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US4096192A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for the preparation of 2-methyl-1,3-propanediol

Assignee: EIDP Inc
•
Filing: 1976-03-30
•
Granted: 1978-06-20
•
Expires: 1996-03-30
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Abstract

Abstract A process for the preparation of 2-methyl-1,3-propanediol (MPD) by recycling mixed diols from the process for the preparation of 1,4-butanediol from acrolein and aliphatic diols until the final product is essentially 1,4-butanediol and MPD.

Inventors

  • 👤 Kamlesh Kumar Bhatia
  • 👤 Charles Carmen Cumbo

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 20:02
CPC Classifications
C; C07; C07D; C07D319/00; C07D319/04; C07D319/06; C07C; C07C29/00; C07C29/09; C07C29/10; C07C29/132; C07C29/136; C07C29/14; C07C29/141

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 173 words
A continuous process for the preparation of 2-methyl-1,3-propanediol which comprises (a) reacting acrolein with a 1,3-aliphatic diol with 3 to 7 carbon atoms other than 2-methyl-1,3-propanediol under conventional conditions to prepare a cyclic acetal; (b) hydroformylating the cyclic acetal in the presence of a rhodium complex catalyst comprising rhodium carbonyl and a phosphite ligand of the formula ##STR5## wherein R 1 , R 2 and R 3 are the same or different phenyl, substituted phenyl or alkyl groups having 1 to 12 carbon atoms under conventional conditions to prepare the aldehyde of the cyclic acetal; (c) hydrogenating and hydrolyzing the aldehyde of the cyclic acetal in the presence of a hydrogenation catalyst and an ion exchange catalyst to prepare 1,4-butanediol and a mixture of diols; (d) separating the mixture of diols from 1,4-butanediol; (e) recycling said mixture back to step (a) to react with acrolein in place of the diol of (a) for a number of cycles until a product consisting of 1,4-butanediol and essentially 2-methyl-1,3-propanediol; and (f) separating and recovering the 2-methyl-1,3-propanediol.
Claim 2
Dependent Claim 173 words
A continuous process for the preparation of 2-methyl-1,3-propanediol which comprises (a) reacting acrolein with a 1,3-aliphatic diol with 3 to 7 carbon atoms other than 2-methyl-1,3-propanediol under conventional conditions to prepare a cyclic acetal; (b) hydroformylating the cyclic acetal in the presence of a rhodium complex catalyst comprising rhodium carbonyl and a phosphite ligand of the formula ##STR5## wherein R 1 , R 2 and R 3 are the same or different phenyl, substituted phenyl or alkyl groups having 1 to 12 carbon atoms under conventional conditions to prepare the aldehyde of the cyclic acetal; (c) hydrogenating and hydrolyzing the aldehyde of the cyclic acetal in the presence of a hydrogenation catalyst and an ion exchange catalyst to prepare 1,4-butanediol and a mixture of diols; (d) separating the mixture of diols from 1,4-butanediol; (e) recycling said mixture back to step (a) to react with acrolein in place of the diol of (a) for a number of cycles until a product consisting of 1,4-butanediol and essentially 2-methyl-1,3-propanediol; and (f) separating and recovering the 2-methyl-1,3-propanediol.
Claim 3
Dependent Claim 11 words
The process of claim 1 wherein the aliphatic diol is 1,3-butanediol.
Claim 4
Dependent Claim 12 words
The process of claim 1 wherein the aliphatic diol is 2,2'-dimethyl propanediol.
Claim 5
Dependent Claim 11 words
The process of claim 1 wherein the aliphatic diol is 2-methyl-2,4-pentanediol.
Claim 6
Dependent Claim 11 words
The process of claim 1 wherein the aliphatic diol is 1,3-propanediol.
Claim 7
Dependent Claim 33 words
The process of claim 1 wherein the composition of the 2-methyl-1,3-propanediol in the final product is from 90 to 99% by weight of more 2-methyl-1,3-propanediol and the remainder is the starting aliphatic diol.
Claim 8
Dependent Claim 11 words
The process of claim 6 wherein the aliphatic diol is 1,3-butanediol.
Claim 9
Dependent Claim 28 words
The process of claim 1 wherein the composition of the 2-methyl-1,3-propanediol in the final product is 99% or more 2-methyl-1,3-propanediol and the remainder is the starting aliphatic diol.
Claim 10
Dependent Claim 11 words
The process of claim 8 wherein the aliphatic diol is 1,3-butanediol.
Claim 11
Dependent Claim 27 words
The process of claim 1 wherein the rhodium concentration is 1.0 × 10 -3 to 6.0 × 10 -3 gram atoms per mole of the cyclic acetal.
Claim 12
Dependent Claim 16 words
The process of claim 1 wherein the aliphatic diol is 1,3-butanediol, 1,3-propanediol, 2,2-dimethyl propanediol or 2-methyl-2,4-pentanediol.

References Cited (Backward Citations)

US4017550A Cited
US3929915A Cited
US3963755A Cited
US3963754A Cited
US4024197A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1981-06-19 1981-12-19 1982-06-20 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1985-06-19 1985-12-19 1986-06-20 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1989-06-19 1989-12-19 1990-06-20 $7700.00 Window Closed / Lapsed

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