JPH0674254B2 - Process for producing pyrazine derivative - Google Patents
Process for producing pyrazine derivativeInfo
- Publication number
- JPH0674254B2 JPH0674254B2 JP61138440A JP13844086A JPH0674254B2 JP H0674254 B2 JPH0674254 B2 JP H0674254B2 JP 61138440 A JP61138440 A JP 61138440A JP 13844086 A JP13844086 A JP 13844086A JP H0674254 B2 JPH0674254 B2 JP H0674254B2
- Authority
- JP
- Japan
- Prior art keywords
- zinc
- ammonia
- catalyst
- copper
- pyrazine derivative
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 8
- 150000003216 pyrazines Chemical class 0.000 title description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 16
- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052802 copper Inorganic materials 0.000 claims description 7
- 239000010949 copper Substances 0.000 claims description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- 239000011787 zinc oxide Substances 0.000 claims description 3
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 2
- 239000005751 Copper oxide Substances 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 229910000431 copper oxide Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- GFCDJPPBUCXJSC-UHFFFAOYSA-N [O-2].[Zn+2].[Cu]=O Chemical compound [O-2].[Zn+2].[Cu]=O GFCDJPPBUCXJSC-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- QDWOWLUANUBTGE-UHFFFAOYSA-N 2,6-Diethylpyrazine Chemical compound CCC1=CN=CC(CC)=N1 QDWOWLUANUBTGE-UHFFFAOYSA-N 0.000 description 2
- HJFZAYHYIWGLNL-UHFFFAOYSA-N 2,6-Dimethylpyrazine Chemical compound CC1=CN=CC(C)=N1 HJFZAYHYIWGLNL-UHFFFAOYSA-N 0.000 description 2
- -1 2-hydroxybutyl Chemical group 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical class C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 2
- 229940043276 diisopropanolamine Drugs 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000017 hydrogel Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- 239000001934 2,5-dimethylpyrazine Substances 0.000 description 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- GXDVEXJTVGRLNW-UHFFFAOYSA-N [Cr].[Cu] Chemical compound [Cr].[Cu] GXDVEXJTVGRLNW-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- 238000006210 cyclodehydration reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 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
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【発明の詳細な説明】 産業上の利用分野 本発明はピラジン誘導体の製造方法に関し、さらに詳し
くはジアルカノールアミン類とアンモニアを銅および／
または亜鉛を主要成分とする触媒の存在下、気相反応さ
せることによるピラジン誘導体の製造方法に関するもの
である。Description: TECHNICAL FIELD The present invention relates to a method for producing a pyrazine derivative, and more particularly, to a dialkanolamine and an ammonia in copper and / or
Alternatively, the present invention relates to a method for producing a pyrazine derivative by carrying out a gas phase reaction in the presence of a catalyst containing zinc as a main component.
従来技術と本発明が解決しようとする問題点 従来ピラジン類の製造方法としては、 （１）ピヘラジンの脱水素による方法（特開昭60−1694
68号公報）、（２）エチレングリコールのごときジオー
ル類とエチレンジアミンのごときジアミン類を原料とし
て脱水、脱水素する方法（特公昭55−50024号公報）、
（３）アルカノールアミンを環化脱水，脱水素する方法
（特開昭60−258168号公報）などが知られていたが、こ
れらの方法はいずれも２、６位に置換基を有するピラジ
ン類の合成法ではなく主として２位又は２、５位置換ピ
ラジン類の合成方法である。Problems to be Solved by the Prior Art and the Present Invention As a conventional method for producing pyrazines, (1) a method by dehydrogenation of piperazine (JP-A-60-1694
68), (2) a method of dehydrating and dehydrogenating diols such as ethylene glycol and diamines such as ethylenediamine as raw materials (Japanese Patent Publication No. 55-50024),
(3) Methods such as cyclodehydration and dehydrogenation of alkanolamines (JP-A-60-258168) have been known, but all of these methods are for the pyrazines having a substituent at the 2- and 6-positions. It is not a synthetic method but a synthetic method of mainly pyrazines substituted with 2-position or 2,5-position.
ピラジン誘導体は置換基の位置に関係なくほゞ同沸点を
有するために合成反応に於て位置異性体が生成しないよ
うにすることが重要であり、従来方法は２、６位に置換
基を有するピラジン誘導体の合成法とは言いがたかっ
た。そしてまた、ジアルコールをアンモニアを用いて環
化（ピラジン核）する方法は今までなかった。Since the pyrazine derivative has almost the same boiling point regardless of the position of the substituent, it is important to prevent the formation of positional isomers in the synthetic reaction, and the conventional method has a substituent at the 2- and 6-positions. It was hard to say that it was a method for synthesizing a pyrazine derivative. Also, there has been no method for cyclizing dialcohol (pyrazine nucleus) with ammonia.
問題点を解決するための手段 本発明者らは、これらの点について鋭意検討した結果、
ジアルカノールアミン類とアンモニアを反応させて２、
６位に置換基を有するピラジン誘導体の選択的合成法を
見出し、位置異性体を有しない製法を確立した。Means for Solving Problems As a result of diligent study on these points,
Reacting dialkanolamines with ammonia 2,
A selective synthesis method of a pyrazine derivative having a substituent at the 6-position was found, and a production method having no position isomer was established.
本発明は一般式 （式中Ｒはメチル、エチル又はフェニル基） で示されるジアルカノールアミン類とアンモニアを銅お
よび／または亜鉛を主要成分とする触媒の存在下、気相
接触反応せしめることを特徴とする一般式 （式中Ｒは前記と同じ） で示されるピラジン誘導体の製造方法に関するものであ
る。The present invention has the general formula (Wherein R is a methyl, ethyl or phenyl group) and a general formula characterized by subjecting a dialkanolamine and ammonia to a gas phase catalytic reaction in the presence of a catalyst containing copper and / or zinc as a main component. (In the formula, R is the same as above).
本発明に於いて触媒として用いる銅又は亜鉛としては、
銅または亜鉛を含む化合物であればよいが、酸化物が最
も好ましい。As copper or zinc used as a catalyst in the present invention,
A compound containing copper or zinc may be used, but an oxide is most preferable.
又他の金属化合物として例えばクロム，バリウム，カル
シウム，マンガン，スズ，ビスマス，トリウム，チタ
ン，アルミニウム，シリカ，などを含有してもよいが、
これらに限定されるものではない。銅および／または亜
鉛化合物を含有する触媒の特に好ましい具体例としては
酸化銅，酸化亜鉛，酸化銅−酸化亜鉛，銅−クロム，酸
化銅−酸化亜鉛などがあげられる。Further, other metal compounds such as chromium, barium, calcium, manganese, tin, bismuth, thorium, titanium, aluminum and silica may be contained,
It is not limited to these. Particularly preferred specific examples of the catalyst containing a copper and / or zinc compound include copper oxide, zinc oxide, copper oxide-zinc oxide, copper-chromium, copper oxide-zinc oxide and the like.
又該触媒は担体としてシリカ，シリカアルミナ，ゼオラ
イト，けいそう土，シリコンカーバイトなどを用いるこ
とも可能である。The catalyst can also use silica, silica-alumina, zeolite, diatomaceous earth, silicon carbide or the like as a carrier.
本発明に於ける反応温度は200℃乃至500℃であり、特に
250℃乃至450℃が好ましい。本発明のジアルカノールア
ミン類とアンモニアを反応させる際希釈剤として水，ベ
ンゼン，ピリジン，窒素，水素，などの反応に影響を及
ぼさない化合物を使用することが出来る。The reaction temperature in the present invention is 200 ° C to 500 ° C.
It is preferably 250 ° C to 450 ° C. When the dialkanolamines of the present invention are reacted with ammonia, compounds such as water, benzene, pyridine, nitrogen and hydrogen, which do not affect the reaction, can be used as a diluent.
本発明を実施するには、通常触媒を充填し、且つ所定の
反応温度に保持した固定床又は流動床反応器に原料ガス
を導入して触媒と接触させればよい。触媒との接触時間
も広範囲に変化させることが出来、空間速度は50乃至20
000Hr-1,好ましくは100乃至5000Hr-1である。In order to carry out the present invention, a raw material gas may be introduced into a fixed bed or fluidized bed reactor which is usually filled with a catalyst and kept at a predetermined reaction temperature and brought into contact with the catalyst. The contact time with the catalyst can be varied over a wide range, and the space velocity is 50 to 20.
It is 000 Hr -1 , preferably 100 to 5000 Hr -1 .
本発明で得られた反応物は常法に従って例えば蒸留等に
よって分離、精製が可能である。The reaction product obtained in the present invention can be separated and purified by a conventional method such as distillation.
実施例１ 硝酸亜鉛182gを含む水溶液と25％のアンモニア水83gと
混合しヒドロゲルを得た。得られた沈殿物をろ過，水洗
後11℃で乾燥し、400℃で４時間焼成して酸化亜鉛触媒
を得た。得られた触媒を内径12mmのパイレックス管反応
器に6g充填し400℃に保持して、ジイソプロパノールア
ミン3.0g/Hr、水3.0g/Hr、NH3/ジイソプロパノールアミ
ン＝10（モル比）で２時間通した。反応液を捕集しガス
クロマトグラフィーで分析したところ2,6−ジメチルピ
ラジンを収率32％で得た。Example 1 A hydrogel was obtained by mixing an aqueous solution containing 182 g of zinc nitrate with 83 g of 25% aqueous ammonia. The obtained precipitate was filtered, washed with water, dried at 11 ° C, and calcined at 400 ° C for 4 hours to obtain a zinc oxide catalyst. 6 g of the obtained catalyst was charged in a Pyrex tube reactor with an inner diameter of 12 mm and kept at 400 ° C., with diisopropanolamine 3.0 g / Hr, water 3.0 g / Hr, NH 3 / diisopropanolamine = 10 (molar ratio) I went for two hours. When the reaction solution was collected and analyzed by gas chromatography, 2,6-dimethylpyrazine was obtained in a yield of 32%.
