GB947778A - Improvements in or relating to the production of carbamylmethyl phosphorothioates - Google Patents
Improvements in or relating to the production of carbamylmethyl phosphorothioatesInfo
- Publication number
- GB947778A GB947778A GB331159A GB331159A GB947778A GB 947778 A GB947778 A GB 947778A GB 331159 A GB331159 A GB 331159A GB 331159 A GB331159 A GB 331159A GB 947778 A GB947778 A GB 947778A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- reaction
- phase
- aqueous phase
- dimethyl
- 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
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 title abstract 5
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 239000008346 aqueous phase Substances 0.000 abstract 4
- 229910052760 oxygen Inorganic materials 0.000 abstract 4
- 239000012071 phase Substances 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000013065 commercial product Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 2
- 239000012535 impurity Substances 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- -1 thiophosphate ester Chemical class 0.000 abstract 2
- BODRLKRKPXBDBN-UHFFFAOYSA-N 3,5,5-Trimethyl-1-hexanol Chemical compound OCCC(C)CC(C)(C)C BODRLKRKPXBDBN-UHFFFAOYSA-N 0.000 abstract 1
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 abstract 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 1
- VNRMXUPMAYMQOS-UHFFFAOYSA-N NC(=O)COP(O)(S)=S Chemical compound NC(=O)COP(O)(S)=S VNRMXUPMAYMQOS-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- 239000006286 aqueous extract Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 150000008282 halocarbons Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
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)
- Luminescent Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
A thiophosphate ester of the general formula: <FORM:0947778/C2/1> is obtained by reacting together a phosphoro-thiolate salt of the formula: <FORM:0947778/C2/2> with a haloacetamide compound of the formula: <FORM:0947778/C2/3> wherein R1 is methyl, R2 is methyl or other alkyl group containing up to 5 carbon atoms, X1 and X2 are oxygen or sulphur, at least one being sulphur, R3 and R4 are hydrogen, alkyl containing up to 5 carbon atoms, or together with the N atom form a heterocyclic residue e.g. morpholine residue, Y is an alkali metal, alkaline earth metal or ammonium, and Z is chlorine or bromine, the reaction being carried out in a two phase liquid system comprising an aqueous phase and a water-immiscible organic solvent phase, the phosphorothioate salt appearing preferentially in the aqueous phase and the thiophosphate ester appearing preferentially in the solvent phase. The phosphorothioate salt may be formed in situ by introducing into the reaction the free phosphorothioic acid and an alkaline compound of an alkali metal, alkaline earth metal, or ammonium e.g. a hydroxide, carbonate, or bicarbonate. The volume ratio of the aqueous phase to the organic solvent phase may vary from 1:4 to 4:1. Specified solvents are ketones, alcohols and ethers having 4 or more carbon atoms, e.g. methyl isobutyl ketone, cyclohexanone, methyl cyclohexanone, 2,2-dichlorodiethyl ether, 3, 5, 5-trimethyl hexanol, and hydrocarbons or halogenated hydrocarbons, e.g. benzene, xylene, chlorobenzene, chloroform and carbon tetrachloride, or mixtures of such solvents. Preferred reaction temperatures are from 15 to 90 DEG C. Suitable 0, 0-dimethyl phosphorodithioates which may be used as starting material may be obtained by extracting the commercial product with water, separating the oily impurities and neutralising the aqueous extracts with a suitable base or the commercial product may be extracted with aqueous ammonia and the oily impurities separated off. The pH of the aqueous phase during reaction should preferably be not above 10 and the reaction mixture may be buffered e.g. with bicarbonate ions. Examples are given for the production of O, O-dimethyl -S-(N-methyl) carbamylmethyl phosphorodithioate, O, O-methyl ethyl -S-(N-methyl)-carbamylmethyl phosphoromonothiate and O, O-dimethyl -S-(N-methyl -N-ethyl) carbamoylmethyl phosphorodithioate. Specifications 663,270 and 791,824 are referred to. Reference has been directed by the Comptroller to Specification 886,319.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB331159A GB947778A (en) | 1959-01-30 | 1959-01-30 | Improvements in or relating to the production of carbamylmethyl phosphorothioates |
FR817034A FR1248739A (en) | 1959-01-30 | 1960-01-29 | Process for the preparation of phosphate esters |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB331159A GB947778A (en) | 1959-01-30 | 1959-01-30 | Improvements in or relating to the production of carbamylmethyl phosphorothioates |
Publications (1)
Publication Number | Publication Date |
---|---|
GB947778A true GB947778A (en) | 1964-01-29 |
Family
ID=9755926
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB331159A Expired GB947778A (en) | 1959-01-30 | 1959-01-30 | Improvements in or relating to the production of carbamylmethyl phosphorothioates |
Country Status (2)
Country | Link |
---|---|
FR (1) | FR1248739A (en) |
GB (1) | GB947778A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5251028A (en) * | 1975-10-22 | 1977-04-23 | Nippon Tokushu Noyaku Seizo Kk | Herbicide |
-
1959
- 1959-01-30 GB GB331159A patent/GB947778A/en not_active Expired
-
1960
- 1960-01-29 FR FR817034A patent/FR1248739A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
FR1248739A (en) | 1960-12-23 |
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