JPH02204480A - Production of 2,2,6,6-tetramethyl-4-oxopiperidine - Google Patents
Production of 2,2,6,6-tetramethyl-4-oxopiperidineInfo
- Publication number
- JPH02204480A JPH02204480A JP2452389A JP2452389A JPH02204480A JP H02204480 A JPH02204480 A JP H02204480A JP 2452389 A JP2452389 A JP 2452389A JP 2452389 A JP2452389 A JP 2452389A JP H02204480 A JPH02204480 A JP H02204480A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- reactor
- ammonia
- stage
- acetone
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 title description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 86
- 238000006243 chemical reaction Methods 0.000 claims abstract description 79
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 74
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 43
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 claims description 5
- 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 abstract description 10
- 230000035484 reaction time Effects 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 4
- 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 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000012295 chemical reaction liquid Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- -1 holone Chemical compound 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 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 1
- WWILHZQYNPQALT-UHFFFAOYSA-N 2-methyl-2-morpholin-4-ylpropanal Chemical compound O=CC(C)(C)N1CCOCC1 WWILHZQYNPQALT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- CQTRUFMMCCOKTA-UHFFFAOYSA-N diacetoneamine hydrogen oxalate Natural products CC(=O)CC(C)(C)N CQTRUFMMCCOKTA-UHFFFAOYSA-N 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Landscapes
- Hydrogenated Pyridines (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（トリアセトンアミン、以下ＴＡＡと
称する場合がある）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 (triacetonamine, hereinafter sometimes referred to as TAA).
従来ＴＡＡの製造方法には、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出発原料として、２，
２，４，４．６−ベンタメチルー２，３，４．５−テト
ラヒドロピリミジン（アセトニン、以下アセトニンと称
する場合がある）を生成する第１段目の反応、および第
１段目の反応で生成したアセトニンからＴＡＡを生成す
る第２段目の反応からなる製造方法がある。Conventional methods for producing TAA include using acetone and/or acetone condensate and ammonia as starting materials, 2.
The first stage reaction that produces 2,4,4,6-bentamethyl-2,3,4,5-tetrahydropyrimidine (acetonin, hereinafter sometimes referred to as acetonin), and the reaction produced in the first stage reaction. There is a production method that includes a second stage reaction of producing TAA from acetonin.
ところが上記第２段目の反応では多量のアンモニアが生
成する（理論的にはＴＡＡの生成量と等モル量）ため、
ＴＡＡの製造を常温バッチ方式で行うと多量のアンモニ
アが排出される。この排出されたアンモニアを有効に利
用するために捕集して、第１段目の反応の出発原料とし
て再使用することができるが、この場合第１段目の反応
が発熱反応であるので、反応系の温度が高温になりすぎ
ることによる収率の低下を防ぐために、供給するアンモ
ニアの量を調節して反応系の温度を制御する必要がある
。このため第２段目の反応で排出されたアンモニアを第
１段目の反応に再使用する場合、操作が煩雑で設備費が
高くなるという問題点がある。However, in the second stage reaction, a large amount of ammonia is produced (theoretically, the amount is equivalent to the amount of TAA produced), so
When TAA is produced in a room-temperature batch process, a large amount of ammonia is emitted. In order to effectively utilize this discharged ammonia, it can be collected and reused as a starting material for the first stage reaction, but in this case, since the first stage reaction is an exothermic reaction, In order to prevent a decrease in yield due to the temperature of the reaction system becoming too high, it is necessary to control the temperature of the reaction system by adjusting the amount of ammonia supplied. Therefore, when the ammonia discharged in the second stage reaction is reused in the first stage reaction, there are problems in that the operation is complicated and the equipment cost is high.
また全体の反応を密閉系で行い、アンモニアの排出を防
ぐことができるが、この場合反応温度の制御が難しく、
特に反応系の規模が大きくなると安全運転確保の点で問
題がある。さらにアンモニアが排出されないので反応時
間がやや長くなるという問題点もある。Additionally, the entire reaction can be carried out in a closed system to prevent ammonia emissions, but in this case it is difficult to control the reaction temperature.
Particularly when the scale of the reaction system becomes large, there is a problem in ensuring safe operation. Furthermore, since ammonia is not discharged, there is also the problem that the reaction time is somewhat longer.
