CN107879932B - Synthesis method of o-tert-butylcyclohexyl acetate perfume - Google Patents
Synthesis method of o-tert-butylcyclohexyl acetate perfume Download PDFInfo
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- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/19—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds in six-membered aromatic rings
- C07C29/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds in six-membered aromatic rings in a non-condensed rings substituted with hydroxy groups
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- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom
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Abstract
The invention discloses a synthesis method of o-tert-butylcyclohexyl acetate perfume, which comprises the steps of sequentially adding petroleum ether and phenol into a three-neck glass flask, adding a titanium dioxide loaded phosphotungstic acid catalyst, dropwise adding tert-butyl alcohol at the temperature of 10-15 ℃, layering a mixed reaction liquid of o-tert-butylphenol and p-tert-butylphenol generated by the glass flask, carrying out hydrogenation reaction on an oil layer under the action of a palladium-carbon catalyst after alkali and water washing, adding acetic anhydride and p-toluenesulfonic acid into collected o-tert-butylcyclohexanol, recovering acetic acid, and carrying out alkali washing, water washing and evaporation on the oil layer to obtain the o-tert-butylcyclohexyl acetate. The method has the advantages of easily obtained raw materials, high product yield, high content of the final product of more than 98.5 percent and high content of cis-isomer of more than 85 percent, so that the final product has pure and soft fragrance and meets the requirement of flavor blending of essence and spice.
Description
Technical Field
The invention relates to a synthesis method of a perfume, and in particular relates to a synthesis method of an o-tert-butylcyclohexyl acetate perfume.
Background
O-tert-butylcyclohexyl acetate, also known as ortho-irimate, is colorless to pale yellow transparent oily liquid or solid crystal in appearance, has citrus-type fruity fragrance similar to fresh bergamot and white lemon, and woody fragrance like conifer, and has a chemical name of 2- (1, 1-dimethylethyl) cyclohexyl acetate, english name: o-Tert-butyl cyclohexyl acetate. The o-tert-butylcyclohexyl acetate is not found in nature. Molecular formula C12H22O2, CAS number: 88-41-5, can be used in various types of essences, especially in soap and washing powder essences. Relative Density of o-tert-butylcyclohexyl acetate (25 ℃ C.): 0.9390 to 0.9460, refractive index (20 ℃): 1.4490-1.4550, melting point 35 ℃, boiling point 221 ℃ (94-95 ℃/1.0 kPa), and is soluble in organic solvents such as ethanol and ethylene glycol, and insoluble in water. The o-tert-butylcyclohexyl acetate is a mixture of cis-isomer and trans-isomer, the fragrance of the cis-isomer is stronger than that of the trans-isomer, the cis-isomer proportion of the high-cis o-tert-butylcyclohexyl acetate reaches more than 90%, the o-tert-butylcyclohexyl acetate can be widely applied to various essence formulas, particularly, the o-tert-butylcyclohexyl acetate has a good application in essence with flower fragrance and costustoot fragrance, the dosage is about 10%, the dosage can be determined according to different applications, the maximum dosage can reach 30%, and the IFRA has no restriction regulation.
The o-tert-butylcyclohexyl acetate has strong flower fragrance, costustoot, apple fragrance and similar jasmine fragrance and iris-like fragrance, has very stable property and difficult discoloration, is a common synthetic perfume, is very useful in the whole modern perfume, can be used in almost all daily essence products, can even play a role in a bleaching agent, is widely applied to daily essence formulas such as perfume essence, cosmetic essence, soap essence and the like, can be well fused with the fragrances of iris ester, linalyl acetate, terpinyl acetate and ionol acetate, and comprises perfume, cream, antiperspirant, deodorant, perfumed soap, washing powder, dishwashing agent, liquid bleaching agent, fabric softener, deodorizing spray, detergent powder and the like, and is particularly useful for washing powder, perfumed soap, cologne, shampoo, skin cream and face cream.
