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
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 |