US3333030A - Process for oxidation of secondary esters of phosphorous acid to primary and secondary esters of phosphoric acid - Google Patents

Process for oxidation of secondary esters of phosphorous acid to primary and secondary esters of phosphoric acid Download PDF

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Publication number
US3333030A
US3333030A US302705A US30270563A US3333030A US 3333030 A US3333030 A US 3333030A US 302705 A US302705 A US 302705A US 30270563 A US30270563 A US 30270563A US 3333030 A US3333030 A US 3333030A
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phosphite
halo
carbon atoms
catalyst
substituted
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US302705A
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Charles F Baranauckas
James J Hodan
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GE Chemicals Inc
Hooker Chemical Corp
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Hooker Chemical Corp
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Priority to BE674673D priority Critical patent/BE674673A/xx
Priority to NL124637D priority patent/NL124637C/xx
Application filed by Hooker Chemical Corp filed Critical Hooker Chemical Corp
Priority to US302705A priority patent/US3333030A/en
Priority to US302730A priority patent/US3334158A/en
Priority to DEH53481A priority patent/DE1293769B/de
Priority to GB33304/64A priority patent/GB1076795A/en
Priority to GB6761/67A priority patent/GB1076796A/en
Priority to FR985349A priority patent/FR1411259A/fr
Priority to NL6409467A priority patent/NL6409467A/xx
Application granted granted Critical
Publication of US3333030A publication Critical patent/US3333030A/en
Priority to NL6717273A priority patent/NL6717273A/xx
Assigned to BORG-WARNER CHEMICALS, INC., A CORP. OF DE reassignment BORG-WARNER CHEMICALS, INC., A CORP. OF DE ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: BORG-WARNER CORPORATION
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    • 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
    • C07F9/09—Esters of phosphoric 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
    • 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
    • C07F9/09—Esters of phosphoric acids
    • C07F9/113—Esters of phosphoric acids with unsaturated acyclic alcohols

