CA1190940A - Oxidation of alkyl phosphonous dichlorides - Google Patents
Oxidation of alkyl phosphonous dichloridesInfo
- Publication number
- CA1190940A CA1190940A CA000414714A CA414714A CA1190940A CA 1190940 A CA1190940 A CA 1190940A CA 000414714 A CA000414714 A CA 000414714A CA 414714 A CA414714 A CA 414714A CA 1190940 A CA1190940 A CA 1190940A
- Authority
- CA
- Canada
- Prior art keywords
- dichloride
- mixture
- phosphorus trichloride
- reaction
- oxygen
- 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
- 238000007254 oxidation reaction Methods 0.000 title description 6
- 230000003647 oxidation Effects 0.000 title description 5
- -1 alkyl phosphonous dichlorides Chemical class 0.000 title description 4
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 20
- CDPKWOKGVUHZFR-UHFFFAOYSA-N dichloro(methyl)phosphane Chemical compound CP(Cl)Cl CDPKWOKGVUHZFR-UHFFFAOYSA-N 0.000 claims abstract description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 16
- 239000001301 oxygen Substances 0.000 claims abstract description 16
- SCLFRABIDYGTAZ-UHFFFAOYSA-N methylphosphonic acid dichloride Chemical compound CP(Cl)(Cl)=O SCLFRABIDYGTAZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000011541 reaction mixture Substances 0.000 claims abstract description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000012263 liquid product Substances 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 125000005499 phosphonyl group Chemical group 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 235000014786 phosphorus Nutrition 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- TZFQFCHZSARYBH-UHFFFAOYSA-N P(=O)(O)OP(=O)O.CC(O)(C(CO)(CO)CO)C Chemical compound P(=O)(O)OP(=O)O.CC(O)(C(CO)(CO)CO)C TZFQFCHZSARYBH-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- CWGBRLKMLXPOIE-UHFFFAOYSA-N [P].C Chemical compound [P].C CWGBRLKMLXPOIE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- IMDXZWRLUZPMDH-UHFFFAOYSA-N dichlorophenylphosphine Chemical compound ClP(Cl)C1=CC=CC=C1 IMDXZWRLUZPMDH-UHFFFAOYSA-N 0.000 description 1
- LWNLXVXSCCLRRZ-UHFFFAOYSA-N dichlorophosphane Chemical class ClPCl LWNLXVXSCCLRRZ-UHFFFAOYSA-N 0.000 description 1
- KLPNNNPYJAOWOL-UHFFFAOYSA-N dichlorophosphane methane Chemical compound C.ClPCl KLPNNNPYJAOWOL-UHFFFAOYSA-N 0.000 description 1
- IBDMRHDXAQZJAP-UHFFFAOYSA-N dichlorophosphorylbenzene Chemical compound ClP(Cl)(=O)C1=CC=CC=C1 IBDMRHDXAQZJAP-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 229960003903 oxygen Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- JRJVWTRZBBWEDZ-UHFFFAOYSA-N tetrachloro(phenyl)-$l^{5}-phosphane Chemical compound ClP(Cl)(Cl)(Cl)C1=CC=CC=C1 JRJVWTRZBBWEDZ-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
- C07F9/28—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)]
- C07F9/42—Halides thereof
-
- 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
- C07F9/50—Organo-phosphines
- C07F9/52—Halophosphines
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US321,857 | 1981-11-16 | ||
| US06/321,857 US4411842A (en) | 1981-11-16 | 1981-11-16 | Oxidation of alkyl phosphonous dichlorides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1190940A true CA1190940A (en) | 1985-07-23 |
Family
ID=23252332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000414714A Expired CA1190940A (en) | 1981-11-16 | 1982-11-02 | Oxidation of alkyl phosphonous dichlorides |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4411842A (enExample) |
| JP (1) | JPS5892687A (enExample) |
| CA (1) | CA1190940A (enExample) |
| DE (1) | DE3242416A1 (enExample) |
| FR (1) | FR2516518A1 (enExample) |
| GB (1) | GB2109380B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4871486A (en) * | 1984-12-12 | 1989-10-03 | Olin Corporation | Process for making methylphosphonic dichloride |
| DE4029328A1 (de) * | 1990-09-15 | 1992-03-19 | Bayer Ag | Verfahren zur herstellung von organischen phosphoroxyhalogeniden |
| JP7175478B2 (ja) * | 2017-07-12 | 2022-11-21 | 株式会社Mmag | 除草剤中間体の製造法 |
| CN108659042B (zh) * | 2018-06-22 | 2020-08-04 | 河北威远生物化工有限公司 | 一种烷基二氯化膦的萃取分离方法及萃取精馏设备 |
| CN121426837B (zh) * | 2025-12-31 | 2026-03-17 | 山东新和成氨基酸有限公司 | 一种杂多酸负载型催化剂催化制备甲基二氯化磷的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE910649C (de) * | 1943-01-05 | 1954-05-03 | Hoechst Ag | Verfahren zur Herstellung von aliphatischen Phosphonsaeurechloriden |
| US2683168A (en) * | 1950-12-22 | 1954-07-06 | California Research Corp | Preparation of organo phosphonyl chlorides |
| US3210418A (en) * | 1953-10-19 | 1965-10-05 | Fmc Corp | Preparation of aliphatic dihalophosphines |
| US3188281A (en) * | 1954-03-31 | 1965-06-08 | Olin Mathieson | Production of methyl dichlorophosphine oxide |
| FR1440985A (fr) * | 1965-06-18 | 1966-06-03 | Fmc Corp | Procédé de fabrication d'halophosphines et produits obtenus |
| US4252740A (en) * | 1978-09-29 | 1981-02-24 | Stauffer Chemical Company | Oxidation of phenyl phosphonous dihalide |
-
1981
- 1981-11-16 US US06/321,857 patent/US4411842A/en not_active Expired - Fee Related
-
1982
- 1982-11-02 CA CA000414714A patent/CA1190940A/en not_active Expired
- 1982-11-15 GB GB08232588A patent/GB2109380B/en not_active Expired
- 1982-11-15 FR FR8219076A patent/FR2516518A1/fr active Granted
- 1982-11-16 JP JP57201008A patent/JPS5892687A/ja active Pending
- 1982-11-16 DE DE19823242416 patent/DE3242416A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB2109380A (en) | 1983-06-02 |
| GB2109380B (en) | 1985-08-21 |
| FR2516518A1 (fr) | 1983-05-20 |
| US4411842A (en) | 1983-10-25 |
| JPS5892687A (ja) | 1983-06-02 |
| DE3242416A1 (de) | 1983-05-26 |
| FR2516518B1 (enExample) | 1985-03-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |