JPS6121946B2 - - Google Patents
Info
- Publication number
- JPS6121946B2 JPS6121946B2 JP8901776A JP8901776A JPS6121946B2 JP S6121946 B2 JPS6121946 B2 JP S6121946B2 JP 8901776 A JP8901776 A JP 8901776A JP 8901776 A JP8901776 A JP 8901776A JP S6121946 B2 JPS6121946 B2 JP S6121946B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- reaction
- oxo
- hexanoic acid
- acid amide
- 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.)
- Expired
Links
- 239000003054 catalyst Substances 0.000 claims description 24
- GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical class CN1CCCCC1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000006297 dehydration reaction Methods 0.000 claims description 7
- 230000018044 dehydration Effects 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- MFOXCBPAYMJQPW-UHFFFAOYSA-N 2-oxohexanamide Chemical class CCCCC(=O)C(N)=O MFOXCBPAYMJQPW-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 16
- GHYDKOSNFZOHJJ-UHFFFAOYSA-N 5-oxohexanamide Chemical class CC(=O)CCCC(N)=O GHYDKOSNFZOHJJ-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 239000007789 gas Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000008246 gaseous mixture Substances 0.000 description 2
- ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- KWRCTXMRVADIJW-UHFFFAOYSA-N 2,4-dimethyl-5-oxohexanamide Chemical compound CC(=O)C(C)CC(C)C(N)=O KWRCTXMRVADIJW-UHFFFAOYSA-N 0.000 description 1
- MVKDNXIKAWKCCS-UHFFFAOYSA-N 3-methyl-1h-pyridin-2-one Chemical compound CC1=CC=CN=C1O MVKDNXIKAWKCCS-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
Description
【発明の詳細な説明】
本発明は、５−オキソ−ヘキサン酸アミド類を
出発物質とするメチルピペリジノン類の新規な製
造法に関する。さらに詳しくは、５−オキソ−ヘ
キサン酸アミド類を脱水触媒と接触させて脱水反
応を起こさせることにより、メチルピペリジノン
類を製造する方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel method for producing methylpiperidinones starting from 5-oxo-hexanoic acid amides. More specifically, the present invention relates to a method for producing methylpiperidinones by bringing 5-oxo-hexanoic acid amides into contact with a dehydration catalyst to cause a dehydration reaction.
従来、メチルピペリジノンは、ピリジンを酸化
しピリジノンとした後、アルキル化してメチルピ
リジノンを製造し、これを水素添加することによ
つて製造している。 Conventionally, methylpiperidinone has been produced by oxidizing pyridine to produce pyridinone, then alkylating it to produce methylpyridinone, and then hydrogenating this.
しかし、この従来法は、選択率が低く、副生物
も多いうえに工程が繁雑であるなどの欠点があ
る。 However, this conventional method has drawbacks such as low selectivity, many by-products, and complicated steps.
本発明者らは、従来法の前記のような欠点を解
消したメチルピペリジノン類の製造方法を提供す
ることを目的として、５−オキソ−ヘキサン酸ア
ミドの反応を詳細に研究した結果、５−オキソ−
ヘキサン酸アミドを脱水触媒に接触させると一段
の反応でメチルピペリジノンが収率よくえられる
ことを見出し、本発明を完成するに至つた。 The present inventors have conducted a detailed study on the reaction of 5-oxo-hexanoic acid amide with the aim of providing a method for producing methylpiperidinones that eliminates the above-mentioned drawbacks of conventional methods. -Oxo-
The present inventors discovered that methylpiperidinone can be obtained in good yield in a single reaction when hexanoic acid amide is brought into contact with a dehydration catalyst, leading to the completion of the present invention.
すなわち、本発明の方法は、５−オキソ−ヘキ
サン酸アミド類を脱水触媒と接触させることによ
りメチルピペリジノン類を製造する方法であり、
一段の反応操作で目的物を選択率よく製造するこ
とができるうえに、副生物の生成も極めて少ない
利点がある。 That is, the method of the present invention is a method for producing methylpiperidinones by contacting 5-oxo-hexanoic acid amides with a dehydration catalyst,
This method has the advantage that the target product can be produced with high selectivity through a single reaction operation, and that by-products are produced in very small quantities.
本発明の方法で用いる原料は、５−オキソヘキ
サン酸アミド類であつて、一般式
CH3 COCHR1 CH2 CHR2 CONH2
（式中、R1およびR2は、水素原子またはメチル基
を表わす）で示されるものである。 The raw materials used in the method of the present invention are 5-oxohexanoic acid amides and have the general formula CH 3 COCHR 1 CH 2 CHR 2 CONH 2 (wherein R 1 and R 2 represent a hydrogen atom or a methyl group). ).
生成物は、一般式
（式中、R1およびR2は、前記と同一の意味を表わ
す）で示されるメチルピペリジノン類が得られ
る。 The product has the general formula Methylpiperidinones represented by the formula (wherein R 1 and R 2 have the same meanings as above) are obtained.
出発物質である５−オキソヘキサン酸アミド類
は、工業的に安価に入手できるアセトンもしくは
メチルエチルケトンとアクリル酸アミドもしくは
メタアクリル酸アミドを塩基性触媒の存在下に反
応させて製造することができる。 The starting material, 5-oxohexanoic acid amide, can be produced by reacting acetone or methyl ethyl ketone, which is commercially available at low cost, with acrylic amide or methacrylic amide in the presence of a basic catalyst.
本発明の方法は液相もしくは気相、好ましくは
気相で、行なう。気相での反応は、触媒と反応生
成物の分離が容易であるという利点がある。気相
で反応を実施する際には、反応温度、すなわち、
触媒床の温度は、100〜400℃の範囲で、望ましく
は、200゜〜350℃の範囲である。 The process according to the invention is carried out in the liquid phase or in the gas phase, preferably in the gas phase. The reaction in the gas phase has the advantage that the catalyst and the reaction product can be easily separated. When carrying out the reaction in the gas phase, the reaction temperature, i.e.
The temperature of the catalyst bed is in the range of 100° to 400°C, preferably in the range of 200° to 350°C.
本発明の方法で用いる触媒は、通常、脱水能を
持つたものであれば使用することができる。すな
わち、脱水触媒としては、シリカ−アルミナ、γ
−アルミナ、シリカーチタニア、アルミナ−チタ
ニア、チタニア−ジルコニア、アルミナ−ボリア
などの固体酸性を示す物質、ならびに硫酸、燐酸
などが多用される。 The catalyst used in the method of the present invention can generally be any catalyst that has dehydration ability. That is, as a dehydration catalyst, silica-alumina, γ
- Solid acidic substances such as alumina, silica titania, alumina-titania, titania-zirconia, and alumina-boria, as well as sulfuric acid and phosphoric acid, are often used.
本発明の方法は、ガス状の出発物質を他の不活
性な有機化合物、たとえば、ベンゼン、ヘキサン
など、または無機化合物、たとえば、窒素、炭酸
ガスなどで希釈し、希釈したガス状反応原料を加
熱した、固定床もしくは流動床の触媒と接触させ
ることにより実施する。 The method of the invention involves diluting the gaseous starting material with another inert organic compound, such as benzene, hexane, etc., or with an inorganic compound, such as nitrogen, carbon dioxide, etc., and heating the diluted gaseous reaction material. This is carried out by contacting a fixed bed or fluidized bed catalyst.
使用する触媒に対する、反応原料５−オキソ−
ヘキサン酸アミド類の供給量は、触媒１ml当た
り、毎時0.1ないし５ｇの範囲が用いられる。 Reaction raw material 5-oxo- for the catalyst used
The amount of hexanoic acid amide to be fed is in the range of 0.1 to 5 g per hour per ml of catalyst.
反応圧力は、常圧ないし、20Kg/cm2の範囲が適
して居る。 The reaction pressure is suitably in the range of normal pressure to 20 kg/cm 2 .
触媒床を通過した反応混合物は、冷却すると凝
縮物を与へる。 The reaction mixture passed through the catalyst bed provides condensate upon cooling.
この凝縮物から、目的物を常法により分離し、
未反応物は回収して、反応系に循環使用する。 From this condensate, the target product is separated by a conventional method,
Unreacted materials are collected and recycled to the reaction system.
本発明の方法は、以上のように、気相で反応さ
せるのが有利であるが、また、液相、すなわち不
活性溶媒中で行なうこともできる。溶媒として
は、トルエン、キシレン、ジフエニルエーテル、
ハロゲン化芳香族化合物、またはパラフイン類な
どが用いられる。 As mentioned above, the method of the present invention is advantageously carried out in the gas phase, but it can also be carried out in the liquid phase, that is, in an inert solvent. Solvents include toluene, xylene, diphenyl ether,
Halogenated aromatic compounds or paraffins are used.
以下、実施例によつて本発明を説明する。 The present invention will be explained below with reference to Examples.
実施例 １
５−オキソ−ヘキサン酸アミド、窒素のガス状
混合物を内径18m/m、長さ500m/mのガラス製
反応管を４時間通過させた。反応器内にはシリカ
−アルミナ触媒が30ml充填してある。触媒の組成
は、アルミナ15重量％、シリカ85重量％であり、
触媒粒子の大きさは２〜３m/mの大きさに成型
してある。反応器は、外部より電気炉で加熱し、
触媒床の温度は、280〜290℃に保たれている。Example 1 A gaseous mixture of 5-oxo-hexanoic acid amide and nitrogen was passed through a glass reaction tube with an inner diameter of 18 m/m and a length of 500 m/m for 4 hours. The reactor was filled with 30 ml of silica-alumina catalyst. The composition of the catalyst is 15% by weight alumina and 85% by weight silica.
The size of the catalyst particles is 2 to 3 m/m. The reactor is heated from the outside with an electric furnace.
The temperature of the catalyst bed is maintained at 280-290°C.
反応開始に先立つて、300℃で１時間窒素ガス
を流し、触媒を活性化した。反応ガス状混合物
は、５−オキソ−ヘキサン酸アミド １モルに対
し窒素 ７モルの組成であり、５−オキソ−ヘキ
サン酸アミドの供給量は、触媒の１ml当たり、毎
時0.5ｇである。 Prior to the start of the reaction, nitrogen gas was flowed at 300° C. for 1 hour to activate the catalyst. The reaction gaseous mixture has a composition of 1 mole of 5-oxo-hexanoamide to 7 moles of nitrogen, and the feed rate of 5-oxo-hexanoamide is 0.5 g per hour per ml of catalyst.
２時間反応させ、反応が定常的になつてから、
生成ガス混合物を２時間、−６℃に冷却したトラ
ツプに通して補集した。生成物の分析結果は、未
反応５−オキソ−ヘキサン酸アミド、50重量％、
２−メチル−ピペリジノン−６ 41重量％、シク
ロヘキサン−１・３−ジオン、４重量％、であつ
た。 React for 2 hours, and after the reaction becomes steady,
The product gas mixture was collected for 2 hours through a trap cooled to -6°C. Analysis of the product revealed that 50% by weight of unreacted 5-oxo-hexanoic acid amide;
They were 41% by weight of 2-methyl-piperidinone-6 and 4% by weight of cyclohexane-1,3-dione.
実施例 ２
実施例１と同様の反応器と方法で、２・４−ジ
メチル−５−オキソ−ヘキサン酸アミド、１モ
ル、窒素 ５モル、ベンゼン ５モル、から成る
反応混合物を反応させた。反応器中には、シリカ
−チタニア（SiO2：TiO2＝60：40）の20メツシ
ユ粒状物が充填されており、触媒床は、300℃に
加熱されている。２・４−ジメチル−５−ヘキサ
ン酸アミドの供給量は、触媒１ml当たり、毎時
0.25ｇである。Example 2 In the same reactor and method as in Example 1, a reaction mixture consisting of 1 mole of 2,4-dimethyl-5-oxo-hexanoic acid amide, 5 moles of nitrogen, and 5 moles of benzene was reacted. Twenty mesh granules of silica-titania (SiO 2 :TiO 2 =60:40) are packed in the reactor and the catalyst bed is heated to 300°C. The feed rate of 2,4-dimethyl-5-hexanoic acid amide is per ml of catalyst per hour.
