JP2007262120A - Method for producing ozonized vegetable oil - Google Patents
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本発明は、オゾン化植物油の製造方法に関するものである。 The present invention relates to a method for producing ozonized vegetable oil.
オゾン化オリーブ油等のオゾン化植物油は、殺菌剤として有用である他、ヒトやウシ等の動物の難治性外表疾患に対して優れた治療効果を示すことが知られている。
このようなオゾン化植物油は、その構成脂肪酸としてオレイン酸を含有する植物油をオゾンガスによってオゾン化することによって得ることができる。例えば、オゾン化オリーブ油を得るために、オリーブ油にオゾン／酸素混合ガスを導通する方法が知られている。この場合、得られるオゾン化オリーブ油は白色ワセリン状のもので、その主成分は、オレイン酸トリグリセリドオゾニドである。
Ozonated vegetable oils such as ozonized olive oil are known not only to be useful as fungicides but also to exhibit excellent therapeutic effects on intractable external surface diseases in animals such as humans and cows.
Such ozonized vegetable oil can be obtained by ozonizing vegetable oil containing oleic acid as its constituent fatty acid with ozone gas. For example, in order to obtain ozonized olive oil, a method of passing an ozone / oxygen mixed gas through olive oil is known. In this case, the ozonized olive oil obtained is in the form of white petrolatum, the main component of which is oleic acid triglyceride ozonide.
オゾン化植物油の製造方法として、例えば、特開２０００−３５１９８５号公報（特許文献１）がある。特許文献１には、植物油を収容、密封した容器内に下方からオゾンを供給噴出させることによりオゾン化植物油を生成する方法において、前記容器の外に植物油を収容したオゾン吸収容器を設置する方法が記載されている。 As a manufacturing method of ozonized vegetable oil, there exists Unexamined-Japanese-Patent No. 2000-351985 (patent document 1), for example. Patent Document 1 discloses a method for generating ozonized vegetable oil by supplying and ejecting ozone from below into a container that contains and seals vegetable oil, and a method of installing an ozone absorbing container that contains vegetable oil outside the container. Are listed.
一方、ヒトや動物の治療薬を製造する場合、その製造方法は、高純度の製品を安定的に製造し得る方法であることが必要である。しかしながら、前記した如き従来の方法では、オゾン化反応を精密に制御する事が出来ず、分解物が副生するなど、高純度の製品を安定的に製造するという点から見ると、未だ満足できないものであった。 On the other hand, when manufacturing therapeutic agents for humans and animals, the manufacturing method needs to be a method capable of stably manufacturing a high-purity product. However, in the conventional method as described above, the ozonation reaction cannot be precisely controlled, and it is still not satisfactory from the viewpoint of stably producing high-purity products such as by-products of decomposition products. It was a thing.
本発明は、オゾン化植物油の製造方法において、高純度の製品を安定的に製造し得る方法を提供することをその課題とする。 This invention makes it the subject to provide the method which can manufacture a highly purified product stably in the manufacturing method of ozonized vegetable oil.
本発明によれば、以下に示すオゾン化植物油の製造方法が提供される。
〔１〕構成脂肪酸としてオレイン酸を含有する植物油（以下、植物油という）からオゾン化植物油を製造する方法において、
（ｉ）オゾン化反応容器内に収容されている該植物油中にオゾン／酸素混合ガスを導入して該植物油をオゾニド化する工程、
（ｉｉ）該植物油と接触後のオゾン／酸素ガスを塔外へ抜き出し、オゾン分解器へ導入して該酸素ガス中に含まれるオゾンを分解除去する工程、
からなり、
（ｉｉｉ）該植物油へのオゾンの１０分間当りの導入量を、該植物油１ｇ当り、５〜１０ｍｇの範囲とし、その平均導入量を７.５〜８.５ｍｇに調節すること、
（ｉｖ）該植物油のオゾン化反応率を、オゾン化反応により生成した含酸素化合物のうちオゾニドの割合が９５質量％以上になるように調節することを特徴とするオゾン化植物油の製造方法。
〔２〕該植物油がオリーブ油であり、該オリーブ油のオゾン吸収率が１４〜１８質量％になった時点で該反応を停止することを特徴とする前記〔１〕に記載のオゾン化植物油の製造方法。
〔３〕該オゾン化反応容器内のオゾン化反応生成物の質量を測定し、この質量測定値に基づいてオゾン吸収率を算出し、このオゾン吸収率に対応して、該植物油を冷却または加熱することを特徴とする前記〔１〕又は〔２〕に記載のオゾン化植物油の製造方法。
〔４〕該オゾン化反応の進行に応じて生じる該オゾン化反応生成物の白濁開始温度の上昇に応じて該オゾン化反応温度を上昇させるとともに、該オゾン化反応温度を該オゾン化反応生成物の白濁開始温度：［Ｗ］℃以上で且つ白濁開始温度より１０℃高い温度：［Ｗ＋１０］℃以下の温度に保持することを特徴とする前記〔１〕〜〔３〕のいずれかに記載のオゾン化植物油の製造方法。
According to this invention, the manufacturing method of the ozonized vegetable oil shown below is provided.
