JPS6018649B2 - Method for producing 2,2'-hydrazobis(2,4-dimethylvaleronitrile) - Google Patents
Method for producing 2,2'-hydrazobis(2,4-dimethylvaleronitrile)Info
- Publication number
- JPS6018649B2 JPS6018649B2 JP57182352A JP18235282A JPS6018649B2 JP S6018649 B2 JPS6018649 B2 JP S6018649B2 JP 57182352 A JP57182352 A JP 57182352A JP 18235282 A JP18235282 A JP 18235282A JP S6018649 B2 JPS6018649 B2 JP S6018649B2
- Authority
- JP
- Japan
- Prior art keywords
- melting point
- add
- compounds
- abvn
- dimethylvaleronitrile
- 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
- ZNHOHIPYRFCAPP-UHFFFAOYSA-N 2-[2-(2-cyano-4-methylpentan-2-yl)hydrazinyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)NNC(C)(C#N)CC(C)C ZNHOHIPYRFCAPP-UHFFFAOYSA-N 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000002844 melting Methods 0.000 description 24
- 230000008018 melting Effects 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 18
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000003505 polymerization initiator Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 5
- -1 2,2-hydrazobis(2,4-dimethylvaleronitrile) Chemical compound 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910052718 tin Inorganic materials 0.000 description 4
- 239000011135 tin Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- 101100537937 Caenorhabditis elegans arc-1 gene Proteins 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【発明の詳細な説明】
本発明はラジカル重合開始剤、発泡剤等として有用な２
，２′ーアゾビス（２，４−ジメチルワレロニトリル）
（以下ＡＢＶＮと略称する。DETAILED DESCRIPTION OF THE INVENTION The present invention provides two compounds useful as radical polymerization initiators, blowing agents, etc.
,2'-azobis(2,4-dimethylvaleronitrile)
(Hereinafter abbreviated as ABVN.
）の製造方法に係る。詳記すると、亜鉛、錫、鉄、銅、
アルミニウムから成る群から選ばれた金属塩の単独また
は混合の存在下にメチルイソブチルケトアチン（以下Ｍ
ＢＫＡと略称する。）とシアン化水素とを反応させて得
られた２，２ーヒドラゾビス（２，４ージメチルワレロ
ニトリル）（以下ＨＢＶＮと略称する。）をハロゲン等
で酸化し、低融点異性体に富むＡＢＶＮを得る製造方法
に関する。ＡＢＶＮは特に重合開始剤として、例えば塩
化ビニル、アクリロニトリル等の重合効率及び生成ポリ
マーの物体が他の重合開始剤と比べて遥かに勝れた性能
を有し、さらにビニル化合物全般にわたり例えば、エチ
レン、スチレン、アクリル酸ェステル、メタアクリル酸
ェステル、弗化ビニル、酢酸ビニル、アクリルアミド、
アクリル酸、メタアクリル酸、ビニルピリジンなどの有
効な重合開始剤として近来ますます重要性が高まってい
る。). In detail, zinc, tin, iron, copper,
Methylisobutylketoatine (hereinafter referred to as M
It is abbreviated as BKA. ) and hydrogen cyanide to oxidize 2,2-hydrazobis(2,4-dimethylvaleronitrile) (hereinafter abbreviated as HBVN) with halogen etc. to obtain ABVN rich in low-melting isomers. Regarding the method. ABVN has particularly superior performance as a polymerization initiator, such as vinyl chloride, acrylonitrile, etc., in terms of polymerization efficiency and produced polymer properties, compared to other polymerization initiators. Styrene, acrylate ester, methacrylate ester, vinyl fluoride, vinyl acetate, acrylamide,
It has recently become increasingly important as an effective polymerization initiator for acrylic acid, methacrylic acid, vinylpyridine, etc.
ところでＡＢＶＭよ、オーバーバーガ−（Ｃ．Ｇ．○〜
ｅｒｂｅｒｇｅｒ）、ジヤーナル オブ アメリ力ンケ
ミカル ソサイテイ（ＪｏｕｍａｌｏｆＡｍｅｒｉｃａ
ｎｃｈｅｍｉｃａｌＳｏｃｉｅｔｙ），第７鏡巻 ２６
１８頁の報告のある如く、融点５６ｑｏ〜５７午Ｃ、若
しくは７４ｑｏ〜７７０のメソ体若しくはｄｌ体なる立
体異性に起因する２種の異性体から成っており、分解速
度定数は低融点化合物Ｋ（ｓｅｃ‐１×１び）＝２．８
９（６９．９℃）、高融点化合物Ｋ（ｓｅｃ‐１×１び
）＝１．職（６９．８００）であり、通常公知の製法に
よっては繭＆真約４８℃〜６５つ○の、異性体の混合物
として提供される。ＡＢＶＮの低融点化合物、高融点化
合物の比率は経験的に融点幅により、又は赤外吸収スペ
クトル、核磁気共鳴スペクトル等の解析により測定され
る。By the way, ABVM, Oberburger (C.G.○~
erberger), Journal of America Chemical Society (JomalofAmerica)
nchemical Society), No. 7 Kagami Volume 26
As reported on page 18, it consists of two stereoisomers, the meso form and the dl form, with melting points of 56qo to 57°C and 74qo to 770°C, and the decomposition rate constant is that of the low melting point compound K ( sec-1×1bi)=2.8
9 (69.9°C), high melting point compound K (sec-1×1 second)=1. (69.800), and is usually provided as a mixture of isomers in cocoons and temperatures ranging from about 48°C to 65°C depending on known manufacturing methods. The ratio of low melting point compounds and high melting point compounds in ABVN is determined empirically by melting point width or by analysis of infrared absorption spectrum, nuclear magnetic resonance spectrum, etc.
例えば赤外吸収スペクトルでは波数７２０の‐１，７３
５肌‐１の吸収を比較すると、低融点化合物は７２０弧
‐１にシャープな吸収を有し、７３５の‐１は吸収がな
く、高藤点化合物はその逆である。さらに１対１の混合
物の場合は、７２０弧‐１と７３５肌‐１の吸収強度は
ほぼ１対１の比を示す。For example, in the infrared absorption spectrum, -1,73 at wave number 720
Comparing the absorption of 5 skin-1, the low melting point compound has sharp absorption at 720 arc-1, 735-1 has no absorption, and the opposite is true for Takafuji point compound. Furthermore, in the case of a 1:1 mixture, the absorption intensities of 720 Arc-1 and 735 Skin-1 show a nearly 1:1 ratio.
一方低融点化合物と、高融点化合物及び従釆の製法によ
る混合物の各種有機溶媒への溶解度を比較すると、低融
点化合物の溶解度は他に比して数情高く、特に低温時で
その差が顕著に現われる。それゆえに、低融点化合物に
富むＡＢＶＮを製造し得るなら、従釆の混合物により、
より重合性が高く且つ溶媒の選択に関し極めて有利なＡ
ＢＶＮを使用し得ることとなり、新しい重合開始剤を提
供するものとして重要である。本発明者等は上記の点に
留意し、鋭意研究の結果本発明を完成した。On the other hand, when comparing the solubility in various organic solvents of low melting point compounds, high melting point compounds, and mixtures produced by the secondary method, the solubility of low melting point compounds is numerically higher than that of other compounds, and the difference is especially noticeable at low temperatures. appears in Therefore, if ABVN rich in low melting point compounds can be produced, by a mixture of secondary
A has higher polymerizability and is extremely advantageous in terms of solvent selection.
This makes it possible to use BVN and is important as it provides a new polymerization initiator. The present inventors kept the above points in mind and completed the present invention as a result of intensive research.
本発明方法は公知の方法によりＭＢＫＡを製造し、亜鉛
、錫、銅、鉄、アルミニウムの塩酸塩、臭酸塩、及び硫
酸塩、硝酸塩、酢酸塩、シュウ酸塩等の酸塩の存在下好
ましくはフリーデルクラフッ触媒である。In the method of the present invention, MBKA is produced by a known method, preferably in the presence of an acid salt such as hydrochloride, bromate, sulfate, nitrate, acetate, or oxalate of zinc, tin, copper, iron, or aluminum. is a Friedel-Krauch catalyst.
亜鉛、錫、鉄、銅、アルミニウムの塩化物、臭化物のハ
ロゲン化物の存在下でシアン化水素と反応し、ＨＢＶＮ
を製造し、このような履歴をもつＨＢＶＮを出発原料と
して、これをハロゲン等で酸化して、低融点化合物に富
むＡＢＶＮを製造する。かかる出発原料のＨＢＶＮを得
る反応は通常、室温乃至４０℃で５〜１餌時間、亜鉛、
錫、銅、鉄、アルミニウムの塩はＭＢＫＡに対して０．
０５％〜３０％、好ましくは０．５〜１０％を単独また
は混合して使用される。Reacts with hydrogen cyanide in the presence of chlorides and bromides of zinc, tin, iron, copper, and aluminum, producing HBVN.
