CN102826977A - Synthesis method and application of 7-methoxy-3,7-dimethyloctyl aldehyde - Google Patents
Synthesis method and application of 7-methoxy-3,7-dimethyloctyl aldehyde Download PDFInfo
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- CN102826977A CN102826977A CN2012103601665A CN201210360166A CN102826977A CN 102826977 A CN102826977 A CN 102826977A CN 2012103601665 A CN2012103601665 A CN 2012103601665A CN 201210360166 A CN201210360166 A CN 201210360166A CN 102826977 A CN102826977 A CN 102826977A
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- octanal
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- deionized water
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- -1 7-methoxy-3,7-dimethyloctyl aldehyde Chemical class 0.000 title claims abstract description 8
- 238000001308 synthesis method Methods 0.000 title abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000008367 deionised water Substances 0.000 claims abstract description 25
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 25
- 239000002253 acid Substances 0.000 claims abstract description 24
- 239000003054 catalyst Substances 0.000 claims abstract description 24
- 239000002131 composite material Substances 0.000 claims abstract description 24
- 239000007787 solid Substances 0.000 claims abstract description 24
- 150000002081 enamines Chemical class 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000002808 molecular sieve Substances 0.000 claims abstract description 13
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000001412 amines Chemical class 0.000 claims abstract description 10
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229930003633 citronellal Natural products 0.000 claims abstract description 10
- 235000000983 citronellal Nutrition 0.000 claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 238000005406 washing Methods 0.000 claims abstract description 5
- 244000068485 Convallaria majalis Species 0.000 claims abstract description 3
- 235000009046 Convallaria majalis Nutrition 0.000 claims abstract description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000010410 layer Substances 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 8
- 238000000967 suction filtration Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- 235000019605 sweet taste sensations Nutrition 0.000 claims description 5
- 235000005979 Citrus limon Nutrition 0.000 claims description 4
- 244000131522 Citrus pyriformis Species 0.000 claims description 4
- 208000005156 Dehydration Diseases 0.000 claims description 4
- 241000234435 Lilium Species 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- 238000013019 agitation Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910052681 coesite Inorganic materials 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 229910052906 cristobalite Inorganic materials 0.000 claims description 4
- 230000018044 dehydration Effects 0.000 claims description 4
- 238000006297 dehydration reaction Methods 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 230000008030 elimination Effects 0.000 claims description 4
- 238000003379 elimination reaction Methods 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- 239000012065 filter cake Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 235000012239 silicon dioxide Nutrition 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 229910052682 stishovite Inorganic materials 0.000 claims description 4
- 229910052905 tridymite Inorganic materials 0.000 claims description 4
- 239000003205 fragrance Substances 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 239000002537 cosmetic Substances 0.000 abstract description 2
- 238000006386 neutralization reaction Methods 0.000 abstract description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 238000006266 etherification reaction Methods 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 238000003828 vacuum filtration Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 28
- 239000002304 perfume Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000005303 weighing Methods 0.000 description 4
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a synthesis method and application of 7-methoxy-3,7-dimethyloctyl aldehyde. The synthesis method comprises the following steps: synthesis of intermediate enamine I: reacting a dimethyl amine deionized water solution with a certain concentration, a 4A molecular sieve and 3,7-dimethyl-6-octenal, carrying out vacuum filtration, and stratifying; and synthesis of 7-methoxy-3,7-dimethyloctyl aldehyde: reacting methanol, strong-acid solid composite catalyst, I, cyclohexane, potassium hydroxide and sodium carbonate, washing and stratifying. The low-price 3,7-dimethyl-6-octenal is used as the raw material, amines are utilized to implement carbonyl protection to convert the 3,7-dimethyl-6-octenal into enamine compounds, and the strong-acid solid composite catalyst is utilized to catalyze the etherification between the C=C bond and the methanol and implement neutralization and amine removal, thereby obtaining the target product. The invention has the advantages of simple production technique, mild operating conditions, low requirements for production equipment, cheap and accessible raw materials and high yield. The 7-methoxy-3,7-dimethyloctyl aldehyde has fresh subtle fragrance as well as fragrance of leaves, Convallaria majalis flowers and the like, and can be used in cosmetic essence.
Description
Technical field
The invention belongs to the foodstuff additive field, relate to a kind of synthetic perfume, specifically a kind of 7-methoxyl group-3, the compound method of 7-dimethyl-octanal and obtain the application of product.
