JPS62164656A - Production of cyanoisophorone - Google Patents
Production of cyanoisophoroneInfo
- Publication number
- JPS62164656A JPS62164656A JP435786A JP435786A JPS62164656A JP S62164656 A JPS62164656 A JP S62164656A JP 435786 A JP435786 A JP 435786A JP 435786 A JP435786 A JP 435786A JP S62164656 A JPS62164656 A JP S62164656A
- Authority
- JP
- Japan
- Prior art keywords
- cyanoisophorone
- acetal
- solvent
- acid catalyst
- reaction
- 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.)
- Granted
Links
- NSGLXUMORGEZEF-UHFFFAOYSA-N 2,4,4-trimethyl-6-oxocyclohexene-1-carbonitrile Chemical compound CC1=C(C#N)C(=O)CC(C)(C)C1 NSGLXUMORGEZEF-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 21
- -1 polymethylene Polymers 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 239000003377 acid catalyst Substances 0.000 claims abstract description 7
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims abstract 5
- 239000000126 substance Substances 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000002904 solvent Substances 0.000 abstract description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 239000004593 Epoxy Substances 0.000 abstract description 2
- 238000009835 boiling Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 150000001768 cations Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000011527 polyurethane coating Substances 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000005977 Ethylene Substances 0.000 description 8
- 150000001241 acetals Chemical class 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JJDFVIDVSCYKDS-UHFFFAOYSA-N 1,3,3-trimethyl-5-oxocyclohexane-1-carbonitrile Chemical compound CC1(C)CC(=O)CC(C)(C#N)C1 JJDFVIDVSCYKDS-UHFFFAOYSA-N 0.000 description 1
- ROSFUFIOLRQOON-UHFFFAOYSA-N 2,4-Dimethyl-1,3-dioxolane Chemical compound CC1COC(C)O1 ROSFUFIOLRQOON-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012045 crude solution Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
く産業上の利用分野〉
本発明はシアノイソホロンのアセタールを畝触媒により
加水分解することで、シアノインホロンを製造する方法
に関するものである。DETAILED DESCRIPTION OF THE INVENTION Industrial Application Field The present invention relates to a method for producing cyanoinphorone by hydrolyzing the acetal of cyanoisophorone using a ridge catalyst.
シアノイソホロン（３−シアノ−３，５，５−トリメチ
ルシクロヘキサノンとも言う。）は、さらに水素添加と
アミン化してエポキシ硬化剤、ポリウレタン塗料等の原
料として有用な化合物である。Cyanoisophorone (also referred to as 3-cyano-3,5,5-trimethylcyclohexanone) is a compound that is further hydrogenated and aminated and is useful as a raw material for epoxy curing agents, polyurethane paints, and the like.
〈従来技術〉
シアノイソホロンの合成は既に知られており、例えば、
特開昭４０−７４８６、特開昭５６−７１０５７、特開
昭５７−１１６０３８などに記載された方法によって合
成することができる。<Prior art> Synthesis of cyanoisophorone is already known, for example,
It can be synthesized by methods described in JP-A-40-7486, JP-A-56-71057, JP-A-57-116038, and the like.
これら既知合成法は、いずれもイソホロンと青酸化合物
との付加反応によってシアノイソホロンを得るものであ
る。All of these known synthetic methods obtain cyanoisophorone through an addition reaction between isophorone and a cyanide compound.
〈発明が解決しようとする問題点〉
ところで、これ等を追試検討するうち、特開昭５７−１
１６０３８のように、溶媒としてエチレングリコール等
のグリコール系溶媒を使用するとき、実際にはシアノイ
ソホロンの生成とともに、シアノイソホロンのアセター
ルの副生が見られた。<Problems to be solved by the invention> By the way, while conducting additional examinations on these issues, we discovered that
When a glycol solvent such as ethylene glycol was used as a solvent as in 16038, it was actually observed that cyanoisophorone was produced and acetal of cyanoisophorone was produced as a by-product.
この現象は、シアノイソホロンの反応粗液の後処理工程
において共存するエチレングリコール等のグリコール類
が、中和剤として使用される酸の触媒作用によってアセ
タール化ヲスる為と考えられる。シアノイソホロンのア
セタールの副生はインホロンの使用率を悪化させ、又、
不純物としてシアノイソホロン中に存在するが故に得ら
れたシアノイソホロンの用途を制限し、精製の為の工程
が必要となる。This phenomenon is thought to be because glycols such as ethylene glycol, which coexist in the post-treatment process of the reaction crude solution of cyanoisophorone, are acetalized by the catalytic action of the acid used as a neutralizing agent. The acetal by-product of cyanoisophorone worsens the usage rate of inphorone, and
The presence of impurities in cyanoisophorone limits the uses of the obtained cyanoisophorone and requires a purification step.
そこで本発明者は、シアノインホロンのアセタールをシ
アノイソホロンへ変換する方法で、しかもシアノイソホ
ロンとシアノイソホロンのアセタールとの混合物を分離
することなく、−挙に高純度のシアノイソホロンにする
ことの可能な方法につき鋭意研究をし、結果として本発
明を完成するに到った。Therefore, the present inventor has developed a method for converting the acetal of cyanoinphorone to cyanoisophorone, and without separating the mixture of cyanoisophorone and cyanoisophorone acetal, which makes it possible to obtain highly pure cyanoisophorone. As a result, we have completed the present invention.
〈問題点を解決するための手段〉
即ち、本発明は下記一般式で表わされるシアノイソホロ
ンのアセタール及びこれを含有する混合物を酸触媒で加
水分解せしめることを特徴とするシアノイソホロンの製
造法である。<Means for solving the problems> That is, the present invention is a method for producing cyanoisophorone, which is characterized by hydrolyzing an acetal of cyanoisophorone represented by the following general formula and a mixture containing the same using an acid catalyst. .
式中、ｒｔｌｒｔは炭素数か１〜３個を有し、且つ、同
一の直鎖あるいは分校の低級アルキル基、又は両者で環
を形成する直鎖あるいは分校のポリメチレン基を示す。In the formula, rtlrt has 1 to 3 carbon atoms and represents the same linear or branched lower alkyl group, or a linear or branched polymethylene group in which both of them form a ring.
次に、さらに詳しく本発明を説明する。Next, the present invention will be explained in more detail.
本発明における出発原料であるシアノイソホロンのアセ
タールとしては、前記一般式で表わされ、対応するケト
ンとアルコール２分子又は対応するケトンとジオールを
酸触媒の存在下で脱水縮合させることにより容易に入手
可能である。The acetal of cyanoisophorone, which is the starting material in the present invention, is represented by the above general formula and can be easily obtained by dehydration condensation of the corresponding ketone and two molecules of alcohol or the corresponding ketone and diol in the presence of an acid catalyst. It is possible.
具体的にはジメチルアセタール、ジエチルアセタール、
エチレンアセタール、プロピレンアセタール、メチルエ
チレンアセタール等の非環状並びに環状アセタールか挙
げられる。Specifically, dimethyl acetal, diethyl acetal,
Examples include acyclic and cyclic acetals such as ethylene acetal, propylene acetal, and methylethylene acetal.
又、シアノインホロンのアセタールを含有する混合物と
しては、グリコール系溶媒を使用したインホロンと青酸
からのシアノイソホロンの合成（例えば、特開昭５７−
１１６０３８等）から得られる反応混合物が対照となる
。In addition, as a mixture containing an acetal of cyanoinphorone, synthesis of cyanoisophorone from inphorone and hydrocyanic acid using a glycol solvent (for example, Japanese Patent Application Laid-Open No. 1983-1989)
116038 etc.) serves as a control.
酸触媒としては、塩酸、硫酸、リン酸等の鉱酸；カチオ
ン型イオン交換樹脂；又はパラトルエンスルホン酸等の
有機酸が挙げられ、その使用量は触媒量程度、通常出発
原料に対し、約０．１〜１．０％の範囲で用いられる。Examples of acid catalysts include mineral acids such as hydrochloric acid, sulfuric acid, and phosphoric acid; cationic ion exchange resins; and organic acids such as para-toluenesulfonic acid. It is used in a range of 0.1 to 1.0%.
本発明の方法を実施するに当っては、通常出発原料及び
溶媒を反応温度に維持し、これに酸触媒を投入し、反応
させて目的物を取得する回分式操作によって実施される
。The method of the present invention is usually carried out by a batch operation in which the starting materials and the solvent are maintained at the reaction temperature, an acid catalyst is added thereto, and the desired product is obtained by the reaction.
反応溶媒はメタノール、エタノール等のアルコール系溶
媒（５重量％以下の含水でも可。）が選ばれ、その使用
量は通常出発原料に対し、約２〜２０倍の範囲で用いら
れる。反応温度は室温から溶媒の沸点まで任意に実施で
きる。As the reaction solvent, an alcoholic solvent such as methanol or ethanol (which may contain water of 5% by weight or less) is selected, and the amount used is usually about 2 to 20 times the amount of the starting material. The reaction temperature can be arbitrarily set from room temperature to the boiling point of the solvent.