Definitions

  • This invention relates to the preparation of esters of phosphoric acid. More particularly, it relates to the oxidation of secondary esters of phosphorous acid in the presence of a catalyst to form the corresponding primary and secondary esters of phosphoric acid.
  • Secondary esters of phosphorous acid have the general formula wherein R maybe aliphatic or aromatic. It is known in the art thatsecondary esters of phosphorous acid (secondary phosphites) are not amenable to oxidation. Kosolapolf, on page 194 of the text, Organo Phosphorus Compounds, published by Wiley and Sons (1958), states .that the secondary esters of phosphorous acid exist substantially in'the ketone form. To support the pentavalent .ketone formula of these esters, illustrated in Formula 1,
  • diesters of phosphorous acid may be oxidized, in the presence of a catalyst, to the mono and diesters of phosphoric acid.
  • Monoesters and diesters of phosphoric acid have the formulae:
  • monoand diesters of phosphoric acid and mixtures thereof may be prepared by passing a gas containing "oxygen through a reaction mixture of a diester of phosphorous acid having the formula where R is selected from the group consisting of alkyl, alkenyl, phenyl, alkylphenyl, halo-substituted aryl, haloalkenyl, aralkyl and mixtures thereof, and a catalyst.
  • the process of this invention may be carried out in the presence of a metal or a metal oxide.
  • a metal or a metal oxide examples of the elements which may be utilized in the practice of this invention are copper, copper oxides and metals selected from the transition elements such as scandium, titanium,
  • Suitable dialkyl, halo-substituted dialkyl and dialicyclic phosphites which may be utilized in the present invention may contain from 1 to about 20 carbon atoms in each alkyl, with the more preferred phosphites containing from 1 to about 12 carbon atoms and the most preferred phosphites containing from 1 to about 6 carbon atoms in each alkyl.
  • the alicyclic radical has from 4 to 8 carbon atoms.
  • phosphites are dimethyl phosphite, diethyl phosphite, dipropyl phosphite, diisopropyl phosphite, dibutyl phosphite, di-tertiary butyl phosphite, dihexyl phosphite, diisohexyl phosphite, diheptyl phosphite, dinonyl phosphite, dicyclohexyl phosphite, didecyl phosphites, didodecyl phosphite, distearyl phosphite, di-2-ch1oroethyl phosphite, di-3-bromopropyl phosphite, di-4-chlorodecyl phosphite, dicyclohexane phosphite, di(3-ethylcyclopentan
  • Suitable dialkenyl and halosubstituted dialkenyl phosphites which may be utilized in the practice of this invention may contain from 2 to about 10 carbon atoms in each alkylene, with from 2 to about 8 carbon atoms being more preferred and the most preferred phosphites containing from 1 to about 6 carbon atoms.
  • phosphites are di-(Z-bromo-Z-butene) phosphite, di- (3-chloro-4-heptene) phosphite, di-4-heptene phosphite, diallyl phosphite, dimethallyl phosphite, allyl methallyl phosphite, 2-chloro-2-butene heptene phosphite and di(3 heptene) phosphite, and so forth.
  • Diaryl, halosubstituted diaryl and diaralkyl phosphites which may be utilized in the practice of this invention are diphenyl phosphite, dibenzyl phosphite, dicresyl phosphite, di(2-decylphenyl) phosphite, di(2-dodecylphenyl) phosphite, di-(2-chlor0phenyl) phosphite, di-(Z-bromophenyl) phosphite, di-(2,6-dichlorophenyl) phosphite, di- (2,4-dibromophenyl) phosphite, di-(Z-iodophenyl) phosphite, phenyl cresyl phosphite, Z-chlorophenyl cresyl phosphite, and so forth.
  • the aryl, halo-substituted aryl, and aralkyl may contain from 6 to about 18 carbon atoms, it being preferred to utilize aryl groups having from 6 to about 10 carbon atoms, with the most preferred embodiment of this invention having the aryl, halo-substituted aryl, and aralkyl containing from 6 to 8 carbon atoms.
  • the phosphite and a suflicient amount of a catalyst are added to a reaction vessel.
  • Oxygen or oxygen contained in a carrier gas e.g., nitrogen, air, and so forth, is passed through the reaction mixture.
  • a stoichiometric or excess amount of oxygen may be utilized.
  • the excess of oxygen or air utilized may be more than 200 times the stoichiometric amount required to perform the reaction of the invention.
  • one utilizes an excess of oxygen between about 1 and 200 times the stoichiometric amount required, with about 1 to 30 times being preferred and 1 to 15 times being most preferred.
  • oxygen is in a carrier gas it is preferred to utilize a mixture in the range of about 10-40 percent oxygen and about -60 percent carrier gas.
  • the amount of catalyst employed in the process of this invention may be between about 0.0001 and 1 mole per mole of secondary phosphite utilized, with between about 0.001 mole and 0.5 mole per mole of phosphite being preferred with between about 0.001 and 0.1 mole of catalyst per mole of phosphite utilized being the most preferred.
  • a gram weight of from about 0.005 gram and 5 grams of catalyst per molar weight of phosphite may be employed.
  • reaction may be carried out at a temperature from about 65 to 300 degrees centigrade, it being more 10 prepared following the above description by passing oxying the invention except as defined in the appended claims. All temperatures are in degrees centigrade and all parts are by weight, unless otherwise set forth.
  • Examples 16 In these examples a copper oxide catalyst was em ployed. The secondary phosphite, as set forth in Table I, and catalyst were placed in the reaction vessel in the amounts indicated. Oxygen was then passed into the reaction vessel below the level of the mixture for a period of time as indicated in the table.
  • hydroxyl-containing compound is employed in place of the secondary ester of phosphorous acid.
  • hydroxyl containing compounds which may be utilized are methanol, ethanol, propanol, 2-propanol, butanol, heptanol, decanol, dodecanol, stearyl alcohol, 2-chloropropanol, 3-bromobutanol, propanol, tert-butanol, phenol, cresyl alcohol, dicresyl alcohol, cyclohexanol, 1,3-dimethylA-cyclohexanol, benzyl alcohol, neopentyl alcohol, Z-phenyl-ethanol, and so forth.
  • the alkyl and halo-substituted alkyl contain from 1 to about 20 carbon atoms, with the preferred alkyl and halo-substituted alkyl having 1 to about 12, and the most preferred alkyl and halo-substituted alkyls having from 1 to about 6 carbon atoms.
