← Back to Patent Explorer
US4112240A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for the manufacture of light colored dipropyleneglycol dibenzoate

Assignee: Dynamit Nobel AG
•
Filing: 1976-08-09
•
Granted: 1978-09-05
•
Expires: 1996-08-09
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract Process for production of dipropyleneglycol dibenzoate isomer mixture of the formulas: ##STR1## A crude methyl benzoate containing at least 80 wt.% methylbenzoate, which is a by-product of production of dimethylterephthalate by catalytic oxidation of p-xylene and/or methyl-p-toluate and esterification of the resulting acids with methanol, is contacted with dipropylene glycol commercial isomer mixture in the presence of a catalyst for a transesterification to produce said benzoate. The catalyst is an aluminum alkoxide or an aluminum silicon alkoxide containing the group Al O Si. The product is obtained in good yield, has good color, and is useful as a plasticizer for PVC.

Inventors

  • 👤 Hans Leo Hulsmann
  • 👤 Gustav Renckhoff

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 14:35
CPC Classifications
C; C07; C07C; C07C69/00; C07C69/76; C07C69/78; C07C67/00; C07C67/08

Claims Analysis

Total Claims: 7
Claim 1
Independent Claim 133 words
Process for the manufacture of dipropyleneglycol dibenzoate isomer mixture, which comprises contacting technical methyl benzoate containing more than 80 wt.% methyl benzoate which is the product of production of dimethyl terephthalate by catalytic oxidation of p-xylene and/or methyl-p-toluate and esterification of the resulting acids with methanol, to produce a crude reaction product rich in dimethylterephthalate, treatment of the crude product to recover dimethylterephthalate and produce said technical methyl benzoate as a by-product, with dipropylene glycol commercial isomer mixture of 1,1'-oxy-di-2-propanol, 2-(hydroxypropoxy)-1-propanol, and 2,2"-oxy-di-1-propanol, in the presence of at least one of aluminum and aluminum silicon alkoxides of the formula Al(OR).sub.3 or (RO).sub.3 SiOAl(OR).sub.2 wherein the R's are alike or different and are lower alkyl, as catalyst, at temperature above 150° C, for a time sufficient for transesterification to produce said dipropyleneglycol dipropyleneglycol dibenzoate.
Claim 2
Dependent Claim 133 words
Process for the manufacture of dipropyleneglycol dibenzoate isomer mixture, which comprises contacting technical methyl benzoate containing more than 80 wt.% methyl benzoate which is the product of production of dimethyl terephthalate by catalytic oxidation of p-xylene and/or methyl-p-toluate and esterification of the resulting acids with methanol, to produce a crude reaction product rich in dimethylterephthalate, treatment of the crude product to recover dimethylterephthalate and produce said technical methyl benzoate as a by-product, with dipropylene glycol commercial isomer mixture of 1,1'-oxy-di-2-propanol, 2-(hydroxypropoxy)-1-propanol, and 2,2"-oxy-di-1-propanol, in the presence of at least one of aluminum and aluminum silicon alkoxides of the formula Al(OR).sub.3 or (RO).sub.3 SiOAl(OR).sub.2 wherein the R's are alike or different and are lower alkyl, as catalyst, at temperature above 150° C, for a time sufficient for transesterification to produce said dipropyleneglycol dipropyleneglycol dibenzoate.
Claim 3
Dependent Claim 61 words
Process according to claim 1, wherein the transesterification product includes compounds boiling at a lower boiling point than the dipropyleneglycol dibenzoate, said compounds are removed from the transesterification product by distillation, and the dipropyleneglycol dibenzoate resulting from said distillation is connected with ozone at a temperature of less than 150° C and for a time sufficient to improve the color thereof.
Claim 4
Dependent Claim 27 words
Process according to claim 1, wherein the amount of catalyst is up to 0.8% of the sum of the input weight of methyl benzoate and dipropylene glycol.
Claim 5
Dependent Claim 26 words
Process according to claim 1, wherein said catalyst is at least one of Al(OC.sub.2 H.sub.5).sub.3 al(OC.sub.3 H.sub.7).sub.3 al(OC.sub.3 H.sub.7 -i).sub.3 (C.sub.2 H.sub.5 O).sub.3 Si--O--Al(OC.sub.4 H.sub.9 -sec.).sub.2.
Claim 6
Dependent Claim 12 words
Process according to claim 1, wherein the catalyst is Al(OR) 3 .
Claim 7
Dependent Claim 14 words
Process according to claim 1, wherein the catalyst is (RO) 3 SiOAl(OR) 2 .

References Cited (Backward Citations)

US2822348A Cited
US3031491A Cited
US3098093A Cited
US3194791A Cited
US3356712A Cited
US3696141A Cited
US3784578A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-09-04 1982-03-06 1982-09-05 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-09-04 1986-03-06 1986-09-05 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-09-04 1990-03-06 1990-09-05 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag