JPS63230068A - Recover of esters from fermentation gas - Google Patents
Recover of esters from fermentation gasInfo
- Publication number
- JPS63230068A JPS63230068A JP62064286A JP6428687A JPS63230068A JP S63230068 A JPS63230068 A JP S63230068A JP 62064286 A JP62064286 A JP 62064286A JP 6428687 A JP6428687 A JP 6428687A JP S63230068 A JPS63230068 A JP S63230068A
- Authority
- JP
- Japan
- Prior art keywords
- esters
- zeolite
- recovery
- adsorption
- fermentation process
- 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.)
- Granted
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 27
- 238000000855 fermentation Methods 0.000 title claims abstract description 17
- 230000004151 fermentation Effects 0.000 title claims abstract description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 38
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 26
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000010457 zeolite Substances 0.000 claims abstract description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 15
- -1 organosilane compound Chemical class 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 17
- 229910000077 silane Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003463 adsorbent Substances 0.000 abstract description 8
- 229910052681 coesite Inorganic materials 0.000 abstract description 7
- 229910052906 cristobalite Inorganic materials 0.000 abstract description 7
- 229910052682 stishovite Inorganic materials 0.000 abstract description 7
- 229910052905 tridymite Inorganic materials 0.000 abstract description 7
- 125000003118 aryl group Chemical group 0.000 abstract description 6
- 235000012239 silicon dioxide Nutrition 0.000 abstract description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052593 corundum Inorganic materials 0.000 abstract description 2
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 229910001845 yogo sapphire Inorganic materials 0.000 abstract description 2
- 230000001476 alcoholic effect Effects 0.000 abstract 2
- 238000003795 desorption Methods 0.000 abstract 1
- 238000011084 recovery Methods 0.000 description 20
- 238000001179 sorption measurement Methods 0.000 description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
- 239000007789 gas Substances 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- 239000001760 fusel oil Substances 0.000 description 5
- RGXWDWUGBIJHDO-UHFFFAOYSA-N ethyl decanoate Chemical compound CCCCCCCCCC(=O)OCC RGXWDWUGBIJHDO-UHFFFAOYSA-N 0.000 description 4
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 235000013355 food flavoring agent Nutrition 0.000 description 3
- 229940117955 isoamyl acetate Drugs 0.000 description 3
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 3
- 229910052680 mordenite Inorganic materials 0.000 description 3
- WJTCHBVEUFDSIK-NWDGAFQWSA-N (2r,5s)-1-benzyl-2,5-dimethylpiperazine Chemical compound C[C@@H]1CN[C@@H](C)CN1CC1=CC=CC=C1 WJTCHBVEUFDSIK-NWDGAFQWSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- YYZUSRORWSJGET-UHFFFAOYSA-N octanoic acid ethyl ester Natural products CCCCCCCC(=O)OCC YYZUSRORWSJGET-UHFFFAOYSA-N 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910001657 ferrierite group Inorganic materials 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FPLYNRPOIZEADP-UHFFFAOYSA-N octylsilane Chemical group CCCCCCCC[SiH3] FPLYNRPOIZEADP-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Distillation Of Fermentation Liquor, Processing Of Alcohols, Vinegar And Beer (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
イ０発明の目的
産業上の利用分野
この発明は、アルコール１１！酵工程から発生するガス
から、芳香成分として知られているエステル類を選択的
に回収する方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION A.Objective of the Invention Industrial Application Field This invention is directed to alcohol 11! This invention relates to a method for selectively recovering esters, which are known as aromatic components, from gases generated during fermentation processes.
日本酒を例にとると、醗酵工程から発生するガスには、
エタノールの他に、アルデヒド、酢酸エチル、フーゼル
油（インアミルアルコール、イソブチルアルコールなど
が主成分）、酢酸イソブチル、酢酸イソアミル、カプロ
ン酸エチル、カプリル酸エチル、カプリン酸エチルなど
が含まれている。Taking Japanese sake as an example, the gases generated during the fermentation process include:
In addition to ethanol, it contains aldehydes, ethyl acetate, fusel oil (mainly consisting of inamyl alcohol and isobutyl alcohol), isobutyl acetate, isoamyl acetate, ethyl caproate, ethyl caprylate, and ethyl caprate.
この中で吟醸香といわれているのは、酢酸イソアミル、
カプロン酸エチル、カプリル酸エチル、カプリン酸エチ
ルなどの果実様の芳香を持つエステル類である。Among these, the one called Ginjoka is isoamyl acetate,
These are esters with fruity aromas such as ethyl caproate, ethyl caprylate, and ethyl caprate.
１１本酒の付番又は天然香料として望まれているのはこ
れらのエステル類であり、アルデヒドやフーゼル油は望
ましくない成分である。It is these esters that are desired as flavoring agents or natural flavoring agents for sake, while aldehydes and fusel oils are undesirable components.
本９．１ｊｌの方法では希望する芳香成分（エステル類
）のみを選択的に回収でき、酒に戻せば酒質の向りに役
立ち、又、天然香料としての玉売も可能である。The method described in 9.1jl allows selective recovery of only the desired aroma components (esters), which helps improve the quality of sake when returned to sake, and can also be sold as a natural flavoring agent.
又迷Ｊと皮潰
従来の醗酵ガスの回収法は、醗酵槽から気化発生するエ
タノールの回収を主目的としており、冷却トラップ法と
か、活性炭ＪＲ誰による吸着法とか知られている。Conventional fermentation gas recovery methods are mainly aimed at recovering ethanol vaporized from the fermentation tank, and known methods include the cold trap method and the activated carbon adsorption method.
冷却トラップ法は、醗酵ガスを冷却器に導き、＝２５℃
位に冷却してガス中に含まれるエタノール、フーゼル油
、エステル類を液化し醗酵槽に戻す方法で、もともとエ
タノールの減失防市を目的として広〈実施されている。In the cold trap method, fermentation gas is guided into a cooler and heated to 25°C.
It is a method in which the ethanol, fusel oil, and esters contained in the gas are liquefied by cooling the gas to a certain temperature and returned to the fermentation tank.This method was originally widely implemented with the aim of preventing ethanol loss and loss.
この方法では、アセトアルデビド、フーゼル油等、酒の
香気としては好ましくなく、又役立たない成分も同時に
回収され、かつ芳香成分（エステル類）の濃度は２００
０ｐ ｐ ｍ程度である。In this method, components that are undesirable and useless for the aroma of alcoholic beverages, such as acetaldehyde and fusel oil, are also recovered, and the concentration of aromatic components (esters) is 200%.
It is about 0 ppm.
活性炭素繊維による吸着法は、ひとつには省エネルギー
的なアルコール回収法として、又ひとつには香気成分の
選択回収を目的として開発中のものであるが、文献［１
％ｆ造協会誌第８１ａ第３号、Ｐ１８５〜１８６ （１
９８６）］データによるとアルコール回収法としては優
れているものの、フーゼル油が回収液側に残ってしまい
、香気成分の選択回収という点では満足のゆくものでは
ない。The adsorption method using activated carbon fibers is currently under development, firstly as an energy-saving alcohol recovery method, and secondly for the selective recovery of aroma components, but it is currently being developed in the literature [1].
%f Construction Association Journal No. 81a No. 3, P185-186 (1
According to the data, although this method is excellent as an alcohol recovery method, fusel oil remains in the recovery liquid, making it unsatisfactory in terms of selective recovery of aroma components.
発明が解決しようとする問題点
本発明は、アルコール！９！酵二［程から発生するガス
より、芳香成分として知られているエステル類のみを選
択的に効率よ〈回収する方法を提供することを目的とす
る。Problems to be Solved by the Invention This invention solves the problem of alcohol! 9! The purpose of this invention is to provide a method for selectively and efficiently recovering only esters, which are known as aromatic components, from the gas generated during the fermentation process.
口１発明の構成
問■点を解決するための一段
本発明による醗酵ガスよりエステル類を回収する方法は
、アルコール醗酵工程から発生するガス又はその液化物
を、脱アルミニウム処理してＳｉ０２ ／ Ａ ｆＬ
２０ ａモル比を１０以上としたＹ型ゼオライト、ペン
タシル型ハイシリカゼオライトおよびＣＩ４〜Ｃ２０の
アルキル基を少なくとも１個有する有機シラン化合物で
処理した改質シリカよりなる群から選ばれる吸着剤に接
触させた後、吸着した成分を脱着することを特徴とする
。1. Constituent Structure of the Invention One step to solve the problem (2) The method of recovering esters from fermentation gas according to the present invention is to dealuminize the gas generated from the alcohol fermentation process or its liquefied product to form Si02/AfL.
Contact with an adsorbent selected from the group consisting of Y-type zeolite, pentasil-type high-silica zeolite, and modified silica treated with an organic silane compound having at least one alkyl group of CI4 to C20 with a molar ratio of 10 or more. After that, the adsorbed components are desorbed.
脱アルミニウム処理したＹ型ゼオライト又はペンタシル
型ハイシリカゼオライトは、Ｈイオン交換型でも、又は
金属イオンで交換したゼオライトでもよい０回収した成
分を食品に加えることを考えると、金属イオン交換ゼオ
ライトとしては、無害なＮ ａ 、 Ｋ 、 Ｍ ｇ
、 Ｃａなどのアルカリ金属又はアルカリ土類金属とイ
オン交換したものが好ましい。Dealuminated Y-type zeolite or pentasil-type high-silica zeolite may be H ion-exchanged zeolite or metal ion-exchanged zeolite. Considering that the recovered components are added to foods, metal ion-exchanged zeolite is Harmless N a , K , M g
, Those ion-exchanged with alkali metals or alkaline earth metals such as Ca are preferable.
脱アルミニウム処理したＹ型ゼオライトのＳｉ０２ ／
Ａ Ｊｌ ２０ ｓモル比をｌＯ以りとするのは。Dealuminated Y-type zeolite Si02 /
A Jl 20 What is the reason for making the s molar ratio greater than 1O?
これ以下では選択性がないということではなく、吸着量
が非常に小さくなり実用的でないからである。This is not because there is no selectivity below this range, but because the amount of adsorption becomes extremely small and is not practical.
ペンタシル型ハイシリカゼオライトとしては、ＺＳＭ−
５が代表的なものである。As a pentasil type high silica zeolite, ZSM-
5 is representative.
一般にゼオライトのＳ ｉ ０２ ／Ａｌｚ Ｏｓモル
比を高くすれば疎水性になることと、疎水性の高い化合
物はどこれらのゼオライトへの吸着力が強いことから、
疎水性が一つの因子であることは間違いない、しかしＳ
ｉ ０２ ／ＡＪ１２ Ｏｓモル比が高くてもモルデ
ナイトやフェリエライトには殆ど吸着能が見られないこ
とから、疎水性だけでは説明できない。In general, increasing the S i 02 /Alz Os molar ratio of zeolite makes it hydrophobic, and compounds with high hydrophobicity have a strong adsorption power to zeolite.
Hydrophobicity is definitely a factor, but S
Even if the i 02 /AJ12 Os molar ratio is high, mordenite and ferrierite show almost no adsorption ability, so hydrophobicity alone cannot explain this.
シリカとしてはＣ１４〜Ｃ２０のアルキル基を少なくと
も１個有する有機シラン化合物で表面処理した改質シリ
カを用いる。シリカをＣＩ２以下のアルキル基を有する
有機シラン化合物で処理した場合にはエステル類の吸着
力が弱くエステル類の回収率が低い。またＣ ２０より
も大きいアルキル基を有する有機シラン化合物で処理し
た場合は吸着性の点では問題ないがコスト高となる。As the silica, modified silica whose surface is treated with an organic silane compound having at least one C14 to C20 alkyl group is used. When silica is treated with an organic silane compound having an alkyl group of CI2 or less, the adsorption power for esters is weak and the recovery rate of esters is low. Furthermore, when treated with an organic silane compound having an alkyl group larger than C 20 , there is no problem in terms of adsorptivity, but the cost increases.
アルコール醗酵工程から発生するガスは、ガス状のまま
前記ゼオライトやシラン改質シリカに接触させてもよく
、また冷却法や活性炭（又は活性炭素繊維）であらかじ
め液状で回収したものを前記ゼオライ］・やシラン改質
シリカに接触させてもよい。The gas generated from the alcohol fermentation process may be brought into contact with the zeolite or silane-modified silica in its gaseous state, or it may be collected in a liquid state using a cooling method or activated carbon (or activated carbon fiber) and then used as the zeolite. or silane-modified silica.
吸着条件は室温、常圧でよい。Adsorption conditions may be room temperature and normal pressure.
吸着装置はバッチ式、充填塔式のいずれでもよい、しか
し経済性では充填塔式が右利である。The adsorption device may be either a batch type or a packed column type, but the packed column type is more economical.
上記ゼオライトやシラン改質シリカに選択的に吸着され
たエステル類は、エタノール等の有機溶媒や水蒸気など
で処理することにより容易に脱着される。The esters selectively adsorbed on the zeolite or silane-modified silica are easily desorbed by treatment with an organic solvent such as ethanol, water vapor, or the like.
実施例１
［脱アルミニウム処理Ｙ型ゼオライ！・によるエステル
の回収］
１１本酒醗酵ガスを冷却捕集した液（エタノール４８ｖ
ｏ１％）を水で２倍に希釈した。この溶液１００ｃｃに
、脱アルミニウム処理したＹ型ゼオライト（Ｓ ｆ ０
２ ／Ａｌ２Ｏ３モル比１４及び１２０のもの）Ｉｇを
加え、密閉容器中で１時間室温で攪拌した（吸着工程）
。Example 1 [Dealuminated Y-type zeolite!・Recovery of ester] 11 A liquid obtained by cooling and collecting sake fermentation gas (ethanol 48v
o1%) was diluted 2 times with water. To 100 cc of this solution, dealuminated Y-type zeolite (S f 0
2/Al2O3 molar ratios of 14 and 120) Ig was added and stirred at room temperature for 1 hour in a closed container (adsorption step).
.
同様にして、脱アルミニウム処理したＮａＹ型ゼオライ
ト（ＳｉＯ２／Ａ２２０３モル比１４のもの）、脱アル
ミニウム処理したＣａＹ型ゼオライト（Ｓ ｉ ０２
／Ａｎ２０３モル比１４も））ニついて吸着処理を行っ
た。Similarly, dealuminated NaY-type zeolite (SiO2/A2203 molar ratio 14), dealuminated CaY-type zeolite (S i 02
/An203 molar ratio of 14) was also subjected to adsorption treatment.
濾過後、吸着剤を回収し、６０ｖｏ立％のアルコール２
０ｃｃ中に加えて１時間室温で撹拌した（回収工程）。After filtration, the adsorbent was collected and added with 60% alcohol 2
The mixture was added to 0 cc and stirred at room temperature for 1 hour (recovery step).
濾過後、濾液を回収した。After filtration, the filtrate was collected.
吸着工程、回収工程の各濾液をガスクロ分析して原料中
に含まれる各成分の変化を測定した結果を第１表に示し
た０表より酢酸イソアミル、０４〜ＣＢカルボン酸エチ
ルが良く吸着され、かつ回収も容易なことがｒ（る、な
お、ＳｉＯ２／Ａ２２０３モル比が高いとｉ−アミルア
ルコールの回収が増え、一方０６〜Ｃ８カルボン酸エチ
ルは回収されにくくなる傾向が、認められる。The results of gas chromatography analysis of each filtrate from the adsorption step and recovery step to measure changes in each component contained in the raw materials are shown in Table 1. From Table 0, isoamyl acetate and 04-CB ethyl carboxylate were well adsorbed. Furthermore, it is recognized that when the SiO2/A2203 molar ratio is high, the recovery of i-amyl alcohol increases, while ethyl 06-C8 carboxylate tends to be difficult to recover.
（以下余白）
実施例２
［ペンタシル型ハイシリカゼオライトによるエステルの
回収］
吸着剤としてペンタシル型ハイシリカゼオライトＺｓＭ
−５（Ｓ ｉｏ２／Ａｌ２Ｏｓ ％ル比７゜及び５００
のもの）を使用した以外は実施例１と同じ方法で吸着、
回収を行なった。１！液の分析値を第２表に示した０表
より、芳香成分を良く吸着し、かつ回収できることが判
る。ただし実施例１のゼオティトに比較すると、０６〜
Ｃ８カルボン酸のエステルの回収量はやや少ない。(Left below) Example 2 [Recovery of ester using pentasil-type high-silica zeolite] Pentasil-type high-silica zeolite ZsM as an adsorbent
-5 (Sio2/Al2Os% ratio 7° and 500
Adsorption was carried out in the same manner as in Example 1, except that the
Collection was carried out. 1! From the analysis values of the liquid shown in Table 2, it can be seen that the aromatic components can be well adsorbed and recovered. However, compared to Zeotito in Example 1, 06~
The amount of C8 carboxylic acid ester recovered is rather small.
実施例３
［シラン改質シリカによるエステルの回収］吸着剤とし
てオクタドデシルシラン、テトラドナシルシランでそれ
ぞれ改質したシリカを用いた以外は実施例１と同じ方法
で、吸着、再生を行った。各濾液の分析値を：５２表に
示した０表よりフーゼル油成分は殆ど吸着しないこと、
エステルのうち、酢酸エチルの吸着は少ないがその他の
エステルは良く吸着し、回収も容易なことが判る。Example 3 [Recovery of ester using silane-modified silica] Adsorption and regeneration were carried out in the same manner as in Example 1, except that silica modified with octadodecylsilane and tetradonacylsilane was used as the adsorbent. The analytical values for each filtrate are as follows: Table 52 shows that almost no fusel oil components are adsorbed.
Among the esters, ethyl acetate is poorly adsorbed, but other esters are well adsorbed and can be easily recovered.
比較例１
［実施例１及び２以外のゼオライトによるエステルの回
収Ｊ
ゼオライトとしてＹ型ゼオライト（Ｓ ｉ ０２ ／Ａ
文２０３モル比５．８）、モルデナイト（Ｓｉ０２／Ａ
文２０３モル比２０）を使った以外は実施例１と同じ方
法で吸着、回収を行なった。各濾液の分析値を第３表に
示した。表より、脱アルミニウム処理しないＹ型ゼオラ
イト及びＳｉＯ２／Ａｕ２０３モル比が１０より大であ
ってもモルデナイトではエステル成分の吸着面が殆どな
いことが判る。Comparative Example 1 [Recovery of ester using zeolite other than Examples 1 and 2] Y-type zeolite (S i 02 /A
203 molar ratio 5.8), mordenite (Si02/A
Adsorption and recovery were carried out in the same manner as in Example 1, except that 203 mole ratio 20) was used. The analytical values of each filtrate are shown in Table 3. From the table, it can be seen that even when the Y-type zeolite is not dealuminated and the SiO2/Au203 molar ratio is greater than 10, there is almost no adsorption surface for the ester component in mordenite.
比較例２
［活性炭によるエステルの回収］
吸着剤として活性炭（二村化学製、商品名Ｋ）分子篩炭
素（タケダ製薬製 商品名ＭＣＬ）を用いた以外は実施
例１と同じ方法で吸着、回収を行った。各極液の分析値
を第３表に示した。Comparative Example 2 [Recovery of ester using activated carbon] Adsorption and recovery were carried out in the same manner as in Example 1, except that activated carbon (manufactured by Nimura Chemical, trade name K) and molecular sieve carbon (manufactured by Takeda Pharmaceutical, trade name MCL) were used as adsorbents. Ta. The analytical values of each polar liquid are shown in Table 3.
表より、活性炭、分子篩炭素ともに、エステルのほかｉ
−アミルアルコールもかなり吸着し、回収液中のｉ−ア
ミルアルコール濃度が実施例に示した吸着剤にくらべて
かなり高く、ざらにｃ６〜Ｃｓカルボン酸エステルの回
収量が少ない、これは活性炭及び分子篩炭素の吸着力が
強すぎて脱着されないためと思われる。From the table, both activated carbon and molecular sieve carbon, in addition to ester i
-Amyl alcohol is also adsorbed considerably, and the i-amyl alcohol concentration in the recovered liquid is considerably higher than that of the adsorbent shown in the example, and the amount of c6 to Cs carboxylic acid esters recovered is roughly small. This is probably because the adsorption power of carbon is too strong to be desorbed.
比較例３
［改質シリカによるエステルの回収］
吸着剤としてＣ８アルキル基を有するオクチルシランで
改質したシリカを使った以外は実施例１と同じ方法で吸
着１回収を行なった。Comparative Example 3 [Recovery of ester using modified silica] Adsorption 1 recovery was carried out in the same manner as in Example 1 except that silica modified with octylsilane having a C8 alkyl group was used as the adsorbent.
各濾液の分析値を第３表に示した８表より、実施例３に
示した改質シリカにくらべてエステル成分の吸着力が小
さいことが判る。From Table 8 showing the analytical values of each filtrate in Table 3, it can be seen that the adsorption power of the ester component is smaller than that of the modified silica shown in Example 3.
（以下余白）
ハ１発明の効果
実施例から明らかなように、アルコール醗酵工程から発
生するガスから、芳香成分として知られているエステル
類を選択的に回収することができる。(Left below) C1 Effect of the invention As is clear from the examples, esters known as aromatic components can be selectively recovered from the gas generated from the alcohol fermentation process.
Claims (1)
を、脱アルミニウム処理してＳｉＯ＿２／Ａｌ＿２Ｏ＿
３モル比を１０以上としたＹ型ゼオライト、ペンタシル
型ハイシリカゼオライト及びＣ＿１＿４〜Ｃ＿２＿０の
アルキル基を少なくとも１個有する有機シラン化合物で
処理した改質シリカよりなる群から選ばれる吸着剤に接
触させた後、吸着した成分を脱着することを特徴とする
醗酵ガスよりエステル類を回収する方法。The gas generated from the alcohol fermentation process or its liquefied product is dealuminated to form SiO_2/Al_2O_
3 molar ratio of 10 or more, pentasil type high silica zeolite, and modified silica treated with an organic silane compound having at least one alkyl group of C_1_4 to C_2_0. A method for recovering esters from fermentation gas, which is characterized in that the adsorbed components are then desorbed.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62064286A JPS63230068A (en) | 1987-03-20 | 1987-03-20 | Recover of esters from fermentation gas |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62064286A JPS63230068A (en) | 1987-03-20 | 1987-03-20 | Recover of esters from fermentation gas |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63230068A true JPS63230068A (en) | 1988-09-26 |
| JPH0329384B2 JPH0329384B2 (en) | 1991-04-24 |
Family
ID=13253838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62064286A Granted JPS63230068A (en) | 1987-03-20 | 1987-03-20 | Recover of esters from fermentation gas |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63230068A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102742815A (en) * | 2011-04-19 | 2012-10-24 | 丰益(上海)生物技术研发中心有限公司 | Novel method for preparing material having cheese flavor |
-
1987
- 1987-03-20 JP JP62064286A patent/JPS63230068A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102742815A (en) * | 2011-04-19 | 2012-10-24 | 丰益(上海)生物技术研发中心有限公司 | Novel method for preparing material having cheese flavor |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0329384B2 (en) | 1991-04-24 |
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