JPS63188642A - Production of 3,3,5-trimethylcyclohexanone - Google Patents
Production of 3,3,5-trimethylcyclohexanoneInfo
- Publication number
- JPS63188642A JPS63188642A JP62020697A JP2069787A JPS63188642A JP S63188642 A JPS63188642 A JP S63188642A JP 62020697 A JP62020697 A JP 62020697A JP 2069787 A JP2069787 A JP 2069787A JP S63188642 A JPS63188642 A JP S63188642A
- Authority
- JP
- Japan
- Prior art keywords
- isophorone
- trimethylcyclohexanone
- reaction
- catalyst
- trans
- 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
- POSWICCRDBKBMH-UHFFFAOYSA-N 3,3,5-trimethylcyclohexan-1-one Chemical compound CC1CC(=O)CC(C)(C)C1 POSWICCRDBKBMH-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims abstract description 48
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000010531 catalytic reduction reaction Methods 0.000 claims abstract description 3
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 11
- 239000007868 Raney catalyst Substances 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 13
- BRRVXFOKWJKTGG-YUMQZZPRSA-N (1s,5r)-3,3,5-trimethylcyclohexan-1-ol Chemical compound C[C@H]1C[C@H](O)CC(C)(C)C1 BRRVXFOKWJKTGG-YUMQZZPRSA-N 0.000 abstract description 7
- 239000000203 mixture Substances 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 5
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 229920003002 synthetic resin Polymers 0.000 abstract description 3
- 239000000057 synthetic resin Substances 0.000 abstract description 3
- 229920001971 elastomer Polymers 0.000 abstract description 2
- 239000000806 elastomer Substances 0.000 abstract description 2
- 239000004922 lacquer Substances 0.000 abstract description 2
- 229920006337 unsaturated polyester resin Polymers 0.000 abstract description 2
- 239000002966 varnish Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- 238000001816 cooling Methods 0.000 abstract 2
- 238000013329 compounding Methods 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000004073 vulcanization Methods 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 17
- 238000009835 boiling Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- OITMBHSFQBJCFN-UHFFFAOYSA-N 2,5,5-trimethylcyclohexan-1-one Chemical compound CC1CCC(C)(C)CC1=O OITMBHSFQBJCFN-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- BRRVXFOKWJKTGG-UHFFFAOYSA-N 3,3,5-trimethylcyclohexanol Chemical compound CC1CC(O)CC(C)(C)C1 BRRVXFOKWJKTGG-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- BRRVXFOKWJKTGG-SFYZADRCSA-N (1s,5s)-3,3,5-trimethylcyclohexan-1-ol Chemical compound C[C@@H]1C[C@H](O)CC(C)(C)C1 BRRVXFOKWJKTGG-SFYZADRCSA-N 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- NCPHGZWGGANCAY-UHFFFAOYSA-N methane;ruthenium Chemical compound C.[Ru] NCPHGZWGGANCAY-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- UENOQWSWMYJKIW-UHFFFAOYSA-N 1,2,2-trimethylcyclohexan-1-ol Chemical compound CC1(C)CCCCC1(C)O UENOQWSWMYJKIW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- -1 inholon Chemical compound 0.000 description 1
- 239000012194 insect media Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- 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、３．３．５−トリメチルシクロヘキサノンの
製造方法に係る。DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to a method for producing 3.3.5-trimethylcyclohexanone.
さらに詳しくは、イ、ソホロンをラネーニッケル触媒存
在下、水素ガス加圧下にて部分水添することによって、
従来技術に比べ廉価で高純度の３゜３．５−トリメチル
シクロヘキサノンを製造する方法に係る。More specifically, by partially hydrogenating sophorone in the presence of a Raney nickel catalyst and under pressure of hydrogen gas,
The present invention relates to a method for producing 3°3.5-trimethylcyclohexanone at a lower price and with higher purity than conventional techniques.
３．３．５−トリメチルシクロヘキサノンは、ラッカー
、ワニス等の被覆、仕上げ材製造に必要な合成樹脂組成
物を配合する為の溶剤として用いられている。3.3.5-Trimethylcyclohexanone is used as a solvent for blending synthetic resin compositions necessary for coatings such as lacquers and varnishes, and for producing finishing materials.
これは、３．３．５−トリメチルシクロヘキサノンが高
沸点であること、ゲル化することなしに、ビニル樹脂等
の合成樹脂を高含有量で溶屏する能力をもつこと、貯蔵
安定性に優れていること、などの理由によるものである
。This is because 3.3.5-trimethylcyclohexanone has a high boiling point, has the ability to dissolve synthetic resins such as vinyl resin in high content without gelation, and has excellent storage stability. This is due to reasons such as being present.
また、一方、不飽和ポリエステル圏脂用の硬化用触媒、
エラストマーの加硫剤等の用途にも使用され、工業的に
有用な物質である。In addition, on the other hand, a curing catalyst for unsaturated polyester resin,
It is also used as a vulcanizing agent for elastomers, and is an industrially useful substance.
（従来技術）
および
（発明が解決しようとする問題点）
イソホロンから３．３．５−トリメチルシクロヘキサノ
ンを製造する方法は、古くより周知の接触水添法がある
。(Prior Art) and (Problems to be Solved by the Invention) As a method for producing 3.3.5-trimethylcyclohexanone from isophorone, there is a catalytic hydrogenation method which has been well known for a long time.
かくして、米国特許２，２６４．６２５号にはイソホロ
ンの接触水添法が２滅されているが、かかる反応におい
ては充分な注意が必要である。Thus, although US Pat. No. 2,264.625 discloses a method for catalytic hydrogenation of isophorone, great care must be taken in such a reaction.
何故ならば過度に水添するとカルボニル基の水添が起き
アルコールであるシス−及びトランス−３，３，５−ト
リメチルシクロヘキサノールが副生じてしまうし、又、
水添が不充分であると天辺の未反応イソホロンを残す結
果になるからである。This is because excessive hydrogenation causes hydrogenation of the carbonyl group, resulting in the production of cis- and trans-3,3,5-trimethylcyclohexanol, which are alcohols, and also,
This is because if hydrogenation is insufficient, unreacted isophorone will remain at the top.
これら二通りの場合は、何れも望ましくはない。Neither of these two cases is desirable.
何故ならば、第一にアルコールまで過度に水添すると３
．３．５−トリメチルシクロヘキサノンから分別するの
に極めて困難なトランス−３，３゜５−トリメチルシク
ロヘキトルを生成するからである。Firstly, if alcohol is excessively hydrogenated, 3
．． This is because trans-3,3°5-trimethylcyclohexitol, which is extremely difficult to separate from 3,5-trimethylcyclohexanone, is produced.
即ち、３．３．５−トリメチルシクロヘキサノンの沸点
は１８９℃でありトランス３，３．５−メチルシクロヘ
キサノールの沸点は１９０℃である。第２に未反応イソ
ホロンを大暑に残す結果になる不充分な水添は、イソホ
ロンの回収リサイクル量が増加し、製造設備も複雑にな
り、経済的な方法ではない。That is, the boiling point of 3,3,5-trimethylcyclohexanone is 189°C, and the boiling point of trans-3,3,5-methylcyclohexanol is 190°C. Second, insufficient hydrogenation, which results in leaving unreacted isophorone in the heat, increases the amount of isophorone recovered and recycled, and the manufacturing equipment becomes complicated, which is not an economical method.
バッチ式方法によって３．３．５−）−リメチルシクロ
ヘキサノンを′！Ａ造する方法が米国特許２゜５６０．
３６１号にポされている。3.3.5-)-limethylcyclohexanone'! by a batch process. The method for making A is covered by U.S. Patent No. 2゜560.
It is posted in issue 361.
この特許では、イソホロンと３．３．５−トリメチルシ
クロヘキサノールの等モル混合物を接蝕水添舖媒の存在
下でトランス−水添反応を行なわしめ目的とする３、３
．５−トリメチルシクロヘキサノンを得るものであるが
、反応は遅く僅か７４％の変換を達成するのに１２時間
らかかる。In this patent, an equimolar mixture of isophorone and 3,3,5-trimethylcyclohexanol is subjected to a trans-hydrogenation reaction in the presence of a corrosive hydrogenation solvent.
．． Although 5-trimethylcyclohexanone is obtained, the reaction is slow and takes up to 12 hours to achieve only 74% conversion.
しかも、一方の原料である３、３．５−トリメチルシク
ロヘキサノールを予めイソホロンの水添によって製造す
ることが必要であり、且つ触媒ラネーニッケルを１０重
量％と天場に使用しており、全く実際的な方法とは言い
難い。Moreover, 3,3.5-trimethylcyclohexanol, one of the raw materials, must be prepared in advance by hydrogenating isophorone, and 10% by weight of Raney nickel is used as a catalyst, which is completely impractical. It's hard to say that it's a good method.
また、イソホロンから３．３．５−トリシクロヘキサノ
ンをＷＡ造する場合の接散ｊス元融媒としてルテニウム
カーボンを用いることにより、３，３゜５−トリメチル
シクロヘキサノンが選択率良りサツ造できることは周知
である。Furthermore, by using ruthenium carbon as a dispersion source melting medium in the WA production of 3,3,5-tricyclohexanone from isophorone, 3,3°5-trimethylcyclohexanone can be produced with good selectivity. It is well known.
しかしながら、触媒であるルテニウムカーボンは、非常
に高＋１１［ｉであり、ルアニウムカーボン触媒を用い
て、イソホロンから３．３．５−トリメチルシクロヘキ
サノンを製造する方法は、決して経済的な方法ではない
。However, the catalyst ruthenium carbon has a very high +11[i, and the method of producing 3,3,5-trimethylcyclohexanone from isophorone using a ruanium carbon catalyst is by no means an economical method.
そこで、゛本発明者らは、これらの問題を解決し、優れ
た３、３．５−トリメチルシクロヘキサノンの製造法を
検討した結果遂に本発明を成すに至った。Therefore, the present inventors solved these problems and investigated an excellent method for producing 3,3,5-trimethylcyclohexanone, and as a result, they finally accomplished the present invention.
（発明の構成）
即ち、本発明は
［イソホロンを部分水添して、３，３．５−トリメチル
シクロヘキサノンを製造する方法において、接触還元触
媒として、ラネーニッケルを用い、イソホロンを水素ガ
スの加圧下２５℃以下の反応温度で反応させることを特
徴とする３、３．５−トリメチルシクロヘキサノンのｔ
Ｊ３ｉ４方法」である。(Structure of the Invention) That is, the present invention provides a method for producing 3,3,5-trimethylcyclohexanone by partially hydrogenating isophorone, using Raney nickel as a catalytic reduction catalyst, t of 3,3,5-trimethylcyclohexanone, characterized in that the reaction is carried out at a reaction temperature of ℃ or less.
J3i4 method”.
以下に本発明の詳細な説明する。The present invention will be explained in detail below.
第１図は、イソホロンから３．３．５−トリシクロヘキ
サノンを？Ａ造する場合の工程フローシートである。Figure 1 shows 3.3.5-tricyclohexanone from isophorone? This is a process flow sheet for building A.
第１図に於いて、導管１からイソホロンを、導管２から
溶剤であるイソプロパツールを含むラネーニッケル触媒
を、それぞれ反応器４に導入し、導管３から水素ガスを
導入して、２５℃以■に冷ＵＪＬながらイソホロンの水
添反応を行う。In FIG. 1, isophorone is introduced through conduit 1, and Raney nickel catalyst containing isopropanol as a solvent is introduced through conduit 2 into reactor 4, hydrogen gas is introduced through conduit 3, and the temperature rises above 25°C. Hydrogenation reaction of isophorone is carried out under cold UJL.
反応系におけるイソホロンの水添反応は次式で表わされ
る。The hydrogenation reaction of isophorone in the reaction system is expressed by the following formula.
イソよ。ン ３．３．５−トリメチ
ルシクロヘキサノン
３、３．５−トリメチ
ルシクロヘキサ
ノール
この反応は、ラネーニッケル融ＦＸを用いる場合、反応
温度が高ければ、インホロンが水添されて生成する、ト
ランス−３，３，５−トリメチルシクロヘキサノールの
生成けが増加し、目的物である３、３．５−トリメチル
シクロへキナノンとトランス−３，３，５−トリメチル
シクロへキナノールの沸点が近いため、蒸留にて分別す
ることが極めて困鼎となる。Iso. 3.3.5-Trimethylcyclohexanone 3,3.5-Trimethylcyclohexanol When using Raney nickel melt FX, if the reaction temperature is high, inphorone is hydrogenated and trans-3,3, The production of 5-trimethylcyclohexanol increases, and the target products, 3,3,5-trimethylcyclohequinanone and trans-3,3,5-trimethylcyclohequinanol, have similar boiling points, so they must be separated by distillation. becomes extremely difficult.
しかしながら、反応）晶度を２５℃以下になるように冷
却し、イソホロンを水添すれば、トランス−３，３，５
−トリメチルシクロヘキサノールの生成塁は氏めて少Ｇ
となる。However, if the reaction) crystallinity is cooled to below 25°C and isophorone is hydrogenated, trans-3,3,5
- The generation base of trimethylcyclohexanol should be cooled down to a low G.
becomes.
