WO2007088625A1

WO2007088625A1 - 7-hydroxy-9-methylpentadecane and process for production thereof

Info

Publication number: WO2007088625A1
Application number: PCT/JP2006/301790
Authority: WO
Inventors: Shutoku Ebisusaki; Yasuyuki Shimozato
Original assignee: Kokura Synthetic Industries, Ltd.; Nacos Kenkyusho Inc.
Priority date: 2006-02-02
Filing date: 2006-02-02
Publication date: 2007-08-09
Also published as: JPWO2007088625A1

Abstract

Disclosed is 7-hydroxy-9-methylpentadecane which, since it is a branched dimerized alcohol of a secondary alcohol and has a low viscosity, can be used as a starting material for the production of an ether or ester which is used in a product such as a surfactant, a lubricant, a plasticizer and a cosmetic to improve the handling property and productivity in the process for production of the product or in the process for production of an application product in which the product is used, and which is therefore excellent in usefulness. 7-Hydroxy-9-methylpentadecane having a structure of the chemical formula: CH3(CH2)5CH(OH)CH2CH(CH3)(CH2)5CH3 (1).

Description

Specification

7-Hydroxy-9-methylpentadecane and process for producing the same

Technical field

[0001] The present invention relates to 7-hydroxy-9-methylpentadecane, which is a novel dimerized alcohol, and a method for producing the same.

Background art

Conventionally, long-chain aliphatic alcohols having 8 to 30 carbon atoms have been used as raw materials for ethers and esters used in surfactants, lubricating oils, plasticizers, cosmetics, and the like. Of these aliphatic alcohols, surfactants, lubricating oils, plasticizers and cosmetics using ethers and esters obtained with straight chain aliphatic alcohol strength become highly viscous, and soon these products. In the manufacturing process and the manufacturing process of applied products using these products, it is a problem as a cause of poor productivity and low productivity. For this reason, low viscosity ethers and esters that can be used as raw materials for surfactants and the like have been sought, and attempts have been made to use branched aliphatic alcohols as raw materials as a solution. For example, 2-ethylhexanol, 2-butyloctanol, 2-hexyldecanol or 2-octyldodecanol have been used as raw materials. These branched alcohols are known to be obtained by dimerization of linear primary alcohols by the Gelbe reaction, as shown in, for example, (Patent Document 1) to (Patent Document 3). 1: JP-A-49-35308

Patent Document 2: Japanese Patent Application Laid-Open No. 64-34933

Patent Document 3: Japanese Patent Laid-Open No. 2-286638

Disclosure of the invention

Problems to be solved by the invention

[0003] However, the conventional techniques described above have the following problems.

(1) Since the branched dimerized alcohol obtained by the techniques disclosed in (Patent Document 1) to (Patent Document 3) is a primary alcohol, the ethers and esters obtained from this are used as raw materials. In the manufacturing process of surfactants, lubricating oils, plasticizers, cosmetics, etc. and the manufacturing processes of these applied products, the viscosity is low enough to improve the handling and productivity. I was confident that I had problems.

(2) In order to reduce the viscosity, it is possible to use dimerized alcohol of secondary alcohol obtained by gel reaction of secondary alcohol. When secondary alcohol is used, gel reaction On the other hand, there is a problem that it is difficult to mass-produce with a low yield because it easily generates a lower carboxylic acid with acid decomposition.

(3) Furthermore, when a gel reaction is performed using a secondary alcohol as a raw material, a ketone is produced in the reaction process, so the dimerized alcohol of the secondary alcohol obtained by the gel reaction has two types in terms of its structure. A dimeric alcohol having the following chemical structural formula is obtained. These two types of dimeric alcohols have almost no difference in boiling point, making it difficult to separate and purify them.It is difficult to mass-produce dimeric alcohols because of their high purity. And then

[0004] The present invention solves the above-described conventional problems, and is a branched dimeric alcohol of a secondary alcohol and has low viscosity. Therefore, surfactants, lubricating oils, plasticizers, cosmetics, etc. 7-Hydroxy-9-methylpentadecane as a raw material for ethers and esters used in foods, which can improve handling and productivity in the manufacturing process of these products and in the manufacturing process of applied products using these products. The purpose is to provide.

