JPS6112908B2 - - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention is useful in a wide range of industrial fields including the oil and fat/flavor industry, and is useful as a synthetic intermediate, and is particularly attracting attention as an intermediate for the production of macrocyclic jacquard fragrances. The present invention relates to ω-hydroxy- or ω-acyloxy-alkyl-γ-butyrolactones, which are useful as intermediate lactones in the production of omega-hydroxy fatty acids and other synthetic fields, and which have not been described in any previously known literature, and methods for their production.

More specifically, an intermediate lactone that can produce omega-hydroxy fatty acids from inexpensive and easily available raw materials with a high conversion rate and high selectivity through a significantly shortened process and extremely easy operation, and a method for producing the same. Furthermore, the present invention relates to a novel lactone useful for providing a method for producing omega-hydroxy fatty acids that is industrially significantly advantageous in that troubles in wastewater treatment can be substantially eliminated, and a method for producing the same.

Conventionally, many methods are known for producing omega-hydroxy fatty acids, but these methods require multiple steps and complicated operations, are dangerous, or require the use of expensive reagents. For example, Okuda, "Fragrance Chemistry Overview", January 15, 1961, published by Hirokawa Shoten, 1211. The following manufacturing method, which is introduced on page 1, is known.

As shown in the above process formula, the conventional method requires multiple steps and complicated operations, requires the use of expensive reagents, and the yield in the above example is about 40% at most.
The extent of this is unsatisfactory.

The present inventors have conducted research to provide a method for producing omega-hydroxy fatty acids that can overcome the disadvantages of conventional methods as described above. As a result, the following formula (2), However, in the formula, R represents hydrogen or an acyl group,
By catalytically reacting ω-hydroxy- or ω-acyloxy-alkyl-γ-butyrolactone represented by n represents an integer of 0 to 18 in the presence of a hydrogenolysis catalyst, the following formula (1) can be obtained. , ROCH ₂ (CH ₂ ) _o CH ₂ CH ₂ CH ₂ COOH (1) However, in the formula, R and n have the same meanings as in the formula (2)'. It has been discovered that it can be produced industrially with high selectivity.

Furthermore, the above formula (2)'butyrolactones is represented by the following formula:
(3)', HOCH ₂ (CH ₂ ) _o CH ₂ OH (3)' where n has the same meaning as described for formula (2)'; ), CH ₂ ＝CHCOOR′ (4) where R′ represents hydrogen or an alkyl group, and is reacted with similarly inexpensive and easily available acrylic acid or its alkyl ester represented by the following in the presence of a radical catalyst. Furthermore, if desired, the obtained ω-hydroxy-alkyl-γ-butyrolactone can be acylated in a high yield, thus requiring two to three steps and a process that is significantly shortened compared to conventional methods. It has now been discovered that omega-hydroxy fatty acids can be produced from diols acrylic acid or alkyl esters with a markedly easier operation and with high conversion and selectivity. Furthermore, this newly developed manufacturing method can substantially eliminate the troubles of wastewater treatment that cannot be avoided with conventional methods, which is an extremely advantageous industrial method.
It has been found that a method for producing hydroxy fatty acids can be provided.

Furthermore, in the above formula (2)′ compound, the following formula (2) However, in the formula, R represents hydrogen or an acyl group derived from a _C1 to _C10 aliphatic monocarboxylic acid, and n represents an integer of 4 to 18. ω-hydroxy- or ω-acyloxy- Alkyl-γ-butyrolactone is, as far as the present inventors know, a compound that has not been previously described in any literature, and is useful not only as an intermediate for producing omega-hydroxy fatty acids but also as an intermediate lactone in other synthetic fields.

The new compound of formula (2) has the following formula (3) HOCH ₂ (CH ₂ ) _o CH ₂ OH (3) in the formula (3)' diol described in the production of formula (2)' butyrolactones. However, in the formula, n represents an integer of 4 to 18. It can be produced in the same manner except that a diol represented by the following is used.

Therefore, the object of the present invention is, for example, to
The novel ω-hydroxy- or ω-acyloxy-alkyl-γ. To provide butyrolactone and a method for producing the same.

The above objects and other objects and advantages of the present invention will become more apparent from the following description.

For ease of understanding, the process including the production of the formula (2) compound from the formula (3) and formula (4) compounds, and up to the production of the formula (1) omega-hydroxy fatty acid, for example, will be diagrammatically shown. It can be expressed as shown in the following formula.

The formula (2) butyrolactones used in the present invention can be produced by reacting the formula (3) diol and the formula (4) acrylic acid or its alkyl ester in the presence of a radical catalyst, and optionally, Obtained formula below In the above formula (2) compound represented by, R is hydrogen, which can be easily obtained in high yield by acylating the compound with a C ₁ to _{C 10} aliphatic monocarboxylic acid or an acid anhydride thereof. can.

Specific examples of α・ω-diols of the above formula (3) include 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9
-nonanediol, 1,10-decanediol,
1,11-undecanediol, 1,12-dodecanediol, 1,13-tridecanediol, 1,14
-tetradecanediol, 1,15 pentadecanediol, 1,16-hexadecanediol, 1,17
Diols of formula (3) such as -heptadecanediol and 1,18-octadecanediol can be mentioned. Further, as the acrylic acid or its alkyl ester of the above formula (4), for example, acrylic acid,
Methyl acrylate, ethyl acrylate, n-propyl acrylate, iso-propyl acrylate, n-butyl acrylate, iso-butyl acrylate,
Preferred examples include acrylic acid and its C ₁ -C ₆ lower alkyl esters such as sec-butyl acrylate, tert-butyl acrylate, n-amyl acrylate, iso-amyl acrylate, and hexyl acrylate. Further, as the radical catalyst used in the reaction, it is preferable to use a peroxide catalyst, and it is particularly preferable to use an organic peroxide catalyst. Examples of such radical catalysts generally include dialkyl peroxides such as ditert-butyl peroxide, hydroperoxides such as tert-butyl hydroperoxide, diacetyl peroxides such as diacetyl peroxide, and benzoyl peroxide. I can do it. Particular preference is given to using ditertiary butyl peroxide (DTBP).

The reaction between diols of formula (3) and acrylic acid or alkyl esters thereof (formula (4) as described above is carried out by combining the compound of formula (3) and the compound of formula (4) in the presence of a radical catalyst as exemplified above. This can be done by bringing them into contact. The reaction can be carried out in the absence of a solvent, but, if desired, it can also be carried out in the presence of an inert liquid medium, examples of which include, for example, aliphatic ethers such as n-butyl ether. Examples include aromatic hydrocarbons such as t-butylbenzene and the like, glymes, and decalin. The reaction is preferably carried out by heating under pressurized conditions of atmospheric pressure to about 20 kg/cm ² , for example about 100 kg/cm 2 .
Temperatures in the range of -200°C, preferably about 130°C to about 170°C, more preferably about 140°C to about 160°C, are utilized. The reaction time can be selected as appropriate, for example,
This can be done in about 3 to about 8 hours. The amount of the diol of formula (3) relative to the compound of formula (4) can be appropriately selected, and for example, about 5 to about 15 moles can be used.
In addition, in the method of the present invention, the formula in which R is an acyl group
(2) When using butyrolactones, ω-hydroxy-alkyl-γ obtained as described above
- It can be easily obtained by acylating butyrolactone. This acylation reaction can be easily carried out, for example, when R is a methyl group, by reacting with acetic anhydride. The reaction can also be carried out in the presence of an acid catalyst, such as phosphoric acid, sulfuric acid, para-toluenesulfonic acid, or a cation exchange resin such as Amberlyst 15 (trade name: Rohm & Haas Company). can. The reaction can be carried out at a temperature of about room temperature to about 120°C, and can be carried out for about 1 hour to about 6 hours. The amount of the acylating agent can also be selected appropriately, and is most commonly employed in a range from about the theoretical amount to about 5 times the mole. Examples of acylating agents include acetic acid, propionic acid, butyric acid, isobutyric acid, grass acid, isoceric acid, hexylic acid, isohexylic acid, heptylic acid, isoheptylic acid, octylic acid, isooctylic acid, nonylic acid, isononylic acid, etc., and their acids. Examples include anhydrides.
Among these, use of n-lower fatty acids and their acid anhydrides is preferred. The reaction can also be carried out in the presence of a solvent, for example aromatic and fatty acid hydrocarbons such as toluene, benzene, hexane, cyclohexane.

According to the present invention, as described above, the following formula (2) However, in the formula, R represents hydrogen or an acyl group derived from a _C1 to _C10 aliphatic monocarboxylic acid, and n is 4 to 18, preferably 4 to 16, particularly 7
A novel ω-hydroxy- or ω, represented by an integer of ~11
-acyloxy-alkyl-γ-butyrolactone can be obtained. Specific examples of such compounds of formula (2) include the following ω-hydroxy- or ω-acyloxy-alkyl-γ-butyrolactones.

When R=H; ω-hydroxy-pentyl-,
-hexyl-, -heptyl-, -octyl-, -nonyl-, -decyl-, -undecyl-, -dodecyl-, -tridecyl-, -tetradecyl-, -pentadecyl-, -hexadecyl-, -heptadecyl-,
-octadecyl-, -nonadecyl-γ-butyrolactone, when R=acetoxy; ω-acetyl-
Alkyl (same as above)-γ-butyrolactone, when R=propoxy; ω-propionyl (or -propionoxy)-alkyl (same as above)-γ-butyrolactone, when R=butyloxy; ω-butyroyl (or -butyronoxy)-alkyl (same as above example) -γ-butyrolactone, when R = pivaloxy; ω-pivalonoxy-alkyl (same as above example) -γ-butyrolactone, when R = isobutyroxy; ω-isobutyroyl (or - isobutyronoxy)-alkyl (same as exemplified above)-γ-butyrolactone.

By catalytically reacting the ω-hydroxy- or ω-acyloxy-alkyl-γ-butyrolactone represented by the formula (2) obtained as above in the presence of a hydrogenolysis catalyst, the following formula
(1)', ROCH ₂ (CH ₂ ) _o CH ₂ CH ₂ CH ₂ COOH (1)' However, in the formula, R and n have the same meanings as above for formula (2), and the omega-hydroxy fatty acid represented by It can be easily obtained with high conversion rate and selectivity. For example, as a compound of formula (2), in formula (2) obtained from diols of formula (3) and a compound of formula (4), R is hydrogen, and ω-hydroxy-alkyl-γ-butyrolactone is used. However, in the compound of formula (2),
It is preferable to use a compound in which R is an acyl group. The reaction can be carried out in the presence of a hydrogen cracking catalyst in which hydrogen gas coexists.
The use of group metal-based hydrogenolysis catalysts is preferred. Examples of such metals include palladium and platinum. These metal catalysts are preferably used in combination with carriers or co-catalysts such as cation exchange resins, solid acids such as zeolite; liquid acids such as phosphoric acid, polyphosphoric acid, and para-toluenesulfonic acid. It can be supported on solid acids such as. Furthermore, silica gel and silica-alumina gel can also be mentioned.

Examples of such hydrogenolysis catalysts include zeolite-palladium catalyst, palladium-carbon-
Examples include a cation exchange resin catalyst, a zeolite-bratina catalyst, and a platinum black cation exchange resin catalyst.

The reaction may be carried out by catalytically reacting the butyrolactones of formula (2) in the presence of a hydrogen cracking catalyst as exemplified above and in the coexistence of hydrogen gas. For the reaction, aliphatic and aromatic alcohols, fatty acids, aromatic acids, hydrocarbons, and mixtures of these solvents and water can be used. Furthermore, ketones which are hydrogenated in the reaction system and converted into the above-mentioned alcohols can also be used. A mixture of alcohol, alcohol-water, and especially isopropyl alcohol and water is preferred.

