JPH0441449A - Production of cyclohexane-1,2-diol - Google Patents
Production of cyclohexane-1,2-diolInfo
- Publication number
- JPH0441449A JPH0441449A JP14904890A JP14904890A JPH0441449A JP H0441449 A JPH0441449 A JP H0441449A JP 14904890 A JP14904890 A JP 14904890A JP 14904890 A JP14904890 A JP 14904890A JP H0441449 A JPH0441449 A JP H0441449A
- Authority
- JP
- Japan
- Prior art keywords
- cyclohexene
- cyclohexene oxide
- reacting
- diol
- oxide
- 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
- PFURGBBHAOXLIO-WDSKDSINSA-N cyclohexane-1,2-diol Chemical compound O[C@H]1CCCC[C@@H]1O PFURGBBHAOXLIO-WDSKDSINSA-N 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 19
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 claims abstract description 39
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims abstract description 39
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims abstract description 36
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims abstract description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 36
- 150000004967 organic peroxy acids Chemical class 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 238000004821 distillation Methods 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000006227 byproduct Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 230000007423 decrease Effects 0.000 description 6
- -1 alicyclic olefin compound Chemical class 0.000 description 5
- 238000006703 hydration reaction Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000006735 epoxidation reaction Methods 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001944 continuous distillation Methods 0.000 description 2
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000000180 1,2-diols Chemical class 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 239000012045 crude solution Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、医農薬中間体として重要なシクロヘキサン−
１，２−ジオールをシクロヘキセンより効率よく製造す
る方法に関する。Detailed Description of the Invention (Industrial Field of Application) The present invention is directed to cyclohexane, which is important as a pharmaceutical and agricultural intermediate.
The present invention relates to a method for producing 1,2-diol more efficiently than cyclohexene.
（従来の技術）
有機過酸を用いて分枝状ないしは脂環式のオレフィン化
合物からエポキシ化合物を製造する方法は一般によく知
られている。(Prior Art) A method for producing an epoxy compound from a branched or alicyclic olefin compound using an organic peracid is generally well known.
工業的に使用されている有機過酸である過酢酸によるシ
クロヘキセンのエポキシ化によるシクロヘキセンオキシ
ドの製造は、シクロヘキセンオキシドと副生ずる酢酸の
分離が困難であるため全く行なわれていない。The production of cyclohexene oxide by epoxidation of cyclohexene with peracetic acid, an organic peracid used industrially, has not been carried out at all because it is difficult to separate cyclohexene oxide and acetic acid as a by-product.
また、分枝状ないしは脂環式のエポキシドの水和反応に
よるジオールの製造方法は一般的に良く知られている。Furthermore, a method for producing diols by a hydration reaction of branched or alicyclic epoxides is generally well known.
この水和反応はツウベン・フィル（ＨＯＵＢＥＮ−ｗＥ
ＹＬ） 、第Ｖｌ／３巻、（１９６４年）、第４５４〜
４５５頁によれば１００℃よりもはるかい高い温度およ
び１２〜２０バールの高い圧力で数時間水和反応させる
ことが公知であり、該水和反応は触媒なしに進行する。This hydration reaction takes place in the HOUBEN-wE
YL), Volume Vl/3, (1964), No. 454~
According to page 455, it is known to carry out the hydration reaction at temperatures much higher than 100 DEG C. and high pressures of 12 to 20 bar for several hours, the hydration reaction proceeding without a catalyst.
一般的には、より温和な条件で該水和反応を進行させる
ために、酸の添加（ＵＳＰ ３５７６８９０）、アル
カリの添加、脂肪族モノ−（ＤＥ１７９３．２４７、Ｄ
Ｅ ２２０３．８０６）またはポリカルボン酸の塩の
添加（ＤＥ ２２５６９０７）ならびに、第一級、第
二級または第三級アミン塩またはアンモニウム塩の添加
（ＥＰ ２５９６７）により接触される。Generally, in order to proceed with the hydration reaction under milder conditions, addition of acid (USP 3576890), addition of alkali, aliphatic monomer (DE 1793.247, D
E 2203.806) or by addition of salts of polycarboxylic acids (DE 2256907) and by addition of primary, secondary or tertiary amine salts or ammonium salts (EP 25967).
