JP2001512722A - Method for producing L-ascorbic acid - Google Patents
Method for producing L-ascorbic acidInfo
- Publication number
- JP2001512722A JP2001512722A JP2000506195A JP2000506195A JP2001512722A JP 2001512722 A JP2001512722 A JP 2001512722A JP 2000506195 A JP2000506195 A JP 2000506195A JP 2000506195 A JP2000506195 A JP 2000506195A JP 2001512722 A JP2001512722 A JP 2001512722A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- keto
- gulonic
- ascorbic acid
- producing
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/62—Three oxygen atoms, e.g. ascorbic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
(57)【要約】 ４０℃と８０℃の間の温度での２−ケト−Ｌ−グロン酸の濃鉱酸との反応により Ｌ−アスコルビン酸を製造する方法が開示される。 (57) [Summary] Disclosed is a method for producing L-ascorbic acid by reacting 2-keto-L-gulonic acid with a concentrated mineral acid at a temperature between 40C and 80C.
Description
【０００１】 本発明は、２−ケト−Ｌ−グロン酸を濃鉱酸と４０℃と８０℃の間の温度で反
応することによる Ｌ−アスコルビン酸の製造方法に関する。The present invention relates to a method for producing L-ascorbic acid by reacting 2-keto-L-gulonic acid with a concentrated mineral acid at a temperature between 40 ° C. and 80 ° C.
【０００２】 本発明は特に、反応を５０℃と７０℃の間の温度で実施することを特徴とする、
Ｌ−アスコルビン酸の製造方法に関する。The invention is particularly characterized in that the reaction is carried out at a temperature between 50 ° C. and 70 ° C.,
The present invention relates to a method for producing L-ascorbic acid.
【０００３】 ２−ケト−Ｌ−グロン酸の酸との反応による１段階でのアスコルビン酸の製造
方法は知られている。ＵＳ２，１８５，３８３は、２−ケト−Ｌ−グロン酸の濃
塩酸および溶媒としての酢酸との反応を記載している。未審査の日本出願５８−
１７７９８６は、エタノールおよびアセトン中の２−ケト−Ｌ−グロン酸ナトリ
ウム塩の溶液を先ず塩酸で中和するＬ−アスコルビン酸の製造方法を記載してい
る。審査された日本出願４８−１５９３１は、不活性溶媒中そして表面活性物質
の存在下に２−ケト−Ｌ−グロン酸の鉱酸との反応を記載している。同様、表面
活性物質の存在下の２−ケト−Ｌ−グロン酸無水物から出発するＬ−アスコルビ
ン酸の製造がWO87/00839に記載されている。EP 0 324 261およびGB 2,205,567は
、不活性溶媒の混合物中表面活性物質の存在下に２−ケト−Ｌ−グロン酸の酸と
の反応を記載している。[0003] Processes for the production of ascorbic acid in one step by reacting 2-keto-L-gulonic acid with an acid are known. US 2,185,383 describes the reaction of 2-keto-L-gulonic acid with concentrated hydrochloric acid and acetic acid as a solvent. Unexamined Japanese application 58-
177986 describes a process for producing L-ascorbic acid in which a solution of 2-keto-L-gulonic acid sodium salt in ethanol and acetone is first neutralized with hydrochloric acid. Examined Japanese Application 48-15931 describes the reaction of 2-keto-L-gulonic acid with a mineral acid in an inert solvent and in the presence of a surfactant. Similarly, the preparation of L-ascorbic acid starting from 2-keto-L-gulonic anhydride in the presence of a surfactant is described in WO 87/00839. EP 0 324 261 and GB 2,205,567 describe the reaction of 2-keto-L-gulonic acid with an acid in a mixture of inert solvents in the presence of a surfactant.
【０００４】 ２−ケト−Ｌ−グロン酸の３６％塩酸との反応がDE 2939052に記載されている。
ここでは、Ｌ−アスコルビン酸が１００℃での反応および塩酸を留去後８７％の
収率で得られる。The reaction of 2-keto-L-gulonic acid with 36% hydrochloric acid is described in DE 2939052.
Here, L-ascorbic acid is obtained in a yield of 87% after the reaction at 100 ° C. and the distillation of hydrochloric acid.
