JPH0513140B2 - - Google Patents
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- Publication number
- JPH0513140B2 JPH0513140B2 JP26915284A JP26915284A JPH0513140B2 JP H0513140 B2 JPH0513140 B2 JP H0513140B2 JP 26915284 A JP26915284 A JP 26915284A JP 26915284 A JP26915284 A JP 26915284A JP H0513140 B2 JPH0513140 B2 JP H0513140B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- parts
- aqueous solution
- general formula
- represented
- 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
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- 239000007864 aqueous solution Substances 0.000 claims description 13
- -1 acetylene compound Chemical class 0.000 claims description 12
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 150000007529 inorganic bases Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 239000002994 raw material Substances 0.000 description 6
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WBVOVRCGXKWAQT-UHFFFAOYSA-N 3,3-dichlorobutan-2-one Chemical compound CC(=O)C(C)(Cl)Cl WBVOVRCGXKWAQT-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- SNWBFNJXVNSVKM-UHFFFAOYSA-N 1,1-dichlorobutan-2-one Chemical compound CCC(=O)C(Cl)Cl SNWBFNJXVNSVKM-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005911 haloform reaction Methods 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明はジハロアルカノンの新規な製造法に関
し、さらに詳しくは、下記一般式〔〕で表わさ
れるアセチレン化合物から簡単な操作で効率よく
下記一般式〔〕で表わされるジハロアルカノン
を製造する方法に関する。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application Field) The present invention relates to a novel method for producing dihaloalkanones, and more specifically, the present invention relates to a novel method for producing dihaloalkanones. ] The present invention relates to a method for producing a dihaloalkanone represented by the following.
R1−Ｃ≡Ｃ−R2 ……〔〕
（式中、R1，R2は同種または異種の低級アル
キル基、Ｘはハロゲン原子を表わす。）
（従来の技術）
３，３−ジクロル−２−ブタノンに代表される
上記一般式〔〕で示される化合物は反応性に富
む有用な化合物で、例えば加水分解により食品添
加物や工業的原料として有用なビシナルジケトン
を容易に生成する。 R 1 −C≡C−R 2 …[] (In the formula, R 1 and R 2 are the same or different lower alkyl groups, and X represents a halogen atom.) (Prior art) In the above general formula [] represented by 3,3-dichloro-2-butanone, The compound shown is a highly reactive and useful compound, and for example, upon hydrolysis, it easily produces vicinal diketones useful as food additives and industrial raw materials.
かかるジハロアルカノンの製造法として、例え
ばアルカノンをハロゲン化する方法が考えられる
が、その場合にはハロホルム反応、開裂反応等が
生じ好ましい方法とは云いがたい。 As a method for producing such a dihaloalkanone, for example, a method of halogenating an alkanone can be considered, but in that case, a haloform reaction, a cleavage reaction, etc. occur, and it is difficult to say that this is a preferable method.
そこで本発明者らは新規な合成法を開発すべく
鋭意検討の結果、上記一般式〔〕で表わされる
アセチレン化合物を、出発物質とすることにより
一段で上記一般式〔〕で表わされるジハロアル
カノンを工業的に製造し得る方法を見出し、本発
明を完成するに到つた。 Therefore, as a result of intensive studies to develop a new synthetic method, the present inventors found that by using the acetylene compound represented by the above general formula [] as a starting material, the dihaloalkanone represented by the above general formula [] could be produced industrially in one step. The present inventors have discovered a method that can produce the same, and have completed the present invention.
（問題点を解決するための手段）
かくして本発明によれば、下記一般式〔〕で
表わされるアセチレン化合物を（Ａ）無機塩基の
水溶液中でハロゲンで酸化するか、または（Ｂ）
次亜ハロゲン酸化合物で酸化することを特徴とす
る下記一般式〔〕で表わされるジハロアルカノ
ンの製造法
R1−Ｃ≡Ｃ−R2 ……〔〕
（式中、R1，R2は同種または異種の低級アル
キル基、Ｘはハロゲン原子を表わす。）が提供さ
れる。(Means for Solving the Problems) Thus, according to the present invention, an acetylene compound represented by the following general formula [] is either (A) oxidized with a halogen in an aqueous solution of an inorganic base, or (B)
A method for producing a dihaloalkanone represented by the following general formula [], characterized by oxidation with a hypohalous acid compound R 1 -C≡C-R 2 ...[] (In the formula, R 1 and R 2 are the same or different lower alkyl groups, and X represents a halogen atom.)
