JP3586308B2 - A method for producing an alkyl isothiocyanate. - Google Patents
A method for producing an alkyl isothiocyanate. Download PDFInfo
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- JP3586308B2 JP3586308B2 JP07997195A JP7997195A JP3586308B2 JP 3586308 B2 JP3586308 B2 JP 3586308B2 JP 07997195 A JP07997195 A JP 07997195A JP 7997195 A JP7997195 A JP 7997195A JP 3586308 B2 JP3586308 B2 JP 3586308B2
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- Prior art keywords
- alkyl
- producing
- alkyl isothiocyanate
- isothiocyanate
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- -1 alkyl isothiocyanate Chemical class 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 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
- 238000006243 chemical reaction Methods 0.000 description 11
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 10
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000002516 radical scavenger Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical compound CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 2
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000011002 quantification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【０００１】
【産業上の利用分野】
アルキルイソチオシアネ−トはチオ尿素合成の中間体、農薬或は抗生物質の修飾剤として有用な５位にメルカプト基を有するテトラゾ−ルの合成原料など有機合成上の有用な出発原料である。
【０００２】
【従来の技術】
従来、アルキルイソチオシアネ−トはＵ．Ｓ．Ｐ：３，９２３，８５２ 、Ｕ．Ｓ．Ｐ：４，７１３，４６７ に記載されているごとく、一般にアルキルジチオカルバメ−トを触媒の存在下に酸素酸化して得る方法の外、クロル炭酸メチルもしくはエチルと反応させて生成した中間体を熱分解する方法〔Ｏｒｇ．Ｓｙｎｔｈｅｓｉｓ Ｃｏｌ．Ｖｏｌ．ＩＩＩ，５９９（１９５５）、Ｂｐ．８９２，７９０（１９５９）、Ｇｐ．１，１７８，４２３（１９６４）、該化合物のチオ尿素を中間体として合成し、これに２分の１当量の硫酸を加え、熱分解する方法（Ｊ．Ａｍ．Ｃｈｅｍ．Ｓｏｃ．７９，３６８３−６（１９５７） 〕、過酸化水素で分解する方法〔Ｇｅｒ．Ｏｆｆｅｎ．２，１０５，４７３（１９７２） 〕、その外チオフォスゲンを使用する方法がある。〔Ｆｒ．１，５２８，２４９（１９６８）〕上記従来のアルキルイソチオシアネ−トの製造法は製造コストの問題、使用原料が猛毒であったり、排ガス処理に問題があるなど種々な問題点があった。
【０００３】
【発明が解決しようとする課題】
本発明はアルキルイソチオシアネ−トの合成において、環境に優しく、工程が単純で、かつ安価な製造コストを実現することを目的とするものである。
【０００４】
【課題を解決するための手段】
本発明におけるアルキルイソチオシアネ−トの製造において重要なことは、ジチオカルバミン酸からの硫化水素の脱離である。硫化水素の酸化工程を経ず、反応を容易にする溶媒、もしくは硫化水素の脱離を促す化合物（硫化水素捕捉剤）を添加することによってアルキルイソチオシアネ−トを得る方法を提供するものである。即ち、本発明は以下の通りである。
（１）アルキルジチオカルバミン酸を、メチルアクリレート、メチルメタクリレート、アクリロニトリル、アセトン、アセトニトリルおよびエチレンオキシドから選択される化合物で処理することを特徴とする、アルキルイソチオシアネ−トの製造法。
（２）アルキルジチオカルバミン酸のアルキル基の炭素数が１〜１０である、（１）記載のアルキルイソチオシアネ−トの製造法。
（３）アルキルジチオカルバミン酸のアルキル基がフェニル基で置換されており、かつ炭素鎖の２位以降に二重結合が含まれていてもよい、（１）又は（２）記載のアルキルイソチオシアネ−トの製造法。
（４）溶媒として、二硫化炭素、芳香族、ハロゲン系炭化水素又はエ−テル系炭化水素が使用される、（１）〜（３）のいずれかに記載のアルキルイソチオシアネ−トの製造法。
【０００５】
本発明にいう硫化水素捕捉剤とはカルボキシル基、ニトロ基、或はイミノ基のような電子吸引基が二重結合のα位に結合した、例えばメチルメタクリレ−トやアクリロニトリル等で代表されるアルケニル系化合物、カルボニル基などの電子吸引基がα位に結合したアセトンやアセトニトリルで代表されるカルボニル系化合物、硫化水素と反応して容易に開環反応を生ずるエチレンオキサイドで代表されるエポキシ系化合物、或はジシアンジアミドなとで、硫化水素脱離を可能にする化合物である。
【０００６】
本反応に使用される硫化水素捕捉剤の使用量は、脱離しようとする硫黄に対して等モルもしくはそれよりも過剰であることが好ましい。場合によっては溶剤として使用することもできる。
【０００７】
本反応において使用可能な溶媒としては、硫化水素捕捉剤を溶媒として使用する外、例えば二硫化炭素の外、塩化メチレン、クロロフォルム、四塩化炭素、１，２−ジクロロエタン等のハロゲン系炭化水素、ベンゼンやトルエン等の芳香族系炭化水素及びエチルエ−テルや１，２−ジメトキシエタン等のエ−テル系炭化水素が使用される。
【０００８】
本反応における反応温度は通常０〜５０℃、好ましくは２０〜３０℃である。
【０００９】
反応は回転数がモニタ−できる撹拌機、温度計、滴下ロ−トと冷却トラップがセットされた４つ口フラスコにメチルアミン水溶液、塩化メチレン及び生成物の同定及び定量を容易にするための内部標準試薬として既知量のペンタデカンを仕込み、氷冷、撹拌下室温で二硫化炭素を滴下、ジチオカルバミン酸を形成させ、メチルアクリレ−トなどの適量を添加し、一昼夜室温で撹拌を続けた。生成物はガスクロマトグラフィ−で分析し、ほぼ定量的に生成物を確認した。
【００１０】
次に実施例によって本発明を説明する。
【実施例１】
（メチルイソチオシアネ−トの調製）
回転数がモニタ−できる撹拌装置を準備し、５００ｍｌの４つ口フラスコにテフロン羽根を付けた撹拌棒、温度計、滴下ロ−トと冷却トラップをセットした。４０％のメチルアミン水溶液６５ｍｌ（０．７５ｍｏｌ） と塩化メチレン３００ｍｌ及び生成物の同定及び定量を容易にするための内部標準薬として既知量のペンタデカンをフラスコに仕込み３００ｒｐｍ で撹拌した。氷浴中、２０〜２５℃で二硫化炭素４１ｍｌ（０．６９ｍｏｌ） を約３０分で滴下し、系内の温度を２０〜２５℃に保ちながら、１時間熟成した後、メチルアクリレ−ト７５ｇを添加し、一昼夜その温度で撹拌を続けた。反応はガスクロマトグラフィ−でチェックし、内部標準試薬から収率を求めた。ほぼ定量的な収量が得られた。
【００１１】
【実施例２】
実施例１に従って次の生成物について反応を行った。その結果を以下に示す。
【実施例３】
実施例１に従ってメチルアクリレ−トの代わりにアクリロニトリル４０ｇ（０．７５ｍｏｌ） を添加し、同様の反応を行った。実施例１と同様ほぼ定量的なメチルイソチオシアネ−トが生成することを確認した。
【００１３】
【実施例４】
実施例３に従って次の生成物について反応を行った。その結果を以下に示す。
【実施例５】
実施例１に従ってメチルアクリレ−トの代わりにアセトン８７ｇ（０．７５ｍｏｌ） を添加し、同様の反応を行った。実施例１と同様ほぼ定量的なメチルイソチオシアネ−トが生成することを確認した。
【００１５】
【実施例６】
実施例５に従って次の生成物について反応を行った。その結果を以下に示す。
【発明の効果】
従来の合成方法は酸化もしくはチオフォスゲンなどの使用が必須であったが、硫化水素捕捉剤を導入することで温和な条件での反応が可能になり、アルキルイソチオシアネ−ト化の反応が可能になり、かつアルキルイソシアネ−ト類の収率が高い。[0001]
[Industrial applications]
Alkyl isothiocyanate is a useful starting material for organic synthesis such as an intermediate for the synthesis of thiourea, a raw material for the synthesis of tetrazole having a mercapto group at the 5-position which is useful as a modifier for pesticides or antibiotics.