The general production method is characterized in that phenol is used as a starting raw material, titanium dioxide loaded phosphotungstic acid or Lewis acid is used as a catalyst, isobutene gas is introduced to carry out alkylation to form o-tert-butyl phenol, Raney nickel is used for catalytic hydrogenation to form o-tert-butyl cyclohexanol, and finally acetic acid is used for esterification to obtain the o-tert-butyl cyclohexyl acetate.
Disclosure of Invention
In order to solve the general defects of the production process route of the o-tert-butylcyclohexyl acetate, the invention provides a method for synthesizing the o-tert-butylcyclohexyl acetate by taking phenol and tert-butyl alcohol as initial raw materials through hydrogenation and esterification reactions.
The synthesis method of the o-tert-butylcyclohexyl acetate spice comprises the following steps:
a) firstly adding petroleum ether into a three-mouth glass flask, then adding phenol into the glass flask, stirring and reducing the temperature to 10-15 ℃, slowly adding a titanium dioxide supported phosphotungstic acid catalyst into the glass flask, and continuously stirring for 0.5 hour after the feeding is finished;
b) dropwise adding tert-butyl alcohol into the glass flask at the temperature of between 10 and-15 ℃, controlling the dropwise adding time to be 2 hours, after the dropwise adding is finished, raising the temperature of the glass flask to between 100 and 110 ℃, continuously stirring for 2 to 4 hours, and when the content of phenol is less than or equal to 0.5 percent, cooling and finishing the reaction;
c) transferring the mixed reaction liquid of the o-tert-butylphenol and the p-tert-butylphenol generated by the glass flask into a separating funnel, standing and layering for 0.5 hour, and putting an oil layer into a beaker; adding petroleum ether into the water layer, stirring for 0.5 h, standing for layering, combining the oil layers, and placing into a beaker; adding a 5% sodium hydroxide solution into an oil layer in a beaker, stirring, carrying out alkali washing on the collected oil layer, standing and layering for 0.5 hour after stirring for 0.5 hour, adding clear water into the oil layer for washing, stirring for 0.5 hour, standing and layering for 0.5 hour, and transferring the oil layer into a hydrogenation reaction kettle;
d) putting a palladium-carbon catalyst with the palladium content of 5% by mass into a hydrogenation reaction kettle, sealing the hydrogenation reaction kettle, replacing for 4-6 times by using nitrogen, then filling the nitrogen to the pressure of 2.0Mpa, then filling hydrogen, adjusting the pressure of the hydrogenation reaction kettle to 2.0Mpa, heating to 80-150 ℃, reacting for 5-10 hours, and finishing the reaction when the content of p-tert-butylphenol is less than or equal to 0.5%;
e) filtering the generated mixed reaction liquid of the o-tert-butylcyclohexanol and the p-tert-butylcyclohexanol, and transferring liquid phase filtrate to a rotary evaporator;
f) turning on the rotary evaporator in the step e) to heat, recovering petroleum ether at the normal pressure and the kettle temperature of 60-90 ℃, turning on a vacuum pump, collecting the o-tert-butylcyclohexanol at the kettle temperature of 95-100 ℃ and under the pressure of 1000-1333 Pa, and transferring the collected o-tert-butylcyclohexanol to a four-neck flask;
g) adding acetic anhydride and p-toluenesulfonic acid into a four-neck flask, stirring and heating, controlling the reaction temperature to be 100-120 ℃, reacting for 3-5 hours, transferring the reaction liquid into a rotary evaporator, recovering acetic acid at normal pressure, and transferring the kettle bottom liquid into a beaker;
h) adding a 5% sodium hydroxide solution into a beaker, stirring, carrying out alkali washing on a collected oil layer, standing and layering for 0.5 hour after stirring for 0.5 hour, adding clear water into the oil layer for washing, standing and layering for 0.5 hour after stirring for 0.5 hour, transferring the oil layer into a rotary evaporator, starting the rotary evaporator for heating, starting a vacuum pump, and collecting o-tert-butylcyclohexyl acetate;
in the step a), the mass ratio of the petroleum ether ingredient to the phenol is 1.0: 1-5.0: 1; the mass percentage of the ingredient amount of the titanium dioxide loaded phosphotungstic acid and the total ingredient amount of the petroleum ether and the phenol is 0.5 to 5 percent; in the step b), the molar ratio of the ingredient amount of the tert-butyl alcohol to the phenol is 1.0: 1-5.0: 1; in the step c), the mass ratio of the inventory amount of petroleum ether to the water layer is 0.5: 1-2: 1, the mass ratio of the inventory amount of sodium hydroxide solution to the reaction liquid oil layer is 0.2: 1-2: 1, and the mass ratio of the inventory amount of clear water to the reaction liquid oil layer is 0.5: 1-2: 1; in the step g), the molar ratio of the ingredient amount of acetic anhydride to the ingredient amount of o-tert-butylcyclohexanol is 1.0: 1-5.0: 1, and the mass ratio of the ingredient amount of p-toluenesulfonic acid to the total ingredient amount of acetic anhydride and o-tert-butylcyclohexanol is 0.5-5%; in the step h), the mass ratio of the feeding amount of the sodium hydroxide solution to the kettle bottom liquid is 0.2: 1-2: 1, and the mass ratio of the feeding amount of the clear water to the kettle bottom liquid oil layer is 0.5: 1-2: 1.
