FR2279757A1 - Dialkyl esters of aromatic phosphonic acids prepd. - from trialkyl phosphite and activated halogenated aromatic pd. opt. in solvent with tert.-amine catalyst - Google Patents
Dialkyl esters of aromatic phosphonic acids prepd. - from trialkyl phosphite and activated halogenated aromatic pd. opt. in solvent with tert.-amine catalystInfo
- Publication number
- FR2279757A1 FR2279757A1 FR7513855A FR7513855A FR2279757A1 FR 2279757 A1 FR2279757 A1 FR 2279757A1 FR 7513855 A FR7513855 A FR 7513855A FR 7513855 A FR7513855 A FR 7513855A FR 2279757 A1 FR2279757 A1 FR 2279757A1
- Authority
- FR
- France
- Prior art keywords
- aromatic
- opt
- prepd
- ester
- phosphonic acids
- 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.)
- Withdrawn
Links
- 150000002148 esters Chemical class 0.000 title abstract 5
- 125000003118 aryl group Chemical group 0.000 title abstract 4
- -1 aromatic phosphonic acids Chemical class 0.000 title abstract 3
- 239000003054 catalyst Substances 0.000 title abstract 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 title abstract 2
- 239000002904 solvent Substances 0.000 title abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 230000003213 activating effect Effects 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 150000008301 phosphite esters Chemical class 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 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
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4021—Esters of aromatic acids (P-C aromatic linkage)
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Dialkyl esters of aromatic phosphonic acids are prepd. by the addn. of a trialkyl phosphite to an activated halogenated aromatic cpd. opt. in soln. and/or contg. a catalyst at 0-150 degrees C the addn. being performed in portions such that the reaction mixt. is kept at a temp. >70 degrees C. The molar ratio of aromatic cpd. to phosphite ester is 0.9-3:1; and the reaction is stopped when the calculated amt. of alkyl halide has been liberated. Opt. the excess solvent is removed by vacuum distn. or after distn. the phosphonic ester is extracted with petroleum ether. The aromatic cpd. pref. carries one or more nitro gps. in the ortho- and/or para posn. to the halogen arom. Other pref. activating gps are halo, CF3, cyano, sulphonic, carbonyl, carboxyl, carboxylic ester and sulphonic ester. High yields of phosphonic esters are obtd. practically free of by-prods.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742421070 DE2421070A1 (en) | 1974-05-02 | 1974-05-02 | PROCESS FOR THE PREPARATION OF DIALKYLESTERS OF AROMATIC PHOSPHONIC ACIDS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2279757A1 true FR2279757A1 (en) | 1976-02-20 |
Family
ID=5914401
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7513855A Withdrawn FR2279757A1 (en) | 1974-05-02 | 1975-05-02 | Dialkyl esters of aromatic phosphonic acids prepd. - from trialkyl phosphite and activated halogenated aromatic pd. opt. in solvent with tert.-amine catalyst |
| FR7600268A Withdrawn FR2288101A1 (en) | 1974-05-02 | 1976-01-07 | DIALKYL ESTERS OF AROMATIC PHOSPHONIC ACIDS |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7600268A Withdrawn FR2288101A1 (en) | 1974-05-02 | 1976-01-07 | DIALKYL ESTERS OF AROMATIC PHOSPHONIC ACIDS |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE828539A (en) |
| DE (1) | DE2421070A1 (en) |
| FR (2) | FR2279757A1 (en) |
| NL (1) | NL7505102A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2829710A1 (en) * | 1978-07-06 | 1980-01-17 | Bayer Ag | METHOD FOR PRODUCING AROMATIC PHOSPHORUS COMPOUNDS |
-
1974
- 1974-05-02 DE DE19742421070 patent/DE2421070A1/en active Pending
-
1975
- 1975-04-29 NL NL7505102A patent/NL7505102A/en unknown
- 1975-04-29 BE BE155907A patent/BE828539A/en unknown
- 1975-05-02 FR FR7513855A patent/FR2279757A1/en not_active Withdrawn
-
1976
- 1976-01-07 FR FR7600268A patent/FR2288101A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| BE828539A (en) | 1975-10-29 |
| NL7505102A (en) | 1975-11-04 |
| DE2421070A1 (en) | 1975-11-20 |
| FR2288101A1 (en) | 1976-05-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |