NOVEL ALICYCLIC ALCOHOL

[Formula (1) represented by novel alicyclic alcohol]

Formula (1) acid and alcohol are novel alicyclic of the present invention is represented by. Wherein, formula (1) represented by structure is appropriate, cyclohexane ring of the sheath according to substituted 1, 4 position, transisomer can be present but, the present invention which include the administration include cis isomer structure of alicyclic alcohol, transisomer a phenyl-based alkoxysilane compound in by itself one of, in addition can be used as mixture. Said formula (1) acid and alcohol are novel alicyclic represented by, and non-greasy to the suck-in an anti-feeling [...] , green-like of fragrance provided with at, either alone or in the combination with component soap, shampoo, rinse, detergent, cosmetic, spray product, aromatic, perfume, bathing number vice-direction such as, use can be made of, as material.

[Perfume composition]

Comprises perfume compositions of the present invention, in the DC offset of the other typically perfume having effusion component or an, to perfume is a desirable constituent combination of, formula (1) represented by novel alicyclic alcohol is dehydrating are performed for the is prepared. Blends the amount, type aromatics combination, a fragrance intended to, the types of fragrance strength to accomplish different but according to, adding 0.01-90 mass % during perfume combination it is preferred to set a, 0.1-50 mass % and it is more preferably added.

Alcohol and novel alicyclic of the present invention can be are used in combination with fragrance ingredient includes, hydrocarbons, alcohols, phenol, esters, polycarbonates, aldehydes, ketones, polyacetal current, ethers, nitrile current, carboxylic acid current, lactone such as natural essential oil or natural extract, synthetic-soluble macromolecules can be mentionned.

[Novel alicyclic of the alcohol manufacturing method]

The manufacturing method of the present invention novel alicyclic alcohol compound of

(A) formula (2) using Hf mono compound represented by (after, also referred to as HF) fluoride acid reacting carbon monoxide in the presence (formula (3)) is reformed to obtain a (hereinafter, "a carbonylation process" in steps also a),

(B) type (4) isomers by fluoride with acid being represented by a process (hereinafter, "isomerization process" in steps also a),

(C) then alcohol and reacting the formula (5) cyclohexane represented by which comprises the step of obtaining an carbonyl compounds (hereinafter, "the process" in steps also a), and

(D) for reducing carbonyl compounds cyclohexane obtained the formula (1) represented by which comprises the step of obtaining an alicyclic alcohol (hereinafter, "carbonyl functional reduction process" in steps also a) includes.

<(a) 카르보닐화 공정 >

Mono carbonylation of compound HF reaction is under pressure of carbon monoxide in the presence of the embodiment. Thus type (3) alicyclic represented by water as a by-product in a variety of carbonyl compounds (including other isomers) and. a light.

[Formula 3]

[Mono compound]

General formula (2) mono compound represented by, for example compound dienes corresponding part by a hydrogenation catalyst to hydrogenate the olefinically can be prepared from hydrogenated to..

Synthetic mono the compound, removal of, such as on a catalyst due to the mis embodiment purification by or distilled after but are preferably used in the form of, removal of, typically of the catalyst is not good, an error state, of mono compound employed in the reaction process, are separated from each other and of solvents, reaction as a by-product-product hydrogenated entire by the decomposer separated connecting the main body to the controller without embodiment the carbonylation reactions has.

(Synthesis of compound n mono)

Mono diene compounds used in the synthesis of compound (hereinafter, "diene compounds" that is used in steps also) include, with pentane being thin-film layer has a single ring 6 won, said 6 won ring of the framework of the canopy shelter 1, 4 position with methyl each having hydrocarbon groups profile of, 2 in the molecule is a compound having two double bonds is preferably used. Specifically, alicyclic hydrocarbons, such as is the exemplary polyalcoxylated terpenic hydrocarbon, preferably limonene, α-terpinene, β-terpinene, γ-terpinene, at this sound[...] , [...] -α, β- [...] , [...] , [...] terpene, and is exemplified [...] , more preferably limonene, α-terpinene, γ-terpinene, [...] -α, [...] terpene, [...] is exemplary, more preferably is exemplary [...] in terms of availability. [...] orange, grapefruit or lemon shell extracted from natural essential oil in contains in, steam distillation is easily by 98% purity are obtained. Furthermore, the other uses the limonene industrially production device is an inexpensive way by giving an appearance as..

Diene hydrogenation catalyst a, used for the hydrogenation of unsaturated bond in a generally but is not particularly limited in if catalyst, number 8-11 group metal selected from periodic table 1 species preferably a catalyst containing at least.

Specifically, iron, cobalt, nickel, copper, ruthenium, rhodium, palladium, the, osmium, iridium, platinum and gold at least selected from containing the species to a catalyst that is 1.

The hydrogenation catalyst comprises an a solid catalyst uniform; even based catalyst, in terms of the separation of the reactant solid catalyst being preferred..

Solid catalyst non--supported metal catalyst such as catalyst carrying metal or is the exemplary, non-supported metal catalyst (1) (Raney) Raney nickel, Raney cobalt, Raney such as copper of Raney catalyst, (2) platinum, palladium, rhodium, ruthenium such as oxides or colloidal catalyst being preferred..

Carrying metal catalyst, magnesia, zirconia, ceria, diatomite, activated carbon, alumina, silica, zeolite, titania on a carrier such as iron, cobalt, nickel, copper, ruthenium, rhodium, palladium, the, osmium, iridium, platinum, gold during 1 containing at least one is the exemplary a or mixing the filler, copper-chromium catalyst (Adkins catalyst), copper-zinc catalyst, copper-like iron the support and then drying and the copper catalyst a supported copper catalyst, Pt/C or Pt/alumina such as supported platinum catalyst, such as/alumina Pd or Pd/C containing palladium catalyst, ruthenium catalyst containing Ru/C or Ru/alumina such as, or Rh/C or Rh/alumina such as. is preferable rhodium catalyst containing. At, in activity and selectivity reaction using catalysts containing copper with, it is more preferably.

Furthermore, copper based catalysts structure, diene reaction a solvent such as heptane before 140-200 °C, 1-3 1-3 MPa hydrogen pressure in the reaction several steps of time the objective compound. activity and selectivity.

Hydrogenation catalyst is used in an amount of to accomplish different but of the catalyst, a compound in which a a diene-raw material 0.001-100 mass %, preferably 0.01-30 mass %, more preferably 0.1-20 mass %. suitable.

Hydrogen pressure of the atmospheric pressure, even pressurized embodiment although it is possible, generally 0.1-4.0 MPa and the shaft transfers the, preferably 0.1-3.0 MPa, more preferably is in the range of 0.1-2.0 MPa.

A solventless hydrogenation being conducted in a hydrogenation reactor embodiment although it is possible in part may be involve the use of solvents and, and high purity, formic, acetic acid ([...]) acid such as, benzene, o-dichloro benzene, toluene, xylene strain of an aromatic compounds and, hexane, heptane, hydrocarbons such as cyclohexane, methanol, ethanol, isopropyl alcohol, t butyl alcohol, ethylene glycol, diethylene ethylene glycol, alcohols, dioxane, for ease of application, [...] , such as ethers or mixtures thereof being a D writing, :.

When using a hydrogenation being conducted in a hydrogenation reactor the amount of evaporating a solvent from, a diene-raw material usually a compound in which a range of 0.1-30 mass back (mass) using although it is possible, preferably 0.2-20 may bail mass.

In conventional the reaction temperature of hydrogenation being conducted in a hydrogenation reactor -90 °C -200 °C embodiment although it is possible, preferably 20 °C -150 °C, more preferably is 20 °C -100 °C.

Hydrogenation being conducted in a hydrogenation reactor of format is acceptable and, possible reaction hydrogenation contact that are not particularly limited and, of the commonly used publicly known preferably of. For example, contact the fluidized fluid catalyst hydrogenation the reaction takes place in the a reactor, fluid immobilised charging catalyst by supplying contact hydrogenation reaction such as fixed-bed reactor performing.