The reaction can be carried out, for example, at about 50° to about 250°C, preferably about 100° to about 200°C, more preferably about 130° to about 170°C. The reaction can be carried out under atmospheric or pressurized conditions, but
It is preferable to use pressurized conditions, for example, about 2 to about 150
Kg/cm ² , more preferably about 10 to about 80 Kg/cm ² .

The reaction can be carried out either batchwise or continuously. The reaction can be either a liquid phase reaction or a gas phase reaction.

The omega-hydroxy fatty acids obtained as described above, such as 15-hydroxy-pentadecanoic acid and 16-hydroxy-hexadecanoic acid, can be prepared, for example, according to the method of Japanese Patent Publication No. 41-7770 and Japanese Patent Application Laid-open No. 48-28488. It can be easily and in good yield converted into the aromatic substances cyclopentadecanolide and cyclohexadecanolide, which are very useful as perfume compounds.

Example 1 [Production example of compound of formula (2)] 500 g (3.13 mole) of 1.9 nonanediol was added to 1
Pour into a three-necked flask and stir to dissolve.
Methyl acrylate 26.8gr at 160-170℃
(0.312mole), n-butyl ether 26.8gr, di-
t-butyl peroxide (DTBP) 4.6gr
(0.0312 mole) of the mixed solution was added dropwise over 5 and a half hours.
After the dropwise addition was completed, the reaction was continued for 1 hour, and the reaction product was distilled. 1.9 nonanediol 450g (bp147-148
℃/1 mmHg) and the reaction product ω-hydroxyoctyl-γ-butyrolactone 45g
(bp195℃/1mmHg). Yield 68.5% versus methyl acrylate.

Example 2 [Production example of compound of formula (2)] 1,12-dodecanediol 1010g (5.0mole)
43.0g (0.5mole) and 7.3g of methyl acrylate are dissolved and heated to 160℃ with stirring.
A mixture of di-t-butyl peroxide (DTBP) (0.05 mole) and 43.0 g of decalin was added dropwise for 5 hours and 30 minutes. At the end point of dropping, the internal temperature is 145
℃. After the completion of the dropwise addition, the reaction is carried out at 140 to 160°C for 1 hour. The reaction product was collected by rectification to obtain 900 gr of 1,12-dodecanediol (bp 184-185°C/1 mmHg) and 102.3 g of ω-hydroxyundecyl-γ-butyrolactone (bp 217°C/1 mmHg mp 61.5°C).
Yield 81% versus methyl acrylate.

Example 3 [Production example of formula (2) compound] 1,13-tridecanediol 1070g
(5.0 mole), 43 g of methyl acrylate, di-t-
A mixed solution of 7.3 g of butyl peroxide (DTBP) and 43.0 g of decalin was reacted in the same manner as in Example 2 to obtain ω-hydroxydodecyl-γ-butyrolactone (bp 227°C/1 mmHg) in a yield of 77% vs. methyl acrylate. .

Example 4 [Production example of compound of formula (2)] 25 g (0.0977 mol) of ω-hydroxyundecyl-γ-butyrolactone and 40 dlg of acetic anhydride
(0.39215 mol) mixture at 115-120℃
It reacted for 6 hours. After the reaction was completed, treatment was carried out in a conventional manner to obtain 29.5 gr of ω-acetyl undecyl-γ-butyrolactone (mp 36.6°C). Yield 98.5%.

Example 5 [Production example of compound of formula (2)] A mixed solution of 25 g (0.0977 mol) of ω-hydroxyundecyl-γ-butyrolactone and 38.1 gr (0.293 mol) of butyric anhydride was reacted at 120° C. for 5 hours with stirring.
After the reaction is completed, 33.5g of ω-butyroylundecyl-γ-butyrolactone is obtained by processing in a conventional manner.
(mp24.5℃) was obtained. Yield 99.0%.

