GB1580603A - Process for preparing triorgano-(2,5-dihydroxyphenyl) phosphonium salts - Google Patents
Process for preparing triorgano-(2,5-dihydroxyphenyl) phosphonium salts Download PDFInfo
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- GB1580603A GB1580603A GB2057478A GB2057478A GB1580603A GB 1580603 A GB1580603 A GB 1580603A GB 2057478 A GB2057478 A GB 2057478A GB 2057478 A GB2057478 A GB 2057478A GB 1580603 A GB1580603 A GB 1580603A
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- Prior art keywords
- dihydroxyphenyl
- reaction
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- tri
- glycol
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- 150000004714 phosphonium salts Chemical class 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 28
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 24
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000000376 reactant Substances 0.000 claims description 14
- -1 tri-substituted (2,5 dihydroxyphenyl)phosphonium Chemical class 0.000 claims description 14
- 239000003822 epoxy resin Substances 0.000 claims description 12
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 12
- 229920000647 polyepoxide Polymers 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 150000001450 anions Chemical class 0.000 claims description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 239000012429 reaction media Substances 0.000 claims description 6
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 claims description 5
- 230000008014 freezing Effects 0.000 claims description 4
- 238000007710 freezing Methods 0.000 claims description 4
- 150000002334 glycols Chemical class 0.000 claims description 4
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 claims description 3
- 229940089960 chloroacetate Drugs 0.000 claims description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- 229940106691 bisphenol a Drugs 0.000 claims description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000011833 salt mixture Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CRAIKLYPQMVHAD-UHFFFAOYSA-N 2-phosphanylbenzene-1,4-diol Chemical class OC1=CC=C(O)C(P)=C1 CRAIKLYPQMVHAD-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000002118 epoxides Chemical group 0.000 description 2
- 150000002989 phenols Chemical group 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 229910004039 HBF4 Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- NLEPUYHEOSKYJK-UHFFFAOYSA-O tributyl-(2,5-dihydroxyphenyl)phosphanium Chemical class CCCC[P+](CCCC)(CCCC)C1=CC(O)=CC=C1O NLEPUYHEOSKYJK-UHFFFAOYSA-O 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/688—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5442—Aromatic phosphonium compounds (P-C aromatic linkage)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Epoxy Resins (AREA)
Description
(54) PROCESS FOR PREPARING TRIORGANO
(2,5-DIHYDROXYPHENYL) PHOSPHONIUM SALTS
(71) We, THE DOW CHEMICAL COMPANY, a Corporation organised and existing under the laws of the State of Delaware, United States of America, of
Midland, County of Midland, State of Michigan, United States of America, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:- Tri-substituted (2,5 - dihydroxyphenyl)phosphonium salts are known as latent catalysts for promoting the reaction between vicinal epoxides and phenols and/or carboxylic acids (or anhydrides). Pre-catalyzed epoxy resins are easily prepared using such catalysts.
Such compounds were previously prepared by first reacting the appropriate tri-substituted phosphine with p-benzoquinone in benzene solution to form a phosphobetaine. This method was described by Ramirez et al., J. Am. Chem. Soc.,
Vol. 78, 5614 (1956). In this reference, the phosphobetaine was obtained as a solid precipitate which was isolated and subsequently converted to the corresponding phosphonium salt by reaction with an aqueous protic acid or a methanol/water solution of the acid.
This invention is directed to a process for preparing tri-substituted (2,5 dihydroxyphenyl)phosphonium salts of thl formula
characterized by reacting together (a) a phosphine of the formula R1R2R3P wherein R1, R2 and R3 are each independently hydrocarbyl or inertly-substituted hydrocarbyl groups of from 1 to 20 carbon atoms; (b) para-benzoquinone;,and (c) a protic acid of the formula HOAX, wherein AO is an inert anion, in a liquid reaction medium which is a lower alkanol of from 1 to 4 carbon atoms, 1,2-ethylene glycol, 1,2-propylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, a lower alkyl (C1-C4) ether of said glycols, or a mixture thereof. The desired product is obtained as a solution and can be used as such in catalyzing the reaction of epoxides with phenols and/or carboxylic acids (or anhydrides). This is a substantial advantage because the isolation and purification steps normally necessitated in the Ramirez et al. process are thereby eliminated.
Alternatively, of course, the desired product can be isolated and recovered from the reaction mixture by conventional techniques such as, for example, solvent extraction or stripping off the solvent under reduced pressure.
Suitable lower alkanols are, for example, methanol, ethanol, n-propanol, isopropanol and n-butanol. Suitable lower alkyl ethers of said glycols are, for example, diethylene glycol methyl ether and diethylene glycol n-butyl ether. ire reaction is preferably carried out in methanol.
The reactants in the instant process are well known classes of compounds, essentially any member of which can be used in the instant process. The preferred phosphine reactants are tri-n-butyl-phosphine and triphenylphosphine. Tri-nbutylphosphine is the most preferred.
The anion AO in the product may be predetermined by choosing the appropriate inorganic or organic protic acid which supplies the requisite anion AO.
