JP2006241091A - Method for producing 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid - Google Patents
Method for producing 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid Download PDFInfo
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本発明は、２，３−ビス（ベンジルアミノ）コハク酸をホスゲンと反応させることにより、１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸を製造する方法に関するものである〔下記反応式（１）参照〕。このジカルボン酸は、ビオチン中間体等として有用である。 The present invention relates to a process for producing 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid by reacting 2,3-bis (benzylamino) succinic acid with phosgene. See the following reaction formula (1)]. This dicarboxylic acid is useful as a biotin intermediate or the like.
１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸を製造する方法の１つとして、２，３−ビス（ベンジルアミノ）コハク酸を塩基性水溶液中でホスゲンと反応させる方法が知られている。この反応により得られる１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸の塩基性水溶液からの該ジカルボン酸の取り出しは、該水溶液を酸と混合して酸性条件下に該ジカルボン酸を析出させる（以下、このように酸性条件下で析出させることを酸析ということがある）ことにより行うことができるが、その際、析出物がペースト状になり易いため、反応器に付着して取り出し難くなるという問題が生じることがある。 As one method for producing 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid, there is a method in which 2,3-bis (benzylamino) succinic acid is reacted with phosgene in a basic aqueous solution. Are known. Removal of the dicarboxylic acid from the basic aqueous solution of 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid obtained by this reaction is carried out by mixing the aqueous solution with an acid and subjecting the dicarboxylic acid to acidic conditions. It can be performed by precipitating acid (hereinafter, precipitation under acidic conditions in this way is sometimes referred to as acid precipitation). This may cause a problem that it becomes difficult to take out.
このような問題を解決するため、例えば、特開昭５５−１０２５７０号公報（特許文献１）には、塩素化炭化水素の共存下に酸析を行うことが提案されており、その際、ｐＨは１以下とすることが開示されている。また、特開２００４−４３３０６号公報（特許文献２）には、酸析後、６５℃以上の温度で析出物と母液を接触させることが提案されており、その際、ｐＨは通常７以下、好ましくは２以下とし、また通常０以上とすることが開示されている。さらに、特開２００４−４３４１２号公報（特許文献３）には、６５℃以上の温度で酸析を行うことが提案されており、その際、ｐＨは上記同様、通常７以下、好ましくは２以下とし、また通常０以上とすることが開示されている。 In order to solve such a problem, for example, Japanese Patent Application Laid-Open No. 55-102570 (Patent Document 1) proposes to perform acid precipitation in the presence of chlorinated hydrocarbons. Is disclosed to be 1 or less. JP 2004-43306 A (Patent Document 2) proposes that after acid precipitation, the precipitate is brought into contact with the mother liquor at a temperature of 65 ° C. or higher, and the pH is usually 7 or less. It is disclosed that it is preferably 2 or less, and usually 0 or more. Furthermore, Japanese Patent Application Laid-Open No. 2004-43412 (Patent Document 3) proposes performing acid precipitation at a temperature of 65 ° C. or higher, and the pH is usually 7 or less, preferably 2 or less, as described above. In addition, it is disclosed that it is usually 0 or more.
本発明の目的は、酸析の際、特許文献１の如く塩素化炭化水素を共存させなくとも、また特許文献２ないし３の如く６５℃以上の高温操作を行わなくとも、析出物のペースト化を抑制して、操作性良く１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸を製造しうる方法を提供することにある。 The object of the present invention is to make a precipitate into a paste without acid coexisting without the presence of chlorinated hydrocarbons as in Patent Document 1 and without operating at a high temperature of 65 ° C. or higher as in Patent Documents 2 to 3. Is to provide a method capable of producing 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid with good operability.
本発明者らは鋭意研究を行った結果、上記１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸の水溶液を、所定のｐＨになるように酸と混合して、酸析を行うことにより、上記目的を達成できることを見出し、本発明を完成するに至った。 As a result of intensive studies, the inventors of the present invention mixed an aqueous solution of the above 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid with an acid so as to have a predetermined pH, and performed acid precipitation. As a result, the present inventors have found that the above object can be achieved and have completed the present invention.
