JPH05155806A - Production of metallic salt of fatty acid - Google Patents
Production of metallic salt of fatty acidInfo
- Publication number
- JPH05155806A JPH05155806A JP34404191A JP34404191A JPH05155806A JP H05155806 A JPH05155806 A JP H05155806A JP 34404191 A JP34404191 A JP 34404191A JP 34404191 A JP34404191 A JP 34404191A JP H05155806 A JPH05155806 A JP H05155806A
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- weight
- water
- parts
- metallic salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明はアルカリ金属塩以外の脂
肪酸金属塩(以下、単に脂肪酸金属塩という)の製造法
に関し、詳しくはヨウ素価100以上の脂肪酸を原料と
して、酸化劣化の少ない粉末または顆粒状の脂肪酸金属
塩の製造法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing a fatty acid metal salt (hereinafter simply referred to as a fatty acid metal salt) other than an alkali metal salt. The present invention relates to a method for producing a granular fatty acid metal salt.
【0002】[0002]
【従来の技術】脂肪酸金属塩の製造法としては、脂肪酸
と金属化合物を直接高温で融解反応させる直接溶融法、
脂肪酸ナトリウム塩の水溶液に無機金属塩の水溶液を加
えて、金属石鹸を遊離させる複分解法が広く採用されて
いる。しかし、これらの方法では反応時に加熱が必要で
あり、ヨウ素価100以上の脂肪酸を原料として使用す
る場合には、加熱により脂肪酸の酸化劣化が起こる。2. Description of the Related Art As a method for producing a fatty acid metal salt, a direct melting method in which a fatty acid and a metal compound are directly subjected to a melting reaction at a high temperature,
A metathesis method in which an aqueous solution of an inorganic metal salt is added to an aqueous solution of a fatty acid sodium salt to release metallic soap is widely adopted. However, these methods require heating during the reaction, and when a fatty acid having an iodine value of 100 or more is used as a raw material, the heating causes oxidative deterioration of the fatty acid.
【0003】低温で脂肪酸金属塩を製造する方法として
は、特公昭61−20275号公報に、油脂を金属水酸
化物の存在下において、リパーゼで分解することによ
り、脂肪酸金属塩を製造する方法が、特公昭60−12
337号公報には、脂肪酸に金属酸化物または金属水酸
化物を分散させた後、水を添加し、反応させることによ
り、脂肪酸金属塩を製造する方法が、また、特開昭54
−154709号公報には、金属水酸化物の水溶液また
は懸濁液と脂肪酸とを融点以下の温度で、攪拌しながら
反応させたのち、脂肪酸の融点以上の温度で反応させて
脂肪酸金属塩を製造する方法が提案されている。As a method for producing a fatty acid metal salt at low temperature, Japanese Patent Publication No. 61-20275 discloses a method for producing a fatty acid metal salt by decomposing fats and oils with lipase in the presence of a metal hydroxide. , Japanese Sho 60-12
In Japanese Patent No. 337, a method for producing a fatty acid metal salt by dispersing a metal oxide or a metal hydroxide in a fatty acid, and then adding water thereto and reacting the mixture is also disclosed.
JP-A-154709 discloses that a fatty acid metal salt is produced by reacting an aqueous solution or suspension of a metal hydroxide with a fatty acid at a temperature equal to or lower than the melting point while stirring and then reacting at a temperature equal to or higher than the melting point of the fatty acid. The method to do is proposed.
【0004】[0004]
【発明が解決しようとする課題】特公昭61−2027
5号公報による方法では、反応が完結するまでに長時間
を要し、また反応に酵素を用いるので、製造コストが高
くなる。特公昭60−12337号公報および特開昭5
4−154709号公報による方法では、原料として、
ヨウ素価100以上の脂肪酸を用いた場合、反応に長い
時間を要するあるいは高温、高圧などの反応条件が必要
であり、脂肪酸の酸化劣化を招いたり、反応生成物が反
応系内で凝集を起こし、均一な製品が得られないなどの
問題がある。本発明は、原料として用いるヨウ素価10
0以上の脂肪酸を酸化劣化させることなく、簡単な操作
で脂肪酸金属塩を製造する方法を提供すること目的とす
る。[Problems to be Solved by the Invention] Japanese Patent Publication No. 61-2027
In the method according to the publication No. 5, it takes a long time to complete the reaction and an enzyme is used for the reaction, so that the production cost becomes high. Japanese Examined Patent Publication No. 60-12337 and Japanese Patent Laid-Open No. Sho 5
In the method according to 4-154709, as raw materials,
When a fatty acid having an iodine value of 100 or more is used, it takes a long time for the reaction or reaction conditions such as high temperature and high pressure are required, which leads to oxidative deterioration of the fatty acid, and the reaction product causes aggregation in the reaction system. There is a problem that a uniform product cannot be obtained. The present invention uses an iodine value of 10 as a raw material.
An object of the present invention is to provide a method for producing a fatty acid metal salt by a simple operation without oxidative deterioration of 0 or more fatty acids.
【0005】[0005]
【課題を解決するための手段】すなわち、本発明はヨウ
素価100以上の脂肪酸を、脂肪酸の1〜2.8当量比
のアルカリ金属以外の金属水酸化物を脂肪酸の重量の4
倍以上の水に分散した分散液に添加し、脂肪酸の融点よ
り1〜20℃高い温度で反応させることを特徴とする脂
肪酸金属塩の製造法である。That is, according to the present invention, a fatty acid having an iodine value of 100 or more is used, and a metal hydroxide other than an alkali metal in a ratio of 1 to 2.8 equivalent of the fatty acid is used in an amount of 4% by weight of the fatty acid.
It is a method for producing a fatty acid metal salt, characterized in that the fatty acid metal salt is added to a dispersion liquid that is twice or more the amount of water and reacted at a temperature 1 to 20 ° C. higher than the melting point of the fatty acid.
【0006】本発明に用いるヨウ素価100以上の脂肪
酸としては、リノール酸、リノレン酸などの脂肪酸のほ
か、大豆油、アマニ油、シソ油、キリ油などの植物性油
脂、またはイワシ油、サバ油、サメ肝油、タラ肝油、鯨
油などの水産動物油脂を加水分解して得た脂肪酸などが
挙げられ、これらの単独または2種以上の混合脂肪酸を
用いることができる。また、脂肪酸は油脂を含有しても
良いが、油脂含量が35重量%を超えると凝集物が生成
して好ましくない。Examples of the fatty acid having an iodine value of 100 or more used in the present invention include fatty acids such as linoleic acid and linolenic acid, vegetable oils such as soybean oil, linseed oil, perilla oil, and tung oil, or sardine oil and mackerel oil. Examples thereof include fatty acids obtained by hydrolyzing aquatic animal fats and oils such as shark liver oil, cod liver oil, and whale oil. These fatty acids may be used alone or in combination of two or more. The fatty acid may contain fats and oils, but if the fats and oils content exceeds 35% by weight, agglomerates are formed, which is not preferable.
【0007】本発明に用いるアルカリ金属以外の金属水
酸化物としては、水酸化カルシウム、水酸化マグネシウ
ム、水酸化バリウム、水酸化亜鉛などが挙げられ、これ
らの単独または2種以上の混合物を用いることができ
る。この金属水酸化物は脂肪酸に対し1〜2.8当量を
用いるが、1当量未満では未反応脂肪酸が多くなり、凝
集物が生成する。2.8当量を超えると未反応水酸化物
が多くなり好ましくない。Examples of the metal hydroxide other than the alkali metal used in the present invention include calcium hydroxide, magnesium hydroxide, barium hydroxide, zinc hydroxide and the like, and these may be used alone or in a mixture of two or more kinds. You can This metal hydroxide is used in an amount of 1 to 2.8 equivalents with respect to the fatty acid, but if it is less than 1 equivalent, the amount of unreacted fatty acid increases and aggregates are formed. If it exceeds 2.8 equivalents, unreacted hydroxide increases, which is not preferable.
【0008】この金属水酸化物を分散させる水の量は、
脂肪酸の4重量倍以上である。水の量が4重量倍未満で
は、反応生成物が反応系内で凝集を起こし易くなる。水
の量の上限はとくに限定はないが、多くなると生産効率
が低くなる。The amount of water in which this metal hydroxide is dispersed is
It is more than 4 times the weight of fatty acids. When the amount of water is less than 4 times by weight, the reaction product easily aggregates in the reaction system. The upper limit of the amount of water is not particularly limited, but the production efficiency decreases as the amount increases.
【0009】反応温度は、原料脂肪酸の融点より1〜2
0℃高い温度であり、1℃未満では反応が進まない。2
0℃を超えると、脂肪酸の酸化劣化が起こり、また生成
した脂肪酸金属塩が凝集を起こすので、好ましくない。The reaction temperature is 1 to 2 above the melting point of the raw material fatty acid.
The temperature is higher by 0 ° C, and the reaction does not proceed below 1 ° C. Two
If the temperature exceeds 0 ° C, oxidative deterioration of fatty acids will occur, and the produced fatty acid metal salt will agglomerate, which is not preferable.
【0010】脂肪酸を添加する方法は、特に限定はない
が、この金属水酸化物の分散液を攪拌しながら、脂肪酸
を滴下または噴霧するのが好ましい。The method of adding the fatty acid is not particularly limited, but it is preferable to add or drop the fatty acid while stirring the dispersion of the metal hydroxide.
【0011】[0011]
【発明の効果】本発明によれば、ヨウ素価100以上の
脂肪酸を酸化劣化することなく、簡単な操作で粉末また
は顆粒状の脂肪酸金属塩を製造することができる。さら
に、本発明により得られる脂肪酸金属塩は酸化劣化を受
けてないので養魚用飼料、家畜用飼料などの用途に利用
できる。According to the present invention, a powdery or granular fatty acid metal salt can be produced by a simple operation without oxidative deterioration of a fatty acid having an iodine value of 100 or more. Furthermore, since the fatty acid metal salt obtained by the present invention has not been subjected to oxidative deterioration, it can be used for fish feed, livestock feed and the like.
【0012】[0012]
【実施例】以下、実施例により本発明を具体的に説明す
る。尚、ΔPOVは製造した脂肪酸金属塩の過酸化物価
と原料脂肪酸の過酸化物価との差である。EXAMPLES The present invention will be specifically described below with reference to examples. Incidentally, ΔPOV is the difference between the peroxide value of the fatty acid metal salt produced and the peroxide value of the raw material fatty acid.
【0013】実施例1 水酸化カルシウム55重量部(脂肪酸の1.4当量比)
を水2000重量部に分散させ、この分散液を10℃に
保ち、600rpmで攪拌しながら、リノール酸(純
度:95重量%、ヨウ素価:175.6,融点:−1.
2℃)300重量部を分散液に1時間かけて均等に噴霧
したのち同温度で30分間保った。そののち濾過、水洗
をして、30℃,0.1mmHgで3時間真空乾燥し
て、水分2.0重量%,遊離脂肪酸0.8重量%、ΔP
OV0.1の白色粉末296重量部を得た。Example 1 55 parts by weight of calcium hydroxide (1.4 equivalent ratio of fatty acid)
Of linoleic acid (purity: 95% by weight, iodine value: 175.6, melting point: -1.
300 parts by weight (2 ° C.) was evenly sprayed onto the dispersion over 1 hour, and then kept at the same temperature for 30 minutes. After that, it is filtered, washed with water, and dried in vacuum at 30 ° C. and 0.1 mmHg for 3 hours to obtain a water content of 2.0% by weight, a free fatty acid of 0.8% by weight, and a ΔP.
296 parts by weight of OV 0.1 white powder was obtained.
【0014】実施例2 水酸化カルシウム62重量部(脂肪酸の1.68当量
比)を水2500重量部に分散させ、この分散液を25
℃に保ち、450rpmで攪拌しながら、大豆油脂肪酸
(ヨウ素価:120.7,融点:19.5℃,油脂含量
6.8重量%)300重量部を分散液に30分間かけて
均等に滴下したのち同温度で1時間保った。そののち濾
過、遠心脱水をして、室温で24時間風乾して、水分
5.9重量%,遊離脂肪酸1.9重量%、ΔPOV0.
2の白色顆粒272重量部を得た。Example 2 62 parts by weight of calcium hydroxide (1.68 equivalent ratio of fatty acid) was dispersed in 2500 parts by weight of water.
While maintaining the temperature at 450 ° C. and stirring at 450 rpm, 300 parts by weight of soybean oil fatty acid (iodine value: 120.7, melting point: 19.5 ° C., fat and oil content of 6.8% by weight) was uniformly added dropwise to the dispersion liquid over 30 minutes. After that, it was kept at the same temperature for 1 hour. After that, filtration, centrifugal dehydration, and air drying at room temperature for 24 hours, water 5.9% by weight, free fatty acid 1.9% by weight, ΔPOV0.
272 parts by weight of white granules of No. 2 were obtained.