Example 6 [Production example of compound of formula (2)] 25 g (0.0977 mol) of ω-hydroxy-undecyl-γ-butyrolactone and 19.9 gr of pivalic acid
(0.1954 mol) in benzene 100cc.
Azeotropic dehydration was carried out for 5 hours using 3 drops of concentrated sulfuric acid as a catalyst. After the reaction was completed, unreacted pivalic acid was sufficiently removed with an aqueous sodium carbonate solution, neutralized by washing with water, and treated in a conventional manner to obtain 34.1 g (mp 34.7°C) of ω-pivalonoxyundecyl-γ-butyrolactone. . yield
98.6%.

Example 7 [Production example of compound of formula (2)] ω-hydroxydodecyl-γ-butyrolactone
Using 26.4 g (0.0977 mol) and 40 g (0.39215 mol) of acetic anhydride, 30.0 g of ω-acetyldodecyl-γ-butyrolactone was obtained, yield:
Got it at 98%.

Example 8 [Production example of compound of formula (2)] ω-hydroxydodecyl-γ-butyrolactone
30.0g (0.0977mol) and 20gr of n-valeric acid
(0.195 mol) was reacted in the same manner as in Example 6 to obtain 35.3 gr of ω-valeronoxy-dodecyl-γ-butyrolactone. Yield 98.3%.

Reference example 1 [Preparation example of hydrogenolysis catalyst] NaY type zeolite 50gr, ammonium nitrate
Put 14.42gr and 1800gr of ion-exchanged water into two three-necked flasks and ion-exchange at 70-80℃ for 30 minutes with stirring. After completion, the precipitate is washed with 2000 g of ion-exchanged water. This ion exchange cleaning operation is repeated two more times. For the final wash, use 3000g of ion-exchanged water. After washing, dry at room temperature and then at 125°C for 5 hours. This yielded 45 g of ion-exchanged zeolite. Put 45g of this zeolite and 225.0g of ion-exchanged water into a flask, and add palladium chloride.
Dissolve 0.753 g in 6 ml of 28% ammonia water, dilute with 45 ml of ion-exchanged water, pour the solution at 30°C, stir at the same temperature for 1 hour, and let it adhere.The precipitate is filtered and thoroughly washed with ion-exchanged water. After drying for 5 hours at 350℃
It was baked at ~400°C for 9 hours. Thereafter, the mixture was activated at 450 to 500°C for 10 hours under a hydrogen stream to obtain 40 g of a PdHY type zeolite catalyst. This is referred to as a ()PdHY type zeolite catalyst.

Reference Example 2 [Preparation Example of Hydrogenolysis Catalyst] In the same manner as in Reference Example 1, a catalyst prepared by adding palladium chloride and then calcining it at 350 to 400°C for 9 hours can be used as a catalyst. this()
A PdHY type zeolite catalyst was used.

Reference Example 3 [Preparation Example of Hydrogenolysis Catalyst] 40 g of ion-exchanged zeolite obtained in the same manner as Reference Example 1 and 200 ml of ion-exchanged water were placed in a flask, and Pt(NH ₃ ) ₄ Cl ₂ H ₂ O 1.2 A solution prepared by dissolving 260 g of ion-exchanged water was subjected to a dropwise adhesion reaction while stirring for 10 to 12 hours. The adhered slurry was filtered and washed with ion-exchanged water, then dried at 125°C and fired at 350-400°C. Thereafter, the PtHY type zeolite catalyst was obtained by activating it at 450 to 500°C for 10 hours under a hydrogen stream.

Reference Example 4 [Production example of compound of formula (1)] 20 g (0.0781 mol) of ω-hydroxyundecyl-γ-butyrolactone, 1.0 g of ()PdHY type zeolite catalyst, and 1.5 g of 80% isopropanol (containing 20% water) Charge into autoclave, initial pressure of hydrogen
Hydrogenolysis was carried out at 66.1 Kg/cm ² and a reaction temperature of 158 to 160° C. for 3 hours. After the reaction was completed, the catalyst was filtered to obtain 20 g of reaction oil.

As a result of GLC quantification of the reaction oil, 1.1 g (0.0045 mol) of pentadecanoic acid, 4.5 g (0.0187 mol) of γ-pentadecanoic acid, 10.9 g (0.0422 mol) of 15-hydroxypentadecanoic acid, and unreacted ω-hydroxyundecyl- γ-butyrolactone 2.9g
(0.0011 mol) was obtained.