次に、３，３．５−トリメナルシクロヘキサノン、トラ
ンス−３，３，５−トリメチルシクロヘキサノール、イ
ンホロン、ラネーニッケルｒ媒、イソプロピルアルコー
ル等を含んだ水添液を、５の触媒分迩器により、ラネー
ニッケル触媒と３．。Next, a hydrogenation solution containing 3,3,5-trimenalcyclohexanone, trans-3,3,5-trimethylcyclohexanol, inholon, Raney nickel medium, isopropyl alcohol, etc. is passed through a catalyst distributor in 5. Raney nickel catalyst and 3. .
５−トリメチルシクロへキナノン、トランス−３゜３．
５−トリメチルシクロヘキサノン、イソホロン、イソプ
ロピルアルコール等をｇんだ液に分遣する。5-trimethylcyclohequinanone, trans-3゜3.
Dispense 5-trimethylcyclohexanone, isophorone, isopropyl alcohol, etc. into the grated liquid.
３．３．５−ｔ−ルメチルシクロヘキサノン、トランス
−３，３，５−トリメチルシクロヘキサノール、イソホ
ロン、インプロピルアルコール等を含む液は′Ｍ製塔６
で低沸成分、高沸成分を除去し、純度の高い３．３．５
−トリメチルシクロヘキサノンを得る。3.3.The liquid containing 5-tert-methylcyclohexanone, trans-3,3,5-trimethylcyclohexanol, isophorone, inpropyl alcohol, etc.
3.3.5 with high purity by removing low boiling components and high boiling components.
-trimethylcyclohexanone is obtained.
以下に本発明の効果を実施例、比較列を用いて説明する
。The effects of the present invention will be explained below using examples and comparison columns.
実施例
反応器にイソホロン９０’ＯＮ、イソプロピルアルコー
ル１００ｐ１ラネーニツケル、）虫媒４０Ｋｇを仕込み
、反応温度１６℃に保ちながら水素ガスを１６９Ｎ立米
／１−１の速度で仕込み、ポンプでＶ＠環し、水添反応
を行った。Example A reactor was charged with 90'ON of isophorone, 100p1 of isopropyl alcohol, and 40kg of insect medium, and while maintaining the reaction temperature at 16°C, hydrogen gas was charged at a rate of 169N m3/1-1. A hydrogenation reaction was performed.
反応圧力４〜９に’ｉ／ｃ：ｉＧである。The reaction pressure is 4-9'i/c:iG.
反応時間約３＠間後の反応：層液より、ラネーニッケル
触媒を分列した反応ｍ液１成はガスクロ分析によると３
．３．５−トリメチルシクロへキサノン８０．８６ｗｔ
％、トランス−３，３，５−トリメチルシクロヘキサノ
ール２．２８ｗｔ％。Reaction after about 3 reaction times: According to gas chromatography, the reaction liquid 1, in which the Raney nickel catalyst was separated from the layer liquid, was 3.
．． 3.5-trimethylcyclohexanone 80.86wt
%, trans-3,3,5-trimethylcyclohexanol 2.28 wt%.
シス−３，３，５−トリメチルシクロヘキサノール０．
４９ｗｔ％、イソホ［：Ｉン９．３４ｗｔ％。Cis-3,3,5-trimethylcyclohexanol 0.
49 wt%, Isopho[:In 9.34 wt%.
イソプロピルアルコール６．５２Ｗｔ’ｊ１０．その他
０．５１ｗｔ％であった。Isopropyl alcohol 6.52Wt'j10. Others were 0.51 wt%.
この反応ｍ液のＭ裂塔にて脱低沸及び説店沸を行って得
た製品の組成は、３．３．５−トリメチルシクロヘキサ
ノン９９．６９１／Ｖｔ％、トランスー３．３．５−ト
リメチルシクロヘキサノール０゜２６ｗｔ％、その他０
．０５ｗｔ％である。The composition of the product obtained by removing low boiling temperature and high temperature boiling of this reaction liquid in the M column is 3.3.5-trimethylcyclohexanone 99.691/Vt%, trans-3.3.5-trimethyl Cyclohexanol 0゜26wt%, other 0
．． 05wt%.
比咬例
反応器にイソホロン９００！Ｊ、インプロピルアルコー
ル１００ｆＪ、ラネーニッケル触媒４０に９を仕込み、
反応温度を３８℃に保ちながら、水素ガスを１６３Ｎ立
米／Ｈの速度で仕込み、ポンプで循環し、水添反応を行
った。Isophorone 900 for the ratio bite reactor! J, inpropyl alcohol 100 fJ, Raney nickel catalyst 40 charged with 9,
While maintaining the reaction temperature at 38°C, hydrogen gas was charged at a rate of 163N cubic meters/H and circulated with a pump to carry out a hydrogenation reaction.
反応圧力は４〜９にぴ／ｒｒｔＧである。The reaction pressure is 4 to 9 pi/rrtG.
反応時間約３時間後の反応：層液よりラネーニッケル触
媒を分列した。Reaction after about 3 hours of reaction time: Raney nickel catalyst was separated from the layer liquid.
反応ｍ液の組成は、ガスクロ分析によると、３゜３．５
−トリメチルシクロへキサノン８１．５４Ｗ ｉ ’％
、 トランス−３，３，５−トリメチルシクロヘキ
サノール４．１５ｗｔ％、シス−３，３゜５−トリメチ
ルシクロヘキサノール０．７５ｗｔ％、イソホロン９．
２４ｗｔ％、イソプロピルアルコール４．１８ｗｔ％、
その他０．１４Ｗｔ’％であった。According to gas chromatography, the composition of reaction solution M was 3°3.5.
-Trimethylcyclohexanone 81.54W i'%
, trans-3,3,5-trimethylcyclohexanol 4.15wt%, cis-3,3°5-trimethylcyclohexanol 0.75wt%, isophorone 9.
24wt%, isopropyl alcohol 4.18wt%,
Others were 0.14 Wt'%.
この反応、ｉ１１液を精製塔にて脱低沸及び脱高沸を１
ｑって１ｑた製品の組成は、３，３．５−トリメデルシ
クロへキサノン９６．５４Ｗ−ｔ：％、トランスー３
＋ ３ ＋ ５−トリメブールシクロへキナノール３゜
４２ｗｔ％、そのｆｔ！！０．０４ｗｔ％である。In this reaction, the i11 liquid is removed from low boiling point and high boiling point by 1 in a purification column.
The composition of the product, where q is 1q, is 3,3.5-trimedelcyclohexanone 96.54W-t:%, trans-3
+ 3 + 5-trimebulccyclohequinanol 3°42wt%, its ft! ! It is 0.04wt%.
第１図は、本発明の方法を通用する反応装コ、′Ｍ製の
ための蒸留塔などのフローシートであり、４が温度制御
ができろ水添反応器である。FIG. 1 is a flow sheet of a reaction vessel, a distillation column for producing M, etc., which can be used in the method of the present invention, and 4 is a hydrogenation reactor whose temperature can be controlled.
Claims (1)
クロヘキサノンを製造する方法において、接触還元触媒
としてラネーニッケルを用い、イソホロンを水素ガスの
加圧下、２５℃以下反応温度で反応させることを特徴と
する３，３，５−トリメチルシクロヘキサノンの製造方
法。A method for producing 3,3,5-trimethylcyclohexanone by partially hydrogenating isophorone, characterized by using Raney nickel as a catalytic reduction catalyst and reacting isophorone under pressure of hydrogen gas at a reaction temperature of 25°C or less. A method for producing 3,3,5-trimethylcyclohexanone.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62020697A JPH0749385B2 (en) | 1987-01-31 | 1987-01-31 | Method for producing 3,3,5-trimethylcyclohexanone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62020697A JPH0749385B2 (en) | 1987-01-31 | 1987-01-31 | Method for producing 3,3,5-trimethylcyclohexanone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63188642A true JPS63188642A (en) | 1988-08-04 |
| JPH0749385B2 JPH0749385B2 (en) | 1995-05-31 |
Family
ID=12034345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62020697A Expired - Lifetime JPH0749385B2 (en) | 1987-01-31 | 1987-01-31 | Method for producing 3,3,5-trimethylcyclohexanone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0749385B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5728891A (en) * | 1990-07-08 | 1998-03-17 | Huels Aktiengesellschaft | Process for the preparation of 3,3,5-trimethylcyclohexanone |
| CN105061176A (en) * | 2015-07-22 | 2015-11-18 | 黄河三角洲京博化工研究院有限公司 | Fixed-bed synthetic method for 3,3,5-trimethylcyclohexanone |
-
1987
- 1987-01-31 JP JP62020697A patent/JPH0749385B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5728891A (en) * | 1990-07-08 | 1998-03-17 | Huels Aktiengesellschaft | Process for the preparation of 3,3,5-trimethylcyclohexanone |
| CN105061176A (en) * | 2015-07-22 | 2015-11-18 | 黄河三角洲京博化工研究院有限公司 | Fixed-bed synthetic method for 3,3,5-trimethylcyclohexanone |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0749385B2 (en) | 1995-05-31 |
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