JPH029023B2 - - Google Patents
Info
- Publication number
- JPH029023B2 JPH029023B2 JP2498682A JP2498682A JPH029023B2 JP H029023 B2 JPH029023 B2 JP H029023B2 JP 2498682 A JP2498682 A JP 2498682A JP 2498682 A JP2498682 A JP 2498682A JP H029023 B2 JPH029023 B2 JP H029023B2
- Authority
- JP
- Japan
- Prior art keywords
- trans
- aht
- acid
- ammonia
- htp
- 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 27
- 238000004519 manufacturing process Methods 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 229910021529 ammonia Inorganic materials 0.000 claims description 10
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 claims description 9
- 125000005907 alkyl ester group Chemical group 0.000 claims description 6
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 5
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- 235000011114 ammonium hydroxide Nutrition 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- -1 trans-hexahydroterephthalic acid ester Chemical class 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 238000007112 amidation reaction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- KRJHRNUTLDTSKY-MGCOHNPYSA-N CCOC(=O)[C@H]1CC[C@@H](CC1)C(=O)OCC Chemical compound CCOC(=O)[C@H]1CC[C@@H](CC1)C(=O)OCC KRJHRNUTLDTSKY-MGCOHNPYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- BXDZOYLPNAIDOC-UHFFFAOYSA-N N-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]-1-[2-[2-[2-[2-[2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl]amino]ethoxy]ethoxy]ethoxy]ethylamino]-2-oxoethyl]piperidine-4-carboxamide Chemical compound CC(C)(C)c1cnc(CSc2cnc(NC(=O)C3CCN(CC(=O)NCCOCCOCCOCCNc4cccc5C(=O)N(C6CCC(=O)NC6=O)C(=O)c45)CC3)s2)o1 BXDZOYLPNAIDOC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- GYDJEQRTZSCIOI-UHFFFAOYSA-N Tranexamic acid Chemical compound NCC1CCC(C(O)=O)CC1 GYDJEQRTZSCIOI-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- LJYTWOBAOVEHBG-UHFFFAOYSA-N azane;cyclohexane-1,4-dicarboxylic acid Chemical compound N.N.OC(=O)C1CCC(C(O)=O)CC1 LJYTWOBAOVEHBG-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- LNGAGQAGYITKCW-ZKCHVHJHSA-N chembl3186827 Chemical compound COC(=O)[C@H]1CC[C@H](C(=O)OC)CC1 LNGAGQAGYITKCW-ZKCHVHJHSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940012957 plasmin Drugs 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明はトランス−４−カルボキサミドシクロ
ヘキサン−１−カルボン酸（以下トランス−
AHTと略す）の製造法に関する。Detailed Description of the Invention The present invention relates to trans-4-carboxamide cyclohexane-1-carboxylic acid (hereinafter trans-4-carboxamide cyclohexane-1-carboxylic acid).
Regarding the manufacturing method of AHT (abbreviated as AHT).
トランス−AHTは無水酢酸等で脱水後、ラネ
ーニツケルで接触還元すると抗プラスミン作用を
有するトランス−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出来る有用な物質であ
り、その製造法としては既に次のような方法が知
られている。 Trans-AHT is a useful substance that can be converted to trans-4-aminomethylcyclohexanecarboxylic acid, which has an anti-plasmin effect, by dehydration with acetic anhydride and catalytic reduction with Raney nickel. methods are known.
(1) トランス−ヘキサヒドロテレフタル酸エステ
ルを酸触媒を用いて部分加水分解してトランス
−ヘキサヒドロテレフタル酸モノエステルと
し、このモノエステルをアンモニア水と反応さ
せて、トランス−AHTを製造する方法（特公
昭43−14210）
(2) ヘキサヒドロテレフタル酸アンモニウム塩と
ヘキサヒドロテレフタル酸（以下HTPと略す）
とを混合し、加熱し、４−カルボキサミドシク
ロヘキサン−１−カルボン酸を製造する方法
（特開昭49−110646）
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)の製造法
ではトランス−ヘキサヒドロテレフタル酸エステ
ルの部分加水分解が低収率であり、しかも生成し
たトランス−ヘキサヒドロテレフタル酸モノエス
テルの分離が困難である。(2)の製造法は高温を要
し、低収率である。しかも生成物である４−カル
ボキサミドシクロヘキサン−１−カルボン酸はシ
ス、トランスの混合物であり、トランス−AHT
の製造には適さない。(1) A method for producing trans-AHT by partially hydrolyzing trans-hexahydroterephthalic acid ester using an acid catalyst to produce trans-hexahydroterephthalic acid monoester, and reacting this monoester with aqueous ammonia ( (2) Hexahydroterephthalic acid ammonium salt and hexahydroterephthalic acid (hereinafter abbreviated as HTP)
A method for producing 4-carboxamidocyclohexane-1-carboxylic acid by mixing and heating (Japanese Patent Application Laid-Open No. 110646/1983) However, all of these methods have the following drawbacks from an industrial standpoint. There is. That is, in the production method (1), the yield of partial hydrolysis of trans-hexahydroterephthalic acid ester is low, and moreover, it is difficult to separate the produced trans-hexahydroterephthalic acid monoester. Production method (2) requires high temperatures and has a low yield. Moreover, the product 4-carboxamide cyclohexane-1-carboxylic acid is a mixture of cis and trans, and trans-AHT.
Not suitable for manufacturing.
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、本発明に到達した。即ち
本発明はトランス−ヘキサヒドロテレフタル酸低
級アルキルエステルを水の存在下反応液中の濃度
が10〜20％（ｗ／ｖ）のアンモニアと10〜100℃
の温度で反応させることにより、トランス−
AHTを製造する方法である。 The present inventors have conducted extensive research to overcome these drawbacks of the conventional methods, and as a result, have arrived at the present invention. That is, in the present invention, trans-hexahydroterephthalic acid lower alkyl ester is mixed with ammonia at a concentration of 10 to 20% (w/v) in the reaction solution at 10 to 100°C in the presence of water.
By reacting at a temperature of
This is a method of manufacturing AHT.
本発明において用いるトランス−ヘキサヒドロ
テレフタル酸低級アルキルエステルの低級アルキ
ル基としてはメチル、エチル、プロピル等を挙げ
ることができる。 Examples of the lower alkyl group of the trans-hexahydroterephthalic acid lower alkyl ester used in the present invention include methyl, ethyl, and propyl.
本発明を行うには、トランス−ヘキサヒドロテ
レフタル酸低級アルキルエステルを水の存在下、
反応液中のアンモニア濃度について１〜28％
（ｗ／ｖ）で及び反応温度について０〜200℃で通
常数時間から十数時間反応させる。水はエステル
の部分加水分解に必要な量以上あれば良く、従つ
て原料のヘキサヒドロテレフタル酸低級アルキル
エステルに対し等モル以上あれば良い。アンモニ
アはアンモニア水として加えるか、又はアンモニ
アガスとして加えても良い。溶媒としては水又は
反応に必要な水と共にアルコール、アセトン、ア
セトニトリル、ベンゼン、トルエン及びエーテル
等の溶媒を用いることができるが反応終了後の処
理操作上水又は水溶性溶媒を含水溶媒として用い
るのが好ましく、特に含水アルコール（メタノー
ル、エタノール及びプロパノール等）、含水アセ
トン及び含水アセトニトリル等を用いるのが好ま
しい。 To carry out the present invention, trans-hexahydroterephthalic acid lower alkyl ester is added in the presence of water.
Regarding the ammonia concentration in the reaction solution: 1-28%
(w/v) and at a reaction temperature of 0 to 200°C, usually for several hours to more than ten hours. It is sufficient that the amount of water is at least the amount required for partial hydrolysis of the ester, and therefore, it is sufficient that the amount of water is at least equimolar to the raw material lower alkyl hexahydroterephthalate. Ammonia may be added as aqueous ammonia or as ammonia gas. As a solvent, water or a solvent such as alcohol, acetone, acetonitrile, benzene, toluene, and ether can be used together with the water necessary for the reaction, but for processing operations after the reaction is completed, it is preferable to use water or a water-soluble solvent as the water-containing solvent. It is particularly preferable to use hydrous alcohols (methanol, ethanol, propanol, etc.), hydrous acetone, hydrous acetonitrile, and the like.
この反応の初期段階では、エステルが部分加水
分解したトランス−４−低級アルコキシカルボニ
ルシクロヘキサン−１−カルボン酸（以下モノエ
ステルと略す）及びエステルがモノアミド化され
たトランス−４−カルボキサミドシクロヘキサン
−１−カルボン酸低級アルキルエステル（以下モ
ノエステルモノアミドと略す）が生成する。又反
応の後期にはモノエステルはさらに加水分解され
トランス−HTPとなるか、又はアミド化されト
ランス−AHTになり、一方モノエステルモノア
ミドはトランス−AHTか又はトランス−１，４
−ジカルボキサミドシクロヘキサン（以下トラン
ス−DAC）になる。 In the initial stage of this reaction, trans-4-lower alkoxycarbonylcyclohexane-1-carboxylic acid (hereinafter abbreviated as monoester) in which the ester is partially hydrolyzed and trans-4-carboxamidocyclohexane-1-carboxylic acid in which the ester is monoamidated are used. An acid lower alkyl ester (hereinafter abbreviated as monoester monoamide) is produced. Also, in the later stages of the reaction, the monoester is further hydrolyzed to trans-HTP or amidated to trans-AHT, while the monoester monoamide is either trans-AHT or trans-1,4
- Dicarboxamide cyclohexane (hereinafter referred to as trans-DAC).
この時、反応の温度、反応液中のアンモニア濃
度及び３つの生成物であるトランス−HTP、ト
ランス−AHT及びトランス−DACのそれぞれの
生成率との間に密接な関係があり、アンモニア濃
度について低すぎるとトランス−HTP、高すぎ
るとトランス−DACの生成率が高まり、又温度
については高すぎるとトランス−HTP、低すぎ
るとトランス−DACの生成率が高まることが認
められた。従つて反応温度及び反応液中のアンモ
ニア濃度を調節することによつてエステルの加水
分解反応速度及びアミド化反応速度を調整し、ト
ランス−HTP及びトランス−DACよりもトラン
ス−AHTの生成率を高めることが可能となり、
アンモニア濃度については10〜20％（ｗ／ｖ）が
好ましく、又温度については10〜100℃が好まし
く、特に50〜70℃が最も好ましいことが認められ
た。このように反応温度及び反応液中のアンモニ
ア濃度を調節してトランス−AHTの生成率が最
大になつた時、３つの生成物組成はおよそ次のよ
うな比、トランス−HTP：トランス−DAC：ト
ランス−AHT＝１：２：７（モル比）になつた。 At this time, there is a close relationship between the reaction temperature, the ammonia concentration in the reaction solution, and the production rate of each of the three products, trans-HTP, trans-AHT, and trans-DAC. It was found that when the temperature is too high, the generation rate of trans-HTP increases, and when the temperature is too high, the generation rate of trans-DAC increases; when the temperature is too high, the generation rate of trans-HTP increases, and when the temperature is too low, the generation rate of trans-DAC increases. Therefore, by adjusting the reaction temperature and ammonia concentration in the reaction solution, the ester hydrolysis reaction rate and amidation reaction rate can be adjusted to increase the production rate of trans-AHT more than trans-HTP and trans-DAC. It becomes possible to
It has been found that the ammonia concentration is preferably 10-20% (w/v), and the temperature is preferably 10-100°C, most preferably 50-70°C. When the reaction temperature and ammonia concentration in the reaction solution are adjusted to maximize the production rate of trans-AHT, the composition of the three products is approximately in the following ratio: trans-HTP:trans-DAC: Trans-AHT=1:2:7 (molar ratio).
