GB1043096A - Process for the manufacture of o, o-dialkylthiono-phosphoric acid chlorides - Google Patents
Process for the manufacture of o, o-dialkylthiono-phosphoric acid chloridesInfo
- Publication number
- GB1043096A GB1043096A GB36323/64A GB3632364A GB1043096A GB 1043096 A GB1043096 A GB 1043096A GB 36323/64 A GB36323/64 A GB 36323/64A GB 3632364 A GB3632364 A GB 3632364A GB 1043096 A GB1043096 A GB 1043096A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chlorine
- alcohol
- suspension
- reaction
- butanol
- 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 6
- 239000000460 chlorine Substances 0.000 abstract 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 5
- 229910052801 chlorine Inorganic materials 0.000 abstract 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 239000000725 suspension Substances 0.000 abstract 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 abstract 2
- 239000012442 inert solvent Substances 0.000 abstract 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 abstract 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 229960004592 isopropanol Drugs 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000001256 steam distillation Methods 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 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
- C07F9/20—Esters of thiophosphoric acids containing P-halide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
O,O-Dialkylthionophosphoric acid chlorides of the formula (RO)2P(S)Cl in which R represents a C1 to C6 alkyl radical, are obtained by reacting a suspension of P2S5 in an inert solvent at a temperature of from about 0 to 150 DEG C. with Cl2 and a C1 to C6 alkanol by introducing into the said suspension a stream of chlorine and adding dropwise concurrently the said alcohol, allowing the chlorination reaction to proceed to completion, expelling the solvent from the reaction mixture and isolating the O,O-dialkylthionophosphoric acid chloride by distillation. The preferred mole ratio of P2S5 to alcohol to chlorine is 1:4.0 to 4.4:2.2 to 3.2. It is also preferred that the chlorine and alcohol are introduced to the P2S5 suspension at a feed rate of approximately 1:2 (molar). The balance of chlorine is then introduced at a constant feed rate. Specified inert solvents are toluene, xylene, carbon tetrachloride, petroleum ether (boiling point 65-95 DEG C.) and the O,O-dialkylthionophosphoric acid chloride obtained as the reaction product. Specified alcohols are methanol, ethanol, n-propanol, iso-propanol, n-butanol, iso-butanol, amyl alcohol, hexyl alcohol and the isomers thereof. The chlorine used in the reaction may be diluted with inert gas such as CO2, A and N2 in a ratio by volume of about 1:0.5 to 1:3. The product may be purified by steam distillation.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK50811A DE1191369B (en) | 1963-09-13 | 1963-09-13 | Process for the preparation of O, O-dialkyl-thionophosphoric acid chlorides |
| DEK53557A DE1211170B (en) | 1963-09-13 | 1964-07-24 | Process for the preparation of O, O-dialkylthionophosphoric acid chlorides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1043096A true GB1043096A (en) | 1966-09-21 |
Family
ID=25983798
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB36323/64A Expired GB1043096A (en) | 1963-09-13 | 1964-09-04 | Process for the manufacture of o, o-dialkylthiono-phosphoric acid chlorides |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3356774A (en) |
| CH (1) | CH437260A (en) |
| DE (2) | DE1191369B (en) |
| DK (1) | DK114129B (en) |
| GB (1) | GB1043096A (en) |
| NL (1) | NL153206B (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1191369B (en) * | 1963-09-13 | 1965-04-22 | Knapsack Ag | Process for the preparation of O, O-dialkyl-thionophosphoric acid chlorides |
| FR1466354A (en) * | 1965-10-12 | 1967-01-20 | Rhone Poulenc Sa | Process for preparing chlordialcoylthiophosphates |
| DE2538310C3 (en) * | 1975-08-28 | 1980-08-28 | Hoechst Ag, 6000 Frankfurt | Process for the preparation of O.O-dialkylthionophosphoric acid chlorides |
| US4185053A (en) * | 1977-10-03 | 1980-01-22 | Stauffer Chemical Company | Process for manufacturing substantially pure dialkyl phosphorochloridothionate |
| US4159289A (en) * | 1978-03-02 | 1979-06-26 | Ethyl Corporation | Process for preparing dialkyl phosphorochloridothioates |
| US4247490A (en) * | 1979-09-10 | 1981-01-27 | Ethyl Corporation | Process for the purification of dialkylphosphorochloridothioates |
| US4292139A (en) * | 1979-09-11 | 1981-09-29 | Ethyl Corporation | Method for inhibiting deposit formation in distillation units associated with separation and purification of alkyl phosphorochloridothioates |
| US4332747A (en) * | 1980-09-17 | 1982-06-01 | Stauffer Chemical Company | Process for producing dialkyl phosphorochloridothionates |
| US5278331A (en) * | 1990-10-09 | 1994-01-11 | Ethyl Corporation | Waste treatment in dialkyl phosphorochloridothioate production |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1191369B (en) * | 1963-09-13 | 1965-04-22 | Knapsack Ag | Process for the preparation of O, O-dialkyl-thionophosphoric acid chlorides |
-
1963
- 1963-09-13 DE DEK50811A patent/DE1191369B/en active Pending
-
1964
- 1964-07-24 DE DEK53557A patent/DE1211170B/en active Pending
- 1964-08-13 CH CH1059664A patent/CH437260A/en unknown
- 1964-08-27 US US392611A patent/US3356774A/en not_active Expired - Lifetime
- 1964-09-04 GB GB36323/64A patent/GB1043096A/en not_active Expired
- 1964-09-10 NL NL646410551A patent/NL153206B/en unknown
- 1964-09-11 DK DK449964AA patent/DK114129B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1191369B (en) | 1965-04-22 |
| US3356774A (en) | 1967-12-05 |
| DE1211170B (en) | 1966-02-24 |
| NL6410551A (en) | 1965-03-15 |
| NL153206B (en) | 1977-05-16 |
| DK114129B (en) | 1969-06-02 |
| CH437260A (en) | 1967-06-15 |
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