JPH0337544B2 - - Google Patents
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- Publication number
- JPH0337544B2 JPH0337544B2 JP353383A JP353383A JPH0337544B2 JP H0337544 B2 JPH0337544 B2 JP H0337544B2 JP 353383 A JP353383 A JP 353383A JP 353383 A JP353383 A JP 353383A JP H0337544 B2 JPH0337544 B2 JP H0337544B2
- Authority
- JP
- Japan
- Prior art keywords
- ddm
- parts
- scf
- salt
- reaction
- 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
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- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 20
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical class N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 8
- DMDOIBWPFWJPQJ-ARJAWSKDSA-N (z)-2,3-bis(sulfanyl)but-2-enedinitrile Chemical compound N#CC(/S)=C(/S)C#N DMDOIBWPFWJPQJ-ARJAWSKDSA-N 0.000 claims description 7
- 150000008282 halocarbons Chemical class 0.000 claims description 6
- LIFQNDHZCABWSO-UHFFFAOYSA-N cyanomethanedithioic acid Chemical compound SC(=S)C#N LIFQNDHZCABWSO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- -1 alkali metal salt Chemical class 0.000 claims description 4
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 8
- 238000006477 desulfuration reaction Methods 0.000 description 6
- 230000023556 desulfurization Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 229940076442 9,10-anthraquinone Drugs 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 230000000447 dimerizing effect Effects 0.000 description 1
- PYZSVQVRHDXQSL-UHFFFAOYSA-N dithianon Chemical compound S1C(C#N)=C(C#N)SC2=C1C(=O)C1=CC=CC=C1C2=O PYZSVQVRHDXQSL-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
Description
【発明の詳細な説明】
本発明はジメルカプトマレオニトリルの塩を製
造する新規な方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a new process for producing salts of dimercaptomaleonitrile.
ジメルカプトマレオニトリルの塩（以下DDM
と略す）は、稲の白葉枯病、果樹あるいは野菜な
どの広範囲な病害に有効な殺菌剤として用いられ
ているジチアノン（２，３−ジシアノ−１，４−
ジチア−９，10−アンスラキノン）の原料として
使用される。DDMの製造法としては、(1)ジメチ
ルスルホオキシド（以下DMSOと略す）とシア
ノ化水素のアルカリ金属塩と二硫化炭素を反応さ
せて得られるシアノジチオ蟻酸のアルカリ金属塩
（以下SCFと略す）に、水を加えて脱硫反応を行
いDDMの水溶液として得る方法（E.Merck、特
公昭41−11730）、(2)シアン化ナトリウムと二硫化
炭素をジメチルホルムアマイド（以下DMFと略
す）中で反応させて得られるSCF・3DMFを減圧
下で加熱して脱硫反応を行つてDDMを単離する
方法（H.E.Simmonsら、J.Am.Chem.84，4756
（1962））、(3)シアン化ナトリウムと二硫化炭素を
アセトンと水の混合溶媒中で反応させてSCFを合
成し、水を加えて脱硫反応を行つてDDMを得る
方法（E.Ciganek and C.G.Krespan，J.Org.
Chem.，33，541（1968））、そして(4)シアン化ナト
リウムと二硫化炭素をアセトンとDMSOの混合
溶媒中で反応させてS.CFを合成した後、水を加
えてDDMを得る方法（山田頼信ら、特開昭57−
56453）が知られている。 Dimercaptomaleonitrile salt (DDM)
Dithianone (2,3-dicyano-1,4-
It is used as a raw material for dithia-9,10-anthraquinone). DDM is produced by (1) dimethyl sulfoxide (hereinafter referred to as DMSO), an alkali metal salt of hydrogen cyanide, and carbon disulfide, which is obtained by reacting an alkali metal salt of cyanodithioformic acid (hereinafter referred to as SCF); , A method of adding water to perform a desulfurization reaction to obtain an aqueous solution of DDM (E. Merck, Japanese Patent Publication No. 41-11730), (2) Reacting sodium cyanide and carbon disulfide in dimethylformamide (hereinafter abbreviated as DMF). A method of isolating DDM by heating the resulting SCF/3DMF under reduced pressure to perform a desulfurization reaction (HESimmons et al., J.Am.Chem. 84 , 4756
(1962)), (3) A method of synthesizing SCF by reacting sodium cyanide and carbon disulfide in a mixed solvent of acetone and water, and adding water to perform a desulfurization reaction to obtain DDM (E. Ciganek and CGKrespan, J.Org.
Chem., 33 , 541 (1968)), and (4) a method of synthesizing S.CF by reacting sodium cyanide and carbon disulfide in a mixed solvent of acetone and DMSO, and then adding water to obtain DDM. (Yorinobu Yamada et al., Japanese Unexamined Patent Publication No. 1983-
56453) is known.
これら四つの方法の中で(2)の方法以外は全て
DDMの水溶液という状態で反応に用いられてお
り、DMF、DMSOは水と任意に混じり合う高沸
点の溶媒のため回収が困難となり、工業的には非
常に不利となる。また(2)の方法ではDDMが固体
として単離出来るようであるが追試したところ満
足すべき結果を得ることが出来なかつた。これは
130℃という高温での脱硫反応となるため生成物
であるDDMが分解するということに起因するも
のと考えられる。そこでもつと温和な条件下で
DDMを単離出来ないかと鋭意検討した結果、
SCF・3DMFにクロロホルムなどを加えると脱硫
反応が起るという報告（G.Ba¨hr，Angew.
Chem.，68，525（1956））に着目し、工業的に有
利な条件を見出すことが出来、本発明を完成し
た。 Of these four methods, all except method (2)
DDM is used in the reaction in the form of an aqueous solution, and DMF and DMSO are high-boiling solvents that mix arbitrarily with water, making recovery difficult and extremely disadvantageous from an industrial perspective. In addition, method (2) seems to be able to isolate DDM as a solid, but additional tests failed to yield satisfactory results. this is
This is thought to be due to the fact that the product DDM decomposes because the desulfurization reaction occurs at a high temperature of 130°C. There, under mild conditions
As a result of intensive investigation into the possibility of isolating DDM,
It has been reported that a desulfurization reaction occurs when chloroform, etc. is added to SCF/3DMF (G.Ba¨hr, Angew.
Chem., 68 , 525 (1956)), they were able to find industrially advantageous conditions and completed the present invention.
本発明の方法は、シアン化水素塩と二硫化炭素
を反応させて得られるシアノジチオ蟻酸塩をその
10倍量以上のハロゲン化炭化水素中60〜120℃の
反応温度で二量化し次いで晶出した生成物を単離
することを特徴とするジメルカプトマレオニトリ
ルの塩の製造法に存する。 The method of the present invention uses cyanodithioformate obtained by reacting hydrogen cyanide with carbon disulfide.
The present invention relates to a process for producing a salt of dimercaptomaleonitrile, which comprises dimerizing in a halogenated hydrocarbon in an amount of 10 times or more at a reaction temperature of 60 to 120°C, and then isolating the crystallized product.
本発明の方法は、次に示される反応式に従つて
進行するものと考えられる（但し、NaCNを例と
して示す）。 It is believed that the method of the present invention proceeds according to the reaction formula shown below (however, NaCN is shown as an example).
従つて、本発明の方法においてSCFをCHCl3中
で二量化せしめる場合には、同時にSCRから硫
黄が脱離する反応が伴う。 Therefore, when SCF is dimerized in CHCl 3 in the method of the present invention, a reaction in which sulfur is eliminated from SCR is accompanied at the same time.
本発明の方法に用いるシアン化水素の塩は、ど
のようなアルカリ金属塩あるいはアンモニウム塩
を用いても良いけれども溶媒への溶解性、価格等
を考慮した場合、シアン化ナトリウムを用いるこ
とが好ましい。シアン化ナトリウムの粒径が反応
速度に大きな影響を与えるので、工業的には32メ
ツシユ通過の粒径のものを用いることが有利であ
る。SCFを生成する際の溶媒は、DMF、DMSO
などの非プロトン性の極性溶媒を使用することが
出来、DMSOを用いた場合には生成するSCFを
単離することが困難であるが、DMFを溶媒とし
て用いた場合には、SCF・3DMFの形で単離する
ことが出来る。どちらの方法でも良いがSCF・
3DMFの形で単離して脱硫反応を行つた方が生成
するDDMの純度と収率は優れている。 Although any alkali metal salt or ammonium salt may be used as the hydrogen cyanide salt used in the method of the present invention, it is preferable to use sodium cyanide in consideration of solubility in a solvent, cost, etc. Since the particle size of sodium cyanide has a great effect on the reaction rate, it is advantageous industrially to use a particle size that can pass through 32 meshes. The solvent for producing SCF is DMF, DMSO
When using DMSO, it is difficult to isolate the SCF produced, but when using DMF as a solvent, SCF/3DMF can be used. It can be isolated in the form Either method is fine, but SCF
The purity and yield of DDM produced is better when isolated in the form of 3DMF and subjected to desulfurization reaction.
