JPS6225131B2 - - Google Patents
Info
- Publication number
- JPS6225131B2 JPS6225131B2 JP54116652A JP11665279A JPS6225131B2 JP S6225131 B2 JPS6225131 B2 JP S6225131B2 JP 54116652 A JP54116652 A JP 54116652A JP 11665279 A JP11665279 A JP 11665279A JP S6225131 B2 JPS6225131 B2 JP S6225131B2
- Authority
- JP
- Japan
- Prior art keywords
- trichloroethane
- chloride
- vinylidene
- present
- trihaloethane
- 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
- -1 vinylidene halide Chemical class 0.000 claims description 14
- 150000007530 organic bases Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000012433 hydrogen halide Substances 0.000 claims description 5
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 5
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 24
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007822 coupling agent Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 2
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical group CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- UKDOTCFNLHHKOF-FGRDZWBJSA-N (z)-1-chloroprop-1-ene;(z)-1,2-dichloroethene Chemical group C\C=C/Cl.Cl\C=C/Cl UKDOTCFNLHHKOF-FGRDZWBJSA-N 0.000 description 1
- ZDUOUNIIAGIPSD-UHFFFAOYSA-N 1,1,1-tribromoethane Chemical compound CC(Br)(Br)Br ZDUOUNIIAGIPSD-UHFFFAOYSA-N 0.000 description 1
- QUMDOMSJJIFTCA-UHFFFAOYSA-N 1,1,2-tribromoethane Chemical compound BrCC(Br)Br QUMDOMSJJIFTCA-UHFFFAOYSA-N 0.000 description 1
- ANFXTILBDGTSEG-UHFFFAOYSA-N 1-methyl-4,5-dihydroimidazole Chemical compound CN1CCN=C1 ANFXTILBDGTSEG-UHFFFAOYSA-N 0.000 description 1
- SXZSFWHOSHAKMN-UHFFFAOYSA-N 2,3,4,4',5-Pentachlorobiphenyl Chemical compound C1=CC(Cl)=CC=C1C1=CC(Cl)=C(Cl)C(Cl)=C1Cl SXZSFWHOSHAKMN-UHFFFAOYSA-N 0.000 description 1
- LDZYRENCLPUXAX-UHFFFAOYSA-N 2-methyl-1h-benzimidazole Chemical group C1=CC=C2NC(C)=NC2=C1 LDZYRENCLPUXAX-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 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
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- 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[Detailed description of the invention] The present invention
【式】（たゞし、R1は−CH2− CH2−、−CH＝CH−、[Formula] (R 1 is −CH 2 − CH 2 −, −CH=CH−,
【式】のいず
れか、R2はＨあるいはCH3）なる構造を有する有
機塩基のハロゲン化水素塩の存在下でトリハロエ
タンを加熱してハロゲン化ビニリデンを製造する
方法に関する。
ハロゲン化ビニリデンは高分子合成用の単量体
あるいは合成中間体として有用である。
ハロゲン化ビニリデンは１・１・１−トリハロ
エタンあるいは１・１・２−トリハロエタンの脱
ハロゲン化水素反応により合成される。なかんづ
く、安価に製造できる１・１・２−トリハロエタ
ンの脱ハロゲン化水素反応による方法が多用され
ている。
１・１・２−トリクロロエタンの熱的脱塩化水
素反応により塩化ビニリデンが生成するが、同時
に、相当量の１・２−ジクロロエチレンが副生し
経済的でない。このさい、塩化セシウムなどのア
ルカリ金属塩化物を共存させることにより塩化ビ
ニリデンの選択的合成をする方法が特許出願され
ているが（日特開48−62706号）、事実上、高い選
択性を与えるのはアルカリ金属塩化物中塩化セシ
ウム含有触媒に限られる上、塩化セシウムが資源
的に希少かつ高価であるため工業的に利用されて
いない。
工業的には、たとえば、１・１・２−トリクロ
ロエタンより水酸化ナトリウムあるいは水酸化カ
ルシウムを脱ハロゲン化水素試薬として用いて塩
化ビニリデンを製造する方法が利用されている。
この方法の欠点は１・１・２−トリクロロエタン
から脱取した塩化水素は塩化ナトリウムあるいは
塩化カルシウムになり経済的に再利用出来ない事
と水酸化ナトリウムなどが化学量論的に消費され
る事にある。
本発明者らはハロゲン化ビニリデンの製法につ
いて鋭意検討を行つた結果、The present invention relates to a method for producing vinylidene halide by heating trihaloethane in the presence of a hydrogen halide salt of an organic base having a structure in which R 2 is H or CH 3 . Vinylidene halides are useful as monomers or synthetic intermediates for polymer synthesis. Vinylidene halide is synthesized by dehydrohalogenation reaction of 1,1,1-trihaloethane or 1,1,2-trihaloethane. Among these, a method based on a dehydrohalogenation reaction of 1,1,2-trihaloethane, which can be produced at low cost, is frequently used. Vinylidene chloride is produced by the thermal dehydrochlorination reaction of 1,1,2-trichloroethane, but at the same time, a considerable amount of 1,2-dichloroethylene is produced as a by-product, which is not economical. At this time, a patent application has been filed for a method for selectively synthesizing vinylidene chloride by coexisting an alkali metal chloride such as cesium chloride (Japanese Patent Application Laid-Open No. 48-62706), but this method actually provides high selectivity. This is limited to catalysts containing cesium chloride in alkali metal chlorides, and cesium chloride is not used industrially because it is a rare and expensive resource. Industrially, for example, a method for producing vinylidene chloride from 1,1,2-trichloroethane using sodium hydroxide or calcium hydroxide as a dehydrohalogenation reagent is used.