本発明の目的は、上記問題点を解決するため、アンモニ
アを有効に利用でき、しかも簡単な操作で、生産コスト
が安く、安全で、反応時間が短く、かつ高収率でＴＡＡ
を製造す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 using ammonia effectively, with simple operation, low production cost, safety, short reaction time, and high yield of TAA.
The objective is to propose a method for manufacturing.
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−オキソピペリジンを製造するにあたり。The present invention relates to the production of 2,2,6,6-tetramethyl-4-oxopiperidine by reacting acetone and/or acetone condensate with ammonia.
第１反応器で触媒の存在下にアセトンおよび／またはア
セトンの縮合物とアンモニアとを反応温度４０〜６０℃
、平均滞留時間１〜１０時間で反応させて第１段目の反
応を行い、第２反応器で前記第１反応器の反応液を反応
温度５０〜１００℃、平均滞留時間】、〜１０時間で反
応させて第２段目の反応を行うとともに、前記第２段目
の反応で生成するアンモニアを前記第１反応器にフィー
ドして前記アセトンおよび／またはアセトンの縮合物と
の反応に利用す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である。In the first reactor, acetone and/or acetone condensate and ammonia are reacted at a temperature of 40 to 60°C in the presence of a catalyst.
, the first stage reaction is carried out at an average residence time of 1 to 10 hours, and the reaction solution from the first reactor is transferred to a second reactor at a reaction temperature of 50 to 100°C and an average residence time of ~10 hours. At the same time, the ammonia produced in the second stage reaction is fed to the first reactor and used for the reaction with the acetone and/or the condensate of acetone. This is a method for producing 2,2,6,6-tetramethyl-4-oxopiperidine, characterized by the following.
第１７図は本発明のＴＡＡの製造方法の概略を示す工程
図であり、１は第１段目の反応を行う第１反応器、２は
第２段目の反応を行う第２反応器であり、それぞれ独立
して設けられている。３は第１反応液、４は第２反応液
を示す。本発明のＴＡＡの製造方法は、まずアセトン５
および／またはアセトンの縮合物、アンモニア６および
触媒７を連続的に第１反応器エヘフィードして第１段目
の反応を行い、主としてアセトニンを含む第１反応液３
を得、次にこの第１反応液３を連続的に第２反応器２へ
導いて第２段目の反応を行い、連続的にＴＡＡを主成分
とする第２反応液４を得、この第２反応液４を中和洗浄
後蒸留等により精製してＴＡＡを得る。この際に第２段
目の反応では多量のアンモニア（理論的にはＴＡＡの生
成量と等モル量）が生成するので、この生成したアンモ
ニア８ （以下生成アンモニアと称する）を生成アンモ
ニア８とは別の新たにフィードする新アンモニア６とと
もに連続的に第１反応器】ヘフィードして生成アンモニ
ア８を有効に利用する。FIG. 17 is a process diagram showing an outline of the method for producing TAA of the present invention, in which 1 is a first reactor for carrying out the first stage reaction, and 2 is a second reactor for carrying out the second stage reaction. Yes, each is set up independently. 3 indicates the first reaction solution, and 4 indicates the second reaction solution. The method for producing TAA of the present invention begins with acetone 5
and/or acetone condensate, ammonia 6, and catalyst 7 are continuously fed into the first reactor to perform the first stage reaction, and the first reaction liquid 3 mainly contains acetonin.
Then, this first reaction liquid 3 is continuously led to the second reactor 2 to perform the second stage reaction, and a second reaction liquid 4 containing TAA as the main component is continuously obtained. After neutralization and washing, the second reaction solution 4 is purified by distillation or the like to obtain TAA. At this time, a large amount of ammonia (theoretically equivalent to the amount of TAA produced) is produced in the second stage reaction, so this produced ammonia 8 (hereinafter referred to as "produced ammonia") is referred to as "produced ammonia 8". The produced ammonia 8 is effectively utilized by continuously feeding it to the first reactor together with fresh ammonia 6 that is newly fed.
