JPS648638B2 - - Google Patents
Info
- Publication number
- JPS648638B2 JPS648638B2 JP56047148A JP4714881A JPS648638B2 JP S648638 B2 JPS648638 B2 JP S648638B2 JP 56047148 A JP56047148 A JP 56047148A JP 4714881 A JP4714881 A JP 4714881A JP S648638 B2 JPS648638 B2 JP S648638B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- keto
- sorbose
- catalyst
- gulonic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000003054 catalyst Substances 0.000 claims description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 12
- VBUYCZFBVCCYFD-NUNKFHFFSA-N 2-dehydro-L-idonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)C(=O)C(O)=O VBUYCZFBVCCYFD-NUNKFHFFSA-N 0.000 claims description 9
- VBUYCZFBVCCYFD-UHFFFAOYSA-N D-arabino-2-Hexulosonic acid Natural products OCC(O)C(O)C(O)C(=O)C(O)=O VBUYCZFBVCCYFD-UHFFFAOYSA-N 0.000 claims description 9
- LKDRXBCSQODPBY-AMVSKUEXSA-N L-(-)-Sorbose Chemical compound OCC1(O)OC[C@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-AMVSKUEXSA-N 0.000 claims description 8
- 229910052797 bismuth Inorganic materials 0.000 claims description 7
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 6
- 230000001590 oxidative effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000000243 solution Substances 0.000 description 16
- 239000007864 aqueous solution Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-QTBDOELSSA-N L-gulonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-QTBDOELSSA-N 0.000 description 2
- GQXSDDHYUVYJCQ-NHRVJRKFSA-N [(3as,4as,8ar,8bs)-2,2,7,7-tetramethyl-4a,5,8a,8b-tetrahydro-[1,3]dioxolo[3,4]furo[1,3-d][1,3]dioxin-3a-yl]methanol Chemical compound O([C@H]12)C(C)(C)OC[C@@H]1O[C@]1(CO)[C@H]2OC(C)(C)O1 GQXSDDHYUVYJCQ-NHRVJRKFSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- -1 oxides Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- RLJMLMKIBZAXJO-UHFFFAOYSA-N lead nitrate Chemical compound [O-][N+](=O)O[Pb]O[N+]([O-])=O RLJMLMKIBZAXJO-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Saccharide Compounds (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【発明の詳細な説明】
本発明は、２―ケト―Ｌ―グロン酸をＬ―ソル
ボースの酸化により製造する方法に関するもので
ある。
従来、２―ケト―Ｌ―グロン酸をＬ―ソルボー
スの酸化で製造するには、２―ケト―Ｌ―グロン
酸とアセトンとを反応させ、ジアセトン―Ｌ―ソ
ルボースとし、これを次亜塩素酸塩または過マン
ガン酸塩を用いて酸化し、ジアセトン―２―ケト
―Ｌ―グロン酸を製造し、これを脱アセトンにす
る多段階の行程を経て製造していた。
この従来法は、多段反応操作を要し、行程が繁
雑であり、酸化剤として、高価な過マンガン酸塩
または次亜塩素酸塩等を消費する欠点があつた。
本発明の目的とするところは、従来法のような欠
点のない２―ケト―Ｌ―グロン酸の製造法を提供
するところにある。
本発明者は従来法のような欠点のないＬ―ソル
ボースの酸化方法に関して種々研究した結果、白
金またはパラジウムに第２成分として鉛またはビ
スマスを添加した触媒を用い、反応水溶液のPHを
適当に保ちながら空気酸化すれば、２―ケト―Ｌ
―グロン酸を、従来法と同様の収率で製造し得る
ことを見出し本発明を完成するに至つた。
すなわち、本発明の方法は、Ｌ―ソルボースを
水溶液中で白金または／およびパラジウムに鉛ま
たは／およびビスマスを含有する触媒の存在下に
反応液のPHを６〜10に保つて、含酸素ガスで酸化