It is 0.25g.
反応を開始して２時間経過した後に反応生成物
の補集を開始し、３時間補集を行なつた。生成物
の分析結果は、未反応２・４−ジメチル−５−ヘ
キサン酸アミド 45重量％、２・３・５−トリメ
チル−ピペリジノン−６ 43重量％であつた。 Collection of reaction products was started after 2 hours had elapsed from the start of the reaction, and collection was continued for 3 hours. Analysis of the product revealed that it contained 45% by weight of unreacted 2,4-dimethyl-5-hexanoic acid amide and 43% by weight of 2,3,5-trimethyl-piperidinone-6.
実施例 ３
実施例１と同様の反応器と方法で、５−オキソ
−ヘキサン酸アミド １モル、窒素 ５モル、ベ
ンゼン ６モル、から成る反応混合物を反応させ
た。Example 3 Using the same reactor and method as in Example 1, a reaction mixture consisting of 1 mole of 5-oxo-hexanoic acid amide, 5 moles of nitrogen, and 6 moles of benzene was reacted.
反応器中には、燐酸を浸漬させて加熱処理した
粒状の活性炭（20メツシユ）が20ml充填してあ
る。 The reactor was filled with 20 ml of granular activated carbon (20 mesh) soaked in phosphoric acid and heat treated.
触媒床を320℃に加熱して、５−オキソ−ヘキ
サン酸アミドを触媒１ml当たり毎時0.40ｇ供給し
た。反応開始５時間後に生成物の補集を開始し、
２時間補集を続行した。生成物の分析結果は、未
反応５−オキソ−ヘキサン酸アミド 47重量％、
２−メチル−ピペリジノン−６ 42重量％、シク
ロヘキサン−１・３−ジオン３重量％であつた。 The catalyst bed was heated to 320 DEG C. and 0.40 g of 5-oxo-hexanoic acid amide was fed per ml of catalyst per hour. 5 hours after the start of the reaction, product collection was started,
Collection continued for 2 hours. Analysis of the product showed 47% by weight of unreacted 5-oxo-hexanoic acid amide;
The contents were 42% by weight of 2-methyl-piperidinone-6 and 3% by weight of cyclohexane-1,3-dione.
Claims (1)
を表わす）で示される、５−オキソ−ヘキサン酸
アミド類を脱水触媒に接触させることを特徴とす
る、一般式、 （式中、R1およびR2は、前記と同一の意味を表わ
す）で示されるメチルピペリジノン類の製造方
法。[Claims] 1 5-, represented by the general formula CH 3 -CO-CHR 1 -CH 2 -CHR 2 -CONH 2 (wherein R 1 and R 2 represent a hydrogen atom or a methyl group) General formula, characterized in that oxo-hexanoic acid amides are brought into contact with a dehydration catalyst, A method for producing methylpiperidinones represented by the formula (wherein R 1 and R 2 have the same meanings as above).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8901776A JPS5315384A (en) | 1976-07-28 | 1976-07-28 | Preparation of methylpiperazinones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8901776A JPS5315384A (en) | 1976-07-28 | 1976-07-28 | Preparation of methylpiperazinones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5315384A JPS5315384A (en) | 1978-02-13 |
| JPS6121946B2 true JPS6121946B2 (en) | 1986-05-29 |
Family
ID=13959129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8901776A Granted JPS5315384A (en) | 1976-07-28 | 1976-07-28 | Preparation of methylpiperazinones |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5315384A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02244200A (en) * | 1989-03-17 | 1990-09-28 | Akio Ogiwara | Pitch detecting circuit for processing voice signal |
| JP2856787B2 (en) * | 1989-10-27 | 1999-02-10 | 日本電気ホームエレクトロニクス株式会社 | Binarization circuit, intermediate level detection circuit, and peak envelope detection circuit |
-
1976
- 1976-07-28 JP JP8901776A patent/JPS5315384A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5315384A (en) | 1978-02-13 |
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