In addition, since the present invention uses 2-octanol, which is a secondary alcohol, as a raw material, the raw material can be easily obtained, and water is also removed from 2-octanol with 2 molecular forces by gel reaction, so that 1 molecule of dimeric alcohol can be obtained. It is an object of the present invention to provide a method for producing 7-hydroxy-9-methylpentadecane, which is capable of mass-producing 7-hydroxy-9-methylpentadecane having a low cost and high purity since a reaction product containing such a product can be obtained.

Means for solving the problem

In order to solve the above conventional problems, the 7-hydroxy-9-methylpentadecane and the method for producing the same of the present invention have the following configurations.

7-Hydroxy-9-methylpentadecane according to claim 1 of the present invention has the chemical formula CH

Three

(CH) CH (OH) CH CH (CH) (CH) CH ... (1). With this configuration, the following effects can be obtained.

(1) 7-Hydroxy-9-methylpentadecane is a branched dimerized alcohol of secondary alcohol and has low viscosity, so it is an ether used in surfactants, lubricants, plasticizers, cosmetics, etc. As a raw material for alcohols and esters, it can improve handling and productivity in the manufacturing process of these products and the manufacturing process of applied products using these products.

[0006] Here, 7-hydroxy-9-methylpentadecane is a new chemical substance that has been successfully synthesized by the present inventors, and has the chemical formula CH (CH) CH (OH) CH CH (CH) (CH) CH

3 2 5 2 3 2 5 3

Shown in (1). Since the 7th and 9th carbons are asymmetric carbons, they are diastereomer structures. Therefore, theoretically, it is a collection of compounds that constitute a force racemate in which four stereoisomers exist, and at present, these optical resolutions cannot be performed.

However, it was found that there were two peaks in the measurement by gas chromatography. These two peaks are thought to be due to diastereomers, and the results of NMR spectrum measurements can be supported.

[0007] The method for producing 7-hydroxy-9-methylpentadecane according to claim 2 of the present invention is a configuration in which 2-year-old octanol is heated and condensed in the presence of a catalyst composed of an alkaline substance and a metal catalyst to obtain a reaction product. Have

With this configuration, the following effects can be obtained.

(1) When 2-year-old octanol is heat-condensed in the presence of a catalyst consisting of an alkaline substance and a metal catalyst, 2-octanol, 2 molecular force water is removed by gel reaction, and 1 molecule of dimerized alcohol is contained. Since the reaction product is obtained, mass production is possible at low cost.

(2) Although 2-octanol as a raw material was a secondary alcohol, it was found that the dimeric alcohol obtained by the Gerbe reaction had only one chemical structural formula. This eliminates the need for separation and purification and enables mass production of high-purity dimer alcohol.

[0008] Here, as a catalyst having alkaline substance power, metal sodium, sodium alcoholate, sodium hydroxide, sodium carbonate, sodium amide, metal potassium, potassium hydroxide hydroxide, power Examples include lithium amide, potassium carbonate, potassium phosphate, and lithium hydroxide.

Among these, alkali metal hydroxides are preferably used. This is because the handleability is excellent. The addition amount of the catalyst is preferably 0.01 to 10 parts by mass, preferably 0.02 to 8 parts by mass, more preferably 0.03 to 5 parts by mass with respect to 100 parts by mass of 2-octanol. It is. As the amount added is less than 0.03 parts by mass, the reaction rate tends to decrease and the yield tends to decrease, and as the amount exceeds 5 parts by mass, the amount of high-boiling by-products such as trimers tends to increase. Is seen. These tendencies become more pronounced as the amount added is less than 0.02 parts by mass and as the amount added exceeds 8 parts by mass. In particular, when the amount added is less than 0.01 parts by mass or more than 10 parts by mass, these tendencies become remarkable, which is not preferable.

A method of adding a catalyst having an alkaline substance power in a solid state or a method of adding it in an aqueous solution. It is preferable that the catalyst is added in an aqueous solution because it can be homogenized more quickly. The aqueous solution preferably has a concentration as high as possible. This is because the reaction rate can be increased and the energy required for distilling off water can be reduced.