The disadvantages of this method are that the hydrogen chloride removed from 1,1,2-trichloroethane becomes sodium chloride or calcium chloride and cannot be economically reused, and that sodium hydroxide and other substances are consumed stoichiometrically. be. The present inventors conducted intensive studies on the manufacturing method of vinylidene halide, and as a result,
【式】（R1
は−CH2−CH2−、−CH＝CH−、
[Formula] (R 1 is −CH 2 −CH 2 −, −CH=CH−,
【式】のいずれか、R2はＨあるいは
CH3）なる構造を有する有機塩基のハロゲン化水
素塩の存在下でトリハロエタンを加熱してハロゲ
ン化ビニリデンを製造する方法を見出した。驚く
べき事には、トリハロエタンとして、１・１・２
−トリハロエタンを用いた場合でもハロゲン化ビ
ニリデンが選択性良く生成するのである。
本発明におけるWe have discovered a method for producing vinylidene halide by heating trihaloethane in the presence of a hydrogen halide salt of an organic base having a structure in which R 2 is H or CH 3 . Surprisingly, as trihaloethane, 1, 1, 2
Even when -trihaloethane is used, vinylidene halide is produced with good selectivity. In the present invention
【式】（ただし、R1は
−CH2−CH2−、−CH＝CH−、
[Formula] (where R 1 is −CH 2 −CH 2 −, −CH=CH−,
【式】のいずれか、R2はＨあるいは
CH3）なる構造を有する有機塩基とは２−イミダ
ゾリン、イミダゾール、ベンゾイミダゾール、メ
チル−２−イミダゾリン、メチルイミダゾール、
メチルベンゾイミダゾールであり、上述の有機塩
基のハロゲン化水素塩とは塩化水素塩、臭化水素
塩である。
本発明におけるトリハロエタンとは１・１・１
−トリクロロエタン、１・１・２−トリクロロエ
タン、１・１・１−トリブロモエタン、１・１・
２−トリブロモエタンなどである。
本発明においてハロゲン化ビニリデンとは塩化
ビニリデンあるいは臭化ビニリデンである。
本発明において、加熱温度は150℃ないし400℃
が好ましく、180℃ないし350℃がさらに好まし
く、230℃ないし320℃がもつとも好ましい。
本発明は加圧下、大気圧下、減圧下のいずれで
実施しても良い。
本発明は気相で実施するのが望ましい。
本発明において、An organic base having a structure of [Formula], R 2 is H or CH 3 ) is 2-imidazoline, imidazole, benzimidazole, methyl-2-imidazoline, methylimidazole,
It is methylbenzimidazole, and the above-mentioned hydrohalide salts of organic bases include hydrochloride and hydrobromide salts. What is trihaloethane in the present invention? 1.1.1
-Trichloroethane, 1,1,2-trichloroethane, 1,1,1-tribromoethane, 1,1,
2-tribromoethane and the like. In the present invention, vinylidene halide is vinylidene chloride or vinylidene bromide. In the present invention, the heating temperature is 150℃ to 400℃
is preferable, 180°C to 350°C is more preferable, and 230°C to 320°C is also preferable. The present invention may be carried out under increased pressure, atmospheric pressure, or reduced pressure. Preferably, the invention is practiced in the gas phase. In the present invention,
【式】（たゞし、R1
は−CH2−CH2−、−CH＝CH−、
[Formula] (R 1 is −CH 2 −CH 2 −, −CH=CH−,
【式】のいずれか、R2はＨあるいは
CH3）なる構造を有する有機塩基のハロゲン化水
素塩は担体に担持した方が望ましい。担体として
はシリカゲルが望ましい。担体に担持する方法と
しては担体に担持する方法として通常知られてい
る方法ならばどのような方法でも良いが、担体と
の間に化学結合が生成する方法が望ましい。その
さい、カツプリング剤を使用しても良い。担体と
してシリカを用いる場合、カツプリング剤を用い
る場合、シラン系カツプリング剤が望ましい。と
くにハロアルキルトリアルコキシシランが望まし
い。ハロアルキルトリアルコキシシランの一例を
あげるとγ−クロロプロピルトリメトキシシラン
がある。
本発明を実施する場合、不活性ガスが共存して
も良い。
本発明を実施する場合、ハロゲン化ビニールが
共存しても良い。ハロゲン化ビニールとは塩化ビ
ニールあるいは臭化ビニールである。
本発明の方法を例示すると、シリカゲルにハロ
アルキルトリアルコキシシランをカツプリング剤
として用いた担持したIt is preferable that a hydrogen halide salt of an organic base having a structure in which R 2 is H or CH 3 is supported on a carrier. Silica gel is preferred as the carrier. Any method commonly known as a method for supporting on a carrier may be used as a method for supporting on a carrier, but a method that generates a chemical bond with the carrier is preferable. At that time, a coupling agent may be used. When using silica as a carrier and when using a coupling agent, a silane-based coupling agent is preferable. Particularly desirable are haloalkyltrialkoxysilanes. An example of haloalkyltrialkoxysilane is γ-chloropropyltrimethoxysilane. When carrying out the present invention, an inert gas may coexist. When carrying out the present invention, vinyl halide may also be present. Vinyl halide is vinyl chloride or vinyl bromide. To illustrate the method of the present invention, a haloalkyltrialkoxysilane was supported on silica gel using a coupling agent.
【式】（たゞし、
R1−CH2−CH2−、−CH＝CH−、
[Formula] (R 1 −CH 2 −CH 2 −, −CH=CH−,
【式】のいずれか、R2はＨまたは
CH3）なる構造の有機塩基のハロゲン化水素塩の
存在下でトリハロエタンの蒸気を150℃ないし400
℃で加熱し、ハロゲン化ビニリデンを製造する方
法である。
実施例 １
イミダゾール塩酸塩をシラン化合物をカツプリ
ング剤として下記の方法でシリカゲルに担持し
た。
メタキシレン100mlにイミダゾール２ｇに再蒸
留した３−クロロプロピルトリメトキシシランを
加え、これに150℃であらかじめ乾燥したシリカ
ゲル10ｇを加え、約８時間リフラツクスしたの
ち、ベンゼンならびにアセトンで洗浄した。
実施例 ２
実施例１で調製したシリカゲル担持イミダゾー
ル塩酸塩10ｇをガラス製反応管に充填し、300℃
で１・１・２−トリクロロエタンを窒素で希釈し
た気体（１・１・２−トリクロロエタン３体積
％）を空間速度250Hr-1で送入した。送入した
１・１・２−トリクロロエタン当り85モル％の収
率で塩化ビニリデンが得られた。
実施例 ３
実施例１で調製した触媒を、300℃、0.05気
圧、空間速度50NTPl／触媒・Hrで１・１・２
−トリクロロエタンを送入した。送入した１・
１・２−トリクロロエタン当り79モル％の収率で
塩化ビニリデンが得られた。
実施例 ４
イミダゾール２ｇの代りに２−イミダゾリン２
ｇを用いた以外は実施例１と同様にして２−イミ
ダゾリン塩化水素塩−シリカ触媒を調製した。こ
の触媒20ｇをガラス製反応管に充填し、270℃で
１・１・２−トリクロロエタンを窒素で希釈した
気体（１・１・２−トリクロロエタン５体積％）
を空間速度200Hr-1で送入した。送入した１・
１・２−トリクロロエタン当り82モル％の収率で
塩化ビニリデンが得られた。
実施例 ５
イミダゾール２ｇの代りにベンゾイミダゾール
２ｇを用いた事ならびにリフラツクスを一昼夜に
わたつて行つた以外は実施例１と同様にしてベン
ゾイミダゾール塩化水素塩−シリカ触媒を調製し
た。この触媒20ｇをガラス製反応管に充填し、
320℃で１・１・２−トリクロロエタンを窒素で
希釈した気体（１・１・２−トリクロロエタン28
体積％）を空間速度400Hr-1で送入した。送入し
た１・１・２−トリクロロエタン当り78モル％の
収率で塩化ビニリデンが生成した。[Formula], R 2 is H or CH 3 ) In the presence of a hydrogen halide salt of an organic base, the vapor of trihaloethane is
This is a method for producing vinylidene halide by heating at ℃. Example 1 Imidazole hydrochloride was supported on silica gel using a silane compound as a coupling agent in the following manner. 3-chloropropyltrimethoxysilane redistilled with 2 g of imidazole was added to 100 ml of meta-xylene, and 10 g of silica gel previously dried at 150° C. was added thereto. After refluxing for about 8 hours, the mixture was washed with benzene and acetone. Example 2 10 g of silica gel-supported imidazole hydrochloride prepared in Example 1 was filled into a glass reaction tube and heated at 300°C.
