JPH0772184B2 - Method for producing d-l-α-tocopherol - Google Patents
Method for producing d-l-α-tocopherolInfo
- Publication number
- JPH0772184B2 JPH0772184B2 JP61070553A JP7055386A JPH0772184B2 JP H0772184 B2 JPH0772184 B2 JP H0772184B2 JP 61070553 A JP61070553 A JP 61070553A JP 7055386 A JP7055386 A JP 7055386A JP H0772184 B2 JPH0772184 B2 JP H0772184B2
- Authority
- JP
- Japan
- Prior art keywords
- tocopherol
- metallic zinc
- trimethylhydroquinone
- producing
- acetate
- 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 - Lifetime
Links
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
- Pyrane Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、医薬品、食品、動物薬、飼料などに有用なdl
−α−トコフェロールの新規な製造方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial field of application] The present invention is useful for drugs, foods, veterinary drugs, feeds, etc.
-A novel method for producing α-tocopherol.
dl−α−トコフェロールは、代表的なビタミンＥであ
り、医薬品、食品、動物薬、飼料などとして広く汎用さ
れており、需要が年々増大している。dl-α-tocopherol is a typical vitamin E, which is widely used as a medicine, food, veterinary medicine, feed and the like, and its demand is increasing year by year.
このdl−α−トコフェロールを製造する方法としては、
従来より数多く知られている。As a method for producing this dl-α-tocopherol,
Many have been known from the past.
これらの方法のほとんどは、2,3,5−トリメチルハイド
ロキノンと、フィトール、イソフィトールなどのフィト
ール類を種々の触媒を用いて、縮合反応するものである
（例えば特開昭47-29366、特開昭49-47372、特開昭48-4
8472、特公昭45-21835など）。Most of these methods involve condensation reaction of 2,3,5-trimethylhydroquinone and phytols such as phytol and isophytol using various catalysts (see, for example, JP-A-47-29366, JP-A-47-29366). Sho-49-47372, JP-A-48-4
8472, etc.
しかしながら、この2,3,5−トリメチルハイドロキノン
を出発物質とする方法は、工業的には次のような欠点を
有している。However, this method using 2,3,5-trimethylhydroquinone as a starting material has the following drawbacks industrially.
即ち、2,3,5−トリメチルハイドロキノンは飛散しや
すい粉末で、皮膚に付着すると炎症を起こし易い、帯
電し易く、静電気による爆発を誘発し易いため、取り扱
い上特別の対策が必要とされる、空気中にて酸化を受
けやすく、その結果、この酸化物はdl−α−トコフェロ
ールの純度に悪影響を及ぼす、及び2,3,5−トリメチ
ルハイドロキノンを結晶として取り出すためには濾過、
乾燥などの操作が必要であり、工業的には不利である、
という種々の欠点を有する。That is, 2,3,5-trimethylhydroquinone is a powder that easily scatters, is liable to cause irritation when it adheres to the skin, is easily charged, and easily causes an explosion due to static electricity, and thus requires special handling measures. It is susceptible to oxidation in air, as a result of which this oxide adversely affects the purity of dl-α-tocopherol, and filtration to remove 2,3,5-trimethylhydroquinone as crystals,
Operation such as drying is necessary, which is industrially disadvantageous.
It has various drawbacks.
そこで、これらの欠点を解決するために、2,3,5−トリ
メチルハイドロキノンを出発物質とせず、2,3,5−トリ
メチル−1,4−ベンゾキノンを出発物質とする方法も提
案されている（特開昭50-15736、特開昭50-157368、特
開昭50-157369）。Therefore, in order to solve these drawbacks, a method has been proposed in which 2,3,5-trimethylhydroquinone is not used as a starting material and 2,3,5-trimethyl-1,4-benzoquinone is used as a starting material. JP-A-50-15736, JP-A-50-157368, and JP-A-50-157369).