本発明の第１段目の反応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７ては、例えばアセトン、メ
シチルオキシド、ジアセＩ−ンアルコール、ホロン、あ
るいはアセトニン、ジアセトンアミン等を含む第２反応
液４蒸留の初留分などを例示できる。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。Examples of the acetone and/or acetone condensate 7 used in the first stage reaction of the present invention include acetone, mesityl oxide, diacetone alcohol, holone, acetonin, diacetone amine, etc. An example is the first distillate of two reaction solutions and four distillations. These may be used alone or in combination of two or more.
本発明において、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
ニアの割合がモル比で３〜１０．好ましくは３，５〜６
となるように反応させる。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 the present invention, the starting materials of acetone and/or acetone condensate and ammonia have an acetone/ammonia molar ratio of 3 to 10. Preferably 3,5-6
React so that In this case, the molar ratio of the acetone condensate is determined in terms of acetone.
上記出発原料の使用割合を上記範囲にすることにより、
第１段目の反応の第１反応液３をそのまま第２段目の反
応に使用できる。By keeping the usage ratio of the above starting materials within the above range,
The first reaction solution 3 from the first stage reaction can be used as it is for the second stage reaction.
本発明の第１段目の反応で使用する触媒としては、プロ
トン酸またはプロトン酸のアンモニウム塩が好ましい。The catalyst used in the first stage reaction of the present invention is preferably a protonic acid or an ammonium salt of a protonic acid.
このような触媒として１例えば硫酸、硫酸水素アンモニ
ウム、塩化アンモニウムなどを例示できる。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１〜１０重景％が好ましい。触媒は反応液中にそ
のまま添加して使用すればよく、均一系（必要により系
内の水に溶解した溶液状態）、不均一系（懸濁状態）の
いずれの形態であってもよい。Examples of such catalysts include sulfuric acid, ammonium hydrogen sulfate, and ammonium chloride. The amount of the catalyst used is preferably 0.5 to 20% by weight, preferably 1 to 10% by weight based on the total weight of the reaction system. The catalyst may be used by being added to the reaction solution as it is, and may be in either a homogeneous system (a solution state dissolved in water in the system if necessary) or a heterogeneous system (suspension state).
本発明の反応では、過剰のアセトンを溶媒として使用す
るのが好ましいが、他の溶媒を使用してもよい、このよ
うな溶媒としては、例えばメタノール、エタノール等の
脂肪族低級アルコール、水などを例示できる。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、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１〜５０、好まし
くは２〜３５の割合で使用するのが好ましい。In the reaction of the present invention, it is preferred to use excess acetone as a solvent, but other solvents may also be used, such as lower aliphatic alcohols such as methanol and ethanol, water, etc. I can give an example. These may be used alone or in combination of two or more.Such solvents have a weight ratio of (acetone and/or acetone condensate)/solvent of 1 to 50, Preferably, it is used in a ratio of 2 to 35.
第１段目の反応の反応条件は反応温度が通常４０〜６０
℃、好ましくは４５〜５５℃未満、反応時間が通常平均
滞留時間で１〜１０時間、好ましくは２〜６時間時間路
反応圧力常１〜１０気圧、好ましくは１〜５気圧である
。The reaction conditions for the first stage reaction are usually a reaction temperature of 40 to 60°C.
C, preferably less than 45 to 55 C, and the reaction time is usually 1 to 10 hours, preferably 2 to 6 hours with an average residence time, and the reaction pressure is usually 1 to 10 atm, preferably 1 to 5 atm.
第２段目の反応は、第１反応器１の第１反応液３を連続
的に第２反応器２に導きながら、通常５０〜１００℃、
好ましくは５５〜７０℃という第１段目より高い反応温
度で、通常平均滞留時間１〜１０時間、好ましくは２〜
６時間加熱攪拌する反応条件で実施する。この反応の反
応圧力は特に限定されないが、１〜３気圧下で行うのが
好ましい、この反応により、アセトニンからＴＡＡが１
５〜２５重量％の反応系内濃度で生成する。In the second stage reaction, the first reaction liquid 3 in the first reactor 1 is continuously introduced into the second reactor 2, usually at a temperature of 50 to 100°C.
The reaction temperature is higher than the first stage, preferably 55-70°C, and the average residence time is usually 1-10 hours, preferably 2-10 hours.
