CA1064508A - Chlorination of butadiene sulfone to 3,3,4,4-tetrachlorotetrahydrothiophene-1,1-dioxide - Google Patents
Chlorination of butadiene sulfone to 3,3,4,4-tetrachlorotetrahydrothiophene-1,1-dioxideInfo
- Publication number
- CA1064508A CA1064508A CA253,059A CA253059A CA1064508A CA 1064508 A CA1064508 A CA 1064508A CA 253059 A CA253059 A CA 253059A CA 1064508 A CA1064508 A CA 1064508A
- Authority
- CA
- Canada
- Prior art keywords
- dioxide
- chlorination
- catalyst
- reaction
- product
- 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
- 238000005660 chlorination reaction Methods 0.000 title claims abstract description 34
- MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical compound O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 title claims abstract description 10
- GCAXGCSCRRVVLF-UHFFFAOYSA-N 3,3,4,4-tetrachlorothiolane 1,1-dioxide Chemical compound ClC1(Cl)CS(=O)(=O)CC1(Cl)Cl GCAXGCSCRRVVLF-UHFFFAOYSA-N 0.000 title claims abstract 7
- 239000003054 catalyst Substances 0.000 claims abstract description 27
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 29
- 239000000460 chlorine Substances 0.000 claims description 26
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- 239000000047 product Substances 0.000 claims description 23
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 6
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 6
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 6
- -1 peroxy compound Chemical class 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- MKTOIPPVFPJEQO-UHFFFAOYSA-N 4-(3-carboxypropanoylperoxy)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OOC(=O)CCC(O)=O MKTOIPPVFPJEQO-UHFFFAOYSA-N 0.000 claims description 4
- 125000000864 peroxy group Chemical group O(O*)* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000001451 organic peroxides Chemical class 0.000 claims description 2
- JCUQWSIALJCIEE-UHFFFAOYSA-N 3,4-dichlorothiolane 1,1-dioxide Chemical class ClC1CS(=O)(=O)CC1Cl JCUQWSIALJCIEE-UHFFFAOYSA-N 0.000 claims 3
- 239000012442 inert solvent Substances 0.000 claims 3
- 239000013067 intermediate product Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 28
- 150000001875 compounds Chemical class 0.000 abstract description 13
- 238000006467 substitution reaction Methods 0.000 abstract description 11
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 10
- 229950005499 carbon tetrachloride Drugs 0.000 description 9
- 150000003457 sulfones Chemical class 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000498 cooling water Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- MVPOKAWQFOPTBD-UHFFFAOYSA-N 3,3,4,4-tetrachlorothiolane Chemical compound ClC1(Cl)CSCC1(Cl)Cl MVPOKAWQFOPTBD-UHFFFAOYSA-N 0.000 description 2
- 241000861718 Chloris <Aves> Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- MCOQHIWZJUDQIC-UHFFFAOYSA-N barban Chemical compound ClCC#CCOC(=O)NC1=CC=CC(Cl)=C1 MCOQHIWZJUDQIC-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YNOUGTFXHKAOCQ-UHFFFAOYSA-N 2,2,3,3-tetrachlorothiolane Chemical compound ClC1(Cl)CCSC1(Cl)Cl YNOUGTFXHKAOCQ-UHFFFAOYSA-N 0.000 description 1
- PPJYSSNKSXAVDB-UHFFFAOYSA-N 3,3',5,5'-tetraiodothyroacetic acid Chemical compound IC1=CC(CC(=O)O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 PPJYSSNKSXAVDB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 241000490229 Eucephalus Species 0.000 description 1
- 241001163743 Perlodes Species 0.000 description 1
- XDXHAEQXIBQUEZ-UHFFFAOYSA-N Ropinirole hydrochloride Chemical compound Cl.CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2 XDXHAEQXIBQUEZ-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010408 sweeping Methods 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/46—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom
- C07D333/48—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom by oxygen atoms
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/595,531 US3963751A (en) | 1975-07-14 | 1975-07-14 | Chlorination of butadiene sulfone to 3,3,4,4-tetrachlorotetrahydrothiophene-1,1-dioxide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1064508A true CA1064508A (en) | 1979-10-16 |
Family
ID=24383608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA253,059A Expired CA1064508A (en) | 1975-07-14 | 1976-05-21 | Chlorination of butadiene sulfone to 3,3,4,4-tetrachlorotetrahydrothiophene-1,1-dioxide |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3963751A (Direct) |
| JP (1) | JPS5210263A (Direct) |
| AU (1) | AU505681B2 (Direct) |
| BR (1) | BR7603324A (Direct) |
| CA (1) | CA1064508A (Direct) |
| DE (1) | DE2622980A1 (Direct) |
| ES (1) | ES448047A1 (Direct) |
| FI (1) | FI761167A7 (Direct) |
| FR (1) | FR2318162A1 (Direct) |
| GB (1) | GB1475670A (Direct) |
| IT (1) | IT1061264B (Direct) |
| MX (1) | MX3572E (Direct) |
| NO (1) | NO146539C (Direct) |
| SE (1) | SE422940B (Direct) |
| ZA (1) | ZA762203B (Direct) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62243503A (ja) * | 1986-04-15 | 1987-10-24 | ワイケイケイ株式会社 | スライドフアスナ−裏表転換搬送装置 |
| DE102005011229A1 (de) * | 2005-03-11 | 2006-09-14 | Bayer Cropscience Ag | Verfahren zur Darstellung von 3,3,4,4-Tetrachlortetrahydrothiophen-1,1-dioxid |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL225762A (Direct) * | 1957-03-13 | |||
| US2922826A (en) * | 1958-01-23 | 1960-01-26 | Sun Oil Co | Process for preparing chloroprene |
-
1975
- 1975-07-14 US US05/595,531 patent/US3963751A/en not_active Expired - Lifetime
-
1976
- 1976-04-12 NO NO761259A patent/NO146539C/no unknown
- 1976-04-12 ZA ZA762203A patent/ZA762203B/xx unknown
- 1976-04-13 AU AU12938/76A patent/AU505681B2/en not_active Expired
- 1976-04-13 SE SE7604321A patent/SE422940B/xx unknown
- 1976-04-21 GB GB1620076A patent/GB1475670A/en not_active Expired
- 1976-04-27 FI FI761167A patent/FI761167A7/fi not_active Application Discontinuation
- 1976-05-10 IT IT49395/76A patent/IT1061264B/it active
- 1976-05-12 FR FR7614256A patent/FR2318162A1/fr active Granted
- 1976-05-14 MX MX76240U patent/MX3572E/es unknown
- 1976-05-18 ES ES448047A patent/ES448047A1/es not_active Expired
- 1976-05-21 DE DE19762622980 patent/DE2622980A1/de not_active Withdrawn
- 1976-05-21 CA CA253,059A patent/CA1064508A/en not_active Expired
- 1976-05-26 BR BR7603324A patent/BR7603324A/pt unknown
- 1976-05-27 JP JP51061724A patent/JPS5210263A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE2622980A1 (de) | 1977-02-03 |
| FI761167A7 (Direct) | 1977-01-15 |
| BR7603324A (pt) | 1977-05-24 |
| ZA762203B (en) | 1977-05-25 |
| NO761259L (Direct) | 1977-01-17 |
| US3963751A (en) | 1976-06-15 |
| NO146539B (no) | 1982-07-12 |
| NO146539C (no) | 1982-10-20 |
| FR2318162A1 (fr) | 1977-02-11 |
| ES448047A1 (es) | 1977-11-01 |
| AU1293876A (en) | 1977-10-20 |
| AU505681B2 (en) | 1979-11-29 |
| SE422940B (sv) | 1982-04-05 |
| FR2318162B1 (Direct) | 1982-11-05 |
| SE7604321L (sv) | 1977-01-15 |
| IT1061264B (it) | 1983-02-28 |
| JPS5210263A (en) | 1977-01-26 |
| MX3572E (es) | 1981-03-17 |
| GB1475670A (en) | 1977-06-01 |
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