さらに詳しく本発明の内容を述べると、上記一
般式〔〕で表わされるアセチレン化合物と無機
塩基の水溶液とから成る系にハロゲンを供給し、
該アセチレン化合物を酸化することにより、目的
とするジハロアルカノンが合成される。同様の結
果が得られる酸化剤としては次亜ハロゲン酸化合
物があり、上記一般式〔〕で表わされるアセチ
レン化合物と、次亜ハロゲン酸化合物の水溶液と
を接触させることによりジハロアルカノンを合成
することができる。 To describe the present invention in more detail, a halogen is supplied to a system consisting of an acetylene compound represented by the above general formula [] and an aqueous solution of an inorganic base,
By oxidizing the acetylene compound, the desired dihaloalkanone is synthesized. Hypohalous acid compounds are examples of oxidizing agents that can produce similar results, and dihaloalkanones can be synthesized by bringing the acetylene compound represented by the above general formula [] into contact with an aqueous solution of the hypohalous acid compound. .
原料として用いられるアセチレン化合物の具体
例としては、例えばブチン−２、ペンチン−２な
どが挙げられ、とくにブチン−２が賞用される。 Specific examples of the acetylene compound used as a raw material include butyne-2, pentyne-2, and the like, with butyne-2 being particularly preferred.
合成反応における反応温度は通常−10℃〜100
℃、好ましくは０〜50℃、反応圧力は0.5〜50気
圧、好ましくは１〜５気圧から選ばれ、原料とし
てのアセチレン化合物の沸点を勘案して適宜決定
される。原料としてのアセチレン化合物１モルを
基準とした場合、無機塩基の使用量は通常0.3〜
10モル、好ましくは0.6〜３モルであり、これを
溶解するのに必要な水を添加して無機塩基の水溶
液とするが、所要の水量は温度に応じて予め設定
することが可能であり、好ましくはやや過剰量の
水を加えて所望の水溶液を得ることができる。反
応の途上において経時的に無機塩類の析出を見る
ようなことがあつても反応にはとくに悪影響は見
られないが、攪拌等に操作上の支障が生じないよ
うにする必要がある。 The reaction temperature in the synthesis reaction is usually -10°C to 100°C.
The reaction pressure is selected from 0.5 to 50 atm, preferably 1 to 5 atm, and is appropriately determined in consideration of the boiling point of the acetylene compound as a raw material. The amount of inorganic base used is usually 0.3 to 1 mole of acetylene compound as a raw material.
10 mol, preferably 0.6 to 3 mol, and add the water necessary to dissolve this to make an aqueous solution of the inorganic base, but the required amount of water can be set in advance depending on the temperature, Preferably, a slight excess of water may be added to obtain the desired aqueous solution. Even if inorganic salts are deposited over time during the course of the reaction, no particular adverse effect will be observed on the reaction, but it is necessary to ensure that stirring and other operations are not hindered.
用いられる無機塩基の具体例としては、例えば
炭酸ナトリウム、炭酸カリウム、重炭酸ナトリウ
ム、重炭酸カリウムなどのごとき弱塩基、水酸化
リチウム、水酸化ナトリウム、水酸化カリウム、
水酸化カルシウム、水酸化マグネシウムなどのご
とき強塩基が例示され、なかでも反応性の点で弱
塩基、とくに炭酸塩または重炭酸塩が賞用され
る。 Specific examples of inorganic bases used include weak bases such as sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide,
Strong bases such as calcium hydroxide and magnesium hydroxide are exemplified, and weak bases, particularly carbonates or bicarbonates, are preferred from the viewpoint of reactivity.
酸化剤としてのハロゲン（例えば塩素、臭素な
ど）は、原料としてのアセチレン化合物１モルに
対して通常２モル以上を用いるが、その使用量の
上限は、未反応ハロゲンの後処理や多ハロゲン化
物の副生物の生成などの不利益を考慮して適宜限
定すればよい。 Halogen (for example, chlorine, bromine, etc.) as an oxidizing agent is usually used in an amount of 2 moles or more per 1 mole of the acetylene compound as a raw material, but the upper limit of its usage is limited to post-treatment of unreacted halogens and polyhalides. It may be appropriately limited in consideration of disadvantages such as generation of by-products.