これらの方法は、2,3,5−トリメチル−1,4−ベンゾキノ
ンを出発物質とし、還元触媒の存在下、接触水素添加還
元法により、2,3,5−トリメチルハイドロキノンを得る
方法であるが、これらの方法は数kg/cm2の水素ガスを使
用するため、安全性の確保に特別の対応策が必要とさ
れ、工業的には問題が多い。即ち、工業化のためには、
耐圧装置、安全装置などが必要であり、経済的な見地か
ら極めて不利である。These methods are methods of obtaining 2,3,5-trimethylhydroquinone by catalytic hydrogenation reduction in the presence of a reducing catalyst using 2,3,5-trimethyl-1,4-benzoquinone as a starting material. Since these methods use several kg / cm 2 of hydrogen gas, special countermeasures are required to ensure safety, and there are many industrial problems. That is, for industrialization,
A pressure device and a safety device are required, which is extremely disadvantageous from an economical point of view.
そこで本発明者等は、2,3,5−トリメチル−1,4−ベンゾ
キノンを出発原料としてdl−α−トコフェロールを製造
する従来の方法の欠点を改良し、高純度、高収率のdl−
α−トコフェロールを製造する方法について長年検討を
重ねてきたが、次の方法が所期の目的を満足することが
できることを見出し、本発明を完成するに到った。Therefore, the present inventors have improved the drawbacks of the conventional method for producing dl-α-tocopherol using 2,3,5-trimethyl-1,4-benzoquinone as a starting material, and have high purity and high yield of dl-
After many years of studies on a method for producing α-tocopherol, the inventors have found that the following method can satisfy the intended purpose, and have completed the present invention.
本発明の方法は、dl−α−トコフェロールを製造するに
際し、2,3,5−トリメチル−1,4−ベンゾキノンを出発物
質とし、これを金属亜鉛及び硫酸；金属亜鉛、塩酸及び
酢酸；金属亜鉛及び塩酸ガス；あるいはハイドロサルフ
ァイトから選ばれる還元剤を用いて還元して、2,3,5−
トリメチルハイドロキノンとし、次いで得られた2,3,5
−トリメチルハイドロキノン体を反応液から取りだすこ
となく、該液にフィトール類を加え、触媒として金属亜
鉛及び塩化亜鉛を用いて40℃以下で縮合反応せしめるこ
とを特徴とするdl−α−トコフェロールの製造方法であ
る。According to the method of the present invention, when dl-α-tocopherol is produced, 2,3,5-trimethyl-1,4-benzoquinone is used as a starting material, and metallic zinc and sulfuric acid; metallic zinc, hydrochloric acid and acetic acid; metallic zinc And hydrochloric acid gas; or by reducing with a reducing agent selected from hydrosulfite to give 2,3,5-
Trimethylhydroquinone, then obtained 2,3,5
A method for producing dl-α-tocopherol, characterized in that phytols are added to the liquid without removing the trimethylhydroquinone form from the reaction liquid, and a condensation reaction is performed at 40 ° C. or lower using metallic zinc and zinc chloride as a catalyst. Is.
即ち、本発明の方法は、2,3,5−トリメチル−1,4−ベン
ゾキノンを出発物質として、還元、縮合反応の連続操作
を経て、dl−α−トコフェロールを製造する方法に関す
るものである。That is, the method of the present invention relates to a method for producing dl-α-tocopherol through continuous operation of reduction and condensation reaction using 2,3,5-trimethyl-1,4-benzoquinone as a starting material.
本発明方法の特徴は、出発物質として2,3,5−トリメチ
ル−1,4−ベンゾキノンを用い、中間体としての2,3,5−
トリメチルハイドロキノンを粉体として取り出すことな
く、反応機構的に考えると次の工程とするフィトール類
との縮合反応を連続的に行うことである。The method of the present invention is characterized in that 2,3,5-trimethyl-1,4-benzoquinone is used as a starting material and 2,3,5-
Considering the reaction mechanism, the condensation reaction with phytols, which is the next step, is carried out continuously without taking out trimethylhydroquinone as powder.
この際、還元剤としては、具体的には例えば金属亜鉛及
び硫酸；金属亜鉛、塩酸及び酢酸；金属亜鉛及び塩酸ガ
ス；ハイドロサルファイトなどが好ましいが、最も好ま
しい例を挙げれば金属亜鉛・35％硫酸水溶液法を挙げる
ことができる。At this time, as the reducing agent, for example, metallic zinc and sulfuric acid; metallic zinc, hydrochloric acid and acetic acid; metallic zinc and hydrochloric acid gas; hydrosulfite and the like are preferable, but the most preferable example is metallic zinc. A sulfuric acid aqueous solution method can be mentioned.