The reaction is carried out under heating and stirring conditions for 6 hours. The reaction pressure of this reaction is not particularly limited, but it is preferably carried out under 1 to 3 atmospheres.
It is produced at a concentration in the reaction system of 5 to 25% by weight.
ここで平均滞留時間とは、反応器にフィードされる反応
原料の総量と反応器の容量とから算出される時間である
。Here, the average residence time is a time calculated from the total amount of reaction raw materials fed to the reactor and the capacity of the reactor.
本発明の反応を行うための反応器は第１反応器１および
第２反応器２とも特に限定されないが、種型が好ましい
、また第１反応器１および第２反応器２ともそれぞれ複
数の反応器を使用してもよい。The reactor for carrying out the reaction of the present invention is not particularly limited to either the first reactor 1 or the second reactor 2, but a seed type is preferable. You may use a container.
本発明の第１段目の反応および第２段目の反応は、均一
系または不均一系の液相反応として行うことができる。The first stage reaction and second stage reaction of the present invention can be carried out as a homogeneous or heterogeneous liquid phase reaction.
上記の製造方法により、第２段目の反応で生成する生成
アンモニアを有効に利用でき、しかも従来の方法に比べ
て簡単な操作で、生産コストが安く、安全で１反応時間
が短く、かつ消費されたアセトン基準の収率で５０〜６
５モル％程度と高い収率でＴＡＡを製造することができ
る。The above production method makes it possible to effectively utilize the ammonia produced in the second stage reaction, and is simpler to operate, lower in production cost, safer, shorter in one reaction time, and less consumptive than conventional methods. The yield based on acetone was 50-6.
TAA can be produced with a high yield of about 5 mol%.
本発明の方法で製造されたＴＡＡは、中和洗浄後蒸留精
製などの方法により精製することにより、純度９８％以
上の高純度の製品とすることができる。The TAA produced by the method of the present invention can be purified by a method such as neutralization washing followed by distillation purification, and can be made into a highly pure product with a purity of 98% or more.
このようにして製造されたＴＡＡは、高分子安定剤、漂
白剤の原料などに使用できる。TAA produced in this manner can be used as a raw material for polymer stabilizers, bleaching agents, and the like.
以上の通り１本発明によれば、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アセトニンを生成
する第１段目の反応と、アセトニンからＴＡＡを生成す
る第２段目の反応をそれぞれ別々の反応器で行うととも
に、第２段目の反応で生成する生成アンモニアを新アン
モニアとともに第１反応器ヘフィードするようにしたの
で、アンモニアを有効に利用でき、しかも簡単な操作で
、生産コストが安く、安全で、反応時間が短く、かつ高
収率でＴＡＡを製造することができる。As described above, according to the present invention, the first stage reaction of producing acetonin from acetone and/or acetone condensate and ammonia and the second stage reaction of producing TAA from acetonin are carried out separately. In addition to carrying out the reaction in a reactor, the ammonia produced in the second stage reaction is fed to the first reactor along with new ammonia, so ammonia can be used effectively, and the operation is simple and production costs are low. TAA can be produced safely, in a short reaction time, and in high yield.
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
温度を４５℃に保った反応容積５００ｍＱの第１反応器
にアセトンを１時間あたり１３７ｍｆｌ、硫酸のメタノ
ール溶液（１０重量％）を１時間あたり３８−の割合で
フィードし、さらに第２反応器から排出されるアンモニ
アとともに新アンモニアを１時間あたり５．７ｇの割合
で吹き込んだ６第１反応器からの溢流液を反応容積５０
０ｍＱの第２反応器へ連続的に導き。Example 1 Acetone was fed at a rate of 137 mfl per hour and a methanol solution of sulfuric acid (10% by weight) was fed at a rate of 38 mfl per hour into a first reactor with a reaction volume of 500 mQ, the temperature of which was maintained at 45°C. New ammonia was blown in at a rate of 5.7 g per hour together with the ammonia discharged from the reactor.6 The overflow from the first reactor was mixed into a reaction volume of 50.
Continuously led to a second reactor with 0 mQ.
加熱還流した。この時の第１反応器および第２反応器で
の平均滞留時間はいずれも約３時間である。The mixture was heated to reflux. At this time, the average residence time in both the first reactor and the second reactor is about 3 hours.