Conversion rate (0.0045+0.0187+0.0422/
0.0781×100) = 83.7% Selectivity (0.0422/0.0781-0.011×10
0)=62.9% Therefore, the yield of 15-hydroxypentadecanoic acid is 62.9% based on ω-hydroxyundecyl-γ-butyrolactone.

Reference Example 5 [Production example of compound of formula (1)] 20 g (0.0781 mol) of ω-hydroxyundecyl-γ-butyrolactone, PtHY type zeolite, and catalyst
1.2g, 80% isopropanol (contains 20% water)
As a result of reacting in the same manner as in Reference Example 4 using 1.5 g,
The conversion rate of 15-hydroxypentadecanoic acid was 80.7%, and the selectivity was 60.3%.

Reference example 6 [Production example of compound of formula (1)] ω-acetyl undecyl-γ-butyrolactone
29.5 g (0.0962 mol), (1) 1.24 g of PdHY type zeolite catalyst, and 1.9 g of 80% isopropanol (containing 20% water) were charged into an autoclave, and the initial pressure of hydrogen was increased.
Hydrogenolysis is carried out at 60Kg/cm ² and a reaction temperature of 144-156°C for 3.5 hours. After the reaction was completed, the catalyst was filtered and treated in a conventional manner to obtain 28.6 g of a reaction product. Its composition is 0.3g (0.0011 mol) of pentadecanoic acid, 1.7g (0.007 mol) of γ-undecylbutyrolactone, 25.2g (0.0841 mol) of 15-acetylpentadecanoic acid, and 25.2g (0.0841 mol) of unreacted ω-acetylundecyl-γ-butyrolactone.
1.2 g (0.0039 mol) was obtained.

Conversion rate (0.0011+0.007+0.0841/0
．． 09622×100)) = 95.8% Selectivity (0.0841/0.09622-0.0039
5 x 100) = 91.1% In other words, the yield of 15-acetylpentadecanoic acid is 91.1% based on the consumed ω-acetylundecyl-γ-butyrolactone, and the target ω-hydroxypentadecanoic acid is obtained by a conventional method. It can be obtained by hydrolysis.

Reference Example 7 [Production example of compound of formula (1)] 29.5 g (0.0962 mol) of ω-acetyl undecyl-γ-butyrolactone, 1.3 g of ()PdHY type zeolite catalyst, 1.9 g of 80% isopropanol (containing 20% water) The conversion rate to 15-acetylpentadecanoic acid was 93.0 by reacting in the same manner as in Reference Example 6 using
%, and the selection rate was 87.0%.

Reference example 8 [Production example of compound of formula (1)] ω-acetyl undecyl-γ-butyrolactone
30.0g (0.0978mol) and PtHY type zeolite catalyst
As a result of the reaction in the same manner as in Reference Example 6 using 1.2 g of 80% isopropanol (containing 20% water), the conversion rate to 15-acetylpentadecanoic acid was 96.
%, and the selection rate was 89.2%.

Reference Example 9 [Production example of compound of formula (1)] 29.0 g (0.089 mol) of ω-butyroyl undecyl-γ-butyrolactone, 1.0 g of ()PdHY zeolite catalyst, and 2.0 g of 80% isopropanol (containing 20% water) React in the same manner as in Reference Example 6 using g,
Analysis of the product showed a conversion rate of 72% and a selectivity of 75%.

Reference example 10 [Production example of compound of formula (1)] 30.0 g (0.088 mol) of ω-pivalonoxyundecyl-γ-butyrolactone, 1.0 g of ()PdHY zeolite catalyst, and 2.0 g of 80% isopropanol (containing 20% water) The reaction was carried out in the same manner as in Reference Example 6 using g, and the analysis results of the product showed that the conversion rate was 70% and the selectivity was 80%.

