GB1147179A - Preparation of 1-halo-phosphonic acids and their esters - Google Patents
Preparation of 1-halo-phosphonic acids and their estersInfo
- Publication number
- GB1147179A GB1147179A GB5256966A GB5256966A GB1147179A GB 1147179 A GB1147179 A GB 1147179A GB 5256966 A GB5256966 A GB 5256966A GB 5256966 A GB5256966 A GB 5256966A GB 1147179 A GB1147179 A GB 1147179A
- Authority
- GB
- United Kingdom
- Prior art keywords
- stage
- phosphorus
- chloride
- esters
- halo
- 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
- 238000002360 preparation method Methods 0.000 title abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- 229910052698 phosphorus Inorganic materials 0.000 abstract 3
- 239000011574 phosphorus Substances 0.000 abstract 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 2
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 abstract 2
- 150000001299 aldehydes Chemical class 0.000 abstract 2
- -1 aralkyl aldehyde Chemical class 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 2
- 229920002866 paraformaldehyde Polymers 0.000 abstract 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- 235000005074 zinc chloride Nutrition 0.000 abstract 2
- 239000011592 zinc chloride Substances 0.000 abstract 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- 229910015900 BF3 Inorganic materials 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 abstract 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 238000006136 alcoholysis reaction Methods 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- MOFCYHDQWIZKMY-UHFFFAOYSA-N chloromethylphosphonic acid Chemical compound OP(O)(=O)CCl MOFCYHDQWIZKMY-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 229940100595 phenylacetaldehyde Drugs 0.000 abstract 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 abstract 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1,147,179. Preparation of 1-halophosphonic acids and their esters. ALBRIGHT & WILSON (MFG.) Ltd. 15 Nov., 1967 [24 Nov., 1966], No. 52569/66. Heading C2C. 1 -Halo-phosphonic acids, or esters thereof, are prepared by (i) reacting a saturated aliphatic, aromatic or aralkyl aldehyde with a tervalent phosphorus halide in a molar ratio of at least 2À5 : 1, (ii) heating the product from stage (i) with a Friedel-Crafts catalyst, and (iii) reacting the product from stage (ii) with water or an alcohol to effect hydrolysis or alcoholysis. The first stage is generally carried out in two steps, the aldehyde and the phosphorus trihalide being first mixed at between 40‹ and 80‹ C. and then heated to between 70‹ and 100‹ C. in the second step. Specified Friedel-Crafts catalysts for use in stage (ii) are zinc chloride, aluminium trichloride, boron trifluoride and stannic chloride. The phosphorus trihalide used may be the chloride, bromide, fluoride or iodide, and if the iodide is used this may be formed in situ from iodine and red phosphorus. Specified aldehydes are formaldehyde, paraformaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, benzaldehyde and phenylacetaldehyde. An example is given for the production of chloromethylphosphonic acid from phosphorus trichloride and paraformaldehyde using zinc chloride as catalyst, methylene chloride and bis-(chloromethyl)-ether being formed as by-products.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5256966A GB1147179A (en) | 1966-11-24 | 1966-11-24 | Preparation of 1-halo-phosphonic acids and their esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5256966A GB1147179A (en) | 1966-11-24 | 1966-11-24 | Preparation of 1-halo-phosphonic acids and their esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1147179A true GB1147179A (en) | 1969-04-02 |
Family
ID=10464424
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5256966A Expired GB1147179A (en) | 1966-11-24 | 1966-11-24 | Preparation of 1-halo-phosphonic acids and their esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1147179A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7750180B2 (en) | 2003-08-22 | 2010-07-06 | Monsanto Technology Llc | Process for the preparation of N-phosphonomethylglycine and derivatives thereof |
-
1966
- 1966-11-24 GB GB5256966A patent/GB1147179A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7750180B2 (en) | 2003-08-22 | 2010-07-06 | Monsanto Technology Llc | Process for the preparation of N-phosphonomethylglycine and derivatives thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Michel | An improved error bound for the compound Poisson approximation of a nearly homogeneous portfolio | |
| GB1147179A (en) | Preparation of 1-halo-phosphonic acids and their esters | |
| GB1312091A (en) | Production of substituted alcohols | |
| Kosolapoff | An improved method of preparation of bis-arylphosphonic acids | |
| Clark et al. | Neighboring group participation in phosphate ester hydrolysis | |
| GB1182212A (en) | Polyenic Alcohols, Aldehydes and Acids | |
| KR850008485A (en) | Method of Making Naproxen | |
| GB1473053A (en) | Process for preparing hydrolyzed ethylene-vinyl acetate copolymer | |
| GB1426650A (en) | Stabilised polyvinyl butyral compositions and additives for polyvinyl butyral | |
| US3060236A (en) | peocess of producing alpha-beta unsatu- | |
| GB1209909A (en) | A long chain hydrocarbon ketone | |
| GB1187233A (en) | Oxymethylene Polymer Production | |
| GB1419182A (en) | Process for preparing 2-substituted-2-cyclopenten-1-ones | |
| GB1051821A (en) | Dimersing acrylonitrile | |
| ES428136A1 (en) | Process for preventing discoloration in hydrolyzed ethylene-vinyl acetate copolymers by exposure to radiation | |
| GB1162899A (en) | Process for the Manufacture of Unsaturated Phosphonic Acid Dichlorides | |
| GB726925A (en) | Improvements in cation-exchange resins | |
| GB1246953A (en) | Polymeric sulphonic acids and salts | |
| GB1237922A (en) | ||
| Collatz et al. | The Activity of Phytase as Determined by the Specific Conductivity of Phytin-Phytase Solutions. | |
| GB1195909A (en) | Process for the Production of Cycloacetal Esters and Cycloketal Esters | |
| GB1204818A (en) | Improvements in or relating to polyvinyl acetate adhesive compositions | |
| GB1252106A (en) | ||
| GB1309331A (en) | Process for preparing methyl and ethyl-10-epoxy-7-preparing methyl and ethyl-10-epoxy-7-ethyl-3,11-dimethyl-2,6-tridecadienoate | |
| IE36184L (en) | Benzodioxan derivatives |