[0002]
[Prior art]
Conventionally, alkyl isothiocyanates have been described in U.S. Pat. S. P: 3,923,852; S. As described in P: 713,467, in addition to a method generally obtained by oxidizing an alkyldithiocarbamate with oxygen in the presence of a catalyst, an intermediate produced by reacting with methyl or ethyl chlorocarbonate is used. Thermal decomposition method [Org. Synthesis Col. Vol. III, 599 (1955), Bp. 892,790 (1959), Gp. 1, 178, 423 (1964), a method of synthesizing the compound thiourea as an intermediate, adding a half equivalent of sulfuric acid thereto, and thermally decomposing (J. Am. Chem. Soc. 79, 3683-). 6 (1957)], a method of decomposing with hydrogen peroxide [Ger. Offen. 2, 105, 473 (1972)], and a method of using thiophosgene. [Fr. 1, 528, 249 (1968)] The above-mentioned conventional method for producing an alkyl isothiocyanate has various problems such as a problem of production cost, a toxic raw material used, and a problem of exhaust gas treatment.
[0003]
[Problems to be solved by the invention]
An object of the present invention is to realize an environment-friendly, simple process and low production cost in the synthesis of alkyl isothiocyanate.
[0004]
[Means for Solving the Problems]
What is important in the production of the alkyl isothiocyanate in the present invention is the elimination of hydrogen sulfide from dithiocarbamic acid. A method for obtaining an alkyl isothiocyanate by adding a solvent that facilitates the reaction or a compound that promotes elimination of hydrogen sulfide (hydrogen sulfide scavenger) without passing through a hydrogen sulfide oxidation step. is there. That is, the present invention is as follows.
(1) A method for producing alkyl isothiocyanate, comprising treating alkyl dithiocarbamic acid with a compound selected from methyl acrylate, methyl methacrylate, acrylonitrile, acetone, acetonitrile and ethylene oxide.
(2) The method for producing alkyl isothiocyanate according to (1), wherein the alkyl group of the alkyldithiocarbamic acid has 1 to 10 carbon atoms.
(3) The alkyl isothiocyanate according to (1) or (2), wherein the alkyl group of the alkyldithiocarbamic acid is substituted with a phenyl group, and a double bond may be contained at the second or subsequent position of the carbon chain. -A method of manufacturing
(4) The production of the alkyl isothiocyanate according to any one of (1) to (3), wherein a carbon disulfide, an aromatic, a halogen-based hydrocarbon or an ether-based hydrocarbon is used as a solvent. Law.
[0005]
The hydrogen sulfide scavenger referred to in the present invention is represented by, for example, methyl methacrylate or acrylonitrile in which an electron withdrawing group such as a carboxyl group, a nitro group or an imino group is bonded to the α-position of a double bond. Alkenyl compounds, carbonyl compounds such as acetone and acetonitrile in which an electron-withdrawing group such as a carbonyl group is bonded to the α-position, and epoxy compounds such as ethylene oxide, which easily react with hydrogen sulfide to cause a ring opening reaction Or dicyandiamide, which is a compound capable of eliminating hydrogen sulfide.
[0006]
The amount of the hydrogen sulfide scavenger used in this reaction is preferably an equimolar amount or an excess amount relative to the sulfur to be eliminated. In some cases, it can be used as a solvent.