金属亜鉛の形態は、粉末、顆粒、薄片などがあるが、粉
末が最も好ましい結果を与える。The forms of metallic zinc include powders, granules, flakes, etc., but powders give the most favorable results.
還元反応を行う際は、通常溶媒中に還元剤を加え還元反
応を行うが、溶媒としては酢酸エステル類、例えば酢酸
メチル、酢酸エチル、酢酸プロピル、酢酸イソプロピル
等が挙げられるが、これらのうち酢酸エチルが最も好ま
しい。When carrying out the reduction reaction, a reducing agent is usually added to the solvent to carry out the reduction reaction, and examples of the solvent include acetic acid esters such as methyl acetate, ethyl acetate, propyl acetate and isopropyl acetate. Most preferred is ethyl.
また還元反応終了後、通常金属亜鉛を常法により除去
し、次いで水洗後、酢酸エチルをスラリー状になるまで
留去する方法が最も好ましい結果を与える。Further, a method in which metallic zinc is usually removed by a conventional method after the reduction reaction is completed, followed by washing with water and then distilling off ethyl acetate until it becomes a slurry gives the most preferable result.
フィトール類としては、フィトール、イソフィトールな
どを挙げることができる。Examples of phytols include phytol and isophytol.
また、本発明においては、触媒として金属亜鉛及び塩化
亜鉛と共に、無水酢酸を加えて反応させることにより、
dl−α−トコフェロールアセテートを得ることができ
る。この場合、dl−α−トコフェロールを反応中で取り
出さなくてもよい。Further, in the present invention, by adding acetic anhydride and reacting with metallic zinc and zinc chloride as a catalyst,
dl-α-tocopherol acetate can be obtained. In this case, dl-α-tocopherol need not be removed during the reaction.
本発明方法によれば、出発物質として2,3,5−トリメチ
ルハイドロキノン体を使用しないため、前述した欠点が
なく、更に2,3,5−トリメチル−1,4−ベンゾキノンを用
いて接触水素添加反応を行う従来の方法と比較して、金
属亜鉛、硫酸などを使用できるため、工業化が容易であ
る。更に原料も安価であるため、工業的生産上、大きな
メリットがある。According to the method of the present invention, since the 2,3,5-trimethylhydroquinone body is not used as a starting material, the above-mentioned disadvantages are not present, and catalytic hydrogenation is further performed using 2,3,5-trimethyl-1,4-benzoquinone. Compared with the conventional method of carrying out the reaction, metal zinc, sulfuric acid, etc. can be used, so that industrialization is easy. Further, since the raw material is inexpensive, there is a great merit in industrial production.
結局、本発明方法によれば、高純度のdl−α−トコフェ
ロールを高収率に製造することが可能であり、工業的価
値は極めて高いものである。After all, according to the method of the present invention, high-purity dl-α-tocopherol can be produced in a high yield, and its industrial value is extremely high.
以下に、本発明の具体的な実施例を挙げるが、本発明が
これらのみに限定されることがないことはいうまでもな
い。Specific examples of the present invention will be given below, but it goes without saying that the present invention is not limited thereto.
尚、実施例において、TMBQとは、2,3,5−トリメチル−
1,4−ベンゾキノンを意味する。In the examples, TMBQ is 2,3,5-trimethyl-
It means 1,4-benzoquinone.
実施例１ TMBQ60.0gに酢酸エチル250ml、35％硫酸155.0gを加え、
攪拌下、金属亜鉛30.0gを添加した。添加終了後水層を
分離し、有機層を水洗、濃縮してスラリー状にした。Example 1 250 ml of ethyl acetate and 155.0 g of 35% sulfuric acid were added to 60.0 g of TMBQ,
With stirring, 30.0 g of metallic zinc was added. After the addition was completed, the aqueous layer was separated, and the organic layer was washed with water and concentrated to form a slurry.
