JPS6253154B2 - - Google Patents
Info
- Publication number
- JPS6253154B2 JPS6253154B2 JP59262450A JP26245084A JPS6253154B2 JP S6253154 B2 JPS6253154 B2 JP S6253154B2 JP 59262450 A JP59262450 A JP 59262450A JP 26245084 A JP26245084 A JP 26245084A JP S6253154 B2 JPS6253154 B2 JP S6253154B2
- Authority
- JP
- Japan
- Prior art keywords
- castor oil
- hydrogenated castor
- lipase
- hydrolysis
- acid
- 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.)
- Expired
Links
- 239000004359 castor oil Substances 0.000 claims description 19
- 235000019438 castor oil Nutrition 0.000 claims description 19
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 19
- 239000004367 Lipase Substances 0.000 claims description 16
- 102000004882 Lipase Human genes 0.000 claims description 16
- 108090001060 Lipase Proteins 0.000 claims description 16
- 235000019421 lipase Nutrition 0.000 claims description 16
- VLHZUYUOEGBBJB-UHFFFAOYSA-N hydroxy stearic acid Natural products OCCCCCCCCCCCCCCCCCC(O)=O VLHZUYUOEGBBJB-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 244000005700 microbiome Species 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 10
- 230000007062 hydrolysis Effects 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000003925 fat Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 8
- 235000019197 fats Nutrition 0.000 description 7
- 238000007127 saponification reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 241000588881 Chromobacterium Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000010775 animal oil Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000010446 mirabilite Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 235000019871 vegetable fat Nutrition 0.000 description 2
- 238000004065 wastewater treatment Methods 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- DYBIGIADVHIODH-UHFFFAOYSA-N 2-nonylphenol;oxirane Chemical compound C1CO1.CCCCCCCCCC1=CC=CC=C1O DYBIGIADVHIODH-UHFFFAOYSA-N 0.000 description 1
- 241000588986 Alcaligenes Species 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000223198 Humicola Species 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- 241000235395 Mucor Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000235527 Rhizopus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、リパーゼによるオキシステアリン酸
の製造方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing oxystearic acid using lipase.
［従来の技術］
12−ヒドロキシステアリン酸は、硬化ヒマシ油
を鹸化分解して製造される。一般には硬化ヒマシ
油に同量の温水を加え、水酸化ナトリウム溶液を
加えて加温撹拌して鹸化分解する。次いで、硫酸
溶液を添加して中和し、95〜100℃で数十分間熟
成して得られる。[Prior Art] 12-hydroxystearic acid is produced by saponifying and decomposing hydrogenated castor oil. Generally, the same amount of hot water is added to hydrogenated castor oil, a sodium hydroxide solution is added, and the oil is heated and stirred for saponification and decomposition. Next, a sulfuric acid solution is added to neutralize the product, and the product is aged at 95 to 100°C for several tens of minutes.
12−ヒドロキシステアリン酸の鹸化分解による
製法は、多量の芒硝が副生すること、およびその
ために生成グリセリンが甘水として完全に回収出
来ず、廃水の処理等の二次的な問題が派生してく
る。また、一般の動植物油脂の加水分解に広く用
いられる高圧加水分解法では、かかる問題は生じ
ないが、オキシステアリン酸のトリグリセリドで
ある硬化ヒマシ油の場合は、高圧加水分解法に要
求される高温（180℃以上）では、エステリド化
や分子内脱水反応による二重結合生成が進行する
ため適用出来ない。 The production method using saponification and decomposition of 12-hydroxystearic acid produces a large amount of Glauber's salt as a by-product, and as a result, the glycerin produced cannot be completely recovered as sweet water, leading to secondary problems such as wastewater treatment. come. In addition, this problem does not occur with the high-pressure hydrolysis method that is widely used to hydrolyze general animal and vegetable oils and fats, but in the case of hydrogenated castor oil, which is a triglyceride of oxystearic acid, the high-temperature hydrolysis method required (180℃ or higher), it cannot be applied because double bond formation occurs due to esterification and intramolecular dehydration reactions.
リパーゼによる一般動植物油脂の加水分解につ
いては、これまでにも多くの提案がなされてい
る。しかしながら、リパーゼは一般には耐熱性の
点で高融点の油脂の分解には適用が難しく、動植
物油脂の中でも最も高い融点を有するとみられて
いる硬化ヒマシ油（融点85〜90℃）に適用出来る
ことを開示もしくは示唆した提案は認められな
い。特公昭46−28039号公報は、固体脂をリパー
ゼ水溶液と共に融解乳化させた後、乳化状態で冷
却させ、静置法により分解する方法であるが、硬
化ヒマシ油の場合は非常に高融点であるため、以
上の様な状態を形成出来ない。又、特開昭57−
57799号公報は、融解した脂肪と冷却したリパー
ゼ水溶液とを混合して脂肪の融点以下の安定な分
散液を得た後、この状態で脂肪を加水分解する方
法を提示したものである。しかしながら、いずれ
の方法も具体的には、最も高融点の基質にあつて
も、硬化ヒマシ油より低融点である牛脂（融点40
〜50℃）を対象にしたものにとどまり、硬化ヒマ
シ油に適用することは困難なものと考える。 Many proposals have been made so far regarding the hydrolysis of general animal and vegetable oils and fats by lipase. However, lipase is generally difficult to apply to decomposing fats and oils with high melting points due to its heat resistance, but it can be applied to hydrogenated castor oil (melting point 85-90℃), which is considered to have the highest melting point among animal and vegetable oils. Proposals that disclose or suggest that such matters will not be accepted. Japanese Patent Publication No. 46-28039 discloses a method in which a solid fat is melted and emulsified with an aqueous lipase solution, cooled in an emulsified state, and decomposed by a standing method, but hydrogenated castor oil has a very high melting point. Therefore, the above state cannot be formed. Also, JP-A-57-
Publication No. 57799 proposes a method of mixing molten fat and a cooled aqueous lipase solution to obtain a stable dispersion having a temperature below the melting point of the fat, and then hydrolyzing the fat in this state. However, in both methods, even though the substrate has the highest melting point, beef tallow (melting point 40
It is considered that it is difficult to apply it to hydrogenated castor oil.
［発明が解決しようとする問題点］
本発明者らは、係る状況下にあつてオキシステ
アリン酸の新規な製造法を確立すべく鋭意検討し
た中で、硬化ヒマシ油にリパーゼを作用させたと
ころ、驚くべきことに、特定の温度下において、
特別に油脂を溶融させることなく12−ヒドロキシ
ステアリン酸が生成されることを見い出し、本発
明を完成したものである。[Problems to be Solved by the Invention] Under the circumstances, the present inventors conducted intensive studies to establish a new method for producing oxystearic acid, and found that they caused lipase to act on hydrogenated castor oil. , surprisingly, at a certain temperature,
The present invention was completed by discovering that 12-hydroxystearic acid can be produced without specifically melting fats and oils.
即ち、本発明は、硬化ヒマシ油に微生物に由来
するリパーゼ及び水を加え、撹拌下、50℃以上で
加水分解することを特徴とする新規なオキシステ
アリン酸の製造方法を提供することを目的とす
る。 That is, an object of the present invention is to provide a novel method for producing oxystearic acid, which is characterized in that lipase derived from microorganisms and water are added to hydrogenated castor oil, and the mixture is hydrolyzed at 50°C or higher while stirring. do.
［問題点を解決するための手段］
本発明で用いられるリパーゼは、微生物に由来
するリパーゼである。好ましい微生物としては、
クロモバクテリウム属、リゾープス属、ムコール
属、シユードモナス属、フミコーラ属、アルカリ
ゲネス属等が例示される。[Means for Solving the Problems] The lipase used in the present invention is derived from a microorganism. Preferred microorganisms include
Examples include Chromobacterium, Rhizopus, Mucor, Pseudomonas, Humicola, and Alcaligenes.
加える酵素量は、リパーゼの種類により一概に
は言えないが、例えばクロモバクテリウム属起源
の細菌リパーゼ（東洋醸造(株)製：40万単位／ｇ）
の場合、硬化ヒマシ油に対して0.02〜0.2％、好
ましくは0.05〜0.1％である。0.02％より少ないと
加水分解速度が小さく、0.2％より多くても顕著
な効果の向上は認められない。 The amount of enzyme to be added cannot be generalized depending on the type of lipase, but for example, bacterial lipase originating from the genus Chromobacterium (manufactured by Toyo Jozo Co., Ltd.: 400,000 units/g)
0.02-0.2%, preferably 0.05-0.1% based on hydrogenated castor oil. If it is less than 0.02%, the hydrolysis rate will be low, and if it is more than 0.2%, no significant improvement in effect will be observed.
加水分解をするに際し添加する水の量は、油脂
に対して20〜400％、好ましくは50〜100％であ
る。少量の水を用いて反応を数回に分けて行なう
多段方式を用いても差しつかえない。 The amount of water added during hydrolysis is 20 to 400%, preferably 50 to 100%, based on the fat or oil. It is also possible to use a multistage method in which the reaction is carried out in several steps using a small amount of water.
反応温度は、50℃以上であれば足り、好ましく
は硬化ヒマシ油の融点以下の温度（60〜85℃）で
ある。 The reaction temperature may be 50°C or higher, preferably a temperature below the melting point of hydrogenated castor oil (60 to 85°C).
本発明を実施するに際して、水層へのカルシウ
ムイオン、マグネシウムイオン等の添加が効果的
である。 When carrying out the present invention, it is effective to add calcium ions, magnesium ions, etc. to the aqueous layer.
更には、促進剤として非イオン界面活性剤、特
に飽和もしくは不飽和の高級アルコール系あるい
はアルキルフエノール系のエチレオキシド付加体
の１種もしくは２種以上を、又は該活性剤と上記
の金属イオンとを併用すると効果的であるが必ず
しも使用する必要はない。 Furthermore, as a promoter, a nonionic surfactant, especially one or more saturated or unsaturated higher alcohol-based or alkylphenol-based ethylene oxide adducts, or the surfactant and the above-mentioned metal ions may be used. Although it is effective when used together, it is not necessary to use them together.
以上の方法に従い加水分解反応を行なうと、反
応初期においては硬化ヒマシ油は固体のままであ
るが、反応の進行に伴つて軟化し、次いで、液化
し、通常の加水分解と同様な状態となる。例えば
反応温度が75℃の場合、分解率が40％を越えた付
近から液化が認められる。 When the hydrolysis reaction is carried out according to the above method, the hydrogenated castor oil remains solid at the initial stage of the reaction, but as the reaction progresses, it softens and then liquefies, resulting in a state similar to that of normal hydrolysis. . For example, when the reaction temperature is 75°C, liquefaction is observed when the decomposition rate exceeds 40%.
従つて、本発明方法においては、硬化ヒマシ油
を市販の形状のままで使用でき、又、基質とリパ
ーゼとの接触界面を増大させもしくは安定化させ
るために乳化する必要もない。 Therefore, in the method of the present invention, hydrogenated castor oil can be used in its commercially available form, and there is no need to emulsify it to increase or stabilize the contact interface between the substrate and lipase.
［実施例］ 以下に実施例を掲げ、本発明を詳説する。[Example] The present invention will be explained in detail with reference to Examples below.
実施例 １
硬化ヒマシ油200ｇ、東洋醸造(株)製の
Chromobacterium viscom var.paralipotica起源
の細菌リパーゼ（40万単位／ｇ）0.1ｇ（硬化ヒ
マシ油に対し0.05％）及び水200ml（硬化ヒマシ
油に対し100％）を反応器に仕込み、75℃に保ち
ながら500rpmの撹拌下、48時間加水分解反応を
行なつた。リパーゼを含む水層を分離して得られ
た12−ヒドロキシステアリン酸の性状は以下の通
りである。酸価153、鹸化価184、水酸基価158、
沃素価1.2、分解率83.9％。Example 1 200 g of hydrogenated castor oil, manufactured by Toyo Jozo Co., Ltd.
0.1 g (0.05% based on hydrogenated castor oil) of bacterial lipase originating from Chromobacterium viscom var. The hydrolysis reaction was carried out for 48 hours under stirring at 500 rpm. The properties of 12-hydroxystearic acid obtained by separating the aqueous layer containing lipase are as follows. Acid value 153, saponification value 184, hydroxyl value 158,
Iodine value 1.2, decomposition rate 83.9%.
実施例 ２
硬化ヒマシ油200ｇと実施例１で使つたリパー
ゼ0.1ｇ（硬化ヒマシ油に対し0.05％）及び塩化
カルシウム0.005モル濃度を含むオレイルアルコ
ールエチレンオキシド14モル付加体0.5％水溶液
200mlを反応器に仕込み、75℃に保ちながら
500rpmの撹拌下、24時間加水分解を行なつた。
得られた酸の性状は以下の通りである。酸価
168、鹸化価182、水酸基価159、沃素価1.2、分解
率92.0％。Example 2 A 0.5% aqueous solution of oleyl alcohol ethylene oxide 14 molar adduct containing 200 g of hydrogenated castor oil, 0.1 g of the lipase used in Example 1 (0.05% relative to hydrogenated castor oil) and 0.005 molar concentration of calcium chloride.
Pour 200ml into the reactor and keep it at 75℃.
Hydrolysis was carried out for 24 hours under stirring at 500 rpm.
The properties of the obtained acid are as follows. acid value
168, saponification value 182, hydroxyl value 159, iodine value 1.2, decomposition rate 92.0%.
実施例 ３
硬化ヒマシ油200ｇ、実施例１で使つたリパー
ゼ0.1ｇ（硬化ヒマシ油に対し0.025％）及び塩化
カルシウム0.001モル濃度を含む0.3％ノニルフエ
ノールエチレンオキシド17モル、付加体水溶液
200mlを反応器に仕込み、70℃に保ちながら
800rpmの撹拌下、10時間加水分解したのち、水
層を分離除去し、更に一段目と同組成の酵素を含
む新しい反応水層を加えて、同条件下で20時間反
応を続行した。得られた酸の性状は以下の通りで
ある。酸価175、鹸化価184、水酸基価156、沃素
価1.2、分解率95.2％。Example 3 200 g of hydrogenated castor oil, 0.1 g of the lipase used in Example 1 (0.025% relative to hydrogenated castor oil) and 17 moles of 0.3% nonylphenol ethylene oxide containing 0.001 molar concentration of calcium chloride, an aqueous adduct solution.
Pour 200ml into the reactor and keep it at 70℃.
After hydrolysis for 10 hours under stirring at 800 rpm, the aqueous layer was separated and removed, and a new reaction aqueous layer containing the same enzyme composition as the first stage was added, and the reaction was continued under the same conditions for 20 hours. The properties of the obtained acid are as follows. Acid value 175, saponification value 184, hydroxyl value 156, iodine value 1.2, decomposition rate 95.2%.
［発明の効果］
本発明方法により、鹸化分解法による欠点を除
去し、高収率でしかも中和価の高い12−ヒドロキ
システアリン酸を得ることが出来る。即ち、鹸化
分解法の温度より更に低い温度でも加水分解が可
能であり、低温反応のためエステリドの生成が抑
制される。又、加水分解後、反応水をそのままあ
るいは食塩水を加えて分離し、直接甘水としてグ
リセリンを回収出来、廃水処理、芒硝副生等の二
次的な問題も解消出来る。[Effects of the Invention] According to the method of the present invention, the drawbacks caused by the saponification decomposition method can be removed, and 12-hydroxystearic acid can be obtained in high yield and with a high neutralization value. That is, hydrolysis is possible even at a temperature lower than that of saponification and decomposition, and the formation of esterides is suppressed due to the low temperature reaction. Furthermore, after hydrolysis, the reaction water can be separated as it is or with the addition of saline, and glycerin can be recovered directly as sweetened water, which can also solve secondary problems such as wastewater treatment and mirabilite by-products.
Claims (1)
より加水分解することを特徴とするオキシステア
リン酸の製造方法。1. A method for producing oxystearic acid, which comprises hydrolyzing hydrogenated castor oil with a lipase derived from a microorganism.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59262450A JPS61139396A (en) | 1984-12-11 | 1984-12-11 | Production of hydroxystearic acid with lipase |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59262450A JPS61139396A (en) | 1984-12-11 | 1984-12-11 | Production of hydroxystearic acid with lipase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61139396A JPS61139396A (en) | 1986-06-26 |
| JPS6253154B2 true JPS6253154B2 (en) | 1987-11-09 |
Family
ID=17375952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59262450A Granted JPS61139396A (en) | 1984-12-11 | 1984-12-11 | Production of hydroxystearic acid with lipase |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61139396A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104946692A (en) * | 2015-06-10 | 2015-09-30 | 文水县国华油脂有限公司 | Process for preparing 12-hydroxystearic acid through biological hydrolysis by use of hydrogenated castor oil |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1112430C (en) * | 2000-08-24 | 2003-06-25 | 通辽市通华蓖麻化工有限责任公司 | Preparation method of grease chemical product 12-hydroxystearic acid |
| DE10054480A1 (en) * | 2000-11-03 | 2002-05-08 | Cognis Deutschland Gmbh | Process for the production of 12-hydroxystearic acid |
-
1984
- 1984-12-11 JP JP59262450A patent/JPS61139396A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104946692A (en) * | 2015-06-10 | 2015-09-30 | 文水县国华油脂有限公司 | Process for preparing 12-hydroxystearic acid through biological hydrolysis by use of hydrogenated castor oil |
| CN104946692B (en) * | 2015-06-10 | 2018-08-31 | 文水县国华油脂有限公司 | Rilanit special biological hydrolysis process makes 12- hydroxy stearic acid techniques |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61139396A (en) | 1986-06-26 |
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