（発明が解決しようとする課題）
以上のようにオレフィン化合物の有機過酸によるエポキ
シ化合物の製造方法およびエポキシドと水との反応によ
り相当するジオールを製造する方法は公知である。(Problems to be Solved by the Invention) As described above, a method for producing an epoxy compound using an organic peracid of an olefin compound and a method for producing a corresponding diol by reacting an epoxide with water are known.
しかしながら、工業的に使用されている有機過酸の１つ
である過酢酸とシクロヘキセンとの反応によるシクロヘ
キセンオキシドの製造は、シクロヘキセンオキシドと副
生ずる酢酸の沸点差が小さく精製分離不可能であるため
に全く行われていない。したがって、過酢酸を使用して
製造したシクロヘキセンオキシドと水との反応によるシ
クロヘキサン−１，２−ジオールの製造は全く行われて
いなかった。However, the production of cyclohexene oxide by reacting peracetic acid, one of the organic peracids used industrially, with cyclohexene is difficult because the difference in boiling point between cyclohexene oxide and acetic acid, which is a by-product, is small and purification and separation is impossible. Not done at all. Therefore, the production of cyclohexane-1,2-diol by the reaction of cyclohexene oxide produced using peracetic acid with water has not been carried out at all.
工業的に使用可能な有機過酸の１つである過酢酸を使用
して製造したシクロヘキセンオキシドと水との反応によ
りシクロヘキサン−１，２−ジオールを製造する方法を
開発するために、本発明者が鋭意検討した結果、過酢酸
とシクロヘキセンとを反応させた後のシクロヘキセンオ
キシド含みの反応粗液と水とを接触させることにより、
高活性および高収率でシクロヘキサン−１，２−ジオル
を製造できることを見い出した。In order to develop a method for producing cyclohexane-1,2-diol by reacting cyclohexene oxide produced using peracetic acid, which is one of industrially usable organic peracids, with water, the present inventors As a result of intensive studies, by bringing the crude reaction solution containing cyclohexene oxide into contact with water after reacting peracetic acid and cyclohexene,
It has been found that cyclohexane-1,2-diol can be produced with high activity and high yield.
（発明の目的）
本発明の目的は、工業的に使用される有機過酸の１つで
ある過酢酸とシクロヘキセンを反応させた反応粗液中の
シクロヘキセンオキシドを未精製のまま、水と反応させ
てシクロヘキサン−１，２ジオールを高活性および高収
率で製造する方法を提供することにある。(Objective of the Invention) The object of the present invention is to react unpurified cyclohexene oxide with water in a crude reaction solution obtained by reacting peracetic acid, which is one of the organic peracids used industrially, with cyclohexene. An object of the present invention is to provide a method for producing cyclohexane-1,2 diol with high activity and high yield.
（課題を解決するための手段）
すなわち、本発明は、
「以下の２つの工程
（ａ）シクロヘキセンと過酢酸を反応させてシクロヘキ
センオキシドを製造する工程
および
（ｂ）上記（ａ）の工程で得られた反応粗液と水とを反
応させて、シクロヘキサン−１，２−ジオルを製造する
工程からなることを特徴とするシクロヘキサン−１，２
−ジオールの製造方法」である。(Means for Solving the Problems) That is, the present invention consists of ``the following two steps (a) a step of reacting cyclohexene and peracetic acid to produce cyclohexene oxide; and (b) a step of producing cyclohexene oxide in the step (a) above. Cyclohexane-1,2-diol is produced by reacting the reaction crude liquid with water to produce cyclohexane-1,2-diol.
- Method for producing diol.
本発明において、シクロヘキセンオキシドを製造する工
程において、使用する過酢酸はシクロヘキセンに対して
、好ましくは、０．５〜３モル倍、より好ましくは１〜
１．５モル倍の範囲で使用される。In the present invention, in the step of producing cyclohexene oxide, the peracetic acid used is preferably 0.5 to 3 times the mole of cyclohexene, more preferably 1 to 3 times the mole of cyclohexene.
It is used in a range of 1.5 times the mole.
また、使用する過酢酸は、通常不活性の溶媒で希釈され
たものが用いられ、過酢酸濃度が高すぎると、副生物が
増加して収率が低下し、過酢酸濃度が低すぎても反応速
度が低下するので、酢酸エチルなどで通常５〜４０重量
％に希釈して使用するのが好ましい。In addition, the peracetic acid used is usually diluted with an inert solvent, and if the peracetic acid concentration is too high, by-products will increase and the yield will decrease; Since the reaction rate decreases, it is preferably used after diluting with ethyl acetate or the like to usually 5 to 40% by weight.
エポキシ化の反応温度としては通常０〜５０℃の任意の
温度で行われ、より好ましくは２０〜４０℃の温度で行
われる。The reaction temperature for epoxidation is usually any temperature from 0 to 50°C, more preferably from 20 to 40°C.
また、反応時間としては、通常１〜５時間間開で行われ
る。The reaction time is usually 1 to 5 hours.
また、反応方式としては、バッチ方式で行われても、連
続方式で行われてもよい。Moreover, the reaction method may be carried out in a batch method or in a continuous method.
本発明における特徴の１つは、工業的に使用されている
過酢酸でシクロヘキセンをエポキシ化してシクロヘキセ
ンオキシドを製造し、蒸留による分離精製の不可能なシ
クロヘキセンオキシドと、副生酢酸を分離精製せずに、
シクロヘキセンオキシドと水とを反応させることにあり
、シクロヘキセンオキシドの精製工程がいらないという
点て工業的メリットは非常に大きい。One of the features of the present invention is that cyclohexene oxide is produced by epoxidizing cyclohexene with peracetic acid, which is used industrially, and cyclohexene oxide, which cannot be separated and purified by distillation, and by-product acetic acid are not separated and purified. To,
The process involves reacting cyclohexene oxide with water, and has a great industrial advantage in that it does not require a purification process for cyclohexene oxide.
本発明において、シクロヘキサン−１，２−ジオールを
製造する工程において、使用する水の量は、シクロヘキ
センオキシド製造工程で生成したシクロヘキセンオキシ
ドに対して、理論量以上にする必要がある。In the present invention, the amount of water used in the process of producing cyclohexane-1,2-diol needs to be greater than the theoretical amount relative to the cyclohexene oxide produced in the cyclohexene oxide production process.
シクロヘキセンオキシドに対して水の使用量が理論量以
下の場合は、生成した１、２−シクロヘキサンジオール
と未反応のシクロヘキセンオキシドとが容易に反応して
目的としない物が生成するため収率が低下したり、触媒
の活性低下が激しくなる。If the amount of water used relative to cyclohexene oxide is less than the theoretical amount, the yield will decrease because the generated 1,2-cyclohexanediol and unreacted cyclohexene oxide will easily react and produce unintended products. or the catalyst activity decreases drastically.
理論量以上であれば特に制限がないが２〜１゜０モル倍
の範囲が適当である。There is no particular restriction as long as it is more than the theoretical amount, but a range of 2 to 1.0 times the mole is appropriate.
水のモル倍率が小さいと理論量以上であっても副反応が
起き収率が低下するので水の下限量は、収率低下の割合
と精製コストから決めるべきである。水のモル倍率が大
きい場合は収率は向上するが精製コストが増大し、反応
器も大きくなる等の不利なことが起きるので得策ではな
い。If the molar ratio of water is small, side reactions will occur even if the amount exceeds the theoretical amount, resulting in a decrease in yield, so the lower limit of water should be determined based on the rate of decrease in yield and purification cost. If the molar ratio of water is large, the yield will improve, but the purification cost will increase and the size of the reactor will also increase, which is not a good idea.
本発明を実施する場合、反応温度は特に制限ないが、工
業的に実施していく場合の設備費等を考慮すると、常圧
下で沸点以下の温度が好ましい。When carrying out the present invention, the reaction temperature is not particularly limited, but in consideration of equipment costs and the like when carrying out the invention industrially, a temperature below the boiling point under normal pressure is preferred.
また、反応温度が余り低いと反応速度が遅くなり、反応
温度が高いと副生物が増加するので、より好ましくは室
温以上１００℃以下が好ましい。Further, if the reaction temperature is too low, the reaction rate will be slow, and if the reaction temperature is high, by-products will increase, so it is more preferably room temperature or higher and 100°C or lower.
