DE1189978B - Verfahren zur Herstellung von O, O-Dialkyldithiophosphorylessigsaeuremonoalkylamiden - Google Patents
Verfahren zur Herstellung von O, O-DialkyldithiophosphorylessigsaeuremonoalkylamidenInfo
- Publication number
- DE1189978B DE1189978B DES82171A DES0082171A DE1189978B DE 1189978 B DE1189978 B DE 1189978B DE S82171 A DES82171 A DE S82171A DE S0082171 A DES0082171 A DE S0082171A DE 1189978 B DE1189978 B DE 1189978B
- Authority
- DE
- Germany
- Prior art keywords
- acid
- vol
- general formula
- dialkyl
- dithiophosphorylacetic
- 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.)
- Pending
Links
- 239000002253 acid Substances 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 24
- 229910052760 oxygen Inorganic materials 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 alkyl isocyanate Chemical class 0.000 claims description 10
- 239000012948 isocyanate Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 150000001722 carbon compounds Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 150000002927 oxygen compounds Chemical class 0.000 claims description 2
- 238000012552 review Methods 0.000 claims description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001447 alkali salts Chemical class 0.000 description 3
- 238000006114 decarboxylation reaction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- OGCAJUKWNJKZFV-UHFFFAOYSA-N 2-dimethoxyphosphinothioylsulfanylacetic acid Chemical compound COP(=S)(OC)SCC(O)=O OGCAJUKWNJKZFV-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CZGGKXNYNPJFAX-UHFFFAOYSA-N Dimethyldithiophosphate Chemical compound COP(S)(=S)OC CZGGKXNYNPJFAX-UHFFFAOYSA-N 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- ZTXNBYJISZZPOX-UHFFFAOYSA-N OP1OCCO1.Cl Chemical compound OP1OCCO1.Cl ZTXNBYJISZZPOX-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ILDHFYGNYDICFB-UHFFFAOYSA-N dimethoxy-methylsulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SC ILDHFYGNYDICFB-UHFFFAOYSA-N 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing 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
- C07F9/1651—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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1189978X | 1961-10-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1189978B true DE1189978B (de) | 1965-04-01 |
Family
ID=14750440
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES82171A Pending DE1189978B (de) | 1961-10-25 | 1962-10-24 | Verfahren zur Herstellung von O, O-Dialkyldithiophosphorylessigsaeuremonoalkylamiden |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE624058A (US20100223739A1-20100909-C00005.png) |
| DE (1) | DE1189978B (US20100223739A1-20100909-C00005.png) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2909558A (en) * | 1957-05-27 | 1959-10-20 | Monsanto Chemicals | Phosphonoformamides and methods for preparation |
| FR1234879A (fr) * | 1958-07-12 | 1960-10-19 | Boehringer Sohn Ingelheim | Perfectionnements apportés aux produits pour l'extermination des animaux nuisibles et aux procédés pour préparer des anhydrides et des amides d'acides o, o-dialcoyldithiophosphoryl-gras utilisables comme matières actives dans ces produits |
-
0
- BE BE624058D patent/BE624058A/xx unknown
-
1962
- 1962-10-24 DE DES82171A patent/DE1189978B/de active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2909558A (en) * | 1957-05-27 | 1959-10-20 | Monsanto Chemicals | Phosphonoformamides and methods for preparation |
| FR1234879A (fr) * | 1958-07-12 | 1960-10-19 | Boehringer Sohn Ingelheim | Perfectionnements apportés aux produits pour l'extermination des animaux nuisibles et aux procédés pour préparer des anhydrides et des amides d'acides o, o-dialcoyldithiophosphoryl-gras utilisables comme matières actives dans ces produits |
Also Published As
| Publication number | Publication date |
|---|---|
| BE624058A (US20100223739A1-20100909-C00005.png) |
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