JPH02145570A - Production of 2,2,6,6-tetramethyl-4-oxopiperidine - Google Patents
Production of 2,2,6,6-tetramethyl-4-oxopiperidineInfo
- Publication number
- JPH02145570A JPH02145570A JP63300314A JP30031488A JPH02145570A JP H02145570 A JPH02145570 A JP H02145570A JP 63300314 A JP63300314 A JP 63300314A JP 30031488 A JP30031488 A JP 30031488A JP H02145570 A JPH02145570 A JP H02145570A
- Authority
- JP
- Japan
- Prior art keywords
- acetone
- ammonia
- tetramethyl
- catalyst
- oxopiperidine
- 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
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 title abstract description 17
- 238000004519 manufacturing process Methods 0.000 title description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 76
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 57
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 28
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- WWILHZQYNPQALT-UHFFFAOYSA-N 2-methyl-2-morpholin-4-ylpropanal Chemical compound O=CC(C)(C)N1CCOCC1 WWILHZQYNPQALT-UHFFFAOYSA-N 0.000 claims description 14
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 abstract description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 21
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 9
- 238000000034 method Methods 0.000 abstract description 8
- 235000019270 ammonium chloride Nutrition 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 4
- 238000005260 corrosion Methods 0.000 abstract description 3
- 230000007797 corrosion Effects 0.000 abstract description 3
- 150000004820 halides Chemical class 0.000 abstract description 3
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 abstract description 2
- 235000011130 ammonium sulphate Nutrition 0.000 abstract description 2
- 239000007844 bleaching agent Substances 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 abstract description 2
- 239000003381 stabilizer Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 7
- PIFBMJMXJMZZRG-UHFFFAOYSA-N 2,2,4,6,6-pentamethyl-1,5-dihydropyrimidine Chemical compound CC1=NC(C)(C)NC(C)(C)C1 PIFBMJMXJMZZRG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000007664 blowing Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 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
- Hydrogenated Pyridines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、アセトンおよび／またはアセトンの縮合物と
アンモニアとから２．２，６，６−テトラメチル−４−
オキソピペリジンを製造する方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention provides 2,2,6,6-tetramethyl-4-
The present invention relates to a method for producing oxopiperidine.
従来、２，２，６，６−テトラメチル−４−オキソピペ
リジン（別名トリアセトンアミン）の製造方法として、
アセトンとアンモニアを酸触媒の存在下で、５〜３５℃
の温度で反応させ、次にアセトンとアンモニアのモル比
が１．６：１以上になるように追加のアセトンを加え、
４０〜６０℃に加熱して反応を完結させる方法がある（
特公昭５９−２９５８９号）、この方法では、塩化アン
モニウム、硫酸などが好適な触媒であるとされているが
、このうち塩化アンモニウムには応力腐食性があるため
、反応器に耐ハライド性の材質を使用しなければならな
いという問題点がある。また、硫酸を触媒として使用し
た場合、反応系が強酸性となるため、アンモニアで中和
されるまでにアセトン、メタノールなどが消費されて損
失するという問題点がある。さらに、市販の硫酸アンモ
ニウムを用いた場合には、目的物である２、２，６，６
−テトラメチル−４−オキソピペリジンの収率が極めて
低いという欠点がある。Conventionally, as a method for producing 2,2,6,6-tetramethyl-4-oxopiperidine (also known as triacetonamine),
Acetone and ammonia in the presence of an acid catalyst at 5-35℃
React at a temperature of
There is a method to complete the reaction by heating to 40-60℃ (
(Japanese Patent Publication No. 59-29589), it is said that ammonium chloride, sulfuric acid, etc. are suitable catalysts for this method, but since ammonium chloride has stress corrosion properties, the reactor must be made of halide-resistant material. The problem is that you have to use . Furthermore, when sulfuric acid is used as a catalyst, the reaction system becomes strongly acidic, so there is a problem that acetone, methanol, etc. are consumed and lost before being neutralized with ammonia. Furthermore, when commercially available ammonium sulfate is used, the target product 2, 2, 6, 6
The drawback is that the yield of -tetramethyl-4-oxopiperidine is extremely low.