[Carbon monoxide]

Carbon monoxide used in a carbonylation process of the present invention, is included inert gas such as methane or nitrogen may be but, carbon monoxide partial pressure as 0.5-5 MPa, preferably the embodiment in a range of 1-3 MPa. The voltage is a carbon monoxide 0.5 MPa than high, carbonylation reaction is sufficiently running on the, side reactions such as polymerization fire germ or without concurrence , alicyclic wavefronts are at a high yield by can cause carbonyl compounds. Furthermore, the carbon monoxide partial pressure is 5 MPa hereinafter preferably in terms of load equipment.

[Hydrogen fluoride]

A carbonylation process used in the HF, and reaction solvent, which catalyst, to are provided to controlling strip tension while, substantially anhydrous for use. HF is used in an amount of, a compound in which a n mono raw material 4-15 molar times, preferably 6-10 molar is an. HF and wherein the molar ratio of the molar times larger than the surface 4, the procedure passes on efficient carbonylation reaction, the content of nonionic surfactant is 0.01 polymerization fire germ or is capable of inhibiting any, alicyclic wavefronts are at a high yield by can cause carbonyl compounds. In addition in terms of raw material cost and productivity of 15 molar times preferably use of HF hereinafter.

[Reaction conditions]

Special form of carbonylation reaction and free from are restrictions, batch, glutamate dehydrogenase, preferably even continuous such as a method.

Carbonylation reaction of -50 °C -30 °C the reaction temperature, preferably -40 °C -0 °C, in particular preferably in a range of -30--25 °C the embodiment. Carbonylation reaction of reaction temperature is 30 °C hereinafter, .good selectivity is in particular -25 °C hereinafter. Furthermore, -50 °C in terms used in manufacturing preferably conducted at or above.

<(b) 이성화 공정 >

Type (3) type from fluoride acid represented by (4) with acid being represented by when by isomerization of to fluoride, after the separation of the senses whether fluoride acid, again isomerization reaction in the presence of a catalyst, HF embodiment although it is possible, generally without separation of acidic fluoride, carbonyl in the obtained reaction liquid reactions such as isomerization to a speed of n times. Carbon monoxide-supplying the atmospheric pressure reactions such as isomerization embodiment a fine under pressure. The, carbon monoxide partial pressure the 0.1-2 MPa, preferably the embodiment in a range of 0.1-1 MPa. The voltage is a carbon monoxide 2 MPa than high, adhesive is sufficiently reactions such as isomerization, the partial pressure carbon monoxide in terms yield preferably lower. Furthermore, a network monitor measures a transmission 0.1 MPa the voltage is a carbon monoxide, since the acid fluoride includes a plurality of corpuscles electrically movable occurs preferably 0.1 MPa or more.

Furthermore, the reaction temperature in process for isomerization, reaction rates, inhibitors of disintegrating the fluoride acid, and other isomers inhibitors of for isomerization of considering the or the like, 0-50 °C range, preferably 10-30 °C is from range.

[Formula 4]

<(c) 에스테르화 공정 >

Reactions such as isomerization reaction solution fluoride acid generated at the, 1-4 carbon atoms, to react it with alcohol alicyclic ester compound 1/10 time as large as that of. Reaction in terms of corrosive device, at this time, predetermined amount of reaction solution at a fluoride acid adding an alcohol to preferably a method.

Furthermore, reactions such as isomerization reaction solution fluoride acid generated at the, instead the process said, after removing the excessive (I) for the distillative HF, distillation such as conventional method by purifying and, acid fluoride directly and used as raw material for reduction process carbonyl functional is proceeded then may, after removing the excessive (II) for the distillative HF, the corresponding hydrolysis, obtains and makes a carboxylic acid, said distillation a carboxylic acid such as conventional method preparation method by, and used as raw material for reduction process carbonyl functional is proceeded then may be loaded with.

[Formula 5]

(In formula, R carbon atoms 4 to 1 copyright 2000.)

A used in the process include alcohol, methanol, ethanol, n-propanol, i-propanol, n butyl alcohol, i butyl alcohol, : butyl alcohol t. At, reactive in terms of preferably methanol or ethanol.

Alcohol is used in an amount of, a carbonylation process a starting material for a compound in which a n mono 0.5-2.0 molar times, preferably 0.8-1.5 molar is an. 0.5 molar times larger than the surface and wherein the molar ratio of the alcohol, and the residual quantity of unreacted fluoride, post-processing equipment in corrosion and advantageous because a small, by inhibiting the dehydration reaction during the formation of alcohol molecules between in terms of inhibition of corrosion device hereinafter is preferably 2.0 molar times.

Acid fluoride and low molecular alcohol are reacted and reaction temperatures of the general formula (5) of carbonyl compounds cyclohexane represented by -40 °C or more in terms of an inhibitor of the degradation of the is 20 °C hereinafter. Esterification low output powers than -40 °C the slower the speed is hard mask as an ion implantation mask. Furthermore, composition of the ester above the 20 °C, adding response against dehydration of alcohols in the system and the number, such as by increased risk generated as a by-product from water.

Obtained by the formula (5) represented by cyclohexane carbonyl compounds after removing the for the distillative HF from, normal distillation the. purified by method.

<(d) 카르보닐기의 환원 공정 >

The process obtained in a general formula (5) cyclohexane represented by reduction of carbonyl compounds, generally reduced to alcohol carbonyl compounds or blocked from the internal of the method may be used in both if, has is not particularly limited in. For example, right 14 lecture chemical the experiments wave number 5 (floor feedstock, (Maruzen, [...]) stock Company) reduction hydride based on page 11-27, reduction of a metal salt of metal and, hydrogen contact of using all although it is possible, or the like, contact in terms of economy preferably reduction by hydrogenation of.

[Formula 6]

Cyclohexane of carbonyl compounds contact the catalyst employed in hydrogenation, used for the hydrogenation of carbonyl compounds in a generally but is not particularly limited in if catalyst, number 8-11 group metal selected from periodic table 1 species preferably a catalyst containing at least.

Specifically iron, cobalt, nickel, copper, ruthenium, rhodium, palladium, the, osmium, iridium, platinum and gold at least selected from contact containing a species, 1 can be a hydrogenation catalyst.

Contact the hydrogenation catalyst comprises an a, ; even with homogeneous catalysts even with solid catalyst, in terms of the separation of the reactant solid catalyst being preferred.. Solid catalyst non--supported metal catalyst such as catalyst carrying metal or is the exemplary.

Non-supported metal catalyst (1) Raney nickel, Raney cobalt, Raney such as copper of Raney catalyst, (2) platinum, palladium, rhodium, ruthenium such as oxides or colloidal catalyst being preferred..

Carrying metal catalyst, magnesia, zirconia, ceria, diatomite, activated carbon, alumina, silica, zeolite or a titania on a carrier such as, iron, cobalt, nickel, copper, ruthenium, rhodium, palladium, the, osmium, iridium, platinum gold during 1 containing at least one is the exemplary a or mixing the filler, copper-chromium catalyst (Adkins catalyst), copper-zinc catalyst or copper-like iron copper catalyst containing, or Pt/C Pt/alumina such as supported platinum catalyst, palladium catalyst containing Pd/C or Pd/alumina such as, or Ru/C Rh/C or ruthenium catalyst containing such as/alumina Ru or Rh/alumina such as. is preferable rhodium catalyst containing.

At, in terms of active reaction, selected from copper at least containing such a kind that an. is more preferred to set a catalyst use.

Contact hydrogenation catalyst is used in an amount of to accomplish different but depending on the type of catalyst, a cyclohexane carbonyl a compound in which a 1-100 mass %, preferably 3-30 mass %. suitable.

[Solvent]

Reduction processes carbonyl functional of the present invention can be executed in solvent but, .may be solvent.

Solvents comprise trialkylamines of reduction process carbonyl functional of the present invention, water, formic acid, acid such as acetic acid, benzene, o-dichloro benzene, toluene, xylene strain of an aromatic compounds and, hexane, heptane, hydrocarbons such as cyclohexane, methanol, ethanol, isopropyl alcohol, t butyl alcohol, ethylene glycol, diethylene ethylene glycol, alcohols, dioxane, for ease of application, [...] , such as ethers or mixtures thereof being a D writing, :. At, solvent, benzene, o-dichloro benzene, toluene, xylene strain of an aromatic compounds and, hexane, heptane, hydrocarbons such as cyclohexane, methanol, ethanol, isopropyl alcohol, t butyl alcohol, ethylene glycol, diethylene ethylene glycol, alcohols, dioxane, for ease of application, [...] , being a D writing, such as ethers or mixtures thereof it is preferable that the using.

Evaporating a solvent from reduction process carbonyl functional of the present invention when using a the amount of, the process obtained in a general formula (5) represented by a compound in which a carbonyl cyclohexane, generally 0-30 mass multiple of the tier and can range but, preferably 0-20 may bail mass.

[Reaction conditions]

Pressure of hydrogen in reduction process carbonyl functional of the present invention, reaction provision of alcohol by moving that finger or post toward but preferably a farther module and to high-pressure aspect that, considering the with a solvent are preferably present in the salt 1-30 MPa, which is more preferred to set a 2-20 MPa, more preferably, the is 5-10 MPa.

The reaction temperature in reduction process carbonyl functional of the present invention, sufficient in terms obtained reaction rates and is preferably at least 100 °C, 150 °C. is more preferred to set a or more. Furthermore, generating alicyclic alcohol and general formula (5) represented by cyclohexane carbonyl compounds for inhibiting the transesterification with 300 °C hereinafter in terms are preferably present in the salt, is preferably 280 °C hereinafter, more preferably, the is 250 °C hereinafter.

The first substrate are assembled form of reduction process carbonyl functional of the present invention is not limited. Contact, by hydrogenation in contact even when the mother pipe having a hydrogenation reaction embodiment possible that are not particularly limited and, of the commonly used publicly known preferably of. For example, contact the fluidized fluid catalyst hydrogenation the reaction takes place in the a reactor, fluid immobilised charging catalyst by supplying contact hydrogenation reaction such as fixed-bed reactor performing.

During the reactions is a by-product alcohol of 1-4 carbon atoms. Reaction is them, can be state or a compound thereof is present but, during the reactions and where they are removed continuously or intermittently may be while the radiation is performed.

A Y shaft servo motor including a alicyclic alcohol product obtained after the separation of the catalyst hydrogen from, the normal distillation method according to formula (1) compound of a purified liquid represented by novel alicyclic alcohol compound can cause.

In the embodiment

Hereinafter, embodiment and/or at least two different but described specifically for the present invention, the present invention refers to these embodiment and/or at least two different no limited not. Furthermore, in hereinafter, " %" has a special refused % mass not. mixture by the addition of an initiator.

<Gas chromatography analysis conditions >

Mono compound when analyze alcohol alicyclic and, the resistor "GC-17A" (all ; (main) [...] that have ever (Shimadzu Corporation, [...]) product) and a, capillary column (Capillary Column) in "HR-1" (all; shoes and chemical (Shinwa Chemical Industries Ltd. , chemical engineering) (main) product; 0.32 mmφ × 25m) by cylinder to have. Elevated temperature conditions until 250 °C from 100 °C 2 °C/min. adaptation elevated temperature.

Cyclohexane when analyze carbonyl compounds, the resistor "GC-17A" (name; product that have ever [...] (main)) "DBWAX" a capillary columns (all; J & W product; 0.32 mmφ × 30m × 0.25 µm) by cylinder to have. Elevated temperature conditions 5 °C/min. until 250 °C from 100 °C elevated temperature section.

< 조제예 1> [...] a by hydrogenation of 4-isopropyl-1-methyl vinylcyclohexenes (hereinafter, by in " other pinene -DH") preparation of

[Formula 7]

[...] stirrer and a type drive (NAC) 3 on top of inlet nozzle, object code compatible representation of 1 bottom ([...]) and nozzle comprises a tube-shaped base, and thereby control the temperature, by means of a jacket a the content volume of the pipeline 5 L stainless autoclave, cu-Cr catalyst ([...] catalyst resistant (main) (JGC C & C, day) product, all "N-203S") 50.0 g a, heptane (industrial sprout about waveguide (main) (Wako Pure Chemical Industries, shoe polishes (main) product; special grade) have a water 500.0 g a, 170 °C, 2 MPa hydrogen pressure activation time in the embodiment 1.

