JPS6021127B2 - Method for producing bromotrichloromethane - Google Patents
Method for producing bromotrichloromethaneInfo
- Publication number
- JPS6021127B2 JPS6021127B2 JP12503976A JP12503976A JPS6021127B2 JP S6021127 B2 JPS6021127 B2 JP S6021127B2 JP 12503976 A JP12503976 A JP 12503976A JP 12503976 A JP12503976 A JP 12503976A JP S6021127 B2 JPS6021127 B2 JP S6021127B2
- Authority
- JP
- Japan
- Prior art keywords
- bromine
- chloroform
- reaction
- aqueous solution
- bromotrichloromethane
- 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
- XNNQFQFUQLJSQT-UHFFFAOYSA-N bromo(trichloro)methane Chemical compound ClC(Cl)(Cl)Br XNNQFQFUQLJSQT-UHFFFAOYSA-N 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 48
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 39
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 34
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 34
- 229910052794 bromium Inorganic materials 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000007864 aqueous solution Substances 0.000 claims description 18
- 239000003518 caustics Substances 0.000 claims description 15
- 239000003513 alkali Substances 0.000 claims description 13
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 238000010992 reflux Methods 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 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
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- IHUREIPXVFKEDT-UHFFFAOYSA-N dibromo(dichloro)methane Chemical compound ClC(Cl)(Br)Br IHUREIPXVFKEDT-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 本発明はプロモトリクロロメタンの製造方法に関する。[Detailed description of the invention] The present invention relates to a method for producing promotrichloromethane.
詳しくはアルカリ水溶液中でクロロホルムと臭素とを反
応せしめてプロモトリクロロメタンを製造する方法に関
する。従来よりプロモトリクロロメタンの製造方法とし
て、川クロロホルムと臭素とを３００一５００ｑｏの様
な高温度で気相反応させる方法、‘２’四塩化炭素をア
ルミニウム又は臭化アルミニウムの存在下で臭素化する
方法等が知られている。Specifically, the present invention relates to a method for producing bromotrichloromethane by reacting chloroform and bromine in an aqueous alkaline solution. Conventionally, methods for producing promotrichloromethane include a method in which chloroform and bromine are reacted in a gas phase at a high temperature of 300 to 500 qo, and bromination of '2' carbon tetrachloride in the presence of aluminum or aluminum bromide. Methods are known.
しかしながら、｛１’の方法はガラス製反応器、ガラス
ラィニング反応器等の如き特殊材質の反応器で反応を行
う必要があり、且つ高温反応であることから熟練した技
術を必要とし、また‘２）の方法は触媒の取扱いに充分
なる注意を必要とし、例えば臭化アルミニウムは湿気に
ふれると分解し、刺激臭の強い臭化水素酸を発生するこ
と、また反応終了後残存触媒を分解するが、その際臭化
水素酸が発生しやすいことなどにより熟練した技術を必
要とする。However, method {1' requires the reaction to be carried out in a reactor made of a special material such as a glass reactor or a glass-lined reactor, and is a high-temperature reaction, which requires skilled techniques. Method 2) requires great care when handling the catalyst; for example, aluminum bromide decomposes when exposed to moisture, generating hydrobromic acid with a strong pungent odor, and the remaining catalyst must be decomposed after the reaction is complete. However, this process requires skilled techniques because hydrobromic acid is likely to be generated.
本発明者は特殊な技術を必要とすることなく容易に且つ
安定にプロモトリクロロメタンを製造する方法について
鋭意研究した結果、特定濃度の苛性アルカリ水溶液を用
いて且つクロロホルムの還流条件下でクロロホルムと臭
素とを反応せしめると比較的低温で反応が進み且つ高収
率でプロモトリクロロメタンを製造することが出釆るこ
とを見出し、本発明に到達したものである。As a result of intensive research into a method for easily and stably producing bromotrichloromethane without requiring any special technology, the present inventor discovered that chloroform and bromine can be produced easily and stably without requiring any special technology. The present invention was achieved based on the discovery that the reaction proceeds at a relatively low temperature and bromotrichloromethane can be produced in high yield.
すなわち、本発明は
１ クロロホルムと臭素とを反応せしめてプロモトリク
。That is, the present invention provides 1. Promotoric by reacting chloroform and bromine.
