GB943731A - Novel tertiary spiro phosphites and their production - Google Patents
Novel tertiary spiro phosphites and their productionInfo
- Publication number
- GB943731A GB943731A GB30398/62A GB3039862A GB943731A GB 943731 A GB943731 A GB 943731A GB 30398/62 A GB30398/62 A GB 30398/62A GB 3039862 A GB3039862 A GB 3039862A GB 943731 A GB943731 A GB 943731A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chlorpropyl
- tris
- groups
- spiro
- alkyl groups
- 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 spiro phosphites Chemical group 0.000 title abstract 7
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 239000007983 Tris buffer Substances 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 2
- 239000004014 plasticizer Substances 0.000 abstract 2
- 229920005989 resin Polymers 0.000 abstract 2
- 239000011347 resin Substances 0.000 abstract 2
- 239000003381 stabilizer Substances 0.000 abstract 2
- YYTSGNJTASLUOY-UHFFFAOYSA-N 1-chloropropan-2-ol Chemical compound CC(O)CCl YYTSGNJTASLUOY-UHFFFAOYSA-N 0.000 abstract 1
- VZIQXGLTRZLBEX-UHFFFAOYSA-N 2-chloro-1-propanol Chemical compound CC(Cl)CO VZIQXGLTRZLBEX-UHFFFAOYSA-N 0.000 abstract 1
- BXJCEULFBLJODE-UHFFFAOYSA-N 2-chloroethyl dihydrogen phosphite Chemical class OP(O)OCCCl BXJCEULFBLJODE-UHFFFAOYSA-N 0.000 abstract 1
- KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- VXTFGYMINLXJPW-UHFFFAOYSA-N phosphinane Chemical compound C1CCPCC1 VXTFGYMINLXJPW-UHFFFAOYSA-N 0.000 abstract 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
-
- 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
-
- 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
- C07F9/65742—Esters of oxyacids of phosphorus non-condensed with carbocyclic rings or heterocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/527—Cyclic esters
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)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Abstract
The invention comprises spirophosphites of the formula: <FORM:0943731/C2/1> wherein R1 and R2 are 2-chlorpropyl groups or C6-C18 alkyl groups. The compounds in which R1 and R2 2-chlorpropyl groups may be obtained by transesterifying one mole of pentaerythritol with at least two moles of tris-2-chlorpropyl phosphite and the compounds in which R1 and R2 are C6-C18 alkyl groups ma be obtained by esterifying either a bis-(phenoxy) spiro-1,3,2-dioxa phosphorinane or a bis-(2-chloralkoxy) spiro-1,3,2-dioxa phosphorinane with a C6-C18 alkanol at least two moles of alkanol being used per mole of the phosphorinane. The first reaction may be effected at from room temperature to the boiling point of 2-chloro-1-propanol at the pressure employed and the reaction can be carried out at atmospheric or sub-atmospheric pressure, the latter, (e.g. a pressure of 50 mm Hg) being preferred. The propylene chlorhydrin formed is distilled off and the desired phosphite recovered. Catalysts may be used e.g. alkali metal alkoxides or phenates, or tris 2-chloropropyl, tris 2-chloro-butyl- or tris 2-chloroethyl-phosphites. Examples are given for the production of products in which R1 and R2 are 2-chlorpropyl, n decyl, hexyl, 2-ethylhexyl, lauryl and stearyl respectively. The products are useful as insecticides and as stabilizers and plasticizers for vinyl chloride resins (see Division C3).ALSO:Spirophosphites of the general formula: <FORM:0943731/C3/1> wherein R1 and R2 are 2-chloropropyl groups or C6-C18 alkyl groups (see Division C2) may be used as stabilizers and plasticizers for vinyl chloride resins.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4888A US2961454A (en) | 1960-01-27 | 1960-01-27 | Ester interchange |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB943731A true GB943731A (en) | 1963-12-04 |
Family
ID=21713021
