JPH0231706B2 - TORANSUUHEKISAHIDOROTEREFUTARUSANNOSEIHO - Google Patents
TORANSUUHEKISAHIDOROTEREFUTARUSANNOSEIHOInfo
- Publication number
- JPH0231706B2 JPH0231706B2 JP3243682A JP3243682A JPH0231706B2 JP H0231706 B2 JPH0231706 B2 JP H0231706B2 JP 3243682 A JP3243682 A JP 3243682A JP 3243682 A JP3243682 A JP 3243682A JP H0231706 B2 JPH0231706 B2 JP H0231706B2
- Authority
- JP
- Japan
- Prior art keywords
- trans
- htp
- cis
- water
- metal salt
- 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
- 150000003839 salts Chemical class 0.000 claims description 22
- 229910052751 metal Inorganic materials 0.000 claims description 20
- 239000002184 metal Substances 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 9
- 239000003021 water soluble solvent Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- PXGZQGDTEZPERC-IZLXSQMJSA-N OC(=O)[C@H]1CC[C@H](C(O)=O)CC1 Chemical compound OC(=O)[C@H]1CC[C@H](C(O)=O)CC1 PXGZQGDTEZPERC-IZLXSQMJSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000001914 filtration Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- -1 etc.) Chemical compound 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- GYDJEQRTZSCIOI-UHFFFAOYSA-N Tranexamic acid Chemical compound NCC1CCC(C(O)=O)CC1 GYDJEQRTZSCIOI-UHFFFAOYSA-N 0.000 description 2
- AXDPKROMVHUKCD-TXQFBUHCSA-L [Na+].[Na+].[O-]C(=O)[C@H]1CC[C@H](C([O-])=O)CC1 Chemical compound [Na+].[Na+].[O-]C(=O)[C@H]1CC[C@H](C([O-])=O)CC1 AXDPKROMVHUKCD-TXQFBUHCSA-L 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明はトランス−ヘキサヒドロテレフタル酸
の製法に関する。本明細書において、ヘキサヒド
ロテレフタル酸をHTPと略し、そのトランス体
及びシス体をそれぞれトランス−HTP、シス−
HTPと表わし、また金属塩とはアルカリ金属又
はアルカリ土類金属の塩を意味し、具体的にはナ
トリウム、カリウム、カルシウム及びバリウム等
が含まれる。
トランス−HTPは抗プラスミン剤として知ら
れるトランス−４−アミノメチルシクロヘキサン
カルボン酸に導くことのできる有用な物質であ
る。
従来、シス、トランス混合HTPからトランス
−HTPを製造する方法としては次のような方法
が知られている。
(1) シス、トランス混合HTPからクロロホルム
でシス−HTPを抽出除去し、抽出残査をトラ
ンス−HTPとして得る方法〔Ber.、67、1785、
（1934）〕
(2) シス、トランス混合HTPから水でシス−
HTPを溶解除去し、残査をトランス−HTPと
して得る方法〔Rec.Trav.Chim.、80、588、
（1961）〕
しかし、これらの方法はいずれも工業的見地か
ら次のような欠点を有している。即ち、(1)の方法
ではクロロホルムに対する両異性体間の溶解度差
が小さいので混合HTPから一方を分離しにくく、
得られるトランス−HTPの純度が低い。(2)の方
法ではシス−HTPの水に対する溶解度が小さく、
シス−HTPを溶解除去するには多量の水を要す
る。又結晶からシス−HTPを溶解除去するため、
除去が不完全で得られるトランス−HTPの純度
が低い。このようにトランス−HTPを有利に得
ることができないため、従来トランス−４−アミ
ノメチルシクロヘキサンカルボン酸を製する際に
は、HTPとしてシス、トランス混合液のまま次
の反応を行ない、後の段階で生成物で異性体を分
離してトランス体を取得するような方法がとられ
ていた。
本発明者らは、従来法のかかる欠点を克服すべ
く鋭意研究を重ねた結果、HTPを金属塩にする
と水、水溶性溶媒及びそれらの混合液に対してシ
ス体とトランス体の溶解度差が大きくなり、溶解
度の小さいトランス体の分離取得が可能であるこ
とを見い出した。即ち、代表的な例としてHTP
ナトリウム塩のシス体とトランス体の水、メタノ
ール及びエタノールに対する最大溶解量を示せば
次表の通りである。
The present invention relates to a process for producing trans-hexahydroterephthalic acid. In this specification, hexahydroterephthalic acid is abbreviated as HTP, and its trans and cis forms are trans-HTP and cis-HTP, respectively.
It is expressed as HTP, and metal salt means a salt of an alkali metal or alkaline earth metal, and specifically includes sodium, potassium, calcium, barium, etc. Trans-HTP is a useful substance that can lead to trans-4-aminomethylcyclohexanecarboxylic acid, which is known as an antiplasmin agent. Conventionally, the following method is known as a method for producing trans-HTP from cis-trans mixed HTP. (1) A method of extracting and removing cis-HTP from cis and trans mixed HTP with chloroform and obtaining the extraction residue as trans-HTP [Ber., 67 , 1785,
(1934)] (2) Cis- and trans-mixed HTP with water
A method of dissolving and removing HTP and obtaining the residue as trans-HTP [Rec.Trav.Chim., 80 , 588,
(1961)] However, all of these methods have the following drawbacks from an industrial standpoint. That is, in method (1), the difference in solubility between both isomers in chloroform is small, so it is difficult to separate one from the mixed HTP;
The purity of the resulting trans-HTP is low. In method (2), the solubility of cis-HTP in water is low;
A large amount of water is required to dissolve and remove cis-HTP. In addition, in order to dissolve and remove cis-HTP from the crystal,
The purity of trans-HTP obtained is low due to incomplete removal. Since it is not possible to advantageously obtain trans-HTP, conventionally when producing trans-4-aminomethylcyclohexanecarboxylic acid, the next reaction is carried out as a cis and trans mixture as HTP, and the subsequent reaction is carried out as HTP. A method was used to separate the isomers of the product and obtain the trans isomer. As a result of extensive research to overcome these drawbacks of conventional methods, the present inventors found that when HTP is converted into a metal salt, the difference in solubility between the cis and trans isomers in water, water-soluble solvents, and mixtures thereof is reduced. We have found that it is possible to separate and obtain the trans isomer, which is larger and has lower solubility. In other words, a typical example is HTP.
The following table shows the maximum solubility of the cis and trans forms of sodium salts in water, methanol, and ethanol.
【表】
これに基づいて完成された本発明はシス、トラ
ンス混合HTP金属塩の水、水溶性溶媒又はそれ
らの混合液の溶液からトランス−HTP金属塩を
晶析させることからなるトランス−HTP金属塩
又はこれを遊離型としたトランス−HTPの製造
法である。
本発明において金属塩としては本説明の最初に
述べたものが挙げられるが、経済性及び操作性か
らナトリウムが好ましい。
水溶性溶媒としてはアルコール（メタノール、
エタノール及びプロパノール等）、アセトン、ア
セトニトリル及びジオキサン等が挙げられるが、
なかでもアルコールを用いるのが好ましい。
シス、トランス混合HTP金属塩の溶液は、前
段階の反応により得られた反応液のまま又は単離
されたものを溶解して用いるが、新たに溶解させ
る時はなるべく少量の水、水溶性溶媒又はそれら
の混合液に加熱して又は加熱せずに溶解させて製
する。
溶液よりトランス−HTPを晶析させるには、
濃縮及び冷却の操作を適宜組合せて行なう。又水
溶液を濃縮後又は濃縮せずに、これに水溶性溶媒
を加えるなど、溶解性の大きい溶媒と溶解性の小
さい溶媒を組合せて晶析を能率よく行うこともで
きる。
溶解時及び晶析時の温度としては０℃から使用
溶媒の沸点まで用いることができるが、晶析時の
温度についてはトランス−HTP金属塩の溶解度
の関係からなるべく低い方がよいが、通常０〜30
℃の範囲で十分であり、室温に放置して晶析させ
るのが最も簡便である。
本発明において水溶液から晶析させる方法は良
い方法であるが、更に好ましいのはシス、トラン
ス混合HTP金属塩を水に溶解した後濃縮して40
〜50％（ｗ／ｖ）濃度にするか、もしくは始めか
らこの濃度の水溶液を製し、この水溶液に対し２
〜４倍溶量のエタノールを加え数時間放置する方
法であり、最も好ましいのは、シス、トランス混
合HTP金属塩を該金属塩に対し２〜４倍重量の
メタノールに加熱下溶解後室温に数時間放置して
トランス−HTP金属塩を晶析させる方法である。
晶析したトランス−HTP金属塩は濾取し、必
要に応じ水に溶解し濃塩酸等で酸性とした後、遊
離のトランス−HTPとして析出させ濾取するこ
とができる。
本発明方法は従来のシス、トランス混合HTP
からトランス−HTPを製造する方法に比べ、操
作性良くしかも高収率及び高純度にトランス−
HTPを得ることができ工業的に有利である。
尚、原料のシス、トランス混合HTP金属塩は
HTPの合成法として通常行なわれているテレフ
タル酸の該金属塩の接触還元において、反応物か
ら触媒を除去し溶媒を留去するのみで容易に得る
ことも可能であり、又シス−HTP金属塩の異性
化反応後、そのまま又は溶媒を濃縮することによ
つても容易に得ることができる。従つて、テレフ
タル酸金属塩の接触還元、次いでシス−HTP金
属塩の異性化と反応を引き続き行なつてトランス
−HTPを得る場合、本発明方法は最も経済的で
あり、操作面でも一段と有利である。
次に本発明を実施例によつて説明する。
実施例 １
シス−ヘキサヒドロテレフタル酸６ｇ、トラン
ス−ヘキサヒドロテレフタル酸14ｇ、水酸化ナト
リウム12.1ｇおよび水100mlを混合し、常圧下40
mlまで加熱濃縮し、３時間放置、冷却する。析出
した結晶を濾取し、水に溶解後、濃塩酸で酸性と
し、析出したトランス−ヘキサヒドロテレフタル
酸11.9ｇ（収率トランス−HTPに対して85％）
を濾取した。
このものをガスクロマトグラフイーで分析した
ところトランス体の比率は99.5％以上であつた。
実施例 ２
シス−ヘキサヒドロテレフタル酸ナトリウム塩
2.16ｇ及びトランス−ヘキサヒドロテレフタル酸
ナトリウム塩4.32ｇを水15mlに熱時溶解した後、
メタノール30mlを加え３時間放置、冷却する。析
出した結晶を濾取した後、実施例１と同様の操作
を行ないトランス−ヘキサヒドロテレフタル酸
3.1ｇを得た。（収率トランス−HTPナトリウム
塩に対して90％）
このものをガスクロマトグラフイーで分析した
ところトランス体比率は99.5％以上であつた。
実施例 ３
シス−ヘキサヒドロテレフタル酸1.72ｇ、トラ
ンス−ヘキサヒドロテレフタル酸3.44ｇ、水酸化
カリウム3.36ｇおよび水25mlを混合し、常圧下10
mlまで濃縮し、エタノール30mlを加え３時間放
置、冷却する。析出した結晶を濾取した後、実施
例１と同様の操作を行ない、トランス−ヘキサヒ
ドロテレフタル酸2.1ｇを得た。（収率トランス−
HTPに対して61％）
実施例 ４
シス−ヘキサヒドロテレフタル酸1.72ｇ、トラ
ンス−ヘキサヒドロテレフタル酸3.44ｇ、水酸化
バリウム5.14ｇおよび水25mlを混合し、常圧下10
mlまで濃縮し、アセトン30mlを加えて３時間放
置、冷却する。析出した結晶を濾取した後、実施
例１と同様の操作を行ない、トランス−ヘキサヒ
ドロテレフタル酸3.19ｇを得た。（収率トランス
−HTPに対して93％）
実施例 ５
シス−ヘキサヒドロテレフタル酸ナトリウム塩
2.16ｇ及びトランス−ヘキサヒドロテレフタル酸
ナトリウム塩4.32ｇを水に溶解した後、濃縮乾固
する。残査にメタノール30mlを熱時加え３時間撹
拌した後３時間放置、冷却する。析出した結晶を
濾取した後、実施例１と同様の操作を行ない、ト
ランス−ヘキサヒドロテレフタル酸3.1ｇを得た。
（収率トランス−HTPナトリウム塩に対して90
％）[Table] The present invention, which was completed based on this, consists of crystallizing a trans-HTP metal salt from a solution of water, a water-soluble solvent, or a mixture thereof of a cis- and trans-mixed HTP metal salt. This is a method for producing trans-HTP in its salt or free form. In the present invention, the metal salts include those mentioned at the beginning of this description, but sodium is preferred from the viewpoint of economy and operability. Alcohol (methanol,
(ethanol, propanol, etc.), acetone, acetonitrile, dioxane, etc.
Among them, it is preferable to use alcohol. The solution of cis and trans mixed HTP metal salt is used as it is or by dissolving the isolated solution obtained in the previous step, but when newly dissolving it, use as little water or a water-soluble solvent as possible. Or, it can be produced by dissolving it in a mixture thereof with or without heating. To crystallize trans-HTP from solution,
Concentration and cooling operations are performed in appropriate combinations. Furthermore, crystallization can be efficiently performed by combining a solvent with high solubility and a solvent with low solubility, such as by adding a water-soluble solvent to the aqueous solution after concentrating or without concentrating. The temperature during dissolution and crystallization can range from 0°C to the boiling point of the solvent used, but the temperature during crystallization should be as low as possible in relation to the solubility of the trans-HTP metal salt, but it is usually 0°C. ~30
℃ range is sufficient, and it is easiest to crystallize by standing at room temperature. In the present invention, the method of crystallizing from an aqueous solution is a good method, but it is more preferable to dissolve the cis and trans mixed HTP metal salt in water and then concentrate it.
~50% (w/v) concentration, or prepare an aqueous solution with this concentration from the beginning and add 2
This is a method of adding ~4 times the amount of ethanol and leaving it for several hours.The most preferred method is to dissolve the cis and trans mixed HTP metal salt in methanol that is 2 to 4 times the weight of the metal salt under heating, and then let it cool to room temperature for several hours. This is a method in which the trans-HTP metal salt is crystallized by standing for a period of time. The crystallized trans-HTP metal salt can be collected by filtration, and if necessary, dissolved in water and made acidic with concentrated hydrochloric acid or the like, and then precipitated as free trans-HTP and collected by filtration. The method of the present invention is based on conventional cis-trans mixed HTP.
Compared to the method of producing trans-HTP from
HTP can be obtained, which is industrially advantageous. In addition, the raw material cis and trans mixed HTP metal salt is
In the catalytic reduction of the metal salt of terephthalic acid, which is commonly performed as a synthesis method for HTP, it is possible to easily obtain the metal salt by simply removing the catalyst from the reactant and distilling off the solvent. After the isomerization reaction, it can be easily obtained as it is or by concentrating the solvent. Therefore, if the catalytic reduction of the terephthalic acid metal salt is followed by the isomerization and reaction of the cis-HTP metal salt to obtain trans-HTP, the process of the present invention is the most economical and more advantageous in terms of operation. be. Next, the present invention will be explained with reference to examples. Example 1 6 g of cis-hexahydroterephthalic acid, 14 g of trans-hexahydroterephthalic acid, 12.1 g of sodium hydroxide and 100 ml of water were mixed, and the mixture was heated for 40 minutes under normal pressure.
Heat and concentrate to ml, leave for 3 hours, and cool. The precipitated crystals were collected by filtration, dissolved in water, and acidified with concentrated hydrochloric acid to precipitate 11.9 g of trans-hexahydroterephthalic acid (yield: 85% based on trans-HTP).
was collected by filtration. When this product was analyzed by gas chromatography, the ratio of trans isomer was over 99.5%. Example 2 Cis-hexahydroterephthalic acid sodium salt
After hot dissolving 2.16 g and 4.32 g of trans-hexahydroterephthalic acid sodium salt in 15 ml of water,
Add 30 ml of methanol and leave to cool for 3 hours. After filtering the precipitated crystals, the same operation as in Example 1 was performed to obtain trans-hexahydroterephthalic acid.
3.1g was obtained. (Yield: 90% based on trans-HTP sodium salt) When this product was analyzed by gas chromatography, the trans isomer ratio was 99.5% or more. Example 3 1.72 g of cis-hexahydroterephthalic acid, 3.44 g of trans-hexahydroterephthalic acid, 3.36 g of potassium hydroxide and 25 ml of water were mixed, and the mixture was heated for 10 minutes under normal pressure.
Concentrate to 1 ml, add 30 ml of ethanol, let stand for 3 hours, and cool. After filtering the precipitated crystals, the same operation as in Example 1 was performed to obtain 2.1 g of trans-hexahydroterephthalic acid. (yield trans-
(61% based on HTP) Example 4 1.72 g of cis-hexahydroterephthalic acid, 3.44 g of trans-hexahydroterephthalic acid, 5.14 g of barium hydroxide and 25 ml of water were mixed, and the mixture was heated for 10 minutes under normal pressure.
Concentrate to ml, add 30ml of acetone, leave for 3 hours, and cool. After collecting the precipitated crystals by filtration, the same operation as in Example 1 was performed to obtain 3.19 g of trans-hexahydroterephthalic acid. (Yield 93% based on trans-HTP) Example 5 Cis-hexahydroterephthalic acid sodium salt
After dissolving 2.16 g and 4.32 g of trans-hexahydroterephthalic acid sodium salt in water, the solution was concentrated to dryness. Add 30 ml of methanol to the residue while hot, stir for 3 hours, leave for 3 hours, and cool. After collecting the precipitated crystals by filtration, the same operation as in Example 1 was performed to obtain 3.1 g of trans-hexahydroterephthalic acid.
(Yield trans-90 for HTP sodium salt
%)
Claims (1)
ロテレフタル酸金属塩の水、水溶性溶媒又はそれ
らの混合液の溶液からトランス−ヘキサヒドロテ
レフタル酸金属塩を晶析させ、所望によりこれを
遊離型とすることを特徴とするトランス−ヘキサ
ヒドロテレフタル酸又はその金属塩の製法。1 Crystallize trans-hexahydroterephthalate metal salt from a solution of water, a water-soluble solvent, or a mixture thereof of hexahydroterephthalate metal salt containing a mixture of cis and trans forms, and optionally convert it into a free form. A method for producing trans-hexahydroterephthalic acid or a metal salt thereof, characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3243682A JPH0231706B2 (en) | 1982-03-03 | 1982-03-03 | TORANSUUHEKISAHIDOROTEREFUTARUSANNOSEIHO |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3243682A JPH0231706B2 (en) | 1982-03-03 | 1982-03-03 | TORANSUUHEKISAHIDOROTEREFUTARUSANNOSEIHO |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58150539A JPS58150539A (en) | 1983-09-07 |
| JPH0231706B2 true JPH0231706B2 (en) | 1990-07-16 |
Family
ID=12358897
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3243682A Expired - Lifetime JPH0231706B2 (en) | 1982-03-03 | 1982-03-03 | TORANSUUHEKISAHIDOROTEREFUTARUSANNOSEIHO |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0231706B2 (en) |
-
1982
- 1982-03-03 JP JP3243682A patent/JPH0231706B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58150539A (en) | 1983-09-07 |
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