JPS6347717B2 - - Google Patents
Info
- Publication number
- JPS6347717B2 JPS6347717B2 JP6964680A JP6964680A JPS6347717B2 JP S6347717 B2 JPS6347717 B2 JP S6347717B2 JP 6964680 A JP6964680 A JP 6964680A JP 6964680 A JP6964680 A JP 6964680A JP S6347717 B2 JPS6347717 B2 JP S6347717B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- alkyl
- formula
- phosphorus oxychloride
- thiophosphoric acid
- 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
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 31
- -1 thiophosphoric acid triester Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 38
- 239000000460 chlorine Substances 0.000 description 15
- 239000002994 raw material Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 7
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000010813 internal standard method Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000005691 triesters Chemical class 0.000 description 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 description 2
- 238000006418 Brown reaction Methods 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- DQTRYXANLKJLPK-UHFFFAOYSA-N chlorophosphonous acid Chemical compound OP(O)Cl DQTRYXANLKJLPK-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- RMVRSNDYEFQCLF-UHFFFAOYSA-N phenyl mercaptan Natural products SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- HMANYETUONUMIX-UHFFFAOYSA-N CCC[S+]=P(O)(O)O Chemical compound CCC[S+]=P(O)(O)O HMANYETUONUMIX-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- ALVPFGSHPUPROW-UHFFFAOYSA-N dipropyl disulfide Chemical compound CCCSSCCC ALVPFGSHPUPROW-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6964680A JPS56166197A (en) | 1980-05-27 | 1980-05-27 | O-alkyl s-alkyl or -aryl thiophosphoric chloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6964680A JPS56166197A (en) | 1980-05-27 | 1980-05-27 | O-alkyl s-alkyl or -aryl thiophosphoric chloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56166197A JPS56166197A (en) | 1981-12-21 |
| JPS6347717B2 true JPS6347717B2 (pt) | 1988-09-26 |
Family
ID=13408811
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6964680A Granted JPS56166197A (en) | 1980-05-27 | 1980-05-27 | O-alkyl s-alkyl or -aryl thiophosphoric chloride |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56166197A (pt) |
-
1980
- 1980-05-27 JP JP6964680A patent/JPS56166197A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56166197A (en) | 1981-12-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| McIvor et al. | Preparation and toxicity of some alkyl thiopyrophosphates | |
| JPS5819677B2 (ja) | 燐のシリルアルキルエステルの製造方法 | |
| Stec et al. | New synthesis of S (Se)-alkyl phosphorothio (seleno) lates from the corresponding phosphoroanilidates. Stereospecific cleavage of the phosphorus-nitrogen bond in chiral phosphoroanilidates | |
| US4371509A (en) | Oxidizing phosphorus compounds with chlorosulfonic acid | |
| US4536350A (en) | Process for making chlorophosphanes, phosphinic acid chlorides or thiophosphinic acid chloride, and novel isomeric mixture consisting of chloro-phosphabicyclononanes | |
| JPH085905B2 (ja) | ビス―（２，４―ジ―第三ブチルフェニル）ハロホスフィットの製造方法 | |
| JPS6347717B2 (pt) | ||
| US4118435A (en) | Catalyzed production of phosphorous and phosphonous acid ester chlorides | |
| US3642960A (en) | Method of producing thiono- or dithio-phosphonic acid esters | |
| US2993929A (en) | Process for preparing phosphonothioic chlorides and phosphinothioic chlorides and newproducts produced by said process | |
| JPS6411030B2 (pt) | ||
| JPS603317B2 (ja) | 塩化ホスフアイトの製造方法 | |
| RU2528053C2 (ru) | Способ получения диалкилфосфитов | |
| US4482506A (en) | Process for the manufacture of alkyl diaryl phosphate esters | |
| US2495799A (en) | Chloroalkyl phosphorous oxy and sulfodichlorides | |
| US2799696A (en) | Manufacture of omicron-(chlorophenyl) phosphorodichloridothioates | |
| US4000190A (en) | Process for preparing alkyl- and aryl phosphonothioic dihalides | |
| US4348337A (en) | Process for the manufacture of 1-halogen-1-oxo-Δ3 -phospholenes | |
| SU943243A1 (ru) | Способ получени диарилгалогенфосфинов | |
| US3064009A (en) | O-coumaryl o-alkyl phosphoramidates and phosphoramidothioates | |
| Michalski et al. | Organophosphorus compounds. Part CXXXVI. Thiopyrophosphate synthesis by condensation of oxophosphoranesulphenyl chlorides with trialkyl phosphites and their structural analogues | |
| DK169893B1 (da) | Særlig fremgangsmåde til fremstilling af 0,0-di-lavere-alkylchlorthiophosphater | |
| US3962323A (en) | Process for preparing alkyl- or aryl-phosphonothioic dihalides | |
| US2654781A (en) | Bis (tetraalkyldiamidophosphoryl) alkanephosphonates | |
| JPS6342633B2 (pt) |