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US4093633A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for preparing tetrahydrofuran

Assignee: Mitsubishi Chemical Corp
•
Filing: 1977-01-28
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Granted: 1978-06-06
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Expires: 1997-01-28
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Abstract

Abstract In the process for preparing tetrahydrofuran by the dehydrocyclization of 1,4-butanediol in the presence of a non-volatile acid catalyst, wherein vapor mixture of water and tetrahydrofuran is continuously taken out from the reaction zone and subjected to the azeotropic distillation in three distillation columns operated under specified conditions thereby obtaining tetrahydrofuran of high quality in a high yield.

Inventors

  • 👤 Yasuo Tanabe
  • 👤 Jun Toriya
  • 👤 Masato Sato
  • 👤 Ken Shiraga

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 04:08
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/04; C07D307/06; C07D307/08

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 240 words
A process for preparing tetrahydrofuran by the dehydrocyclization reaction of 1,4-butanediol in the presence of an acid catalyst, consisting essentially of; (a) supplying 1,4-butanediol and a non-volatile acid catalyst to a reaction zone, (b) reacting said butanediol and said catalyst at a temperature between above the boiling point of an azeotropic mixture of water and tetrahydrofuran and below the boiling point of 1,4-butanediol, (c) continuously removing a vapor mixture of water and tetrahydrofuran from said reaction zone, (d) supplying said vapor mixtures to a first distillation column maintained under a pressure lower than that in said reaction zone and in the range of from atmospheric pressure to 3 kg/cm 2 gauge, (e) distilling a first azeotropic mixture of water and tetrahydrofuran to form a first distillate, (f) supplying said first distillate to a second distillation column maintained under a pressure higher than that in said first distillation column by 3 to 20 kg/cm 2 gauge, (g) distilling a second azeotropic mixture of water and tetrahydrofuran from the top of said second distillation column to form a second distillate, (h) recycling said second distillate to said first distillation column, (i) supplying a substantially water-free-bottom of said second distillation column to a third distillation column maintained under atmospheric pressure or a pressure slightly higher than atmospheric pressure, (j) recycling the bottom of said third distillation column into said reaction zone, and (k) obtaining tetrahydrofuran from the top of said third distillation column.
Claim 2
Dependent Claim 240 words
A process for preparing tetrahydrofuran by the dehydrocyclization reaction of 1,4-butanediol in the presence of an acid catalyst, consisting essentially of; (a) supplying 1,4-butanediol and a non-volatile acid catalyst to a reaction zone, (b) reacting said butanediol and said catalyst at a temperature between above the boiling point of an azeotropic mixture of water and tetrahydrofuran and below the boiling point of 1,4-butanediol, (c) continuously removing a vapor mixture of water and tetrahydrofuran from said reaction zone, (d) supplying said vapor mixtures to a first distillation column maintained under a pressure lower than that in said reaction zone and in the range of from atmospheric pressure to 3 kg/cm 2 gauge, (e) distilling a first azeotropic mixture of water and tetrahydrofuran to form a first distillate, (f) supplying said first distillate to a second distillation column maintained under a pressure higher than that in said first distillation column by 3 to 20 kg/cm 2 gauge, (g) distilling a second azeotropic mixture of water and tetrahydrofuran from the top of said second distillation column to form a second distillate, (h) recycling said second distillate to said first distillation column, (i) supplying a substantially water-free-bottom of said second distillation column to a third distillation column maintained under atmospheric pressure or a pressure slightly higher than atmospheric pressure, (j) recycling the bottom of said third distillation column into said reaction zone, and (k) obtaining tetrahydrofuran from the top of said third distillation column.
Claim 3
Dependent Claim 47 words
The process for preparing tetrahydrofuran according to claim 1, wherein 1,4-butanediol is prepared by hydrogenating 1,4-diacetoxybutene, which is produced by the acetoxylation of butadiene, into 1,4-diacetoxybutane and hydrolyzing said 1,4-diacetoxybutane as the hydrogenated products in the presence of a solid acid catalyst and distilling hydrolyzates thus obtained.
Claim 4
Dependent Claim 19 words
The process for preparing tetrahydrofuran according to claim 1, wherein the non-volatile acid catalyst is a liquid acid catalyst.
Claim 5
Dependent Claim 17 words
The process for preparing tetrahydrofuran according to claim 3, wherein the non-volatile liquid acid is sulfuric acid.
Claim 6
Dependent Claim 22 words
The process for preparing tetrahydrofuran according to claim 4, wherein sulfuric acid is fed continuously to the reactor together with crude 1,4-butanediol.
Claim 7
Dependent Claim 22 words
The process for preparing tetrahydrofuran according to claim 1, wherein the reaction temperature is in the range of 90° to 220° C.
Claim 8
Dependent Claim 26 words
The process for preparing tetrahydrofuran according to claim 1, wherein the first and second distillation columns are operated with 5 to 30 number of theoretical plates.
Claim 9
Dependent Claim 24 words
The process for preparing tetrahydrofuran according to claim 1, wherein the third distillation column is operated with 10 to 30 number of theoretical plates.
Claim 10
Dependent Claim 26 words
The process for preparing tetrahydrofuran according to claim 1, wherein the first and second distillation columns are operated with a reflux ratio of 0.5 to 5.
Claim 11
Dependent Claim 24 words
The process for preparing tetrahydrofuran according to claim 1, wherein the third distillation column is operated with a reflux ratio of 0.5 to 2.0.

References Cited (Backward Citations)

SU174636A1 Cited
CA546591A Cited
US2544899A Cited
GB1170222A Cited
US3694465A Cited
US3726905A Cited

USPTO Annuity & Maintenance Windows

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

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