[1] In a method for producing ozonized vegetable oil from a vegetable oil containing oleic acid as a constituent fatty acid (hereinafter referred to as vegetable oil),
(I) a step of introducing an ozone / oxygen mixed gas into the vegetable oil contained in the ozonization reaction vessel to convert the vegetable oil into an ozonide;
(Ii) extracting ozone / oxygen gas after contact with the vegetable oil out of the tower and introducing it into an ozone decomposer to decompose and remove ozone contained in the oxygen gas;
Consists of
(Iii) The amount of ozone introduced into the vegetable oil per 10 minutes is in the range of 5 to 10 mg per gram of the vegetable oil, and the average amount introduced is adjusted to 7.5 to 8.5 mg.
(Iv) A method for producing an ozonized vegetable oil, characterized in that the ozonization reaction rate of the vegetable oil is adjusted so that the proportion of ozonide in the oxygenated compound produced by the ozonization reaction is 95% by mass or more.
[2] The method for producing ozonized vegetable oil according to [1], wherein the vegetable oil is olive oil, and the reaction is stopped when the ozone absorption rate of the olive oil reaches 14 to 18% by mass. .
[3] The mass of the ozonation reaction product in the ozonation reaction vessel is measured, the ozone absorption rate is calculated based on the mass measurement value, and the vegetable oil is cooled or heated according to the ozone absorption rate. The method for producing an ozonized vegetable oil according to the above [1] or [2].
[4] The ozonization reaction temperature is raised in accordance with the increase in the cloudiness start temperature of the ozonation reaction product generated in accordance with the progress of the ozonation reaction, and the ozonation reaction temperature is set to the ozonation reaction product. The white turbidity start temperature: [W] ° C. or higher and 10 ° C. higher than the white turbidity start temperature: maintained at a temperature of [W + 10] ° C. or lower, according to any one of the above [1] to [3] A method for producing ozonized vegetable oil.
本発明によれば、高純度のオゾン化植物油を安定的に製造する方法が提供される。本発明により得られるオゾン化植物油は、そのまま殺菌剤や治療薬として用いることができる。 According to the present invention, a method for stably producing high purity ozonized vegetable oil is provided. The ozonized vegetable oil obtained by the present invention can be used as it is as a bactericidal agent or a therapeutic agent.
本発明で用いる植物油は、その構成脂肪酸成分としてオレイン酸を含有するものである。そのオレイン酸の含有割合は、全構成脂肪酸中、３０モル％以上、好ましくは５０モル％以上、より好ましくは８０モル％以上である。このような植物油としては、オリーブ油やベニバナ油等が挙げられる。 The vegetable oil used in the present invention contains oleic acid as a constituent fatty acid component. The content ratio of the oleic acid is 30 mol% or more, preferably 50 mol% or more, more preferably 80 mol% or more in all the constituent fatty acids. Examples of such vegetable oils include olive oil and safflower oil.
本発明で用いるオゾン化剤は、オゾン／酸素混合ガスである。該混合ガスの流量は、植物油１ｇ当りの流量で、１０分間当たり１．５×１０−３〜５×１０−３Ｌが好ましく、５×１０−３〜７×１０−３Ｌがより好ましい。このような混合ガスは、酸素内で無声放電を行うことによって得ることができる。 The ozonizing agent used in the present invention is an ozone / oxygen mixed gas. The flow rate of the mixed gas is a flow rate per 1 g of vegetable oil, preferably 1.5 × 10 −3 to 5 × 10 −3 L per 10 minutes, and more preferably 5 × 10 −3 to 7 × 10 −3 L. Such a mixed gas can be obtained by performing silent discharge in oxygen.