【０００５】 驚くべきことに、Ｌ−アスコルビン酸合成に関する研究が、もし反応を４０℃
と８０℃の間の温度で、特に５０℃と７０℃の間の温度で行うならば、高い収率
が得られることを示した。５７℃と６３℃の間の温度範囲が、反応を行うのに特
に好ましいことを証明した。[0005] Surprisingly, studies on L-ascorbic acid synthesis indicate that if the reaction
It has been shown that high yields are obtained when carried out at a temperature between and 80 ° C, especially between 50 and 70 ° C. A temperature range between 57 ° C. and 63 ° C. has proved to be particularly preferred for carrying out the reaction.
【０００６】 本発明による新規方法は、２−ケト−Ｌ−グロン酸の濃鉱酸によるラクトン化
によってＬ−アスコルビン酸を高収率で得ることを可能にする。特に、より低い
温度では、得られるアスコルビン酸の分解が、従来技術（例えばDE 293052；１ ００℃での方法）から知られる方法におけるよりも有意によりゆっくり起ること
が利点であることがわかった。さらなる利点はそれに伴うより低いエネルギー消
費であり、従ってより低い環境汚染であることを証明している。The novel process according to the invention makes it possible to obtain L-ascorbic acid in high yields by lactonization of 2-keto-L-gulonic acid with concentrated mineral acids. In particular, it has proven to be advantageous at lower temperatures that the decomposition of the ascorbic acid obtained takes place significantly more slowly than in processes known from the prior art (eg DE 293052; process at 100 ° C.). . A further advantage is the associated lower energy consumption, thus proving lower environmental pollution.
【０００７】 さらに、反応を有機溶媒なしで実施できることが従来技術に比較して有利であ
る。[0007] Furthermore, it is advantageous over the prior art that the reaction can be carried out without organic solvents.
【０００８】 本発明に記載の方法は、２−ケト−Ｌ−グロン酸および塩酸を１：３の定量比
で用いるならば、有利であることを証明している。本発明は従ってまた、２−ケ
ト−Ｌ−グロン酸および鉱酸を比率１：３で用いる方法に関する。The method according to the invention has proven advantageous if 2-keto-L-gulonic acid and hydrochloric acid are used in a quantitative ratio of 1: 3. The invention therefore also relates to a process using 2-keto-L-gulonic acid and mineral acid in a ratio of 1: 3.
【０００９】 しかし、濃度は広い範囲で変えることができる。より濃縮され、そしてまたよ
り希釈された処理が実施できる。２−ケト−Ｌ−グロン酸／濃塩酸の重量比は、
例えば１０：１と１：１０の間であってもよい。範囲は、特に好ましくは１：２
と１：４の間であり、そして１：３の比率が極めて有利である。[0009] However, the concentration can be varied over a wide range. More concentrated and also more dilute treatments can be performed. The weight ratio of 2-keto-L-gulonic acid / concentrated hydrochloric acid is:
For example, it may be between 10: 1 and 1:10. The range is particularly preferably 1: 2
And between 1: 4 and a ratio of 1: 3 is very advantageous.
【００１０】 鉱酸は、例えば塩酸、リン酸または硫酸を意味する。濃鉱酸が好ましく用いら
れる。[0010] Mineral acid means, for example, hydrochloric acid, phosphoric acid or sulfuric acid. Concentrated mineral acids are preferably used.
【００１１】 本発明はまた、記載されたように、使用される鉱酸が濃塩酸であることを特徴
とする、方法に関する。[0011] The invention also relates to a process, as described, characterized in that the mineral acid used is concentrated hydrochloric acid.
【００１２】 本発明はまた、記載されたように、２−ケト−Ｌ−グロン酸および濃鉱酸から
なる混合物を所望の温度に加熱することを特徴とする、方法に関する。[0012] The invention also relates to a method, as described, characterized in that a mixture of 2-keto-L-gulonic acid and a concentrated mineral acid is heated to a desired temperature.
【００１３】 反応時間は、通常１から５時間の間、特に２から４時間の間であり、そして約
３時間の反応時間が特に好ましい。The reaction time is usually between 1 and 5 hours, especially between 2 and 4 hours, and a reaction time of about 3 hours is particularly preferred.
【００１４】 処理は、例えば、活性炭処理、濾過、溶媒の除去そして結晶化のそれ自体知ら
れている方法によって実施される。本発明に記載の方法によれば、Ｌ−アスコル
ビン酸の収率は、概して９０％を超えるので、複雑な精製工程を省くことができ
る。上記および下記において、全ての温度は℃を表わす。The treatment is carried out, for example, by a method known per se of activated carbon treatment, filtration, removal of the solvent and crystallization. According to the method according to the invention, the yield of L-ascorbic acid is generally above 90%, so that complicated purification steps can be omitted. Above and below, all temperatures refer to ° C.
