GB1237232A - Production of cis-1,2-propenylphosphonic acid - Google Patents
Production of cis-1,2-propenylphosphonic acidInfo
- Publication number
- GB1237232A GB1237232A GB50628/68A GB5062868A GB1237232A GB 1237232 A GB1237232 A GB 1237232A GB 50628/68 A GB50628/68 A GB 50628/68A GB 5062868 A GB5062868 A GB 5062868A GB 1237232 A GB1237232 A GB 1237232A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- cis
- diester
- phosphonic acid
- 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.)
- Expired
Links
- 150000005690 diesters Chemical class 0.000 abstract 9
- 239000002253 acid Substances 0.000 abstract 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 3
- -1 C 2 -C 5 alkenyl alcohol Chemical compound 0.000 abstract 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 3
- 239000000543 intermediate Substances 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 2
- 230000002378 acidificating effect Effects 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 2
- DQTRYXANLKJLPK-UHFFFAOYSA-N chlorophosphonous acid Chemical compound OP(O)Cl DQTRYXANLKJLPK-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004185 ester group Chemical group 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 238000005984 hydrogenation reaction Methods 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 238000000197 pyrolysis Methods 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- XWCIXXXLOAAWPU-IHWYPQMZSA-N [(z)-prop-1-enyl]phosphonic acid Chemical compound C\C=C/P(O)(O)=O XWCIXXXLOAAWPU-IHWYPQMZSA-N 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004599 antimicrobial Substances 0.000 abstract 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical class NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000004803 chlorobenzyl group Chemical group 0.000 abstract 1
- 238000007257 deesterification reaction Methods 0.000 abstract 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical class O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052734 helium Inorganic materials 0.000 abstract 1
- 239000001307 helium Substances 0.000 abstract 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 abstract 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 230000008707 rearrangement Effects 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000004576 sand Substances 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-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)]
- C07F9/40—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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/143—Esters of phosphorous acids with unsaturated acyclic alcohols
-
- 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
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/146—Esters of phosphorous acids containing P-halide groups
-
- 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
- C07F9/3826—Acyclic unsaturated acids
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72944768A | 1968-05-15 | 1968-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1237232A true GB1237232A (en) | 1971-06-30 |
Family
ID=24931069
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB50628/68A Expired GB1237232A (en) | 1968-05-15 | 1968-10-24 | Production of cis-1,2-propenylphosphonic acid |
Country Status (17)
| Country | Link |
|---|---|
| AT (1) | AT300829B (nl) |
| BE (1) | BE723076A (nl) |
| CH (1) | CH531013A (nl) |
| DK (1) | DK135996B (nl) |
| ES (1) | ES359534A1 (nl) |
| FI (1) | FI51356C (nl) |
| FR (1) | FR1590372A (nl) |
| GB (1) | GB1237232A (nl) |
| IE (1) | IE32524B1 (nl) |
| IL (1) | IL30908A0 (nl) |
| LU (1) | LU57189A1 (nl) |
| MT (1) | MTP589B (nl) |
| NL (1) | NL161762C (nl) |
| NO (1) | NO131032C (nl) |
| OA (1) | OA02915A (nl) |
| SE (1) | SE358890B (nl) |
| ZM (1) | ZM14668A1 (nl) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108558940A (zh) * | 2018-06-01 | 2018-09-21 | 徐州诺克非医药科技有限公司 | 一种中间体丙二烯膦酸的合成方法 |
-
1968
- 1968-10-18 NL NL6814989.A patent/NL161762C/nl active
- 1968-10-21 IE IE1249/68A patent/IE32524B1/xx unknown
- 1968-10-21 IL IL30908A patent/IL30908A0/xx unknown
- 1968-10-21 CH CH1570268A patent/CH531013A/de not_active IP Right Cessation
- 1968-10-24 GB GB50628/68A patent/GB1237232A/en not_active Expired
- 1968-10-25 ES ES359534A patent/ES359534A1/es not_active Expired
- 1968-10-29 DK DK522468AA patent/DK135996B/da unknown
- 1968-10-29 SE SE14613/68A patent/SE358890B/xx unknown
- 1968-10-29 FI FI683061A patent/FI51356C/fi active
- 1968-10-29 LU LU57189D patent/LU57189A1/xx unknown
- 1968-10-29 BE BE723076D patent/BE723076A/xx unknown
- 1968-10-29 NO NO4284/68A patent/NO131032C/no unknown
- 1968-10-30 FR FR1590372D patent/FR1590372A/fr not_active Expired
- 1968-10-30 OA OA53403A patent/OA02915A/xx unknown
- 1968-10-30 ZM ZM146/68A patent/ZM14668A1/xx unknown
- 1968-10-30 AT AT1056468A patent/AT300829B/de not_active IP Right Cessation
- 1968-11-26 MT MT589A patent/MTP589B/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108558940A (zh) * | 2018-06-01 | 2018-09-21 | 徐州诺克非医药科技有限公司 | 一种中间体丙二烯膦酸的合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| IL30908A0 (en) | 1968-12-26 |
| NL161762B (nl) | 1979-10-15 |
| IE32524L (en) | 1969-11-15 |
| NO131032B (nl) | 1974-12-16 |
| IE32524B1 (en) | 1973-09-05 |
| CH531013A (de) | 1972-11-30 |
| AT300829B (de) | 1972-08-10 |
| ES359534A1 (es) | 1970-10-16 |
| DK135996B (da) | 1977-07-25 |
| MTP589B (en) | 1970-10-23 |
| OA02915A (fr) | 1970-12-15 |
| LU57189A1 (nl) | 1969-05-16 |
| BE723076A (nl) | 1969-04-29 |
| FI51356C (fi) | 1976-12-10 |
| DE1805674A1 (de) | 1969-12-11 |
| NL161762C (nl) | 1980-03-17 |
| FI51356B (nl) | 1976-08-31 |
| DE1805674B2 (de) | 1973-01-04 |
| DK135996C (nl) | 1978-01-09 |
| NL6814989A (nl) | 1969-11-18 |
| FR1590372A (nl) | 1970-04-13 |
| SE358890B (nl) | 1973-08-13 |
| ZM14668A1 (en) | 1970-06-18 |
| NO131032C (nl) | 1975-03-25 |
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