反応終了後のシアノイソホロンの単離精製は、溶媒を留
去し、シアノイソホロンを蒸溜することによって容易に
行なうことが出来、イオン交換樹脂触媒の場合は、ｒ過
後溶媒の留去のみで充分次工穆の使用に供せられるシア
ノイソホロンが得られる。Isolation and purification of cyanoisophorone after the completion of the reaction can be easily carried out by distilling off the solvent and then distilling the cyanoisophorone. In the case of an ion exchange resin catalyst, simply distilling off the solvent after 3 hours is sufficient for the next step. Cyanoisophorone is obtained which can be used in engineering.
〈実施例〉 以下に実施例を挙げて本発明を具体的に説明する。<Example> The present invention will be specifically described below with reference to Examples.
実施例１゜
攪拌機、冷却器、温度計及び滴下漏斗を備えた反応装置
に、シアノインホロンのエチレンアセタール３０ｐを１
％含水メタノール２００１１１１に溶解し、濃硫酸２滴
を添加して室温で攪拌した。１２時間後の反応粗液のガ
スクロマトグラフィー分析によりシアノインホロンのエ
チレンアセタールの完全消失（転化率１００．０％）と
シアノイソホロン及びエチレングリコールの生成が確認
された。その他の副生物は確認されなかった。Example 1 Into a reaction apparatus equipped with a stirrer, a condenser, a thermometer, and a dropping funnel, 30 p of ethylene acetal of cyanoinphorone was added.
% water-containing methanol 2001111, added 2 drops of concentrated sulfuric acid, and stirred at room temperature. Gas chromatography analysis of the reaction crude liquid after 12 hours confirmed complete disappearance of ethylene acetal of cyanoinphorone (conversion rate 100.0%) and generation of cyanoisophorone and ethylene glycol. No other by-products were confirmed.
得られた反応粗液はロータリーエバポレーターを用いて
減圧下（５０＋ｎｍＨｇ、湯浴温度４０℃）で溶媒を留
去した後、残渣として得られた白色結晶２４ｇを、１０
段の多孔板塔を用いて減圧下（１ｏｍｍＨｇ）蒸溜する
ことにより部分（１２８〜１３０°Ｃ）のシアノイソホ
ロン２２Ｉ（収率９３゜２％）を得た。After distilling off the solvent from the obtained reaction crude liquid under reduced pressure (50+nmHg, water bath temperature 40°C) using a rotary evaporator, 24 g of white crystals obtained as a residue were
Partial (128-130°C) cyanoisophorone 22I (yield 93°2%) was obtained by distillation under reduced pressure (1 ommHg) using a multi-stage perforated plate column.
実施例２゜
シアノイソホロンのエチレンアセタール３０Ｉを１％含
水エタノール２００ｍ１に溶解し、カチオン交換樹脂（
ダイアイオン 、三菱化成■製） １．０ ｇを加えて
室温で攪拌した。２４時間後、反応粗液中のシアノイソ
ホロンのエチレンアセタールの完全消失とシアノイソホ
ロンの生成が確認された。Example 2 Ethylene acetal 30I of cyanoisophorone was dissolved in 200 ml of 1% aqueous ethanol, and a cation exchange resin (
1.0 g of Diaion (manufactured by Mitsubishi Kasei Corporation) was added thereto, and the mixture was stirred at room temperature. After 24 hours, complete disappearance of ethylene acetal of cyanoisophorone in the reaction crude liquid and generation of cyanoisophorone were confirmed.
実施例３゜
反応温度が加熱還流下である以外、は、実施例１と同様
にして反応を行なったところ、３〜４時間後、シアノイ
ソホロンのエチレンケタールの転化率は１００．０％で
あった。Example 3: The reaction was carried out in the same manner as in Example 1, except that the reaction temperature was heated to reflux. After 3 to 4 hours, the conversion rate of ethylene ketal from cyanoisophorone was 100.0%. Ta.
実施例４゜
出発原料がシアノイソホロンとシアノイソホロンのエチ
レンアセタールの混合物（９６：４）である以外は実施
例１と同様にして反応を行なったところ、１時間後反応
粗液中のシアノイソホロンのエチレンケタールは全て消
失し、シアノイソホロン及び加水分解によって生じたエ
チレングリコールの混合物に変化していることが確認さ
れた。Example 4 The reaction was carried out in the same manner as in Example 1 except that the starting material was a mixture of cyanoisophorone and ethylene acetal of cyanoisophorone (96:4). After 1 hour, the amount of cyanoisophorone in the crude reaction solution was It was confirmed that all of the ethylene ketal had disappeared and it had changed to a mixture of cyanoisophorone and ethylene glycol produced by hydrolysis.