した２―ケト―Ｌ―グロン酸を製造するものであ
る。
本発明の方法によれば、Ｌ―ソルボースをアセ
トンと反応させてジアセトン―Ｌ―ソルボースに
誘導してから酸化する必要がなく、従来法では三
段階を要した反応が一段で実施できる。また、次
亜塩素酸塩または過マンガン酸塩のような高価な
酸化剤を必要とせず、排酸化剤の後処理工程もな
しに、工業的に有利に２―ケト―Ｌ―グロン酸を
製造することが出来る。
本発明の方法で使用される触媒は、白金また
は／およびパラジウムに鉛または／およびビスマ
スを添加したものであつて、通常は適当な担体、
例えば、活性炭またはアルミナ等に担持して使用
する。白金およびパラジウムは金属状または酸化
物であつて、鉛およびビスマスは金属状、水酸化
物、酸化物、塩化物、炭酸塩、有機酸塩または硝
酸塩等である。担体への担持量は、パラジウムま
たは／および白金が0.1〜10wt％、好ましくは0.5
〜5wt％の範囲であり、鉛または／およびビスマ
スが0.5〜10wt％、好ましくは１〜5wt％の範囲
である。
触媒の調製方法は、常法、例えば、塩化白金酸
と硝酸鉛の水溶液を活性炭粉末に浸漬し、ホルマ
リン水溶液で還元処理する等による。また、市販
の貴金属を担持した炭素粉末触媒を、鉛または／
およびビスマスの可溶性塩の水溶液に浸漬、乾燥
する等の方法によつても調製できる。
本発明の方法は溶媒中で実施するが、溶媒とし
ては水を多用する。水溶液中に仕込む原料Ｌ―ソ
ルボースの濃度は、２〜20wt％、好ましくは５
〜15wt％の範囲である。
触媒の使用量は、例えば、反応をバツチで実施
する場合では、反応液１に対し５〜100ｇ、通
常は10〜50ｇの触媒を用いる。
反応の進行により、酸化により生じた目的物の
酸のために反応液のPHは７近傍から酸性側に移行
する。酸化反応の速度は、反応液のPHが酸性側で
は急激に低下するため、反応液のPHは中性近傍に
保つことが好ましい。この目的のために、反応の
進行に同期させて、アルカリ物質を逐時反応液中
に添加し、反応液のPHを６〜10に保つ。使用する
アルカリ物質は、苛性アルカリ、アルカリ金属の
炭酸塩または重炭酸塩等で、通常はこれらの水溶
液の形で、反応液に添加する。反応液のPHを逆に
PH10より塩基性にすると酸化反応の速度は増大す
るが、重合物やタール状の副生物が増加するので
好ましくない。したがつて、反応液のPHは６〜
10、更に好ましくは７〜９の範囲に保つて反応を
実施する。
本発明の方法で使用される酸化剤は含酸素ガス
であつて、酸素または空気が多用される。特に空
気を用いるのが好ましい。反応時の含酸素ガスの
圧力は常圧ないし５Kg／cm2が多用される。含酸素
ガスと反応液との混合状態は、ガスを反応液中に
吹込みよく撹拌する等して、気液の分散を良好に
保つことが必要である。
反応の温度は、室温〜100℃、特に40〜70℃の
範囲が好ましい。反応に要する時間は、バツチで
反応させる場合で示せば、１〜20時間、通常は２
〜10時間の範囲である。
反応器の形式は、通常、完全混合型の懸濁床で
撹拌槽式または気泡塔式の反応器が用いられる。
粒状の触媒による固定床式の反応器でもよい。反
応槽は一段でも、多段式でも同様に使用できる。
反応終了後、触媒を別した水溶液を減圧下に濃
縮し、これにメタノール等の低級アルコールまた
はアセトン等の溶媒を添加撹拌すると、目的物の
ナトリウム塩の結晶が析出するので、これを別
洗滌等の手段により単離することが出来る。
本発明の方法により得られる２―ケト―Ｌ―グ
ロン酸はアスコルビン酸（ビタミンＣ）の前駆体
として極めて有用な化合物である。
以下、実施例により本発明を説明する。
実施例 １
内径20cmのステンレス円筒容器にバツフル板、
タービン翼型の撹拌器、空気吹込管を付けたもの
を反応器に用いた。8wt％のＬ―ソルボース水溶
液１，2wt％pt，3wt％pbco3を活性炭粉末に担
持した触媒30ｇを仕込み、50℃に昇温した。常圧
で、空気を200ml／minで吹込み、500rpmで撹拌
しながら反応させた。反応の進行に伴ない、反応
液PHを７〜８に保つ様に水酸化ナトリウム水溶液
を逐時添加した。反応開始後2.5時間で水酸化ナ
トリウム水溶液の消費が停止したので反応を終了
し、反応液から触媒を分離した。反応液を高速液
体クロマトグラフイーで分析定量した結果、２―
ケト―Ｌ―グロン酸のナトリウム塩が87％の収率
で生成していた。
実施例 ２
実施例―１と同様の方法で、用いる触媒をかえ
て反応させた。得られた結果を表―１に示す。
【表】DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing 2-keto-L-gulonic acid by oxidation of L-sorbose. Conventionally, in order to produce 2-keto-L-gulonic acid by oxidizing L-sorbose, 2-keto-L-gulonic acid and acetone were reacted to form diacetone-L-sorbose, which was then mixed with hypochlorous acid. Diacetone-2-keto-L-gulonic acid was produced by oxidation using a salt or permanganate, and this was produced through a multi-step process of deacetonization. This conventional method requires multi-stage reaction operations, is complicated, and has the drawback of consuming expensive permanganate or hypochlorite as an oxidizing agent.
An object of the present invention is to provide a method for producing 2-keto-L-gulonic acid that does not have the drawbacks of conventional methods. As a result of various research into a method for oxidizing L-sorbose that does not have the drawbacks of conventional methods, the inventors of the present invention found that the pH of the reaction aqueous solution was maintained at an appropriate level by using a catalyst consisting of platinum or palladium with lead or bismuth added as a second component. If oxidized in air, 2-keto-L
-We have discovered that gulonic acid can be produced with the same yield as conventional methods, and have completed the present invention. That is, in the method of the present invention, L-sorbose is treated in an aqueous solution in the presence of a catalyst containing lead and/or bismuth in platinum or/and palladium, while maintaining the pH of the reaction solution at 6 to 10 and using an oxygen-containing gas. This method produces oxidized 2-keto-L-gulonic acid. According to the method of the present invention, it is not necessary to react L-sorbose with acetone to derive diacetone-L-sorbose and then oxidize it, and the reaction that required three steps in the conventional method can be carried out in one step. In addition, 2-keto-L-gulonic acid can be produced industrially advantageously without the need for expensive oxidizing agents such as hypochlorite or permanganate, and without any post-treatment process for waste oxidants. You can. The catalyst used in the process of the invention is platinum or/and palladium with lead or/and bismuth added, and is usually supported by a suitable carrier.
For example, it is used by being supported on activated carbon or alumina. Platinum and palladium are metallic or oxides, and lead and bismuth are metallic, hydroxides, oxides, chlorides, carbonates, organic acid salts or nitrates. The amount of palladium or/and platinum supported on the carrier is 0.1 to 10 wt%, preferably 0.5
~5 wt%, and lead or/and bismuth in the range of 0.5 to 10 wt%, preferably 1 to 5 wt%. The catalyst can be prepared by a conventional method, for example, immersing activated carbon powder in an aqueous solution of chloroplatinic acid and lead nitrate, followed by reduction treatment with an aqueous formalin solution. In addition, commercially available precious metal-supported carbon powder catalysts were mixed with lead or /
It can also be prepared by methods such as immersion in an aqueous solution of a soluble salt of bismuth and drying. The method of the present invention is carried out in a solvent, and water is frequently used as the solvent. The concentration of the raw material L-sorbose to be added to the aqueous solution is 2 to 20 wt%, preferably 5
~15wt% range. The amount of catalyst used is, for example, when the reaction is carried out in batches, 5 to 100 g, usually 10 to 50 g, of catalyst per reaction solution 1. As the reaction progresses, the pH of the reaction solution shifts from around 7 to the acidic side due to the acid of the target product produced by oxidation. Since the rate of oxidation reaction rapidly decreases when the pH of the reaction solution is acidic, it is preferable to maintain the pH of the reaction solution near neutrality. For this purpose, an alkaline substance is added to the reaction solution one after another in synchronization with the progress of the reaction, and the pH of the reaction solution is maintained at 6 to 10. The alkaline substance used is a caustic alkali, an alkali metal carbonate or bicarbonate, etc., and is usually added to the reaction solution in the form of an aqueous solution thereof. Reverse the PH of the reaction solution
If the pH is made more basic than 10, the rate of oxidation reaction will increase, but this is not preferable because it increases the amount of polymers and tar-like by-products. Therefore, the pH of the reaction solution is 6~
The reaction is carried out while maintaining the molecular weight within the range of 10, more preferably 7 to 9. The oxidizing agent used in the method of the present invention is an oxygen-containing gas, and oxygen or air is often used. In particular, it is preferable to use air. The pressure of the oxygen-containing gas during the reaction is often from normal pressure to 5 kg/cm 2 . Regarding the mixed state of the oxygen-containing gas and the reaction liquid, it is necessary to maintain good gas-liquid dispersion by, for example, blowing gas into the reaction liquid and stirring well. The reaction temperature is preferably in the range of room temperature to 100°C, particularly 40 to 70°C. The time required for the reaction is 1 to 20 hours when reacting in batches, usually 2 hours.