[0007]
Examples of the solvent that can be used in this reaction include, in addition to using a hydrogen sulfide scavenger as a solvent, other than carbon disulfide, methylene chloride, chloroform, carbon tetrachloride, halogenated hydrocarbons such as 1,2-dichloroethane, and benzene. And aromatic hydrocarbons such as toluene and toluene, and ether hydrocarbons such as ethyl ether and 1,2-dimethoxyethane.
[0008]
The reaction temperature in this reaction is usually 0 to 50 ° C, preferably 20 to 30 ° C.
[0009]
The reaction is carried out in a four-necked flask equipped with a stirrer capable of monitoring the number of revolutions, a thermometer, a dropping funnel and a cooling trap, to facilitate the identification and quantification of methylamine aqueous solution, methylene chloride and products. A known amount of pentadecane was charged as a standard reagent, carbon disulfide was added dropwise at room temperature under ice-cooling and stirring to form dithiocarbamic acid, an appropriate amount of methyl acrylate was added, and stirring was continued at room temperature for 24 hours. The product was analyzed by gas chromatography, and the product was almost quantitatively confirmed.
[0010]
Next, the present invention will be described with reference to examples.
Embodiment 1
(Preparation of methyl isothiocyanate)
A stirrer capable of monitoring the number of rotations was prepared, and a stirring bar equipped with Teflon blades, a thermometer, a dropping funnel and a cooling trap were set in a 500 ml four-necked flask. A flask was charged with 65 ml (0.75 mol) of a 40% aqueous solution of methylamine, 300 ml of methylene chloride, and a known amount of pentadecane as an internal standard drug for facilitating identification and quantification of the product, and stirred at 300 rpm. In an ice bath, 41 ml (0.69 mol) of carbon disulfide was added dropwise at 20 to 25 ° C in about 30 minutes, and the mixture was aged for 1 hour while maintaining the temperature in the system at 20 to 25 ° C, and then 75 g of methyl acrylate was added. Addition and stirring continued at that temperature overnight. The reaction was checked by gas chromatography, and the yield was determined from an internal standard reagent. Nearly quantitative yields were obtained.
[0011]
Embodiment 2
The following products were reacted according to Example 1. The results are shown below.
Embodiment 3
According to Example 1, 40 g (0.75 mol) of acrylonitrile was added instead of methyl acrylate, and the same reaction was carried out. As in Example 1, it was confirmed that almost quantitative methyl isothiocyanate was produced.
[0013]
Embodiment 4
The following products were reacted according to Example 3. The results are shown below.
Embodiment 5
According to Example 1, 87 g (0.75 mol) of acetone was added instead of methyl acrylate, and the same reaction was carried out. As in Example 1, it was confirmed that almost quantitative methyl isothiocyanate was produced.
[0015]
Embodiment 6
The following products were reacted according to Example 5. The results are shown below.
【The invention's effect】
The conventional synthesis method required the use of oxidation or thiophosgene, but the introduction of a hydrogen sulfide scavenger makes it possible to perform the reaction under mild conditions, enabling the reaction of alkyl isothiocyanate formation. And the yield of alkyl isocyanates is high.
Claims (4)
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP07997195A JP3586308B2 (en) | 1995-03-09 | 1995-03-09 | A method for producing an alkyl isothiocyanate. |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP07997195A JP3586308B2 (en) | 1995-03-09 | 1995-03-09 | A method for producing an alkyl isothiocyanate. |
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| Publication Number | Publication Date |
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| JPH08245562A JPH08245562A (en) | 1996-09-24 |
| JP3586308B2 true JP3586308B2 (en) | 2004-11-10 |
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| JP07997195A Expired - Fee Related JP3586308B2 (en) | 1995-03-09 | 1995-03-09 | A method for producing an alkyl isothiocyanate. |
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| US6362374B1 (en) | 2000-05-01 | 2002-03-26 | The Lubrizol Corporation | Composition of and method for polysulfides having a reduced odor level |
| ITRM20130245A1 (en) * | 2013-04-24 | 2014-10-25 | Chimec Spa | NEW SCAVENGERS OF SULFIDRIC ACID |
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