実施例２ 硝酸銅46g、硝酸亜鉛128gを含む水溶液に約25％×アン
モニア水84gを加え、pH7としヒドロゲルを得た。得られ
た沈殿物を過，水洗後80℃で乾燥し、500℃で５時間
焼成して、酸化銅−酸化亜鉛触媒（重量比30:70）を得
た。この触媒5gを実施例１と同じ反応器に充填し350℃
に保持して、ビス（２−ハイドロオキシブチル）アミン
2.0g/Hr,水2.0g/Hr,アンモニア0.12モル/Hr,窒素0.02モ
ル/Hrで２時間流したところ、2,6−ジエチルピラジンを
収率35％で得た。Example 2 To an aqueous solution containing 46 g of copper nitrate and 128 g of zinc nitrate was added about 25% × ammonia water 84 g to adjust the pH to 7 to obtain a hydrogel. The obtained precipitate was washed with water, dried at 80 ° C, and calcined at 500 ° C for 5 hours to obtain a copper oxide-zinc oxide catalyst (weight ratio 30:70). 5 g of this catalyst was charged in the same reactor as in Example 1 and the temperature was 350 ° C.
Hold on bis (2-hydroxybutyl) amine
When 2.0 g / Hr, 2.0 g / Hr of water, 0.12 mol / Hr of ammonia and 0.02 mol / Hr of nitrogen were passed for 2 hours, 2,6-diethylpyrazine was obtained with a yield of 35%.
実施例３〜５ 実施例１と同一方法で下記に示す触媒を用いてＮ−（２
−フェニル−２−ヒドロキシエチル）イソプロパノール
アミン0.51g/Hr,アンモニア0.02モル/Hr,ベンゼン3g/Hr
の混合物を流したところ表−１の結果を得た。Examples 3 to 5 In the same manner as in Example 1, using a catalyst shown below, N- (2
-Phenyl-2-hydroxyethyl) isopropanolamine 0.51 g / Hr, ammonia 0.02 mol / Hr, benzene 3 g / Hr
When the mixture of above was run, the results shown in Table 1 were obtained.
Claims (2)
くとも銅および／または亜鉛を主要成分とする触媒の存
在下気相接触反応させることを特徴とする一般式 （式中Ｒは前記と同じ） で示されるピラジン誘導体の製造法1. A general formula (Wherein R represents a methyl, ethyl or phenyl group) and ammonia are subjected to a gas phase catalytic reaction in the presence of a catalyst containing ammonia and at least copper and / or zinc as a main component. General formula (Wherein R is the same as above)
媒が、酸化銅および／または酸化亜鉛を主要成分とする
触媒である特許請求の範囲第１項記載の方法2. The method according to claim 1, wherein the catalyst containing copper and / or zinc as a main component is a catalyst containing copper oxide and / or zinc oxide as a main component.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61138440A JPH0674254B2 (en) | 1986-06-13 | 1986-06-13 | Process for producing pyrazine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61138440A JPH0674254B2 (en) | 1986-06-13 | 1986-06-13 | Process for producing pyrazine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62294667A JPS62294667A (en) | 1987-12-22 |
| JPH0674254B2 true JPH0674254B2 (en) | 1994-09-21 |
Family
ID=15222038
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61138440A Expired - Lifetime JPH0674254B2 (en) | 1986-06-13 | 1986-06-13 | Process for producing pyrazine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0674254B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0186720U (en) * | 1987-11-30 | 1989-06-08 | ||
| US5304648A (en) * | 1992-09-29 | 1994-04-19 | Nestec S.A. | Pyrazine preparation |
| JP2002173486A (en) * | 2000-12-01 | 2002-06-21 | Koei Chem Co Ltd | Method for producing 2,6-di-substituted pyrazine |
| CN103949266B (en) * | 2014-05-15 | 2016-03-30 | 西安元创化工科技股份有限公司 | Take isopropanolamine as catalyst and the preparation method of Material synthesis 2,5-dimethyl pyrazine |
-
1986
- 1986-06-13 JP JP61138440A patent/JPH0674254B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62294667A (en) | 1987-12-22 |
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