In the range of ~10 hours. The type of reactor is usually a completely mixed suspended bed, stirred tank type or bubble column type reactor.
A fixed bed reactor using a granular catalyst may also be used. The reaction tank can be used in a single stage or in a multistage type.
After the reaction is complete, the aqueous solution from which the catalyst has been removed is concentrated under reduced pressure, and when a lower alcohol such as methanol or a solvent such as acetone is added and stirred, crystals of the sodium salt of the target product precipitate, and these are washed separately, etc. It can be isolated by the following means. 2-keto-L-gulonic acid obtained by the method of the present invention is an extremely useful compound as a precursor of ascorbic acid (vitamin C). The present invention will be explained below with reference to Examples. Example 1 A stainless steel cylindrical container with an inner diameter of 20 cm and a full plate,
A turbine blade type stirrer and an air blowing tube were used in the reactor. 30 g of a catalyst consisting of an 8 wt % L-sorbose aqueous solution 1.2 wt % pt, 3 wt % PBCO 3 supported on activated carbon powder was charged, and the temperature was raised to 50°C. The reaction was carried out at normal pressure with air blown in at 200 ml/min and stirring at 500 rpm. As the reaction progressed, an aqueous sodium hydroxide solution was added at intervals to maintain the pH of the reaction solution at 7 to 8. The consumption of the aqueous sodium hydroxide solution stopped 2.5 hours after the start of the reaction, so the reaction was terminated and the catalyst was separated from the reaction solution. As a result of analyzing and quantifying the reaction solution using high performance liquid chromatography, 2-
The sodium salt of keto-L-gulonic acid was produced in 87% yield. Example 2 A reaction was carried out in the same manner as in Example-1, except that the catalyst used was changed. The results obtained are shown in Table-1. 【table】
Claims (1)
ン酸を製造するに際し、白金または／およびパラ
ジウムに鉛または／およびビスマスを含有する触
媒の存在下、含酸素ガスで酸化することを特徴と
する２―ケト―Ｌ―グロン酸の製造法。1. When oxidizing L-sorbose to produce 2-keto-L-gulonic acid, the process is characterized by oxidizing with an oxygen-containing gas in the presence of a catalyst containing lead or/and bismuth in platinum or/and palladium. Method for producing 2-keto-L-gulonic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56047148A JPS57163340A (en) | 1981-04-01 | 1981-04-01 | Preparation of 2-keto-l-gulonic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56047148A JPS57163340A (en) | 1981-04-01 | 1981-04-01 | Preparation of 2-keto-l-gulonic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57163340A JPS57163340A (en) | 1982-10-07 |
| JPS648638B2 true JPS648638B2 (en) | 1989-02-14 |
Family
ID=12767007
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56047148A Granted JPS57163340A (en) | 1981-04-01 | 1981-04-01 | Preparation of 2-keto-l-gulonic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57163340A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI75577C (en) * | 1984-01-23 | 1988-07-11 | Akzo Nv | Process for preparing 2-keto-aldonic acids. |
-
1981
- 1981-04-01 JP JP56047148A patent/JPS57163340A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57163340A (en) | 1982-10-07 |
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