DE1136334B - Verfahren zur Herstellung von Thionothiol- bzw. Thiolphosphon- und -phosphinsaeureestern - Google Patents
Verfahren zur Herstellung von Thionothiol- bzw. Thiolphosphon- und -phosphinsaeureesternInfo
- Publication number
- DE1136334B DE1136334B DEF30719A DEF0030719A DE1136334B DE 1136334 B DE1136334 B DE 1136334B DE F30719 A DEF30719 A DE F30719A DE F0030719 A DEF0030719 A DE F0030719A DE 1136334 B DE1136334 B DE 1136334B
- Authority
- DE
- Germany
- Prior art keywords
- thionothiol
- thiolphosphonic
- acid
- general formula
- acid esters
- 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
- 238000000034 method Methods 0.000 title claims description 6
- 239000002253 acid Substances 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- HIZCIEIDIFGZSS-UHFFFAOYSA-N carbonotrithioic acid Chemical class SC(S)=S HIZCIEIDIFGZSS-UHFFFAOYSA-N 0.000 claims description 4
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 4
- -1 alkoxy radical Chemical class 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000003008 phosphonic acid esters Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- XSIQSWHENMREAF-UHFFFAOYSA-N ethylsulfanylmethanedithioic acid Chemical compound CCSC(S)=S XSIQSWHENMREAF-UHFFFAOYSA-N 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 235000019256 formaldehyde Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- WJXGTMBHOPEHGM-UHFFFAOYSA-N Cl.CCOP(C)(O)=S Chemical compound Cl.CCOP(C)(O)=S WJXGTMBHOPEHGM-UHFFFAOYSA-N 0.000 description 1
- PKUWKAXTAVNIJR-UHFFFAOYSA-N O,O-diethyl hydrogen thiophosphate Chemical compound CCOP(O)(=S)OCC PKUWKAXTAVNIJR-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- UGOLAPHJCTVIEW-UHFFFAOYSA-N chloro-dimethyl-sulfanylidene-$l^{5}-phosphane Chemical compound CP(C)(Cl)=S UGOLAPHJCTVIEW-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- FUWGSUOSJRCEIV-UHFFFAOYSA-N phosphonothioic O,O-acid Chemical compound OP(O)=S FUWGSUOSJRCEIV-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- IFQMTQSXPWHEEG-UHFFFAOYSA-N thiophen-2-ylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CS1 IFQMTQSXPWHEEG-UHFFFAOYSA-N 0.000 description 1
- 239000012989 trithiocarbonate Substances 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
- C07F9/28—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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
-
- 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3211—Esters of acyclic saturated acids which can have 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3258—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3264—Esters with hydroxyalkyl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL136644D NL136644C (un) | 1960-03-09 | ||
| BE600872D BE600872A (un) | 1960-03-09 | ||
| NL262130D NL262130A (un) | 1960-03-09 | ||
| DEF30719A DE1136334B (de) | 1960-03-09 | 1960-03-09 | Verfahren zur Herstellung von Thionothiol- bzw. Thiolphosphon- und -phosphinsaeureestern |
| CH248861A CH381220A (de) | 1960-03-09 | 1961-03-01 | Verfahren zur Herstellung von (Thiono-)Thiolphosphon-(-in-)säureestern |
| FR854548A FR1284773A (fr) | 1960-03-09 | 1961-03-03 | Procédé de préparation d'esters (thiono-) thiolphosphoniques et -phosphiniques |
| GB851461A GB929216A (en) | 1960-03-09 | 1961-03-08 | Process for the production of thiol-and thionothiol-phosphoric and -phosphinic acid esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF30719A DE1136334B (de) | 1960-03-09 | 1960-03-09 | Verfahren zur Herstellung von Thionothiol- bzw. Thiolphosphon- und -phosphinsaeureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1136334B true DE1136334B (de) | 1962-09-13 |
Family
ID=7093886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF30719A Pending DE1136334B (de) | 1960-03-09 | 1960-03-09 | Verfahren zur Herstellung von Thionothiol- bzw. Thiolphosphon- und -phosphinsaeureestern |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE600872A (un) |
| CH (1) | CH381220A (un) |
| DE (1) | DE1136334B (un) |
| GB (1) | GB929216A (un) |
| NL (2) | NL136644C (un) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL276981B1 (en) * | 2018-03-07 | 2023-12-01 | Forschungsverbund Berlin Ev | Chemoselective couplings of thiol with alkene or alkyne-phosphonothiolates and phosphonates |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE835302C (de) * | 1950-02-23 | 1952-03-31 | Farbwerke Hoechst Vormals Meis | Verfahren zur Herstellung von Phosphor und Schwefel enthaltenden organischen Verbindungen |
| DE953795C (de) * | 1955-03-08 | 1956-12-06 | Bayer Ag | Verfahren zur Herstellung von Monothiono-pyrophorsaeure-tetraalkylestern |
-
0
- BE BE600872D patent/BE600872A/xx unknown
- NL NL262130D patent/NL262130A/xx unknown
- NL NL136644D patent/NL136644C/xx active
-
1960
- 1960-03-09 DE DEF30719A patent/DE1136334B/de active Pending
-
1961
- 1961-03-01 CH CH248861A patent/CH381220A/de unknown
- 1961-03-08 GB GB851461A patent/GB929216A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE835302C (de) * | 1950-02-23 | 1952-03-31 | Farbwerke Hoechst Vormals Meis | Verfahren zur Herstellung von Phosphor und Schwefel enthaltenden organischen Verbindungen |
| DE953795C (de) * | 1955-03-08 | 1956-12-06 | Bayer Ag | Verfahren zur Herstellung von Monothiono-pyrophorsaeure-tetraalkylestern |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL276981B1 (en) * | 2018-03-07 | 2023-12-01 | Forschungsverbund Berlin Ev | Chemoselective couplings of thiol with alkene or alkyne-phosphonothiolates and phosphonates |
| IL276981B2 (en) * | 2018-03-07 | 2024-04-01 | Forschungsverbund Berlin Ev | Chemoselective couplings of thiol with alkene or alkyne-phosphonothiolates and phosphonates |
Also Published As
| Publication number | Publication date |
|---|---|
| NL136644C (un) | |
| BE600872A (un) | |
| GB929216A (en) | 1963-06-19 |
| CH381220A (de) | 1964-08-31 |
| NL262130A (un) |
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