GB974988A - Process for the preparation of alpha, beta-unsaturated phosphonic acid esters - Google Patents
Process for the preparation of alpha, beta-unsaturated phosphonic acid estersInfo
- Publication number
- GB974988A GB974988A GB664663A GB664663A GB974988A GB 974988 A GB974988 A GB 974988A GB 664663 A GB664663 A GB 664663A GB 664663 A GB664663 A GB 664663A GB 974988 A GB974988 A GB 974988A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diethyl
- aryl
- phosphonate
- cycloalkyl
- alkyl
- 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
- 150000003008 phosphonic acid esters Chemical class 0.000 title 1
- -1 heterocyclic radical Chemical class 0.000 abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- KGWLPYVMUWAOJC-QPJJXVBHSA-N (e)-1-diethoxyphosphorylbut-2-ene Chemical compound CCOP(=O)(OCC)C\C=C\C KGWLPYVMUWAOJC-QPJJXVBHSA-N 0.000 abstract 1
- KDBATBQFNNDWCG-UHFFFAOYSA-N 1-[butoxy(prop-2-enyl)phosphoryl]oxybutane Chemical compound CCCCOP(=O)(CC=C)OCCCC KDBATBQFNNDWCG-UHFFFAOYSA-N 0.000 abstract 1
- LKZVEBMWBIQOFK-UHFFFAOYSA-N 1-diethoxyphosphorylcyclohexene Chemical compound CCOP(=O)(OCC)C1=CCCCC1 LKZVEBMWBIQOFK-UHFFFAOYSA-N 0.000 abstract 1
- PALUACDGXDYFOY-UHFFFAOYSA-N 1-diethoxyphosphorylcyclopentene Chemical compound CCOP(=O)(OCC)C1=CCCC1 PALUACDGXDYFOY-UHFFFAOYSA-N 0.000 abstract 1
- YPJHXRAHMUKXAE-UHFFFAOYSA-N 3-diethoxyphosphorylprop-1-ene Chemical compound CCOP(=O)(CC=C)OCC YPJHXRAHMUKXAE-UHFFFAOYSA-N 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- 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
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic 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
- C07F9/38—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
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4015—Esters of acyclic unsaturated acids
-
- 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
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4018—Esters of cycloaliphatic acids
-
- 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
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4025—Esters of poly(thio)phosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
- C10M2223/065—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds containing sulfur
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)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
Abstract
Alpha, beta-unsaturated phosphonic esters of formula <FORM:0974988/C1/1> where R is alkyl, cycloalkyl or aryl or both Rs together form a divalent organic radical, R1 is an alkyl, substituted or unsubstituted aryl, cycloalkyl or heterocyclic radical, each of R2 and R3 is hydrogen, alkyl, aryl, cycloalkyl or a heterocyclic radical and may be the same or different, or R1 and R2 together form part of an organic ring system, are prepared by reacting a compound <FORM:0974988/C1/2> with thionyl chloride in a non-alkaline medium. An excess, e.g. 3-50% of thionyl chloride may be used. Inert organic solvents may be used and temperatures of 10-90 DEG C. A specified substituted aryl radical is p-chloro-phenyl and a specified heterocyclic radical is thienyl. The invention also comprises the following compounds: diethyl 2-propenyl-phosphonate; diethyl 2-butenylphosphonate; diethyl cyclohexenylphosphonate; diethyl cyclopentenylphosphonate; and diethyl 2-methylpentenyl -4- phosphonate and the cis and trans isomers thereof. Di-n-butyl 2-propenyl-phosphonate is also prepared.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DES78144A DE1159443B (en) | 1962-02-21 | 1962-02-21 | Process for the production of ª ‡, ª ‰ -unsaturated phosphonic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB974988A true GB974988A (en) | 1964-11-11 |
Family
ID=7507263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB664663A Expired GB974988A (en) | 1962-02-21 | 1963-02-19 | Process for the preparation of alpha, beta-unsaturated phosphonic acid esters |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1159443B (en) |
| GB (1) | GB974988A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6429329B1 (en) | 1995-02-10 | 2002-08-06 | Akzo Nobel Nv | Synthesis of a hydrocarbylvinylphosphonic acid hydrocarbyl ester |
-
1962
- 1962-02-21 DE DES78144A patent/DE1159443B/en active Pending
-
1963
- 1963-02-19 GB GB664663A patent/GB974988A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6429329B1 (en) | 1995-02-10 | 2002-08-06 | Akzo Nobel Nv | Synthesis of a hydrocarbylvinylphosphonic acid hydrocarbyl ester |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1159443B (en) | 1963-12-19 |
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