  • the preferred alkenyl and halo-substituted alkenyl may contain from 2 to about 10 carbon atoms, with the more preferred alkylene and halo-substituted alkylene containing from 2 to about 8 carbon atoms and the most preferred alkenyl and halo-substituted alkenyl containing from 2w 6 carbon atoms.
  • the substituted phenyl, halo-substituted phenyl, and aralkyl contain from 6 to about 18 carbon atoms, with the more preferred substituted phenyl, halo-substituted phenyl, and aralkyl containing from 6 to about 10 carbon atoms, the most preferred substituted phenyl, halo-substituted phenyls and aralkyl containing from 6 to about 8 carbon atoms, and the preferred alicyclic containing 4 to 6 carbon atoms.
  • the hydroxyl containing compound may have a primary, secondary or tertiary hydroxyl.
  • the ratio of alcohol of phosphorus may be from 1:1 to about 10:1 with the preferred ratio being from 1:1 to about 8:1 and the most preferred ratio being from 1:1 to 5:1. It is theorized that the primary and secondary esters of phosphoric acid are formed in this reaction by the oxidation of a secondary ester of phosphorous acid which may be formed as an intermediate for a brief period of time.
  • the mixture of the dialkyl phosphate and the monoalkyl phosphate may be separated by known techniques if desired, such as by forming their salts which have different solubilities and then fractionally crystallizing or dissolving, or by chromatographic separation. Analysis of the unseparated residue was carried out with a Sargent Auto Titrater. The products peaked in different areas against a caustic standard to establish the percentage of primary and secondary phosphate present in the product.
  • Example 6 above (no catalyst) was utilized as a control and establishes that no dialkyl acid phosphate was formed, elements in the first transition series being more preferred.
  • di-ter-tiary butyl phosphite diisohexyl phosphite, distearyl phosphite, dicyclohexyl phosphite, di-3-bromopropy1 phosphite, di-4- chlorodecyl phosphite, ethyl butyl phosphite, hexyl decyl phosphite, di'(2-bromo-2-butene) phosphite, di-4-heptene phosphite, di(2-chlorophenyl)phosphite, dibenzyl phosphite, dicyclohexyl phosphite and dicresyl phosphite, used in the processes of Example 2 results in the corre sponding primary and secondary esters of phosphoric acid.
  • Example 7 Diethyl phosphite (138 parts) and vanadium pentoxide (0.5 part) were placed in a reaction vessel and heated to about degrees centigrade. Oxygen was passed below the level of the reaction mixture for about 10 hours at 187 milliliters per hour. The initial exothermic reaction was cooled and the temperature was maintained about between degrees and degrees centigrade. Analysis indicated that 56.2 percent of the product was diethyl acid phosphate,
  • Example 8 Example 7 as p a ed util zing d ethyl phosphit (138 parts) and cobalt trioxide (0.5 part). The product analyzed 5.9 percent diethyl phosphate,
  • Example 9 5 catalyst is selected from the group consisting of copper
  • Example 7 was repeated utilizing titanium dioxide as a 'icandmm i m i q manganese catalyst. The reaction was run for about 12 hours. Analy- Iron cobalt i ytmum .zlrcomumi mobmm sis showed that 9 percent of the residue recovered was i i technetium pi i rhodlllm panafhum diethyl phosphate 1' emum, tungsten, osmium, llldlum, platinum, thelr ox- 10 ides, and mixtures thereof.
  • a process in accordance with claim 1 wherein the intestinalte catalyst in the proportions'set forth in Table II catalyst is titanium dioxide were heated with stirring to the desired temperature.
  • R is selected from the group consisting of alkyl
  • catalyst is CIIPI'OUS oXidth alkenyl, phenyl, alkylphenyl, halo-substituted phenyl and ⁇ A Process P P P 'Y and Secondary alkylphenyl, halo-substituted alkyl, halo-substituted alesters of phosphonc and comprising passing oxygen k l, li li of 4 to 3 carbon atoms, d h l lk l through a reaction mixture mainta-inw at a temperature comprising passing oxygen through a reaction mixture of of at least about 65 degrees Centigrade O a Secondary a diester of phosphorous acid of the formula:
  • R is selected from the group consisting of alkyl having from 1 to about 6 carbon atoms,
  • a process of preparing primary and secondary esters of phosphoric acid comprising passing oxygen through a reaction mixture, maintained at a temperature of at least about 65 degrees centigrade, of phosphorus and a hydroxyl containing compound having the formula:
  • R is selected from the group consisting of phenyl, :alkylphenyl phenylalkyl, alkyl, alkenyl, halo-substituted alkyl, halo-substituted alkenyl, and alicyclic having from 4 to about 6 carbon atoms, and from 0.001 to about 0.1 mole per mole of phosphorus of a catalyst selected from the group consisting of copper and cuprous oxide, the alcohol and phosphorus present in a ratio of from 1:1 to :1.
  • a process of preparing a primary ester of phosphoric acid comprising passing oxygen through a reaction mixture maintained at a temperature of at least about 65 degrees centigrade of a secondary ester of phosphorous acid of the formula wherein R is selected from the group consisting of alkyl having from 1 to about 6 carbon atoms, halo-substituted alkyl having from 1 to about 6 carbon atoms, alkenyl having from 2 to about 6 carbon atoms, halo-substituted alkenyl having from 2 to about 6 carbon atoms, phenyl alkylphenyl, halo-substituted phenyl and alkylphenyl and alicyclic having from 4 to about 8 carbon atoms and from 0.001 to about 0.1 mole per mole of phosphite of a catalyst selected from the group consisting of cuprous oxide, copper, vanadium pentoxide, cobalt trioxide and titanium dioxide and the oxygen being passed through the reaction mixture in an excess equal to
  • a process of preparing a primary ester of phosphoric acid comprising passing oxygen through a reacti-on mixture, maintained at a temperature of at least about degrees Centigrade, of phosphorus and a hydroxyl containing compound having the formula:
  • R is selected from the group consisting of phenyl, alkylphenyl phenylalkyl, alkyl, alkenyl, halo-substituted alkyl, halo-substituted alkenyl, having from 2 to 6 carbon atoms, and alicyclic having from 4 to about 6 carbon atoms, and from 0.001 to about 0.1 mole per mole of phosphorus of a catalyst selected from the group con sisting of copper and cuprous oxide, the alcohol and phosphorus present in a ratio of from 1:1 to 5:1.