酸化剤として次亜ハロゲン酸化合物（すなわち
次亜ハロゲン酸または次亜ハロゲン酸塩）を用い
る場合には、アセチレン化合物と次亜ハロゲン酸
化合物の水溶液を接触させることによつて反応が
行われる。次亜ハロゲン酸化合物の使用量は、通
常、アセチレン化合物１モルに対して２モル以上
である。 When a hypohalous acid compound (ie, hypohalous acid or a hypohalous acid salt) is used as an oxidizing agent, the reaction is carried out by bringing an acetylene compound into contact with an aqueous solution of the hypohalous acid compound. The amount of the hypohalous acid compound used is usually 2 mol or more per 1 mol of the acetylene compound.
反応用の装置としては、ハロゲン、次亜ハロゲ
ン酸及び次亜ハロゲン酸塩の水溶液に耐食性があ
ればよく、回分式、連続式、槽型、塔型等々の当
該分野で常用される形式のものであれば十分であ
る。 The reaction equipment may be of a type commonly used in the field, such as a batch type, continuous type, tank type, tower type, etc., as long as it has corrosion resistance for aqueous solutions of halogen, hypohalous acid, and hypohalite salts. It is sufficient.
（発明の効果）
かくして本発明によれば、前記一般式〔〕で
表わされるジハロアルカノンの合成に関し、極め
て容易で実用性のある方法が提供される。(Effects of the Invention) Thus, according to the present invention, an extremely easy and practical method for synthesizing the dihaloalkanone represented by the general formula [] is provided.
以下に実施例によつてさらに本発明の内容を説
明する。なお、実施例中の部数はとくに付言しな
い限り重量部を示す。 The content of the present invention will be further explained below using Examples. In addition, the number of parts in the examples indicates parts by weight unless otherwise specified.
実施例 １
ブチン−２，54部と炭酸ナトリウム水溶液1160
部（炭酸ナトリウム140部を含む）とを攪拌機つ
きの四つ口フラスコに入れ、氷浴中に浸し、内容
物の温度０℃の状態で攪拌しながら塩素ガスを
徐々に供給した。反応液のpHが次第に低下する
とともに炭酸ガスの発生が見られたので、これを
フラスコに付した冷却還流器を通して系外へ導き
放出した。Example 1 Butyne - 2.54 parts and sodium carbonate aqueous solution 1160 parts
(containing 140 parts of sodium carbonate) was placed in a four-necked flask equipped with a stirrer, immersed in an ice bath, and chlorine gas was gradually supplied while stirring the contents at 0°C. Since the pH of the reaction solution gradually decreased and the generation of carbon dioxide gas was observed, this gas was led out of the system through a cooling reflux device attached to the flask and released.
反応が進行するとともに不溶部分の析出が見ら
れるが、攪拌を継続し、系のpHが６〜７からさ
らに低下しようとする近辺で反応を停止した。 As the reaction progressed, precipitation of insoluble portions was observed, but stirring was continued and the reaction was stopped when the pH of the system was about to further decrease from 6 to 7.
反応液は、静置後、水相を除き、引続き水洗し
てから有機相を取り出して塩化カルシウムで乾燥
した。この有機相をガラス製精留装置（理論段７
段）で減圧下（100mmＨｇ）、還流比20で分留し、
初留は除いて52〜54℃の留分80.7部を得た。ガス
クロマトグラフにより分析した結果、この留分は
96％の３，３−ジクロルブタノンと１％の２，３
−ジクロルブテン−２及び高沸分３％から成るこ
とがわかり、仕込みブチン−２に対する３，３−
ジクロルブタノンの単離収率は55％であつた。 After the reaction solution was allowed to stand still, the aqueous phase was removed, the solution was washed with water, and the organic phase was taken out and dried over calcium chloride. This organic phase was removed using a glass rectifier (theoretical plate 7).
fractional distillation under reduced pressure (100 mmHg) at a reflux ratio of 20,
Excluding the first distillate, 80.7 parts of a fraction with a temperature of 52 to 54°C was obtained. As a result of analysis by gas chromatography, this fraction was
96% 3,3-dichlorobutanone and 1% 2,3
-dichlorobutene-2 and high-boiling content 3%, 3,3-
The isolated yield of dichlorobutanone was 55%.