Preferably, in the step a), the mass ratio of the petroleum ether ingredient amount to the phenol is 2.0: 1-2.5: 1; the mass percentage of the ingredient amount of the titanium dioxide loaded phosphotungstic acid and the total feeding amount of the petroleum ether and the phenol is 1 to 2 percent; in the step b), the molar ratio of the ingredient amount of the tert-butyl alcohol to the phenol is 1.0: 1-1.5: 1; in the step c), the mass ratio of the inventory amount of the petroleum ether to the water layer is 0.5: 1-1: 1, the mass ratio of the inventory amount of the sodium hydroxide solution to the reaction liquid oil layer is 0.2: 1-1: 1, and the mass ratio of the inventory amount of the clear water to the reaction liquid oil layer is 0.5: 1-1: 1; in the step g), the molar ratio of the ingredient amount of acetic anhydride to the tert-butylcyclohexanol is 1.5: 1-2.0: 1; the mass ratio of the dosage of the p-toluenesulfonic acid to the total dosage of the acetic anhydride and the o-tert-butylcyclohexanol is 1.0%: 1-2.0%; in the step h), the mass ratio of the feeding amount of the sodium hydroxide solution to the kettle bottom liquid is 0.2: 1-1: 1, and the mass ratio of the feeding amount of the clear water to the kettle bottom liquid oil layer is 0.5: 1-1: 1.
Preferably, in the step d), the material of the hydrogenation reaction kettle is stainless steel, and the design pressure is 0-5 MPa.
The synthesis method of the o-tert-butylcyclohexyl acetate spice has the advantages of easily obtained raw materials, high product yield, high final product content of more than 98.5 percent and high cis-isomer content of more than 85 percent, so that the final product has pure and soft fragrance and meets the fragrance blending requirements of essences and spices.
Detailed Description
Examples
a) 160g of petroleum ether is added into a three-neck glass flask, 75g of phenol is added into the glass flask, and a stirrer and a heat and cold exchange all-in-one machine are started to reduce the temperature of the glass flask to 15 ℃.5g of titanium dioxide supported phosphotungstic acid is added into a glass flask, and after the feeding is finished, the stirring is continued for 0.5 hour.
b) And continuously maintaining the temperature of the glass flask at 15 ℃, dropwise adding 72g of tert-butyl alcohol into the glass flask by using a dropwise adding pump, controlling the dropwise adding time to be 2 hours, raising the temperature of the kettle to 130-140 ℃ after the dropwise adding is finished, and continuously stirring for 2-4 hours. Sampling and detecting, and stopping the reaction when the content of phenol is less than or equal to 0.5%.