【００１５】実施例１ ２−ケト−Ｌ−グロン酸１００ｇを３７％塩酸３００ｇに入れる。このバッチ
を次いで５８℃に加熱し、そしてこの温度に３時間保つ。塩酸の除去と処理後、
理論量の９１．４％の収率のＬ−アスコルビン酸が得られる。 実施例２ ２−ケト−Ｌ−グロン酸１００ｇを３７％塩酸３００ｇに入れる。このバッチを
次いで５９−６０℃に加熱し、そしてこの温度に３時間保つ。塩酸の除去と処理
後、理論量の９０．２％の収率のＬ−アスコルビン酸が得られる。 実施例３ ２−ケト−Ｌ−グロン酸１００ｇを３７％塩酸３００ｇに入れる。このバッチ
を次いで５９−６０℃に加熱し、そしてこの温度に約１．５時間保つ。塩酸の除
去と処理後、理論量の８８．４％の収率のＬ−アスコルビン酸が得られる。 Example 1 100 g of 2-keto-L-gulonic acid are placed in 300 g of 37% hydrochloric acid. The batch is then heated to 58 ° C. and kept at this temperature for 3 hours. After removal and treatment of hydrochloric acid,
A yield of 91.4% of theory of L-ascorbic acid is obtained. Example 2 100 g of 2 -keto-L-gulonic acid are placed in 300 g of 37% hydrochloric acid. The batch is then heated to 59-60 ° C and kept at this temperature for 3 hours. After removal and treatment of hydrochloric acid, a yield of L-ascorbic acid of 90.2% of theory is obtained. Example 3 100 g of 2-keto-L-gulonic acid are placed in 300 g of 37% hydrochloric acid. The batch is then heated to 59-60 ° C and kept at this temperature for about 1.5 hours. After removal and treatment of hydrochloric acid, a yield of L-ascorbic acid of 88.4% of theory is obtained.
───────────────────────────────────────────────────── フロントページの続き (81)指定国 ＥＰ(ＡＴ，ＢＥ，ＣＨ，ＣＹ， ＤＥ，ＤＫ，ＥＳ，ＦＩ，ＦＲ，ＧＢ，ＧＲ，ＩＥ，Ｉ Ｔ，ＬＵ，ＭＣ，ＮＬ，ＰＴ，ＳＥ)，ＯＡ(ＢＦ，ＢＪ ，ＣＦ，ＣＧ，ＣＩ，ＣＭ，ＧＡ，ＧＮ，ＧＷ，ＭＬ， ＭＲ，ＮＥ，ＳＮ，ＴＤ，ＴＧ)，ＡＰ(ＧＨ，ＧＭ，Ｋ Ｅ，ＬＳ，ＭＷ，ＳＤ，ＳＺ，ＵＧ，ＺＷ)，ＥＡ(ＡＭ ，ＡＺ，ＢＹ，ＫＧ，ＫＺ，ＭＤ，ＲＵ，ＴＪ，ＴＭ) ，ＡＬ，ＡＭ，ＡＴ，ＡＵ，ＡＺ，ＢＡ，ＢＢ，ＢＧ， ＢＲ，ＢＹ，ＣＡ，ＣＨ，ＣＮ，ＣＵ，ＣＺ，ＤＥ，Ｄ Ｋ，ＥＥ，ＥＳ，ＦＩ，ＧＢ，ＧＥ，ＧＨ，ＨＵ，ＩＤ ，ＩＬ，ＩＳ，ＪＰ，ＫＥ，ＫＧ，ＫＰ，ＫＲ，ＫＺ， ＬＣ，ＬＫ，ＬＲ，ＬＳ，ＬＴ，ＬＵ，ＬＶ，ＭＤ，Ｍ Ｇ，ＭＫ，ＭＮ，ＭＷ，ＭＸ，ＮＯ，ＮＺ，ＰＬ，ＰＴ ，ＲＯ，ＲＵ，ＳＤ，ＳＥ，ＳＧ，ＳＩ，ＳＫ，ＳＬ， ＴＪ，ＴＭ，ＴＲ，ＴＴ，ＵＡ，ＵＧ，ＵＳ，ＵＺ，Ｖ Ｎ，ＹＵ，ＺＷ (71)出願人 Ｆｒａｎｋｆｕｒｔｅｒ Ｓｔｒ． 250, Ｄ−64293 Ｄａｒｍｓｔａｄｔ，Ｆｅｄ ｅｒａｌ Ｒｅｐｕｂｌｉｃ ｏｆ Ｇｅ ｒｍａｎｙ (72)発明者 ベシュマン， クラウス ドイツ連邦共和国 デー−64354、ライン ハイム、ヒンター デル ミュール 15 (72)発明者 ハインツ， ウォルフガング ドイツ連邦共和国 デー−62625 ベンス ハイム、ソードール−シュトルム−ヴェー ク 38 (72)発明者 クーン， ウォルター ドイツ連邦共和国 デー−63741 アシャ フェンブルク、ストーフェンベルクシュト ラーセ ８ Ｆターム(参考） 4C037 LA02 ──────────────────────────────────────────────────続 き Continuation of front page (81) Designated country EP (AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE ), OA (BF, BJ, CF, CG, CI, CM, GA, GN, GW, ML, MR, NE, SN, TD, TG), AP (GH, GM, KE, LS, MW, SD, SZ, UG, ZW), EA (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, CA, CH, CN, CU, CZ, DE, DK, EE, ES, FI, GB, GE, GH, HU, ID, IL, IS, JP, KE, KG, KP, KR, KZ , LC, LK, LR, LS, LT, LU, LV, MD, MG, MK, MN, MW, MX, NO, NZ, PL, PT, RO, RU, SD, SE, SG, SI, SK, SL, TJ, TM, TR, TT, UA, UG, US, UZ, VN, YU, ZW (71) Applicant Frankfurter Str. 250, D-64293 Darmstadt, Federal Republic of Germany (72) Inventor Beschmann, Klaus, Germany Day-64354, Rheinheim, Hinter del Muhl 15 (72) Inventor Heinz, Wolfgang, Germany Federal Republic of Germany -62625 Bens Heim, Sordor-Sturm-Week 38 (72) Inventor Kuhn, Walter Germany Day-63741 Asha Fenburg, Storfenbergstrasse 8 F-term (reference) 4C037 LA02
Claims (5)
度で反応させることを特徴とする、 Ｌ−アスコルビン酸の製造方法。1. A process for producing L-ascorbic acid, characterized in that 2-keto-L-gulonic acid is reacted with a concentrated mineral acid at a temperature between 40 ° C. and 80 ° C.
請求項１に記載の方法。2. The method according to claim 1, wherein the reaction is carried out at a temperature between 50 ° C. and 70 ° C.
The method of claim 1.
を特徴とする、請求項１又は２に記載の方法。3. The process according to claim 1, wherein the 2-keto-L-gulonic acid and the mineral acid are used in a ratio of 1: 3.
〜３のいずれかに記載の方法。4. The method according to claim 1, wherein the mineral acid used is concentrated hydrochloric acid.
The method according to any one of claims 1 to 3.
反応温度にすることを特徴とする、請求項１〜４のいずれかに記載の方法。5. The process according to claim 1, wherein a mixture of 2-keto-L-gulonic acid and a concentrated mineral acid is brought to a desired reaction temperature.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19734086.5 | 1997-08-07 | ||
| DE19734086A DE19734086C1 (en) | 1997-08-07 | 1997-08-07 | L-ascorbic acid preparation |
| PCT/EP1998/004649 WO1999007691A2 (en) | 1997-08-07 | 1998-07-24 | Process for preparing l-ascorbic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2001512722A true JP2001512722A (en) | 2001-08-28 |
Family
ID=7838185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000506195A Pending JP2001512722A (en) | 1997-08-07 | 1998-07-24 | Method for producing L-ascorbic acid |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP1001952A2 (en) |
| JP (1) | JP2001512722A (en) |
| KR (1) | KR20010022595A (en) |
| CN (1) | CN1265655A (en) |
| AR (1) | AR010938A1 (en) |
| AU (1) | AU9156298A (en) |
| BR (1) | BR9811855A (en) |
| CA (1) | CA2299364A1 (en) |
| CO (1) | CO4770883A1 (en) |
| DE (1) | DE19734086C1 (en) |
| ID (1) | ID25547A (en) |
| WO (1) | WO1999007691A2 (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19904821C1 (en) * | 1999-02-05 | 2000-07-06 | Merck Patent Gmbh | Preparation of L-ascorbic acid from 2-keto- or 2,3-4,6-diacetone-2-keto-L-gulonic acid |
| DE19919203A1 (en) | 1999-04-28 | 2000-11-02 | Basf Ag | Process for the preparation of L-ascorbic acid |
| DE19954511A1 (en) | 1999-11-12 | 2001-05-17 | Basf Ag | Process for the preparation of alkali salts of L-ascorbic acid |
| DE10022518A1 (en) * | 2000-05-10 | 2001-11-15 | Basf Ag | Preparation of L-ascorbic acids by reacting 2-keto-L-gulonic acids or melt of 2-keto-L-gulonic acid alkyl esters under acid catalysis using water-miscible solvent(s) |
| WO2002051827A1 (en) | 2000-12-22 | 2002-07-04 | Eastman Chemical Company | Process for producing ascorbic acid in the presence of a sulfit |
| EP1351949B1 (en) | 2000-12-22 | 2005-05-18 | Eastman Chemical Company | Continuous process for producing l-ascorbic acid |
