JPH02109987A - Method for refining sorbic acid - Google Patents
Method for refining sorbic acidInfo
- Publication number
- JPH02109987A JPH02109987A JP26248088A JP26248088A JPH02109987A JP H02109987 A JPH02109987 A JP H02109987A JP 26248088 A JP26248088 A JP 26248088A JP 26248088 A JP26248088 A JP 26248088A JP H02109987 A JPH02109987 A JP H02109987A
- Authority
- JP
- Japan
- Prior art keywords
- sorbic acid
- aqueous liquid
- solvent
- extraction
- sorbic
- 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
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 235000010199 sorbic acid Nutrition 0.000 title claims abstract description 42
- 239000004334 sorbic acid Substances 0.000 title claims abstract description 42
- 229940075582 sorbic acid Drugs 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 18
- 238000007670 refining Methods 0.000 title 1
- 244000005700 microbiome Species 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 239000007788 liquid Substances 0.000 claims abstract description 10
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 4
- 150000002170 ethers Chemical class 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 4
- 150000002576 ketones Chemical class 0.000 claims abstract description 4
- BATOPAZDIZEVQF-MQQKCMAXSA-N (E,E)-2,4-hexadienal Chemical compound C\C=C\C=C\C=O BATOPAZDIZEVQF-MQQKCMAXSA-N 0.000 claims description 10
- BATOPAZDIZEVQF-UHFFFAOYSA-N sorbic aldehyde Natural products CC=CC=CC=O BATOPAZDIZEVQF-UHFFFAOYSA-N 0.000 claims description 10
- 230000001590 oxidative effect Effects 0.000 claims description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 20
- 238000007254 oxidation reaction Methods 0.000 abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- 241000186359 Mycobacterium Species 0.000 abstract description 4
- 239000013078 crystal Substances 0.000 abstract description 4
- 238000000638 solvent extraction Methods 0.000 abstract description 4
- 239000002609 medium Substances 0.000 abstract description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract description 2
- 239000000872 buffer Substances 0.000 abstract description 2
- 239000001963 growth medium Substances 0.000 abstract description 2
- 239000011780 sodium chloride Substances 0.000 abstract description 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 235000002639 sodium chloride Nutrition 0.000 abstract 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 abstract 1
- 238000000605 extraction Methods 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 2
- 241000589220 Acetobacter Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000010241 potassium sorbate Nutrition 0.000 description 2
- 239000004302 potassium sorbate Substances 0.000 description 2
- 229940069338 potassium sorbate Drugs 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- 241000588986 Alcaligenes Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 241000187761 Streptomyces albidoflavus Species 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 125000003180 beta-lactone group Chemical group 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019249 food preservative Nutrition 0.000 description 1
- 239000005452 food preservative Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- -1 quinolene Chemical compound 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229940075554 sorbate Drugs 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
[産業上の利用分野]
本発明はソルブアルデヒドを微生物学的に酸化したソル
ビン酸含有水性液から、核酸を単離する方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method for isolating nucleic acids from an aqueous solution containing sorbic acid obtained by microbiologically oxidizing sorbaldehyde.
[従来の技術]
ソルビン酸あるいはその塩はいずれも抗カビ力が優れて
いるので食品保存剤として賞用されているが、その工業
的な製造法としては通常クロトンアルデヒドとケテンと
を反応させて中間的に形成されたβ−ラクトンを経てそ
のポリエステルを製造し、次いで該ポリエステルを熱分
解、酸分解あるいはイオン交換樹脂分解してソルビン酸
を生成させる方法が実施されている。[Prior art] Sorbic acid or its salts have excellent antifungal properties and are used as food preservatives, but the industrial method for producing them is usually by reacting crotonaldehyde and ketene. A method has been practiced in which the polyester is produced via an intermediately formed β-lactone, and then the polyester is decomposed by thermal decomposition, acid decomposition, or ion exchange resin decomposition to produce sorbic acid.