本発明の目的は、上記問題点を解決するため、応力腐食
性や原料の無駄な消費がなく、かつ高収率で２．２，６
．６−テトラメチル−４−オキソピペリジンを製造する
ことができる方法を提案することにある。The purpose of the present invention is to solve the above-mentioned problems by eliminating stress corrosion and wasteful consumption of raw materials, and producing 2.2,6
．． The object of the present invention is to propose a method by which 6-tetramethyl-4-oxopiperidine can be produced.
本発明は、アセトンおよび／またはアセトンの縮合物と
アンモニアとを反応させて２，２，６．６−テトラメチ
ル−４−オキシピペリジンを製造するにあたり、硫酸水
素アンモニウムを触媒として用いる２、２，６．６−テ
トラメチル−４−オキソピペリジンの製造方法である。The present invention uses ammonium hydrogen sulfate as a catalyst to produce 2,2,6,6-tetramethyl-4-oxypiperidine by reacting acetone and/or acetone condensate with ammonia. 6. A method for producing 6-tetramethyl-4-oxopiperidine.
本発明で使用するアセトンおよび／またはアセトンの縮
合物としては、たとえばアセトン、メシチルオキシド、
ジアセトンアルコール、ホロンなどを例示できる。これ
らは単独で使用してもよいし、２種以上を混合して使用
してもよい。Acetone and/or acetone condensates used in the present invention include, for example, acetone, mesityl oxide,
Examples include diacetone alcohol and holon. These may be used alone or in combination of two or more.
本発明において、反応の出発原料となるアセトンおよび
／またはアセトンの縮合物とアンモニアは、アセトン／
アンモニア（モル比）で２〜２０．好ましくは３〜７の
割合で使用するのが好ましい。In the present invention, acetone and/or acetone condensate and ammonia are used as starting materials for the reaction.
Ammonia (molar ratio) is 2 to 20. Preferably, it is used in a ratio of 3 to 7.
この場合アセトンの縮合物はアセトンに換算してモル比
を決める。In this case, the molar ratio of the acetone condensate is determined in terms of acetone.
本発明で使用する触媒は硫酸水素アンモニウム（ＮＨ４
ＩＳＯ，）であり、市販のものが使用できる。触媒の使
用量は、反応系全重量に対して０．５〜２０重量％、好
ましくは２〜１０重景％である。触媒は水溶液として用
いることもできるが、反応液中にそのまま添加して不均
一系（懸濁状態）で使用するのが好ましい。The catalyst used in the present invention is ammonium hydrogen sulfate (NH4
ISO, ), and commercially available ones can be used. The amount of the catalyst used is 0.5 to 20% by weight, preferably 2 to 10% by weight, based on the total weight of the reaction system. Although the catalyst can be used as an aqueous solution, it is preferable to add it directly to the reaction solution and use it in a heterogeneous system (suspended state).
反応は過剰のアセトンを溶媒として用いて行うのが好ま
しいが、他の溶媒を使用することもできる。溶媒として
は、例えばメタノール、エタノールなどの脂肪族低級ア
ルコールを例示できる。このような溶媒は、 （アセト
ンおよび／またはアセトンの縮合物）／溶媒の重量比で
１〜２０、好ましくは２〜１０の割合で使用するのが好
ましい。The reaction is preferably carried out using excess acetone as solvent, but other solvents can also be used. Examples of the solvent include aliphatic lower alcohols such as methanol and ethanol. Such a solvent is preferably used in a weight ratio of (acetone and/or acetone condensate)/solvent of 1 to 20, preferably 2 to 10.