本発明を実施する場合、反応時間は反応温度や原料組成
によって異なるが通常数分から数時間の範囲から選択す
れば良い。When carrying out the present invention, the reaction time may vary depending on the reaction temperature and raw material composition, but may generally be selected from a range of several minutes to several hours.
本発明は、工業的に実施する場合回分方式で行ってもよ
いし、連続方式で行ってもよい。When the present invention is carried out industrially, it may be carried out either batchwise or continuously.
本発明におけるもう１つの特徴として、シクロヘキセン
エポキシ化工程で副生じた酢酸および原料過酢酸中に含
まれていた酢酸が、シクロヘキセンオキシドを精製して
いないために、シクロヘキサン−１，２−ジオール製造
工程での触媒として作用するために、特に触媒を添加す
る必要はないことである。Another feature of the present invention is that acetic acid produced as a by-product in the cyclohexene epoxidation process and acetic acid contained in the raw material peracetic acid are removed during the cyclohexane-1,2-diol production process because cyclohexene oxide is not purified. It is not necessary to specifically add a catalyst in order to act as a catalyst.
また、酢酸とシクロヘキセンオキシドの反応速度は水と
シクロヘキセンオキシドとの反応速度に較べると著しく
小さいために、エステルヒドロキシ化合物の副生はほと
んどなく、高活性および高収率でシクロヘキサン−１，
２−ジオールを製造することができる。In addition, since the reaction rate between acetic acid and cyclohexene oxide is significantly lower than that between water and cyclohexene oxide, there is almost no by-product of ester hydroxy compounds, and cyclohexane-1,
2-diol can be produced.
（発明の効果）
本発明によると、工業的に使用される有機過酸の１つで
ある過酢酸とシクロヘキセンを反応させた反応粗液中の
シクロヘキセンオキシドを未精製のまま、水と反応させ
てシクロヘキサン−１，２ジオールを高活性および高収
率で製造することができる。(Effect of the invention) According to the present invention, cyclohexene oxide in the crude reaction solution obtained by reacting peracetic acid, which is one of the organic peracids used industrially, with cyclohexene is reacted with water in an unpurified state. Cyclohexane-1,2 diol can be produced with high activity and high yield.
次に、実施例を上げて本発明を説明するが本発明はこれ
らの実施例によって何ら限定されるものではない。Next, the present invention will be explained with reference to Examples, but the present invention is not limited to these Examples in any way.
実施例
くシクロヘキセンオキシド製造工程〉
シクロヘキセン４１ｇをガラスのフラスコに仕込み、３
０℃に撹拌しながら昇温する。Example: Cyclohexene oxide manufacturing process> 41 g of cyclohexene was charged into a glass flask, and 3
Raise the temperature to 0°C with stirring.
３０℃に達したところで３０％の過酢酸をモル比１．２
倍になるように２時間かけてゆっくり添加した。When the temperature reached 30℃, add 30% peracetic acid at a molar ratio of 1.2.
The mixture was slowly added over 2 hours so that the volume doubled.
反応により発熱するので３０℃になるように、外部から
冷却した。Since the reaction generated heat, it was externally cooled to 30°C.
過酢酸添加終了後１時間３０℃に保持することで反応を
完結させた。After the addition of peracetic acid was completed, the reaction was completed by maintaining the temperature at 30°C for 1 hour.
反応粗液のガスクロマトグラフィーによる分析の結果シ
クロヘキセンオキサシトの収率９３％得た。Analysis of the reaction crude liquid by gas chromatography showed that a yield of cyclohexene oxacite was 93%.
くシクロヘキサン−１，２−ジオール製造工程〉水５０
ｇをガラスのフラスコに仕込み、７０℃に撹拌しながら
昇温した。Cyclohexane-1,2-diol manufacturing process> Water 50
g was placed in a glass flask, and the temperature was raised to 70° C. with stirring.
７０℃に達したところでシクロヘキセンオキシド製造工
程で得られた酢酸およびシクロヘキセンオキシドを含む
溶液２１．６ｇを２時間かけてゆっくり添加した。When the temperature reached 70°C, 21.6 g of a solution containing acetic acid and cyclohexene oxide obtained in the cyclohexene oxide manufacturing process was slowly added over 2 hours.
前記溶液添加終了後、すぐに反応粗液をガスクロマトグ
ラフィーにより分析した結果、シクロへ牛サンー１，２
−ジオールをシクロヘキセンオキシド基準で収率９４％
で得た。Immediately after the addition of the solution was completed, the crude reaction solution was analyzed by gas chromatography.
- Yield of diol is 94% based on cyclohexene oxide
I got it.
比較例
〈シクロヘキセンオキシドの精製〉
４０段４０ｍｍφオールダシヨウ連続蒸留塔を用いて、
実施例のくシクロヘキセンオキシド製造工程〉で得られ
る反応粗液のモデル液がらのシクロヘキセンオキシドの
精製を行った。Comparative Example <Purification of cyclohexene oxide> Using a 40-stage 40 mmφ old continuous distillation column,
Cyclohexene oxide was purified from a model solution of the reaction crude solution obtained in the cyclohexene oxide manufacturing process of the example.
モデル粗液（酢酸エチル５２，０重量％、酢酸２３．０
重量％、シクロヘキセンオキシド２５゜０重量％）をリ
ボイラーから２３段目に１８２ｇ／ｈで仕込み、還流比
３、トップ圧力４０ｍｍＨｇで連続蒸留したところ、留
出液１０９ｇ／ｈ（酢酸エチル７１．２重量％、酢酸２
６．７重量％、シクロヘキセンオキシド２８１重量％）
、缶出液５５．５ｇ／ｈ （酢酸４．４重量％、シクロ
ヘキセンオキシド４５．９重量％、ハイボイラー４９６
７重量％）およびトラップ液１７．５ｇ／ｈを得た。Model crude liquid (ethyl acetate 52.0% by weight, acetic acid 23.0%
When 182 g/h of cyclohexene oxide (25% by weight, 25% by weight of cyclohexene oxide) was charged into the 23rd stage from the reboiler and continuous distillation was carried out at a reflux ratio of 3 and a top pressure of 40 mmHg, the distillate was 109 g/h (71.2% by weight of ethyl acetate). %, acetic acid 2
6.7% by weight, cyclohexene oxide 281% by weight)
, bottoms 55.5g/h (acetic acid 4.4% by weight, cyclohexene oxide 45.9% by weight, high boiler 496
7% by weight) and 17.5 g/h of trap liquid were obtained.
この比較例は、通常実験室的に使用される段数の多い塔
を用いても、酢酸の沸点１１８℃とシクロヘキセンオキ
シドの沸点１２９℃が近いためにシクロヘキセンオキシ
ドを蒸留分離できないことを示している。This comparative example shows that even if a column with a large number of plates, which is normally used in a laboratory, is used, cyclohexene oxide cannot be separated by distillation because the boiling point of acetic acid, 118°C, and the boiling point of cyclohexene oxide, 129°C, are close to each other.
Claims (1)
センオキシドを製造する工程 および （ｂ）上記（ａ）の工程で得られた反応粗液と水とを反
応させて、シクロヘキサン−１，２−ジオールを製造す
る工程 からなることを特徴とするシクロヘキサン−１，２−ジ
オールの製造方法。[Claims] The following two steps (a) A step of reacting cyclohexene and peracetic acid to produce cyclohexene oxide, and (b) Reacting the crude reaction liquid obtained in step (a) above with water. A method for producing cyclohexane-1,2-diol, the method comprising the steps of producing cyclohexane-1,2-diol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14904890A JPH0441449A (en) | 1990-06-07 | 1990-06-07 | Production of cyclohexane-1,2-diol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14904890A JPH0441449A (en) | 1990-06-07 | 1990-06-07 | Production of cyclohexane-1,2-diol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0441449A true JPH0441449A (en) | 1992-02-12 |
Family
ID=15466511
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14904890A Pending JPH0441449A (en) | 1990-06-07 | 1990-06-07 | Production of cyclohexane-1,2-diol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0441449A (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0645363A4 (en) * | 1993-04-09 | 1995-11-02 | Asahi Chemical Ind | Process for producing adipic acid. |
| US7385096B2 (en) | 2002-01-24 | 2008-06-10 | Japan Science And Technology Agency | Process for producing 1,2-diol |
| WO2013101968A1 (en) * | 2011-12-30 | 2013-07-04 | E. I. Du Pont De Nemours And Company | Process for the production of hexanediols |
