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US 8,895,773 B2Granted
Manufacture and use of alkyl p-toluates
AssigneeInvista North America S.A.R.L.
InventorCarina Araullo McAdams
Life of this patent
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Abstract
The present invention relates to the manufacture of alkyl p-toluates from an alkyl p-toluic acid ester and a mono-functional, branched, linear or cyclic medium chain length alkyl alcohol, and their use as a plasticizer in polymers. Additionally, the present invention relates to articles and materials comprising such alkyl p-toluates.
Claims10
A method for the manufacture of an alkyl p-toluate of formula I,
- wherein R is a C4-C20 branched, linear or cyclic alkyl radical, comprising:
- oxidizing p-xylene to produce dimethyl terephthalate and a byproduct stream, wherein the byproduct stream comprises an ester comprising at least 80% by weight of C1-C4 alkyl p-toluic acid ester;
- and
- transesterifying the ester and one or more C4-C20 mono-functional branched, linear or cyclic aliphatic alcohols at a reaction temperature of 160° C. to 260° C.,
- wherein the transesterifying is in the presence of a catalyst.
2 more elements
A method for the manufacture of an alkyl p-toluate of formula I,
- wherein R is a C4-C20 branched, linear or cyclic alkyl radical, comprising:
- a. oxidizing p-xylene to produce dimethyl terephthalate and a byproduct stream, wherein the byproduct stream comprises:
- an ester comprising a methyl p-toluate;
- b. transesterifying the methyl p-toluate with one or more C4-C20 mono-functional branched, linear or cyclic aliphatic alcohol in the presence of a catalyst at a reaction temperature of 160° C. to 260° C. to form a resultant product,
- c. distilling the resultant product under vacuum to remove the unreacted methyl p-toluate and alcohol,
- d. optionally raising the temperature,
- e. optionally reducing the pressure, and
- f. distilling off the alkyl p-toluate.
5 more elements
A method for the manufacture of an alkyl p-toluate of formula I,
- wherein R is a C4-C20 branched, linear or cyclic alkyl radical, comprising:
- a. oxidizing p-xylene to produce dimethyl terephthalate and a byproduct stream, wherein the byproduct stream comprises:
- an ester comprising a methyl p-toluate;
- b. transesterifying the methyl p-toluate with one or more C4-C20 mono-functional branched, linear or cyclic aliphatic alcohol in the presence of a catalyst at a reaction temperature of 160° C. to 260° C. to form a resultant product,
- c. distilling the resultant product under vacuum to remove the unreacted methyl p-toluate and alcohol to form a purified alkyl p-toluate,
- d. filtering the purified alkyl p-toluate, and
- e. optionally distilling the purified alkyl p-toluate under vacuum to distill off the alkyl p-toluate.
4 more elements
Dependencies are inferred from the claim text.