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US302705A 1963-08-16 1963-08-16 Process for oxidation of secondary esters of phosphorous acid to primary and secondary esters of phosphoric acid Expired - Lifetime US3333030A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
BE674673D BE674673A (enrdf_load_stackoverflow) 1963-08-16
NL124637D NL124637C (enrdf_load_stackoverflow) 1963-08-16
US302705A US3333030A (en) 1963-08-16 1963-08-16 Process for oxidation of secondary esters of phosphorous acid to primary and secondary esters of phosphoric acid
US302730A US3334158A (en) 1963-08-16 1963-08-16 Process for the preparation of alkenyl phosphates from alkenyl phosphites
DEH53481A DE1293769B (de) 1963-08-16 1964-08-07 Verfahren zur Herstellung von Gemischen primaerer und sekundaerer Orthophosphorsaeureester
GB6761/67A GB1076796A (en) 1963-08-16 1964-08-14 Preparation of phosphates
GB33304/64A GB1076795A (en) 1963-08-16 1964-08-14 Method of preparing organic phosphates
FR985349A FR1411259A (fr) 1963-08-16 1964-08-17 Procédé pour la préparation de phosphates organiques
NL6409467A NL6409467A (enrdf_load_stackoverflow) 1963-08-16 1964-08-17
NL6717273A NL6717273A (enrdf_load_stackoverflow) 1963-08-16 1967-12-19