Examples of metal catalysts that can be used include copper chromite, copper zinc, copper powder, zinc oxide, zinc chromite, and stabilized nickel. Raney catalysts such as nickel, chromium and copper, and Group 8 platinum group elements such as nickel, platinum, noradium, ruthenium and rhodium can also be used. These complex compounds (for example, complex compounds with trialkylamine, triphenylphosphine, etc.) can also be used. Further, those having a group 8 platinum group element or the like supported on a carrier can also be used.

As the carrier, alumina, silica alumina, diatomaceous earth, silica, carbon, activated carbon, natural or synthetic zeolite can be used.

As the loading amount of the group 8 platinum element or the like on the carrier, 0.05 to 15% by mass, preferably 1 to 10% by mass is suitably used. As the loading amount decreases below 1% by mass, the reaction rate tends to decrease. As the loading amount increases above 10% by mass, the effect corresponding to the amount added cannot be obtained, and the running cost tends to increase. . In particular, if it is less than 0.05% by mass or more than 15% by mass, these tendencies become remarkable, which is not preferable.

Among these metal catalysts, Group 8 supported on Raney nickel or carbon. Platinum group elements are preferably used. This is because coloring of the reaction product can be prevented.

The metal catalyst is added in the form of powder, and the addition amount is preferably 0.01 to 5 parts by mass, more preferably 0.05 to 4 parts by mass with respect to 100 parts by mass of 2-octanol. As the amount added is less than 0.05 parts by mass, the reaction rate tends to decrease and the yield tends to decrease. As the amount exceeds 4 parts by mass, the reaction rate increases but the running cost tends to increase. In particular, if the addition amount is less than 0.01 parts by mass, and if the addition amount is more than 5 parts by mass, these tendencies tend to become remarkable, which is not preferable.

[0010] The temperature for heat condensation is preferably 120 to 260 ° C. If the temperature is lower than 120 ° C, water is not removed, and the gel reaction may not proceed. Also, when the temperature is higher than 260 ° C, by-products such as high boiling point substances other than dimer alcohol are produced, which is not preferable.

[0011] The invention described in claim 3 of the present invention is the process for producing 7hydroxy-9methylpentadecane according to claim 2, wherein the reaction product is hydrogenated. With this configuration, in addition to the operation obtained in claim 2, the following operation can be obtained. (1) The reaction product is diminished and converted to an alcohol, but there is also a compound, so that dimer alcohol can be obtained by hydrogenating this compound. The yield of 7-hydroxy-9-methylpentadecane can be increased. Compared to the reaction product obtained by the gel reaction of primary alcohol, the reaction product obtained by the gel reaction of 2-octanol is converted to dimer alcohol, resulting in a large amount of compound formation. Therefore, it is possible to increase the amount of dimerized alcohol produced by hydrogenating the reactants.

[0012] Here, as a method for hydrogenating the reactants, Group 8 elements of the periodic table such as iron, cobalt, nickel, platinum, palladium, ruthenium, rhodium, copper, rhenium, Raney catalyst, boride nickel A method of catalytic hydrogenation using a hydrogenation catalyst such as a catalyst is used. In order to stabilize the activity at high temperatures, the hydrogenation catalyst may be supported on a support such as alumina, silica alumina, diatomaceous earth, silica, carbon, activated carbon, natural or synthetic zeolite.

In addition, acidic reducing agents such as zinc Z acetic acid, iron Z acetic acid, zinc Z caustic soda, sodium Z Alkali reducing agents such as lucol and sodium amalgam and neutral reducing agents such as aluminum amalgam can also be used.

[0013] Hydrogenation conditions include a hydrogen pressure of 2 to 5 MPa, a reaction temperature of 70 to 150 ° C, and a reaction time of 1 to

It is preferably performed in 5 hours. If the hydrogen pressure is less than 2MPa, hydrogenation will not be performed sufficiently. It is complicated and lacks productivity. Also, if the reaction temperature is less than 70 ° C, the reaction takes a long time and the productivity is lowered, and if it exceeds 150 ° C, the tendency to cause reverse reaction (dehydrogenation) increases. In addition, when the reaction time is less than 1 hour, hydrogenation is not sufficiently performed, and when it exceeds 5 hours, productivity is lowered.

