JP2603111B2 - Method for producing hydrogenated edible oil with low elaidic acid content - Google Patents
Method for producing hydrogenated edible oil with low elaidic acid contentInfo
- Publication number
- JP2603111B2 JP2603111B2 JP63199495A JP19949588A JP2603111B2 JP 2603111 B2 JP2603111 B2 JP 2603111B2 JP 63199495 A JP63199495 A JP 63199495A JP 19949588 A JP19949588 A JP 19949588A JP 2603111 B2 JP2603111 B2 JP 2603111B2
- Authority
- JP
- Japan
- Prior art keywords
- edible oil
- hydrogenation
- elaidic acid
- oil
- hydrogen storage
- 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 - Fee Related
Links
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/32—Hydrogen storage
Description
【発明の詳細な説明】 産業上の利用分野 本発明は、マーガリン、ショートニング等の油脂加工
食品の原料として利用される水素添加食用油の製造方法
に関する。Description: TECHNICAL FIELD The present invention relates to a method for producing a hydrogenated edible oil used as a raw material for processed fats and oils such as margarine and shortening.
技術的背景 液状の油脂をマーガリンやショートニング等の原料油
脂として用いる場合、そのまま使用すると最終製品の保
型性を維持し得ないため、一般的には油脂を構成する脂
肪酸の二重結合部分に水素添加（以下水添という）し、
硬化油として使用している。上記水添方法は反応槽に油
脂と触媒を入れ、120〜200℃程度の温度に保ち、それに
適当な圧力の水素ガスを供給して行う。Technical background When liquid fats and oils are used as raw material fats such as margarine and shortening, if they are used as they are, the shape retention of the final product cannot be maintained. (Hereinafter referred to as hydrogenation)
Used as hardened oil. The above hydrogenation method is carried out by putting fats and oils and a catalyst in a reaction tank, maintaining the temperature at about 120 to 200 ° C., and supplying hydrogen gas at an appropriate pressure thereto.
水添反応のうち、部分水添反応の避け得ない副産物と
して、トランス−オレフイン結合をもつ不飽和脂肪酸
（以下トランス酸という）がある。この代表的なものと
してオレイン酸のトランス異性体であるエライジン酸が
ある。トランス酸は反すう動物脂に極めてわずか含まれ
ているが、大部分の天然油脂中の不飽和脂肪酸の二重結
合は事実上シス型で存在する。多くの分野で、トランス
酸含有油脂は非天然型油脂であるということに関して、
栄養代謝上の問題提起もなされている。そのため、反応
温度、水素圧力および触媒濃度と種類等の反応条件の組
合せを種々勘案することにより、反応を非選択的に進行
せしめ、トランス酸生成量を減少させる工夫（例えば
「油化学」vol.36,No.2,p145,1987）も行われている。Among the hydrogenation reactions, an inevitable by-product of the partial hydrogenation reaction is an unsaturated fatty acid having a trans-olefin bond (hereinafter referred to as trans acid). A typical example is elaidic acid, which is a trans isomer of oleic acid. Although trans acids are contained very little in ruminant fats, the double bonds of unsaturated fatty acids in most natural fats and oils are present in cis form. In many areas, regarding that trans-acid-containing fats and oils are non-natural fats and oils,
Nutritional metabolic problems have also been raised. Therefore, by considering various combinations of reaction conditions such as reaction temperature, hydrogen pressure, and catalyst concentration and type, the reaction can proceed non-selectively to reduce the amount of trans acid generated (for example, "Oil Chemistry" vol. 36, No. 2, p145, 1987).
ところで、水素貯蔵合金は10年ほど前から形状記憶合
金とともに注目されており、現在、水素自動車、ヒート
ポンプ及び室内の冷暖房等の分野で利用されている。水
素貯蔵合金には例えばLaNi5やMg2Niなど多くの種類があ
るが、合金の水素ガス貯蔵量、排出圧力及び排出温度等
の機能は、その構成される金属によって異なつている。Incidentally, hydrogen storage alloys have been attracting attention together with shape memory alloys for about ten years, and are currently used in fields such as hydrogen vehicles, heat pumps, and indoor air conditioning. Although the hydrogen storage alloy has many kinds such as LaNi 5 and Mg 2 Ni, the hydrogen gas storage volume of the alloy, functions such as discharge pressure and discharge temperature are different from one by the configured metal.
この水素貯蔵合金による水添反応の例としては、オレ
フインの水素化、一酸化炭素の水素化及びアンモニアの
合成が「水素貯蔵合金データブック」（与野書房）で、
オレイン酸メチルの常圧水素化分解によるC18アルコー
ル反応については日本化学会（第54回春季年会1987）で
報告されている。As an example of the hydrogenation reaction using this hydrogen storage alloy, hydrogenation of olefin, hydrogenation of carbon monoxide and synthesis of ammonia are described in "Hydrogen storage alloy data book" (Yono Shobo).
The C18 alcohol reaction by atmospheric pressure hydrogenolysis of methyl oleate has been reported by the Chemical Society of Japan (54th Annual Spring Meeting 1987).
しかし、食用油脂を水添する際に、水素貯蔵合金を利
用することについては未だ公開されたものはみられな
い。However, there is no published disclosure of the use of a hydrogen storage alloy when hydrogenating edible fats and oils.
発明が解決しようとする課題 本発明は、水素貯蔵合金を利用して水素添加を行うこ
とにより、エライジン酸含量の少ない水素添加食用油
（以下、水添食用油という）を製造する方法を提供する
ことを課題とする。Problems to be Solved by the Invention The present invention provides a method for producing a hydrogenated edible oil having a low elaidic acid content (hereinafter referred to as a hydrogenated edible oil) by performing hydrogenation using a hydrogen storage alloy. That is the task.
以下本発明を詳しく説明する。 Hereinafter, the present invention will be described in detail.
課題を解決するための手段 本発明におけるエライジン酸含量の少ない水添食用油
は、原料の食用油脂と水素貯蔵合金を反応槽に仕込み、
脱気後、攪拌しながら該油脂を120〜200℃程度の温度に
30〜360分間保持するか、もしくはジャケット式で水素
貯蔵合金を冷却できるようにした棚段式カラムに該合金
を封入し、これに120〜200℃程度の温度に保持された食
用油脂を循環させて、水添反応を行うことにより得るこ
とができる。Means for solving the problem Hydrogenated edible oil having a low elaidic acid content in the present invention is prepared by charging raw material edible oil and fat and a hydrogen storage alloy in a reaction tank,
After degassing, the oils and fats are brought to a temperature of about 120 to 200 ° C while stirring.
Hold the alloy for 30 to 360 minutes, or enclose the alloy in a tray type column in which the hydrogen storage alloy can be cooled in a jacket type, and circulate the edible oil and fat maintained at a temperature of about 120 to 200 ° C. Then, it can be obtained by performing a hydrogenation reaction.
なお、上記水添反応の終了後、水素ガス及び得られた
硬化油（水添食用油）を回収して、冷却した水素貯蔵合
金に水素ガスを再貯蔵させて次回の水添工程に用いるこ
とができる。After completion of the hydrogenation reaction, the hydrogen gas and the obtained hardened oil (hydrogenated edible oil) are collected, and the hydrogen gas is re-stored in the cooled hydrogen storage alloy and used in the next hydrogenation step. Can be.
本発明で用いる水素貯蔵合金としては、水添反応性の
良好なLa−Ni系合金が好ましく、LaNi3.44〜4.495Al0.3
〜1.5Ti0.005〜0.05及びLaNi3.5〜4.5Al0.3〜1.5から成
る群から選択されるものが例示し得る。これらのうち、
LaNi4.0Al1.0、LaNi4.1Al0.9、LaNi3.9Al1.1、及びLaNi
3.99Al1.0Ti0.01などはエライジン酸生成率が低いので
実用上特に好ましい。As the hydrogen storage alloy used in the present invention, a La-Ni-based alloy having good hydrogenation reactivity is preferable, and LaNi 3.44 to 4.495 Al 0.3
Those selected from the group consisting of ~ 1.5 Ti 0.005 ~ 0.05 and LaNi 3.5 ~ 4.5 Al 0.3 ~ 1.5 may be exemplified. Of these,
LaNi 4.0 Al 1.0 , LaNi 4.1 Al 0.9 , LaNi 3.9 Al 1.1 , and LaNi
3.99 Al 1.0 Ti 0.01 or the like is particularly preferable for practical use because of a low elaidic acid production rate.