反応は、アセトンおよび／またはアセトンの縮合物、触
媒としての硫酸水素アンモニウム、および必要に応じて
溶媒を加えた反応液中にアンモニアを吹き込みアセトニ
ンを合成する第１段反応と、アンモニアの吹き込みを止
め、第１段反応で生成したアセトニンを分離精製するこ
となく、第１段反応に続いて加熱攪拌して２，２，６．
６−テトラメチル−４−オキソピペリジンを合、成する
第２段反応に分けて行うのが好ましい。第１段反応では
、上記の混合物にアンモニアを吹き込む方法の代わりに
、アセトンおよび／またはアセトンの縮合物、触媒、溶
媒を一定の割合で連続的にフィードすると同時に、アセ
トンに対して前記割合のアンモニアを吹き込んで反応さ
せてもよい。The reaction consists of a first stage reaction in which acetonin is synthesized by blowing ammonia into a reaction mixture containing acetone and/or acetone condensate, ammonium hydrogen sulfate as a catalyst, and a solvent as necessary, and a first stage reaction in which acetonin is synthesized by blowing ammonia into the reaction mixture. , without separating and purifying the acetonin produced in the first stage reaction, following the first stage reaction, heating and stirring were carried out in 2, 2, 6.
It is preferable to carry out the reaction separately in a second stage reaction in which 6-tetramethyl-4-oxopiperidine is synthesized. In the first stage reaction, instead of blowing ammonia into the above-mentioned mixture, acetone and/or acetone condensate, catalyst, and solvent are continuously fed at a fixed ratio, and at the same time, ammonia is added at the above ratio to acetone. may also be reacted by blowing into it.
第１段反応の反応温度は０〜７０℃、好ましくは２０〜
６０℃、反応時間は１〜１０時間、好ましくは２〜６時
間、反応圧力は１〜１０気圧、好ましくは１〜５気圧で
ある。The reaction temperature of the first stage reaction is 0 to 70°C, preferably 20 to 70°C.
The reaction time is 1 to 10 hours, preferably 2 to 6 hours, and the reaction pressure is 1 to 10 atm, preferably 1 to 5 atm.
第２段反応の反応温度は５５〜１００℃、好ましくは６
０〜８０℃の第１段より高い温度、反応時間は１〜２０
時間、好ましくは２〜６時間である。第２段反応の反応
圧力は特に限定されない。The reaction temperature of the second stage reaction is 55 to 100°C, preferably 6
Temperature higher than the first stage of 0-80℃, reaction time 1-20℃
time, preferably 2 to 6 hours. The reaction pressure for the second stage reaction is not particularly limited.
上記反応の反応器の形式は特に限定されず、種型、管型
など任意のものが使用できる。また、上記反応は、バッ
チ式、連続式のいずれの反応方式でもよく、液相反応と
するのが好ましい。The type of reactor for the above reaction is not particularly limited, and any type such as a seed type or a tube type can be used. Furthermore, the above reaction may be carried out in either a batch or continuous manner, and is preferably a liquid phase reaction.
上記の方法によれば、消費されたアセトン基準で約７０
モル％の高い収率で２．２，６．６−テトラメチル−４
−オキソピペリジンを得ることができる。According to the above method, approximately 70
2.2,6.6-tetramethyl-4 in high yield of mol%
-Oxopiperidine can be obtained.
以上のようにして得られた２、２，６．６−テトラメチ
ル−４−オキソピペリジンは１例えば蒸留精製などの方
法により反応混合物から精製することができる。The 2,2,6,6-tetramethyl-4-oxopiperidine obtained as described above can be purified from the reaction mixture by a method such as distillation purification.
このようにして単離された２、２，６．６−テトラメチ
ル−４−オキソピペリジンは、高分子安定剤、漂白剤の
原料などに使用される。The 2,2,6,6-tetramethyl-4-oxopiperidine thus isolated is used as a raw material for polymer stabilizers, bleaching agents, and the like.
