US3911032A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for preparing 2-butene-1,4-diol from dichlorobutenes
Assignee: Tosoh Corp
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Filing: 1972-11-01
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Granted: 1975-10-07
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Expires: 1992-11-01
Abstract
Abstract A process for preparing 2-butene-1,4-diol from dichlorobutenes which comprises hydrolyzing dichlorobutenes in the presence of water by using a water soluble formate of a metal selected from the group consisting of group Ia and IIa of the Periodic table. As a modification of the above mentioned process, an elemental metal selected from the group consisting of copper, iron and zinc or a compound thereof is further added to said reaction system as a catalyst thereby converting substantially all of mixture of isomeric dichlorobutenes into the desired 2-butene-1,4-diol.
Inventors
- 👤 Toshio Sakomura
- 👤 Hisashi Kisaki
- 👤 Shunsuke Mabuchi
- 👤 Yukihiro Tsutsumi
- 👤 Takashi Tada
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 21:45
CPC Classifications
C; C07; C07C; C07C33/00; C07C33/02; C07C33/025; C07C33/035; G; G01; G01G; G01G13/00; G01G13/02; G01G13/04; G01G13/08
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
105 words
A PROCESS FOR PREPARING 2-BUTENE-1,4-DIOL FROM 1,4DICHLORO-2-BUTENE OR A MIXTURE OF DICHLOROBUTENES RICH IN 1,4-DICHOLRO-2-BUTENE IN A REACTION CHARGE OF (1) HYDROLYZING 1,4-DICHLORO-2-BUTENE IN A REACTION CHARGE OF (1) SAID 1,4-DICHOLRO-2-BUTENE, (2) WATER AND (3) A WATER SOLUBLE FORMATE OF A METAL SELECTED FROM THE GROUP CONSISTING OF METALS OF 1A AND GROUP 11A OF THE PERIODIC TABLE AT A TEMPERATURE OF FROM 70*C, TO 150*C., THE CONCENTRATION OF THE AQUEOUS SOLUTION OF SAID FORMATE BEING FROM ABOUT 3 TO ABOUT 80 PERCENT BY WEIGHT AND THE EQUIVALENT RATIO OF SAID FORMULAE TO SVAID DICHLOROBUTENE BEING WITHIN A RANGE FROM ABOUT 3:1 TO ABOUT 0.8:1.
Claim 2
Dependent Claim
105 words
A PROCESS FOR PREPARING 2-BUTENE-1,4-DIOL FROM 1,4DICHLORO-2-BUTENE OR A MIXTURE OF DICHLOROBUTENES RICH IN 1,4-DICHOLRO-2-BUTENE IN A REACTION CHARGE OF (1) HYDROLYZING 1,4-DICHLORO-2-BUTENE IN A REACTION CHARGE OF (1) SAID 1,4-DICHOLRO-2-BUTENE, (2) WATER AND (3) A WATER SOLUBLE FORMATE OF A METAL SELECTED FROM THE GROUP CONSISTING OF METALS OF 1A AND GROUP 11A OF THE PERIODIC TABLE AT A TEMPERATURE OF FROM 70*C, TO 150*C., THE CONCENTRATION OF THE AQUEOUS SOLUTION OF SAID FORMATE BEING FROM ABOUT 3 TO ABOUT 80 PERCENT BY WEIGHT AND THE EQUIVALENT RATIO OF SAID FORMULAE TO SVAID DICHLOROBUTENE BEING WITHIN A RANGE FROM ABOUT 3:1 TO ABOUT 0.8:1.
Claim 3
Dependent Claim
12 words
A process of claim 1, wherein the starting material employed is 1,4-dichloro-2-butene.
Claim 4
Dependent Claim
18 words
A process of claim 1, wherein said mixture of dichlorobutenes is obtained from vapor phase chlorination of butadiene.
Claim 5
Dependent Claim
22 words
A process of claim 1, wherein said formate is selected from the group consisting of sodium formate, potassium formate and calcium formate.
Claim 6
Dependent Claim
45 words
A process of claim 1, wherein a hydroxide, carbonate or bicarbonate of the metal corresponding to the cation of said formate is added to the resulting reaction mixture, the amount of said hydroxide, carbonate or bicarbonate being chemically eqivalent to the amount of said dichlorobutene.
Claim 7
Dependent Claim
142 words
A process for preparing 2-butene-1,4-diol from a mixture of dichlorobutenes by a hydrolysis reaction comprising hydrolyzing a reaction charge of (1) a mixture of dichlorobutenes, (2) water, (3) a water soluble formate of a metal selected from the group consisting of metals of group Ia and group IIa of the periodic table, and (4) a member selected from the group consisting of copper, iron, zinc, and a halide, oxide, hydroxide, carbonate or lower aliphatic acid salt thereof as a catalyst, at a temperature of from 70*C. to 150*C., the concentration of the aqueous solution of said formate being in a range of from about 3 to about 80 percent by weight and the molar ratio of said formate to said dichlorobutene being within a range of from about 3:1 to about 0.8:1, whereby substantially all of said dichlorobutenes are converted into 2-butene-1,4-diol.
Claim 8
Dependent Claim
142 words
A process for preparing 2-butene-1,4-diol from a mixture of dichlorobutenes by a hydrolysis reaction comprising hydrolyzing a reaction charge of (1) a mixture of dichlorobutenes, (2) water, (3) a water soluble formate of a metal selected from the group consisting of metals of group Ia and group IIa of the periodic table, and (4) a member selected from the group consisting of copper, iron, zinc, and a halide, oxide, hydroxide, carbonate or lower aliphatic acid salt thereof as a catalyst, at a temperature of from 70*C. to 150*C., the concentration of the aqueous solution of said formate being in a range of from about 3 to about 80 percent by weight and the molar ratio of said formate to said dichlorobutene being within a range of from about 3:1 to about 0.8:1, whereby substantially all of said dichlorobutenes are converted into 2-butene-1,4-diol.
Claim 9
Dependent Claim
25 words
A process of claim 6, wherein the amount of catalyst employed is within a range of 0.01 - 10% by weight based on dichlorobutenes employed.
Claim 10
Dependent Claim
22 words
A process of claim 6, wherein said formate is selected from the group consisting of sodium formate, potassium formate and calcium formate.
Claim 11
Dependent Claim
29 words
A process of claim 6, wherein said catalyst is selected from the group consisting of halide, oxide, hydroxide, carbonate and lower aliphatic acid salt of copper, iron and zinc.
Claim 12
Dependent Claim
20 words
A process of claim 6, wherein said catalyst is selected from the group consisting of copper formate and copper chloride.
Claim 13
Dependent Claim
18 words
A process of claim 6, wherein said mixture of dichlorobutenes is obtained from vapor phase chlorination of butadiene.
Claim 14
Dependent Claim
45 words
A process of claim 6, wherein a hydroxide, carbonate or bicarbonate of the metal corresponding to the cation of said formate is added to the resulting reaction mixture, the amount of said hydroxide, carbonate or bicarbonate being chemically equivalent to the amount of said dichlorobutene.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-10-06 | 1979-04-07 | 1979-10-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-10-06 | 1983-04-07 | 1983-10-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-10-06 | 1987-04-07 | 1987-10-07 | $7700.00 | Window Closed / Lapsed |