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US302705A US3333030A (en) 1963-08-16 1963-08-16 Process for oxidation of secondary esters of phosphorous acid to primary and secondary esters of phosphoric acid
US302730A US3334158A (en) 1963-08-16 1963-08-16 Process for the preparation of alkenyl phosphates from alkenyl phosphites

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US302730A Expired - Lifetime US3334158A (en) 1963-08-16 1963-08-16 Process for the preparation of alkenyl phosphates from alkenyl phosphites

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BE (1) BE674673A (enrdf_load_stackoverflow)
DE (1) DE1293769B (enrdf_load_stackoverflow)
GB (2) GB1076796A (enrdf_load_stackoverflow)
NL (3) NL6409467A (enrdf_load_stackoverflow)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3445547A (en) * 1964-12-01 1969-05-20 Hooker Chemical Corp Preparation of esters of phosphoric acid
US3939229A (en) * 1974-12-04 1976-02-17 Borg-Warner Corporation Preparation of aliphatic phosphates
US4331591A (en) * 1978-10-05 1982-05-25 Ciba-Geigy Corporation Chemical process for the production of α-aminophosphonic acids and peptide derivatives

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57134493A (en) * 1981-02-12 1982-08-19 Sankin Kogyo Kk Phosphoric ester derivative

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2921087A (en) * 1957-12-19 1960-01-12 Eastman Kodak Co Process for producing dialkyl phosphoric acids
US2952699A (en) * 1955-12-23 1960-09-13 Lubrizol Corp Preparation of substituted phosphoric acids
US3136805A (en) * 1960-08-04 1964-06-09 Hooker Chemical Corp Process for making trialkyl phosphates
US3167577A (en) * 1962-05-21 1965-01-26 Exxon Research Engineering Co Method of preparing and employing phosphorus oxide smokes to make phosphate esters

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3042697A (en) * 1958-10-28 1962-07-03 Gulf Research Development Co Process for making phosphorus acid esters
US3136804A (en) * 1960-08-04 1964-06-09 Hooker Chemical Corp Oxidation process for converting unsaturated tertiary phosphite esters to phosphates
DE1135459B (de) * 1961-01-03 1962-08-30 Leuna Werke Iawalter Ulbrichti Verfahren zur Herstellung von neutralen aliphatischen Orthophosphorsaeureestern

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2952699A (en) * 1955-12-23 1960-09-13 Lubrizol Corp Preparation of substituted phosphoric acids
US2921087A (en) * 1957-12-19 1960-01-12 Eastman Kodak Co Process for producing dialkyl phosphoric acids
US3136805A (en) * 1960-08-04 1964-06-09 Hooker Chemical Corp Process for making trialkyl phosphates
US3167577A (en) * 1962-05-21 1965-01-26 Exxon Research Engineering Co Method of preparing and employing phosphorus oxide smokes to make phosphate esters

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3445547A (en) * 1964-12-01 1969-05-20 Hooker Chemical Corp Preparation of esters of phosphoric acid
US3939229A (en) * 1974-12-04 1976-02-17 Borg-Warner Corporation Preparation of aliphatic phosphates
US4331591A (en) * 1978-10-05 1982-05-25 Ciba-Geigy Corporation Chemical process for the production of α-aminophosphonic acids and peptide derivatives

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DE1293769B (de) 1969-04-30
US3334158A (en) 1967-08-01
NL6717273A (enrdf_load_stackoverflow) 1968-03-25
BE674673A (enrdf_load_stackoverflow)
NL6409467A (enrdf_load_stackoverflow) 1965-02-17
GB1076795A (en) 1967-07-19
GB1076796A (en) 1967-07-19
NL124637C (enrdf_load_stackoverflow)

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