ガスクロマトグラフィーの結果、フィード開始から１２
時間後の第１反応器からの溢流液にはアセトニンが１７
．３重量％、２，２，６，６−テトラメチル−４−オキ
ソピペリジンが９．２重量％含まれており、また第２反
応器からの溢流液にはアセトニンが２．９重量％、 ２
，２，６，６−テトラメチル−４−オキソピペリジンが
２１．３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５８．２モル％、情実された
アセトン基準で６３．２モル％であった。As a result of gas chromatography, 12
After an hour, the overflow from the first reactor contained 17 acetonin.
．． 3% by weight, 9.2% by weight of 2,2,6,6-tetramethyl-4-oxopiperidine, and the overflow from the second reactor contained 2.9% by weight of acetonin. 2
, 2,6,6-tetramethyl-4-oxopiperidine was found to be contained in an amount of 21.3% by weight. The yield of 2,2゜6.6-tetramethyl-4-oxopiperidine was 58.2 mol% based on the ammonia used and 63.2 mol% based on the acetone used.
実施例２
温度を５０１ユに保った反応容積５００ｎＪの第１尺ハ
シ器に３重藍％ｎ°水アセ（・ンを１時間あたり１２５
ｍＱ。Example 2 Into a first scale vessel with a reaction volume of 500 nJ and keeping the temperature at 501 units, triple indigo% n° water acetate was added at 125% per hour.
mQ.
塩化アンモニウムを３時間島たり３゜Ｏｇの割合でフィ
ードし、さらに第２反応器からＨト出されるアンモ−ア
とともに新アンモ、−”アを〕７時間あたり５．２Ｂの
割合で吹き込ん；ご。第１反応器からの渦流液を反応容
積５００＋ｄの第２反応器へ連続的に導き、加熱還流し
た。この時の第１２反応器および第２反Ｊδ器での平均
滞留時間はいずれも約４時間でＩ）ｌる。Ammonium chloride was fed at a rate of 3° Og per hour for 3 hours, and fresh ammonia, ``a'' was blown in at a rate of 5.2 B per 7 hours along with the ammonia discharged from the second reactor; The turbulent liquid from the first reactor was continuously led to a second reactor with a reaction volume of 500+d and heated to reflux.The average residence time in the 12th reactor and the second Jδ reactor at this time was approximately I) in 4 hours.
ガスクロマトグラフィーの結果、フィード開始から１６
時間後の第１反応器かＧ’４の溢流液にはｊ′ヤ１−ニ
ンが１８．３重量％、２，２，６．６テ１−ラメチル−
４・−オキソピペリジンが１１゜７重板％さすれており
、また第２反応器からの溢流液ＬＪ、はアセ］−ニンが
２．９重量％、２，２，６，６−チトラメｆ・ルー４−
オキソピペリジンが２２．１重量％含まれていることが
判った。２．ハロ、６−テ１−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５０．１モ
ル％、消費されたアセトン基準で６０゜２モル％であ−
ノた。As a result of gas chromatography, 16
After hours, the overflow from the first reactor or G'4 contained 18.3% by weight of
The overflow LJ from the second reactor contains 2.9% by weight of ace]-nin and 2,2,6,6-titramethane. F. Lou 4-
It was found that 22.1% by weight of oxopiperidine was contained. 2. The yield of halo,6-teramethyl-4-oxopiperidine was 50.1 mol% based on the ammonia used and 60.2 mol% based on the acetone consumed.
Nota.
実施例３−・・４
実施例２において平均滞留時間（約４［，７間）を第１
表に示す時間１・Ｊ、変えた以グは実施例２と同様に反
応を行った。結果を第１表に示す。Example 3--4 In Example 2, the average residence time (approximately 4 [, 7]) was
The reaction was carried out in the same manner as in Example 2 except that the time shown in the table was changed to 1.J. The results are shown in Table 1.