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1781/61A Expired GB944726A (en) | 1960-01-27 | 1961-01-16 | The production of tertiary phosphites including new cyclic phosphites |
| GB30398/62A Expired GB943731A (en) | 1960-01-27 | 1961-01-16 | Novel tertiary spiro phosphites and their production |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1781/61A Expired GB944726A (en) | 1960-01-27 | 1961-01-16 | The production of tertiary phosphites including new cyclic phosphites |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2961454A (en) |
| GB (2) | GB944726A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4209340A (en) * | 1977-03-14 | 1980-06-24 | Daicel Ltd. | Cellulose ester resin composition |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3189545A (en) * | 1965-06-15 | Lubricating composition | ||
| US3205269A (en) * | 1960-05-10 | 1965-09-07 | Union Carbide Corp | Stabilization of ethers with phosphorous compounds |
| US3047608A (en) * | 1960-09-15 | 1962-07-31 | Weston Chemical Corp | Phosphites |
| US3081331A (en) * | 1961-08-07 | 1963-03-12 | Weston Chemical Corp | Poly phosphorus ester condensates and their preparation |
| US3053878A (en) * | 1961-05-23 | 1962-09-11 | Weston Chemical Corp | Pentaerythritol phosphite esters |
| NL282705A (en) * | 1961-09-01 | |||
| US3153036A (en) * | 1961-09-04 | 1964-10-13 | Bayer Ag | Phosphorous acid esters derived from transesterification of phosphite triesters with mono-, di-, and trisaccharides |
| US3205250A (en) * | 1961-11-20 | 1965-09-07 | Hooker Chemical Corp | 3, 9-alkoxy and 3, 9-chloropropyl-2, 4, 8, 10-tetraoxa-3, 9-phosphospiro (6, 6) hendeanes |
| US3192243A (en) * | 1962-04-10 | 1965-06-29 | Delaware Chemicals Inc | Phosphorous derivatives of pentaerythritol |
| US3201437A (en) * | 1962-06-11 | 1965-08-17 | Union Carbide Corp | Neoalkyl phosphites |
| US3179689A (en) * | 1962-08-28 | 1965-04-20 | Union Carbide Corp | Chloro compounds prepared by reacting a trimethyloalkane and phosphorus trichloride |
| US4290976A (en) * | 1975-03-24 | 1981-09-22 | Borg-Warner Chemicals, Inc. | Process for the preparation of phenol-free phosphites |
| US4064100A (en) * | 1975-07-22 | 1977-12-20 | Weston Chemical Co., Inc. | Friable distearyl pentaerythritol diphosphite |
| DE2633393C3 (en) * | 1976-07-24 | 1980-02-07 | Hoechst Ag, 6000 Frankfurt | Cyclic phosphites of polyalcohols, their manufacture and use |
| US4665211A (en) * | 1985-12-03 | 1987-05-12 | Borg-Warner Chemicals, Inc. | Process for preparing bis(dialkylphenyl) pentaerythritol diphosphites |
| US6451888B1 (en) | 1994-06-01 | 2002-09-17 | General Electric Company | Solid stabilizer composition with improved hydrolytic stability |
| AU2003292814A1 (en) * | 2003-01-06 | 2004-07-29 | Teijin Chemicals Ltd. | Process for the production of pentaerythritol diphosphonates |
| JP5069436B2 (en) * | 2006-07-24 | 2012-11-07 | 帝人株式会社 | Method for producing aliphatic phosphite |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2883411A (en) * | 1953-06-18 | 1959-04-21 | Union Carbide Corp | Production of heterocyclic phosphoruscontaining compounds |
| US2841608A (en) * | 1956-05-21 | 1958-07-01 | Shea Chemical Corp | Cyclic glycol phosphites |
| US2834798A (en) * | 1957-12-20 | 1958-05-13 | Shea Chemical Corp | Heterocyclic phosphorus compounds |
-
1960
- 1960-01-27 US US4888A patent/US2961454A/en not_active Expired - Lifetime
-
1961
- 1961-01-16 GB GB1781/61A patent/GB944726A/en not_active Expired
- 1961-01-16 GB GB30398/62A patent/GB943731A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4209340A (en) * | 1977-03-14 | 1980-06-24 | Daicel Ltd. | Cellulose ester resin composition |
Also Published As
| Publication number | Publication date |
|---|---|
| GB944726A (en) | 1963-12-18 |
| US2961454A (en) | 1960-11-22 |
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