DE1121607B - Verfahren zur Herstellung von unreinem und reinem Bis-(tetrachloraethyl)-disulfid - Google Patents
Verfahren zur Herstellung von unreinem und reinem Bis-(tetrachloraethyl)-disulfidInfo
- Publication number
- DE1121607B DE1121607B DEH38970A DEH0038970A DE1121607B DE 1121607 B DE1121607 B DE 1121607B DE H38970 A DEH38970 A DE H38970A DE H0038970 A DEH0038970 A DE H0038970A DE 1121607 B DE1121607 B DE 1121607B
- Authority
- DE
- Germany
- Prior art keywords
- disulfide
- bis
- tetrachloroethyl
- trichlorethylene
- impure
- 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
- SAPVRZJHCTUGIW-UHFFFAOYSA-N 1,1,1,2-tetrachloro-2-(1,2,2,2-tetrachloroethyldisulfanyl)ethane Chemical compound ClC(Cl)(Cl)C(Cl)SSC(Cl)C(Cl)(Cl)Cl SAPVRZJHCTUGIW-UHFFFAOYSA-N 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 15
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 239000000047 product Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- QLJHHMBKSLGTSQ-UHFFFAOYSA-N 1,1,2-trichloro-2-(1,2,2-trichloroethenyldisulfanyl)ethene Chemical compound ClC(Cl)=C(Cl)SSC(Cl)=C(Cl)Cl QLJHHMBKSLGTSQ-UHFFFAOYSA-N 0.000 description 1
- RUFAFKWLURMVKG-UHFFFAOYSA-N 1,2,2,2-tetrachloroethyl thiohypochlorite Chemical compound ClSC(Cl)C(Cl)(Cl)Cl RUFAFKWLURMVKG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229940095564 anhydrous calcium sulfate Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical compound CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- -1 trichlorovinyl Chemical group 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US800933A US3088818A (en) | 1959-03-23 | 1959-03-23 | Bis (tetrachloroethyl) disulfide |
| FR863060A FR79848E (fr) | 1959-03-23 | 1961-05-26 | Disulfure de bis |
| US278388A US3251884A (en) | 1959-03-23 | 1963-05-06 | Bis(haloalkyl)disulfides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1121607B true DE1121607B (de) | 1962-01-11 |
Family
ID=27246030
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEH38970A Pending DE1121607B (de) | 1959-03-23 | 1960-03-21 | Verfahren zur Herstellung von unreinem und reinem Bis-(tetrachloraethyl)-disulfid |
| DEH52559A Pending DE1226098B (de) | 1959-03-23 | 1964-04-30 | Verfahren zur Herstellung von Bis-(halogenalkyl)-disulfiden |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEH52559A Pending DE1226098B (de) | 1959-03-23 | 1964-04-30 | Verfahren zur Herstellung von Bis-(halogenalkyl)-disulfiden |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3251884A (en, 2012) |
| BE (2) | BE674970A (en, 2012) |
| DE (2) | DE1121607B (en, 2012) |
| FR (1) | FR79848E (en, 2012) |
| GB (2) | GB949374A (en, 2012) |
| NL (2) | NL6405072A (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1197877B (de) | 1959-09-26 | 1965-08-05 | Bayer Ag | Verfahren zur Herstellung von Polyhalogenalkansulfensaeurehalogeniden |
| US3251884A (en) * | 1959-03-23 | 1966-05-17 | Hooker Chemical Corp | Bis(haloalkyl)disulfides |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3484228A (en) * | 1968-06-03 | 1969-12-16 | Squibb & Sons Inc | Method of controlling weeds with dithiodianiline compounds |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2396788A (en) * | 1942-02-06 | 1946-03-19 | Du Pont | Reaction and products therefrom |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3088818A (en) * | 1959-03-23 | 1963-05-07 | Hooker Chemical Corp | Bis (tetrachloroethyl) disulfide |
| BE588646A (en, 2012) * | 1959-03-23 | 1960-07-01 |
-
0
- BE BE588646D patent/BE588646A/xx unknown
- NL NL249624D patent/NL249624A/xx unknown
-
1960
- 1960-03-18 GB GB9717/60A patent/GB949374A/en not_active Expired
- 1960-03-21 DE DEH38970A patent/DE1121607B/de active Pending
-
1961
- 1961-05-26 FR FR863060A patent/FR79848E/fr not_active Expired
-
1963
- 1963-05-06 US US278388A patent/US3251884A/en not_active Expired - Lifetime
-
1964
- 1964-04-30 DE DEH52559A patent/DE1226098B/de active Pending
- 1964-05-06 GB GB18893/64A patent/GB1068997A/en not_active Expired
- 1964-05-06 NL NL6405072A patent/NL6405072A/xx unknown
-
1966
- 1966-01-11 BE BE674970D patent/BE674970A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2396788A (en) * | 1942-02-06 | 1946-03-19 | Du Pont | Reaction and products therefrom |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3251884A (en) * | 1959-03-23 | 1966-05-17 | Hooker Chemical Corp | Bis(haloalkyl)disulfides |
| DE1197877B (de) | 1959-09-26 | 1965-08-05 | Bayer Ag | Verfahren zur Herstellung von Polyhalogenalkansulfensaeurehalogeniden |
Also Published As
| Publication number | Publication date |
|---|---|
| BE674970A (en, 2012) | 1966-05-03 |
| FR79848E (fr) | 1963-02-01 |
| DE1226098B (de) | 1966-10-06 |
| BE588646A (en, 2012) | 1960-07-01 |
| GB949374A (en) | 1964-02-12 |
| NL249624A (en, 2012) | |
| GB1068997A (en) | 1967-05-17 |
| NL6405072A (en, 2012) | 1964-11-09 |
| US3251884A (en) | 1966-05-17 |
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