Using HBVN with such a history as a starting material, it is oxidized with halogen or the like to produce ABVN rich in low-melting compounds. The reaction to obtain such starting material HBVN is usually carried out at room temperature to 40°C for 5 to 1 feeding time, with zinc,
Salts of tin, copper, iron, and aluminum are 0.0% relative to MBKA.
05% to 30%, preferably 0.5 to 10%, alone or in combination.
シアン化水素は好ましくは無水状で反応するのがよい。
反応に使用される溶媒はＭ旧Ｋへ ＨＢＶＮ，およびシ
アン化水素に不活性なものであれば通常のものが支障な
く使用される。Hydrogen cyanide is preferably reacted in an anhydrous state.
As for the solvent used in the reaction, any ordinary solvent can be used without any problem as long as it is inert to M old K, HBVN, and hydrogen cyanide.
得られたＨＢＶＮの酸化反応は−２０℃〜３０ｑｏ、好
ましくは２ぴ０以下で、通常のＡＢＶＮの製造方法に従
って行えばよい。かかる方法によって製造されたＡＢＶ
ＮはＭＢＫＡからほぼ定量的に得られ、しかも重合活性
の高い又、溶解度の高い低融点化合物に富み、新規な重
合開始剤として提供され、斯界に貢献するところ大であ
る。The oxidation reaction of the obtained HBVN may be carried out at -20° C. to 30 qo, preferably at 2 p0 or less, according to a conventional method for producing ABVN. ABV produced by such a method
N can be obtained almost quantitatively from MBKA, and is rich in low-melting compounds with high polymerization activity and high solubility, and can be provided as a new polymerization initiator, making a great contribution to this field.
例えば、本発明の低融点化合物に富む重合開始剤はエチ
レン、スチレン、アクリル酸ェステル、塩化ビニル、酢
酸ビニル、アクリルアミド、アクリル酸、メタアクリル
酸、ビニルピリジン、不飽和ポリエステル等の重合開始
剤として有効に使用される。以下実施例を述べる。実施
例 １
ＭＢＫＡ５９夕に塩化亜鉛０．５夕を加え、蝿梓下、無
水状シアン化水素１７夕を水冷下１０ｑｏ〜３５ｏｏで
滴下し、１餌時間室温で放置反応させる。For example, the polymerization initiator rich in low melting point compounds of the present invention is effective as a polymerization initiator for ethylene, styrene, acrylate ester, vinyl chloride, vinyl acetate, acrylamide, acrylic acid, methacrylic acid, vinylpyridine, unsaturated polyester, etc. used for. Examples will be described below. Example 1 0.5 tons of zinc chloride is added to 59 tons of MBKA, 17 tons of anhydrous hydrogen cyanide is added dropwise under water cooling at 10 to 35 tons, and the mixture is left to react at room temperature for 1 hour.
反応物にメタノール１００Ｍを加え、縄梓下クロル２２
夕を氷袷下５００〜２０ｑ０で導入し、水を加えて、析
出するＡＢＶＮ７３．６夕を得る。Add 100M methanol to the reaction mixture, and add 22
Introduce 500 to 20 q0 q0 of water under the ice, add water, and obtain ABVN73.6 water that precipitates.
融点５６〜５８ｑｏ、含量９９．８％、ヒドラゾ含量０
．０５％、（低融点化合物約蝋％）。Melting point 56-58qo, content 99.8%, hydrazo content 0
．． 05% (approximately % wax of low melting point compounds).
実施例 ２
Ｍ旧ＫＡ５９夕に塩化第２錫１夕を加え、蝿梓下、無水
状シアン化水素１８夕を水冷下１０℃〜３５℃で滴下し
、８時間室温で放置反応させる。Example 2 One day of stannic chloride was added to M old KA59, and 18 hours of anhydrous hydrogen cyanide was added dropwise at 10°C to 35°C under water cooling, and the mixture was allowed to react at room temperature for 8 hours.
反応物にメタノール１００の【を加え、縄梓下プロム５
４夕を、氷冷下５℃〜２０℃で滴下し、水を加え析出す
るＡＢＶＮ７２．５夕を得る。Add 100% of methanol to the reaction mixture, and add 5% of methanol to the reactant.
