriate water, add in gac, mass ratio between three is nickelous nitrate: 18 ~ 25 parts, water glass: 3 ~ 7 parts, gac: 72 ~ 75 parts, at room temperature stir 30min, then through underpressure distillation except desolventizing, solid in an oven temperature programming to 300K-400K, dry 10h, dried solid is used hydrogen reducing 5h under 650-720K, after reduction, obtains activated carbon supported Ni/Na 2siO 3catalyzer;
The input speed of described reaction substrate menthol gas is 0.1-0.6ml/min;
Described carrier gas is nitrogen, and induction air flow ratio is 18-30ml/min, and in reaction system, temperature is between 547-661K.
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CN105693471B (en) * 2016-01-21 2019-01-15 上海延安药业（湖北）有限公司 The preparation method of thymol
CN110354909B (en) * 2019-07-18 2022-01-07 万华化学集团股份有限公司 Catalyst system for preparing L-menthol and preparation method and application thereof

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