しかしながら、かかる方法においてはポリエステル分解
後のソルビン酸の回収あるいは精製操作が面倒で工程が
長く、複雑な工程管理を必要とする等製造面、経済面に
おいて必ずしも有利であるとは言えない。However, in such a method, recovery or purification of sorbic acid after polyester decomposition is troublesome, the process is long, and complicated process control is required, so that it cannot necessarily be said to be advantageous in terms of production or economy.
かかる解決策として最近、ソルブアルデヒドを特定の微
生物で処理してソルビン酸を製造する方法が提案され、
又本出願人も特許出願を行っているところである。As a solution to this problem, a method has recently been proposed in which sorbic acid is produced by treating sorbaldehyde with specific microorganisms.
The present applicant is also in the process of filing a patent application.
[発明が解決しようとする課題]
しかしながら、かかる微生物による酸化法で製造される
ソルビン酸含有反応生成液中には、肉エキス、ペプトン
等の培地組成物や微生物の分解で溶出する蛋白質等が不
純物として溶解しているため、この反応系からソルビン
酸を効率良く単離することが工業化への課題とされるが
、・これまでかかる系からのソルビン酸の単離法につい
ては殆ど報告がなされていないのが実情である。[Problems to be Solved by the Invention] However, the sorbic acid-containing reaction product liquid produced by the oxidation method using microorganisms contains impurities such as meat extract, culture medium composition such as peptone, and proteins eluted by microorganism decomposition. Therefore, efficiently isolating sorbic acid from this reaction system is a challenge for industrialization. However, until now, there have been few reports on methods for isolating sorbic acid from such systems. The reality is that there is not.
本発明者等は膜分離、晶析、蒸留法による精製操作につ
いて検討したが、膜分離は膜の目づまり等の作業性の点
で、晶析は得られるソルビン酸の純度の点で、又、蒸留
法は一旦ソルピン酸をメチルエステル等にエステル化す
ることが必要である等の欠点がありいずれも工業的には
採用し難いことが判明した。The present inventors have investigated purification operations using membrane separation, crystallization, and distillation methods, but membrane separation has problems with workability such as clogging of the membrane, and crystallization has problems with purity of the obtained sorbic acid. It has been found that the distillation method has drawbacks such as the need to first esterify sorbic acid into methyl ester, etc., and it is difficult to employ both methods industrially.
[課題を解決するための手段]
しかるに本発明者等はソルブアルデヒドを微生物により
酸化して得られる該ソルビン酸を脂肪族炭化水素、芳香
族炭化水素、ハロゲン含有炭化水素、ケトン類及びエー
テル類の少なくとも1種を用いて溶剤抽出する場合、効
率良くソルビン酸を取得できることを見出し本発明を完
成するに至った。[Means for Solving the Problems] However, the present inventors have determined that the sorbic acid obtained by oxidizing sorbaldehyde with microorganisms can be used to convert sorbic acid into aliphatic hydrocarbons, aromatic hydrocarbons, halogen-containing hydrocarbons, ketones, and ethers. The present inventors have discovered that sorbic acid can be efficiently obtained when at least one of them is used for solvent extraction.
まず本発明ではソルブアルデヒドを微生物で酸化するの
であるが、微生物としては酸化能力のあるらのであれば
いずれも実用出来る。幾つか例示すれば、ミコバクテリ
ウム ロドクロス(Mycobacterium r
hod。First, in the present invention, sorbaldehyde is oxidized by microorganisms, but any microorganism can be used as long as it has oxidizing ability. To name a few, Mycobacterium rhodocross (Mycobacterium r.
hod.
chrous、IFO13161)、aドシュードモナ
ススフエoイド(Rhodopseudomonas
5pberoides、 I FO12203Lスト
レプトミセス アルビドフラバス、(Streptos
yces albidoflavus、 I F
OI 3010 )アセトバクター アセンデンス(A
cetobacter ascendsns% IF
O3188)、アセトバクター バスチュリアヌス サ
ブエスピー ロバニエン(Acetobacter
pasteurianus 5ubsp、 1ova
nien、 I FO13753)、アルカリゲネス
ユートロファス(^lcaligenes eut
r。chrous, IFO13161), a.
5pberoides, I FO12203L Streptomyces albidoflavus, (Streptos
yces albidoflavus, I F
OI 3010) Acetobacter ascendens (A
cetobacter ascendsns% IF
O3188), Acetobacter basturianus subsp.
pasteurianus 5ubsp, 1ova
Nien, I FO13753), Alcaligenes eut
r.
phus、ATCo 17699)等がある。phus, ATCo 17699), etc.
勿論、本発明ではこれらのみに限定されるものではない
。Of course, the present invention is not limited to these.
酸化反応は微生物を培養した培地にソルブアルデヒドを
添加したり、・培地から微生物を集菌し、これを水、食
塩水、バッファー等に分散させた系にソルブアルデヒド
を添加する等任意の方法で実施する。The oxidation reaction can be carried out by any method such as adding sorbaldehyde to a medium in which microorganisms have been cultured, or collecting microorganisms from the medium and adding sorbaldehyde to a system in which they are dispersed in water, saline, buffer, etc. implement.
反応温度は10〜70℃好ましくは20〜40℃、PH
は3〜10好ましくは4〜9、反応時間は0.1〜15
0時間程度時間開から選ばれる。Reaction temperature is 10-70℃, preferably 20-40℃, PH
is 3-10, preferably 4-9, reaction time is 0.1-15
The time is selected from approximately 0 hours.
かかる反応を行ってソルビン酸を含有する水性液を得、
これからソルビン酸を溶剤抽出により単離する。carrying out such a reaction to obtain an aqueous liquid containing sorbic acid,
The sorbic acid is isolated from this by solvent extraction.
上記した如く反応は、通常P H3〜10程度で行われ
、PH調整剤として水酸化ナトリウム、水酸化カルシウ
ム、水酸化カリウム、水酸化マグネシウム等が用いられ
るため、生成したソルビン酸は多くの場合塩の形で系内
に存在する。As mentioned above, the reaction is usually carried out at a pH of about 3 to 10, and sodium hydroxide, calcium hydroxide, potassium hydroxide, magnesium hydroxide, etc. are used as pH adjusters, so the produced sorbic acid is often converted into a salt. exists in the system in the form of
従って、反応後はまず塩酸、硫酸、リン酸等の任意の酸
でソルビン酸塩を中和することが必要である。遊離の酸
の型でソルビン酸か存在する時は必ずしもかかる操作は
必要としない。いずれにしても抽出時には系のP I−
1が4以下となる様にコントロールすることが必要であ
る。Therefore, after the reaction, it is first necessary to neutralize the sorbate with any acid such as hydrochloric acid, sulfuric acid, or phosphoric acid. Such manipulations are not necessarily required when sorbic acid is present in the free acid form. In any case, during extraction, the P I-
It is necessary to control so that 1 becomes 4 or less.
抽出操作は単抽出、並流多段抽出、向流多段抽出等任意
の方式で回分式、連続式いずれも実施可能である。抽出
装置としてはミキサセトラ、多孔板抽出塔、撹拌機付抽
出塔(Mixco塔、5chibel塔等)、スプレー
塔、充填塔、遠心抽出装置(ボドビルニアク抽出装置、
サイクロン型抽出装置)等が挙げられる。The extraction operation can be carried out by any method such as single extraction, parallel current multistage extraction, countercurrent multistage extraction, etc., either batchwise or continuously. Examples of extraction equipment include mixer settlers, perforated plate extraction towers, extraction towers with stirrers (Mixco tower, 5chibel tower, etc.), spray towers, packed towers, centrifugal extraction equipment (Bodobilniak extraction equipment,
cyclone type extraction device), etc.
抽出溶剤としてはへキサン、ヘプタン、オクタン、シク
ロヘキサン等の脂肪族炭化水素、ベンゼン、トルエン、
キンレン、デカリン、メシチレン等の芳香族炭化水素、
クロルベンゼン、ジクロルベンゼン等のハロゲン含有炭
化水素、メチルイソブチルケトン等のケトン類、ジエチ
ルエーテル等のエーテル類が挙げられる。Extraction solvents include aliphatic hydrocarbons such as hexane, heptane, octane, and cyclohexane, benzene, toluene,
Aromatic hydrocarbons such as quinolene, decalin, mesitylene, etc.
Examples include halogen-containing hydrocarbons such as chlorobenzene and dichlorobenzene, ketones such as methyl isobutyl ketone, and ethers such as diethyl ether.
好適な溶媒はトルエンである。A preferred solvent is toluene.
抽出時の温度、抽出溶剤の使用量は特に制限はなく、任
意である。The temperature during extraction and the amount of extraction solvent used are not particularly limited and are arbitrary.
かかる操作によってソルビン酸を含有する有機溶剤溶液
が得られるので、該溶液からソルビン酸を単離する。This operation yields an organic solvent solution containing sorbic acid, from which sorbic acid is isolated.
通常、上記溶液から溶剤を留去すればソルビン酸が晶析
するので常法に従ってが別すれば良い。溶剤の留去時に
水等の共沸剤を添加して効率的な操作を行うことら勿論
可能である。Usually, when the solvent is distilled off from the above solution, sorbic acid will crystallize, so it can be separated according to a conventional method. Of course, this is possible by adding an azeotropic agent such as water during distillation of the solvent to achieve efficient operation.
得られるソルビン酸の結晶はそのままでも充分製品化さ
れ得るが、必要であれば公知の精製が更に実施出来る。The obtained crystals of sorbic acid can be sufficiently commercialized as they are, but if necessary, known purification can be further carried out.
[作 用1
本発明ではソルブアルデヒドを微生物酸化して得られる
ソルビン酸含有反応液から、効率良くソルビン酸を溶剤
抽出することが可能である。[Function 1] In the present invention, it is possible to efficiently extract sorbic acid with a solvent from a sorbic acid-containing reaction solution obtained by microbial oxidation of sorbaldehyde.
[実施例コ 次に実施例を挙げて本発明を更に詳しく説明する。[Example code] Next, the present invention will be explained in more detail with reference to Examples.
(ソルブアルデヒドの酸化)
3Qの反応容器にミコバクテリウム ロドクロス(IF
’0 13161)を乾燥換算で69入れ、P H7、
0,0,1Mリン酸バッファー500m1を加えて菌体
を充分懸濁させた後、ソルブアルデヒドを129添加し
て30℃、24時間振とう下にPHを6.8〜7.1に
維持して反応を行い(P HDJi整に水酸化カリウム
使用)、ソルビン酸カリウム含有水性液(1)を得た。(oxidation of sorbaldehyde) Mycobacterium rhodocross (IF
'0 13161) was added to the dry equivalent of 69, P H7,
After adding 500ml of 0,0,1M phosphate buffer to sufficiently suspend the bacterial cells, sorbaldehyde was added and the pH was maintained at 6.8 to 7.1 at 30°C for 24 hours with shaking. A reaction was carried out (potassium hydroxide was used for PHDJi preparation) to obtain an aqueous solution containing potassium sorbate (1).
(この反応を2回行って所定量のソルビン酸反応液を製
造した。)同様の反応を微生物を代えて行い以下のソル
ビン酸含有水性液を得た。(This reaction was carried out twice to produce a predetermined amount of sorbic acid reaction solution.) A similar reaction was carried out using different microorganisms to obtain the following sorbic acid-containing aqueous solution.
ルエン2209で抽出し分岐後、トルエン層を分取した
。After extraction with toluene 2209 and branching, the toluene layer was separated.
トルエン溶液に水をtsoy加え100+u+Hg以下
で濃縮を行いトルエンを全部留去しソルビン酸の水性懸
濁液を得た。Water was added to the toluene solution and concentrated under 100+U+Hg, and all of the toluene was distilled off to obtain an aqueous suspension of sorbic acid.
該懸濁液からソルビン酸の結晶を炉別し、乾燥した。Sorbic acid crystals were separated from the suspension and dried.
ソルビン酸23.99<回収率 97%)が得られた。Sorbic acid of 23.99% (recovery rate 97%) was obtained.
実施例2〜15
実施例1に準じて種々の抽出溶媒を用いて実験を行った
。その結果を表に示す。Examples 2 to 15 Experiments were conducted according to Example 1 using various extraction solvents. The results are shown in the table.
実施例1
ソルビン酸カリウム32gを含有する水性液1000g
100O,8)に36%酢酸を25m1加え、PHを2
〜3に調整し75℃に加熱した。該温度でこの水性液を
ト手続補正書
■、事件の表示
昭和63年特許願第262480号
2、発明の名称
ソルビン酸の精製方法
3、補正をする者
事件との関係 特許出願人
住 所 大阪市北区野崎町9番6号(郵便番号530)
[効 果]
本発明では特定の溶剤を用いて抽出することによって、
ソルビン酸含有水性液からソルビン酸を効率良(単離出
来る。Example 1 1000 g of aqueous liquid containing 32 g of potassium sorbate
Add 25ml of 36% acetic acid to 100O,8) and adjust the pH to 2.
-3 and heated to 75°C. This aqueous liquid at the same temperature. Procedural amendment ■, Indication of the case, 1986 Patent Application No. 262480 2, Name of the invention, Process for purifying sorbic acid 3, Person making the amendment. Relationship with the case. Patent applicant address: Osaka. 9-6 Nozaki-cho, Ichikita-ku (zip code 530)
[Effect] In the present invention, by extraction using a specific solvent,
Sorbic acid can be efficiently isolated from an aqueous solution containing sorbic acid.
4、補正の対象
明細書の発明の詳細な説明の欄
特許出願人 日本合成化学工業株式会社*!:P t
h4. Detailed explanation of the invention in the specification to be amended Patent applicant Nippon Gosei Kagaku Kogyo Co., Ltd. *! :Pt
h
Claims (1)
ルビン酸含有水性液から、該ソルビン酸を脂肪族炭化水
素、芳香族炭化水素、ハロゲン含有炭化水素、ケトン類
及びエーテル類の少なくとも1種を用いて溶剤抽出する
ことを特徴とするソルビン酸の精製方法。From a sorbic acid-containing aqueous liquid obtained by oxidizing sorbaldehyde with a microorganism, the sorbic acid is extracted with a solvent using at least one of aliphatic hydrocarbons, aromatic hydrocarbons, halogen-containing hydrocarbons, ketones, and ethers. A method for purifying sorbic acid, characterized by:
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP26248088A JP2729285B2 (en) | 1988-10-18 | 1988-10-18 | Purification method of sorbic acid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP26248088A JP2729285B2 (en) | 1988-10-18 | 1988-10-18 | Purification method of sorbic acid |
Publications (2)
Publication Number | Publication Date |
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JPH02109987A true JPH02109987A (en) | 1990-04-23 |
JP2729285B2 JP2729285B2 (en) | 1998-03-18 |
Family
ID=17376372
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999025676A1 (en) * | 1997-11-14 | 1999-05-27 | Daicel Chemical Industries, Ltd. | Apparatus and method for recovering sorbic acid |
-
1988
- 1988-10-18 JP JP26248088A patent/JP2729285B2/en not_active Expired - Fee Related
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999025676A1 (en) * | 1997-11-14 | 1999-05-27 | Daicel Chemical Industries, Ltd. | Apparatus and method for recovering sorbic acid |
Also Published As
Publication number | Publication date |
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JP2729285B2 (en) | 1998-03-18 |
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