DE2125143C3 - N-Chlorsulfonyl-carbamoylphosphonsäureester sowie Verfahren zu deren Herstellung - Google Patents
N-Chlorsulfonyl-carbamoylphosphonsäureester sowie Verfahren zu deren HerstellungInfo
- Publication number
- DE2125143C3 DE2125143C3 DE2125143A DE2125143A DE2125143C3 DE 2125143 C3 DE2125143 C3 DE 2125143C3 DE 2125143 A DE2125143 A DE 2125143A DE 2125143 A DE2125143 A DE 2125143A DE 2125143 C3 DE2125143 C3 DE 2125143C3
- Authority
- DE
- Germany
- Prior art keywords
- chlorosulfonyl
- reaction
- acid esters
- preparation
- processes
- 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
- 238000000034 method Methods 0.000 title description 8
- LSTLKSUKMQYVNA-UHFFFAOYSA-N chlorosulfonylcarbamoylphosphonic acid Chemical class ClS(=O)(=O)NC(=O)P(O)(O)=O LSTLKSUKMQYVNA-UHFFFAOYSA-N 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 3
- -1 N-chlorosulfonyl-carbamoylphosphoric acid ester Chemical class 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 15
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 238000007792 addition Methods 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 150000005840 aryl radicals Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000013256 coordination polymer Substances 0.000 description 3
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GCVDWIQBKRCGQC-UHFFFAOYSA-N N-didodecoxyphosphorylcarbonylsulfamoyl chloride Chemical compound C(CCCCCCCCCCC)OP(OCCCCCCCCCCCC)(=O)C(NS(=O)(=O)Cl)=O GCVDWIQBKRCGQC-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- OSPSWZSRKYCQPF-UHFFFAOYSA-N dibutoxy(oxo)phosphanium Chemical compound CCCCO[P+](=O)OCCCC OSPSWZSRKYCQPF-UHFFFAOYSA-N 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 150000003008 phosphonic acid esters Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- OTNZNOLZCVBMRL-UHFFFAOYSA-N N-diethoxyphosphorylcarbonylsulfamoyl chloride Chemical compound C(C)OP(OCC)(=O)C(NS(=O)(=O)Cl)=O OTNZNOLZCVBMRL-UHFFFAOYSA-N 0.000 description 1
- LJTYQYUDUFXQRL-UHFFFAOYSA-N N-dimethoxyphosphorylcarbonylsulfamoyl chloride Chemical compound COP(OC)(=O)C(NS(=O)(=O)Cl)=O LJTYQYUDUFXQRL-UHFFFAOYSA-N 0.000 description 1
- FLQKVVKKTDHURF-UHFFFAOYSA-N N-diphenoxyphosphorylcarbonylsulfamoyl chloride Chemical compound C1(=CC=CC=C1)OP(OC1=CC=CC=C1)(=O)C(NS(=O)(=O)Cl)=O FLQKVVKKTDHURF-UHFFFAOYSA-N 0.000 description 1
- RHUODGTXEYJWLD-UHFFFAOYSA-N NC(=O)OP(O)=O Chemical class NC(=O)OP(O)=O RHUODGTXEYJWLD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CIAODVPOEJUUGP-UHFFFAOYSA-N O=C(NS(Cl)(=O)=O)OP(=O)=O Chemical compound O=C(NS(Cl)(=O)=O)OP(=O)=O CIAODVPOEJUUGP-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- HDIBKVVPMJKRGL-UHFFFAOYSA-N bis(2-ethylhexyl) hydrogen phosphite Chemical compound CCCCC(CC)COP(O)OCC(CC)CCCC HDIBKVVPMJKRGL-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- QBCOASQOMILNBN-UHFFFAOYSA-N didodecoxy(oxo)phosphanium Chemical compound CCCCCCCCCCCCO[P+](=O)OCCCCCCCCCCCC QBCOASQOMILNBN-UHFFFAOYSA-N 0.000 description 1
- KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- C07F9/28—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
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4062—Esters of acids containing the structure -C(=X)-P(=X)(XR)2 or NC-P(=X)(XR)2, (X = O, S, Se)
- C07F9/4065—Esters of acids containing the structure -C(=X)-P(=X)(XR)2, (X = O, S, Se)
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2125143A DE2125143C3 (de) | 1971-05-21 | 1971-05-21 | N-Chlorsulfonyl-carbamoylphosphonsäureester sowie Verfahren zu deren Herstellung |
| GB1779672A GB1328617A (en) | 1971-05-21 | 1972-04-18 | N-chlorosulphonyl-carbamoyl phosphonic acid esters and process for making them |
| NL7206599A NL7206599A (show.php) | 1971-05-21 | 1972-05-16 | |
| BE783610A BE783610A (fr) | 1971-05-21 | 1972-05-17 | Esters de l'acide n-chlorosulfonyl-carbamoyl-phosphonique et leur procede de preparation |
| US00254462A US3839508A (en) | 1971-05-21 | 1972-05-18 | N-chlorosulfonyl-carbamoyl phosphonic acid esters |
| FR7218153A FR2138841B1 (show.php) | 1971-05-21 | 1972-05-19 | |
| IT50355/72A IT957959B (it) | 1971-05-21 | 1972-05-19 | Esteri di acido n clorosolfonil carbamoilfosfonico e procedimento per la loro produzione |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2125143A DE2125143C3 (de) | 1971-05-21 | 1971-05-21 | N-Chlorsulfonyl-carbamoylphosphonsäureester sowie Verfahren zu deren Herstellung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2125143A1 DE2125143A1 (de) | 1972-11-30 |
| DE2125143B2 DE2125143B2 (de) | 1979-05-17 |
| DE2125143C3 true DE2125143C3 (de) | 1980-01-17 |
Family
ID=5808469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2125143A Expired DE2125143C3 (de) | 1971-05-21 | 1971-05-21 | N-Chlorsulfonyl-carbamoylphosphonsäureester sowie Verfahren zu deren Herstellung |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3839508A (show.php) |
| BE (1) | BE783610A (show.php) |
| DE (1) | DE2125143C3 (show.php) |
| FR (1) | FR2138841B1 (show.php) |
| GB (1) | GB1328617A (show.php) |
| IT (1) | IT957959B (show.php) |
| NL (1) | NL7206599A (show.php) |
-
1971
- 1971-05-21 DE DE2125143A patent/DE2125143C3/de not_active Expired
-
1972
- 1972-04-18 GB GB1779672A patent/GB1328617A/en not_active Expired
- 1972-05-16 NL NL7206599A patent/NL7206599A/xx not_active Application Discontinuation
- 1972-05-17 BE BE783610A patent/BE783610A/xx unknown
- 1972-05-18 US US00254462A patent/US3839508A/en not_active Expired - Lifetime
- 1972-05-19 FR FR7218153A patent/FR2138841B1/fr not_active Expired
- 1972-05-19 IT IT50355/72A patent/IT957959B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| IT957959B (it) | 1973-10-20 |
| DE2125143A1 (de) | 1972-11-30 |
| BE783610A (fr) | 1972-11-17 |
| FR2138841A1 (show.php) | 1973-01-05 |
| FR2138841B1 (show.php) | 1977-12-23 |
| US3839508A (en) | 1974-10-01 |
| GB1328617A (en) | 1973-08-30 |
| NL7206599A (show.php) | 1972-11-23 |
| DE2125143B2 (de) | 1979-05-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| EHJ | Ceased/non-payment of the annual fee |