Reference example 11 [Production example of compound of formula (1)] 29.0 g (0.089 mol) of ω-butyroyl undecyl-γ-butyrolactone and PtHY type zeolite catalyst
A reaction was carried out in the same manner as in Reference Example 6 using 1.0 g of 80% isopropanol (containing 20% water), and the product analysis results showed that the conversion rate of the target product ω-butyroylpentadecanoic acid was 80%. The rate was 70%.

Reference example 12 [Production example of compound of formula (1)] 30.0 g (0.088 mol) of ω-pivalonoxyundecyl-γ-butyrolactone, 1.0 g of PdHY type zeolite catalyst, 2.0 g of 80% isopropanol (contains 20% water) As a result of the reaction using g in the same manner as in Reference Example 6, the desired product was obtained with a conversion rate of 82% and a selectivity of 78%.
It was hot.

Reference example 13 [Production example of compound of formula (1)] ω-acetyl undecyl-γ-butyrolactone
23.9 g (0.0788 mol), 1.0 g of 5% Pd-C, 1.5 g of cation exchange resin (Amberlyst 15), and 1.5 g of 80% isopropanol (containing 20% water) were placed in an autoclave, and the initial pressure of hydrogen was 63.5 Kg. /cm ² and a reaction temperature of 134 to 144° C. for 5 hours. After the reaction was completed, the catalyst was filtered and treated in a conventional manner to obtain 24 g of a reaction product.

Its composition is 0.4 g (0.0016 mol) of pentadecanoic acid, 0.9 g (0.0036 mol) of γ-pentadecalactone, and 18.8 g of 15-acetylpentadecanoic acid.
(0.0626 mol), unreacted ω-acetyl undecyl-
The amount of γ-butyrolactone was 3.0 g (0.0099 mol).

Conversion rate (0.0016+0.0036+0.0626/
0.0788×100) = 86.0% Selectivity (0.0626/0.0788-0.0099×
100)=90.9% That is, the yield of 15-acetylpentadecanoic acid from consumed ω-acetylundecyl-γ-butyrolactone is 92.3%.

Reference example 14 [Production example of compound of formula (1)] ω-acetyldodecyl-γ-butyrolactone
30.2 g (0.0953 mol), 1.3 g of PdHY type zeolite catalyst, and 1.9 g of 80% isopropanol (containing 20% water) were charged into an autoclave, and the initial hydrogen pressure was 65 Kg/cm ² and the reaction temperature was 144 to 157°C. Hydrogenolyzed for hours.

After the reaction was completed, the catalyst was filtered and treated in a conventional manner to obtain 30 g of a reaction product. Its composition is 0.8 g (0.003 mol) of hexadecanoic acid, γ-hexadecalactone
1.8 g (0.0071 mol), 24.5 g (0.0779 mol) of 16-acetylhexadecanoic acid, and 2.3 g (0.0073 mol) of unreacted ω-acetyldodecyl-γ-butyrolactone were obtained.

Conversion rate (0.003+0.0071+0.0779/0
．． 0953×100) =92.3% Selectivity (0.0779/0.0953-0.0073×
100)=88.5% That is, the yield of 16-acetylhexadecanoic acid based on the consumed ω-acetyldodecyl-γ-butyrolactone is 88.5%.

Claims (1)

[Claims] 1. The following formula (2) However, in the formula, R represents hydrogen or an acyl group derived from a _C1 to _C10 aliphatic monocarboxylic acid, and n represents an integer of 4 to 18. ω-hydroxy- or ω-acyloxy- Alkyl-γ-butyrolactone. 2 The following formula (3) HOCH ₂ (CH ₂ ) _o CH ₂ OH (3) However, in the formula, n represents an integer from 4 to 18. A diol represented by the following formula (4) CH ₂ =CHCOOR' ( 4) In the formula (2) below, R' represents hydrogen or an alkyl group, which is characterized by reacting acrylic acid or its alkyl ester represented by in the presence of a radical catalyst. However, in the formula, R represents hydrogen or an acyl group derived from a _C1 to _C10 aliphatic monocarboxylic acid, and n represents an integer of 4 to 18. ω-hydroxy- or ω-acyloxy- Method for producing alkyl-γ-butyrolactone.