DE1114478B - Verfahren zur Herstellung von Monothio- bzw. Dithiophosphor- und -phosphonsaeureestern - Google Patents
Verfahren zur Herstellung von Monothio- bzw. Dithiophosphor- und -phosphonsaeureesternInfo
- Publication number
- DE1114478B DE1114478B DEF31397A DEF0031397A DE1114478B DE 1114478 B DE1114478 B DE 1114478B DE F31397 A DEF31397 A DE F31397A DE F0031397 A DEF0031397 A DE F0031397A DE 1114478 B DE1114478 B DE 1114478B
- Authority
- DE
- Germany
- Prior art keywords
- acid
- mol
- alkyl
- acids
- ester
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 48
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 39
- 239000002253 acid Substances 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 8
- 235000011152 sodium sulphate Nutrition 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- -1 benzene thiosulfonic acid S- (4-nitrophenyl) ester Chemical compound 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- 230000007935 neutral effect Effects 0.000 claims description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- 239000003921 oil Substances 0.000 description 10
- 238000009835 boiling Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000013078 crystal Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 150000003008 phosphonic acid esters Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HKRKZYSYVNYGRL-UHFFFAOYSA-N 1-chloro-4-(4-chlorophenyl)sulfonylsulfanylbenzene Chemical compound C1=CC(Cl)=CC=C1SS(=O)(=O)C1=CC=C(Cl)C=C1 HKRKZYSYVNYGRL-UHFFFAOYSA-N 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- YLPFDPQWYRCEJQ-UHFFFAOYSA-N ethoxy-(3-ethylthiophen-2-yl)phosphinous acid Chemical compound C(C)OP(O)C=1SC=CC1CC YLPFDPQWYRCEJQ-UHFFFAOYSA-N 0.000 description 1
- CJJJINZRFGBPII-UHFFFAOYSA-N ethylsulfanylsulfonylbenzene Chemical compound CCSS(=O)(=O)C1=CC=CC=C1 CJJJINZRFGBPII-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 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
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
-
- 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
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/17—Esters of thiophosphoric acids with hydroxyalkyl 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl 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)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL137592D NL137592C (enrdf_load_html_response) | 1960-06-07 | ||
BE604698D BE604698A (enrdf_load_html_response) | 1960-06-07 | ||
NL265597D NL265597A (enrdf_load_html_response) | 1960-06-07 | ||
DEF31397A DE1114478B (de) | 1960-06-07 | 1960-06-07 | Verfahren zur Herstellung von Monothio- bzw. Dithiophosphor- und -phosphonsaeureestern |
CH622661A CH408913A (de) | 1960-06-07 | 1961-05-29 | Verfahren zur Herstellung von Monothio- bzw. Dithiophosphor- und -phosphonsäureestern |
DK186664A DK105526C (da) | 1960-06-07 | 1961-06-06 | Fremgangsmåde til fremstilling af monothio- eller dithiophosphor- eller -phosphonsyreestere. |
GB2061461A GB917438A (en) | 1960-06-07 | 1961-06-07 | Process for the production of monothio- and dithiophosphoric and phosphonic acid esters |
FR864193A FR1292494A (fr) | 1960-06-07 | 1961-06-07 | Procédé de préparation d'esters monothio- ou dithiophosphoriques et -phosphoniques |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF31397A DE1114478B (de) | 1960-06-07 | 1960-06-07 | Verfahren zur Herstellung von Monothio- bzw. Dithiophosphor- und -phosphonsaeureestern |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1114478B true DE1114478B (de) | 1961-10-05 |
Family
ID=7094169
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF31397A Pending DE1114478B (de) | 1960-06-07 | 1960-06-07 | Verfahren zur Herstellung von Monothio- bzw. Dithiophosphor- und -phosphonsaeureestern |
Country Status (6)
Country | Link |
---|---|
BE (1) | BE604698A (enrdf_load_html_response) |
CH (1) | CH408913A (enrdf_load_html_response) |
DE (1) | DE1114478B (enrdf_load_html_response) |
DK (1) | DK105526C (enrdf_load_html_response) |
GB (1) | GB917438A (enrdf_load_html_response) |
NL (2) | NL265597A (enrdf_load_html_response) |
-
0
- BE BE604698D patent/BE604698A/xx unknown
- NL NL137592D patent/NL137592C/xx active
- NL NL265597D patent/NL265597A/xx unknown
-
1960
- 1960-06-07 DE DEF31397A patent/DE1114478B/de active Pending
-
1961
- 1961-05-29 CH CH622661A patent/CH408913A/de unknown
- 1961-06-06 DK DK186664A patent/DK105526C/da active
- 1961-06-07 GB GB2061461A patent/GB917438A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
BE604698A (enrdf_load_html_response) | |
NL265597A (enrdf_load_html_response) | |
DK105526C (da) | 1966-10-10 |
CH408913A (de) | 1966-03-15 |
GB917438A (en) | 1963-02-06 |
NL137592C (enrdf_load_html_response) |
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