[0014] It should be noted that the purity of 7-hydroxy-9-methylpentadecane can be further increased by hydrogenating the reaction product and, if necessary, separating and purifying with a column, if necessary.

[0015] The invention according to claim 4 of the present invention is the process for producing 7-hydroxy-9-methylpentadecane according to claim 2 or 3, wherein the 2-octanol power castor oil or ricinoleic acid is used. Is heated and decomposed with an alkali agent.

With this configuration, in addition to the effects obtained in claim 2 or 3, the following effects can be obtained.

(1) 2-octanol power A compound derived from castor oil and ricinoleic acid that is obtained by squeezing castor bean seeds, which is not a petrochemical-derived compound, so it has excellent resource conservation and environmental conservation.

[0016] Here, as the alkali agent, sodium hydroxide, potassium hydroxide, lithium hydroxide or the like can be used!

The invention's effect

[0017] As described above, according to the 7-hydroxy-9-methylpentadecane and the production method thereof of the present invention, the following advantageous effects can be obtained.

According to the invention of claim 1,

(1) Secondary alcohol is a branched dimeric alcohol, so its viscosity is low! Therefore, ethers and esters used in surfactants, lubricants, plasticizers, cosmetics, etc. Raw materials and In addition, it is possible to provide 7-hydroxy-9-methylpentadecane that has improved usability and productivity in the manufacturing process of surfactants and the manufacturing process of applied products using surfactants. it can.

[0018] According to the invention of claim 2,

(1) Since 2-octanol as a raw material is a secondary alcohol obtained by alkaline decomposition of ricinoleic acid in castor oil, 2-octanol can be easily obtained. When heat-condensed in the presence of a catalyst, water is removed from two molecules of 2-octanol by the Gerbe reaction and a reaction product containing one molecule of dimerized alcohol is obtained, enabling mass production at low cost and increasing mass productivity. An excellent method for producing 7-hydroxy-9-methylpentadecane can be provided.

(2) Since dimeric alcohol obtained by Gerber reaction has only one chemical structural formula, it is not necessary to separate and purify, and mass production of high purity dimeric alcohol is possible. A method for producing hydroxy-9-methylpentadecane can be provided.

[0019] According to the invention of claim 3, in addition to the effect of claim 2,

(1) The reaction product is diminished and converted to an alcohol, but there is also a compound, so that dimer alcohol can be obtained by hydrogenating this compound. Thus, it is possible to provide 7-hydroxy-9-methylpentadecane and a method for producing the same, which can increase the yield of 7-hydroxy-9-methylpentadecane.

[0020] According to the invention of claim 4, in addition to the effect of claim 2 or 3,

(1) 2-octanol power Since it is a plant-derived compound of castor oil and ricinoleic acid obtained by squeezing castor sesame seeds, which is not a petrochemical-derived compound, it is excellent in resource conservation and environmental conservation. It is possible to provide a method for producing hydroxy-9-methylpentadecane.

Brief Description of Drawings

[0021] C ¹³ NMR ^ vector of [1] a compound of a first peak in a fraction of Example 1

[FIG. 2] C ¹³ NMR ^ vector of the second peak compound in the fraction of Experimental Example 1 BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, the present invention will be specifically described with reference to examples. The present invention is based on these examples. It is not limited.

(Experiment 1)

Thermometer necked 1 liter flask, stirrer, reflux condenser with water separator was attached, 2 - Okutanoru and (Kokura Synthetic Industries, Ltd.) 400 g, 48 mass ^_0/0 water as an alkaline substance mosquitoゝet consisting catalyst 0.65 g (0.08 parts by mass with respect to 100 parts by mass of 2-octanol) aqueous solution of potassium oxalate (manufactured by Hayashi Junyaku Kogyo Co., Ltd.) and palladium on carbon (5% by mass supported) as metal catalyst (D (Neuchem Cat) 1. 6 g (0.4 parts by mass with respect to 100 parts by mass of 2-octanol) was heated and heated. The reaction product was obtained by heating to the boiling point of 2-octanol (179 ° C) and continuing to reflux for 6 hours. Incidentally, 2-octanol is obtained by saponifying castor oil to take out ricinoleic acid, decomposing it by heating ricinoleic acid together with an alkaline agent, and distilling it. The temperature of the reaction product at the end of the reaction was 220 ° C. After filtering the carbon-supported palladium in the reaction product, the reaction product was washed with water. Add 2g of Raney nickel (Nikko Rica, Sponginickel catalyst R-200) hydrogenation catalyst to this reaction product at 4MPa hydrogen pressure, and perform hydrogenation reaction at 110 ° C for 4 hours. The reaction mixture was distilled.