ロメタンを製造するに際し、クロロホルムと苛性アルカ
リ１０〜３の重量％の水溶液との混合物に臭素を添加し
、次いで還流条件下で反応を行うことを特徴とするプロ
モトリクロロメタンの製造方法である。本発明において
用いられる苛性アルカリ水溶液としては、例えば苛性ソ
ーダ水溶液、苛性カリ水溶液等が挙げられるが、特に苛
性ソーダ水溶液が好ましい。This is a method for producing bromotrichloromethane, which is characterized in that bromine is added to a mixture of chloroform and an aqueous solution of 10 to 3% by weight of caustic alkali, and then the reaction is carried out under reflux conditions. Examples of the caustic alkali aqueous solution used in the present invention include a caustic soda aqueous solution and a caustic potassium aqueous solution, and a caustic soda aqueous solution is particularly preferred.
苛性カリ水溶液は苛性ソーダ水溶液に比してプロモトリ
クロロメタンの収率が低くなる傾向がある。苛性アルカ
リ水溶液の濃度は１０〜３０重量％、好ましくは１５〜
２５重量％、更に好ましくは２０〜２５重量％である。
１の重量％未満では目的物の収量が僅少になる。A caustic potassium aqueous solution tends to have a lower yield of bromotrichloromethane than a caustic soda aqueous solution. The concentration of the caustic aqueous solution is 10 to 30% by weight, preferably 15 to 30% by weight.
It is 25% by weight, more preferably 20-25% by weight.
If the amount is less than 1% by weight, the yield of the target product will be small.
また３の重量％を超えると目的物の収率が低くなり、か
っかかる高濃度の苛性アルカリ水溶液の取扱いには危険
を含むので好ましくない。２０〜２５重量％のアルカリ
水溶液を用いると、反応状態が更に良好となり、高い収
率で目的物を得ることができる。Moreover, if it exceeds 3% by weight, the yield of the target product will be low, and handling of such a highly concentrated caustic alkaline aqueous solution may be dangerous, which is not preferable. When a 20 to 25% by weight aqueous alkali solution is used, the reaction condition becomes even better and the desired product can be obtained in high yield.
苛性アルカリの使用量は、臭素に対し少なくとも２モル
倍量であり、またクロロホルムに対し１〜２モル倍量で
あることが好ましい。本発明において用いられるクロロ
ホルムの量は、臭素に対し当量以上、好ましくは過剰量
であるが、あまり過剰に用いてもその有利性は増大しな
い。The amount of caustic alkali to be used is at least 2 times the mole of bromine, and preferably 1 to 2 times the amount of chloroform. The amount of chloroform used in the present invention is at least equivalent to bromine, preferably in excess, but its advantage will not increase if it is used in excess.
好ましい量は臭素の１〜３モル倍量、殊に１〜２モル倍
量である。本発明においてはクロロホルムを苛性アルカ
リ水溶液中へ、好ましくは常温で洋加して混合する。A preferred amount is 1 to 3 moles, especially 1 to 2 moles of bromine. In the present invention, chloroform is mixed into an aqueous caustic solution, preferably at room temperature.
次いで苛性アルカリ水溶液とクロロホルムとの混合物を
加溢し、４０ｏｏ以上に保ちながら、臭素を滴下する。
これにより発熱反応がただちに始まり、還流冷却器での
クロロホルムの還流が起る。反応中の反応混合物の温度
は約６０ｑＣとなる。臭素の添加が終了した時の反応混
合物の色は通常赤褐色であるが、還流下に加熱反応を続
けていくと、脱色され無色になる。臭素の添加及びその
後の反応を１０００以下で行なう場合、反応混合物の赤
褐色は反応終了後も消えず、臭素の大部分は臭素酸ソー
ダに変化し、目的のプロモトリクロロメタンは殆んど得
られない。また、臭素を常温以下で添加したのち、クロ
ロホルム還流下に加温した場合、反応終了後反応混合物
の赤褐色の脱色は完全でなくて淡燈色乃至黄色までであ
り、臭素の消費は不完全となりまた臭素酸ソ−ダの生成
が認められ、目的物の収率は低くなる。従って、臭素添
加時の混合物の温度を４０ｏｏ以上に保つことが好まし
い。混合物の温度を４０ｑｏ以上に保つことにより反応
速度が遠くなり、目的物を容易に製造できる理由は明確
ではないが、臭素が苛性アルカリ水溶液と接触すると、
化学活性度の高い、不安定な次亜臭素酸アルカリを生成
し、これがただちにクロロホルムと反応して目的物のプ
ロモトリクロロメタンを生成する。他方次亜臭素酸アル
カリがクロロホルムと反応せずに、臭素酸アルカ川こ変
化すれば、早速目的物を生成しなくなると考えられる。
本発明の方法でクロロホルムと臭素とを反応させると、
ジプロモジクロロメタンあるいは四臭化メタンの様な高
度臭素化物も僅かではあるが生成する。これら創生物は
必要により分離することができる。本発明によればプロ
モトリクロロメタンを容易に且つ比較的低温で、高度の
技能を必要とすることなく製造することができる。Next, a mixture of an aqueous caustic solution and chloroform is flooded, and bromine is added dropwise while maintaining the mixture at 40 oo.