このスラリー液に塩化亜鉛57.5g、金属亜鉛0.5g、酢酸
5.0g、濃塩酸6.0gを加え、40℃でイソフィトール100.0g
を３時間で滴下した。滴下終了後、更に1.5時間反応を
続けた。57.5 g of zinc chloride, 0.5 g of metallic zinc, acetic acid
Add 5.0 g and concentrated hydrochloric acid 6.0 g, and add 100.0 g of isophytol at 40 ℃.
Was added dropwise over 3 hours. After the dropping was completed, the reaction was continued for another 1.5 hours.
縮合反応終了後、水洗、アルカリ水洗し、常法に従いア
セチル化し、淡黄色油状の粗dl−α−トコフェロールア
セテート153.2gを得た。After completion of the condensation reaction, the product was washed with water, washed with alkaline water and acetylated according to a conventional method to obtain 153.2 g of crude dl-α-tocopherol acetate as a pale yellow oil.
この粗dl−α−トコフェロールアセテートを分子蒸留に
より精製し、純度99.5％のdl−α−トコフェロールアセ
テートを得た。This crude dl-α-tocopherol acetate was purified by molecular distillation to obtain 99.5% pure dl-α-tocopherol acetate.
実施例２ TMBQ60.0gに酢酸エチル250ml、酢酸50.0g、濃塩酸5.0g
を加え、攪拌下金属亜鉛30.0gを添加した。Example 2 TMBQ 60.0 g, ethyl acetate 250 ml, acetic acid 50.0 g, concentrated hydrochloric acid 5.0 g
And 30.0 g of metallic zinc were added with stirring.
以下、実施例１と同様にして粗dl−α−トコフェロール
アセテート152.8gを得た。Then, in the same manner as in Example 1, 152.8 g of crude dl-α-tocopherol acetate was obtained.
この粗dl−α−トコフェロールアセテートを分子蒸留に
より精製し、純度99.0％のdl−α−トコフェロールアセ
テートを得た。This crude dl-α-tocopherol acetate was purified by molecular distillation to obtain 99.0% pure dl-α-tocopherol acetate.
実施例３ TMBQ60.0gに酢酸エチル500ml、20％ハイドロサルファイ
ト水溶液520.0gを加え、攪拌下室温で２時間反応した。Example 3 To 60.0 g of TMBQ were added 500 ml of ethyl acetate and 520.0 g of 20% aqueous hydrosulfite solution, and the mixture was reacted at room temperature for 2 hours with stirring.
還元反応終了後、水層を分離し、有機層を濃縮してスラ
リー状にした。その後、実施例１の方法と同様に、縮合
反応、アセチル化反応を行い、粗dl−α−トコフェロー
ルアセテート145.0gを得た。After the reduction reaction was completed, the aqueous layer was separated, and the organic layer was concentrated to form a slurry. Then, the condensation reaction and the acetylation reaction were performed in the same manner as in Example 1 to obtain 145.0 g of crude dl-α-tocopherol acetate.
この粗dl−α−トコフェロールアセテートを分子蒸留に
より精製し、純度99.0％のdl−α−トコフェロールアセ
テートを得た。This crude dl-α-tocopherol acetate was purified by molecular distillation to obtain 99.0% pure dl-α-tocopherol acetate.
実施例４ TMBQ60.0gに酢酸エチル240ml、金属亜鉛36.0gを加え、
攪拌下塩酸ガスを通じた。Example 4 To 60.0 g of TMBQ, 240 ml of ethyl acetate and 36.0 g of metallic zinc were added,
Under stirring, hydrochloric acid gas was passed.
更にこれに酢酸4.8mlを加え、塩酸ガスを通じ40℃でイ
ソフィトール100.0gを３時間で滴下した。滴下終了後更
に１時間反応を続けた。Further, 4.8 ml of acetic acid was added thereto, and 100.0 g of isophytol was added dropwise at 40 ° C. over 3 hours through a hydrochloric acid gas. After the dropping was completed, the reaction was continued for another hour.
縮合反応終了後、実施例１の方法と同様に処理して、粗
dl−α−トコフェロールアセテート145.1gを得た。After completion of the condensation reaction, the same treatment as in Example 1 was conducted to obtain a crude
145.1 g of dl-α-tocopherol acetate was obtained.
この粗dl−α−トコフェロールアセテートを分子蒸留に
より精製し、純度99.0％のdl−α−トコフェロールアセ
テートを得た。This crude dl-α-tocopherol acetate was purified by molecular distillation to obtain 99.0% pure dl-α-tocopherol acetate.