After cooling, limonene (chemical do[...] (Yasuhara Chemical Co. , Ltd.) product) have a water 500.0 g a, 95 °C, 2 MPa hydrogen pressure, agitating time 3 performed for all the hydrogenation reaction. Reaction solution to filter out and removing the catalyst, concentration vinylcyclohexenes methyl-1-isopropyl 4-49.0%, 1.4% 4-isopropyl-1-trimethylcyclohexane concentration, heptane concentration 49.6% containing reaction mixture obtained 957.4 g (92.5% yield).

< 실시예 1>

Isomerization and carbonylation other pinene -DH by directories esterase and 2-methyl-2-(4-aminocyclohexyl methyl)-propionic acid ethyl (hereinafter, "DH-ester" by to) for manufacturing

[Formula 8]

<A carbonylation process >

Stirrer and a type drive [...] 3 on top of inlet nozzle, and nozzle comprises a tube-shaped base object code compatible representation of bottom 1, and thereby control the temperature, by means of a jacket a the content volume of the pipeline 500 ml stainless auto [...] experiment using the embodiment.

First after substituted carbon monoxide by way of a interior vapour-sterilisable, hydrogen fluoride 105 g (5.3 mole) by introducing a starter and, after a -30 °C liquid temperature, on pressure until 2 MPa in carbon monoxide.

A truck is provided to maintain an -30 °C reaction temperature, reaction pressure 2 MPa in addition while maintaining the reaction solution made in e.g. preparation 1 (4-isopropyl-1-methyl vinylcyclohexenes concentration 49.0%, 4-isopropyl-1-trimethylcyclohexane concentration 1.4%, heptane concentration 49.6%)211.3 g (4-isopropyl-1-methyl vinylcyclohexenes: contain 0.75) of the fed from upper vapour-sterilisable embodiment the carbonylation reactions has. Supply after a time, the absorption of carbon monoxide are not recognized and went on agitation until about 10 minutes.

The obtained reaction liquid portion of ethanol cooling during sampling the equalized signal, water are added, oily and have been isolated. Furthermore, neutralizing oily, oily obtained results subject to analysis by a gas chromatography, 4-isopropyl-1-trimethylcyclohexane acid ethyl diastereomeric ratio is 93.5% (cis with elder brother the transformer-type total), 2-methyl-2-(4-aminocyclohexyl methyl) phenylpropionic acid ethyl diastereomeric ratio is 2.2% and, other isomer this method enables an accurate mixture in 4.2%.

[Formula 9]

< 이성화 공정, 에스테르화 공정 >

Furthermore, carbon monoxide pressure 1 MPa while maintaining the reaction solution 25 °C temperature and at elevated temperatures, 24, which has the temperature period. 24 process has been completed, the reaction temperature cooled to 0 °C, 51.8 g from the upper vapour-sterilisable ethanol (1.12 molar) supply, under stirring 1 embodiment the esterification time.

Reaction mixture during release the ice water from the bottom vapour-sterilisable, oily and after the separation of the aqueous phase, oily 2 times 100 ml to 2% caustic soda aqueous solution, which washes the times 2 to 100 ml distilled water, 10 g of anhydride was dewatered from a sodium sulfate. Liquid obtained results subject to analysis by gas chromatography, methyl trimethylcyclohexane-1-isopropyl 4-diastereomeric ratio is 52.4% (cis with elder brother the transformer-type total) and, 2-methyl-2-(4-aminocyclohexyl methyl) phenylpropionic acid ethyl diastereomeric ratio is 40.3% and, other isomer this method enables an accurate mixture in 7.2%.

