JPH0448420B2 - - Google Patents
Info
- Publication number
- JPH0448420B2 JPH0448420B2 JP59033112A JP3311284A JPH0448420B2 JP H0448420 B2 JPH0448420 B2 JP H0448420B2 JP 59033112 A JP59033112 A JP 59033112A JP 3311284 A JP3311284 A JP 3311284A JP H0448420 B2 JPH0448420 B2 JP H0448420B2
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- water
- extraction
- aqueous solution
- tank
- 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 - Lifetime
Links
- 239000000049 pigment Substances 0.000 claims description 23
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 16
- 238000000605 extraction Methods 0.000 claims description 16
- 239000002994 raw material Substances 0.000 claims description 9
- 239000001569 carbon dioxide Substances 0.000 claims description 8
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000003921 oil Substances 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 235000010208 anthocyanin Nutrition 0.000 claims description 3
- 239000004410 anthocyanin Substances 0.000 claims description 3
- 229930002877 anthocyanin Natural products 0.000 claims description 3
- 150000004636 anthocyanins Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 235000000842 betacyanins Nutrition 0.000 claims description 2
- 235000021466 carotenoid Nutrition 0.000 claims description 2
- 150000001747 carotenoids Chemical class 0.000 claims description 2
- 239000003925 fat Substances 0.000 claims description 2
- 229930003944 flavone Natural products 0.000 claims description 2
- 235000011949 flavones Nutrition 0.000 claims description 2
- 229930003935 flavonoid Natural products 0.000 claims description 2
- 150000002215 flavonoids Chemical class 0.000 claims description 2
- 235000017173 flavonoids Nutrition 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 2
- DHHFDKNIEVKVKS-FMOSSLLZSA-N Betanin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC(C(=C1)O)=CC(C[C@H]2C([O-])=O)=C1[N+]2=C\C=C\1C=C(C(O)=O)N[C@H](C(O)=O)C/1 DHHFDKNIEVKVKS-FMOSSLLZSA-N 0.000 claims 1
- 108010053210 Phycocyanin Proteins 0.000 claims 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 claims 1
- 150000002212 flavone derivatives Chemical class 0.000 claims 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 claims 1
- 239000000975 dye Substances 0.000 description 12
- 238000000926 separation method Methods 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000012530 fluid Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 241000209149 Zea Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000000108 ultra-filtration Methods 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 244000178937 Brassica oleracea var. capitata Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000012730 carminic acid Nutrition 0.000 description 1
- 239000004106 carminic acid Substances 0.000 description 1
- 229940080423 cochineal Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000000576 food coloring agent Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003014 ion exchange membrane Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000008601 oleoresin Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Description
【発明の詳細な説明】
この発明は、色素に係るものであり、品質の優
れた食用色素を工業的に有利に収得することを目
的とする。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to pigments and aims to industrially advantageously obtain food pigments of excellent quality.
食用色素は、水溶性のものと油溶性のものとに
２大別される。この発明は、前者即ち水溶性の色
素に係るものである。 Food coloring is divided into two types: water-soluble and oil-soluble. This invention relates to the former, that is, water-soluble dyes.
水溶性色素の収得法としては、溶剤抽出法等が
あるが、これ等の方法はいずれも重大な欠点を持
つている。欠点としては、例えば、製品の収得歩
留りが低い、夾雑物の除去割合が低い、時として
収得した色素の変色が起こる、その他である。 Methods for obtaining water-soluble pigments include solvent extraction methods, but all of these methods have serious drawbacks. Disadvantages include, for example, a low yield of product, a low rate of removal of impurities, and occasional discoloration of the dye obtained.
この発明は、このような欠点のないものであ
る。以下にこの発明を説明する。 The present invention is free from such drawbacks. This invention will be explained below.
まず、対象の色素原料は、水溶性であつて非親
油性の色素を含むもの一般である。それには、フ
ラボノイド系、アントシアニン系、キノン系、ベ
タシアニン系、フラボン系、アザフイロン系、フ
イコシアニン系、一部のカロチノイド系のものそ
の他があげられる。植物の葉莖、果肉、根等、魚
貝類の皮、肉、血液等がこれを等色素を含有する
原料である。これらのオレオレジンも原料とする
ことができる。これらの生鮮物、乾燥物のいずれ
でもよい。これらは、単種でまたは２種以上併せ
て処理される。 First, the target dye raw material is generally one containing a water-soluble and non-lipophilic dye. These include flavonoids, anthocyanins, quinones, betacyanins, flavones, azaphyrons, phycocyanins, some carotenoids, and others. The leaf pods, pulp, and roots of plants, the skin, meat, and blood of fish and shellfish are raw materials that contain this pigment. These oleoresins can also be used as raw materials. Either of these fresh or dried products may be used. These may be treated singly or in combination of two or more.
つぎに、色素収得の工程を説明する。 Next, the process of obtaining the dye will be explained.
これ等の色素原料を超臨界状態の流体で処理す
る。これが、この発明の特徴である。 These dye raw materials are treated with a fluid in a supercritical state. This is a feature of this invention.
炭素ガス、エチレン、プロパン等の流体を適当
量の色素原料に接触させ、臨界点以上の温度圧力
下の密閉系におく。この際、採用する装置は基本
的には流体の供給源、熱交換器、圧縮器、抽出タ
ンク、分離タンクを連結してなる密閉系である。
このような装置でさえあれば、その形式のいかん
にかかわりなく採用することができる。このよう
にすると、原料中に含まれる夾雑物例えば油脂、
水分の一部、揮発分は分離タンクに導かれる。分
離タンクでは温度あるいは圧力を変化させて、こ
れ等を系外に排出する。したがつて、抽出タンク
には、液状ないし固状物が残留する。この残留部
は色素、繊維質、蛋白質、一部の糖算、灰分、水
分等の混合物である。 A fluid such as carbon gas, ethylene, propane, etc. is brought into contact with an appropriate amount of dye raw material and placed in a closed system under temperature and pressure above the critical point. At this time, the equipment employed is basically a closed system that connects a fluid supply source, heat exchanger, compressor, extraction tank, and separation tank.
As long as such a device exists, it can be employed regardless of its format. In this way, impurities contained in the raw materials, such as oils and fats,
Part of the moisture and volatile components are led to a separation tank. In the separation tank, these are discharged from the system by changing the temperature or pressure. Therefore, liquid or solid matter remains in the extraction tank. This residual portion is a mixture of pigments, fibers, proteins, some sugar content, ash, moisture, etc.
油脂分及び揮発分その他の除去率が所望に達し
たとき、運転を止め、抽出タンクから残留液ない
し固状部を取り出す。取り出したものに水または
アルコールまたは有機酸の水溶液を添加して、抽
出残中に含有される色素成分に水またはアルコー
ルまたは有機酸の水溶液に移行させ、該溶液に色
素を溶解させてなる溶液のみを取り出し、これを
減圧濃縮し、又はイオン交換膜、逆滲透もしくは
限外濾過その他の常法を使用して濃縮し色素分
のみを採取する。 When the desired removal rate of fats and oils, volatile matter, etc. is reached, the operation is stopped and the residual liquid or solids are removed from the extraction tank. Only a solution is obtained by adding water, alcohol, or an aqueous solution of an organic acid to the extracted material, causing the pigment components contained in the extraction residue to be transferred to the aqueous solution of water, alcohol, or an organic acid, and dissolving the pigment in the solution. is taken out and concentrated under reduced pressure, or concentrated using an ion exchange membrane, reverse filtration, ultrafiltration, or other conventional method to collect only the pigment.
以上により、この発明の目的を達しおえる。 Through the above, the purpose of this invention can be achieved.
この発明の特徴の若干を記すと、次の通りであ
る。色素の変色が極めて少ない。比較的低い温
度で処理するから、色素の固有変色温度以下の温
度において、製造することができるからである。
製品の収得率が極めて高い。原料に含有する色
素分は気化逃散することなく、抽出タンクに全量
が残留し、これを水を用いて殆んど全量を捕集す
ることができるからである。製造工程が極めて
簡易であるから、生産性が極めて高い。使用流
体の気化した部分は、その殆とんど全量を回収再
使用することができ、損耗率が極めて少ない。 Some of the features of this invention are as follows. There is very little discoloration of the pigment. This is because the treatment is performed at a relatively low temperature, so that it can be produced at a temperature below the inherent discoloration temperature of the dye.
Product yield is extremely high. This is because the entire amount of the pigment contained in the raw material remains in the extraction tank without vaporizing and escaping, and almost the entire amount can be collected using water. Since the manufacturing process is extremely simple, productivity is extremely high. Almost all of the vaporized portion of the used fluid can be recovered and reused, and the rate of loss is extremely low.
つぎに実施例によりこの発明を詳しく説明す
る。 Next, the present invention will be explained in detail with reference to Examples.
実施例 １
赤キヤベツ1500ｇをすり潰してジユースにし、
その１ｇと超臨界状態の炭酸ガスを接触させ、こ
の接触させた炭酸ガスは抽出系外において等圧で
温度を上昇させることにより、抽出した油分、揮
発成分を除去した。Example 1 Grind 1500g of red cabbage to make juice.
1 g of the mixture was brought into contact with carbon dioxide gas in a supercritical state, and the temperature of the contacted carbon dioxide gas was raised at equal pressure outside the extraction system to remove the extracted oil and volatile components.
使用した炭酸ガスは温度を下げ、更にもとの系
に戻し、抽出に再使用した。このようにして夾雑
物を抽出除去した後、残査を得た。この物を粉砕
し、これに50％エタノール水を500ml添加して均
質系にし、これを常温下に３時間撹拌した後、
過、減圧濃縮して、アントシアニン系色素20ｇを
得た。収得した色素は、異味異臭がまつたくな
く、また変退色していなかつた。 The temperature of the carbon dioxide gas used was lowered, and it was returned to the original system and reused for extraction. After extracting and removing impurities in this manner, a residue was obtained. This material was crushed, 500 ml of 50% ethanol water was added to it to make a homogeneous system, and this was stirred at room temperature for 3 hours.
The mixture was filtered and concentrated under reduced pressure to obtain 20 g of anthocyanin pigment. The obtained dye did not have any strange taste or odor, and did not change color or fade.
実施例 ２
ムラサキトウモロコシの種実の乾燥粉砕物2000
ｇを抽出タンクに入れ、炭酸ガスを圧入し、該抽
出タンクの外部から水蒸気をもつて加温し、40℃
で昇温させ、超臨界状態に接触させ、油分、揮発
分を抽出相に移行させ、分離タンクに導いた。分
離タンクは温度を50℃に上げ、抽出物を分離除去
した後、炭酸ガスを降温し、更にもとの系に戻し
再使用した。Example 2 Dry and crushed purple corn seeds 2000
Put g into an extraction tank, pressurize carbon dioxide gas, heat it with steam from outside the extraction tank, and heat it to 40℃.
The temperature was raised to bring it into contact with a supercritical state, and the oil and volatile components were transferred to the extraction phase, which was then led to a separation tank. The temperature of the separation tank was raised to 50°C, the extract was separated and removed, and then the carbon dioxide gas was cooled down and returned to the original system for reuse.
抽出タンクの残留分を取り出し、クエン酸１
ｇ、50容量％エタノール水20を添加し、これを
等温下で３時間撹拌した後、過、減圧濃縮して
色素成分約70ｇを得た。このようにして得たムラ
サキトウモロコシ色素は異味異臭がまつたくなく
透明にとけた。 Remove the residue from the extraction tank and add citric acid 1
After adding 20 g of 50 volume % ethanol water and stirring this for 3 hours under isothermal conditions, the mixture was filtered and concentrated under reduced pressure to obtain about 70 g of the pigment component. The purple corn pigment thus obtained was transparent and melted without any unpleasant taste or odor.
実施例 ３
コチニール色素粗抽出液２と炭酸ガスを抽出
タンク内において超臨界状態（40〜50℃／100〜
150Kg／cm）で接触させた。分離タンクにあらか
じめ活性炭100ｇを詰め、色素液中の油分、香気
成分を炭酸ガス液と共に分離タンクに排出し、活
性炭で吸着除去した。Example 3 Cochineal pigment crude extract 2 and carbon dioxide gas were brought into a supercritical state (40~50℃/100~
150Kg/cm). A separation tank was filled with 100 g of activated carbon in advance, and the oil and aroma components in the pigment liquid were discharged into the separation tank along with the carbon dioxide gas liquid, where they were adsorbed and removed by the activated carbon.
抽出タンクに残留した色素を取り出し、水１
を加え、この色素を限外過膜（分画分子量
8000）で10Kg／cm2の条件で更に濃縮して約100ｇ
の色素濃縮液を得た。得た色素濃縮液は非常に澄
明で異味異臭がなかつた。 Remove the remaining pigment from the extraction tank and add 1 part of water.
and pass this dye through an ultrafiltration membrane (molecular weight cutoff).
8000) and further concentrated to approximately 100g under the condition of 10Kg/ cm2 .
A dye concentrate was obtained. The obtained dye concentrate was very clear and had no unusual taste or odor.
Claims (1)
を抽出タンクに入れ、これに炭酸ガス、エチレン
およびプロパンからなる群から選ばれた少なくと
も１種を圧入し、タンク内が超臨界状態になるよ
うに加熱し、原料中の油脂分、香気成分、水分の
一部を抽出相に移行させて抽出除去し、得られた
抽出残である液状ないし固状部に、水または、ア
ルコールまたは有機酸の水溶液を添加し、抽出残
中に含有される色素成分を水または、アルコール
または有機酸の水溶液に移行させ、該水溶液より
色素を得ることを特徴とする水溶性食用色素の製
造法。 ２ 色素がアントシアニン系、キノン系、フラボ
ノイド系、ベタシアニン系、フラボン系、アザフ
イロン系、フイコシアニン系、カロチノイド系か
らなる群から選ばれた少なくとも１種の色素であ
る請求項１記載の製造法。[Claims] 1. A raw material containing a water-soluble, non-lipophilic pigment is placed in an extraction tank, and at least one member selected from the group consisting of carbon dioxide, ethylene, and propane is pressurized into the tank. The mixture is heated so that the inside becomes supercritical, and part of the fats, oils, aroma components, and moisture in the raw materials are transferred to the extraction phase and removed, and the resulting extraction residue, which is a liquid or solid part, is A water-soluble edible product characterized by adding water or an aqueous solution of alcohol or organic acid to transfer the pigment component contained in the extraction residue to water or an aqueous solution of alcohol or organic acid to obtain the pigment from the aqueous solution. Method of manufacturing pigments. 2. The production method according to claim 1, wherein the pigment is at least one type of pigment selected from the group consisting of anthocyanin, quinone, flavonoid, betacyanin, flavone, azaphyron, phycocyanin, and carotenoid pigments.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59033112A JPS60176562A (en) | 1984-02-22 | 1984-02-22 | Production of water-soluble food dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59033112A JPS60176562A (en) | 1984-02-22 | 1984-02-22 | Production of water-soluble food dye |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60176562A JPS60176562A (en) | 1985-09-10 |
| JPH0448420B2 true JPH0448420B2 (en) | 1992-08-06 |
Family
ID=12377566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59033112A Granted JPS60176562A (en) | 1984-02-22 | 1984-02-22 | Production of water-soluble food dye |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60176562A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6336803A (en) * | 1986-07-31 | 1988-02-17 | Seitetsu Kagaku Co Ltd | Treatment of expandable material |
| JPS63258558A (en) * | 1987-04-16 | 1988-10-26 | Mori Seiyu Kk | Extraction and separation of red pepper essence, hot essence and red dyestuff from fed pepper |
| JP4510230B2 (en) | 2000-05-26 | 2010-07-21 | 三栄源エフ・エフ・アイ株式会社 | Deodorized safflower yellow |
| CN1276954C (en) | 2000-05-26 | 2006-09-27 | 三荣源有限公司 | Deodorized colorant of cruciferae plant |
| JP5066720B2 (en) * | 2005-04-27 | 2012-11-07 | 国立大学法人豊橋技術科学大学 | Quinone profile method using quinone compounds extracted using compressed carbon dioxide |
| DK2725925T3 (en) * | 2011-06-30 | 2021-11-01 | Gallo Winery E & J | PROCEDURE FOR PRODUCTION OF NATURAL CRYSTALLIC DYE AND ASSOCIATED PROCESSING SYSTEM |
-
1984
- 1984-02-22 JP JP59033112A patent/JPS60176562A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60176562A (en) | 1985-09-10 |
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