本発明の方法に用いるSCFの二量化反応の際の
ハロゲン化炭化水素としては、一般にクロロホル
ム、四塩化エタン、クロルベンゼンなどの塩素化
炭化水素をあげることが出来るが、生成する
DDMの純度、収率を考慮した場合にはクロロホ
ルムを用いることが好ましい。溶媒量は用いる
SCFに対して10重量倍以上好ましくは10〜100重
量倍さらに好ましくは15〜30重量倍使用する。反
応温度は60〜120℃、好ましくは70〜100℃であ
る。 The halogenated hydrocarbons used in the dimerization reaction of SCF used in the method of the present invention generally include chlorinated hydrocarbons such as chloroform, tetrachloroethane, and chlorobenzene.
When considering the purity and yield of DDM, it is preferable to use chloroform. Use the amount of solvent
It is used at least 10 times the weight of SCF, preferably 10 to 100 times, and more preferably 15 to 30 times the weight. The reaction temperature is 60-120°C, preferably 70-100°C.
本発明の方法を実施するには、シアン化ナトリ
ウムと二硫化炭素を非プロトン性の極性溶媒中で
室温〜45℃で、２〜３時間反応させてSCFを合成
する。単離されたSCF・3DMFあるいは単離され
ていないSCFを含む溶液にクロロホルムを加え
て、60〜120℃で2.0〜10.0時間反応させる。反応
後析出したDDMをろ過して単離することが出来
る。 To carry out the method of the present invention, SCF is synthesized by reacting sodium cyanide and carbon disulfide in an aprotic polar solvent at room temperature to 45° C. for 2 to 3 hours. Chloroform is added to a solution containing isolated SCF/3DMF or unisolated SCF, and the mixture is reacted at 60 to 120°C for 2.0 to 10.0 hours. DDM precipitated after the reaction can be isolated by filtration.
次に本発明の方法を実施例をあげて説明する。
実施例において部は重量部を表わす。 Next, the method of the present invention will be explained by giving examples.
In the examples, parts represent parts by weight.
実施例 １
シアン化ナトリウム3.2部をDMSO15.6部に懸
濁させ、二硫化炭素5.0部を加え室温で0.5時間反
応させ、更に45℃で2.0時間反応させる。反応後
クロロホルム200部を加えて還流下で4.0時間反応
させた後析出した結晶をろ別することにより
DDM4.2部を単離することが出来た。収率は72.1
％であつた。Example 1 3.2 parts of sodium cyanide are suspended in 15.6 parts of DMSO, 5.0 parts of carbon disulfide is added, the mixture is reacted for 0.5 hours at room temperature, and further reacted for 2.0 hours at 45°C. After the reaction, 200 parts of chloroform was added and the reaction was carried out under reflux for 4.0 hours, and the precipitated crystals were filtered out.
We were able to isolate 4.2 parts of DDM. Yield is 72.1
It was %.
実施例 ２
シアン化ナトリウム3.2部をDMSO15.6部に懸
濁させ、二硫化炭素5.0部を加えて実施例１と同
様に反応させる。反応後クロロホルム300部を加
え、実施例１と同様様に処理する事により
DDM4.3部を得た。収率は73.0％であつた。Example 2 3.2 parts of sodium cyanide are suspended in 15.6 parts of DMSO, 5.0 parts of carbon disulfide is added, and the reaction is carried out in the same manner as in Example 1. After the reaction, 300 parts of chloroform was added and treated in the same manner as in Example 1.
I got 4.3 copies of DDM. The yield was 73.0%.
実施例 ３
SCF・3DMF21.6部をクロロホルム300部に溶
解させ、60℃で4.0時間反応させる。反応後ろ別
することにより4.55部のDDMを得た。収率は
79.7％であつた。Example 3 21.6 parts of SCF/3DMF is dissolved in 300 parts of chloroform and reacted at 60°C for 4.0 hours. After reaction and separation, 4.55 parts of DDM were obtained. The yield is
It was 79.7%.
