CA1050994A - Ethanolysis of 3-trichloromethyl-5-chloro-1,2,4-thiadiazole - Google Patents
Ethanolysis of 3-trichloromethyl-5-chloro-1,2,4-thiadiazoleInfo
- Publication number
- CA1050994A CA1050994A CA224,070A CA224070A CA1050994A CA 1050994 A CA1050994 A CA 1050994A CA 224070 A CA224070 A CA 224070A CA 1050994 A CA1050994 A CA 1050994A
- Authority
- CA
- Canada
- Prior art keywords
- thiadiazole
- trichloromethyl
- reaction mixture
- chloro
- water
- 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
- MARKPJMFLDWCID-UHFFFAOYSA-N 5-chloro-3-(trichloromethyl)-1,2,4-thiadiazole Chemical compound ClC1=NC(C(Cl)(Cl)Cl)=NS1 MARKPJMFLDWCID-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 238000010932 ethanolysis reaction Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 42
- 239000011541 reaction mixture Substances 0.000 claims abstract description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
- 239000002585 base Substances 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 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
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- KQTVWCSONPJJPE-UHFFFAOYSA-N etridiazole Chemical group CCOC1=NC(C(Cl)(Cl)Cl)=NS1 KQTVWCSONPJJPE-UHFFFAOYSA-N 0.000 claims 3
- DPESXDQFGGVEIH-UHFFFAOYSA-N 5-chloro-3-(trichloromethyl)-2H-thiadiazole Chemical compound ClC1=CN(NS1)C(Cl)(Cl)Cl DPESXDQFGGVEIH-UHFFFAOYSA-N 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 1
- 238000004064 recycling Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 31
- 239000012071 phase Substances 0.000 description 16
- 239000000839 emulsion Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000003518 caustics Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- -1 5-chloro compound Chemical class 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 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 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003398 denaturant Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000005057 refrigeration Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 230000016507 interphase Effects 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- RZKVGQCJNANFDR-UHFFFAOYSA-N 5-chloro-1,2,4-thiadiazole Chemical compound ClC1=NC=NS1 RZKVGQCJNANFDR-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ONXBYKYVNWZCTH-UHFFFAOYSA-N ClC(C(N=C1)=N[S+]1Cl)(Cl)Cl Chemical compound ClC(C(N=C1)=N[S+]1Cl)(Cl)Cl ONXBYKYVNWZCTH-UHFFFAOYSA-N 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 241000233639 Pythium Species 0.000 description 1
- 241001558929 Sclerotium <basidiomycota> Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US466434A US3890338A (en) | 1974-05-02 | 1974-05-02 | Ethanolysis of 3-trichloromethyl-5-chloro-1,2,4-thiadizole employing aqueous base |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1050994A true CA1050994A (en) | 1979-03-20 |
Family
ID=23851732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA224,070A Expired CA1050994A (en) | 1974-05-02 | 1975-04-08 | Ethanolysis of 3-trichloromethyl-5-chloro-1,2,4-thiadiazole |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3890338A (en, 2012) |
| JP (1) | JPS5850219B2 (en, 2012) |
| AR (1) | AR206023A1 (en, 2012) |
| BE (1) | BE828696A (en, 2012) |
| BR (1) | BR7502592A (en, 2012) |
| CA (1) | CA1050994A (en, 2012) |
| CH (1) | CH611285A5 (en, 2012) |
| DE (1) | DE2519314C2 (en, 2012) |
| FR (1) | FR2269527B1 (en, 2012) |
| GB (1) | GB1477975A (en, 2012) |
| IE (1) | IE40967B1 (en, 2012) |
| IT (1) | IT1035262B (en, 2012) |
| NL (1) | NL7504640A (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4057639A (en) * | 1977-02-14 | 1977-11-08 | Olin Corporation | Method for using 3-trichloromethyl-5-lower alkoxy-1,2,4-thiadiazole compounds as insecticides and acaricides |
| US4143044A (en) * | 1978-04-05 | 1979-03-06 | Olin Corporation | Process for making selected 3-trihalomethyl-5-lower alkoxy-1,2,4-thiadiazoles |
| US20070147187A1 (en) * | 2005-12-28 | 2007-06-28 | Gennady Resnick | Method of using graphite for making hydrophilic articles |
| US20080025898A1 (en) | 2005-12-28 | 2008-01-31 | Gennady Resnick | Method of treating a material to achieve sufficient hydrophilicity for making hydrophilic articles |
| US20070148361A1 (en) * | 2005-12-28 | 2007-06-28 | Gennady Resnick | Method of treating graphite for making hydrophilic articles |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3260725A (en) * | 1961-03-15 | 1966-07-12 | Olin Mathieson | 3-trichloromethyl-5-substituted-1, 2, 4-thiadiazole |
-
1974
- 1974-05-02 US US466434A patent/US3890338A/en not_active Expired - Lifetime
-
1975
- 1975-01-01 AR AR258589A patent/AR206023A1/es active
- 1975-04-07 IE IE770/75A patent/IE40967B1/xx unknown
- 1975-04-08 CA CA224,070A patent/CA1050994A/en not_active Expired
- 1975-04-10 IT IT49038/75A patent/IT1035262B/it active
- 1975-04-15 GB GB1547575A patent/GB1477975A/en not_active Expired
- 1975-04-18 NL NL7504640A patent/NL7504640A/xx not_active Application Discontinuation
- 1975-04-25 JP JP50050610A patent/JPS5850219B2/ja not_active Expired
- 1975-04-29 BR BR3289/75A patent/BR7502592A/pt unknown
- 1975-04-29 CH CH548075A patent/CH611285A5/xx not_active IP Right Cessation
- 1975-04-30 FR FR7513732A patent/FR2269527B1/fr not_active Expired
- 1975-04-30 DE DE2519314A patent/DE2519314C2/de not_active Expired
- 1975-05-02 BE BE156039A patent/BE828696A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1477975A (en) | 1977-06-29 |
| IE40967B1 (en) | 1979-09-26 |
| DE2519314C2 (de) | 1984-03-22 |
| US3890338A (en) | 1975-06-17 |
| JPS50149673A (en, 2012) | 1975-11-29 |
| NL7504640A (nl) | 1975-11-04 |
| FR2269527A1 (en, 2012) | 1975-11-28 |
| IE40967L (en) | 1975-11-02 |
| BR7502592A (pt) | 1976-03-16 |
| IT1035262B (it) | 1979-10-20 |
| FR2269527B1 (en, 2012) | 1980-01-04 |
| AR206023A1 (es) | 1976-06-23 |
| AU8005475A (en) | 1976-10-14 |
| CH611285A5 (en, 2012) | 1979-05-31 |
| BE828696A (fr) | 1975-11-03 |
| JPS5850219B2 (ja) | 1983-11-09 |
| DE2519314A1 (de) | 1975-11-06 |
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