Claims (1)
及びこれを含有する混合物を酸触媒で加水分解せしめる
ことを特徴とするシアノイソホロンの製造法 ▲数式、化学式、表等があります▼ 式中、Ｒ、Ｒ′は炭素数が１〜３個を有し、且つ、同一
の直鎖あるいは分枝の低級アルキル基又は両者で環を形
成する直鎖あるいは分枝のポリメチレン基を示す。[Claims] A method for producing cyanoisophorone, characterized by hydrolyzing an acetal of cyanoisophorone represented by the following general formula and a mixture containing the same with an acid catalyst ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Formula In the formula, R and R' each have 1 to 3 carbon atoms and represent the same straight-chain or branched lower alkyl group, or a straight-chain or branched polymethylene group in which both of them form a ring.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP435786A JPS62164656A (en) | 1986-01-14 | 1986-01-14 | Production of cyanoisophorone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP435786A JPS62164656A (en) | 1986-01-14 | 1986-01-14 | Production of cyanoisophorone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62164656A true JPS62164656A (en) | 1987-07-21 |
| JPH0584305B2 JPH0584305B2 (en) | 1993-12-01 |
Family
ID=11582140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP435786A Granted JPS62164656A (en) | 1986-01-14 | 1986-01-14 | Production of cyanoisophorone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62164656A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5179221A (en) * | 1991-03-05 | 1993-01-12 | Nippon Chemicals Co., Ltd. | Method for production of 3-cyano-3,5,5-trimethyl cyclohexanone |
| WO2012171830A1 (en) | 2011-06-17 | 2012-12-20 | Evonik Degussa Gmbh | Process for preparing 3-cyano-3,5,5-trimethylcyclohexanone |
| CN105985260A (en) * | 2015-03-19 | 2016-10-05 | 赢创德固赛有限公司 | Process for removing cations from an isophoronenitrile product mixture |
-
1986
- 1986-01-14 JP JP435786A patent/JPS62164656A/en active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5179221A (en) * | 1991-03-05 | 1993-01-12 | Nippon Chemicals Co., Ltd. | Method for production of 3-cyano-3,5,5-trimethyl cyclohexanone |
| WO2012171830A1 (en) | 2011-06-17 | 2012-12-20 | Evonik Degussa Gmbh | Process for preparing 3-cyano-3,5,5-trimethylcyclohexanone |
| DE102011077681A1 (en) | 2011-06-17 | 2012-12-20 | Evonik Degussa Gmbh | Process for the preparation of 3-cyano-3,5,5-trimethylcyclohexanone |
| CN105985260A (en) * | 2015-03-19 | 2016-10-05 | 赢创德固赛有限公司 | Process for removing cations from an isophoronenitrile product mixture |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0584305B2 (en) | 1993-12-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HU198437B (en) | Process for producing mono- or bis-carbonyl-compounds | |
| JPH06157378A (en) | Preparation of 1,3-propanediol | |
| US4181810A (en) | Process for the preparation of propane-1,3-diols, disubstituted in the 2-position | |
| JPS62164656A (en) | Production of cyanoisophorone | |
| JPS5935904B2 (en) | Method for producing new compounds | |
| JP2830210B2 (en) | Synthesis of α, β-unsaturated ketones | |
| US4231962A (en) | 3-Phenoxybenzylideneamines and 3-benzylbenzylideneamines | |
| US4003924A (en) | Process for preparing 1-amino anthraquinone | |
| RU2240301C2 (en) | Method for preparing fluorinated compound of benzenedimethanol | |
| JP3795970B2 (en) | Method for producing α, β-unsaturated aldehyde | |
| JPH0273033A (en) | Production of 4, 4-dimethyl-1-(p-chlorophenyl) pentane-3-one | |
| HU213374B (en) | Process for producing 4-amino-5-hexenoic acid | |
| JPH0717935A (en) | Process for producing 3-aminopropionitrile | |
| JPH0250101B2 (en) | ||
| JP2009513503A (en) | Method for producing cosmetic active ingredients | |
| JPS62126164A (en) | 4-alkoxy-2-oxo-pyrrolidine-1 acetic acid alkyl ester and manufacture | |
| JPH08109170A (en) | Method for producing hexahydropyridazine | |
| JPS63295562A (en) | Manufacture of 4-methylimidazole | |
| CN115160119A (en) | Method for preparing 4-methoxy-3-butene-2-ketone | |
| SU1286588A1 (en) | Method of producing iodohydrins | |
| CN119528959A (en) | A preparation method of 1-decyn-5-ol and its derivatives | |
| KR100625886B1 (en) | Method for Purifying L-Muscon or Di-Muscon Using Stereoselective Separation Method | |
| JPH0827072A (en) | Method for producing 2-methyl-1,2-propanediamine | |
| KR20040026964A (en) | Synthesis of cyclohexyl phenyl ketone from 1,3-butadiene and acrylic acid | |
| JPH0159266B2 (en) |