Alternatively, the anion of any particular compound of formula I can be exchanged for another anion by conventional anion exchange techniques. The nonnucelophilic anions such as, for example, bisulfate, acetate, chloroacetate, diacetate and adipate, are preferred when the phosphonium salts are used in preparing pre-catalyzed epoxy resins. Bromide and iodide anions are the preferred nucelophilic anions.
The reaction temperature may be varied to convenience but best results are achieved when the reaction temperature is maintained at a temperature of between the freezing point of the reaction mixture and 600C. Preferably, the reaction temperature is maintained between the freezing point of the reaction mixture and 0 C, more preferably from -400C to OOC. The reaction rate is very high even at these rather low temperatures and the product yield is increased at the expense of reaction by-products.
The ratio of the reactants may be varied although best results are achieved when essentially stoichiometric quantities of the reactants are used. A slight excess of the phosphine reactant is advantageous to maximize conversion of the reactants to the desired product.
The order of addition is not absolutely critical but best results are achieved when the phosphine reactant is added to an intimately blended reaction mixture of the para-benzoquinone and acid reactants in the liquid reaction medium.
The phosphonium salts prepared in accordance with the present invention may be blended with liquid epoxy resins, and such epoxy resin/phosphonium salt blends may be used to prepare substantially linear high molecular weight epoxy resins.
The following examples will further illustrate the invention.
Examples 1--6 Preparation of Tri-n-butyl (2,5 - dihydroxyphenyl)phosphonium Salts
Neat tri-n-butylphosphine (106.4 g., 0.525 mole) at OOC was added in increments to a vigorously stirred, precooled (approximately -400C to --200C) suspension of p-benzoquinone (54.1 g, 0.50 mole) in a methanol solution containing 0.50 mole of the acid indicated in Table I below. The temperature of the reaction mixture was maintained at approximately -lO0C during the addition of the phosphine reactant. After the addition of the phosphine was complete, the reaction mixture was observed for turbidity and, if turbid, the temperature was allowed to rise until a clear solution was obtained. Then, the temperature of the resulting solution was lowered to about -10"C for an additional half hour of vigorous sitrring. The amount of methanol in each instance was selected such that the weight of the methanol was equal to the combined weight of the reactants.
TABLE I
Maximum Tempetature Product
Ex HOAo Allowed/Time Yield () HBF4(50% in H2O) 35"C/5 minutes 97
2 H3PO4 (85 /n in H2O) 25"C/5 minutes 84
3 HCl (37% in H2O) 30"C/5 minutes 96
4 CH2=CHCOOH 12qC/5 minutes 81
5 ClCH2COOH -10 C/35 minutes 96
6 CH3COOH -10"C/20 minutes 89
The product yield in the above samples was determined by comparing the U.V.
absorption of the methanol solution of the reaction product at 317,,versus the U.V.
absorption of a 50 weight percent of authentic sample in methanol ({317"m=4971.0).
The desired products were obtained as a crystalline solid by evaporating the methanol solvent from the reaction products and triturating the residues with acetone. Elemental analyses on the crystalline solids so obtained were very close to the theoretical calculations.
Methanol solutions of reaction product from Examples 1--6 were easily blended with liquid epoxy resins such as, for example, the diglycidyl ether of bisphenol-A. Substantially linear high molecular weight epoxy resins were obtained having epoxy values very close to theoretical when the epoxy resin/phosphonium salt mixtures were reacted with bisphenol-A at 1600C for 4--6 hours. Other phosphonium salts, as described above, can be similarly prepared and used.
WHAT WE CLAIM IS:
1. A process for preparing tri-substituted (2,5 dihydroxyphenyl)phosphonium salts of the formula
which comprises reacting together (a) a phosphine of the formula RtR2R3P wherein R1, R2 and R3 are each independently hydrocarbyl or inertly-substituted hydrocarbyl groups of from 1 to 20 carbon atoms; (b) para-benzoquinone; and (c) a protic acid of the formula HOAO wherein AO is an inert anion, in a liquid reaction medium which is a lower alkanol of from 1 to 4 carbon atoms, 1,2-ethylene glycol,
1,2-propylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, a lower alkyl (C1-C4) ether of said glycols, or a mixture thereof.
2. A process as claimed in claim 1 in which the reaction is conducted at a temperature of from the freezing point of the reaction mixture up to 600 C.
3. A process as claimed in claim 1 in which the reaction is conducted at a temperature of from -40"C to OOC.
4. A process as claimed in any one of the preceding claims in which the reaction is carried out in methanol.
5. A process as claimed in any one of the preceding claims in which R1, R2 and
R3 are each n-butyl.
6. A process as claimed in any one of the preceding claims in which An is a bisulfate, acetate, chloroacetate, diacetate, adipate, bromide or iodide anion.
7. A process as claimed in any one of the preceding claims in which essentially stoichiometric quantities of the reactants are used.
8. A process as claimed in any one of claims 1 to 6 in which the phosphine is used in excess of the stoichiometric quantity.
9. A process as claimed in any one of the preceding claims in which the phosphine is added to an intimately blended reaction mixture of the parabenzoquinone and acid reactants in the liquid reaction medium.
10. A process as claimed in claim 1 substantially as hereinbefore described in any one of the Examples.
Il. A tri-substituted (2,5 - dihydroxyphenyl)phosphonium salt which has been prepared by a process as claimed in any one of the preceding claims.
12. A blend of a solution of a tri-substituted (2,5 dihydroxyphenyl)phosphonium salt as claimed in claim 11 and a liquid epoxy resin.
13. A process for preparing a substantially linear high molecular weight epoxy resin involving the use of a tri-substituted (2,5 - dihydroxyphenyl)phosphonium salt as claimed in claim 11 or a blend as claimed in claim 12.
14. A substantially linear high molecular weight epoxy resin which has been prepared by a process as claimed in claim 13.
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (14)
1. A process for preparing tri-substituted (2,5 dihydroxyphenyl)phosphonium salts of the formula
which comprises reacting together (a) a phosphine of the formula RtR2R3P wherein R1, R2 and R3 are each independently hydrocarbyl or inertly-substituted hydrocarbyl groups of from 1 to 20 carbon atoms; (b) para-benzoquinone; and (c) a protic acid of the formula HOAO wherein AO is an inert anion, in a liquid reaction medium which is a lower alkanol of from 1 to 4 carbon atoms, 1,2-ethylene glycol,
1,2-propylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, a lower alkyl (C1-C4) ether of said glycols, or a mixture thereof.
2. A process as claimed in claim 1 in which the reaction is conducted at a temperature of from the freezing point of the reaction mixture up to 600 C.
3. A process as claimed in claim 1 in which the reaction is conducted at a temperature of from -40"C to OOC.
4. A process as claimed in any one of the preceding claims in which the reaction is carried out in methanol.
5. A process as claimed in any one of the preceding claims in which R1, R2 and
R3 are each n-butyl.
6. A process as claimed in any one of the preceding claims in which An is a bisulfate, acetate, chloroacetate, diacetate, adipate, bromide or iodide anion.
7. A process as claimed in any one of the preceding claims in which essentially stoichiometric quantities of the reactants are used.
8. A process as claimed in any one of claims 1 to 6 in which the phosphine is used in excess of the stoichiometric quantity.
9. A process as claimed in any one of the preceding claims in which the phosphine is added to an intimately blended reaction mixture of the parabenzoquinone and acid reactants in the liquid reaction medium.
10. A process as claimed in claim 1 substantially as hereinbefore described in any one of the Examples.
Il. A tri-substituted (2,5 - dihydroxyphenyl)phosphonium salt which has been prepared by a process as claimed in any one of the preceding claims.
12. A blend of a solution of a tri-substituted (2,5 dihydroxyphenyl)phosphonium salt as claimed in claim 11 and a liquid epoxy resin.
13. A process for preparing a substantially linear high molecular weight epoxy resin involving the use of a tri-substituted (2,5 - dihydroxyphenyl)phosphonium salt as claimed in claim 11 or a blend as claimed in claim 12.
14. A substantially linear high molecular weight epoxy resin which has been prepared by a process as claimed in claim 13.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2057478A GB1580603A (en) | 1978-05-18 | 1978-05-18 | Process for preparing triorgano-(2,5-dihydroxyphenyl) phosphonium salts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2057478A GB1580603A (en) | 1978-05-18 | 1978-05-18 | Process for preparing triorgano-(2,5-dihydroxyphenyl) phosphonium salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1580603A true GB1580603A (en) | 1980-12-03 |
Family
ID=10148161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2057478A Expired GB1580603A (en) | 1978-05-18 | 1978-05-18 | Process for preparing triorgano-(2,5-dihydroxyphenyl) phosphonium salts |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1580603A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2135674A (en) * | 1983-02-28 | 1984-09-05 | Dow Chemical Co | A process for preparing advanced epoxy resins employing tetrahydrocarbyl phosphonium salts as catalysts and advanced epoxy resins prepared by the process |
| EP0132789A1 (en) * | 1983-07-21 | 1985-02-13 | The Dow Chemical Company | A process for reacting an epoxy resin or a thioepoxide with a polyhydric phenol, a polyhydric thiophenol, a carboxylic acid or a carboxylic acid anhydride |
-
1978
- 1978-05-18 GB GB2057478A patent/GB1580603A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2135674A (en) * | 1983-02-28 | 1984-09-05 | Dow Chemical Co | A process for preparing advanced epoxy resins employing tetrahydrocarbyl phosphonium salts as catalysts and advanced epoxy resins prepared by the process |
| EP0132789A1 (en) * | 1983-07-21 | 1985-02-13 | The Dow Chemical Company | A process for reacting an epoxy resin or a thioepoxide with a polyhydric phenol, a polyhydric thiophenol, a carboxylic acid or a carboxylic acid anhydride |
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| Date | Code | Title | Description |
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| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19960518 |