GB810646A - A process for the production of o.o-dialkylphosphoric or o.o-dialkylthionophosphoric acid esters of n-alkylol-lactams - Google Patents
A process for the production of o.o-dialkylphosphoric or o.o-dialkylthionophosphoric acid esters of n-alkylol-lactamsInfo
- Publication number
- GB810646A GB810646A GB17303/57A GB1730357A GB810646A GB 810646 A GB810646 A GB 810646A GB 17303/57 A GB17303/57 A GB 17303/57A GB 1730357 A GB1730357 A GB 1730357A GB 810646 A GB810646 A GB 810646A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid chloride
- methylol
- thionophosphoric
- alkylol
- represent
- 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
- 150000002148 esters Chemical class 0.000 title abstract 3
- 239000002253 acid Substances 0.000 title abstract 2
- 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 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- -1 chlorphenyl Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical group 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- QBUDWHWPQWURCC-UHFFFAOYSA-N 1-(hydroxymethyl)azepan-2-one Chemical compound OCN1CCCCCC1=O QBUDWHWPQWURCC-UHFFFAOYSA-N 0.000 abstract 1
- LEYRRKPTVVUCIC-UHFFFAOYSA-N 1-(hydroxymethyl)piperidin-2-one Chemical compound OCN1CCCCC1=O LEYRRKPTVVUCIC-UHFFFAOYSA-N 0.000 abstract 1
- PJEXUIKBGBSHBS-UHFFFAOYSA-N 1-(hydroxymethyl)pyrrolidin-2-one Chemical compound OCN1CCCC1=O PJEXUIKBGBSHBS-UHFFFAOYSA-N 0.000 abstract 1
- JTYIGLPDXIQUDU-UHFFFAOYSA-N 1-(hydroxymethyl)pyrrolidine-2-thione Chemical compound C(O)N1C(CCC1)=S JTYIGLPDXIQUDU-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract 1
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N Caprolactam Natural products O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000006501 nitrophenyl group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 abstract 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
- B03D—FLOTATION; DIFFERENTIAL SEDIMENTATION
- B03D1/00—Flotation
- B03D1/001—Flotation agents
- B03D1/004—Organic compounds
- B03D1/014—Organic compounds containing phosphorus
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Phosphoric and thionophosphoric esters of N-alkylol-lactams of the general formula <FORM:0810646/IV (b)/1> in which R and R1 represent C1-4 alkyl groups, X represents O or S, R3 and R4 represent H or alkyl, especially C1-4, which may be substituted by halogen, especially chlorine, or alkenyl, cycloalkyl or aryl radicals such as phenyl, chlorphenyl or nitrophenyl and n and m are integers, n being 1 to 4 and m 3 to 7, are prepared by reacting a compound <FORM:0810646/IV (b)/2> where Hal represents halogen, especially chlorine, with a N-alkylol-lactam <FORM:0810646/IV (b)/3> in an anhydrous medium at 10 DEG to 100 DEG C., advantageously in the presence of an acidbinding agent such as heterocyclic or tertiary amines or alkali metal carbonates or bicarbonates. Many suitable starting materials are specified. The products in which R and R1 represent C1-4 alkyl and R3 and R4 hydrogen, methyl or trichlormethyl are claimed per se. The reaction may be effected in a solvent such as a hydrocarbon, chlorohydrocarbon, ketone or ether, many being specified. The products are insecticides. Examples describe the preparation of esters from O,O-diethyl-thionophosphoric acid chloride, O,O-diethyl-phosphoric acid chloride, O,O-dimethyl-thionophosphoric acid chloride, O,O-di-n-propylthionophosphoric acid chloride, O,O - di - iso - propyl - thionophosphoric acid chloride or O,O-di-n-butyl-thionophosphoric acid chloride and N-methylol-pyrrolidone - 2, N - b - hydroxyethyl - pyrrolidone - 2, N - methylol - caprolactam, N - methylol - caprylic lactam, N - methylol - thiopyrrolidone - 2, N - methylol - piperidone - 2 or N - (a - hydroxy - b ,b ,b - trichlorethyl) - caprolactam; acid-binding agents used are pyridine, triethylamine, tripropylamine, potassium carbonate and sodium carbonate; solvents are benzene and chloroform.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE810646X | 1956-06-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB810646A true GB810646A (en) | 1959-03-18 |
Family
ID=6725366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17303/57A Expired GB810646A (en) | 1956-06-05 | 1957-05-31 | A process for the production of o.o-dialkylphosphoric or o.o-dialkylthionophosphoric acid esters of n-alkylol-lactams |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB810646A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105170338A (en) * | 2015-08-28 | 2015-12-23 | 张好勇 | Non-sulfide mineral flotation collector, preparation method thereof and application thereof |
| CN110605184A (en) * | 2019-05-30 | 2019-12-24 | 核工业北京化工冶金研究院 | Flotation collector for uranium asphalt ore and application thereof |
-
1957
- 1957-05-31 GB GB17303/57A patent/GB810646A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105170338A (en) * | 2015-08-28 | 2015-12-23 | 张好勇 | Non-sulfide mineral flotation collector, preparation method thereof and application thereof |
| CN110605184A (en) * | 2019-05-30 | 2019-12-24 | 核工业北京化工冶金研究院 | Flotation collector for uranium asphalt ore and application thereof |
| CN110605184B (en) * | 2019-05-30 | 2021-11-30 | 核工业北京化工冶金研究院 | Flotation collector for uranium asphalt ore and application thereof |
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