すなわち、本発明は、２，３−ビス（ベンジルアミノ）コハク酸を塩基性水溶液中でホスゲンと反応させ、得られた１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸の塩基性水溶液をｐＨが３〜４．５となるように鉱酸と混合して、該ジカルボン酸を析出させることを特徴とする、１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸の製造方法を提供するものである。 That is, the present invention reacts 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid obtained by reacting 2,3-bis (benzylamino) succinic acid with phosgene in a basic aqueous solution. 1,3-dibenzyl-2-oxoimidazolidine-4,5- characterized in that a basic aqueous solution is mixed with a mineral acid so as to have a pH of 3 to 4.5 to precipitate the dicarboxylic acid. A method for producing a dicarboxylic acid is provided.
本発明によれば、２，３−ビス（ベンジルアミノ）コハク酸とホスゲンから、操作性良く１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸を製造することができる。 According to the present invention, 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid can be produced from 2,3-bis (benzylamino) succinic acid and phosgene with good operability.
本発明で原料に用いる２，３−ビス（ベンジルアミノ）コハク酸は、例えば、米国特許第２４８９２３２号明細書や、ジャーナル・オブ・ザ・アメリカン・ケミカル・ソサイエティ（Journal of the American Chemical Society）、（米国）、１９７８年、第１００巻、ｐ．１５５８−１５６３に記載される如く、２，３−ジブロモコハク酸をベンジルアミンと反応させることにより、調製することができる〔下記反応式（２）参照〕。 Examples of 2,3-bis (benzylamino) succinic acid used as a raw material in the present invention include, for example, US Pat. No. 2,489,232, Journal of the American Chemical Society, (USA), 1978, vol. 100, p. As described in 1558-1563, it can be prepared by reacting 2,3-dibromosuccinic acid with benzylamine [see the following reaction formula (2)].
具体的には、上記両文献に記載の如く、２，３−ジブロモコハク酸をエタノール溶媒中でベンジルアミンと反応させた後、酸及び水を加えて酸性条件下に２，３−ビス（ベンジルアミノ）コハク酸を析出させ、次いで濾過等により取り出せばよい。 Specifically, as described in both of the above documents, 2,3-dibromosuccinic acid is reacted with benzylamine in an ethanol solvent, and then acid and water are added to form 2,3-bis (benzyl) under acidic conditions. Amino) succinic acid may be precipitated and then removed by filtration or the like.
また、水と分液可能な有機溶媒中で、２，３−ジブロモコハク酸をベンジルアミンと反応させた後、塩基性水溶液により２，３−ビス（ベンジルアミノ）コハク酸を抽出するという処方を採用することもできる。この処方によれば、晶析操作が省略できると共に、得られる２，３−ビス（ベンジルアミノ）コハク酸の塩基性水溶液を、原料溶液としてそのままホスゲンとの反応に付すことができて、有利である。ここで、水と分液可能な有機溶媒としては、２−ブタノン、３−メチル−２−ブタノン、４−メチル−２−ペンタノンの如き炭素数４〜８程度の脂肪族ケトンが好ましく用いられ、塩基性水溶液としては、無機塩基の水溶液、中でも水酸化ナトリウムや水酸化カリウムの如き金属水酸化物の水溶液が好ましく用いられる。なお、この処方により調製される２，３−ビス（ベンジルアミノ）コハク酸の塩基性水溶液には、未反応のベンジルアミンが含まれることがあり、かかる水溶液をホスゲンとの反応に付すと、続く酸析の際に析出物がペースト状になり易い傾向にあるが、本発明によれば、かかる水溶液を原料に用いた場合でも、析出物のペースト化を抑制して、操作性良く１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸を製造することができる。 In addition, the formulation of extracting 2,3-bis (benzylamino) succinic acid with a basic aqueous solution after reacting 2,3-dibromosuccinic acid with benzylamine in an organic solvent that can be separated from water. It can also be adopted. According to this formulation, the crystallization operation can be omitted, and the resulting basic aqueous solution of 2,3-bis (benzylamino) succinic acid can be directly subjected to a reaction with phosgene as a raw material solution. is there. Here, as an organic solvent that can be separated from water, an aliphatic ketone having about 4 to 8 carbon atoms such as 2-butanone, 3-methyl-2-butanone, and 4-methyl-2-pentanone is preferably used. As the basic aqueous solution, an aqueous solution of an inorganic base, particularly an aqueous solution of a metal hydroxide such as sodium hydroxide or potassium hydroxide is preferably used. Incidentally, the basic aqueous solution of 2,3-bis (benzylamino) succinic acid prepared by this formulation may contain unreacted benzylamine, which continues when the aqueous solution is subjected to reaction with phosgene. Although the precipitate tends to become a paste during acid precipitation, according to the present invention, even when such an aqueous solution is used as a raw material, the precipitation of the precipitate is suppressed, and the operability is good. -Dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid can be prepared.
上記の如く調製される２，３−ビス（ベンジルアミノ）コハク酸を、塩基性水溶液中でホスゲンと反応させることにより、１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸の塩基性水溶液を得る。 2,3-bis (benzylamino) succinic acid prepared as described above is reacted with phosgene in a basic aqueous solution to give 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid. A basic aqueous solution is obtained.
ホスゲンとしては、液体のものを使用してもよいし、気体のものを使用してもよい。また、塩基性水溶液としては、無機塩基の水溶液、特に水酸化ナトリウムや水酸化カリウムの如き金属水酸化物の水溶液が好ましく用いられる。 As phosgene, a liquid thing or a gaseous thing may be used. As the basic aqueous solution, an aqueous solution of an inorganic base, particularly an aqueous solution of a metal hydroxide such as sodium hydroxide or potassium hydroxide is preferably used.
反応は、２，３−ビス（ベンジルアミノ）コハク酸の塩基性水溶液に、ホスゲンを導入すると共に、上記の如き塩基を導入しながら、該水溶液のｐＨが９〜１４、好ましくは１０〜１２に保たれるように行うのがよい。反応温度は通常０〜５０℃程度である。なお、この反応は、例えば特許文献２や３に記載の如く、水と分液可能な有機溶媒の共存下に油水二相系で行ってもよい。また、上記塩基性水溶液中には、必要により水溶性有機溶媒が溶解していてもよいが、その量は通常、該水溶液中に存在する水に対し０．１重量倍までである。 In the reaction, while introducing phosgene into a basic aqueous solution of 2,3-bis (benzylamino) succinic acid and introducing the base as described above, the pH of the aqueous solution is adjusted to 9 to 14, preferably 10 to 12. It is better to keep it. The reaction temperature is usually about 0 to 50 ° C. This reaction may be carried out in an oil-water two-phase system in the presence of water and an organic solvent that can be separated as described in Patent Documents 2 and 3, for example. In the basic aqueous solution, a water-soluble organic solvent may be dissolved if necessary, but the amount is usually up to 0.1 times by weight with respect to the water present in the aqueous solution.
こうして反応混合物として得られる１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸の塩基性水溶液を、次いで鉱酸と混合して、酸性条件下に１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸を析出させるが、本発明では、この酸との混合後のｐＨの終点を３〜４．５とする。このようにｐＨの終点をあまり低くしないことで、析出物のペースト化を抑制することができ、操作性良く１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸を製造することができる。 The basic aqueous solution of 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid thus obtained as a reaction mixture is then mixed with mineral acid and subjected to 1,3-dibenzyl-2-acid under acidic conditions. Oxoimidazolidine-4,5-dicarboxylic acid is precipitated. In the present invention, the end point of the pH after mixing with this acid is 3 to 4.5. Thus, by making the end point of pH not too low, it is possible to suppress the pasting of precipitates, and to produce 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid with good operability. Can do.
鉱酸としては、例えば、塩化水素、硫酸、硝酸、臭化水素、燐酸等が挙げられ、通常、その水溶液として使用される。１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸の塩基性水溶液と鉱酸との混合は、該塩基性水溶液の中に鉱酸を加えることにより行うのが望ましい。また、混合温度は通常０〜５０℃程度である。 Examples of the mineral acid include hydrogen chloride, sulfuric acid, nitric acid, hydrogen bromide, phosphoric acid and the like, and are usually used as an aqueous solution thereof. The mixing of the basic aqueous solution of 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid with the mineral acid is preferably carried out by adding the mineral acid to the basic aqueous solution. The mixing temperature is usually about 0 to 50 ° C.
析出した１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸は、通常、濾過やデカンテーション等により分離され、必要によりさらに水洗や乾燥等の操作に付される。回収量が少なめの場合は、母液を濃縮して析出させるのも有効である。 The precipitated 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid is usually separated by filtration, decantation or the like, and further subjected to operations such as washing with water and drying as necessary. If the recovered amount is small, it is also effective to concentrate the mother liquor to precipitate it.
以下、本発明の実施例を示すが、本発明はこれによって限定されるものではない。例中、濃度を表す％は特記ないかぎり重量基準である。 Examples of the present invention will be described below, but the present invention is not limited thereto. In the examples,% representing concentration is based on weight unless otherwise specified.
参考例１
（２，３−ビス（ベンジルアミノ）コハク酸の調製）
２Ｌフラスコに、２，３−ジブロモコハク酸１９６ｇと４−メチル−２−ペンタノン４００ｇを入れて攪拌した。この中に、ベンジルアミン５１９ｇを４０℃にて１時間かけて滴下した後、８０℃で２時間、次いで１００℃で２時間、保持した。得られた反応混合物に４９％水酸化カリウム水溶液３６０ｇと水１５５ｇを加え混合後、油層と水層とに分離した。水層を４−メチル−２−ペンタノン２００ｇで２回洗浄し、２，３−ビス（ベンジルアミノ）コハク酸を１７．５％、及びベンジルアミンを３．８％含むｐＨ１４の水溶液９６１ｇを得た。
Reference example 1
(Preparation of 2,3-bis (benzylamino) succinic acid)
In a 2 L flask, 196 g of 2,3-dibromosuccinic acid and 400 g of 4-methyl-2-pentanone were added and stirred. Into this, 519 g of benzylamine was dropped at 40 ° C. over 1 hour, and then kept at 80 ° C. for 2 hours and then at 100 ° C. for 2 hours. To the resultant reaction mixture, 360 g of a 49% aqueous potassium hydroxide solution and 155 g of water were added and mixed, and then separated into an oil layer and an aqueous layer. The aqueous layer was washed twice with 200 g of 4-methyl-2-pentanone to obtain 961 g of pH 14 aqueous solution containing 17.5% 2,3-bis (benzylamino) succinic acid and 3.8% benzylamine. .
実施例１
（ａ）ホスゲンとの反応
参考例１で得られた２，３−ビス（ベンジルアミノ）コハク酸を含む水溶液８０５ｇ〔２，３−ビス（ベンジルアミノ）コハク酸１４１ｇ（０．４２９モル）含有〕とトルエン４０７ｇを、２Ｌフラスコに入れて３２℃に保持した。この中にホスゲン１４２ｇを６時間かけて吹き込んだ後、３２℃で０．５時間、保持した。また、この吹き込みと保持の間、反応液のｐＨが１０．８に保たれるように、４９％水酸化カリウム水溶液６１５ｇを加えた。得られた混合物をろ過して固体を除去した後、濾液を油層と水層とに分離して、水層として、１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸を１０．６％含むｐＨ１２の水溶液１２６３ｇ〔１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸１３４ｇ（０．３７８モル、収率８８％）含有〕を得た。
Example 1
(A) Reaction with phosgene 805 g of aqueous solution containing 2,3-bis (benzylamino) succinic acid obtained in Reference Example 1 [containing 141 g (0.429 mol) of 2,3-bis (benzylamino) succinic acid] And 407 g of toluene were placed in a 2 L flask and maintained at 32 ° C. After 142 g of phosgene was blown into this over 6 hours, it was kept at 32 ° C. for 0.5 hours. Further, 615 g of a 49% aqueous potassium hydroxide solution was added so that the pH of the reaction solution was maintained at 10.8 during the blowing and holding. The resulting mixture was filtered to remove the solid, and the filtrate was then separated into an oil layer and an aqueous layer, and 10- (1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid was added as the aqueous layer. As a result, 1263 g of a pH 12 aqueous solution containing 1.6% (containing 134 g of 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid (0.378 mol, yield 88%)) was obtained.