| US8846985B2 (en) | 2012-04-27 | 2014-09-30 | E I Du Pont De Nemours And Company | Production of alpha, omega-diols |
| US8859826B2 (en) | 2012-04-27 | 2014-10-14 | E I Du Pont De Nemours And Company | Production of alpha, omega-diols |
| US8865940B2 (en) | 2011-12-30 | 2014-10-21 | E I Du Pont De Nemours And Company | Process for preparing 1,6-hexanediol |
| US8884036B2 (en) | 2011-12-30 | 2014-11-11 | E I Du Pont De Nemours And Company | Production of hydroxymethylfurfural from levoglucosenone |
| US8884035B2 (en) | 2011-12-30 | 2014-11-11 | E I Du Pont De Nemours And Company | Production of tetrahydrofuran-2, 5-dimethanol from isosorbide |
| US8889922B2 (en) | 2011-12-30 | 2014-11-18 | E I Du Pont De Nemours And Company | Process for preparing 1, 6-hexanediol |
| US8889912B2 (en) | 2011-12-30 | 2014-11-18 | E I Du Pont De Nemours And Company | Process for preparing 1,6-hexanediol |
| US9018423B2 (en) | 2012-04-27 | 2015-04-28 | E I Du Pont De Nemours And Company | Production of alpha, omega-diols |
| JP2019112368A (en) * | 2017-12-26 | 2019-07-11 | 旭化成株式会社 | Method for producing 1,2-cyclohexanediol |
-
1990
- 1990-06-07 JP JP14904890A patent/JPH0441449A/en active Pending
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0645363A4 (en) * | 1993-04-09 | 1995-11-02 | Asahi Chemical Ind | Process for producing adipic acid. |
| US7385096B2 (en) | 2002-01-24 | 2008-06-10 | Japan Science And Technology Agency | Process for producing 1,2-diol |
| US8889922B2 (en) | 2011-12-30 | 2014-11-18 | E I Du Pont De Nemours And Company | Process for preparing 1, 6-hexanediol |
| WO2013101968A1 (en) * | 2011-12-30 | 2013-07-04 | E. I. Du Pont De Nemours And Company | Process for the production of hexanediols |
| US8981130B2 (en) | 2011-12-30 | 2015-03-17 | E I Du Pont De Nemours And Company | Process for the production of hexanediols |
| US8889912B2 (en) | 2011-12-30 | 2014-11-18 | E I Du Pont De Nemours And Company | Process for preparing 1,6-hexanediol |
| US8865940B2 (en) | 2011-12-30 | 2014-10-21 | E I Du Pont De Nemours And Company | Process for preparing 1,6-hexanediol |
| US8884036B2 (en) | 2011-12-30 | 2014-11-11 | E I Du Pont De Nemours And Company | Production of hydroxymethylfurfural from levoglucosenone |
| US8884035B2 (en) | 2011-12-30 | 2014-11-11 | E I Du Pont De Nemours And Company | Production of tetrahydrofuran-2, 5-dimethanol from isosorbide |
| US8846984B2 (en) | 2012-04-27 | 2014-09-30 | E I Du Pont De Nemours And Company | Production of α,ω-diols |
| US8859826B2 (en) | 2012-04-27 | 2014-10-14 | E I Du Pont De Nemours And Company | Production of alpha, omega-diols |
| US8846985B2 (en) | 2012-04-27 | 2014-09-30 | E I Du Pont De Nemours And Company | Production of alpha, omega-diols |
| US9018423B2 (en) | 2012-04-27 | 2015-04-28 | E I Du Pont De Nemours And Company | Production of alpha, omega-diols |
| US9181157B2 (en) | 2012-04-27 | 2015-11-10 | E I Du Pont De Nemours And Company | Production of alpha, omega-diols |
| US9670118B2 (en) | 2012-04-27 | 2017-06-06 | E I Du Pont De Nemours And Company | Production of alpha, omega-diols |
| JP2019112368A (en) * | 2017-12-26 | 2019-07-11 | 旭化成株式会社 | Method for producing 1,2-cyclohexanediol |
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