CN103193638A - Synthetic method of perfume o-tert-butylcyclohexyl acetate - Google Patents
Synthetic method of perfume o-tert-butylcyclohexyl acetate Download PDFInfo
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- CN103193638A CN103193638A CN2012100031000A CN201210003100A CN103193638A CN 103193638 A CN103193638 A CN 103193638A CN 2012100031000 A CN2012100031000 A CN 2012100031000A CN 201210003100 A CN201210003100 A CN 201210003100A CN 103193638 A CN103193638 A CN 103193638A
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Abstract
The invention relates to a chemical synthetic method, and concretely relates to a synthetic method of a perfume o-tert-butylcyclohexyl acetate. The synthetic method comprises the following steps: reacting a raw material phenol with isobutene under the catalysis of anhydrous aluminum trichloride to obtain o-tert-butyl phenol, carrying out catalytic hydrogenation of o-tert-butyl phenol under the catalysis of Raney nickel to obtain o-tert-butyl cyclohexanol, and carrying out an esterification reaction of o-tert-butyl cyclohexanol and acetic anhydride under the catalysis of anhydrous sodium acetate to obtain o-tert-butylcyclohexyl acetate. The method has the advantages of mild reaction conditions, safe and convenient operation, high reaction yield, fine and strong fragrance of the obtained product, raw material source enlargement and raw material cost saving because of the adoption of industrially cheap phenol and isobutene as initial raw materials, total synthetic reaction yield improvement, suitableness for the industrial adoption, and good economic benefit.
Description
Technical field
The present invention relates to a kind of chemical synthesis process, be specifically related to the adjacent uncle of a kind of spices acetic acid
The synthetic method of butyl cyclohexyl ester.
Background technology
Verdox has the flowers and fruits odor type because of it, be often used in soap compound and the cosmetic essence prescription, the production method reaction conditions of traditional verdox is violent, inconvenient operation, reaction yield is low, is not suitable for the scale operation of industry.
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Summary of the invention
The synthetic method that the purpose of this invention is to provide a kind of spices verdox, its reaction conditions gentleness, easy-to-operate, the reaction yield height, product fragrance is finer and smoother and strong; Adopting industrial phenol cheap and easy to get and iso-butylene is starting raw material, has enlarged raw material sources, has saved raw materials cost, has improved the building-up reactions total yield, is adapted at industrial employing, and favorable economic benefit is arranged.
In order to solve the existing problem of background technology, the present invention takes following technical scheme: its synthetic method was divided into for three steps: 1, o-tert-butylphenol is synthetic: in the there-necked flask that thermometer, electric mixer, gas duct, drying tube are housed, add phenol 110-120g, dense H
2SO
42-3g, anhydrous AlCl
36-10g; Be warming up to 50 ℃, under violent stirring, feed isobutene gas, when the question response thing increases weight to the 60-70g left and right sides, stop to feed iso-butylene, be warming up to 80 ℃ of stirring reaction 2 hr again, with 230ml * 2 time hot wash reactant, use water jet pump pressure reducing and steaming moisture again, then adopt vacuum distillation method that crude product is steamed, the gained crude product is with 240ml sherwood oil recrystallization, and freezing, filtration, drying get o-tert-butylphenol 125-135g;
2, verdol is synthetic: the there-necked flask that thermometer, electric mixer, dropping funnel and gas duct will be housed is put in the water-bath, add Ni-Al-Cr alloy powder 70-80g, distilled water 150-160ml, under agitation, slowly drip 30 % NaOH solution, 50 ℃ of control temperature of reaction dropwise about about 2hr, continuation is stirring reaction 1hr under this temperature, leave standstill, the whole sedimentations of catalyzer to be generated, supernatant liquid inclines; Successively divide with 30 % NaOH solution and distilled water to be washed till pH ≈ 8 for several times, get active Raney Ni catalyzer, with alcohol or water logging not store;
With above-mentioned o-tert-butylphenol 95-105g, be dissolved in the 110ml dehydrated alcohol, place the 500ml autoclave altogether with active Raney Ni catalyzer 15-25g, at 145-150 ℃ of temperature, pressure 55-60 kg/cm
2Carry out hydrogenation reaction 3.5 hr under the condition, the question response thing is chilled near room temperature, takes out, and filters, reclaims ethanol, underpressure distillation, gets verdol 95-105g;
3, verdox is synthetic: verdol 295-305 g, fully dry sodium acetate, anhydrous 15-25g, acetic anhydride 205-215g are put in the flask, under electric mantle heating in 145-150 ℃ of 5 hr that reflux, after the reactant cooling, water, 2% NaOH solution, saturated common salt water washing successively, vacuum fractionation gets verdox 370-380g.