Background technology
Along with development and national economy, people's lives progressively have and simply having adequate food and clothingly turn to fairly well-offly, and for the development of perfume industry product provides a wide big market, especially natural perfume enjoys favor.But, on kind quantity and quality product, receive certain influence because natural animal-plant spices often receives factors such as restriction and the processing of natural condition.The innovation of essence and the raising of quality also more and more rely on new synthetic perfume kind.Because synthetic perfume does not receive the restriction of natural condition, steady quality, the big I of industrial scale is arranged by people oneself, and the price of product is also than natural sources considerably cheaper.Therefore, development and the new synthetic perfume of developing development also seem more and more important.Particularly along with modern science research and analysis state of the art improves constantly separable and main fragrant composition and the structure thereof of analysis in the natural perfume, thereby develop through chemical synthesis process.Both the natural perfume deficiency can be solved, Financial cost can be reduced again.
7-methoxyl group-3,7-dimethyl-octanal are to have fresh delicate fragrance, and fragrance such as Ye Xiang and flores convallariae can be used in the makeup.In addition, it not only is widely used in the daily use chemicals processing industry, also is simultaneously one of important intermediate of synthetic neotonin agricultural chemicals alkene worm propyl ester.
Summary of the invention
The purpose of this invention is to provide a kind of 7-methoxyl group-3; The compound method of 7-dimethyl-octanal and obtain the application of product; The present invention has adopted low price, obtain easily 3,7-dimethyl--6-octenal is a raw material; Implement carbonyl-protection with amine and make it to become olefinic amine compound, strong acid solid composite catalyst carbon carbon two strong and methyl alcohol carry out etherificate and neutralization and take off amine and obtain title product.This synthetic route production technique is simple, and operational condition is gentle, and production unit requires low, and raw materials cost is lower and be easy to get, and yield is higher.
The objective of the invention is to realize through following technical scheme:
A kind of 7-methoxyl group-3,7-dimethyl-octanal compound method, it is characterized in that: this compound method comprises the midbody enamine
ISynthetic and 7-methoxyl group-3,7-dimethyl-octanal synthetic, specific as follows:
1) midbody enamine
ISynthetic,
In bottle, dropping into concentration is the n n dimetylaniline deionized water solution of 25%-40%, and adding quality is the dewatering agent four A molecular sieves of n n dimetylaniline deionized water solution 0.1%-1%, and temperature of reaction is-15 ~-5 ℃; In 1-5 hour, being added drop-wise to concentration under the violent stirring is 3 of 75%-95%, and 7-dimethyl--6-octenal drips and finishes in the n n dimetylaniline deionized water solution; After 10-25 ℃ of continuation reaction finished reaction in 1-10 hour; Carry out suction filtration, filtrating is poured in the separating funnel standing demix into; Tell lower aqueous layer, oil reservoir is told lower aqueous layer once more with the washing of saturated common salt deionized water thorough mixing; Adding quality in the oil reservoir is the four A molecular sieve dehydrations of the 1%-10% of oil reservoir, and the oil phase of sloughing moisture gets enamine solution through filtering
I, content is 90%-95%, yield is 85%-95%; N n dimetylaniline and 3,7-dimethyl--6-octenal mol ratio is 1:5-5:1.
2) 7-methoxyl group-3,7-dimethyl-octanal is synthetic
In bottle, add concentration and be 99.5% methyl alcohol, stir down with cryosel bathe be cooled to-5 ~-15 ℃ for use; Get the strong acid type solid composite catalyst, it is slowly added in the methyl alcohol, controlled temperature is not more than-2 ℃; Finish, under agitation add enamine
I,0.5-1 hour dropping time, and control reaction temperature is not higher than-2 ℃; Drip and finish, remove ice bath, make temperature rise to 15-20 ℃, stirring reaction 1-5 hour; Above-mentioned solution is added normal hexane dilution 105-50% hexane solution; During degree of cooling to-2 ~-8 ℃ of left and right sides, dropping concentration is that the Pottasium Hydroxide deionized water solution of 20%-40% takes off amine, and holding temperature is no more than 15 ℃; When solution pH value during, use the saturated sodium bicarbonate deionized water solution instead and regulate PH to 5-7 to 3-5; With in the solution of becoming reconciled carry out suction filtration, filter cake washs with normal hexane, incorporates filtrating into, the filtrating standing demix; Water layer merges to organic layer and adds the four A molecular sieve standing and drying that quality is the 1%-10% of feed liquid with n-hexane extraction 3-5 time, boils off the solvent normal hexane behind the elimination sal epsom; Raffinate rectification under vacuum under nitrogen protection, vacuum tightness under the 400-800Pa condition, interior temperature 100-150 ℃; Temperature is 100-106 ℃ and collects colourless cut, obtains 7-methoxyl group-3,7-dimethyl-octanal; Yield is 85%-95%, and content is 90%-95%; Wherein the mol ratio of methyl alcohol and strong acid type solid composite catalyst is 1:3-3:1, and the mol ratio of strong acid solid composite catalyst and enamine is 1:5-5:1.
Among the present invention, the strong acid solid composite catalyst is a SiO2/ZrO2 strong acid solid composite catalyst.
The 7-methoxyl group-3 that a kind of above-mentioned compound method obtains, the application of 7-dimethyl-octanal in daily chemical essence and the production of sweet taste essence.Be used for the fragrant and fragrant daily use chemicals of leaf of the lily of the valley.With the 7-methoxyl group-3 of gained, 7-dimethyl-octanal is applied to rose as raw material, and lemon is in the lily daily use chemicals.
The present invention mainly contains two-step reaction and forms, and the first step is the midbody enamine
ISynthetic, second step was a 7-methoxyl group-3,7-dimethyl-octanal synthetic.The 7-methoxyl group-3 that obtains, 7-dimethyl-octanal is applied to rose as raw material, and lemon is in daily use chemicals such as lily and the sweet taste essence.
Synthetic route of the present invention is following:
The present invention has adopted low price; Obtain easily 3; 7-dimethyl--6-octenal is a raw material, makes it to become olefinic amine compound with amine enforcement carbonyl-protection, and two being good for methyl alcohol of strong acid solid composite catalyst catalyzed carbon carbon carries out etherificate and neutralize taking off the operational path that amine obtains title product.It is simple that this synthetic route has production technique, and operational condition is gentle, and production unit requires low, and raw materials cost is lower and be easy to get, and yield is than advantages such as height.
Embodiment
Embodiment 1
A kind of 7-methoxyl group-3,7-dimethyl-octanal compound method, reaction in two steps, the first step is the midbody enamine
ISynthetic, second step was a 7-methoxyl group-3,7-dimethyl-octanal synthetic.
It at first is the first step: the midbody enamine
ISynthetic, in bottle, drop into concentration and be 30% n n dimetylaniline deionized water solution, add dewatering agent four A molecular sieves (its amount is 1% of n n dimetylaniline deionized water solution amount); Temperature of reaction is-5 ℃, in 3 hours, drip concentration under the violent stirring and be 80% 3,7-dimethyl--6-octenal is in the n n dimetylaniline deionized water solution; Drip and finish, after 20 ℃ of continuation reactions finished reaction in 8 hours, carry out suction filtration; Filtrating is poured in the separatory leak standing demix into.Tell lower aqueous layer, oil reservoir is told lower aqueous layer once more with the washing of saturated common salt deionized water thorough mixing.Add four an amount of A molecular sieve dehydrations (its amount is 5% of oil reservoir) in the oil reservoir, the oil phase of sloughing moisture is through filtering, weigh the limpid enamine solution of little Huang
I, content is 93%, yield is 90%.N n dimetylaniline and 3,7-dimethyl--6-octenal mol ratio is 1:3.
Second step was: 7-methoxyl group-3,7-dimethyl-octanal is synthetic, in bottle, adds concentration and be 99.5% methyl alcohol, stir down with cryosel bathe be cooled to-10 ℃ for use.Take by weighing the strong acid solid composite catalyst, it is slowly added in the methyl alcohol, controlled temperature is not more than-2 ℃.Finish, under agitation add enamine
I,1 hour dropping time, and control reaction temperature is not higher than-2 ℃.Drip and finish, remove ice bath, make temperature rise to 20 ℃, stirring reaction 3 hours.Above-mentioned solution is added an amount of normal hexane dilution.Degree of cooling drips concentration and is 30% Pottasium Hydroxide deionized water solution and take off amine when-5 ℃ of left and right sides, and holding temperature is no more than 15 ℃.When solution pH value to 3, this is regulated about PH to 6 with the saturated sodium bicarbonate deionized water solution.With in the solution of becoming reconciled carry out suction filtration, filter cake washs with normal hexane, incorporates filtrating into; Filtrating standing demix, water layer be with n-hexane extraction 3-5 time, merges to organic layer and add 4a molecular sieve standing and drying (be feed liquid 8%); Boil off the solvent normal hexane behind the elimination sal epsom, colourless cut is collected in raffinate rectification under vacuum under nitrogen protection under 100-106 ℃/400-800Pa condition; Obtain 7-methoxyl group-3,7-dimethyl-octanal.The yield of weighing is 90%, and content is 93%.Methyl alcohol wherein, the mol ratio of strong acid solid composite catalyst is 1:2, the mol ratio of strong acid solid composite catalyst and enamine is 1:3.The strong acid solid composite catalyst is a SiO2/ZrO2 strong acid solid composite catalyst.
Embodiment 2
A kind of 7-methoxyl group-3,7-dimethyl-octanal compound method, concrete steps are following:
It at first is the first step: the midbody enamine
ISynthetic, in bottle, drop into concentration and be 35% n n dimetylaniline deionized water solution, adds an amount of dewatering agent four A molecular sieves (its amount be n n dimetylaniline deionized water solution 1%); Temperature of reaction is-10 ℃, in 4 hours, drip concentration under the violent stirring and be 90% 3,7-dimethyl--6-octenal is in the n n dimetylaniline deionized water solution; Drip and finish, after 25 ℃ of continuation reactions finished reaction in 2 hours, carry out suction filtration; Filtrating is poured in the separatory leak standing demix into.Tell lower aqueous layer, oil reservoir is told lower aqueous layer once more with the washing of saturated common salt deionized water thorough mixing.Add four an amount of A molecular sieve dehydrations (its amount is 6% of oil reservoir) in the oil reservoir, the oil phase of sloughing moisture is through filtering, weigh the limpid enamine solution of little Huang
I, content is 90%, yield is 90%.N n dimetylaniline and 3,7-dimethyl--6-octenal mol ratio is 1:1.
Second step was: 7-methoxyl group-3,7-dimethyl-octanal is synthetic, in bottle, adds concentration and be 99.5% methyl alcohol, stir down with cryosel bathe be cooled to-15 ℃ for use.Take by weighing the strong acid solid composite catalyst, it slowly is added dropwise in the methyl alcohol, controlled temperature is not more than-2 ℃.Finish, under agitation add enamine
I,1 hour dropping time, and control reaction temperature is not higher than-2 ℃.Drip and finish, remove ice bath, make temperature rise to 20 ℃, stirring reaction 1 hour.Above-mentioned solution is added an amount of normal hexane dilution.Degree of cooling drips concentration and is 20% Pottasium Hydroxide deionized water solution and take off amine when-4 ℃ of left and right sides, and holding temperature is no more than 15 ℃.When solution pH value to 4, this is regulated about PH to 7 with the saturated sodium bicarbonate deionized water solution.With in the solution of becoming reconciled carry out suction filtration, filter cake washs with normal hexane, incorporates filtrating into; Filtrating standing demix, water layer be with n-hexane extraction 3-5 time, merges to organic layer and add 4a molecular sieve standing and drying (be feed liquid 5%); Boil off the solvent normal hexane behind the elimination sal epsom, colourless cut is collected in raffinate rectification under vacuum under nitrogen protection under 100-106 ℃/400-800Pa condition; Obtain 7-methoxyl group-3,7-dimethyl-octanal.The yield of weighing is 95%, and content is 90%.Methyl alcohol wherein, the mol ratio of strong acid solid composite catalyst is 1:1, the mol ratio of strong acid solid composite catalyst and enamine is 1:1.The strong acid solid composite catalyst is a SiO2/ZrO2 strong acid solid composite catalyst.
The 7-methoxyl group-3 that above-mentioned two steps obtain, 7-dimethyl-octanal has fresh delicate fragrance, and fragrance such as Ye Xiang and flores convallariae can be used for being applied to rose as raw material in the cosmetic essence, and lemon is in the daily use chemicals such as lily.