〔発明の効果〕
本発明によれば、硫酸水素アンモニウム触媒の存在下で
、アセトンおよび／またはアセトンの縮合物とアンモニ
アとを反応させるようにしたので、工業的に有利な方法
で、しかも高収率で２．２，６．６−テトラメチル−４
−オキソピペリジンを製造できる。[Effects of the Invention] According to the present invention, acetone and/or acetone condensate are reacted with ammonia in the presence of an ammonium hydrogen sulfate catalyst, which is an industrially advantageous method with high yield. 2.2,6.6-tetramethyl-4
- Oxopiperidine can be produced.
また、硫酸水素アンモニウムを触媒として使用している
ため、塩化アンモニウムを触媒として使用する場合のよ
うに耐ハライド性材質の反応器を使用する必要がなく、
また硫酸を触媒として使用した場合に生じるメタノール
、アセトンなどの損失を防止することができる。In addition, since ammonium hydrogen sulfate is used as a catalyst, there is no need to use a reactor made of halide-resistant material, unlike when ammonium chloride is used as a catalyst.
Furthermore, it is possible to prevent the loss of methanol, acetone, etc. that occurs when sulfuric acid is used as a catalyst.
以下、本発明の実施例について説明する。 Examples of the present invention will be described below.
実施例１
アセトン２６１．４ｇ（４，５モル）、メタノール６１
．８ｇおよび硫酸水素アンモニウム１７．３ｇ （０，
１５モル）からなる混合物に、４５℃でアンモニア１９
．３ｇ（１，１３モル）を３時間にわたって吹き込んだ
。アンモニアの吹き込みを止めて昇温し、３時間加熱還
流した。反応液に硫酸水素アンモニウムの２倍モル量の
水酸化ナトリウムを水溶液として加えて中和し、ガスク
ロマトグラフィーで分析した。その結果、２，２゜６．
６−テトラメチル−４−オキソピペリジンが７０．７ｇ
生成していることが判った。使用したアンモニア基準の
収率は４０．３モル％、消費されたアセトン基準の収率
は６８．４モル％であった。Example 1 Acetone 261.4g (4.5 mol), methanol 61
．． 8g and ammonium hydrogen sulfate 17.3g (0,
15 mol) of ammonia at 45°C.
．． 3 g (1.13 mol) were bubbled in over 3 hours. The blowing of ammonia was stopped, the temperature was raised, and the mixture was heated under reflux for 3 hours. The reaction solution was neutralized by adding twice the molar amount of sodium hydroxide as ammonium hydrogen sulfate as an aqueous solution, and analyzed by gas chromatography. As a result, 2.2°6.
70.7g of 6-tetramethyl-4-oxopiperidine
It was found that it was generated. The yield based on the ammonia used was 40.3 mol%, and the yield based on the consumed acetone was 68.4 mol%.
実施例２
１Ｑオートクレーブ中にアセトン２６１．４ｇ（４，５
モル）、メタノール６１．８ｇおよび硫酸水素アンモニ
ウム１７．３ｇ （０，１５モル）を入れ、この混合物
に５０℃でアンモニア１４．０ｇ（０，８２２モル）を
３時間にわたって吹き込んだ。アンモニアの吹き込みを
止めて昇温し、６０℃で３時間加熱攪拌した。反応液に
硫酸水素アンモニウムの２倍モル量の水酸化ナトリウム
を水溶液として加えて中和し、ガスクロマトグラフィー
で分析した。その結果、２，２，６，６−テトラメチル
−４−オキソピペリジンが７９．３ｇ生成していること
が判った。使用したアンモニア基準の収率は６２．１モ
ル％、消費されたアセトン基準の収率は６３．４モル％
であった。Example 2 261.4 g of acetone (4,5
mol), 61.8 g of methanol and 17.3 g (0.15 mol) of ammonium hydrogen sulfate were added, and 14.0 g (0.822 mol) of ammonia was bubbled into the mixture at 50° C. over a period of 3 hours. The blowing of ammonia was stopped, the temperature was raised, and the mixture was heated and stirred at 60° C. for 3 hours. The reaction solution was neutralized by adding twice the molar amount of sodium hydroxide as ammonium hydrogen sulfate as an aqueous solution, and analyzed by gas chromatography. As a result, it was found that 79.3 g of 2,2,6,6-tetramethyl-4-oxopiperidine was produced. The yield based on the ammonia used was 62.1 mol%, and the yield based on the consumed acetone was 63.4 mol%.
