JPH0387190A - Production of sorbic acid - Google Patents
Production of sorbic acidInfo
- Publication number
- JPH0387190A JPH0387190A JP22429689A JP22429689A JPH0387190A JP H0387190 A JPH0387190 A JP H0387190A JP 22429689 A JP22429689 A JP 22429689A JP 22429689 A JP22429689 A JP 22429689A JP H0387190 A JPH0387190 A JP H0387190A
- Authority
- JP
- Japan
- Prior art keywords
- sorbic acid
- gluconobacter
- sorbaldehyde
- microorganisms
- reaction
- 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
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 239000004334 sorbic acid Substances 0.000 title claims abstract description 17
- 235000010199 sorbic acid Nutrition 0.000 title claims abstract description 17
- 229940075582 sorbic acid Drugs 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 241000589236 Gluconobacter Species 0.000 claims abstract description 13
- 244000005700 microbiome Species 0.000 claims abstract description 13
- BATOPAZDIZEVQF-MQQKCMAXSA-N (E,E)-2,4-hexadienal Chemical compound C\C=C\C=C\C=O BATOPAZDIZEVQF-MQQKCMAXSA-N 0.000 claims abstract description 12
- BATOPAZDIZEVQF-UHFFFAOYSA-N sorbic aldehyde Natural products CC=CC=CC=O BATOPAZDIZEVQF-UHFFFAOYSA-N 0.000 claims abstract description 12
- 230000000813 microbial effect Effects 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 235000013372 meat Nutrition 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 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
- 229920002261 Corn starch Polymers 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 125000003180 beta-lactone group Chemical group 0.000 description 1
- 230000002599 biostatic effect Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 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
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001514 detection method Methods 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
- 235000019249 food preservative Nutrition 0.000 description 1
- 239000005452 food preservative Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 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 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- VGBPIHVLVSGJGR-UHFFFAOYSA-N thorium(4+);tetranitrate Chemical compound [Th+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VGBPIHVLVSGJGR-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
【発明の詳細な説明】
[産業上の利用分町]
本発明はソルブアルデヒドを微生物学的に酸化してソル
ビン酸を製造する方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Applications] The present invention relates to a method for producing sorbic acid by microbiologically oxidizing sorbaldehyde.
[従来の技術]
ソルビン酸或はその塩はいずれも抗カビカが優れている
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
、酸分解或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] Both sorbic acid and its salts have excellent antifungal properties and are used as food preservatives, but the industrial method for producing them is usually by reacting crotonaldehyde with ketene. A method has been practiced in which the polyester is produced via the intermediately formed β-lactone, and then the polyester is decomposed by heat, acid, or ion exchange resin 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或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 from a manufacturing or economical point of view.
[発明が解決しようとする課題]
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た
(特開昭63−152990号公報)がソルビン酸の収
率面で工業的規模での実施には未だ問題が残っていると
言える。[Problems to be Solved by the Invention] As a solution to this problem, a method has recently been proposed in which sorbic acid is produced by treating sorbaldehyde with specific microorganisms (Japanese Unexamined Patent Publication No. 152990/1983), but the method for producing sorbic acid has been proposed. It can be said that there are still problems with implementation on an industrial scale.
[課題を解決するための手段]
本発明者等は微生物学的処理により、ソルビン酸を製造
する方法について鋭意研究を重ねた結果、ソルブアルデ
ヒドをグルコノバクタ−属から選ばれる微生物の少なく
とも1種で処理する場合、収率良くソルビン酸が得られ
ることを見出し、本発明を完成するに至った。[Means for Solving the Problems] As a result of extensive research into a method for producing sorbic acid by microbiological treatment, the present inventors have developed a method for treating sorbaldehyde with at least one type of microorganism selected from the genus Gluconobacter. The inventors have discovered that sorbic acid can be obtained in good yield when doing so, and have completed the present invention.
ソルブアルデヒド(別称2.4−ヘキザジエナール)を
酸化するために用いられる微生物を具体的に例示すれば
、グルコノバクタ−ンオキシアセトニクス(Gluco
nobacLer dioxyacetonicsSI
F 0 3271 ) 、グルコノバクタ−グルコニ
クス(Gluconobacter gluconic
us。A specific example of a microorganism used to oxidize sorbaldehyde (also known as 2,4-hexadienal) is gluconobactan oxyacetonix (Gluco
nobacLer dioxyacetonicsSI
F 0 3271 ), Gluconobacter gluconic
us.
IFO3171)、グルコノバクタ−オキシダンス(G
luconobacter oxydance、 I
F 0 3189 ) 、タルコノバククー ルビギ
ノザス(Gluconobacter rubigin
。IFO3171), Gluconobacter oxidans (G
luconobacter oxydance, I
F 0 3189), Gluconobacter rubiginosas
.
sus、IF’0 3244)、グルコノバクタ−ザブ
オキノダンス(Gluconobacter 5ubo
xydans、 I F O3254)、グルコノバ
クタ−ザブオキンダンス(Gluconobactcr
5uboxydans、 I F 0 3256
)等がある。sus, IF'0 3244), Gluconobacter 5ubo
xydans, IFO3254), Gluconobacter xydans (IFO3254), Gluconobacter
5uboxydans, I F 0 3256
) etc.
」二足、微生物を培養するための培地としては炭素源、
窒素源等を含有し微生物が生育するものであればいずれ
でも良い。``Two feet, a carbon source as a medium for culturing microorganisms,
Any material may be used as long as it contains a nitrogen source and allows microorganisms to grow.
炭素源としては、微生物のもつソルビン酸生産活性を阻
害しない化合物であれば任意に使用でき、例えばグルコ
ース、ソニークロース、エタノール、エヂレングリコー
ル、プロピレングリコール、l、4−ブタンジオール、
グリセリン、アセトアルデヒド、酢酸、プロピオン酸な
どが挙げられる。又、窒素源として(ま肉エキス、ペプ
トン、コーンステイープリカー、尿素、硫酸アンモニウ
ム、塩化アンモニウム、硝酸すトリウムなどを用いるこ
とが出来る。更に、必要に応じてリン酸塩、マグネシウ
ム塩、カルシウム塩、鉄塩、銅塩、亜鉛塩などの無機塩
類や微生物の生育に必要な栄養物質を培地に適宜加える
ことができる。Any compound can be used as the carbon source as long as it does not inhibit the sorbic acid production activity of microorganisms, such as glucose, sonyclase, ethanol, ethylene glycol, propylene glycol, 1,4-butanediol,
Examples include glycerin, acetaldehyde, acetic acid, and propionic acid. In addition, as a nitrogen source (meat extract, peptone, cornstarch liquor, urea, ammonium sulfate, ammonium chloride, thorium nitrate, etc.) can be used.Furthermore, as necessary, phosphates, magnesium salts, calcium salts, Inorganic salts such as iron salts, copper salts, zinc salts, and nutritional substances necessary for the growth of microorganisms can be added to the medium as appropriate.
ソルブアルデヒドを処理するに当たっては、」二足の増
殖した微生物を含む培地をそのまま使用しても、又、且
該培地から集菌し、これを水或は生理食塩水、バッファ
ーに懸濁したものを使用しても良い。When treating sorbaldehyde, you can use a medium containing two-legged microorganisms as is, or you can collect bacteria from the medium and suspend them in water, physiological saline, or a buffer. You may also use
反応液に対してソルブアルデヒドは系中濃度が0.01
〜lO%好ましくは0.05〜5%程度の範囲で添加さ
れる。仕込み方式は一括、分割、連続等任意に変更可能
であるが、実用上は逐次仕込方式が有利である。The concentration of sorbaldehyde in the reaction solution is 0.01.
It is added in a range of about 10% to 10%, preferably about 0.05 to 5%. The preparation method can be arbitrarily changed such as batch, divided, continuous, etc., but the sequential preparation method is practically advantageous.
菌体は懸WAoxc当たり0.5〜20仔(乾燥菌)程
度用いられる。Approximately 0.5 to 20 bacterial cells (dried bacteria) are used per WAoxc.
反応時には撹拌を行い好気的条件を採用する。かかる条
件に設定するjこは系内に空気や酸素或は必要に応じて
他のガスを混合した混合ガスを吹き込むが、溶液中の酸
素濃度を1 ppm以上とするのが望ましい。During the reaction, stir and use aerobic conditions. To set such conditions, air, oxygen, or a mixed gas containing other gases as necessary is blown into the system, and it is desirable that the oxygen concentration in the solution be 1 ppm or more.
反応温度は10〜70℃、好ましくは20〜40℃、P
Hは3〜10、好ましくは4〜9、反応時間は01〜2
00時間程度時間開が有利である。The reaction temperature is 10-70°C, preferably 20-40°C, P
H is 3-10, preferably 4-9, reaction time is 01-2
An opening time of about 00 hours is advantageous.
又、反応液へ必要に応じてPQQやNAD (P)等の
補酵素、界面活性剤、有機溶媒等を適宜添加することも
可能である。Furthermore, it is also possible to appropriately add coenzymes such as PQQ and NAD (P), surfactants, organic solvents, etc. to the reaction solution as necessary.
更に、反応は増殖期の微生物を用い、培養液に直接添加
して反応する方法や体止菌体による反応を単独もしくは
組合せたり、他の固定化菌体、菌体抽出処理物を用いる
反応を単独もしくは上記方法と組合せて行う等種々の態
様が可能である。Furthermore, the reaction can be carried out using microorganisms in the growth phase, by directly adding them to the culture solution, by using biostatic cells alone or in combination, or by using other immobilized microorganisms or microbial extracts. Various embodiments are possible, such as carrying out the method alone or in combination with the above methods.
反応終了後、ソルビン酸を餡゛法に従って、精製して目
的物を得る。After the reaction is completed, sorbic acid is purified according to the bean method to obtain the desired product.
[作 用]
本発明においては特定の微生物を用いてソルブアルデヒ
ドを酸化することによって、収率良く高純度のソルビン
酸を製造することが出来る。[Function] In the present invention, high purity sorbic acid can be produced in good yield by oxidizing sorbaldehyde using a specific microorganism.
[実施例コ
次に実例を挙げて本発明の方法を更に具体的に説明する
。[Example] Next, the method of the present invention will be explained in more detail with reference to examples.
実施例1
普通栄養培地(肉エキス3g、ペプトン10g、食塩5
2、水IQ、PH7)50mlを坂ロフラスコに入れ、
滅菌処理後、グルコノバクタ−ジオキシアセトニクス(
IFO3271)を1白金耳接種して37℃、48時間
往往復上う培養した。培養後遠心分離法にて集菌し、菌
体をPH7,0,0、1,Mリン酸バッファーにて2回
洗浄し、dry換算で75畔の菌体を得た。Example 1 Ordinary nutrient medium (3 g of meat extract, 10 g of peptone, 5 g of salt)
2. Put 50ml of water (IQ, PH7) into a Sakaro flask.
After sterilization, Gluconobacter dioxyacetonix (
One platinum loop of IFO3271) was inoculated and cultured in a round trip at 37°C for 48 hours. After culturing, the cells were collected by centrifugation, and the cells were washed twice with PH7, 0, 0, 1, M phosphate buffer to obtain 75 cells in dry terms.
次に大型試験管にdry換算で20mgの菌体を入れ、
PH7,0,0,1’Mリン酸バッファーを5ml加え
て菌体を懸濁した後にソルブアルデヒド5mgを添加し
て反応を開始した。反応は30℃にて20分間行い、1
分間に200回往復振トウして反応液を撹拌した。Next, put 20 mg of bacterial cells in dry terms into a large test tube.
After adding 5 ml of PH7, 0, 0, 1'M phosphate buffer to suspend the bacterial cells, 5 mg of sorbaldehyde was added to start the reaction. The reaction was carried out at 30°C for 20 minutes.
The reaction solution was stirred by back-and-forth shaking 200 times per minute.
反応終了後、遠心分離法によって反応液の上澄み液を分
取し、これを塩酸でPH2としたのち、ガスクロマド分
析法にてソルビン酸の収率を測定した。After the reaction was completed, the supernatant of the reaction solution was separated by centrifugation, and after adjusting the pH of the supernatant to 2 with hydrochloric acid, the yield of sorbic acid was measured by gas chromad analysis.
ソルビン酸生成率は67%であった。The sorbic acid production rate was 67%.
尚、ガスクロマド分析の条件は次の通りである。Note that the conditions for gas chromad analysis are as follows.
装 置;ヒユーレット パラカード 589o型カ
ラム;メチルシリコン系ワイドボアカラム0.53mm
X 15m
カラム湯度;
80℃、
8分〜昇温(1
5°C/分)〜
■
0℃、
4分
検
出
ID
、実施例2〜6、
比較例1
実施例1の菌株の代わりに下表に示す菌株を用いた以外
は実施例1と同様に反応を行った。Equipment: Huuret Paracard 589o type
Ram: Methyl silicone wide bore column 0.53mm
X 15m Column water temperature; 80°C, 8 minutes ~ temperature increase (15°C/min) ~ ■ 0°C, 4 minutes Detection ID, Examples 2 to 6, Comparative Example 1 In place of the strain of Example 1, The reaction was carried out in the same manner as in Example 1 except that the strains shown in the table were used.
結果を表に示す。The results are shown in the table.
Claims (1)
生物の少なくとも1種で処理することを特徴とするソル
ビン酸の製造方法。A method for producing sorbic acid, which comprises treating sorbaldehyde with at least one microorganism selected from the genus Gluconobacter.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP22429689A JPH0387190A (en) | 1989-08-29 | 1989-08-29 | Production of sorbic acid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP22429689A JPH0387190A (en) | 1989-08-29 | 1989-08-29 | Production of sorbic acid |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0387190A true JPH0387190A (en) | 1991-04-11 |
Family
ID=16811550
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP22429689A Pending JPH0387190A (en) | 1989-08-29 | 1989-08-29 | Production of sorbic acid |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0387190A (en) |
-
1989
- 1989-08-29 JP JP22429689A patent/JPH0387190A/en active Pending
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