ABVN72.5 was added dropwise under ice-cooling at 5°C to 20°C, and water was added to precipitate ABVN72.5.
融点５５〜５７℃、含量９９．５％、ヒドラゾ含量０．
１％（低融点化合物約９６％）。Melting point 55-57°C, content 99.5%, hydrazo content 0.
1% (approximately 96% low melting point compounds).
実施例 ３
ＭＢＫＡ５９夕に塩化アルミニウム２夕を加え、蝿梓下
、無水状シアン化水素１８夕を水冷下１ｏｏｏ〜３５℃
で反応させ１餌時間室温で放置反応させる。Example 3 Add aluminum chloride for 2 hours to MBKA59 hours, add 18 hours of anhydrous hydrogen cyanide under water cooling at 100 to 35°C.
Allow to react at room temperature for 1 hour.
反応物にメタノール１００の‘を加え、灘梓下クロル２
２夕を氷冷下５００〜２０℃で導入し、水を加えて、析
出するＡＢＶＮ７１．５夕を得る。融点５３ｑｏ〜６び
０、含量９９．５％、ヒドラゾ含量０．１％、（低融点
化合物約９３％）比較例
ＭＢＫＡ５９のこ鷹枠下、無水状シアン化水素２３夕を
水冷下１ｏｏｏ〜３ＦＣで滴下し、５餌時間室温で反応
させる。Add 100 parts of methanol to the reaction mixture and add 2 parts of Nada Azusa chlorine.
The mixture was introduced at 500 to 20° C. under ice cooling, and water was added to obtain precipitated ABVN71.5. Melting point 53qo~600, content 99.5%, hydrazo content 0.1%, (low melting point compound about 93%) Comparative example MBKA59 Under a saw frame, 23 hours of anhydrous hydrogen cyanide was added dropwise at 1ooo~3FC under water cooling. and react at room temperature for 5 hours.
反応物にメタノール１００私を加え、縄梓下クロル２２
夕を氷冷下５００〜２０ｑｏ導入し、水を加えて析出す
るＡＢＶＮ斑夕を得る。融点４３〜５がｏ、含量９９．
５％、ヒドラゾ含量０．１％（低融点化合物約５０％、
高融点化合物約５０％）実施例４〜１３実施例３に於け
る塩化アルミニウムの代りに各種金属塩類を用いて反応
を行い、処理して得られた結果を次表に示す。Add 100 parts of methanol to the reaction mixture, and add 22 parts of methanol to the reactant.
500 to 20 qo of ABVN powder is introduced under ice-cooling, and water is added to precipitate ABVN powder. Melting point 43-5 o, content 99.
5%, hydrazo content 0.1% (about 50% low melting point compounds,
High melting point compound (approximately 50%) Examples 4 to 13 Reactions were carried out using various metal salts in place of aluminum chloride in Example 3, and the results obtained are shown in the following table.
Claims (1)
ばれた金属の塩の単独または混合の存在下にメチルイソ
ブチルケトアチン（ＭＢＫＡ）とシアン化水素とを反応
させて２，２′−ヒドラゾビス（２，４−ジメチルワレ
ロニトリル）（ＨＢＶＮ）を製造する方法。1. 2,2'-Hydrazobis(2 , 4-dimethylvaleronitrile) (HBVN).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57182352A JPS6018649B2 (en) | 1982-10-18 | 1982-10-18 | Method for producing 2,2'-hydrazobis(2,4-dimethylvaleronitrile) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57182352A JPS6018649B2 (en) | 1982-10-18 | 1982-10-18 | Method for producing 2,2'-hydrazobis(2,4-dimethylvaleronitrile) |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50007640A Division JPS5811857B2 (en) | 1975-01-17 | 1975-01-17 | Azonitrile bag |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5877855A JPS5877855A (en) | 1983-05-11 |
| JPS6018649B2 true JPS6018649B2 (en) | 1985-05-11 |
Family
ID=16116805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57182352A Expired JPS6018649B2 (en) | 1982-10-18 | 1982-10-18 | Method for producing 2,2'-hydrazobis(2,4-dimethylvaleronitrile) |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6018649B2 (en) |
-
1982
- 1982-10-18 JP JP57182352A patent/JPS6018649B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5877855A (en) | 1983-05-11 |
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