DE1900659C3 - Verfahren zur Herstellung von Tri chlormethan su lfenylchlorid - Google Patents
Verfahren zur Herstellung von Tri chlormethan su lfenylchloridInfo
- Publication number
- DE1900659C3 DE1900659C3 DE19691900659 DE1900659A DE1900659C3 DE 1900659 C3 DE1900659 C3 DE 1900659C3 DE 19691900659 DE19691900659 DE 19691900659 DE 1900659 A DE1900659 A DE 1900659A DE 1900659 C3 DE1900659 C3 DE 1900659C3
- Authority
- DE
- Germany
- Prior art keywords
- sulfur
- chlorine
- dichloride
- reaction
- carbon
- 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
- 238000000034 method Methods 0.000 title claims description 29
- RYFZYYUIAZYQLC-UHFFFAOYSA-N perchloromethyl mercaptan Chemical compound ClSC(Cl)(Cl)Cl RYFZYYUIAZYQLC-UHFFFAOYSA-N 0.000 title description 13
- 238000006243 chemical reaction Methods 0.000 claims description 41
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 37
- 239000000460 chlorine Substances 0.000 claims description 29
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 28
- 229910052801 chlorine Inorganic materials 0.000 claims description 28
- 238000005660 chlorination reaction Methods 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- DDCYYCUMAFYDDU-UHFFFAOYSA-N methyl thiohypochlorite Chemical compound CSCl DDCYYCUMAFYDDU-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 230000002101 lytic effect Effects 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 claims 1
- INCPMRSWRODNTN-UHFFFAOYSA-N trichloro-$l^{3}-chlorane Chemical compound ClCl(Cl)Cl INCPMRSWRODNTN-UHFFFAOYSA-N 0.000 claims 1
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 78
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 24
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 20
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical group ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 6
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- SWYHWRRXAKMZLK-UHFFFAOYSA-N chloromethyl thiohypochlorite Chemical compound ClCSCl SWYHWRRXAKMZLK-UHFFFAOYSA-N 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- -1 aliphatic ethers Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- MAHNFPMIPQKPPI-UHFFFAOYSA-N disulfur Chemical compound S=S MAHNFPMIPQKPPI-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-N 0.000 description 1
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 241000282376 Panthera tigris Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000028016 temperature homeostasis Effects 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- ZCPSWAFANXCCOT-UHFFFAOYSA-N trichloromethanesulfonyl chloride Chemical compound ClC(Cl)(Cl)S(Cl)(=O)=O ZCPSWAFANXCCOT-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/08—Sulfenic acids; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691900659 DE1900659C3 (de) | 1969-01-08 | 1969-01-08 | Verfahren zur Herstellung von Tri chlormethan su lfenylchlorid |
| NO487969A NO128820B (enrdf_load_stackoverflow) | 1969-01-08 | 1969-12-10 | |
| SE1713069A SE351629B (enrdf_load_stackoverflow) | 1969-01-08 | 1969-12-11 | |
| DK658169A DK125393B (da) | 1969-01-08 | 1969-12-12 | Fremgangsmåde til fremstilling af triklometansulfenylklorid. |
| GB6072269A GB1244898A (en) | 1969-01-08 | 1969-12-12 | Process for the preparation of trichloromethane sulphenyl chloride |
| FI365969A FI50118C (fi) | 1969-01-08 | 1969-12-17 | Menetelmä trikloorimetaanisulfenyylikloridin valmistamiseksi. |
| CH1890469A CH517716A (de) | 1969-01-08 | 1969-12-19 | Verfahren zur Herstellung von Trichlormethansulfenylchlorid |
| RO6192769A RO58248A (enrdf_load_stackoverflow) | 1969-01-08 | 1969-12-20 | |
| YU320269A YU32476B (en) | 1969-01-08 | 1969-12-22 | Postupak za dobivanje trihlormetansulfenilhlorida |
