JPS6322144A - Recovery of caffein absorbed by activated carbon and decaffeination of coffee - Google Patents
Recovery of caffein absorbed by activated carbon and decaffeination of coffeeInfo
- Publication number
- JPS6322144A JPS6322144A JP13355387A JP13355387A JPS6322144A JP S6322144 A JPS6322144 A JP S6322144A JP 13355387 A JP13355387 A JP 13355387A JP 13355387 A JP13355387 A JP 13355387A JP S6322144 A JPS6322144 A JP S6322144A
- Authority
- JP
- Japan
- Prior art keywords
- caffeine
- acid
- activated carbon
- carbon
- coffee
- 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
Links
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 title claims description 92
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims description 80
- 238000011084 recovery Methods 0.000 title description 3
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 claims description 45
- 229960001948 caffeine Drugs 0.000 claims description 45
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 claims description 45
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 23
- 239000005711 Benzoic acid Substances 0.000 claims description 21
- 235000010233 benzoic acid Nutrition 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims description 12
- 229960005215 dichloroacetic acid Drugs 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 47
- 238000000605 extraction Methods 0.000 description 18
- 229960000583 acetic acid Drugs 0.000 description 17
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 10
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 238000003795 desorption Methods 0.000 description 7
- 235000019253 formic acid Nutrition 0.000 description 7
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000004310 lactic acid Substances 0.000 description 5
- 235000014655 lactic acid Nutrition 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
- A23F5/00—Coffee; Coffee substitutes; Preparations thereof
- A23F5/20—Reducing or removing alkaloid content; Preparations produced thereby; Extracts or infusions thereof
- A23F5/22—Reducing or removing alkaloid content from coffee extract
- A23F5/223—Reducing or removing alkaloid content from coffee extract using flocculating, precipitating, adsorbing or complex-forming agents, or ion-exchangers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/12—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1, 3, and 7, e.g. caffeine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Tea And Coffee (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Abstract] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
本発明は酸で処理することによって増量活性炭からカフ
ェインを回収する方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for recovering caffeine from expanded activated carbon by treatment with acid.
文献には酸の溶液を使用するカフェイン−増量活性炭か
らカフェインの回収について発表されたものが多い。東
ドイツ特許第７８５６８号は従来のものより濃縮した酸
を使用して従来使用された弱酸溶液よりかなり良好な抽
出が生じるカフェイン−増量活性炭からのカフェインの
回収に関する。There are many publications in the literature on the recovery of caffeine from caffeine-enhanced activated carbon using acid solutions. East German Patent No. 78,568 relates to the recovery of caffeine from caffeine-enhanced activated carbon using a more concentrated acid than previously used, resulting in a significantly better extraction than the weak acid solutions previously used.
欧州特許出願第４２２９５号は活性炭からカフェインを
除去する手段として氷酢酸の使用に関する。European Patent Application No. 42295 relates to the use of glacial acetic acid as a means of removing caffeine from activated carbon.
同じ出願人の欧州特許出願第７６６２０号には氷酢酸が
実際に最良の結果を有するが安全のために効率の一部を
犠牲にすることおよび濃酢酸溶液を少なく使用すること
が好ましいことを指摘している。European Patent Application No. 76620 of the same applicant points out that glacial acetic acid actually has the best results but sacrifices some efficiency for the sake of safety and that it is preferable to use less concentrated acetic acid solution. are doing.
また欧州特許出願第１２９６０９号はカフェインを回収
するためのギ酸またはギ酸と微量の水との混合液の使用
に関する。この最後の出版物によればギ酸の使用は酢酸
の使用よりかなり良好な抽出結果となっている。しかし
ながらギ酸は多くの欠点を有し、特に非常に揮発性であ
る。European Patent Application No. 129609 also relates to the use of formic acid or a mixture of formic acid and trace amounts of water to recover caffeine. According to this last publication, the use of formic acid gives significantly better extraction results than the use of acetic acid. However, formic acid has a number of drawbacks, especially that it is very volatile.
本発明の目的は上述した従来知られている手段より抽出
効率が極めて良好であり、同時に脱着率が高いカフェイ
ン−増量活性炭からカフェインを回収する方法を提供す
ることである。本発明の他の利点は種々の好適な形態の
詳細な検討から明白となる。An object of the present invention is to provide a method for recovering caffeine from caffeine-enhanced activated carbon, which has a much better extraction efficiency than the conventionally known means described above, and at the same time has a high desorption rate. Other advantages of the invention will become apparent from a detailed consideration of the various preferred forms.
本発明によるカフェイン−増量活性炭からカフェインを
回収する方法は活性炭を式
％式％）
（式中Ｒ，はメチル、ＨまたはＣｊ２であり、Ｒ２は電
子吸収基である）
を有する酸で処理することを特徴とする。The method of recovering caffeine from caffeine-enhanced activated carbon according to the present invention involves treating activated carbon with an acid having the formula %, where R is methyl, H or Cj2, and R2 is an electron absorbing group. It is characterized by
驚くべきことにこれらの酸単独または互いの酸との併用
あるいは他の酸との併用はカフェイン−増量活性炭から
カフェインの除去に優れた結果を生じることが判明した
。この処理は連続向流抽出で行なうことが好ましい。Surprisingly, it has been found that these acids alone or in combination with each other or with other acids produce excellent results in the removal of caffeine from caffeine-enhanced activated carbon. Preferably, this treatment is carried out by continuous countercurrent extraction.
まず好適な形態によればカフェイン−増量活性炭をモノ
および／またはジクロロ酢酸で処理する。According to a preferred embodiment, the caffeine-enhanced activated charcoal is first treated with mono- and/or dichloroacetic acid.
他の好適な形態では本発明は活性炭を上記式のＲＩがメ
チルまたはＨであり、そしてＲ２がＯＨである酸で処理
することを特徴とする。In another preferred form, the invention is characterized in that the activated carbon is treated with an acid of the above formula in which RI is methyl or H and R2 is OH.
モノおよび／またはジクロロ酢酸、乳酸しかもグリコー
ル酸もまた活性炭からカフェインを回収するために特に
適当な手段となり、この手段は焙炒性または揮発性につ
いて問題を生じない。その上これらは極めて高い抽出効
率をもたらす優れた抽出剤であると同時に初期抽出もま
た極めて高く連続向流方法において特に重要であること
が判明した。初期抽出が極めて高いことはカフェイン−
遊離酸と増量活性炭との接触の際存在す、るカフェイン
の比較的大部分がほとんど直ぐに活性炭から遊離される
ことを意味する。これはカフェインから実質的に遊離さ
れる。活性炭が極めて有効な最終抽出を受けることを意
味するため連続向流抽出に有利であることが明白となる
。Mono- and/or dichloroacetic acid, lactic acid and even glycolic acid make particularly suitable means for recovering caffeine from activated carbon, which do not present problems with regard to roastability or volatility. Moreover, they have been found to be excellent extractants leading to very high extraction efficiencies, while also having a very high initial extraction, which is of particular importance in continuous countercurrent processes. The extremely high initial extraction is due to caffeine.
This means that a relatively large proportion of the caffeine present upon contact of the free acid with the bulk activated carbon is liberated from the activated carbon almost immediately. It is substantially freed from caffeine. It becomes clear that activated carbon is advantageous for continuous countercurrent extraction as it means that it undergoes a very efficient final extraction.
さらにその上これらの酸の多くは元々コーヒーに発生す
る。これは処理炭素を再使用する前に熱で再生する必要
がないことを意味する。Furthermore, many of these acids occur naturally in coffee. This means that the treated carbon does not need to be thermally regenerated before being reused.
乳酸は二つの異性体形態で生ずることが観察される。Ｄ
−乳酸、Ｌ−乳酸あるいはその混合物が使用されるかは
本発明に影響を及ぼさない。そのため経済的理由として
ラセミ混合物を使用することが好ましい。Lactic acid is observed to occur in two isomeric forms. D
-Whether lactic acid, L-lactic acid or mixtures thereof are used does not affect the invention. For economic reasons, it is therefore preferable to use racemic mixtures.
特定の好適な形態によれば本発明に従って使用される酸
は、ギ酸、酢酸および／またはプロピオン酸のような他
の酸と混合してよい。According to certain preferred forms, the acids used according to the invention may be mixed with other acids, such as formic acid, acetic acid and/or propionic acid.