反応終了後、トランス−AHTを単離するには
次のようにすればよい。即ちトランス−DACは
水又は含水溶媒に溶解しないので濾過等の手段で
除去し、濾液を常圧下濃縮するとトランス−
AHTのアンモニウム塩が分解し、アンモニアが
留去し、トランス−AHTの結晶が析出する。こ
れを濾取することによつて高純度にトランス−
AHTを得ることができる。又トランス−AHT
を濾取した後の濾液を酸性にするとトランス−
HTPが回収され、これは酸触媒を用いてアルコ
ールと反応させると容易にエステルに導くことが
でき、原料として再利用できる。 After the reaction is complete, trans-AHT can be isolated as follows. That is, since trans-DAC does not dissolve in water or water-containing solvents, it is removed by means such as filtration, and the filtrate is concentrated under normal pressure.
The ammonium salt of AHT decomposes, ammonia is distilled off, and crystals of trans-AHT are precipitated. By filtering this, high purity trans-
You can get AHT. Also trans-AHT
When the filtrate after filtering is made acidic, trans-
HTP is recovered, which can be easily converted into an ester by reacting with an alcohol using an acid catalyst, and can be reused as a raw material.
本発明を実施する場合次のようにしてトランス
−AHTを製造することもできる。即ちトランス
−HTPを原料としてアルコール塩酸でエステル
化し、生成するトランス−ヘキサヒドロテレフタ
ル酸低級アルキルエステルを結晶として分離する
ことなく、続いて反応液にアンモニア水を加えア
ミド化反応を行い一挙にトランス−HTPからト
ランス−AHTを得ることもでき、経済的かつ操
作面でも有利である。 When carrying out the present invention, trans-AHT can also be produced as follows. That is, trans-HTP is esterified with alcohol hydrochloric acid as a raw material, and without separating the resulting trans-hexahydroterephthalic acid lower alkyl ester as crystals, aqueous ammonia is subsequently added to the reaction solution to carry out the amidation reaction, resulting in trans-HTP all at once. Trans-AHT can also be obtained from HTP, which is advantageous both economically and operationally.
本発明方法は従来知られている製造法に比し、
操作性が良く、しかも高収率及び高純度にトラン
ス−AHTを製造することができるものである。 Compared to conventionally known manufacturing methods, the method of the present invention has the following advantages:
It has good operability and can produce trans-AHT in high yield and purity.
次に本発明を実施例によつて説明する。 Next, the present invention will be explained with reference to examples.
実施例 １
トランス−ヘキサヒドロテレフタル酸ジメチル
エステル20ｇを20％アンモニア水150ml及びメタ
ノール50mlに懸濁し、密閉下70℃で７時間加熱撹
拌する。冷後、不溶物を濾去し濾液を濃縮し、ア
ンモニアを留去させると結晶が析出し、トランス
−４−カルボキサミドシクロヘキサン−１−カル
ボン酸12.0ｇ（収率70％）が得られた。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−４−カルボキサミドシクロヘキサン−１−
カルボン酸の純度は99％以上であつた。Example 1 20 g of trans-hexahydroterephthalic acid dimethyl ester is suspended in 150 ml of 20% aqueous ammonia and 50 ml of methanol, and the suspension is heated and stirred at 70° C. for 7 hours under closed conditions. After cooling, insoluble materials were removed by filtration, the filtrate was concentrated, and ammonia was distilled off to precipitate crystals, yielding 12.0 g (yield: 70%) of trans-4-carboxamidocyclohexane-1-carboxylic acid. Analysis of this product by gas chromatography revealed that trans-4-carboxamide cyclohexane-1-
The purity of the carboxylic acid was over 99%.
実施例 ２
トランス−ヘキサヒドロテレフタル酸ジエチル
エステル22.8ｇを28％アンモニア水100ml及びア
セトン50mlに懸濁し、密閉下50℃で10時間加熱撹
拌する。冷後、不溶物を濾去し、実施例１と同様
の処理を行い、トランス−４−カルボキサミドシ
クロヘキサン−１−カルボン酸11.1ｇ（収率65
％）（純度99％以上）を得た。Example 2 22.8 g of trans-hexahydroterephthalic acid diethyl ester is suspended in 100 ml of 28% aqueous ammonia and 50 ml of acetone, and the suspension is heated and stirred at 50° C. for 10 hours under closed conditions. After cooling, insoluble matters were removed by filtration, and the same treatment as in Example 1 was performed to obtain 11.1 g of trans-4-carboxamidocyclohexane-1-carboxylic acid (yield: 65
%) (purity of 99% or more).
実施例 ３
トランス−ヘキサヒドロテレフタル酸ジプロピ
ルエステル25.6ｇをアンモニア水250mlに懸濁し、
100℃で７時間加熱撹拌する。冷後、不溶物を濾
去し、濾液を実施例１と同様の処理を行い、トラ
ンス−４−カルボキサミドシクロヘキサン−１−
カルボン酸10.2ｇ（収率60％）（純度99％以上）
を得た。Example 3 25.6 g of trans-hexahydroterephthalic acid dipropyl ester was suspended in 250 ml of aqueous ammonia,
Heat and stir at 100°C for 7 hours. After cooling, insoluble matters were removed by filtration, and the filtrate was treated in the same manner as in Example 1 to obtain trans-4-carboxamide cyclohexane-1-
Carboxylic acid 10.2g (yield 60%) (purity 99% or more)
I got it.
実施例 ４
トランス−ヘキサヒドロテレフタル酸17.2ｇを
メタノール60ml及び濃塩酸３mlに加え３時間加熱
還流し、冷後28％アンモニア水100mlを加え、密
閉下70℃で７時間加熱撹拌する。冷後、不溶物を
濾去し、濾液を実施例１と同様の処理を行い、ト
ランス−４−カルボキサミドシクロヘキサン−１
−カルボン酸12.8ｇ（収率トランス−HTPに対
して75％）（純度99％以上）を得た。Example 4 17.2 g of trans-hexahydroterephthalic acid was added to 60 ml of methanol and 3 ml of concentrated hydrochloric acid, heated under reflux for 3 hours, cooled, 100 ml of 28% ammonia water was added, and the mixture was heated and stirred at 70° C. for 7 hours under closed conditions. After cooling, insoluble matters were removed by filtration, and the filtrate was treated in the same manner as in Example 1 to obtain trans-4-carboxamide cyclohexane-1.
12.8 g of -carboxylic acid (yield 75% based on trans-HTP) (purity 99% or more) was obtained.
Claims (1)
ルキルエステルを水の存在下反応液中の濃度が10
〜20％（ｗ／ｖ）のアンモニアと10〜100℃の温
度で反応させることを特徴とするトランス−４−
カルボキサミドシクロヘキサン−１−カルボン酸
の製造法。1 Trans-hexahydroterephthalic acid lower alkyl ester in the presence of water at a concentration of 10
Trans-4- characterized by reacting with ~20% (w/v) ammonia at a temperature of 10 to 100°C
Method for producing carboxamide cyclohexane-1-carboxylic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2498682A JPS58144353A (en) | 1982-02-18 | 1982-02-18 | Preparation of trans-4-carboxamidocyclohexane-1- carboxylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2498682A JPS58144353A (en) | 1982-02-18 | 1982-02-18 | Preparation of trans-4-carboxamidocyclohexane-1- carboxylic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58144353A JPS58144353A (en) | 1983-08-27 |
| JPH029023B2 true JPH029023B2 (en) | 1990-02-28 |
Family
ID=12153296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2498682A Granted JPS58144353A (en) | 1982-02-18 | 1982-02-18 | Preparation of trans-4-carboxamidocyclohexane-1- carboxylic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58144353A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0627108B2 (en) * | 1988-10-03 | 1994-04-13 | 昭和電工株式会社 | Method for producing 4-carboxamide cyclohexanecarboxylic acid esters |
-
1982
- 1982-02-18 JP JP2498682A patent/JPS58144353A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58144353A (en) | 1983-08-27 |
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