Claims (5)
1. 7-methoxyl group-3,7-dimethyl-octanal compound method, it is characterized in that: this compound method comprises the midbody enamine
ISynthetic and 7-methoxyl group-3,7-dimethyl-octanal synthetic, specific as follows:
1) midbody enamine
ISynthetic,
In bottle, dropping into concentration is the n n dimetylaniline deionized water solution of 25%-40%, and adding quality is the dewatering agent four A molecular sieves of n n dimetylaniline deionized water solution 0.1%-1%, and temperature of reaction is-15 ~-5 ℃; In 1-5 hour, being added drop-wise to concentration under the violent stirring is 3 of 75%-95%, and 7-dimethyl--6-octenal drips and finishes in the n n dimetylaniline deionized water solution; After 10-25 ℃ of continuation reaction finished reaction in 1-10 hour; Carry out suction filtration, filtrating is poured in the separating funnel standing demix into; Tell lower aqueous layer, oil reservoir is told lower aqueous layer once more with the washing of saturated common salt deionized water thorough mixing; Adding quality in the oil reservoir is the four A molecular sieve dehydrations of the 1%-10% of oil reservoir, and the oil phase of sloughing moisture gets enamine solution through filtering
I, content is 90%-95%, yield is 85%-95%; N n dimetylaniline and 3,7-dimethyl--6-octenal mol ratio is 1:5-5:1;
2) 7-methoxyl group-3,7-dimethyl-octanal is synthetic
In bottle, add concentration and be 99.5% methyl alcohol, stir down with cryosel bathe be cooled to-5 ~-15 ℃ for use; Get the strong acid type solid composite catalyst, it is slowly added in the methyl alcohol, controlled temperature is not more than-2 ℃; Finish, under agitation add enamine
I,0.5-1 hour dropping time, and control reaction temperature is not higher than-2 ℃; Drip and finish, remove ice bath, make temperature rise to 15-20 ℃, stirring reaction 1-5 hour; Above-mentioned solution is added normal hexane be diluted to the 10%-50% hexane solution; During degree of cooling to-2 ~-8 ℃ of left and right sides, dropping concentration is that the Pottasium Hydroxide deionized water solution of 20%-40% takes off amine, and holding temperature is no more than 15 ℃; When solution pH value during, use the saturated sodium bicarbonate deionized water solution instead and regulate PH to 5-7 to 3-5; With in the solution of becoming reconciled carry out suction filtration, filter cake washs with normal hexane, incorporates filtrating into, the filtrating standing demix; Water layer merges to organic layer and adds the four A molecular sieve standing and drying that quality is the 1%-10% of feed liquid with n-hexane extraction 3-5 time, boils off the solvent normal hexane behind the elimination sal epsom; Raffinate rectification under vacuum under nitrogen protection, vacuum tightness under the 400-800Pa condition, interior temperature 100-150 ℃; Temperature is 100-106 ℃ and collects colourless cut, obtains 7-methoxyl group-3,7-dimethyl-octanal; Yield is 85%-95%, and content is 90%-95%; Wherein the mol ratio of methyl alcohol and strong acid type solid composite catalyst is 1:3-3:1, and the mol ratio of strong acid solid composite catalyst and enamine is 1:5-5:1.
2. 7-methoxyl group-3 according to claim 1,7-dimethyl-octanal compound method is characterized in that: step 2) in, the strong acid solid composite catalyst is a SiO2/ZrO2 strong acid solid composite catalyst.
3. 7-methoxyl group-3 that the described compound method of claim 1 obtains, the application of 7-dimethyl-octanal in daily chemical essence and sweet taste essence are produced.
4. 7-methoxyl group-3 according to claim 4, the application of 7-dimethyl-octanal in daily chemical essence and the production of sweet taste essence is characterized in that: be used for the fragrant and fragrant daily use chemicals of leaf of the lily of the valley.
5. 7-methoxyl group-3 according to claim 4, the application of 7-dimethyl-octanal in daily chemical essence and the production of sweet taste essence, it is characterized in that: with the 7-methoxyl group-3 of gained, 7-dimethyl-octanal is applied to rose as raw material, and lemon is in the lily daily use chemicals.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107032971A (en) * | 2017-04-27 | 2017-08-11 | 上海应用技术大学 | A kind of preparation method of the octenal of 3,7 dimethyl, 6 carbonyl 2 |
| CN107536004A (en) * | 2016-06-28 | 2018-01-05 | 长谷川香料株式会社 | Low-fat food flavor improving agent |
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| US3978135A (en) * | 1971-12-21 | 1976-08-31 | Rhone-Poulenc S.A. | Preparation of ethers from citronellal or homologues thereof |
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| US3978135A (en) * | 1971-12-21 | 1976-08-31 | Rhone-Poulenc S.A. | Preparation of ethers from citronellal or homologues thereof |
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| 孙揭阳: "甲氧基香茅醛合成工艺研究", 《化学世界》, no. 3, 25 March 2009 (2009-03-25), pages 167 - 170 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107536004A (en) * | 2016-06-28 | 2018-01-05 | 长谷川香料株式会社 | Low-fat food flavor improving agent |
| CN107032971A (en) * | 2017-04-27 | 2017-08-11 | 上海应用技术大学 | A kind of preparation method of the octenal of 3,7 dimethyl, 6 carbonyl 2 |
| CN107032971B (en) * | 2017-04-27 | 2020-05-12 | 上海应用技术大学 | A kind of preparation method of 3,7-dimethyl-6-carbonyl-2-octenal |
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