This immediately initiates an exothermic reaction and refluxes the chloroform in the reflux condenser. The temperature of the reaction mixture during the reaction will be approximately 60 qC. When the addition of bromine is completed, the color of the reaction mixture is usually reddish brown, but as the reaction is continued under reflux, it is decolored and becomes colorless. When the addition of bromine and the subsequent reaction are carried out at a temperature below 1000, the reddish-brown color of the reaction mixture does not disappear even after the reaction is completed, most of the bromine changes to sodium bromate, and the desired bromotrichloromethane is hardly obtained. . Furthermore, when bromine is added below room temperature and then heated under refluxing chloroform, the reddish-brown color of the reaction mixture after the reaction is not completely decolorized, and the color ranges from light yellow to yellow, and bromine consumption is incomplete. In addition, the production of sodium bromate was observed, resulting in a low yield of the target product. Therefore, it is preferable to maintain the temperature of the mixture at 40 oo or higher during bromine addition. It is not clear why keeping the temperature of the mixture above 40 qo slows down the reaction and makes it easier to produce the desired product, but when bromine comes into contact with an aqueous caustic solution,
It produces highly chemically active and unstable alkali hypobromite, which immediately reacts with chloroform to produce the target product, bromotrichloromethane. On the other hand, if the alkali hypobromite does not react with chloroform and changes to the alkali bromate, it is thought that the target product will no longer be produced.
When chloroform and bromine are reacted in the method of the present invention,
Highly brominated compounds such as dibromodichloromethane or tetrabrominated methane are also formed, albeit in small amounts. These created organisms can be separated if necessary. According to the present invention, bromotrichloromethane can be produced easily, at relatively low temperatures, and without requiring advanced skills.
また刺激臭のあるガス発生することもなく、作業環境が
良好に保たれる。かかるプロモトリクｏｏメタンは、例
えばビニルポリマーの重合開始剤として有用である。以
下、実施例を挙げて本発明を詳述する。実施例 １
・苛性ソーダ８０夕を水２４助けこ溶解し、得ら
れた苛性ソーダ水溶液を鷹拝しながら、クロロホルム１
８０夕を少量宛注加した。Furthermore, there is no generation of gas with an irritating odor, and a good working environment is maintained. Such promotoric methane is useful, for example, as a polymerization initiator for vinyl polymers. Hereinafter, the present invention will be explained in detail with reference to Examples. Example 1
・Dissolve 80 parts of caustic soda in 24 parts of water, and add 1 part of chloroform while pouring the resulting caustic soda aqueous solution.
A small amount of 80 yen was added.
得られた混合物を湯浴中で加温して、４０００になった
ら、臭素１６０夕を滴下した。反応混合物の温度はただ
ちに上昇し、還流冷却器による還流が始まり、臭素の添
加が終ったら、そのまま加温を続けた。反応混合物は最
初は赤褐色であったのが、臭素添加終了後、大体２〜３
時間で脱色し、無色になった。臭素添加終了後、５時間
加温を続けたのち、反応混合物を冷却し、下層の有機物
層を取出し、水洗して、塩化カルシウムで乾燥した。次
いで糟溜し、沸点１００〜１０６ｑｏの溜分、プロモト
リクロロメタン１３０夕を得た。実施例２〜４及び比較
例
苛性ソーダ８０夕を水に溶かして夫々８．１０，２０及
び３の重量％のアルカリ水溶液を調整し、これらにクロ
ロホルム１５０夕を注加し、加溢した。The resulting mixture was heated in a hot water bath, and when the temperature reached 4,000, 160 g of bromine was added dropwise. The temperature of the reaction mixture rose immediately, reflux began using the reflux condenser, and heating was continued once the bromine addition was complete. The reaction mixture was initially reddish-brown in color, but after the bromine addition was completed, the color changed to about 2-3.