As a result, a fraction having a boiling point of 140 ° C. (6.0 ^× 10 ^_4 MPa) was collected. The yield was 241g.

(Evaluation of fraction)

The obtained fraction was evaluated by the following means.

(1) Gas chromatography (Shimadzu, GC-14B): Column DB-1 (J & W Sclent ific) was used and the column temperature was increased from 80 ° C to 10 ° C / min, reaching 300 ° C. The temperature was measured for 10 minutes after that.

(2) NMR: A proton NMR spectrum and C ¹³ NMR using a 500 MHz nuclear magnetic resonance apparatus (JNM-A500, manufactured by JEOL Ltd.) with a sample dissolved in heavy chloroform and tetramethylsilane as an internal standard. ^ Vector measured.

(3) High-resolution mass spectrum: Measured by the FAB method using a double-focusing gas chromatograph mass spectrometer (JEOL, JMS-SX102A).

(4) Hydroxyl value: Determined according to JIS K0070-1992.

(5) Iodine value: Determined according to JIS K0070-1992. (6) Viscosity: Measured using a TV-2 type viscometer (cone plate type) manufactured by Toki Sangyo in accordance with JIS K7117-2: 1999. The measurement temperature was 25 ° C.

[0024] This fraction had two peaks from gas chromatography. The purity analyzed by gas chromatography was 98.5%. Further, the refractive index n ² D = l. 4465, and the hydrogen value was 0.6.

From this fraction, two peak compounds on gas chromatography were separated as single products by column chromatography (column: silica gel) using hexyl acetate (9Z1) as a developing solvent.

Next, high-resolution mass spectra were measured for these two single compounds. The molecular weights obtained from the high resolution mass spectrum were 225.2552 and 225.2592, respectively. This agrees well with the calculated molecular weight of 225.2584 for the chemical formula C H. Therefore,

16 33

The molecular weight indicated by the high-resolution mass spectrum was identified as the molecular weight of C H. However,

16 33

In the FAB method, the molecular weight is observed as M (molecular weight) + 1, so it can be estimated that the actual molecular weight is 224. Furthermore, each fragmentation was the same.

Next, the hydroxyl value of this fraction was 225 (theoretical value 231). In addition, this fraction was converted to TMS by gas chromatography after trimethylsilyl (TMS) conversion. Therefore, it was confirmed that the compound of this fraction has a hydroxyl group. From the above, it was determined that the molecular weight 224 obtained from the high-resolution mass spectrum was the molecular weight of the compound dehydrated during the measurement of the mass spectrum. In other words, the two peaks in the gas chromatograph are molecular weight 242 (molecular weight 224 plus HO molecular weight 18).

2

It was found to be a dimerized alcohol having the chemical formula C 3 H 2 O.

16 34

An NMR spectrum was measured for each compound isolated from two peaks (hereinafter referred to as the first peak and the second peak) of the gas chromatograph. The C ¹³ NMR ^ vector of the first peak compound is shown in FIG. 1, and the C ¹³ NMR spectrum of the second peak compound is shown in FIG.

[0025] From the results of two-dimensional NMR with C ¹³ NMR and proton NMR, the absorption position of C ¹³ NMR of carbon at each position can be assigned as shown in (Table 1). The carbon at each position is represented by formula (2). C'H C ² HC ³ HC ⁴ HC ⁵ HC ⁶ HC ⁷ H (OH) C ⁸ HC ⁹ H (C ¹⁶ H) -C ¹⁰ HCH c

3 2 2 2 2 2 2 3 2 2

¹² HC ¹³ HC ¹⁴ HC ¹⁵ H --- (2)

2 2 2 3

[0026] [Table 1]

(Unit: ppm)

[0027] From the above results, both compounds showing two peaks of the above-mentioned fraction are 7-hydroxy-9-me. It was determined to be tilpentadecane. The two peaks are diastereomeric.