Met.
実施例３
温度を５０℃に保った反応容積１５０ｍ１２の第１槽に
、アセトン−メタノール溶液（重量比４．２：１）を１
時間あたり５０ａ＋Ｑ（アセトン３２．３ｇ（０，５５
６モル）／ｈｒ）。Example 3 In a first tank with a reaction volume of 150 m12 kept at a temperature of 50°C, 1 part of an acetone-methanol solution (weight ratio 4.2:1) was added.
50a+Q (acetone 32.3g (0,55
6 mol)/hr).
アンモニアを１時間あたり２−５ｇ （０，１４７モル
）および硫酸水素アンモニウムを１時間島たり２゜１ｇ
（ｏ、ｏｔａモル）の割合でフィードし、溢流液を反応
容積１５０ｍＱの第２槽に導き、加熱還流した。ガスク
ロマトグラフィー分析の結果、フィード開始１２時間後
の第１槽からの溢流液には、アセトニンが１６．９重量
％、２，２，６．６−テトラメチル−４−オキソピペリ
ジンが６．０重量％含まれており、また第２槽からの渦
流液には、アセトニンが３．２重量％、２．２゜６．６
−テトラメチル−４−オキソピペリジンが１８．２重量
％含まれていることが判った。２，２，６．６−テトラ
メチル−４−オキソピペリジンの収率は使用したアンモ
ニア基準で３５．６モル％、消費されたアセトン基準で
６３．５モル％であった。2-5 g (0,147 mol) of ammonia per hour and 2°1 g of ammonium hydrogen sulfate per hour.
The overflow liquid was introduced into a second tank with a reaction volume of 150 mQ and heated to reflux. As a result of gas chromatography analysis, the overflow from the first tank 12 hours after the start of feeding contained 16.9% by weight of acetonin and 6.9% by weight of 2,2,6.6-tetramethyl-4-oxopiperidine. The vortex liquid from the second tank contains 3.2% by weight of acetonin, 2.2°6.6
It was found that 18.2% by weight of -tetramethyl-4-oxopiperidine was contained. The yield of 2,2,6.6-tetramethyl-4-oxopiperidine was 35.6 mol% based on the ammonia used and 63.5 mol% based on the acetone consumed.
実施例４
実施例１において、アセトン２６１．４ｇに代えて、ア
セトン１７４．２ｇ （３，０モル）およびメシチルオ
キシド７３．６ｇ （０，７５モル）を用いた以外は実
施例１と同様に反応を行った。その結果、２，２．６．
６−テトラメチル−４−オキソピペリジンが６７．５［
生成した。使用したアンモニア基準の収率は３８．４モ
ル％であった。Example 4 Same as Example 1 except that 174.2 g (3.0 mol) of acetone and 73.6 g (0.75 mol) of mesityl oxide were used instead of 261.4 g of acetone. The reaction was carried out. As a result, 2, 2.6.
6-tetramethyl-4-oxopiperidine is 67.5[
generated. The yield based on the ammonia used was 38.4 mol%.
比較例１
実施例１において、硫酸水素アンモニウムに代えてａ酸
アンモニウム１９．８ｇ （０，１５モル）を用いた以
外は実施例１と同様に反応を行った。その結果、２．２
，６．６−テトラメチル−４−オキソピペリジンは使用
したアンモニア基準で０．２モル％生成したのみで、ア
セトニンが主生成物（使用したアンモニア基準収率４８
．１モル％）であった。Comparative Example 1 The reaction was carried out in the same manner as in Example 1 except that 19.8 g (0.15 mol) of ammonium a-acid was used in place of ammonium hydrogen sulfate. As a result, 2.2
, 6.6-tetramethyl-4-oxopiperidine was produced in only 0.2 mol% based on the ammonia used, and acetonin was the main product (yield 48% based on the ammonia used).
．． 1 mol%).
比較例２
実施例１において、硫酸水素アンモニウムに代えて塩化
アンモニウム８．０ｇ（０，１５モル）を用いた以外は
実施例１と同様に反応を行った。その結果、２．２，６
．６−テトラメチル−４−オキソピペリジンが６８．０
ｇ生成した。使用したアンモニア基準の収率は３８．７
モル％、消費されたアセトン基準の収率は６４．２モル
％であった。Comparative Example 2 The reaction was carried out in the same manner as in Example 1 except that 8.0 g (0.15 mol) of ammonium chloride was used in place of ammonium hydrogen sulfate. As a result, 2.2,6
．． 6-tetramethyl-4-oxopiperidine is 68.0
g was produced. The yield based on the ammonia used was 38.7
The yield based on mol% and consumed acetone was 64.2 mol%.
比較例３
実施例１において、硫酸水素アンモニウムに代えて濃硫
酸７．５ｇ（０，０７５モル）を用い、アンモニアを２
１．８ｇ （１，２８モル）吹き込んだ以外は実施例１
と同様に反応を行った。その結果、２，２，６，６−テ
トラメチル−４−オキソピペリジンが６６．１ｇ生成し
た。使用したアンモニア基準の収率は３３．３モル％、
消費されたアセトン基準の収率は６３．５モル％であっ
た。Comparative Example 3 In Example 1, 7.5 g (0,075 mol) of concentrated sulfuric acid was used instead of ammonium hydrogen sulfate, and ammonia was
Example 1 except that 1.8 g (1.28 mol) was blown into the
The reaction was carried out in the same manner. As a result, 66.1 g of 2,2,6,6-tetramethyl-4-oxopiperidine was produced. The yield based on the ammonia used was 33.3 mol%,
The yield based on consumed acetone was 63.5 mol%.
この場合、メタノール回収率は旧、３重量％であった。In this case, the methanol recovery rate was previously 3% by weight.
Claims (1)
モニアとを反応させて２，２，６，６−テトラメチル−
４−オキソピペリジンを製造するにあたり、硫酸水素ア
ンモニウムを触媒として用いることを特徴とする２，２
，６，６−テトラメチル−４−オキソピペリジンの製造
方法。(1) Reacting acetone and/or acetone condensate with ammonia to produce 2,2,6,6-tetramethyl-
2,2 characterized in that ammonium hydrogen sulfate is used as a catalyst in producing 4-oxopiperidine.
, 6,6-tetramethyl-4-oxopiperidine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63300314A JP2671458B2 (en) | 1988-11-28 | 1988-11-28 | Method for producing 2,2,6,6-tetramethyl-4-oxopiperidine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63300314A JP2671458B2 (en) | 1988-11-28 | 1988-11-28 | Method for producing 2,2,6,6-tetramethyl-4-oxopiperidine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02145570A true JPH02145570A (en) | 1990-06-05 |
| JP2671458B2 JP2671458B2 (en) | 1997-10-29 |
Family
ID=17883288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63300314A Expired - Fee Related JP2671458B2 (en) | 1988-11-28 | 1988-11-28 | Method for producing 2,2,6,6-tetramethyl-4-oxopiperidine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2671458B2 (en) |
-
1988
- 1988-11-28 JP JP63300314A patent/JP2671458B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2671458B2 (en) | 1997-10-29 |
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