本発明による方法は効果のある抽出が１００°Ｃ以上の
温度で行なわれるためにこれらの温度で実施することが
好ましい。しかしながら大気圧以上を使用する必要はな
いが勿論有利であることは明らかである。温度の上限は
臣π界的ではないが、種々の成分が揮発性になり過ぎた
りあるいは崩壊する温度より高くすべきではない。好適
には上限は２００°Ｃを超えずさらに詳細には１５０”
Ｃであり、この温度以上ではさらに有益とはなり得ない
がらである。The process according to the invention is preferably carried out at temperatures above 100 DEG C., since effective extraction takes place at these temperatures. However, it is clear that it is not necessary to use pressures above atmospheric pressure, although it is of course advantageous. The upper limit of temperature is not arbitrary, but should not be higher than the temperature at which the various components become too volatile or decay. Preferably the upper limit does not exceed 200°C, more particularly 150"
C, although it cannot be more beneficial above this temperature.
本発明の別の好適な形態によれば活性炭からカフェイン
を回収するために液体安息香酸を使用する。安息香酸の
高融点１２２℃から考えてもこの薬剤はまず可燃性また
は揮発性に関して酢酸でのような問題がなく、たとえあ
るとしても少ない。According to another preferred form of the invention, liquid benzoic acid is used to recover caffeine from activated carbon. Considering benzoic acid's high melting point of 122° C., this agent does not have the same problems, if any, with acetic acid with regard to flammability or volatility.
さらにその上液体安息香酸は極めて高い抽ユ泗得ること
が可能であり、同時に連続向流法で特に重要である初期
抽出も極めて高い優れた抽出剤であることが判明した。Moreover, liquid benzoic acid has been found to be an excellent extractant, as it is possible to obtain extremely high extraction rates, and at the same time, the initial extraction rate, which is particularly important in continuous countercurrent processes, is also extremely high.
さらに安息香酸の利点は、食品応用に安全な生成物とし
て一般に認められているので微量の安息香酸がなお存在
していても抽出した炭素を問題を生ずることなくコーヒ
ーの脱カフェインに再使用することができるということ
である。A further advantage of benzoic acid is that it is generally recognized as a safe product for food applications, so even if traces of benzoic acid are still present, the extracted carbon can be reused to decaffeinate coffee without any problems. This means that it is possible.
この好適な形態による方法は勿論安息香酸が液体である
温度で実施されるべきである。安息香酸の融点１２２℃
から考えて１３０〜１６０℃の範囲の温度が好ましいが
これ以上あるいは以下の温度も適用できる。しかし低い
温度では加熱が不十分な場合に安息香酸が凝固してしま
い、その結実装置が詰まってしまう危険を伴うため好ま
しくない。１６０℃以上の温度は一般に１６０℃以下の
温度より有益とはならず同時に特定生成物が崩壊する危
険がある。The process according to this preferred form should of course be carried out at a temperature at which the benzoic acid is a liquid. Melting point of benzoic acid: 122℃
Considering this, a temperature in the range of 130 to 160°C is preferable, but temperatures higher or lower than this range are also applicable. However, low temperatures are not preferable because the benzoic acid will solidify if heating is insufficient and there is a risk that the fruiting device will become clogged. Temperatures above 160°C are generally less beneficial than temperatures below 160°C, and at the same time there is a risk that certain products will disintegrate.
安息香酸の比較的低揮発性に関連して大気圧以上で操作
することは必要としない。これは勿論投資およびエネル
ギー消費の観点から有益である。Due to the relatively low volatility of benzoic acid, there is no need to operate above atmospheric pressure. This is of course beneficial from an investment and energy consumption point of view.
本発明によれば記載した酸はそれだけであるいは混和物
として使用される。必要あればギ酸、酢酸および／また
はプロピオン酸との混合物もまた使用することができる
。一般に、記載した酸の濃度は少なくとも５０重量％で
あり、さらに詳しくはそれらは単独で使用され、即ちギ
酸、酢酸および／またはプロピオン酸と使用しない。According to the invention, the acids described are used on their own or as mixtures. If necessary, mixtures with formic acid, acetic acid and/or propionic acid can also be used. In general, the concentrations of the acids mentioned are at least 50% by weight, more particularly they are used alone, ie not with formic acid, acetic acid and/or propionic acid.