【0015】実施例3 水酸化カルシウム79重量部(脂肪酸の2.68当量
比)を水3000重量部に分散させ、この分散液を30
℃に保ち、800rpmで攪拌しながら、スケソウタラ
肝油を酵素分解して得た脂肪酸(ヨウ素価:154.
2,融点:21.4℃,油脂含量23.5重量%)30
0重量部を分散液に1時間かけて均等に滴下したのち同
温度で1時間保った。そののち濾過をして、水分28.
1重量%,遊離脂肪酸2.0重量%、ΔPOV0.3の
黄色顆粒422重量部を得た。Example 3 79 parts by weight of calcium hydroxide (2.68 equivalent ratio of fatty acid) was dispersed in 3000 parts by weight of water, and 30 parts of this dispersion was used.
Maintained at 800 ° C. and stirred at 800 rpm, a fatty acid (iodine value: 154.
2, melting point: 21.4 ° C., fat content 23.5% by weight) 30
0 part by weight was uniformly added dropwise to the dispersion over 1 hour, and the mixture was kept at the same temperature for 1 hour. After that, it is filtered to remove water 28.
422 parts by weight of yellow granules of 1% by weight, free fatty acid 2.0% by weight, and ΔPOV 0.3 were obtained.
【0016】実施例4 水酸化カルシウム48重量部,水酸化マグネシウム20
重量部(脂肪酸の2.05当量比)を水2700重量部
に分散させ、この分散液を20℃に保ち、650rpm
で攪拌しながら、大豆油を酵素分解して得た脂肪酸15
0重量部とシソ油を酵素分解して得た脂肪酸150重量
部の混合物(ヨウ素価:201.1,融点:12.6
℃,油脂含量9.7重量%)を分散液に1時間かけて均
等に滴下したのち同温度で1時間保った。そののち濾
過、圧搾脱水をして、窒素気流下、35℃で8時間通風
乾燥して、水分3.1重量%,遊離脂肪酸0.9重量
%、ΔPOV0.2の白色顆粒253重量部を得た。Example 4 48 parts by weight of calcium hydroxide and 20 parts of magnesium hydroxide
Parts by weight (2.05 equivalent ratio of fatty acid) are dispersed in 2700 parts by weight of water, and the dispersion is kept at 20 ° C. and 650 rpm.
Fatty acid obtained by enzymatic decomposition of soybean oil while stirring at 15
A mixture of 0 parts by weight and 150 parts by weight of a fatty acid obtained by enzymatically decomposing perilla oil (iodine value: 201.1, melting point: 12.6
(° C, fat and oil content of 9.7% by weight) was uniformly added dropwise to the dispersion over 1 hour, and the mixture was kept at the same temperature for 1 hour. After that, filtration, compression dehydration, and ventilation drying at 35 ° C. for 8 hours under a nitrogen stream are performed to obtain 253 parts by weight of white granules having a water content of 3.1% by weight, free fatty acids of 0.9% by weight, and ΔPOV of 0.2. It was
【0017】比較例1 分散液の温度80℃にした以外は実施例2と同じ条件で
行った。脂肪酸滴下終了後、反応混合物の凝集が起こり
攪拌が困難になった。凝集物の遊離脂肪酸13.5重量
%、ΔPOV17.8であり、未反応脂肪酸が多く、酸
化劣化の程度も大であった。Comparative Example 1 The same conditions as in Example 2 were used except that the temperature of the dispersion liquid was 80 ° C. After the dropwise addition of the fatty acid, the reaction mixture agglomerated and the stirring became difficult. The free fatty acid of the aggregate was 13.5% by weight, ΔPOV was 17.8, the amount of unreacted fatty acid was large, and the degree of oxidative deterioration was large.
【0018】比較例2 分散液の温度15℃にした以外は実施例3と同じ条件で
行った。脂肪酸滴下終了後、反応混合物の凝集が起こり
攪拌が困難になった。凝集物の遊離脂肪酸68.5重量
%、ΔPOV0.1であり、未反応脂肪酸が非常に多
く、反応はほとんど進んでいなかった。Comparative Example 2 The same conditions as in Example 3 were used except that the temperature of the dispersion liquid was set to 15 ° C. After the dropwise addition of the fatty acid, the reaction mixture agglomerated and the stirring became difficult. The free fatty acid of the aggregate was 68.5% by weight and ΔPOV was 0.1, the amount of unreacted fatty acid was very large, and the reaction was hardly progressed.