| BG013618A BG17555A3 (bg) | 1969-01-08 | 1969-12-25 | Метод за получаване на трихлор метансулфенилхлорид |
| IE173069A IE33907B1 (en) | 1969-01-08 | 1969-12-30 | Process for the preparation of trichloromethanesulphenyl chloride |
| BE743941D BE743941A (enrdf_load_stackoverflow) | 1969-01-08 | 1969-12-31 | |
| LU60140D LU60140A1 (enrdf_load_stackoverflow) | 1969-01-08 | 1970-01-06 | |
| NL7000150A NL7000150A (enrdf_load_stackoverflow) | 1969-01-08 | 1970-01-07 | |
| FR7000421A FR2031084A5 (enrdf_load_stackoverflow) | 1969-01-08 | 1970-01-07 | |
| ES375204A ES375204A1 (es) | 1969-01-08 | 1970-01-07 | Procedimiento para la preparacion de cloruro de tricloro-metansulfenilo. |
| PL13803570A PL80428B1 (enrdf_load_stackoverflow) | 1969-01-08 | 1970-01-07 | |
| AT15170A AT291957B (de) | 1969-01-08 | 1970-01-08 | Verfahren zur Herstellung von Trichlormethansulfenylchlorid |
| CS15770A CS157080B2 (enrdf_load_stackoverflow) | 1969-01-08 | 1970-01-08 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691900659 DE1900659C3 (de) | 1969-01-08 | 1969-01-08 | Verfahren zur Herstellung von Tri chlormethan su lfenylchlorid |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1900659A1 DE1900659A1 (de) | 1970-09-24 |
| DE1900659B2 DE1900659B2 (de) | 1973-09-06 |
| DE1900659C3 true DE1900659C3 (de) | 1974-04-04 |
Family
ID=5721887
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691900659 Expired DE1900659C3 (de) | 1969-01-08 | 1969-01-08 | Verfahren zur Herstellung von Tri chlormethan su lfenylchlorid |
Country Status (19)
-
1969
- 1969-01-08 DE DE19691900659 patent/DE1900659C3/de not_active Expired
- 1969-12-10 NO NO487969A patent/NO128820B/no unknown
- 1969-12-11 SE SE1713069A patent/SE351629B/xx unknown
- 1969-12-12 GB GB6072269A patent/GB1244898A/en not_active Expired
- 1969-12-12 DK DK658169A patent/DK125393B/da unknown
- 1969-12-17 FI FI365969A patent/FI50118C/fi active
- 1969-12-19 CH CH1890469A patent/CH517716A/de not_active IP Right Cessation
- 1969-12-20 RO RO6192769A patent/RO58248A/ro unknown
- 1969-12-22 YU YU320269A patent/YU32476B/xx unknown
- 1969-12-25 BG BG013618A patent/BG17555A3/xx unknown
- 1969-12-30 IE IE173069A patent/IE33907B1/xx unknown
- 1969-12-31 BE BE743941D patent/BE743941A/xx unknown
-
1970
- 1970-01-06 LU LU60140D patent/LU60140A1/xx unknown
- 1970-01-07 NL NL7000150A patent/NL7000150A/xx not_active Application Discontinuation
- 1970-01-07 ES ES375204A patent/ES375204A1/es not_active Expired
- 1970-01-07 PL PL13803570A patent/PL80428B1/xx unknown
- 1970-01-07 FR FR7000421A patent/FR2031084A5/fr not_active Expired
- 1970-01-08 CS CS15770A patent/CS157080B2/cs unknown
- 1970-01-08 AT AT15170A patent/AT291957B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CS157080B2 (enrdf_load_stackoverflow) | 1974-08-23 |
| BG17555A3 (bg) | 1973-11-10 |
| ES375204A1 (es) | 1972-03-01 |
| NL7000150A (enrdf_load_stackoverflow) | 1970-07-10 |
| FR2031084A5 (enrdf_load_stackoverflow) | 1970-11-13 |
| FI50118B (enrdf_load_stackoverflow) | 1975-09-01 |
| RO58248A (enrdf_load_stackoverflow) | 1975-09-15 |
| LU60140A1 (enrdf_load_stackoverflow) | 1970-03-06 |
| DE1900659A1 (de) | 1970-09-24 |
| IE33907B1 (en) | 1974-12-11 |
| DE1900659B2 (de) | 1973-09-06 |
| DK125393B (da) | 1973-02-12 |
| GB1244898A (en) | 1971-09-02 |
| YU32476B (en) | 1974-12-31 |
| IE33907L (en) | 1970-07-08 |
| SE351629B (enrdf_load_stackoverflow) | 1972-12-04 |
| PL80428B1 (enrdf_load_stackoverflow) | 1975-08-30 |
| CH517716A (de) | 1972-01-15 |
| FI50118C (fi) | 1975-12-10 |
| AT291957B (de) | 1971-08-10 |
| YU320269A (en) | 1974-06-30 |
| BE743941A (enrdf_load_stackoverflow) | 1970-05-28 |
| NO128820B (enrdf_load_stackoverflow) | 1974-01-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |