DE1295549B - Verfahren zur Herstellung von C-bis C-Alkylrhodaniden - Google Patents
Verfahren zur Herstellung von C-bis C-AlkylrhodanidenInfo
- Publication number
- DE1295549B DE1295549B DE1966M0069135 DEM0069135A DE1295549B DE 1295549 B DE1295549 B DE 1295549B DE 1966M0069135 DE1966M0069135 DE 1966M0069135 DE M0069135 A DEM0069135 A DE M0069135A DE 1295549 B DE1295549 B DE 1295549B
- Authority
- DE
- Germany
- Prior art keywords
- rhodanide
- alkyl
- pressure
- methyl
- solution
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 5
- 125000000217 alkyl group Chemical group 0.000 title description 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 7
- 150000001348 alkyl chlorides Chemical class 0.000 claims description 6
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N anhydrous methyl chloride Natural products ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 15
- 229940050176 methyl chloride Drugs 0.000 description 15
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- VYHVQEYOFIYNJP-UHFFFAOYSA-N methyl thiocyanate Chemical compound CSC#N VYHVQEYOFIYNJP-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 5
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 4
- -1 alkyl methyl chloride Chemical compound 0.000 description 4
- 238000001256 steam distillation Methods 0.000 description 4
- 230000003213 activating effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- KKCSXNDFOBESIW-UHFFFAOYSA-N diazanium dithiocyanate Chemical compound [NH4+].[NH4+].[S-]C#N.[S-]C#N KKCSXNDFOBESIW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/02—Thiocyanates
- C07C331/04—Thiocyanates having sulfur atoms of thiocyanate groups bound to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Moulds For Moulding Plastics Or The Like (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45855965A | 1965-05-25 | 1965-05-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1295549B true DE1295549B (de) | 1969-05-22 |
Family
ID=23821248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1966M0069135 Pending DE1295549B (de) | 1965-05-25 | 1966-04-13 | Verfahren zur Herstellung von C-bis C-Alkylrhodaniden |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE679467A (enrdf_load_stackoverflow) |
| DE (1) | DE1295549B (enrdf_load_stackoverflow) |
| DK (1) | DK117487B (enrdf_load_stackoverflow) |
| GB (1) | GB1092598A (enrdf_load_stackoverflow) |
| LU (1) | LU50915A1 (enrdf_load_stackoverflow) |
| NL (1) | NL6604594A (enrdf_load_stackoverflow) |
| NO (1) | NO115798B (enrdf_load_stackoverflow) |
| SE (1) | SE327396B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114380725B (zh) * | 2021-12-16 | 2024-11-22 | 湖南海利化工股份有限公司 | 一种连续化合成甲基硫菌灵的方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1963100A (en) * | 1932-12-29 | 1934-06-19 | Grasselli Chemical Co | Lauryl thiocyanate |
-
1966
- 1966-03-24 GB GB1313666A patent/GB1092598A/en not_active Expired
- 1966-04-06 NL NL6604594A patent/NL6604594A/xx unknown
- 1966-04-13 BE BE679467D patent/BE679467A/xx unknown
- 1966-04-13 SE SE502466A patent/SE327396B/xx unknown
- 1966-04-13 DE DE1966M0069135 patent/DE1295549B/de active Pending
- 1966-04-16 NO NO16260466A patent/NO115798B/no unknown
- 1966-04-18 LU LU50915A patent/LU50915A1/xx unknown
- 1966-04-18 DK DK197266A patent/DK117487B/da unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1963100A (en) * | 1932-12-29 | 1934-06-19 | Grasselli Chemical Co | Lauryl thiocyanate |
Also Published As
| Publication number | Publication date |
|---|---|
| DK117487B (da) | 1970-05-04 |
| NO115798B (enrdf_load_stackoverflow) | 1968-12-09 |
| BE679467A (enrdf_load_stackoverflow) | 1966-10-13 |
| NL6604594A (enrdf_load_stackoverflow) | 1966-11-28 |
| LU50915A1 (enrdf_load_stackoverflow) | 1966-10-18 |
| SE327396B (enrdf_load_stackoverflow) | 1970-08-24 |
| GB1092598A (en) | 1967-11-29 |
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