これらの合金は、工業用水素貯蔵装置に比べ、はるか
に大量の水素ガスを貯蔵でき、しかも低圧で使用できる
ことから、従来の水素ガスによる水添法に比べ安全性の
点で優れている。These alloys can store a much larger amount of hydrogen gas than an industrial hydrogen storage device, and can be used at a low pressure. Therefore, these alloys are superior in safety compared to the conventional hydrogenation method using hydrogen gas.
以下実施例を示して本発明とその効果を具体的に説明
する。Hereinafter, the present invention and its effects will be specifically described with reference to examples.
実施例１ 容量が１リットルのデッドエンド式の反応槽に大豆白
紋油500mlを入れ、105℃、真空度775mmHgで５分間、脱
気、脱水し、冷却した。該油脂に、予め水素を貯蔵させ
た水素貯蔵合金LaNi4.0Al1.0を250g混入し、攪拌しなが
ら反応温度を180℃に調整した。該温度で120分間反応さ
せ、常法に従つて精製して得た硬化油の水添度は26％、
選択性（Selectivity）は0.9であり、エライジン酸生成
率は30％であつた。それに対し従来法で得た同等の水添
度26％を有する硬化油（選択性12.0）のエライジン酸生
成率は94％であつた。Example 1 500 ml of soybean white pattern oil was placed in a dead end type reaction tank having a capacity of 1 liter, degassed, dehydrated and cooled at 105 ° C. and a vacuum of 775 mmHg for 5 minutes. 250 g of a hydrogen storage alloy LaNi 4.0 Al 1.0 in which hydrogen was stored in advance was mixed into the fat and oil, and the reaction temperature was adjusted to 180 ° C. while stirring. The reaction was carried out at this temperature for 120 minutes, and the hydrogenation degree of the hardened oil obtained by purifying according to a conventional method was 26%.
Selectivity was 0.9 and elaidic acid production was 30%. On the other hand, a hardened oil (selectivity 12.0) having a similar degree of hydrogenation of 26% obtained by the conventional method had an elaidic acid production rate of 94%.
尚、ここでいう水添度（％）、選択性及びエライジン
酸生成率は下記を表わす。The degree of hydrogenation (%), selectivity, and elaidic acid production rate are as follows.
水添度（％）＝（水添された二重結合数／全二重結合 数）×100 選択性＝K2/K3（K2：リノール酸からオレイン酸へ水添 される時の反応速度定数） （K3：オレイン酸からステアリン酸へ水 添される時の反応速度定数） エライジン酸生成率（％）＝生成されたエライジン酸／ 水添によつて生成されたオレイン酸＋ エライジン酸 実施例２ 全容量が12リットルの循環式反応槽（循環流量12l/mi
n）に大豆白紋油６リットルを入れ、105℃、真空度755m
mHgで５分間、脱気、脱水した。この大豆白紋油を予め
水素ガスを貯蔵させた水素貯蔵合金LaNi4.1Al0.9約2kg
を封入したジャケット式カラムに流入させ、反応温度を
180℃に調整しながらポンプで循環した。該温度で60分
間反応させ、常法に従つて精製して得た硬化油の水添度
は28％、選択性は2.3であり、エライジン酸生成率は33
％であつた。それに対し従来法で得た同等の水添度26％
を有する硬化油（水添度28％、選択性11.5）のエライジ
ン酸生成率は93％であつた。Water添度(%) = (hydrogenated double bonds / number full number of double bonds) × 100 Selectivity = K 2 / K 3 (K 2: reaction when being hydrogenated linoleic acid to oleic acid (K 3 : reaction rate constant when hydrogenating oleic acid to stearic acid) Elaidic acid production rate (%) = elaidic acid generated / oleic acid generated by hydrogenation + elaidic acid Example 2 Circulation type reaction tank having a total volume of 12 liters (circulation flow rate 12 l / mi
n) Add 6 liters of soybean white pattern oil to 105 ℃, vacuum 755m
Degassed and dehydrated at mHg for 5 minutes. Hydrogen storage alloy LaNi 4.1 Al 0.9 which stores hydrogen gas in advance from this soybean white pattern oil 0.9 approx. 2 kg
Into the jacketed column containing
It was circulated with a pump while adjusting to 180 ° C. The hydrogenated oil obtained by reacting at this temperature for 60 minutes and purifying according to a conventional method had a hydrogenation degree of 28%, a selectivity of 2.3 and an elaidic acid production rate of 33%.
%. On the other hand, the equivalent degree of hydrogenation obtained by the conventional method is 26%
And a hydrogenated oil having a degree of hydrogenation of 28% and a selectivity of 11.5 had an elaidic acid production rate of 93%.
実施例３ 容量が１リットルのデッドエンド式の反応槽に大豆白
紋油400mlを入れ、105℃、真空度755mmHgで５分間、脱
気、脱水し、冷却した。該油脂に、予め水素を貯蔵させ
た水素貯蔵合金LaNi3.9Al1.1を250g混入し、攪拌しなが
ら反応温度を180℃に調整した。該温度で４時間反応さ
せ、常法に従つて精製して得た硬化油の水添度は15％、
選択性は2.6であり、エライジン酸生成率は40％であつ
た。それに対し従来法で得た同等の水添度15％を有する
硬化油（選択性12.0）のエライジン酸生成率は91％であ
った。Example 3 400 ml of soybean white pattern oil was placed in a dead-end type reaction tank having a capacity of 1 liter, degassed and dehydrated at 105 ° C. and a vacuum of 755 mmHg for 5 minutes, and cooled. 250 g of a hydrogen storage alloy LaNi 3.9 Al 1.1 in which hydrogen was stored in advance was mixed with the fat and oil, and the reaction temperature was adjusted to 180 ° C. while stirring. The reaction was carried out at this temperature for 4 hours, and the hydrogenated oil obtained by purifying according to a conventional method had a hydrogenation degree of 15%.
The selectivity was 2.6 and the elaidic acid production rate was 40%. On the other hand, the hardened oil (selectivity 12.0) having the same degree of hydrogenation of 15% and obtained by the conventional method had an elaidic acid production rate of 91%.
実施例４ 容量が１リットルのデッドエンド式の反応槽に大豆白
紋油500mlを入れ、105℃、真空度750mmHgで５分間、脱
気、脱水し、冷却した。該油脂に、予め水素を貯蔵させ
た水素貯蔵合金LaNi3.99Al1.0Ti0.01を250g混入し、攪
拌しながら反応温度を180℃に調整した。該温度で120分
間反応させ、常法に従つて精製して得た硬化油の水添度
は29％、選択性（Selectivity）は0.9であり、エライジ
ン酸生成率は30％であつた。それに対し従来法で得た同
等の水添度29％を有する硬化油（選択性12.0）のエライ
ジン酸生成率は94％であつた。Example 4 500 ml of soybean white pattern oil was placed in a dead-end type reaction tank having a capacity of 1 liter, degassed, dehydrated and cooled at 105 ° C. and a degree of vacuum of 750 mmHg for 5 minutes. 250 g of a hydrogen storage alloy LaNi 3.99 Al 1.0 Ti 0.01 in which hydrogen was stored in advance was mixed into the fat and oil, and the reaction temperature was adjusted to 180 ° C. while stirring. The hydrogenated oil obtained by reacting at this temperature for 120 minutes and purifying according to a conventional method had a hydrogenation degree of 29%, a selectivity of 0.9, and an elaidic acid production rate of 30%. On the other hand, a hardened oil (selectivity 12.0) having the same degree of hydrogenation of 29% obtained by the conventional method had an elaidic acid production rate of 94%.
次に、上記実施例１〜４の水添反応時の選択性とエラ
イジン酸生成率を、従来の水添法のものと比較した結果
を表１に示す。Next, Table 1 shows the results of comparing the selectivity and the elaidic acid production rate during the hydrogenation reaction of Examples 1 to 4 with those of the conventional hydrogenation method.