c) The resulting p-tert-butylphenol reaction solution was transferred to a separatory funnel and allowed to stand for 0.5 hour to separate. The oil layer was placed in a beaker. Adding 55g of petroleum ether into the water layer, stirring for 0.5 hour, standing for layering, combining oil layers, putting into a beaker, and collecting the water layer into a waste liquid collecting barrel. 90g of 5% sodium hydroxide solution is metered into a beaker of the oil layer, a stirrer is started, the collected oil layer is subjected to alkali washing, after the oil layer is stirred for 0.5 hour, the oil layer is kept stand and layered for 0.5 hour, and the alkali solution layer is concentrated into a waste liquid collecting barrel. And adding 300g of clean water into the oil layer for washing, stirring for 0.5 hour, standing for layering for 0.5 hour, and washing twice. The oil layer is transferred to a hydrogenation reaction kettle, and the water layer is concentrated to a waste liquid collecting barrel.
d) Adding 5g of palladium-carbon catalyst with the palladium content of 5% by mass into a hydrogenation reaction kettle, sealing the hydrogenation reaction kettle, replacing 4-6 times by using nitrogen, then filling the nitrogen to the pressure of 2.0Mpa, replacing 4-6 times by using hydrogen after the system pressure is stable, then filling the hydrogen, and adjusting the pressure of the hydrogenation reaction kettle to 2.0 Mpa. And after the system pressure is stable, closing the hydrogen inlet valve, heating to 90-100 ℃, after the pressure of the reaction system is balanced, opening the hydrogen valve, and keeping the reaction pressure at 2.0Mpa for 5-10 hours.
e) After 5 hours of reaction, sampling every 2 hours for chromatographic detection, and when the content of the p-tert-butylphenol is less than or equal to 0.5 percent, ending the reaction and releasing pressure. Filtering the generated reaction liquid of the tert-butyl cyclohexanol, transferring the liquid phase filtrate into a rotary evaporator, cleaning the solid phase catalyst with petroleum ether, transferring into a hydrogenation reaction kettle, and carrying out the next batch of hydrogenation reaction.
f) And e) starting the rotary evaporator to heat up, recovering petroleum ether at the normal pressure and the kettle temperature of 60-90 ℃, and concentrating and recycling the collected petroleum ether. And then starting a vacuum pump, collecting the o-tert-butylcyclohexanol at the kettle temperature of 95-100 ℃ and under the pressure condition of 1000-1333 Pa, and transferring the collected o-tert-butylcyclohexanol into a four-neck flask. The bottom liquid of the kettle is p-tert-butyl cyclohexanol, and the collected bottom liquid can be used for producing irisone.
g) Adding 120g of acetic anhydride and 3.5g of p-toluenesulfonic acid into a four-neck flask, starting a stirrer, starting a heat and heat exchange all-in-one machine for heating, controlling the reaction temperature to be 100-110 ℃, reacting for 3-5 hours, transferring the reaction liquid into a rotary evaporator, recovering acetic acid under normal pressure, and transferring the bottom liquid of the kettle into a beaker.
h) 25g of 5% sodium hydroxide solution is added into a beaker in a metered mode, a stirrer is started, the collected oil layer is subjected to alkali washing, after stirring for 0.5 hour, standing and layering are carried out for 0.5 hour, and the alkali liquid layer is collected into a waste liquid collecting barrel. And adding 60g of clear water into the oil layer for washing, stirring for 0.5 hour, standing for layering for 0.5 hour, collecting the water layer into a waste liquid collecting barrel, and washing twice. Transferring the oil layer into a rotary evaporator, starting the rotary evaporator to heat, starting a vacuum pump, and collecting the o-tert-butylcyclohexyl acetate to obtain 110.9g of the o-tert-butylcyclohexyl acetate.
The obtained product is colorless transparent liquid, has fruity and costustoot fragrance, and has purity of 99.12% by gas chromatography analysis, wherein the cis-isomer accounts for 86.8%, the detected refractive index (20 ℃) is 1.4515, and the relative density (25 ℃) is 0.9420.
The GC conditions for product detection are as follows: column HP-5 (30 m x 0.32mm x 0.25 um); detector FID, temperature 280 ℃; sample introduction: the sample injection amount is about 0.2ul, the split ratio is 1: 100, the temperature of a sample inlet is 250 ℃; carrier gas: n2, flow rate 20L/min, column front pressure 34.47 kPa; temperature of the chromatographic furnace: the linear temperature programming is carried out at the speed of 4 ℃/min from 150 ℃ to 230 ℃ and is kept for 10 min.