The present invention has following beneficial effect: its reaction conditions gentleness, easy-to-operate, the reaction yield height, product fragrance is finer and smoother and strong, adopting industrial phenol cheap and easy to get and iso-butylene is starting raw material, enlarge raw material sources, saved raw materials cost, improved the building-up reactions total yield, be adapted at industrial employing, favorable economic benefit is arranged.
Embodiment:
This embodiment is taked following technical scheme: 1, o-tert-butylphenol is synthetic: in the there-necked flask that thermometer, electric mixer, gas duct, drying tube are housed, add phenol 113g, dense H
2SO
42.3g, anhydrous AlCl
39g is warming up to 50 ℃, under violent stirring, feed isobutene gas, when the question response thing increases weight to the 62g left and right sides, stop to feed iso-butylene, be warming up to 80 ℃ of stirring reaction 2 hr again, with 230ml * 2 time hot wash reactant, use water jet pump pressure reducing and steaming moisture again, adopt vacuum distillation method that crude product is steamed then, gained crude product 240ml sherwood oil recrystallization, freezing, filtration, drying get o-tert-butylphenol 128g;
2, verdol is synthetic: the there-necked flask that thermometer, electric mixer, dropping funnel and gas duct will be housed is put in the water-bath, add Ni-Al-Gr alloy powder 76g, distilled water 155ml, under agitation, slowly drip 30 % NaOH solution, 50 ℃ of control temperature of reaction dropwise about about 2hr, continuation is stirring reaction 1hr under this temperature, leave standstill, the whole sedimentations of catalyzer to be generated, supernatant liquid inclines; Successively divide with 30 % NaOH solution and distilled water to be washed till pH ≈ 8 for several times, get active Raney Ni catalyzer, the water submergence stores;
With above-mentioned o-tert-butylphenol 100g, be dissolved in the 110ml dehydrated alcohol, place the 500ml autoclave altogether with active Raney Ni catalyzer 20g, at 145-150 ℃ of temperature, pressure 55-60 kg/cm
2Carry out hydrogenation reaction 3.5 hr under the condition, the question response thing is chilled near room temperature, takes out, and filters, reclaims ethanol, underpressure distillation, obtains verdol 101.5g;
3, verdox is synthetic: verdol 300 g, fully dry sodium acetate, anhydrous 19g, acetic anhydride 210g are put in the flask, under electric mantle heating in 145-150 ℃ of 5 hr that reflux, after the reactant cooling, water, 2% NaOH solution, saturated common salt water washing successively, vacuum fractionation gets verdox 376g.
This embodiment reaction conditions gentleness, easy-to-operate, the reaction yield height, product fragrance is finer and smoother and strong, adopting industrial phenol cheap and easy to get and iso-butylene is starting raw material, enlarge raw material sources, saved raw materials cost, improved the building-up reactions total yield, be adapted at industrial employing, favorable economic benefit is arranged.
Claims (4)
1. the synthetic method of a spices verdox is characterized in that its synthetic method was divided into for three steps: 1, o-tert-butylphenol is synthetic; 2, verdol is synthetic; 3, verdox is synthetic.
2. the synthetic method of a kind of spices verdox according to claim 1, the synthesis step that it is characterized in that described o-tert-butylphenol is: in the there-necked flask that thermometer, electric mixer, gas duct, drying tube are housed, add the dense H of phenol 110-120g
2SO
42-3g, anhydrous AlCl
36-10g; Be warming up to 50 ℃, under violent stirring, feed isobutene gas, when the question response thing increases weight to the 60-70g left and right sides, stop to feed iso-butylene, be warming up to 80 ℃ of stirring reaction 2 hr again, with 230ml * 2 time hot wash reactant, use water jet pump pressure reducing and steaming moisture again, then adopt vacuum distillation method that crude product is steamed, the gained crude product is with 240ml sherwood oil recrystallization, and freezing, filtration, drying get o-tert-butylphenol 125-135g.
3. the synthetic method of a kind of spices verdox according to claim 1, the synthesis step that it is characterized in that described verdol is: thermometer will be housed, electric mixer, the there-necked flask of dropping funnel and gas duct is put in the water-bath, add Ni-Al-Gr alloy powder 70-80g, distilled water 150-160ml, under agitation, slowly drip 30 % NaOH solution, 50 ℃ of control temperature of reaction, about about 2hr, dropwise, continuation is stirring reaction 1hr under this temperature, leave standstill, the whole sedimentations of catalyzer to be generated, supernatant liquid inclines; Successively divide with 30 % NaOH solution and distilled water to be washed till pH ≈ 8 for several times, get active Raney Ni catalyzer, the water submergence stores;
With above-mentioned o-tert-butylphenol 95-105g, be dissolved in the 110ml dehydrated alcohol, place the 500ml autoclave altogether with active Raney Ni catalyzer 15-25g, at 145-150 ℃ of temperature, pressure 55-60 kg/cm
2Carry out hydrogenation reaction 3.5 hr under the condition, the question response thing is chilled near room temperature, takes out, and filters, reclaims ethanol, underpressure distillation, gets verdol 95-105g.
4. the synthetic method of a kind of spices verdox according to claim 1, the synthesis step that it is characterized in that described verdox is: verdol 295-305 g, fully dry sodium acetate, anhydrous 15-25g, acetic anhydride 205-215g are put in the flask, under electric mantle heating in 145-150 ℃ of 5 hr that reflux, after the reactant cooling, water, 2% NaOH solution, saturated common salt water washing successively, vacuum fractionation gets verdox 370-380g.
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| Application Number | Priority Date | Filing Date | Title |
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| CN2012100031000A CN103193638A (en) | 2012-01-06 | 2012-01-06 | Synthetic method of perfume o-tert-butylcyclohexyl acetate |
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| CN2012100031000A CN103193638A (en) | 2012-01-06 | 2012-01-06 | Synthetic method of perfume o-tert-butylcyclohexyl acetate |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104610053A (en) * | 2015-01-23 | 2015-05-13 | 中国林业科学研究院林产化学工业研究所 | Rosin derivate for soldering flux and preparation method |
| CN107652183A (en) * | 2017-10-17 | 2018-02-02 | 安徽华业香料合肥有限公司 | A kind of synthetic method of tert-butylcyclohexyl ethyl carbonate spices |
| CN107698450A (en) * | 2017-10-17 | 2018-02-16 | 安徽华业香料合肥有限公司 | A kind of synthetic method of iris ester spices |
| CN107759447A (en) * | 2017-10-17 | 2018-03-06 | 安徽华业香料合肥有限公司 | A kind of production method of tert-butylcyclohexyl ethyl carbonate synthetic perfume |
| CN107827712A (en) * | 2017-10-31 | 2018-03-23 | 安徽华业香料合肥有限公司 | A kind of production method of verdox synthetic perfume |
| CN107840797A (en) * | 2017-10-17 | 2018-03-27 | 安徽华业香料合肥有限公司 | A kind of production method of iris ester synthetic perfume |
| CN107879932A (en) * | 2017-10-31 | 2018-04-06 | 安徽华业香料合肥有限公司 | A kind of synthetic method of verdox spices |
| CN107954865A (en) * | 2017-10-23 | 2018-04-24 | 江苏馨瑞香料有限公司 | A kind of preparation method of verdox |
| CN109704932A (en) * | 2017-10-25 | 2019-05-03 | 中国石油化工股份有限公司 | Catalytic hydrogenation prepares 2,6- di-t-butyl -4 methyl cyclohexanol method |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60178835A (en) * | 1984-02-25 | 1985-09-12 | Maruzen Sekiyu Kagaku Kk | Production of orthoalkylphenol |
| CN102161617A (en) * | 2010-02-23 | 2011-08-24 | 蓬莱红卫化工有限公司 | Synthesis method of 2-methyl-6-tert-butylphenol |
-
2012
- 2012-01-06 CN CN2012100031000A patent/CN103193638A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60178835A (en) * | 1984-02-25 | 1985-09-12 | Maruzen Sekiyu Kagaku Kk | Production of orthoalkylphenol |
| CN102161617A (en) * | 2010-02-23 | 2011-08-24 | 蓬莱红卫化工有限公司 | Synthesis method of 2-methyl-6-tert-butylphenol |
Non-Patent Citations (1)
| Title |
|---|
| 一轻部香料所: "乙酸对-叔丁基环己醋的合成试验", 《上海日用化工》, no. 3, 31 December 1973 (1973-12-31), pages 45 - 49 * |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104610053A (en) * | 2015-01-23 | 2015-05-13 | 中国林业科学研究院林产化学工业研究所 | Rosin derivate for soldering flux and preparation method |
| CN107840797B (en) * | 2017-10-17 | 2020-11-13 | 安徽华业香料合肥有限公司 | Production method of synthetic iridate spice |
| CN107698450A (en) * | 2017-10-17 | 2018-02-16 | 安徽华业香料合肥有限公司 | A kind of synthetic method of iris ester spices |
| CN107759447A (en) * | 2017-10-17 | 2018-03-06 | 安徽华业香料合肥有限公司 | A kind of production method of tert-butylcyclohexyl ethyl carbonate synthetic perfume |
| CN107840797A (en) * | 2017-10-17 | 2018-03-27 | 安徽华业香料合肥有限公司 | A kind of production method of iris ester synthetic perfume |
| CN107652183A (en) * | 2017-10-17 | 2018-02-02 | 安徽华业香料合肥有限公司 | A kind of synthetic method of tert-butylcyclohexyl ethyl carbonate spices |
| CN107698450B (en) * | 2017-10-17 | 2020-11-13 | 安徽华业香料合肥有限公司 | Synthetic method of irisone spice |
| CN107652183B (en) * | 2017-10-17 | 2021-01-26 | 安徽华业香料合肥有限公司 | Synthesis method of tert-butyl cyclohexyl ethyl carbonate spice |
| CN107954865A (en) * | 2017-10-23 | 2018-04-24 | 江苏馨瑞香料有限公司 | A kind of preparation method of verdox |
| CN109704932A (en) * | 2017-10-25 | 2019-05-03 | 中国石油化工股份有限公司 | Catalytic hydrogenation prepares 2,6- di-t-butyl -4 methyl cyclohexanol method |
| CN109704932B (en) * | 2017-10-25 | 2022-07-26 | 中国石油化工股份有限公司 | Method for preparing 2, 6-di-tert-butyl-4-methylcyclohexanol by catalytic hydrogenation |
| CN107827712A (en) * | 2017-10-31 | 2018-03-23 | 安徽华业香料合肥有限公司 | A kind of production method of verdox synthetic perfume |
| CN107879932A (en) * | 2017-10-31 | 2018-04-06 | 安徽华业香料合肥有限公司 | A kind of synthetic method of verdox spices |
| CN107879932B (en) * | 2017-10-31 | 2020-12-18 | 安徽华业香料合肥有限公司 | Synthesis method of o-tert-butylcyclohexyl acetate perfume |
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Application publication date: 20130710 |