It bleached over time and became colorless. After the addition of bromine was completed, heating was continued for 5 hours, and then the reaction mixture was cooled, and the lower organic layer was taken out, washed with water, and dried over calcium chloride. The mixture was then distilled to obtain 130 quarts of bromotrichloromethane, a fraction with a boiling point of 100 to 106 quarts. Examples 2 to 4 and Comparative Examples 80 g of caustic soda was dissolved in water to prepare aqueous alkali solutions of 8.10, 20 and 3 wt %, respectively, and 150 g of chloroform was added thereto to overflow.
４０ｑｏになったら、臭素１６０夕を滴下し、滴下終了
後、還流冷却器下に７時間加温を続けた。When the temperature reached 40 qo, 160 ml of bromine was added dropwise, and after the dropwise addition was completed, heating was continued for 7 hours under a reflux condenser.
反応終了後、放冷し、下層の有機物を分離し、亜硫酸ソ
ーダ水溶液中で未反応臭素を消去し、水洗したのち、塩
化カルシウムで乾燥し分溜した。沸点１００〜１０５ｑ
ｏの溜分、プロモトリクロロメタンを得た。第一表に苛
性ソーダ濃度、プロモトリクロロメタンの収量及び反応
終了時の未反応臭素の有無を示す。第一表苛性ソーダ８
重量％水溶液を用いた場合（比較例）、臭素の大半は禾
反応で残り、反応器内に臭素蒸気が充満し、反応混合物
は濃赤褐色を示した。After the reaction was completed, the organic matter in the lower layer was separated, unreacted bromine was eliminated in an aqueous solution of sodium sulfite, washed with water, dried over calcium chloride, and fractionated. Boiling point 100-105q
A fraction of o, bromotrichloromethane, was obtained. Table 1 shows the concentration of caustic soda, the yield of bromotrichloromethane, and the presence or absence of unreacted bromine at the end of the reaction. Table 1: Caustic soda 8
When a wt % aqueous solution was used (comparative example), most of the bromine remained in the reaction, the reactor was filled with bromine vapor, and the reaction mixture exhibited a deep reddish-brown color.
苛性ソーダ１の重量％水溶液を用いた場合、反応混合物
は濃赤燈色を示した。When a 1% by weight aqueous solution of caustic soda was used, the reaction mixture exhibited a deep red light color.
苛性ソーダ３の重量％水溶液を用いた場合、反応混合物
は寒色になり、未反応臭素は認められなかつたが、臭素
酸ソーダの結晶が多量認められた。When a wt % aqueous solution of caustic soda 3 was used, the reaction mixture became cold in color and no unreacted bromine was observed, but a large amount of sodium bromate crystals were observed.
実施例 ５苛性ソーダ８０夕を２４私水に溶解し、得ら
れた苛性ソーダ水溶液に夫々クロロホルム３６０夕，２
４０夕，１８０夕，１５０＃あるいは１２０夕を注加し
た。Example 5 80 g of caustic soda was dissolved in 24 g of private water, and 360 g of chloroform and 2 g of chloroform were added to the resulting caustic soda aqueous solution, respectively.
40 m, 180 m, 150 # or 120 m was added.
得られた混合物をそれぞれ濠裕上で加溢し、４０ｏｏに
なったら臭素１６０夕を滴下した。滴下終了後還流冷却
器下に７時間反応を行なった。反応終了後、実施例１に
示したと同様の方法で、有機物層を処理し、プロモトリ
クロロメタンを得た。第二表にクロロホルムの量と目的
物の収量を示す。筆 表
クロロホルム／臭素のモル比が１の場合、反応終了時に
未反応臭素の残存が見られた。Each of the obtained mixtures was flooded over a moat, and when the mixture reached 40 ml, 160 ml of bromine was added dropwise. After the dropwise addition was completed, the reaction was carried out for 7 hours under a reflux condenser. After the reaction was completed, the organic layer was treated in the same manner as shown in Example 1 to obtain bromotrichloromethane. Table 2 shows the amount of chloroform and the yield of the target product. When the molar ratio of chloroform/bromine was 1, unreacted bromine remained at the end of the reaction.