指摘した通り、処理は向流で行なうのが好ましく、比較
的短い抽出回数となる。最適な抽出回数および抽出量は
、日常の試験により当業者によって確立することができ
る。活性炭量に対する抽出液体量は非常に有効な抽出の
結果として極めて少量であることができ、一般に増量活
性炭の量に比例して５〜１０倍量の抽出剤で十分である
。これらの量は現状の技術により少なくとも１０〜２０
倍量が必要とされる量よりもかなり低い。勿論大量を本
発明に従って使用することもできるが必要ではない。カ
フェイン−増量炭素は一般に生コーヒーからカフェイン
を除去する方法に由来するものである。かかる方法の具
体例は欧州特許出願第４０７１２号、同第１１１３７５
号および同第８３９８号に記載されている。As pointed out, the treatment is preferably carried out in countercurrent, resulting in a relatively short number of extractions. The optimal number of extractions and amount of extraction can be established by one skilled in the art through routine experimentation. The amount of extraction liquid relative to the amount of activated carbon can be very small as a result of highly effective extraction, and generally 5 to 10 times the amount of extractant is sufficient in proportion to the amount of expanded activated carbon. These amounts are at least 10 to 20 with current technology.
Much lower than the amount required. Of course, large amounts can be used in accordance with the invention, but this is not necessary. Caffeine-added carbon generally comes from the process of removing caffeine from green coffee. Examples of such methods are European Patent Application Nos. 40712 and 111375.
No. 8398.
カフェインを炭素から除去した後、結晶化などの公知の
方法で溶液から除去することができる。After the caffeine is removed from the carbon, it can be removed from the solution by known methods such as crystallization.
溶媒の除去および／または再生後カフェインからほとん
ど完全に遊離した炭素をカフェインの吸収に再使用する
ことができる。After removal of the solvent and/or regeneration, the carbon almost completely liberated from the caffeine can be reused for caffeine absorption.
また本発明は活性炭によってコーヒーを脱カフェインし
た後炭素からカフェインを回収する方法に関し、本発明
による方法を使用して活性炭を処理することを特徴とす
る。The invention also relates to a method for recovering caffeine from carbon after decaffeination of coffee with activated carbon, characterized in that the method according to the invention is used to treat the activated carbon.
本発明をいくつかの実施例によって具体的に説明するが
それらに限定されるものではない。The present invention will be specifically explained by some examples, but is not limited thereto.
実施■土
カフェイン増量４４ ｇ ／ ｋｇ炭素および全乾燥増
量２２５ｇ／ｋｇ炭素を有する市販の活性炭を１２０℃
に加熱したカラムに装填しその後、ジクロロ酢酸量をみ
かけ速度（ｓｕｐｅｒｆｉｃｉａｌ ｖｅｌｏｃｉｔｙ
） ０．４ｗ／ｓｅｃでカラムの上部から底部にポンプ
で注入した。Implementation Commercially available activated carbon with a soil caffeine weight gain of 44 g/kg carbon and a total dry weight weight of 225 g/kg carbon was heated at 120°C.
The amount of dichloroacetic acid was determined by the apparent velocity.
) Pumped from the top to the bottom of the column at 0.4 w/sec.
ジクロロ酢酸を冷却後カフェイン含有量についてＨＰＬ
Ｃによって分析した。炭素は存在するカフェイン量の８
０．８重量％を脱着した。HPL for caffeine content after cooling dichloroacetic acid
Analyzed by C. Carbon is 8% of the amount of caffeine present
0.8% by weight was desorbed.
欧州特許第４２２９５号では氷酢酸を使用して７３％の
値であった。それ故本発明によってかなりの改良が得ら
れたことは明白である。European Patent No. 42295 uses glacial acetic acid with a value of 73%. It is therefore clear that a considerable improvement has been achieved with the present invention.
■および 軒１
実施例Ｉに記載した方法でジクロロ酢酸および酢酸を用
いて１１２°Ｃで実施した。炭素１００ｇを溶媒で処理
し２５ｍ１の最初の２フラクシヨンのカフェイン容凹で
比較した。結果を表に列挙する。■ and Eaves 1 Performed as described in Example I using dichloroacetic acid and acetic acid at 112°C. 100 g of carbon was treated with the solvent and the caffeine content of the first two fractions of 25 ml was compared. List the results in a table.
１ １６、３ ２６
．６２ １３、８
１７．５これらのデータは本発明によって優れた初期抽
出が得られることを明白に示している。1 16, 3 26
．． 62 13, 8
17.5 These data clearly demonstrate that the present invention provides excellent initial extraction.
土較炭
酢酸による脱着
還流冷却伸５００ｎ＋ｉ！の丸底フラスコにカフェイン
で予め増量した市販の炭素１００ｇ （炭素８１．７ｇ
）および他の成分を酢酸によって脱着した。酢酸を繰り
返し傾瀉することによって脱着し、その後再び純粋な酢
酸を添加した。１回の充填につき還流時間は１１８℃で
３０〜４０分であった。Desorption reflux cooling elongation with carbonacetic acid 500n+i! 100 g of commercially available carbon (81.7 g of carbon) pre-bulked with caffeine into a round bottom flask
) and other components were desorbed by acetic acid. Acetic acid was desorbed by repeated decanting and then pure acetic acid was added again. Reflux time was 30-40 minutes at 118°C per charge.
結果は表Ａに列挙する。The results are listed in Table A.
実上五ｌ
安息香酸による脱着
攪拌器付５ＱＯｎ＋ｊ！の丸底フラスコにカフェインで
予め増量した市販の炭素１００ｇ （炭素８１．７ｇ
）および他の成分を安息香酸によって脱着した。Practically 5l 5QOn+j with benzoic acid desorption stirrer! 100 g of commercially available carbon (81.7 g of carbon) pre-bulked with caffeine into a round bottom flask
) and other components were desorbed by benzoic acid.
融解形態の純粋な安息香酸を再び添加した後、融解した
安息香酸を繰り返し傾瀉することによって脱着を行ない
、その後融解状の純粋な安息香酸を再び添加した。１回
の充填につき攪拌時間は１５０℃で３０〜４０分であっ
た。画分を冷却後カフェインに対して分析した。安息香
酸の水での溶解度はわずか２．９ｇ／ｋｇである。次い
で安息香酸中のカフェイン量はもはや検出することがで
きない。After addition of pure benzoic acid in molten form again, desorption was carried out by repeated decanting of the molten benzoic acid, after which pure benzoic acid in molten form was added again. Stirring time was 30-40 minutes at 150°C per charge. Fractions were analyzed for caffeine after cooling. The solubility of benzoic acid in water is only 2.9 g/kg. The amount of caffeine in the benzoic acid can then no longer be detected.
安息香酸試料中のカフェイン分析としては１ｇ試料を秤
量し、酢酸で２５ｍ１に溶解した。カフェイン含有量を
この溶液で定量する。結果は表Ｂに列挙する。For analysis of caffeine in benzoic acid samples, 1 g sample was weighed and dissolved in 25 ml with acetic acid. The caffeine content is determined in this solution. The results are listed in Table B.
酸の傾瀉量の関数としてカフェイン濃度の変化を第１お
よび２図にグラフで表わす。第３図は傾瀉した酸の全量
に対する酸の傾瀉量％の関数として脱着カフェイン％の
グラフである（ａ線は酢酸であり、ｂＮＩＡは安息香酸
である）。The variation in caffeine concentration as a function of the amount of acid decant is graphically represented in Figures 1 and 2. FIG. 3 is a graph of % caffeine desorbed as a function of % acid decanted relative to the total amount of decanted acid (a line is acetic acid, bNIA is benzoic acid).
一定の処理条件下では安息香酸で行ったカフェイン脱着
は酢酸での脱着より良好な結果となる。Under certain processing conditions, caffeine desorption performed with benzoic acid gives better results than desorption with acetic acid.
安息香酸では脱着率８９．１％が得られ、酢酸では８１
．６％であった。A desorption rate of 89.1% was obtained with benzoic acid, and 81% with acetic acid.
．． It was 6%.
爽施厨立
カフェイン増量４４ｇ／ｋｇ炭素を有する市販の活性炭
１００ｇ （非増量炭素８１．６ｇ）を水中乳酸（８５
〜９０％）で、この溶液３１を１００〜１０５℃の温度
を有する炭素カラムの上に（下向き流れ）約４時間ポン
プで注入することによって脱着した。溶離液を多数のフ
ラクションに集め、冷却後カフェインを分析した。結果
を表に列挙する。100g of commercially available activated carbon (81.6g of non-added carbon) containing 44g/kg of added carbon was added to lactic acid in water (85g of carbon).
~90%) and was desorbed by pumping this solution 31 onto a carbon column (downward flow) for approximately 4 hours with a temperature of 100-105°C. The eluate was collected into a number of fractions and analyzed for caffeine after cooling. List the results in a table.
この試験結果を第４図に示す。The test results are shown in FIG.
去隻拠茎
欧州特許出願第１１１３７５号に記載される方法を使用
して生コーヒーを脱カフェインした。次いでカフェイン
−増量活性炭を乳酸の９０％水溶液と向流処理にかけた
。良好な収量が得られた。The green coffee was decaffeinated using the method described in European Patent Application No. 111375. The caffeine-enhanced activated carbon was then subjected to countercurrent treatment with a 90% aqueous solution of lactic acid. Good yields were obtained.
第１図及び第２図は酸の傾瀉量の関数としてカフェイン
濃度の変化を表わした図である。
第３図は傾瀉した酸の全量に対する酸の傾瀉量％の関数
として脱カフェイン％を表わした図である。
第４図は実施例■の結果を表わした図である。
晋 ’Ｆ’； （’％Ｉ ’：”
’：” ”＋＋＋１．−− −一 −ｍ−
。
ｎ 〜 〜 −−〇
０ ００ ｃｌ：） （Ｊ Ｌ−−Ｊ −一
−一 −一（：） （７） Ｃｏ ｍ＋ω−４０さ
一μｍ −ゴ Ｃつ （”
Ｊ ｒ手続補正書
昭和６２年８月１８日
特許庁長官 小 川 邦 夫 殿
１、事件の表示 昭和６２年特許願第１３３５５３号
２、発明の名称 活性炭に吸収されたカフェインの回
収方法およびコーヒーの脱カフェイン方法
コ、補正をする者
事件との関係 特許出願人
エイジ − テーハンデル エヌ、ヴエー。
４、代理人
５、補正の対象 （１）「 願 書 」（２）
「委任状」FIGS. 1 and 2 are diagrams showing the change in caffeine concentration as a function of the amount of acid decanting. FIG. 3 is a plot of the % decaffeination as a function of the % amount of acid decanted relative to the total amount of acid decanted. FIG. 4 is a diagram showing the results of Example (2). Jin 'F';('%I':”
':” ”+++1. −− −1 −m−
. n ~ ~ --〇0 00 cl:) (J L--J -1
-1 -1(:) (7) Com+ω-40Sa1μm -Go Ctsu (”
J r Procedural Amendment August 18, 1988 Director General of the Patent Office Kunio Ogawa 1, Indication of Case Patent Application No. 133553 of 1988 2, Title of Invention Method for recovering caffeine absorbed in activated carbon and coffee The relationship between the decaffeination method and the amended case Patent Applicant E.T.N.V. 4. Agent 5. Subject of amendment (1) “Application” (2)
"power of attorney"
Claims (1)
電子吸収基である） を有する化合物で処理することを特徴とする増量炭素を
酸で処理することによってカフェイン−増量活性炭から
カフェインを回収する方法。 ２、Ｒ＿１がメチルであり、Ｒ＿２がＯＨである特許請
求の範囲第１項記載の方法。 ３、Ｒ＿１がＨであり、Ｒ＿２がＣｌ、ＯＨまたはフェ
ニルである特許請求の範囲第１項記載の方法。 ４、Ｒ＿１およびＲ＿２が共にＣｌである特許請求の範
囲第１項記載の方法。 ５、活性炭を酸との向流処理にかける特許請求の範囲第
１〜４項のいずれか１項に記載の方法。 ６、モノおよび／またはジクロロ酢酸を使用する特許請
求の範囲第３または４項記載の方法。 ７、活性炭を１００℃以上の温度で処理する特許請求の
範囲第１〜６項のいずれか１項に記載の方法。 ８、液体安息香酸を使用する特許請求の範囲第３項記載
の方法。 ９、活性炭を少なくとも１３０℃の温度で処理する特許
請求の範囲第８項記載の方法。 １０、炭素を１６０℃以下の温度で処理する特許請求の
範囲第８または９項記載の方法。 １１、得られた溶液から結晶化によってカフェインを回
収する特許請求の範囲第１〜１０項のいずれか１項に記
載の方法。 １２、前述の特許請求の範囲のいずれかの項記載の方法
を使用してカフェインを回収することを特徴とする活性
炭によってコーヒーを脱カフェインした後カフェインを
回収する方法。[Claims] 1. Treating activated carbon with a compound having the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (wherein R_1 is methyl, H or Cl, and R_2 is an electron absorbing group) Caffeine--A method for recovering caffeine from expanded activated carbon by treating the expanded carbon with an acid. 2. The method according to claim 1, wherein R_1 is methyl and R_2 is OH. 3. The method according to claim 1, wherein R_1 is H and R_2 is Cl, OH or phenyl. 4. The method of claim 1, wherein R_1 and R_2 are both Cl. 5. The method according to any one of claims 1 to 4, in which activated carbon is subjected to countercurrent treatment with an acid. 6. The method according to claim 3 or 4, in which mono- and/or dichloroacetic acid is used. 7. The method according to any one of claims 1 to 6, wherein activated carbon is treated at a temperature of 100°C or higher. 8. The method according to claim 3, which uses liquid benzoic acid. 9. The method of claim 8, wherein the activated carbon is treated at a temperature of at least 130°C. 10. The method according to claim 8 or 9, wherein carbon is treated at a temperature of 160° C. or lower. 11. The method according to any one of claims 1 to 10, wherein caffeine is recovered from the obtained solution by crystallization. 12. A method for recovering caffeine after decaffeinating coffee with activated carbon, characterized in that the caffeine is recovered using a method according to any of the preceding claims.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8601400 | 1986-05-30 | ||
| NL8601400A NL8601400A (en) | 1986-05-30 | 1986-05-30 | PROCESS FOR THE COLLECTION OF CAFFEINE ABSORBED FROM ACTIVE CARBON. |
| NL8601401 | 1986-05-30 | ||
| NL8601783 | 1986-07-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6322144A true JPS6322144A (en) | 1988-01-29 |
Family
ID=19848095
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13355487A Pending JPS6322145A (en) | 1986-05-30 | 1987-05-30 | Decaffeination of raw coffee |
| JP13355387A Pending JPS6322144A (en) | 1986-05-30 | 1987-05-30 | Recovery of caffein absorbed by activated carbon and decaffeination of coffee |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13355487A Pending JPS6322145A (en) | 1986-05-30 | 1987-05-30 | Decaffeination of raw coffee |
Country Status (2)
| Country | Link |
|---|---|
| JP (2) | JPS6322145A (en) |
| NL (1) | NL8601400A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002119352A (en) * | 2000-10-13 | 2002-04-23 | Aisin Seiki Co Ltd | Reclining device |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01312986A (en) * | 1988-06-13 | 1989-12-18 | Matsushita Electric Ind Co Ltd | Taste-improving bag for beverage |
| JP4667317B2 (en) * | 2005-07-29 | 2011-04-13 | 花王株式会社 | Method for producing coffee composition |
| JP2011000129A (en) * | 2010-10-04 | 2011-01-06 | Ajinomoto General Foods Inc | Chlorogenic acid compound-containing drink |
| GB201405488D0 (en) | 2014-03-26 | 2014-05-07 | Infre S A | Decaffeination methods and systems |
| RU2746120C2 (en) * | 2016-05-19 | 2021-04-07 | Декафино, Инк. | Caffeine-absorbing material, caffeine-absorbing system, decaffeination system, and related methods for removing caffeine from solutions |
-
1986
- 1986-05-30 NL NL8601400A patent/NL8601400A/en not_active Application Discontinuation
-
1987
- 1987-05-30 JP JP13355487A patent/JPS6322145A/en active Pending
- 1987-05-30 JP JP13355387A patent/JPS6322144A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002119352A (en) * | 2000-10-13 | 2002-04-23 | Aisin Seiki Co Ltd | Reclining device |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6322145A (en) | 1988-01-29 |
| NL8601400A (en) | 1987-12-16 |
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