Titanium dioxide loaded phosphotungstic acid (H)3O40PW12 /TiO2) The preparation method of the catalyst comprises the following steps: adding water and ethanol with the same volume into a 500ml four-neck flask connected with a condenser tube, strongly stirring, heating to 70 ℃ for refluxing, dropwise adding nitric acid until the pH of the solution is =3.0, then adding phosphotungstic acid hydrolysate-ethanol solution, and uniformly stirring for later use. Adding equal volume of ethanol and n-butyl titanate into a 500ml four-neck flask, heating to 70 ℃, dropwise adding the standby solution under the condition of stirring, refluxing at 70 ℃ until the solution forms gel, drying at 100 ℃ after the gel is cooled, and roasting at 550 ℃ to prepare the titanium dioxide supported phosphotungstic acid solid acid catalyst.
Claims (3)
1. A synthesis method of o-tert-butylcyclohexyl acetate perfume comprises the following steps:
a) firstly adding petroleum ether into a three-mouth glass flask, then adding phenol into the glass flask, stirring and reducing the temperature to 10-15 ℃, slowly adding a titanium dioxide supported phosphotungstic acid catalyst into the glass flask, and continuously stirring for 0.5 hour after the feeding is finished;
b) dropwise adding tert-butyl alcohol into the glass flask at the temperature of between 10 and-15 ℃, controlling the dropwise adding time to be 2 hours, after the dropwise adding is finished, raising the temperature of the glass flask to between 100 and 110 ℃, continuously stirring for 2 to 4 hours, and when the content of phenol is less than or equal to 0.5 percent, cooling and finishing the reaction;
c) transferring the mixed reaction liquid of the o-tert-butylphenol and the p-tert-butylphenol generated by the glass flask into a separating funnel, standing and layering for 0.5 hour, and putting an oil layer into a beaker; adding petroleum ether into the water layer, stirring for 0.5 h, standing for layering, combining the oil layers, and placing into a beaker; adding a 5% sodium hydroxide solution into an oil layer in a beaker, stirring, carrying out alkali washing on the collected oil layer, standing and layering for 0.5 hour after stirring for 0.5 hour, adding clear water into the oil layer for washing, stirring for 0.5 hour, standing and layering for 0.5 hour, and transferring the oil layer into a hydrogenation reaction kettle;
d) putting a palladium-carbon catalyst with the palladium content of 5% by mass into a hydrogenation reaction kettle, sealing the hydrogenation reaction kettle, replacing for 4-6 times by using nitrogen, then filling the nitrogen to the pressure of 2.0Mpa, then filling hydrogen, adjusting the pressure of the hydrogenation reaction kettle to 2.0Mpa, heating to 80-150 ℃, reacting for 5-10 hours, and finishing the reaction when the content of p-tert-butylphenol is less than or equal to 0.5%;
e) filtering the generated mixed reaction liquid of the o-tert-butylcyclohexanol and the p-tert-butylcyclohexanol, and transferring liquid phase filtrate to a rotary evaporator;
f) turning on the rotary evaporator in the step e) to heat, recovering petroleum ether at the normal pressure and the kettle temperature of 60-90 ℃, turning on a vacuum pump, collecting the o-tert-butylcyclohexanol at the kettle temperature of 95-100 ℃ and under the pressure of 1000-1333 Pa, and transferring the collected o-tert-butylcyclohexanol to a four-neck flask;
g) adding acetic anhydride and p-toluenesulfonic acid into a four-neck flask, stirring and heating, controlling the reaction temperature to be 100-120 ℃, reacting for 3-5 hours, transferring the reaction liquid into a rotary evaporator, recovering acetic acid at normal pressure, and transferring the kettle bottom liquid into a beaker;