（ｂ）酸析
得られた１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸を含む水溶液１８０ｇ〔１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸１９．１ｇ（０．０５３８モル）含有〕を、５００ｍＬフラスコに入れて撹拌し、この中に２５℃で２０％塩酸６７ｇを滴下して、混合物のｐＨを３．５とした。その結果、１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸が、フラスコの壁面や撹拌器に付着することなく、析出した。この析出物を濾取し、常温で減圧乾燥して、純度７０％の１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸２３ｇ〔純分１６．１ｇ（０．０４５４モル、回収率８４％）〕を得た。
(B) Acid precipitation 180 g of an aqueous solution containing 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid obtained [1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid 19 0.1 g (0.0538 mol)] was placed in a 500 mL flask and stirred, and 67 g of 20% hydrochloric acid was added dropwise thereto at 25 ° C. to adjust the pH of the mixture to 3.5. As a result, 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid precipitated without adhering to the wall of the flask or the stirrer. The precipitate was collected by filtration, dried under reduced pressure at room temperature, and 23 g of 70% pure 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid [pure 16.1 g (0.0454 mol, Recovery 84%)].
比較例１
実施例１（ａ）で得られた１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸を含む水溶液１０５ｇ〔１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸１１．１ｇ（０．０３１４モル）含有〕を、５００ｍＬフラスコに入れて攪拌し、この中に２５℃で２０％塩酸６５ｇを滴下して、混合物のｐＨを１．７とした。その結果、１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸が、ペースト状になって、フラスコの壁面や撹拌器に付着して、析出した。この析出物をかき取って濾取し、常温で減圧乾燥して、純度７６％の１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸１３ｇ〔純分９．９ｇ（０．０２７９モル、回収率８９％）〕を得た。
Comparative Example 1
105 g of an aqueous solution containing 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid obtained in Example 1 (a) [1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid 11.1 g (0.0314 mol) of acid] was placed in a 500 mL flask and stirred, and 65 g of 20% hydrochloric acid was added dropwise at 25 ° C. to adjust the pH of the mixture to 1.7. As a result, 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid became a paste and deposited on the wall surface of the flask and the stirrer. The precipitate was scraped off, collected by filtration, and dried under reduced pressure at room temperature to obtain 13 g of 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid having a purity of 76% [pure content of 9.9 g (0. 0279 mol, recovery rate 89%).
比較例２
実施例１（ａ）で得られた１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸を含む水溶液５００ｇ〔１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸５３ｇ（０．１５０モル）含有〕を、１Ｌフラスコに入れて攪拌し、この中に２５℃で２０％塩酸３０９ｇを滴下して、混合物のｐＨを１．７とした。その結果、１，３−ジベンジル−２−オキソイミダゾリジン−４，５−ジカルボン酸が、ペースト状になって、フラスコの壁面や撹拌器に付着して、析出した。次いで、混合物を６５℃に加熱して、１時間保持したが、析出物はフラスコの壁面や撹拌器に付着したままであった。
Comparative Example 2
500 g of an aqueous solution containing 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid obtained in Example 1 (a) [1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid 53 g (0.150 mol) of acid] was placed in a 1 L flask and stirred, and 309 g of 20% hydrochloric acid was added dropwise at 25 ° C. to adjust the pH of the mixture to 1.7. As a result, 1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid became a paste and deposited on the wall surface of the flask and the stirrer. The mixture was then heated to 65 ° C. and held for 1 hour, but the precipitate remained attached to the flask walls and stirrer.
Claims (2)
2,3-Dibromosuccinic acid is reacted with benzylamine in an organic solvent that can be separated from water and then mixed with a basic aqueous solution. The basicity of the resulting 2,3-bis (benzylamino) succinic acid The production method according to claim 1, wherein an aqueous solution is subjected to a reaction with the phosgene.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105399677A (en) * | 2015-11-17 | 2016-03-16 | 蚌埠丰原医药科技发展有限公司 | Preparation method of trans-naphthenic acid |
| CN109734669A (en) * | 2019-02-19 | 2019-05-10 | 安徽泰格维生素实业有限公司 | A kind of refining methd of double benzyl dicarboxylic acids |
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2005
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105399677A (en) * | 2015-11-17 | 2016-03-16 | 蚌埠丰原医药科技发展有限公司 | Preparation method of trans-naphthenic acid |
| CN109734669A (en) * | 2019-02-19 | 2019-05-10 | 安徽泰格维生素实业有限公司 | A kind of refining methd of double benzyl dicarboxylic acids |
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