SU535294A1 - Способ получени 2,5-дихлор-4-алкилмеркаптофенолов - Google Patents
Способ получени 2,5-дихлор-4-алкилмеркаптофеноловInfo
- Publication number
- SU535294A1 SU535294A1 SU1267774A SU1267774A SU535294A1 SU 535294 A1 SU535294 A1 SU 535294A1 SU 1267774 A SU1267774 A SU 1267774A SU 1267774 A SU1267774 A SU 1267774A SU 535294 A1 SU535294 A1 SU 535294A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- alkyl
- dichloro
- mercaptophenols
- producing
- yield
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 5
- RMVRSNDYEFQCLF-UHFFFAOYSA-N phenyl mercaptan Natural products SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 4
- -1 alkyl mercaptobenzene derivatives Chemical class 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YGFPFLRARVYKBZ-UHFFFAOYSA-N 2,5-dichloro-4-methylsulfanylphenol Chemical compound CSC1=CC(Cl)=C(O)C=C1Cl YGFPFLRARVYKBZ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HYVHLWATOYTKGU-UHFFFAOYSA-N 3,5-dichloro-4-methylsulfanylaniline Chemical compound CSC1=C(Cl)C=C(N)C=C1Cl HYVHLWATOYTKGU-UHFFFAOYSA-N 0.000 description 1
- AYMFZPCOKSCUCG-UHFFFAOYSA-N 3,5-dichloro-4-methylsulfanylphenol Chemical compound CSC1=C(Cl)C=C(O)C=C1Cl AYMFZPCOKSCUCG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
- A01N57/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34 containing aromatic radicals
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing aromatic radicals
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4084—Esters with hydroxyaryl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
1
Изобретение относитс к упрощенному способу получени хлорпроизводпых алкилмеркаптобензола , которые представл ют собой ценные промежуточные продукты дл синтеза веществ, обладающих физиологической активкостью , например инсектицидов.
Известен многостадийный способ получени 3,5-дихлор-4-метилмеркаптофенола, заключающийс в том, что 2,2,6,6- тетрахлор-4,4-метилмеркаптобепзол в диоксане восстанавливают (Fe-|-HCl) до 3,5-дихлор-4-метилмеркаптоанилина . Полученный продукт диазотируют (H2SO4+NaNO2), диазораствор выливают на лед, избыток азотистой кислоты разлагают мочевиной. Затем этот раствор медленно вливают в кип щую 25%-пую серную кислоту, реакционную массу экстрагируют эфиром, эфир отгон ют, целевой продукт выдел ют вакуумной разгонкой. Выход целевого продукта 49%. С целью упрощени процесса и увеличени выхода целевого продукта 2,4,5-трихлор-1-алкилмеркаптобепзол обрабатывают спиртовой щелочью при 160-170°С. Выход целевого продукта 85%.
Пример. Получение 2,5-дихлор-4-метилмеркаптофенола .
Смесь 455 г 2,4,5-трихлор-1-метилмер.ка:ПтОбензола , 370 г 48%-ного раствора едкого натра нагревают в 1 л метапола в течение 6 ч при 160°С в автоклаве. Затем отдел ют осадок, из фильтрата отгон ют метанол и остаток разбавл ют водой. Полученный раствор фильтруют через активированный уголь, фильтрат подкисл ют концентрированной сол ной кислотой и экстрагируют продукт путем взбалтывани с метиленхлоридом. Затем раствор продукта в метиленхлориде сушат над сульфатом натри , отгон ют метиленхлорид и получают 355 г (85% от теоретического выхода) 2,5-дихлор-4-метилмеркаптофенола с т. пл. 110°С.
После перекристаллизации из бензола продукт имеет т. пл. 110-112°С.