本発明においては、オゾン化反応容器内に収容させた植物油中にオゾン／酸素混合ガスを導入して、オゾン化反応を行う。この場合、植物油中にその構成脂肪酸として含まれるオレイン酸の二重結合がオゾンと反応して、オゾン化植物油（オレイン酸トリグリセリドオゾニド）が生成される。植物油と接触した後の混合ガスは、塔外へ排出され、オゾン分解器に導入され、ここで未反応オゾンは触媒の存在下で分解されて無害の酸素となり、大気中へ放散される。 In the present invention, the ozone / oxygen mixed gas is introduced into the vegetable oil accommodated in the ozonization reaction vessel to perform the ozonation reaction. In this case, the double bond of oleic acid contained as a constituent fatty acid in the vegetable oil reacts with ozone to produce ozonized vegetable oil (oleic acid triglyceride ozonide). The mixed gas after contact with the vegetable oil is discharged to the outside of the tower and introduced into an ozonolysis unit, where unreacted ozone is decomposed in the presence of a catalyst into harmless oxygen and is released into the atmosphere.
植物油中へオゾン／酸素混合ガスを導入する場合、本発明においては、その導入速度をオゾンの流量が特定範囲内に入るように調節する。
即ち、本発明の場合、オゾン濃度及び流量を可変することにより、植物油中へのオゾンの１０分間当たりの導入量を、植物油１ｇ当り、５〜１０ｍｇの範囲に調整する。本発明においては、更に、植物油中へのオゾンの１０分間当たりの平均導入量を、植物油１ｇ当り、７.５〜８.５ｍｇ、好ましくは約８.０ｍｇに調節する。
When the ozone / oxygen mixed gas is introduced into the vegetable oil, in the present invention, the introduction rate is adjusted so that the flow rate of ozone falls within a specific range.
That is, in the case of the present invention, by changing the ozone concentration and flow rate, the amount of ozone introduced into the vegetable oil per 10 minutes is adjusted to a range of 5 to 10 mg per 1 g of vegetable oil. In the present invention, the average amount of ozone introduced into the vegetable oil per 10 minutes is adjusted to 7.5 to 8.5 mg, preferably about 8.0 mg, per 1 g of vegetable oil.
植物油中へ導入するオゾン／酸素混合ガスの導入速度を前記のような特定範囲に設定することにより、副反応の発生を抑制して、植物油中に含まれているオレイン酸成分を高選択率でオゾニドに変換することができる。 By setting the introduction rate of the ozone / oxygen mixed gas to be introduced into the vegetable oil within the specific range as described above, the occurrence of side reactions is suppressed, and the oleic acid component contained in the vegetable oil is highly selected. Can be converted to ozonide.
本発明のオゾン化反応工程において、その反応温度は、好ましくは３０〜５０℃、より好ましくは３５〜４５℃、更に好ましくは３５〜４０℃である。 In the ozonization reaction step of the present invention, the reaction temperature is preferably 30 to 50 ° C, more preferably 35 to 45 ° C, and still more preferably 35 to 40 ° C.
本発明のオゾン化反応工程において、植物油中へ導入する混合ガス中のオゾン濃度Ａに対する、植物油と接触後の酸素ガス中の未反応オゾン濃度Ｂの比Ｂ／Ａは、好ましくは０〜０．０１、より好ましくは０である。 In the ozonization reaction step of the present invention, the ratio B / A of the unreacted ozone concentration B in the oxygen gas after contact with the vegetable oil to the ozone concentration A in the mixed gas introduced into the vegetable oil is preferably 0 to 0.00. 01, more preferably 0.