実施例 ４
SCF・3DMF21.6部をクロロホルム200部に溶
解させ、69℃で4.0時間反応させることにより
DDM4.51部を得た。収率：80.9％。Example 4 By dissolving 21.6 parts of SCF/3DMF in 200 parts of chloroform and reacting at 69°C for 4.0 hours.
Got 4.51 copies of DDM. Yield: 80.9%.
実施例 ５
SCR・3DMF21.6部をクロロホルム300部に溶
解させ、72℃で4.0時間反応させることにより
DDM4.9部を得た。収率は87.1％であつた。Example 5 By dissolving 21.6 parts of SCR/3DMF in 300 parts of chloroform and reacting at 72°C for 4.0 hours,
I got 4.9 copies of DDM. The yield was 87.1%.
実施例 ６
SCF・3DMF21.6部をクロロホルム300部に溶
解させ、85℃で4.0時間反応させることにより
DDM5.6部を得た。収率は99％であつた。Example 6 By dissolving 21.6 parts of SCF/3DMF in 300 parts of chloroform and reacting at 85°C for 4.0 hours,
Obtained 5.6 copies of DDM. The yield was 99%.
Claims (1)
られるシアノジチオ蟻酸塩をその10倍量以上のハ
ロゲン化炭化水素の存在下、60〜120℃の反応温
度で二量化し、次いで晶出した生成物を単離する
ことを特徴とするジメルカプトマレオニトリルの
塩の製造法。 ２ シアン化水素塩がアルカリ金属塩又はアンモ
ニウム塩である特許請求の範囲第１項記載の方
法。 ３ シアン化水素塩がアン化ナトリウムである特
許請求の範囲第１項記載の方法。 ４ ハロゲン化炭化水素が塩素化炭化水素である
特許請求の範囲第１項記載の方法。 ５ 塩素化炭化水素がクロロホルムである特許請
求の範囲第４項記載の方法。 ６ ハロゲン化炭化水素の使用量がシアノジチオ
蟻酸塩の10〜100重量倍である特許請求の範囲第
１項記載の方法。 ７ ハロゲン化炭化水素の使用量がシアノジチオ
蟻酸塩の15〜30重量倍である特許請求の範囲第１
項記載の方法。 ８ 反応温度が70〜100℃である特許請求の範囲
第１項記載の方法。[Claims] 1. A cyanodithioformate obtained by reacting a hydrogen cyanide salt with carbon disulfide is dimerized at a reaction temperature of 60 to 120°C in the presence of a halogenated hydrocarbon in an amount of 10 times or more, and then A method for producing a salt of dimercaptomaleonitrile, which comprises isolating a crystallized product. 2. The method according to claim 1, wherein the hydrogen cyanide salt is an alkali metal salt or an ammonium salt. 3. The method according to claim 1, wherein the hydrogen cyanide salt is sodium anide. 4. The method according to claim 1, wherein the halogenated hydrocarbon is a chlorinated hydrocarbon. 5. The method according to claim 4, wherein the chlorinated hydrocarbon is chloroform. 6. The method according to claim 1, wherein the amount of halogenated hydrocarbon used is 10 to 100 times the weight of the cyanodithioformate. 7 Claim 1 in which the amount of halogenated hydrocarbon used is 15 to 30 times the weight of cyanodithioformate
The method described in section. 8. The method according to claim 1, wherein the reaction temperature is 70 to 100°C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP353383A JPS59130265A (en) | 1983-01-14 | 1983-01-14 | Preparation of salt of dimercaptomaleonitrile |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP353383A JPS59130265A (en) | 1983-01-14 | 1983-01-14 | Preparation of salt of dimercaptomaleonitrile |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59130265A JPS59130265A (en) | 1984-07-26 |
| JPH0337544B2 true JPH0337544B2 (en) | 1991-06-05 |
Family
ID=11560028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP353383A Granted JPS59130265A (en) | 1983-01-14 | 1983-01-14 | Preparation of salt of dimercaptomaleonitrile |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59130265A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115109029A (en) * | 2022-07-07 | 2022-09-27 | 浙江禾本科技股份有限公司 | Preparation method of dithianon |
-
1983
- 1983-01-14 JP JP353383A patent/JPS59130265A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59130265A (en) | 1984-07-26 |
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