第１表
注１） ＴＡＡ：２，２，６，６−ヂト・ラメチル・−
４−オキソピペリジン実施例５
実施例２において第１５反応器の温度を・４５て二に変
えた以外は実施例２と同様に反応を行った。その結果、
ＴＡＡ濃度は２３．２重量％、ＴＡＡ収率は使用したア
ンモニア基準で５２．６＋ル％、消費されたアセトン基
準で６２．３モル％であった。Table 1 Note 1) TAA: 2,2,6,6-dito-tramethyl-
4-Oxopiperidine Example 5 The reaction was carried out in the same manner as in Example 2, except that the temperature of the 15th reactor was changed from -45 to -2. the result,
The TAA concentration was 23.2% by weight, and the TAA yield was 52.6% by mole based on the ammonia used and 62.3% by mole based on the acetone consumed.
実施例６〜７
実施例２において第１、反応器に吹き込む新アンモニア
の量を第２表に示す量に変えた以外は実施例２と同様に
反応を行った。結果を第２表に示す。Examples 6 to 7 The reaction was carried out in the same manner as in Example 2, except that the amount of fresh ammonia blown into the first reactor was changed to the amount shown in Table 2. The results are shown in Table 2.
第２表
注１） ＴＡＡ：２，２，６，６−テトラメチル−４−
オキソピペリジンTable 2 Note 1) TAA: 2,2,6,6-tetramethyl-4-
Oxopiperidine
第１１図は本発明のＴＡＡの製造方法の概略を示す］二
程図である。
１：第１−反応器、２：第２反応器、３：第１反応液、
４：第２反応液、５：アセトン、６：アンモニア、７：
触媒、８：アンモニア。
代理人 弁理士 柳 原 成FIG. 11 is a two-step diagram schematically showing the method for manufacturing TAA of the present invention. 1: first reactor, 2: second reactor, 3: first reaction liquid,
4: Second reaction solution, 5: Acetone, 6: Ammonia, 7:
Catalyst, 8: Ammonia. Agent Patent Attorney Sei Yanagihara
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、第１反応器
で触媒の存在下にアセトンおよび／またはアセトンの縮
合物とアンモニアとを反応温度４０〜６０℃、平均滞留
時間１〜１０時間で反応させて第１段目の反応を行い、
第２反応器で前記第１反応器の反応液を反応温度５０〜
１００℃、平均滞留時間１〜１０時間で反応させて第２
段目の反応を行うとともに、前記第２段目の反応で生成
するアンモニアを前記第１反応器にフィードして前記ア
セトンおよび／またはアセトンの縮合物との反応に利用
す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-
In producing 4-oxopiperidine, acetone and/or acetone condensate and ammonia are reacted in the presence of a catalyst in a first reactor at a reaction temperature of 40 to 60°C and an average residence time of 1 to 10 hours. Perform the first stage reaction,
The reaction solution from the first reactor is transferred to the second reactor at a reaction temperature of 50 to
React at 100°C for an average residence time of 1 to 10 hours.
2, characterized in that while performing the reaction in the second stage, ammonia produced in the second stage reaction is fed to the first reactor and used for the reaction with the acetone and/or the condensate of acetone. ,2,6,6-tetramethyl-
Method for producing 4-oxopiperidine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2452389A JP2729219B2 (en) | 1989-02-02 | 1989-02-02 | Method for producing 2,2,6,6-tetramethyl-4-oxopiperidine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2452389A JP2729219B2 (en) | 1989-02-02 | 1989-02-02 | Method for producing 2,2,6,6-tetramethyl-4-oxopiperidine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02204480A true JPH02204480A (en) | 1990-08-14 |
| JP2729219B2 JP2729219B2 (en) | 1998-03-18 |
Family
ID=12140520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2452389A Expired - Fee Related JP2729219B2 (en) | 1989-02-02 | 1989-02-02 | Method for producing 2,2,6,6-tetramethyl-4-oxopiperidine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2729219B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2706056A1 (en) | 2012-09-07 | 2014-03-12 | Evonik Industries AG | Method for the preparation and treatment of a reaction mixture containing triacetonamine |
-
1989
- 1989-02-02 JP JP2452389A patent/JP2729219B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2706056A1 (en) | 2012-09-07 | 2014-03-12 | Evonik Industries AG | Method for the preparation and treatment of a reaction mixture containing triacetonamine |
| DE102012215900A1 (en) | 2012-09-07 | 2014-05-15 | Evonik Industries Ag | Process for the preparation and processing of a triacetonamine-containing reaction mixture |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2729219B2 (en) | 1998-03-18 |
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