US4962243A
Expired / Lapsed
US
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Preparation of octadienols
Assignee: BASF SE
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Filing: 1989-02-24
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Granted: 1990-10-09
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Expires: 2009-02-24
Abstract
Abstract Octadienols are prepared by teleomerization of 1,3-butadiene with water in the presence of carbon dioxide and a catalyst system comprising a palladium compound and a tertiary phosphorus compound by performing the reaction in the presence of a strong non-coordinating acid.
Inventors
- 👤 Michael Roeper
- 👤 Werner Bertleff
- 👤 Dieter Koeffer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 09:38
CPC Classifications
C; C07; C07C; C07C29/00; C07C29/36
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
77 words
A process for preparing an octadienol, comprising: telomerizing 1,3-butadiene with water in the presence of carbon dioxide, a non-coordinating acid and a catalyst system comprised of a palladium compound and a tertiary phosphorus compound, the ratio of acid to palladium in said palladium compound ranging from 0.1:150 equivalent % per mole of palladium and the amount of palladium compound employed relative to butadiene reactant ranging from 10 -5 to 0.1 mole of palladium per mole of butadiene.
Claim 2
Dependent Claim
77 words
A process for preparing an octadienol, comprising: telomerizing 1,3-butadiene with water in the presence of carbon dioxide, a non-coordinating acid and a catalyst system comprised of a palladium compound and a tertiary phosphorus compound, the ratio of acid to palladium in said palladium compound ranging from 0.1:150 equivalent % per mole of palladium and the amount of palladium compound employed relative to butadiene reactant ranging from 10 -5 to 0.1 mole of palladium per mole of butadiene.
Claim 3
Dependent Claim
38 words
The process of claim 1, wherein said non-coordinating acid is a member selected from the group consisting of tetrafluoroboric acid, hexafluorophosphoric acid, methanesulfonic acid, trifluoromethane sulfonic acid, p-toluenesulfonic acid, sulfuric acid, trilfuoroacetic acid, trichloroacetic acid and acetic acid.
Claim 4
Dependent Claim
11 words
The process of claim 1, wherein said ratio ranges from 50:100.
Claim 5
Dependent Claim
17 words
The process of claim 1, wherein the palladium compound is a palladium (0) or palladium (II) compound.
Claim 6
Dependent Claim
44 words
The process of claim 4, wherein said palladium compound is Pd(acac) 2 , Pd(OAc) 2 , Pd(PPh 3 ) 4 , Pd(dba) 2 , [Pd(acac)(PPh 3 ) 2 ]BF 4 , [Pd(h 3 -C 3 H 5 )(COD)]BF 4 , or [Pd(acac)(COD)]BF 4 .
Claim 7
Dependent Claim
25 words
The process of claim 1, wherein said amount of palladium compound ranges from 10 -4 to 10 -2 mole of palladium per mole of butadiene.
Claim 8
Dependent Claim
20 words
The process of claim 1, wherein said tertiary phosphorus compound is a trialkylphosphine, a triarylphosphine, a trialkylphosphite or a triarylphosphite.
Claim 9
Dependent Claim
27 words
The process of claim 1, wherein the amount of tertiary phosphorus compound as a ligand ranges from 1 to 20 moles per mole of said palladium compound.
Claim 10
Dependent Claim
19 words
The process of claim 8, wherein said amount of phosphorus ligand ranges from 1-5 moles per mole of palladium.
Claim 11
Dependent Claim
23 words
The process of claim 1, wherein the amount of carbon dioxide present ranges from 10 -3 to 1 mole per mole of butadiene.
Claim 12
Dependent Claim
21 words
The process of claim 10, wherein said amount of carbon dioxide ranges from 10 -2 to 0.5 mole of carbon dioxide.
Claim 13
Dependent Claim
25 words
The process of claim 1, wherein the amount of water in the reaction system is at least an equimolar amount with respect to butadiene reactant.
Claim 14
Dependent Claim
23 words
The process of claim 1, wherein the reaction medium further contains an aprotic polar solvent in which water and 1,3-butadiene are partially soluble.
Claim 15
Dependent Claim
19 words
The process of claim 13, wherein the aprotic solvent has a boiling point higher than the octadienol product prepared.
Claim 16
Dependent Claim
13 words
The process of claim 14, wherein said solvent is a polyalkylene glycol ether.
Claim 17
Dependent Claim
13 words
The process of claim 14, wherein said solvent is a sulfoxide or sulfone.
Claim 18
Dependent Claim
23 words
The process of claim 1, wherein said 1,3-butadiene reactant is a mixture of said 1,3-butadiene with another saturated or olefinic C 4 hydrocarbon.
Claim 19
Dependent Claim
17 words
The process of claim 1, wherein said reaction is conducted at a temperature ranging from 50°-70° C.
Claim 20
Dependent Claim
18 words
The process of claim 1, wherein the telomerization reaction is conducted under a pressure ranging from 5-50 bar.
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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) | 1993-10-08 | 1994-04-09 | 1994-10-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-10-08 | 1998-04-09 | 1998-10-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-10-08 | 2002-04-09 | 2002-10-09 | $7700.00 | Window Closed / Lapsed |