IL32016A - Process for the preparation of dimethylthiophosphite or of organothiophosphonous acid o-monomethyl esters - Google Patents
Process for the preparation of dimethylthiophosphite or of organothiophosphonous acid o-monomethyl estersInfo
- Publication number
- IL32016A IL32016A IL32016A IL3201669A IL32016A IL 32016 A IL32016 A IL 32016A IL 32016 A IL32016 A IL 32016A IL 3201669 A IL3201669 A IL 3201669A IL 32016 A IL32016 A IL 32016A
- Authority
- IL
- Israel
- Prior art keywords
- process according
- acid
- reaction
- hydrogen sulphide
- dimethylthiophosphite
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 32
- 230000008569 process Effects 0.000 title claims description 31
- 239000002253 acid Substances 0.000 title claims description 13
- LVFUWJLIDMSANU-UHFFFAOYSA-N methoxy(methylsulfanyl)phosphinous acid Chemical compound COP(O)SC LVFUWJLIDMSANU-UHFFFAOYSA-N 0.000 title description 22
- 238000002360 preparation method Methods 0.000 title description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 19
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 claims description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 150000007530 organic bases Chemical class 0.000 claims description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 4
- MUVSERCYUMDSPN-UHFFFAOYSA-N 2-aminopropane-1,1,2-triol Chemical class CC(N)(O)C(O)O MUVSERCYUMDSPN-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 2
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 claims 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 238000004821 distillation Methods 0.000 description 14
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 229940086542 triethylamine Drugs 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- RJODUASCKGDMQK-UHFFFAOYSA-N diethoxy(sulfanylidene)phosphanium Chemical compound CCO[P+](=S)OCC RJODUASCKGDMQK-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229910000851 Alloy steel Inorganic materials 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- -1 phosphorus compound Chemical class 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- 101100010166 Mus musculus Dok3 gene Proteins 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- WFSUZRTZCVKBFF-UHFFFAOYSA-N ethane phosphonous acid Chemical compound P(O)O.CC WFSUZRTZCVKBFF-UHFFFAOYSA-N 0.000 description 1
- KAKYPBMWXLFJOS-UHFFFAOYSA-N ethyl(methoxy)phosphinothious acid Chemical compound COP(S)CC KAKYPBMWXLFJOS-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- DMRGFEYFBCTINH-UHFFFAOYSA-N methoxy(phenyl)phosphinous acid Chemical class COP(O)C1=CC=CC=C1 DMRGFEYFBCTINH-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 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
- C07F9/201—Esters of thiophosphorus acids
- C07F9/202—Esters of thiophosphorus acids with hydroxyl compounds without further substituents on alkyl
-
- 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
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681768503 DE1768503C3 (de) | 1968-05-20 | Verfahren zur Herstellung von Dimethylthiophosphit bzw. von Niederalkylthiophosphonigsäure-O-monomethylestern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL32016A0 IL32016A0 (en) | 1969-06-25 |
| IL32016A true IL32016A (en) | 1972-04-27 |
Family
ID=5699762
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL32016A IL32016A (en) | 1968-05-20 | 1969-04-14 | Process for the preparation of dimethylthiophosphite or of organothiophosphonous acid o-monomethyl esters |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3655835A (pl) |
| BE (1) | BE733242A (pl) |
| BR (1) | BR6908985D0 (pl) |
| CH (1) | CH510698A (pl) |
| CS (1) | CS174114B2 (pl) |
| ES (1) | ES367435A1 (pl) |
| FR (1) | FR2008929A1 (pl) |
| GB (1) | GB1247414A (pl) |
| IL (1) | IL32016A (pl) |
| NL (1) | NL161159C (pl) |
| PL (1) | PL69846B1 (pl) |
| RO (1) | RO56079A (pl) |
| TR (1) | TR16874A (pl) |
-
1969
- 1969-04-11 CH CH554969A patent/CH510698A/de not_active IP Right Cessation
- 1969-04-14 IL IL32016A patent/IL32016A/en unknown
- 1969-04-23 RO RO59814A patent/RO56079A/ro unknown
- 1969-05-05 US US821995A patent/US3655835A/en not_active Expired - Lifetime
- 1969-05-05 TR TR16874A patent/TR16874A/xx unknown
- 1969-05-19 GB GB25319/69A patent/GB1247414A/en not_active Expired
- 1969-05-19 PL PL1969133683A patent/PL69846B1/pl unknown
- 1969-05-19 BE BE733242D patent/BE733242A/xx unknown
- 1969-05-20 CS CS3574A patent/CS174114B2/cs unknown
- 1969-05-20 FR FR6916345A patent/FR2008929A1/fr not_active Withdrawn
- 1969-05-20 NL NL6907698.A patent/NL161159C/xx not_active IP Right Cessation
- 1969-05-20 BR BR208985/69A patent/BR6908985D0/pt unknown
- 1969-05-20 ES ES367435A patent/ES367435A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL6907698A (pl) | 1969-11-24 |
| TR16874A (tr) | 1973-09-01 |
| FR2008929A1 (pl) | 1970-01-30 |
| CH510698A (de) | 1971-07-31 |
| BR6908985D0 (pt) | 1973-01-09 |
| DE1768503A1 (de) | 1971-10-28 |
| DE1768503B2 (de) | 1975-10-23 |
| US3655835A (en) | 1972-04-11 |
| CS174114B2 (pl) | 1977-03-31 |
| GB1247414A (en) | 1971-09-22 |
| NL161159C (nl) | 1980-01-15 |
| PL69846B1 (pl) | 1973-10-31 |
| BE733242A (pl) | 1969-11-19 |
| NL161159B (nl) | 1979-08-15 |
| RO56079A (pl) | 1974-03-01 |
| IL32016A0 (en) | 1969-06-25 |
| ES367435A1 (es) | 1971-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ERR | Corrigendum |
Free format text: CORRECT DATE OF PRIORITY 13.03.2007 |
|
| ERR | Corrigendum |
Free format text: CORRECT NAME OF APPLICANT SCINOPHARM (CHANGSHU) PHARMACEUTICALS, LTD., CHINA INFORMATION Free format text: CORRECT NAME OF APPLICANT DONG-A ST CO., LTD., REPUBLIC OF KOREA. INFORMATION |