前記のようにして植物油のオゾン化（オゾニド化）を継続すると、植物油のオゾン化反応率は、時間の経過とともに、徐々に上昇する。本発明では、植物油のオゾン化反応を前記特定の条件で実施するとともに、そのオゾン化反応率がその植物油に対応した特定範囲の値になった時点でその反応を停止する。例えば、植物油がオリーブ油の場合、オゾンの吸収率（オリーブ油の質量に対する反応したオゾンの質量比）が好ましくは１４〜１８質量％、より好ましくは１５〜１７質量％、更に好ましくは約１６質量％となったときに、その反応を停止し、オゾン化反応容器からその植物油を回収する。 When the ozonization (ozonide) of the vegetable oil is continued as described above, the ozonization reaction rate of the vegetable oil gradually increases with time. In the present invention, the ozonization reaction of the vegetable oil is performed under the specific conditions, and the reaction is stopped when the ozonization reaction rate reaches a value in a specific range corresponding to the vegetable oil. For example, when the vegetable oil is olive oil, the absorption rate of ozone (mass ratio of reacted ozone to the mass of olive oil) is preferably 14 to 18% by mass, more preferably 15 to 17% by mass, and still more preferably about 16% by mass. When this happens, the reaction is stopped and the vegetable oil is recovered from the ozonation reaction vessel.
他の植物油のオゾン化も、前記オリーブ油の場合と同様に、そのオゾンの吸収率が所定範囲に達したときに、その反応を停止する。
この場合、その所定範囲のオゾン化反応率は、オゾン化反応により生成した含酸素化合物のうち、オゾニドの割合が好ましくは９０質量％以上、より好ましくは９５質量％以上で、副生成物（カルボン酸等）の割合が好ましくは１０質量％、より好ましくは５質量％以下となる反応率である。
In the ozonization of other vegetable oils, as in the case of the olive oil, the reaction is stopped when the ozone absorption rate reaches a predetermined range.
In this case, the ozonization reaction rate within the predetermined range is such that the ratio of ozonide is preferably 90% by mass or more, more preferably 95% by mass or more, among the oxygen-containing compounds generated by the ozonization reaction, The reaction rate is preferably 10% by mass, more preferably 5% by mass or less.
本発明により得られるオゾン化植物油は、オレイン酸グリセリドオゾニドを概ね５０質量％程度含有するもので、白色ワセリン状を呈し、優れた保存安定性を示す。例えば、常温（２５℃）において、約３ヶ月、冷蔵（4℃）保存では３年以上経過しても、実質的な変化を生じない。そして、このものは、そのままで殺菌剤や治療薬等として使用することができる。 The ozonized vegetable oil obtained by the present invention contains about 50% by mass of oleic acid glyceride ozonide, exhibits a white petrolatum, and exhibits excellent storage stability. For example, at room temperature (25 ° C.), about 3 months, and when stored at refrigerated (4 ° C.), there is no substantial change even after 3 years. And this thing can be used as a disinfectant, a therapeutic agent, etc. as it is.
前記のようにして植物油をオゾン化する場合、該オゾン化反応生成物（オゾン化反応容器内容物）の白濁開始温度は、該オゾン化反応の進行とともに、上昇する。本発明では、この白濁開始温度の上昇に応じて、該オゾン化反応温度を上昇させることが好ましい。 When vegetable oil is ozonized as described above, the cloudiness start temperature of the ozonization reaction product (the contents of the ozonation reaction vessel) increases as the ozonization reaction proceeds. In the present invention, it is preferable to increase the ozonization reaction temperature in accordance with the increase in the cloudiness start temperature.
本発明の場合、そのオゾン化反応温度を、該オゾン化反応生成物の白濁開始温度：［Ｗ］℃以上で且つ白濁開始温度より１０℃高い温度：［Ｗ＋１０］℃以下の温度に保持することが好ましく、白濁開始温度より８℃高い温度：［Ｗ＋８］℃以下の温度に保持することがより好ましく、白濁開始温度より６℃高い温度：［Ｗ＋６］℃以下の温度に保持することが更に好ましく、白濁開始温度より５℃高い温度：［Ｗ＋５］℃以下の温度に保持することが特に好ましい。この範囲内で反応させれば、植物油の流動性が保持されるので、攪拌を容易に行うことができる。また、副生成物（カルボン酸等）の割合も低く抑えることができる。
白濁開始温度は、植物油が白濁し始める温度を観察することにより求めることができる。具体的には、オリーブ油の場合、その白濁開始温度は５〜１０℃である。
In the case of the present invention, the ozonization reaction temperature is maintained at a temperature of the turbidity start temperature of the ozonation reaction product: [W] ° C. or more and 10 ° C. higher than the turbidity start temperature: [W + 10] ° C. or less. More preferably, the temperature is 8 ° C. higher than the white turbidity start temperature: more preferably [W + 8] ° C. or less, and the temperature 6 ° C. higher than the white turbidity start temperature is more preferably [W + 6] ° C. or less. It is particularly preferable that the temperature be 5 ° C. higher than the white turbidity start temperature: [W + 5] ° C. or lower. If it reacts within this range, since the fluidity | liquidity of a vegetable oil is hold | maintained, stirring can be performed easily. Moreover, the ratio of by-products (such as carboxylic acid) can be kept low.
The cloudiness start temperature can be determined by observing the temperature at which the vegetable oil begins to become cloudy. Specifically, in the case of olive oil, the cloudiness start temperature is 5 to 10 ° C.
尚、反応温度が［Ｗ］〜［Ｗ＋１０］℃の範囲内となるように反応を行うことは、そのつど白濁開始温度：［Ｗ］を測定する必要はなく、植物油の白濁化が観察される温度より１０℃以下であって、容易に攪拌することができる温度に設定すればよい。 In addition, it is not necessary to measure the cloudiness start temperature: [W] each time the reaction is performed so that the reaction temperature is within the range of [W] to [W + 10] ° C., and the cloudiness of the vegetable oil is observed. What is necessary is just to set to the temperature which is 10 degrees C or less from temperature, and can be stirred easily.
前記のようにして植物油のオゾン化反応を行うときには、該オゾン化反応は、気体／固体反応系ではなく、気体／液体反応系で進行するので、反応容器内容物の攪拌混合も容易になり、該オゾン化反応を効率よく且つ円滑に実施することができる。しかも、該オゾン化反応温度は、可及的低い温度に保持されているので、好ましくない副反応も効果的に抑制され、高純度のオゾン化植物油を収率よく、安定的に得ることができる。 When the ozonization reaction of vegetable oil is performed as described above, the ozonation reaction proceeds not in a gas / solid reaction system but in a gas / liquid reaction system, so that stirring and mixing of the reaction vessel contents becomes easy. The ozonization reaction can be carried out efficiently and smoothly. In addition, since the ozonization reaction temperature is maintained as low as possible, undesirable side reactions are effectively suppressed, and high-purity ozonized vegetable oil can be stably obtained with high yield. .
次に、本発明を実施する場合のフローシートの１例を図１に示す。
図１に示したロードセルは、植物油を含むオゾン化反応容器の質量を測定するためのもので、その質量を、反応の経過とともに、経時的に測定することにより、植物油のオゾン化吸収率の変化を知ることができる。植物油のオゾン吸収率が前記好ましい値になった時点で反応を停止させる。
Next, FIG. 1 shows an example of a flow sheet for carrying out the present invention.
The load cell shown in FIG. 1 is for measuring the mass of an ozonation reaction vessel containing vegetable oil. By measuring the mass over time as the reaction progresses, the change in ozonization absorption rate of vegetable oil is measured. Can know. The reaction is stopped when the ozone absorption rate of the vegetable oil reaches the preferred value.
図１において示した質量偏差計測は、反応時間の経過に応じて予め設定したオゾン化反応容器の質量変化を基準値とし、この基準値に対するオゾン化反応容器の質量偏差（即ち、植物油の質量偏差）を計測するものである。そして、その計測情報は、酸素の流量制御工程およびオゾン発生制御工程へ送られる。この場合、その質量偏差計測値がプラスの場合、オゾン化反応が予定よりも進んでいることになるので、オゾン/酸素混合ガスの濃度、流量を減少させる。一方、その計測値がマイナスの場合、オゾン化反応が予定よりも遅れていることになるので、オゾン/酸素混合ガスの濃度、流量を増加させる。 The mass deviation measurement shown in FIG. 1 is based on the mass change of the ozonation reaction vessel set in advance as the reaction time elapses, and the mass deviation of the ozonation reaction vessel with respect to this reference value (ie, the mass deviation of vegetable oil). ). Then, the measurement information is sent to an oxygen flow rate control step and an ozone generation control step. In this case, if the measured value of the mass deviation is positive, the ozonation reaction has progressed more than planned, so the concentration and flow rate of the ozone / oxygen mixed gas are decreased. On the other hand, when the measured value is negative, the ozonation reaction is delayed from the schedule, so the concentration and flow rate of the ozone / oxygen mixed gas are increased.