実施例 ２
実施例１で用いた、炭酸ナトリウム水溶液にか
えて炭酸カリウム184部を含む水溶液1190部を用
いること以外は実施例１と同様にして反応を行
い、精留前の有機相を直接ガスクロマトグラフで
分析した結果、３，３−ジクロルブタノン−２の
収率はブチン−２に対して70％であつた。Example 2 The reaction was carried out in the same manner as in Example 1, except that 1190 parts of an aqueous solution containing 184 parts of potassium carbonate was used instead of the aqueous sodium carbonate solution used in Example 1, and the organic phase before rectification was directly subjected to gas chromatography. As a result of tograph analysis, the yield of 3,3-dichlorobutanone-2 was 70% based on butyne-2.
実施例 ３
実施例１で用いた炭酸ナトリウム水溶液にかえ
て、重炭酸ナトリウム水溶液1170部（重炭酸ナト
リウム170部を含む）を用いること以外は実施例
１と同様にして反応させ、精留前の有機相を分析
して３，３−ジクロルブタノン−２の収率を求め
たところ、原料ブチン−２に対して35％であつ
た。Example 3 The reaction was carried out in the same manner as in Example 1 except that 1170 parts of a sodium bicarbonate aqueous solution (containing 170 parts of sodium bicarbonate) was used in place of the sodium carbonate aqueous solution used in Example 1, and the reaction was carried out in the same manner as in Example 1. When the organic phase was analyzed to determine the yield of 3,3-dichlorobutanone-2, it was 35% based on the raw material butyne-2.
実施例 ４
ブチン−２ 54部と水200部を四つ口フラスコ
中で攪拌混合しながら、次亜塩素酸ナトリウム10
重量％の水溶液1510部を約４時間で逐次的に添加
した。反応系の温度は０℃〜５℃に保つた。反応
終了後、有機相をガスクロマトグラフで分析した
結果、３，３−ジクロルブタノンの収率は原料ブ
チン−２に対し48％であつた。Example 4 While stirring and mixing 54 parts of butyn-2 and 200 parts of water in a four-necked flask, 10 parts of sodium hypochlorite was added.
1510 parts of a % by weight aqueous solution were added sequentially over about 4 hours. The temperature of the reaction system was maintained at 0°C to 5°C. After the reaction was completed, the organic phase was analyzed by gas chromatography, and the yield of 3,3-dichlorobutanone was 48% based on the starting material butyne-2.
Claims (1)
合物を（Ａ）無機塩基の水溶液中でハロゲンで酸
化するか、または（Ｂ）次亜ハロゲン酸化合物で
酸化することを特徴とする下記一般式〔〕で表
わされるジハロアルカノンの製造法。 R1−Ｃ≡Ｃ−R2 ……〔〕 （式中、R1，R2は同種または異種の低級アル
キル基、Ｘはハロゲン原子を表わす。）[Claims] 1. An acetylene compound represented by the following general formula [] is (A) oxidized with a halogen in an aqueous solution of an inorganic base, or (B) oxidized with a hypohalous acid compound. A method for producing a dihaloalkanone represented by the following general formula []. R 1 −C≡C−R 2 …[] (In the formula, R 1 and R 2 represent the same or different lower alkyl groups, and X represents a halogen atom.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26915284A JPS61148137A (en) | 1984-12-20 | 1984-12-20 | Production of dihaloalkanone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26915284A JPS61148137A (en) | 1984-12-20 | 1984-12-20 | Production of dihaloalkanone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61148137A JPS61148137A (en) | 1986-07-05 |
| JPH0513140B2 true JPH0513140B2 (en) | 1993-02-19 |
Family
ID=17468398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26915284A Granted JPS61148137A (en) | 1984-12-20 | 1984-12-20 | Production of dihaloalkanone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61148137A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2916369A1 (en) | 2014-03-06 | 2015-09-09 | Mitsubishi Jidosha Kogyo Kabushiki Kaisha | Battery pack for electric vehicle |
-
1984
- 1984-12-20 JP JP26915284A patent/JPS61148137A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2916369A1 (en) | 2014-03-06 | 2015-09-09 | Mitsubishi Jidosha Kogyo Kabushiki Kaisha | Battery pack for electric vehicle |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61148137A (en) | 1986-07-05 |
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