GB770419A - Heterocyclic pyrophosphate esters and the production thereof - Google Patents
Heterocyclic pyrophosphate esters and the production thereofInfo
- Publication number
- GB770419A GB770419A GB30018/54A GB3001854A GB770419A GB 770419 A GB770419 A GB 770419A GB 30018/54 A GB30018/54 A GB 30018/54A GB 3001854 A GB3001854 A GB 3001854A GB 770419 A GB770419 A GB 770419A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxo
- dioxaphosphorinane
- oxy
- bis
- water
- 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
- -1 Heterocyclic pyrophosphate esters Chemical class 0.000 title abstract 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract 3
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 150000003863 ammonium salts Chemical class 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000000725 suspension Substances 0.000 abstract 2
- KQTIIICEAUMSDG-UHFFFAOYSA-N tricarballylic acid Chemical class OC(=O)CC(C(O)=O)CC(O)=O KQTIIICEAUMSDG-UHFFFAOYSA-N 0.000 abstract 2
- HYLUGFQIEIXIFQ-UHFFFAOYSA-N 2-chloro-1,3,2$l^{5}-dioxaphosphinane 2-oxide Chemical compound ClP1(=O)OCCCO1 HYLUGFQIEIXIFQ-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- OTTSLEGAXYCEFL-UHFFFAOYSA-N CCCC1OP(=O)OCC1CC Chemical compound CCCC1OP(=O)OCC1CC OTTSLEGAXYCEFL-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- 150000001279 adipic acids Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- HWSUUGHIDOOOOJ-UHFFFAOYSA-N dioxaphosphinane Chemical compound C1COOPC1 HWSUUGHIDOOOOJ-UHFFFAOYSA-N 0.000 abstract 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical class [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 150000002311 glutaric acids Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000002913 oxalic acids Chemical class 0.000 abstract 1
- GWLJTAJEHRYMCA-UHFFFAOYSA-N phospholane Chemical compound C1CCPC1 GWLJTAJEHRYMCA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 150000003047 pimelic acids Chemical class 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 150000003330 sebacic acids Chemical class 0.000 abstract 1
- MFBOGIVSZKQAPD-UHFFFAOYSA-M sodium butyrate Chemical compound [Na+].CCCC([O-])=O MFBOGIVSZKQAPD-UHFFFAOYSA-M 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003444 succinic acids Chemical class 0.000 abstract 1
- 150000003628 tricarboxylic acids Chemical class 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
- D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
The invention comprises heterocyclic pyrophosphate esters of the formula <FORM:0770419/IV(b)/1> wherein R, R1, R2, R3 and R4 each represent hydrogen or an alkyl group, and n is 0 or 1. The pyrophosphate esters may be prepared by reacting a 2-halo-2-oxo-1,3,2-dioxaphospholane or dioxaphosphorinane <FORM:0770419/IV(b)/2> wherein Hal = chlorine or bromine, under substantially anhydrous conditions with the anhydrous alkali metal or ammonium salt of a saturated mono-, di- or tri-carboxylic acid, at a temperature between 50 DEG and 200 DEG C., preferably 50 DEG and 100 DEG C. The phosphorus-containing reagent is preferably added slowly to a suspension of the salt in an inert solvent for the product. The novel compounds may also be prepared by reacting the above halogeno compound with water in the presence of just enough of a base, preferably pyridine, to take up the hydrogen halide formed. In either preparation, the reaction mixture is washed with water and with aqueous alkali metal bicarbonate and the oily layer is stripped by distillation to a temperature of 100 DEG C. under 2 mm. pressure to remove solvent and water. Suitable salts for use in the first method are alkali metal and ammonium salts of fatty acids having one to 18 carbon atoms, di-salts of oxalic, glutaric, succinic, adipic, pimelic and sebacic acids and tri-salts of tricarballylic acid. According to examples, to a suspension of anhydrous sodium acetate in toluene at 100 DEG C. is added the appropriate 2-chloro-2-oxo-1,3,2-dioxaphosphorinane or phospholane to give (1) 2,21-oxy-bis (2-oxo-4-propyl - 5 - ethyl - 1,3,2 - dioxaphosphorinane); (2) 2,21 - oxy - bis (2 - oxo - 4 - methyl - 1,3,2 - dioxaphospholane); (3) 2,21 - oxy - bis (2 - oxo - 5 - 5 - butyl - 5 - ethyl - 1,3,2 - dioxaphosphorinane); (4) 2,21 - oxy - bis (2 - oxo - 5,5 - diethyl - 1,3,2 - dioxaphosphorinane); (5) 2,21 - oxy - bis (2 - oxo - methyl - 1,3,2 - dioxaphosphorinane); (6) 2,21 - oxy - bis (2 - oxo - 4,6 - dimethyl - 1,3,2-dioxaphosphorinane). In Example (7) sodium butyrate in toluene is used giving the same product as (1)); (8) the halo-oxo-dioxaphosphorinane is dissolved in benzene, water and pyridine are added thereto and the mixture is heated, giving the same product as (1). The products may be useful as plasticisers, as dyeing assistants and in biological applications.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US770419XA | 1953-10-27 | 1953-10-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB770419A true GB770419A (en) | 1957-03-20 |
Family
ID=22135740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB30018/54A Expired GB770419A (en) | 1953-10-27 | 1954-10-19 | Heterocyclic pyrophosphate esters and the production thereof |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1009634B (en) |
| GB (1) | GB770419A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2532521A1 (en) * | 1974-07-30 | 1976-02-19 | Sandoz Ag | POLYMERIC MATERIALS AND THEIR PRODUCTION |
| WO2022092835A1 (en) * | 2020-10-29 | 2022-05-05 | 솔브레인 주식회사 | Method for preparing phosphate-based symmetric compound |
-
1954
- 1954-10-19 GB GB30018/54A patent/GB770419A/en not_active Expired
- 1954-10-22 DE DEU3048A patent/DE1009634B/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2532521A1 (en) * | 1974-07-30 | 1976-02-19 | Sandoz Ag | POLYMERIC MATERIALS AND THEIR PRODUCTION |
| US4220472A (en) | 1974-07-30 | 1980-09-02 | Sandoz Ltd. | Dioxaphosphorinane derivatives as flameproofing agents |
| WO2022092835A1 (en) * | 2020-10-29 | 2022-05-05 | 솔브레인 주식회사 | Method for preparing phosphate-based symmetric compound |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1009634B (en) | 1957-06-06 |
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