発明の効果 以上述べたように、本発明に従うと、マーガリンやシ
ョートニング等の油脂加工食品の原料油脂に適した、か
つエライジン酸含量の少ない硬化油を提供することがで
きる。更に、このような硬化油を製造するに当つての水
添反応においても、従来の水添法のように触媒を使用す
ることなく、かつ反応条件の組合せを種々勘案して非選
択的に反応を進行させる工夫を要することなく、選択性
を小さくすることにより、極めて簡単にエライジン酸の
生成量を低減させることが可能となる。また、水添によ
り得られた硬化油の固体脂含量（SFC）の温度依存性を
小さくすることができる。 Effects of the Invention As described above, according to the present invention, it is possible to provide a hardened oil which is suitable as a raw material fat for processed fats and oils such as margarine and shortening and has a low elaidic acid content. Furthermore, in the hydrogenation reaction for producing such a hardened oil, non-selective reaction is performed without using a catalyst as in the conventional hydrogenation method and considering various combinations of reaction conditions. By making the selectivity small without devising a process for proceeding, it is possible to extremely easily reduce the amount of elaidic acid produced. Further, the temperature dependence of the solid fat content (SFC) of the hardened oil obtained by hydrogenation can be reduced.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 佐藤 均 東京都江東区東雲１―９―31 三菱製鋼 株式会社技術開発センター内 (72)発明者 日向野 栄 東京都江東区東雲１―９―31 三菱製鋼 株式会社技術開発センター内 (56)参考文献 特開 昭59−142298（ＪＰ，Ａ) 特開 昭63−268799（ＪＰ，Ａ) 特公 昭40−28273（ＪＰ，Ｂ１) 大角泰章著「金属水素化物−その物性 と応用」昭和58年12月25日 株式会社化 学工業社発行 Ｐ．127〜Ｐ．133，Ｐ. 259〜Ｐ．260 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Hitoshi Sato 1-9-31 Shinonome, Koto-ku, Tokyo Mitsubishi Steel Corporation Technology Development Center (72) Inventor Sakae Hinano 1-9-31 Shinonome, Koto-ku, Tokyo Mitsubishi Steel Development Co., Ltd. (56) References JP-A-59-142298 (JP, A) JP-A-63-268799 (JP, A) JP-B-40-28273 (JP, B1) Hydride-Physical Properties and Applications ”, published December 25, 1983 by Kagaku Kogyo Co., Ltd. 127-P. 133, p. 259-P. 260
Claims (3)
素貯蔵合金を用い、それから排出される水素を添加して
水添することにより、エライジン酸生成量の少ない食用
油を得ることを特徴とする水素添加食用油の製造方法。1. An edible oil having a small amount of elaidic acid is obtained by using a hydrogen storage alloy in which hydrogen gas is previously stored in an edible oil and fat, adding hydrogen discharged from the hydrogen storage alloy and hydrogenating the alloy. Production method of hydrogenated edible oil.
1.5Ti0.005〜0.05及びLaNi3.5〜4.5Al0.3〜1.5からなる
群から選択される１種もしくは２種以上である請求項
（１）に記載の水素添加食用油の製造方法。2. The hydrogen storage alloy is LaNi 3.44 to 4.495 Al 0.3 to
The method for producing a hydrogenated edible oil according to claim 1, wherein the hydrogenated edible oil is one or more selected from the group consisting of 1.5 Ti 0.005 to 0.05 and LaNi 3.5 to 4.5 Al 0.3 to 1.5 .
がら水素添加を行う請求項（１）に記載の水素添加食用
油の製造方法。3. The method for producing a hydrogenated edible oil according to claim 1, wherein the edible fat is hydrogenated while maintaining the temperature at about 120 to 200 ° C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63199495A JP2603111B2 (en) | 1988-08-10 | 1988-08-10 | Method for producing hydrogenated edible oil with low elaidic acid content |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63199495A JP2603111B2 (en) | 1988-08-10 | 1988-08-10 | Method for producing hydrogenated edible oil with low elaidic acid content |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0247197A JPH0247197A (en) | 1990-02-16 |
| JP2603111B2 true JP2603111B2 (en) | 1997-04-23 |
Family
ID=16408769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63199495A Expired - Fee Related JP2603111B2 (en) | 1988-08-10 | 1988-08-10 | Method for producing hydrogenated edible oil with low elaidic acid content |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2603111B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2555423B2 (en) * | 1988-09-14 | 1996-11-20 | 雪印乳業株式会社 | Method of hydrogenating edible fats and oils |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4584139A (en) * | 1983-01-31 | 1986-04-22 | Olin Corporation | Hydrogenation of long chain olefinic oils with Raney catalyst |
| JPS63268799A (en) * | 1987-04-27 | 1988-11-07 | Snow Brand Milk Prod Co Ltd | Method for hydrogenating fat or oil |
-
1988
- 1988-08-10 JP JP63199495A patent/JP2603111B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| 大角泰章著「金属水素化物−その物性と応用」昭和５８年１２月２５日 株式会社化学工業社発行 Ｐ．１２７〜Ｐ．１３３，Ｐ．２５９〜Ｐ．２６０ |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0247197A (en) | 1990-02-16 |
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