Claims (1)
ロロメタンを製造するに際し、クロロホルムと苛性アル
カリ１０〜３０重量％の水溶液との混合物に臭素を添加
し、次いで還流条件下で反応を行うことを特徴とするプ
ロモトリクロロメタンの製造方法。 ２ 臭素を添加するときに混合物を４０℃以上に保つこ
とを特徴とする特許請求の範囲第１項記載の製造方法。 ３ 苛性アルカリとクロロホルムとのモル比が２対１乃
至１対１であることを特徴とする特許請求の範囲第１項
記載の製造方法。４ クロロホルムと臭素とのモル比が
１対１乃至３対１であることを特徴とする特許請求の範
囲第１項記載の製造方法。 ５ 苛性アルカリ水溶液として苛性アルカリ１５〜２５
重量％の水溶液を用いることを特徴とする特許請求の範
囲第１項記載の製造方法。 ６ 苛性アルカリが苛性ソーダであることを特徴とする
特許請求の範囲第１項、第３項又は第５項記載の製造方
法。[Claims] 1. When producing bromotrichloromethane by reacting chloroform and bromine, bromine is added to a mixture of chloroform and a 10 to 30% by weight aqueous solution of caustic alkali, and then the reaction is carried out under reflux conditions. A method for producing promotrichloromethane, characterized in that: 2. The manufacturing method according to claim 1, characterized in that the mixture is kept at 40° C. or higher when adding bromine. 3. The manufacturing method according to claim 1, wherein the molar ratio of caustic alkali to chloroform is 2:1 to 1:1. 4. The manufacturing method according to claim 1, wherein the molar ratio of chloroform to bromine is 1:1 to 3:1. 5 Caustic alkali 15-25 as a caustic alkali aqueous solution
The method according to claim 1, characterized in that an aqueous solution of % by weight is used. 6. The manufacturing method according to claim 1, 3, or 5, wherein the caustic alkali is caustic soda.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12503976A JPS6021127B2 (en) | 1976-10-20 | 1976-10-20 | Method for producing bromotrichloromethane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12503976A JPS6021127B2 (en) | 1976-10-20 | 1976-10-20 | Method for producing bromotrichloromethane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5353602A JPS5353602A (en) | 1978-05-16 |
| JPS6021127B2 true JPS6021127B2 (en) | 1985-05-25 |
Family
ID=14900321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12503976A Expired JPS6021127B2 (en) | 1976-10-20 | 1976-10-20 | Method for producing bromotrichloromethane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6021127B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110431126B (en) * | 2017-03-20 | 2022-12-02 | 巴斯夫欧洲公司 | Method for preparing bromotrichloromethane |
-
1976
- 1976-10-20 JP JP12503976A patent/JPS6021127B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5353602A (en) | 1978-05-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Joyce et al. | Free radical-initiated reaction of ethylene with carbon tetrachloride | |
| Nield et al. | 31. Aromatic polyfluoro-compounds. Part I. The synthesis of aromatic polyfluoro-compounds from pentafluorobenzene | |
| US4051182A (en) | Process for the manufacture of α-chloropropionyl chloride | |
| JPS60237030A (en) | Manufacture of 1,2,3-trichloro-2-methyl-prone | |
| JPS59216843A (en) | Bromination for manufacturing decabromodiphenyl ether from diphenyl ether | |
| JPS6212212B2 (en) | ||
| JPS5879935A (en) | Manufacture of 1,1-dihalo-1,2,2,2- tetrafluoroethane | |
| JPS6055061B2 (en) | Method for producing 4-chlorobenzenesulfonyl chloride | |
| JPS6021127B2 (en) | Method for producing bromotrichloromethane | |
| JPS5933584B2 (en) | Substituted benzylnitrile derivatives | |
| HATCH et al. | Allylic Chlorides. XXVI. The 1-Chloro-2-heptenes and 1-Chloro-4, 4-dimethyl-2-pentenes | |
| US2218018A (en) | Manufacture of halogenated hydrocarbons | |
| US3293305A (en) | Polyfluorinated organic compounds | |
| US3729543A (en) | Process for preparing alkali-metal tetra-chloroferrate | |
| US2308419A (en) | Method of making aralkyl iodides and corresponding alcohols | |
| US2598646A (en) | Production of polychloroethenes | |
| JPS60115547A (en) | P-(halomethyl)phenyl ketone and its production | |
| EP0038052B1 (en) | Method for the preparation of cis-alkenyl bromide and acetate | |
| FLECK | Anhydrous ferric chloride as a rearrangement catalyst for some chlorinated diphenylethanes | |
| JP3932791B2 (en) | Method for producing vinylidene chloride | |
| US1738193A (en) | Method of making alkyl halides | |
| JPS63500241A (en) | flurbiprofen manufacturing method | |
| JPS5973592A (en) | Manufacture of decamethylcyclopentasiloxane | |
| JPH049790B2 (en) | ||
| EP0012512B1 (en) | A process for the production of 2-alkyl- or 2-alkenyl-4,6-diacetyl resorcinols; 2-allyl-4,6-diacetyl resorcinol |