The viscosity of this fraction (compound having two peaks) was 3 ImPa · s.

[0028] In Experimental Example 1, the reactants before hydrogenation (immediately after washing with water) were found to be 4% raw material (2-year-old): 84% dimerized product, 84% high boiling point, based on the results of gas chromatography. (Trimer and higher boiling point substances): 10%, unidentified substance: 2%. In addition, 84% of the dimer product was found to be 7% hydroxy 9-methylpentadecane: 17%, 9-methylpentadecane 7-on: 67%, not hydrogenated It was confirmed that there was.

It was found that 99% of 9-methylpentadecane 7-on: 67% can be converted to 7-hydroxy-9-methylpentadecane by hydrogenating the reaction. From the above, it became clear that the yield of 7-hydroxy 9-methylpentadecane can be dramatically increased by hydrogenating the reactants.

[0029] (Experiment 2)

The 7-hydroxy-9-methylpentadecane of Experimental Example 2 was used in the same manner as in Experimental Example 1, except that Raney nickel (Nikko Rica, Spondeckel Catalyst R-200) was used instead of palladium on carbon as the metal catalyst. Obtained. The yield is 153g and the purity is 96.3%.

[0030] (Experiment 3)

Experimental example, except that a 48% aqueous solution of sodium hydroxide 2. lg (0.25 parts by mass with respect to 100 parts by mass of 2-octanol) was used instead of the potassium hydroxide aqueous solution as a catalyst consisting of an alkaline substance. In the same manner as in Example 1, 7-hydroxy-9-methylpentadecane of Experimental Example 3 was obtained. The yield was 206g and the purity was 98.8%.

[0031] (Experimental example 4)

As Example 1 except that 4 g of a 10% aqueous solution of lithium hydroxide (0.10 parts by mass per 100 parts by mass of 2-octanol) was used as the catalyst consisting of the alkaline substance instead of the aqueous potassium hydroxide solution. In this way, 7-hydroxy-9-methylpentadecane of Experimental Example 4 was obtained. The yield was 195g and the purity was 98.9%. [0032] (Experimental example 5)

Except for using carbon supported platinum (1% by weight supported) (manufactured by Nychemcat) instead of carbon supported palladium as the metal catalyst, 7-hydroxy-9 in Experimental Example 5 was used. —Methyl pentadecane was obtained. The yield is 210g and the purity is 98.0%.

[0033] (Experimental example 6)

Except for using carbon-supported ruthenium (supported by 5% by mass) (manufactured by EN'Chemcat) instead of carbon-supported palladium as the metal catalyst, the same as in Experimental Example 1, Got. The yield was 234g and the purity was 97.0%.

[0034] (Experimental example 7)

Experimental Example 7 7-hydroxy-9-methyl in the same manner as Experimental Example 1, except that carbon-supported rhodium (supported by 5% by mass) (manufactured by EN'Chemcat) was used as the metal catalyst instead of carbon-supported palladium. Pentadecane was obtained. The yield was 221 g and the purity was 98.3%.

[0035] (Comparative Example 1)

1-year-old kutanol (manufactured by Hayashi Junyaku Kogyo Co., Ltd., reagent grade) was used instead of 2-year-old kutanol and heated to 1-octanol boiling point (195 ° C) with potassium hydroxide and palladium on carbon supported. Except for the above, a reaction product was obtained in the same manner as in Experimental Example 1. The final temperature of the reaction was 235 ° C. After filtering the palladium on carbon in the reaction product, the reaction product was washed with water to obtain the reaction product of Comparative Example 1.

When the reaction product was analyzed using gas chromatography, the dimerization product in the reaction product was 2-hexyldecanol, accounting for 96% even though the hydrogenation reaction was not performed. This was distilled to obtain 2-hexyldecanol. The yield of 2-hexyldecanol was 239 g and the purity was 96%. The viscosity of 2 hexyldecanol was 39 mPa · s, which was 20% or more higher than the viscosity of 7hydroxy9-methylpentadecane in Experimental Example 1.