実施例５ TMBQ60.0gに酢酸エチル240ml、金属亜鉛36.0gを加え、
攪拌下塩酸ガスを通じた。更に酢酸4.8ml、濃塩酸4.8m
l、塩化亜鉛54.5gを加え40℃でイソフィトール100.0gを
３時間で滴下した。Example 5 240 ml of ethyl acetate and 36.0 g of metallic zinc were added to 60.0 g of TMBQ,
Under stirring, hydrochloric acid gas was passed. Acetic acid 4.8 ml, concentrated hydrochloric acid 4.8 m
l, 54.5 g of zinc chloride were added, and 100.0 g of isophytol was added dropwise at 40 ° C. over 3 hours.
以下、実施例１と同様にして、粗dl−α−トコフェロー
ルアセテート148.3gを得た。Thereafter, in the same manner as in Example 1, 148.3 g of crude dl-α-tocopherol acetate was obtained.
この粗dl−α−トコフェロールアセテートを分子蒸留に
より精製して純度99.2％のdl−α−トコフェロールアセ
テートを得た。The crude dl-α-tocopherol acetate was purified by molecular distillation to obtain 99.2% pure dl-α-tocopherol acetate.
実施例６ TMBQ60.0gに酢酸イソプロピル250ml、35％硫酸155.0gを
加え、攪拌下、金属亜鉛30.0gを添加した。Example 6 250 ml of isopropyl acetate and 155.0 g of 35% sulfuric acid were added to 60.0 g of TMBQ, and 30.0 g of metallic zinc was added with stirring.
以下、実施例１と同様にして、粗dl−α−トコフェロー
ルアセテート152.0gを得た。Thereafter, in the same manner as in Example 1, 152.0 g of crude dl-α-tocopherol acetate was obtained.
この粗dl−α−トコフェロールアセテートを分子蒸留に
より精製し純度99.0％のdl−α−トコフェロールアセテ
ートを得た。The crude dl-α-tocopherol acetate was purified by molecular distillation to obtain 99.0% pure dl-α-tocopherol acetate.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 森田 栄一 愛知県葉栗郡木曽川町黒田下市場南128− １ 田中マンシヨン605 (72)発明者 高橋 通 岐阜県岐阜市五坪町25−87 コーポ田神Ｃ −507 (56)参考文献 特開 昭56−169686（ＪＰ，Ａ) 特開 昭50−157367（ＪＰ，Ａ) ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Eiichi Morita 128-1 Kuroda Shita Market, Kisogawa-cho, Haguri-gun, Aichi Prefecture Tanaka Mansion 605 (72) Inventor Toru Takahashi 25-87 Gotsubo-cho, Gifu City, Gifu Prefecture Corp. -507 (56) Reference JP-A-56-169686 (JP, A) JP-A-50-157367 (JP, A)
Claims (1)
し、2,3,5−トリメチル−1,4−ベンゾキノンを出発物質
とし、これを金属亜鉛及び硫酸；金属亜鉛、塩酸及び酢
酸；金属亜鉛及び塩酸ガス；あるいはハイドロサルファ
イトから選ばれる還元剤を用いて還元して、2,3,5−ト
リメチルハイドロキノンとし、次いで得られた2,3,5−
トリメチルハイドロキノン体を反応液から取りだすこと
なく、該液にフィトール類を加え、触媒として金属亜鉛
及び塩化亜鉛を用いて40℃以下で縮合反応せしめること
を特徴とするdl−α−トコフェロールの製造方法。1. When producing dl-.alpha.-tocopherol, starting material is 2,3,5-trimethyl-1,4-benzoquinone, which is used as metallic zinc and sulfuric acid; metallic zinc, hydrochloric acid and acetic acid; metallic zinc and Hydrochloric acid gas; or reduction with a reducing agent selected from hydrosulfite to give 2,3,5-trimethylhydroquinone, and then the obtained 2,3,5-
A method for producing dl-α-tocopherol, which comprises adding phytols to the liquid without taking out the trimethylhydroquinone compound from the reaction liquid and conducting condensation reaction at 40 ° C. or lower using metallic zinc and zinc chloride as catalysts.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61070553A JPH0772184B2 (en) | 1986-03-28 | 1986-03-28 | Method for producing d-l-α-tocopherol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61070553A JPH0772184B2 (en) | 1986-03-28 | 1986-03-28 | Method for producing d-l-α-tocopherol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62226976A JPS62226976A (en) | 1987-10-05 |
| JPH0772184B2 true JPH0772184B2 (en) | 1995-08-02 |
Family
ID=13434829