Claims (1)
- Формула изобретениСпособ получени 2,5-дихлор-4-алкилмеркаптофенолов на основе производных алкилмеркаптобензола , отличающийс тем, что, с целью упрощени процесса и повышени выхода целевого продукта, в качестве производного алкилмеркаптобепзола используют 2,4,5трихлор-1-алкилмеркаптобензол , который обрабатывают спиртовым раствором щелочи : при температуре 160-170°С.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB89951A DE1298990B (de) | 1966-11-22 | 1966-11-22 | O, O-Dialkyl-O-(2, 5-dichlor-4-alkyl-mercapto-phenyl)-thionophosphate und Verfahren zu ihrer Herstellung |
DEB0093427 | 1967-07-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
SU535294A1 true SU535294A1 (ru) | 1976-11-15 |
Family
ID=25968203
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU1267774A SU535294A1 (ru) | 1966-11-22 | 1968-08-20 | Способ получени 2,5-дихлор-4-алкилмеркаптофенолов |
Country Status (17)
Country | Link |
---|---|
US (1) | US3600472A (ru) |
JP (1) | JPS5140141B1 (ru) |
AT (1) | AT279641B (ru) |
BE (1) | BE706911A (ru) |
CH (1) | CH524957A (ru) |
CS (2) | CS161835B2 (ru) |
DE (2) | DE1298990B (ru) |
DK (2) | DK120636B (ru) |
ES (4) | ES347336A1 (ru) |
GB (1) | GB1210826A (ru) |
IL (2) | IL28983A (ru) |
MY (1) | MY7100155A (ru) |
NL (1) | NL145862B (ru) |
SE (2) | SE370232B (ru) |
SU (1) | SU535294A1 (ru) |
TR (1) | TR17484A (ru) |
YU (1) | YU31807B (ru) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3723538A (en) * | 1970-09-28 | 1973-03-27 | Ppg Industries Inc | Polychloro parathio phenols |
JPS5545526B2 (ru) * | 1972-04-06 | 1980-11-18 | ||
DE2516059B2 (de) * | 1975-04-12 | 1980-08-28 | Carl Hurth Maschinen- Und Zahnradfabrik, 8000 Muenchen | Werkzeug zum Herstellen oder Bearbeiten von Stirnrädern |
US4880828A (en) * | 1988-01-29 | 1989-11-14 | Uniroyal Chemical, Inc. | 2-(tetrahydro-2-thienyl)phenyl esters of phosphorothioic acid |
-
1966
- 1966-11-22 DE DEB89951A patent/DE1298990B/de active Pending
-
1967
- 1967-07-11 DE DE19671643628 patent/DE1643628A1/de not_active Withdrawn
- 1967-11-15 US US683125A patent/US3600472A/en not_active Expired - Lifetime
- 1967-11-18 ES ES347336A patent/ES347336A1/es not_active Expired
- 1967-11-18 ES ES347335A patent/ES347335A1/es not_active Expired
- 1967-11-20 NL NL676715710A patent/NL145862B/xx not_active IP Right Cessation
- 1967-11-20 YU YU2255/67A patent/YU31807B/xx unknown
- 1967-11-20 CH CH1617767A patent/CH524957A/de not_active IP Right Cessation
- 1967-11-20 TR TR17484A patent/TR17484A/xx unknown
- 1967-11-21 IL IL28983A patent/IL28983A/en unknown
- 1967-11-21 IL IL37183A patent/IL37183A/xx unknown
- 1967-11-21 DK DK583067AA patent/DK120636B/da not_active IP Right Cessation
- 1967-11-22 BE BE706911D patent/BE706911A/xx not_active IP Right Cessation
- 1967-11-22 JP JP42074783A patent/JPS5140141B1/ja active Pending
- 1967-11-22 SE SE7004692A patent/SE370232B/xx unknown
- 1967-11-22 CS CS2737*[A patent/CS161835B2/cs unknown
- 1967-11-22 CS CS8279A patent/CS161834B2/cs unknown
- 1967-11-22 GB GB53225/67A patent/GB1210826A/en not_active Expired
- 1967-11-22 AT AT858768A patent/AT279641B/de not_active IP Right Cessation
- 1967-11-22 SE SE16068/67A patent/SE340448B/xx unknown
-
1968
- 1968-08-20 SU SU1267774A patent/SU535294A1/ru active
- 1968-12-19 ES ES361658A patent/ES361658A1/es not_active Expired
- 1968-12-19 ES ES361657A patent/ES361657A1/es not_active Expired
-
1970
- 1970-06-02 DK DK285070AA patent/DK123169B/da not_active IP Right Cessation
-
1971
- 1971-12-30 MY MY155/71A patent/MY7100155A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
IL37183A (en) | 1971-10-20 |
BE706911A (ru) | 1968-05-22 |
DK123169B (da) | 1972-05-23 |
DE1298990B (de) | 1969-07-10 |
SE340448B (ru) | 1971-11-22 |
IL28983A (en) | 1971-10-20 |
CS161835B2 (ru) | 1975-06-10 |
GB1210826A (en) | 1970-11-04 |
ES361657A1 (es) | 1970-11-01 |
TR17484A (tr) | 1975-07-23 |
DE1643628A1 (de) | 1971-02-11 |
YU225567A (en) | 1973-06-30 |
MY7100155A (en) | 1971-12-31 |
ES347335A1 (es) | 1976-06-01 |
ES361658A1 (es) | 1970-11-01 |
ES347336A1 (es) | 1969-05-16 |
DK120636B (da) | 1971-06-28 |
YU31807B (en) | 1973-12-31 |
AT279641B (de) | 1970-03-10 |
US3600472A (en) | 1971-08-17 |
NL145862B (nl) | 1975-05-15 |
CH524957A (de) | 1972-07-15 |
JPS5140141B1 (ru) | 1976-11-01 |
CS161834B2 (ru) | 1975-06-10 |
SE370232B (ru) | 1974-10-07 |
NL6715710A (ru) | 1968-05-24 |
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