| WO2002083739A2 (en) * | 2001-04-10 | 2002-10-24 | Danisco Usa, Inc. | Polymerization of mono and disaccharides with monocarboxylic acids and lactones |
| US6740762B2 (en) | 2001-08-24 | 2004-05-25 | Eastman Chemical Company | Process for ascorbic acids using alkaline earth silicate catalysts |
| US6716997B1 (en) | 2001-10-09 | 2004-04-06 | Eastman Chemical Company | Systems and methods for generation of ascorbic acid with reduced color |
| CN111018815A (en) * | 2019-12-29 | 2020-04-17 | 安徽丰原发酵技术工程研究有限公司 | Method for preparing vitamin C by increasing concentration of hydrochloric acid through solvent extraction |
| CN111087373A (en) * | 2019-12-29 | 2020-05-01 | 安徽丰原发酵技术工程研究有限公司 | Method for preparing vitamin C by acid method |
| CN114369075B (en) * | 2022-02-14 | 2023-09-29 | 河北乐开节能科技股份有限公司 | Method for preparing VC crystal by using aqueous solution of 2-keto-L-gulonic acid in one step |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2462251A (en) * | 1945-05-16 | 1949-02-22 | Merck & Co Inc | Process for preparing ascorbic acids |
| DD141832A1 (en) * | 1978-10-31 | 1980-05-21 | Joachim Schmidt | METHOD AND DEVICE FOR PREPARING L-ASCORBIN ACID |
| CN86105960A (en) * | 1985-08-09 | 1987-05-13 | 鲁布里佐尔公司 | Under substantially anhydrous conditions, prepare the L-xitix from 2-ketone-L-gulonic acid |
| DE3819045C2 (en) * | 1987-06-08 | 1997-06-19 | Takeda Chemical Industries Ltd | Production of L-ascorbic acid |
-
1997
- 1997-08-07 DE DE19734086A patent/DE19734086C1/en not_active Expired - Fee Related
-
1998
- 1998-07-24 WO PCT/EP1998/004649 patent/WO1999007691A2/en not_active Application Discontinuation
- 1998-07-24 BR BR9811855-2A patent/BR9811855A/en not_active Application Discontinuation
- 1998-07-24 KR KR1020007001187A patent/KR20010022595A/en not_active Application Discontinuation
- 1998-07-24 CA CA002299364A patent/CA2299364A1/en not_active Abandoned
- 1998-07-24 JP JP2000506195A patent/JP2001512722A/en active Pending
- 1998-07-24 CN CN98807955A patent/CN1265655A/en active Pending
- 1998-07-24 EP EP98943779A patent/EP1001952A2/en not_active Withdrawn
- 1998-07-24 AU AU91562/98A patent/AU9156298A/en not_active Abandoned
- 1998-07-24 ID IDW20000174A patent/ID25547A/en unknown
- 1998-08-06 CO CO98045322A patent/CO4770883A1/en unknown
- 1998-08-07 AR ARP980103913A patent/AR010938A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999007691A2 (en) | 1999-02-18 |
| BR9811855A (en) | 2000-08-15 |
| KR20010022595A (en) | 2001-03-26 |
| CO4770883A1 (en) | 1999-04-30 |
| AR010938A1 (en) | 2000-07-12 |
| AU9156298A (en) | 1999-03-01 |
| CA2299364A1 (en) | 1999-02-18 |
| ID25547A (en) | 2000-10-12 |
| DE19734086C1 (en) | 1998-08-13 |
| CN1265655A (en) | 2000-09-06 |
| EP1001952A2 (en) | 2000-05-24 |
| WO1999007691A3 (en) | 1999-04-08 |
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