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61070553A Expired - Lifetime JPH0772184B2 (en) | 1986-03-28 | 1986-03-28 | Method for producing d-l-α-tocopherol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0772184B2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5600029A (en) * | 1994-03-09 | 1997-02-04 | Takeda Chemical Industries, Ltd. | Process for producing DL-tocopherols and intermediates therefor |
| FR2784104B1 (en) * | 1998-09-18 | 2002-12-27 | Rhone Poulenc Nutrition Animal | PROCESS FOR THE PREPARATION OF VITAMIN E |
| CN100564372C (en) | 2004-08-19 | 2009-12-02 | 帝斯曼知识产权资产管理有限公司 | The method that is used for the high boiling mixture to air and/or temperature sensitive useful products of rectifying |
| JP2013063912A (en) * | 2011-08-31 | 2013-04-11 | Eisai R & D Management Co Ltd | PRODUCTION METHOD OF α-TOCOPHEROL AND ACETIC ACID α-TOCOPHEROL |
| CN103450473B (en) * | 2013-09-09 | 2015-12-23 | 湖北吉和昌化工科技有限公司 | N, N '-bis-(dimethylaminoalkyl) urea-α, the preparation method of ω-saturated dihalide base co-polymer |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6021988B2 (en) * | 1974-06-10 | 1985-05-30 | 株式会社クラレ | Method of producing chroman derivatives |
| JPS56169686A (en) * | 1980-06-02 | 1981-12-26 | Shiseido Co Ltd | Preparation of vitamine e homolog and its analoqous compound |
-
1986
- 1986-03-28 JP JP61070553A patent/JPH0772184B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62226976A (en) | 1987-10-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0772184B2 (en) | Method for producing d-l-α-tocopherol | |
| US5312978A (en) | Process for producing vitamin A acid | |
| JPH03215455A (en) | Production of aromatic bisanilines | |
| EP0484122B1 (en) | Method for obtaining high-purity cinnamic acid | |
| KR100641825B1 (en) | Preparation method of 4-biphenylacetic acid | |
| US2999875A (en) | Preparation of amino acids | |
| JP3291987B2 (en) | Purification method of O, S-dimethyl-N-acetylphosphoramidothioate | |
| CN114560894B (en) | Preparation method of anti-new crown medicine Molnupiravir | |
| CN113248465B (en) | Synthetic method of biochanin A | |
| RU2817042C1 (en) | Method for synthesis of intermediate compound for producing sodium-glucose linked transporter (sglt) inhibitor | |
| JPS6064977A (en) | Praparation of alpha-tocopherol | |
| JPS6072881A (en) | Production of alpha-tocopherol | |
| JPS62255456A (en) | Production of diethylformamide | |
| JP2811525B2 (en) | Method for synthesizing 2-butyl-4-chloro-5-formylimidazole | |
| JP2907523B2 (en) | Method for producing cinnamic acids | |
| CN116410056A (en) | Preparation and separation method of 9-anthracene formic acid and 9-anthracene methanol | |
| JPS5944316B2 (en) | Industrial synthesis method of 2,6-dihydroxycineol from high-purity sobrerol via pinol | |
| US20230322699A1 (en) | Synthesis method for preparing sglt inhibitor intermediate | |
| CN117623999A (en) | Production process of 2,2'- (propane-2, 2' -diylbis (sulfadiyl)) diethylamine and hydrochloride thereof | |
| JPS6236018B2 (en) | ||
| JPH10101659A (en) | Production of substituted thiazolidine-dione derivative | |
| CN117945977A (en) | Synthesis process of indole-3-lactic acid | |
| JPS62294637A (en) | Purification of crude iburpofen | |
| JPS6330906B2 (en) | ||
| JPH0142935B2 (en) |