[0036] (Experimental example 8) The distillate was treated in the same manner as in Experimental Example 1 except that 0.02 g of 48% aqueous solution of potassium hydroxide and potassium (0.002 parts by mass with respect to 100 parts by mass of 2-octanol) was added as a catalyst with alkaline substance power Obtained. The distillate was almost free from dimers. Since the amount of catalyst added was small, it was presumed that the gel reaction almost proceeded.

[0037] (Experiment 9)

A fraction was obtained in the same manner as in Experimental Example 1, except that lOOg of 48% aqueous solution of potassium hydroxide and potassium (12 parts by mass with respect to 100 parts by mass of 2-otathanol) was added as a catalyst having alkaline substance power. In the case of this experimental example, a large amount of high-boiling substances other than the dimerization product was produced in the fraction, and the yield of 7-hydroxy 9-methylpentadecane was as low as 35 g (purity 88%).

[0038] (Experiment 10)

A fraction was obtained in the same manner as in Experimental Example 1, except that carbon-supported palladium (0.0 Olg, 0.003 parts by mass with respect to 100 parts by mass of 2-octanol) was added as a metal catalyst. In this experimental example, the gel reaction stopped, and the yield of 7-hydroxy-9-methylpentadecane was as low as 20 g (purity 85%).

[0039] (Experimental example 11)

A fraction was obtained in the same manner as in Experimental Example 1 except that a copper chromic acid catalyst (manufactured by Nyogakugyo Co., Ltd.) was used instead of palladium on carbon as the metal catalyst. In the case of this experimental example, the reaction product is colored, and at the same time, a large amount of high-boiling products other than dimerization products are formed in the fraction, and the yield of 7-hydroxy 9-methylpentadecane is as low as 70 g (purity 86%). Met.

[0040] (Experimental example 12)

A fraction was collected in the same manner as in Experimental Example 1 except that the hydrogenation reaction conditions of the reactant were changed to hydrogen pressure lMPa and 110 ° C. for 4 hours.

In Experimental Example 12, by hydrogenating the reactant, only about 6% of 67% of 9-methylpentadecane 7-one could be converted into 7-hydroxy-9-methylpentadecane.

As described above, according to this example, the secondary alcohol was used in a very high yield similar to the yield of the dimerization alcohol of Comparative Example 1 using the primary alcohol. High purity 7-Hydroxy-9-methylpentadecane can be obtained, and it has become clear that it can provide a process for producing 7-hydroxy-9-methylpentadecane, which is remarkably excellent in productivity.

The present invention relates to a novel dimerized alcohol 7-hydroxy-9-methylpentadecane and a method for producing the same, and since it is a branched dimer alcohol of secondary alcohol and has a low viscosity, a surfactant, a lubricating oil, As raw materials for ethers and esters used in plasticizers and cosmetics, etc., it is possible to improve handling and productivity in the manufacturing process of these products and the manufacturing process of applied products using these products. —Hydroxy-9 —Methylpentadecane can be provided, and since 2-otatanol, a secondary alcohol, is used as a raw material, the raw material can be easily obtained. 7-Hydroxy-9-methylpentadecane can be mass-produced at low cost because water is removed and a reaction product containing one molecule of dimeric alcohol is obtained. It is possible to provide a manufacturing method.

Claims

The scope of the claims

[1] Chemical formula

CH (CH) CH (OH) CH CH (CH) (CH) CH… hi)

3 2 5 2 3 2 5 3

7-hydroxy-9-methylpentadecane represented by

[2] A process for producing 7-hydroxy-9-methylpentadecane, characterized in that a reaction product is obtained by heat-condensing 2-year-old octanol in the presence of a catalyst composed of an alkaline substance and a metal catalyst.

[3] The process for producing 7-hydroxy-9-methylpentadecane according to claim 2, wherein the reactant is hydrogenated.

[4] The process for producing 7-hydroxy-9-methylpentadecane according to claim 2 or 3, wherein the 2-octanol power castor oil or ricinoleic acid is decomposed by heating with an alkali agent.