[Formula 10]

that boiling water by and causes no obtained after removing the, short-lived theory 20 of corresponding advertisement based on the shown embodiment rectification using distillation column (150 °C temperature, vacuum 60 torr), 4-isopropyl-1-trimethylcyclohexane acid ethyl diastereomeric ratio is 52.1% (cis with elder brother the transformer-type total) and, 2-methyl-2-(4-aminocyclohexyl methyl) phenylpropionic acid ethyl diastereomeric ratio is 40.8% and, other isomer 7.1% in ester compounds, 136.1 g obtained as main oil ([...]) (2-methyl-2-(4-methyl aminocyclohexyl) phenylpropionic acid ethyl yield of 34.9 molar %, 4-isopropyl-1-methyl vinylcyclohexenes reference).

< in reduction[...] -aodirencDHT by DHT-alcohols {2-methyl-2-(4-aminocyclohexyl methyl) propane-1-ol} for manufacturing aodirenc (carbonyl functional reduction process)>

[Formula 11]

Stainless number autoclave, 5.3 g of alumina carried on the copper-zinc catalyst (catalyst [...] resistant product), 105 g of said main oil obtained in a mixture of esters of (4-isopropyl-1-trimethylcyclohexane acid ethyl diastereomeric ratio is 52.1% and, 2-methyl-2-(4-methyl aminocyclohexyl) phenylpropionic acid ethyl diastereomeric ratio is 40.8% and, other isomer includes a in 7.1%)doesn't have any error frames, , 10 MPa of hydrogen on board a solvent under hydrogen pressure to allow the circulation of 260 °C 14 while agitating in reduction reaction is performed for all the time.

Reaction solution to filter out and removing the catalyst, (cis-4-aminocyclohexyl methyl-1-isopropyl) 41.0% methanol, 2-methyl-2-(4-aminocyclohexyl methyl) propane-1-ol 39.0% an article containing been produced with at 68 g (mixture) of ((2-methyl-2-(4-methyl aminocyclohexyl) propane-1-ol yield 77.2 molar %, 2-methyl-2-(4-aminocyclohexyl methyl) phenylpropionic acid ethyl reference).

Obtained after removing the that boiling water into and causes no, theory of 50 using a short-lived circuit rectifies AC voltage and converts the result, and in separating the guide parts a major product, is 84.3% purity characterized in that a pair of subsidiary obtained, and non-greasy to the suck-in an anti-feeling [...] -green-like fragrance is tried to. Results subject to analysis by GC-MS, 170 have been shown to molecular weight of object. Furthermore, in (are heavily) chloroform solvent during¹ H-NMR chemical shift values (δppm, TMS reference) the 3.38 (s, 2H), 1.69-1.75 (m, 2H), 1.67-1.71 (m, 2H), 1.38 (br, 1H), 1.21-1.30 (m, 1H), 1.15-1.23 (m, 1H), 0.98-1.08 (m, 2H), 0.85-0.94 (m, 2H), 0.86 (d, J = 6.4Hz, 3H), 0.83 (s, 6H) the stopper groove, type (1) of (2-methyl-2-(4-aminocyclohexyl methyl)-1-propane found to gamer the ([...] ; identification).

< 실시예 2> [...] types of perfume composition

Table 1 with a composition which shown in 90 parts by mass of fragrance composition, obtained in a formula (1) in the embodiment 1 of alicyclic alcohol compound by adding parts by mass of 10, characterized by the and non-greasy to smell mu crab[...] types of perfume compositions can be obtained.

< 비교예 1> [...] types of perfume composition

Table 1 composition as the composition of perfume composition 90 parts by mass of a 10 mass parts (terpineol) it blooms and it comes terpene corresponding advertisement based on the shown list, the electric-spinning of ([...]) of lifting a freshened ([...]) was odor is disconnected.

< 비교예 2>

Table 1 composition as the composition of perfume composition 90 parts by mass of, with Neel roll sheet methylene cycle 10 mass parts (all of Firmenich) a corresponding advertisement based on the shown list, odor was enhanced all parts of a direct reduction process for iron-oxide.

In the embodiment 1 obtained at the alicyclic alcohol compound and non-greasy to the green sense of the since to more mu crab may emphasize odor.