h) adding a 5% sodium hydroxide solution into a beaker, stirring, carrying out alkali washing on a collected oil layer, standing and layering for 0.5 hour after stirring for 0.5 hour, adding clear water into the oil layer for washing, standing and layering for 0.5 hour after stirring for 0.5 hour, transferring the oil layer into a rotary evaporator, starting the rotary evaporator for heating, starting a vacuum pump, and collecting o-tert-butylcyclohexyl acetate;
in the step a), the mass ratio of the petroleum ether ingredient to the phenol is 1.0: 1-5.0: 1; the mass percentage of the ingredient amount of the titanium dioxide loaded phosphotungstic acid and the total ingredient amount of the petroleum ether and the phenol is 0.5 to 5 percent; in the step b), the molar ratio of the ingredient amount of the tert-butyl alcohol to the phenol is 1.0: 1-5.0: 1; in the step c), the mass ratio of the inventory amount of petroleum ether to the water layer is 0.5: 1-2: 1, the mass ratio of the inventory amount of sodium hydroxide solution to the reaction liquid oil layer is 0.2: 1-2: 1, and the mass ratio of the inventory amount of clear water to the reaction liquid oil layer is 0.5: 1-2: 1; in the step g), the molar ratio of the ingredient amount of acetic anhydride to the ingredient amount of o-tert-butylcyclohexanol is 1.0: 1-5.0: 1, and the mass ratio of the ingredient amount of p-toluenesulfonic acid to the total ingredient amount of acetic anhydride and o-tert-butylcyclohexanol is 0.5-5%; in the step h), the mass ratio of the feeding amount of the sodium hydroxide solution to the kettle bottom liquid is 0.2: 1-2: 1, and the mass ratio of the feeding amount of the clear water to the kettle bottom liquid oil layer is 0.5: 1-2: 1.
2. The method for synthesizing o-tert-butylcyclohexyl acetate perfume according to claim 1, wherein the method comprises the following steps: in the step a), the mass ratio of the petroleum ether ingredient to the phenol is 2.0: 1-2.5: 1; the mass percentage of the ingredient amount of the titanium dioxide loaded phosphotungstic acid and the total feeding amount of the petroleum ether and the phenol is 1 to 2 percent; in the step b), the molar ratio of the ingredient amount of the tert-butyl alcohol to the phenol is 1.0: 1-1.5: 1; in the step c), the mass ratio of the inventory amount of the petroleum ether to the water layer is 0.5: 1-1: 1, the mass ratio of the inventory amount of the sodium hydroxide solution to the reaction liquid oil layer is 0.2: 1-1: 1, and the mass ratio of the inventory amount of the clear water to the reaction liquid oil layer is 0.5: 1-1: 1; in the step g), the molar ratio of the ingredient amount of acetic anhydride to the tert-butylcyclohexanol is 1.5: 1-2.0: 1; the mass ratio of the dosage of the p-toluenesulfonic acid to the total dosage of the acetic anhydride and the o-tert-butylcyclohexanol is 1.0%: 1-2.0%; in the step h), the mass ratio of the feeding amount of the sodium hydroxide solution to the kettle bottom liquid is 0.2: 1-1: 1, and the mass ratio of the feeding amount of the clear water to the kettle bottom liquid oil layer is 0.5: 1-1: 1.
3. The method for synthesizing o-tert-butylcyclohexyl acetate perfume according to claim 1 or 2, characterized by comprising the following steps: in the step d), the hydrogenation reaction kettle is made of stainless steel, and the design pressure is 0-5 MPa.
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JP2003055312A (en) * | 2001-08-10 | 2003-02-26 | Kao Corp | Optically active ester |
CN101830798A (en) * | 2010-05-26 | 2010-09-15 | 杭州友邦香料香精有限公司 | Preparation method of high-cis vertenex |
CN103193638A (en) * | 2012-01-06 | 2013-07-10 | 南昌洋浦天然香料香精有限公司 | Synthetic method of perfume o-tert-butylcyclohexyl acetate |
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JP2003055312A (en) * | 2001-08-10 | 2003-02-26 | Kao Corp | Optically active ester |
CN101830798A (en) * | 2010-05-26 | 2010-09-15 | 杭州友邦香料香精有限公司 | Preparation method of high-cis vertenex |
CN103193638A (en) * | 2012-01-06 | 2013-07-10 | 南昌洋浦天然香料香精有限公司 | Synthetic method of perfume o-tert-butylcyclohexyl acetate |
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