次に、本発明を実施例により詳述する。 Next, the present invention will be described in detail by examples.
実施例１
図１に示した構造のオゾン化反応容器を用いて実験を行った。この場合、その反応容器は、内径：２００ｍｍ、高さ：３５０mmのガラス製円筒体である。
このオゾン化反応容器内にオリーブ油２,０００ｇを充填し、このオリーブ油に対して、攪拌下でオゾン／酸素混合ガスを導入した。この場合の操作条件は以下の通りである。
Example 1
An experiment was conducted using an ozonation reaction vessel having the structure shown in FIG. In this case, the reaction vessel is a glass cylinder having an inner diameter of 200 mm and a height of 350 mm.
The ozonization reaction vessel was filled with 2,000 g of olive oil, and an ozone / oxygen mixed gas was introduced into the olive oil with stirring. The operating conditions in this case are as follows.
（ｉ）オリーブ油へ導入する混合ガス中のオゾン濃度Ａと流速
反応初期は植物油の中の不飽和脂肪酸が多量にあるため、酸素流量（混合ガス流量）は１Ｌ／ｍｉｎでオゾン濃度は１リットル中約１６６０ｍｇ（オリーブ油１ｇ当りのオゾン１０分間当りの流入量８．３ｍｇ）程度とし、反応時間が経過するに従って酸素流量を０．５L／ｍｉｎとし、オゾン濃度を７５０ｍｇ（オリーブ油１ｇ当りのオゾン１０分間当りの流入量７．５ｍｇ）程度に変化させた（オリーブ油１ｇ当りのオゾン１０分間当りの平均流入量８ｍｇ）。
（ｉｉ）オリーブ油と接触後の酸素ガス中のオゾン濃度Ｂ
初期はオゾン全量がオリーブ油に反応して排出される酸素ガス中のオゾン濃度はゼロである。尚、植物油中へ導入する混合ガス中のオゾン濃度Ａに対する、植物油と接触後の酸素ガス中の未反応オゾン濃度Ｂの比Ｂ／Ａは０である。
（ｉｉｉ）酸素流量１Ｌ／ｍｉｎにおける反応温度：７℃で開始し３５℃以上にならないように［Ｗ］〜［Ｗ＋１０］℃の範囲内で行った
酸素流量０．５L／ｍｉｎにおける反応温度：３５〜３８℃
(I) Ozone concentration A and flow rate in the mixed gas to be introduced into olive oil Since there are a lot of unsaturated fatty acids in the vegetable oil at the beginning of the reaction, the oxygen flow rate (mixed gas flow rate) is 1 L / min and the ozone concentration is in 1 liter. About 1660 mg (flow rate of 8.3 mg of ozone per gram of olive oil per 10 minutes), oxygen flow rate is 0.5 L / min as the reaction time elapses, and ozone concentration is 750 mg (per 10 minutes of ozone per gram of olive oil) Inflow of 7.5 mg) (average inflow of 8 mg per 10 minutes of ozone per gram of olive oil).
(Ii) Ozone concentration B in oxygen gas after contact with olive oil
Initially, the ozone concentration in the oxygen gas exhausted when the total amount of ozone reacts with olive oil is zero. The ratio B / A of the unreacted ozone concentration B in the oxygen gas after contact with the vegetable oil to the ozone concentration A in the mixed gas introduced into the vegetable oil is 0.
(Iii) Reaction temperature at an oxygen flow rate of 1 L / min: The reaction temperature was started at 7 ° C. and was carried out within the range of [W] to [W + 10] ° C. so as not to exceed 35 ° C.
Reaction temperature at an oxygen flow rate of 0.5 L / min: 35 to 38 ° C
前記の条件で反応を行った結果、オリーブ油のオゾンの吸収率が１６質量％増になったので、反応を停止し、内容物（オゾン化オリーブ油）を回収した。このものは、副反応生成物を殆ど含まない高純度のオレイン酸グリセリドオゾニドを主体とするもので、該オゾニドの含有率は、全オゾン化生成物中１００質量％であった。また、このものは、白色ワセリン状を示すものであった。このものは、常温で３ヶ月間保存しても、実質的な質量変化および成分変化を生じなかった。 As a result of performing the reaction under the above conditions, the ozone absorption rate of olive oil was increased by 16% by mass, so the reaction was stopped and the contents (ozonized olive oil) were recovered. This was mainly composed of high-purity oleic acid glyceride ozonide containing almost no side reaction products, and the content of the ozonide was 100% by mass in the total ozonized product. Moreover, this thing showed white petrolatum. Even when this product was stored at room temperature for 3 months, no substantial mass change or component change occurred.
なお、前記反応温度は、反応の進行に応じてオゾン化植物油の白濁開始温度が上昇し、その流動性が低下することから、流動性を保持し、攪拌を容易に行うために、前記温度範囲内で徐々に上昇させた。 The reaction temperature is the temperature range in order to maintain the fluidity and easily perform the stirring because the cloudiness start temperature of the ozonized vegetable oil increases and the fluidity decreases as the reaction proceeds. Gradually increased within.
比較例１
実施例１において、オリーブ油のオゾン化吸収率が２０質量％増になった時点で、反応を停止した。 得られた反応生成物中の副反応生成物は、全オゾン化生成物（含酸素化合物）中５質量％より高いものであった。
Comparative Example 1
In Example 1, the reaction was stopped when the ozonization absorption rate of olive oil increased by 20% by mass. The side reaction product in the obtained reaction product was higher than 5% by mass in the total ozonation product (oxygen-containing compound).
Claims (4)
（ｉ）オゾン化反応容器内に収容されている該植物油中にオゾン／酸素混合ガスを導入して該植物油をオゾニド化する工程、
（ｉｉ）該植物油と接触後のオゾン／酸素ガスを塔外へ抜き出し、オゾン分解器へ導入して該酸素ガス中に含まれるオゾンを分解除去する工程、
からなり、
（ｉｉｉ）該植物油へのオゾンの１０分間当りの導入量を、該植物油１ｇ当り、５〜１０ｍｇの範囲とし、その平均導入量を７.５〜８.５ｍｇに調節すること、
（ｉｖ）該植物油のオゾン化反応率を、オゾン化反応により生成した含酸素化合物のうちオゾニドの割合が９５質量％以上になるように調節することを特徴とするオゾン化植物油の製造方法。 In a method for producing ozonized vegetable oil from a vegetable oil containing oleic acid as a constituent fatty acid,
(I) a step of introducing an ozone / oxygen mixed gas into the vegetable oil contained in the ozonization reaction vessel to convert the vegetable oil into an ozonide;
(Ii) extracting ozone / oxygen gas after contact with the vegetable oil out of the tower and introducing it into an ozone decomposer to decompose and remove ozone contained in the oxygen gas;
Consists of
(Iii) The amount of ozone introduced into the vegetable oil per 10 minutes is in the range of 5 to 10 mg per gram of the vegetable oil, and the average amount introduced is adjusted to 7.5 to 8.5 mg.
(Iv) A method for producing an ozonized vegetable oil, characterized in that the ozonization reaction rate of the vegetable oil is adjusted so that the proportion of ozonide in the oxygenated compound produced by the ozonization reaction is 95% by mass or more.
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| CN108018119A (en) * | 2017-12-14 | 2018-05-11 | 长沙思麦食品开发有限公司 | A kind of method that ozone is efficiently mutually mixed with vegetable oil |
| CN108057350A (en) * | 2017-12-14 | 2018-05-22 | 长沙思麦食品开发有限公司 | A kind of solubilization method of ozone in tea oil |
| CN109234021A (en) * | 2018-09-26 | 2019-01-18 | 西安科技大学 | A kind of preparation method of medical ozone carburetion |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108018119A (en) * | 2017-12-14 | 2018-05-11 | 长沙思麦食品开发有限公司 | A kind of method that ozone is efficiently mutually mixed with vegetable oil |
| CN108057350A (en) * | 2017-12-14 | 2018-05-22 | 长沙思麦食品开发有限公司 | A kind of solubilization method of ozone in tea oil |
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