【0019】比較例3 スケソウタラ肝油(ヨウ素価:150.3,凝固点:
9.8℃)500重量部を20重量%エタノール水溶液
500重量部に加え、600rpmで攪拌しながら30
重量%水酸化ナトリウム水溶液220重量部を徐々に加
えたのち、60℃で1時間保った。溶液の粘度が上昇し
たので、温水500重量部を加えたのち80℃にし、3
0重量%塩化カルシウム水溶液300重量部(脂肪酸の
1当量比)を均等に1時間かけて滴下したのち60℃で
1時間保った。瀘過、水洗、脱水し30℃、3時間減圧
乾燥して、水分4.5重量%、遊離脂肪酸4.8重量
%、ΔPOV19.7の黄褐色の一部凝集物を含む粉末
465重量部を得た。この製造法は操作が複雑であり、
また酸化劣化の程度も大であった。Comparative Example 3 Alaska pollack liver oil (iodine value: 150.3, freezing point:
(9.8 ° C.) 500 parts by weight to 500 parts by weight of a 20% by weight aqueous ethanol solution, and while stirring at 600 rpm, 30
After 220 parts by weight of an aqueous solution of sodium hydroxide in weight% was gradually added, the mixture was kept at 60 ° C. for 1 hour. Since the viscosity of the solution increased, add 500 parts by weight of warm water and then bring it to 80 ° C.
300 parts by weight of a 0% by weight calcium chloride aqueous solution (1 equivalent ratio of fatty acid) was added dropwise uniformly over 1 hour, and then the mixture was kept at 60 ° C. for 1 hour. After filtering, washing with water, dehydration, and drying under reduced pressure at 30 ° C. for 3 hours, 465 parts by weight of a powder containing 4.5% by weight of water, 4.8% by weight of free fatty acid and a yellowish brown partial agglomerate of ΔPOV19.7. Obtained. This manufacturing method is complicated to operate,
The degree of oxidative deterioration was also large.
Claims (1)
1〜2.8当量比のアルカリ金属以外の金属水酸化物を
脂肪酸の重量の4倍以上の水に分散した分散液に添加
し、脂肪酸の融点より1〜20℃高い温度で反応させる
ことを特徴とする脂肪酸金属塩の製造法。1. A fatty acid having an iodine value of 100 or more is added to a dispersion liquid in which a metal hydroxide other than an alkali metal in a 1 to 2.8 equivalent ratio of the fatty acid is dispersed in water which is 4 times or more the weight of the fatty acid, A method for producing a fatty acid metal salt, which comprises reacting at a temperature 1 to 20 ° C. higher than the melting point of the fatty acid.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP34404191A JPH05155806A (en) | 1991-12-03 | 1991-12-03 | Production of metallic salt of fatty acid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP34404191A JPH05155806A (en) | 1991-12-03 | 1991-12-03 | Production of metallic salt of fatty acid |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH05155806A true JPH05155806A (en) | 1993-06-22 |
Family
ID=18366206
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP34404191A Pending JPH05155806A (en) | 1991-12-03 | 1991-12-03 | Production of metallic salt of fatty acid |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH05155806A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2006160920A (en) * | 2004-12-08 | 2006-06-22 | San Nopco Ltd | Fatty acid metal salt composition |
JP2007314810A (en) * | 1994-12-28 | 2007-12-06 | Ciba Specialty Chem Holding Inc | Low-dust granule of plastic additive |
JP2012507505A (en) * | 2008-10-31 | 2012-03-29 | リピッド ファーマシューティカルズ イーエイチエフ. | Fatty acids for use as pharmaceuticals |
-
1991
- 1991-12-03 JP JP34404191A patent/JPH05155806A/en active Pending
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007314810A (en) * | 1994-12-28 | 2007-12-06 | Ciba Specialty Chem Holding Inc | Low-dust granule of plastic additive |
JP2006160920A (en) * | 2004-12-08 | 2006-06-22 | San Nopco Ltd | Fatty acid metal salt composition |
JP4608619B2 (en) * | 2004-12-08 | 2011-01-12 | サンノプコ株式会社 | Lubricant for coated paper |
JP2012507505A (en) * | 2008-10-31 | 2012-03-29 | リピッド ファーマシューティカルズ イーエイチエフ. | Fatty acids for use as pharmaceuticals |
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