A gas prepared by diluting 1,1,2-trichloroethane with nitrogen (3% by volume of 1,1,2-trichloroethane) was fed at a space velocity of 250 Hr -1 . Vinylidene chloride was obtained in a yield of 85 mol % based on the 1,1,2-trichloroethane fed. Example 3 The catalyst prepared in Example 1 was heated at 300°C, 0.05 atm, and a space velocity of 50 NTPl/catalyst/Hr at 1, 1, and 2
- Trichloroethane was introduced. Sent 1.
Vinylidene chloride was obtained in a yield of 79 mol% based on 1,2-trichloroethane. Example 4 2-imidazoline 2 instead of 2 g imidazole
A 2-imidazoline hydrogen chloride-silica catalyst was prepared in the same manner as in Example 1 except that g was used. 20g of this catalyst was packed into a glass reaction tube, and a gas prepared by diluting 1,1,2-trichloroethane with nitrogen (5% by volume of 1,1,2-trichloroethane) was heated at 270°C.
was sent at a space velocity of 200Hr -1 . Sent 1.
Vinylidene chloride was obtained in a yield of 82 mol% based on 1,2-trichloroethane. Example 5 A benzimidazole hydrogen chloride-silica catalyst was prepared in the same manner as in Example 1, except that 2 g of benzimidazole was used instead of 2 g of imidazole and the reflux was carried out over a day and night. Fill a glass reaction tube with 20g of this catalyst,
Gas obtained by diluting 1,1,2-trichloroethane with nitrogen at 320℃ (1,1,2-trichloroethane28
% by volume) at a space velocity of 400 Hr -1 . Vinylidene chloride was produced at a yield of 78 mol% based on the 1,1,2-trichloroethane fed.
Claims (1)
塩基のハロゲン化水素塩の存在下でトリハロエタ
ンを加熱してハロゲン化ビニリデンを製造する方
法。[Claims] 1 [Formula] (where R 1 is -CH 2 -CH 2 -, -CH=CH-, or [Formula], R 2 is H or CH 3 ) A method for producing vinylidene halide by heating trihaloethane in the presence of a hydrogen halide salt of an organic base.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11665279A JPS5640622A (en) | 1979-09-13 | 1979-09-13 | Procution of vinylidene halide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11665279A JPS5640622A (en) | 1979-09-13 | 1979-09-13 | Procution of vinylidene halide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5640622A JPS5640622A (en) | 1981-04-16 |
| JPS6225131B2 true JPS6225131B2 (en) | 1987-06-01 |
Family
ID=14692526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11665279A Granted JPS5640622A (en) | 1979-09-13 | 1979-09-13 | Procution of vinylidene halide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5640622A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6426111U (en) * | 1987-08-07 | 1989-02-14 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016528224A (en) * | 2013-08-01 | 2016-09-15 | ソルヴェイ（ソシエテ アノニム） | Process for dehydrohalogenation of halogenated organic non-polymeric compounds |
-
1979
- 1979-09-13 JP JP11665279A patent/JPS5640622A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6426111U (en) * | 1987-08-07 | 1989-02-14 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5640622A (en) | 1981-04-16 |
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