US4200716A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for polymerizing acetylene
Assignee: Honeywell International Inc
•
Filing: 1978-11-03
•
Granted: 1980-04-29
•
Expires: 1998-11-03
Abstract
Abstract A process is described for polymerizing acetylene to selectively produce partially crystalline polyacetylene in its cis and trans configurations, which when doped with halogen additives, are useful as electrical conductors or semi-conductors. The polymerization is conducted in a solution containing a lithium dicyclopentadienyl titanium hydride catalyst in a liquid organic solvent therefor, at a temperature in the range of about -120° to +250° C. Lower process temperatures, such as below -60° C., favor the formation of the cis form, and higher temperatures, above 0° C., favor the formation of the trans form.
Inventors
- 👤 Guido Pez
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 13:36
CPC Classifications
C; C07; C07F; C07F17/00; C07C; C07C2/00; C07C2/02; C07C2/04; C07C2/06; C07C2/08; C07C2/26; C07C2/32; C07C2/34; C07F7/00; C07F7/28; C07C2531/00; C07C2531/16; C07C2531/22
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
168 words
A process for producing polyacetylene comprising contacting acetylene with a solution comprised of a liquid inert organic solvent and a lithium dicyclopentadienyl titanium hydride catalyst of the formula, LiRR'TiH, wherein R and R' are cyclopentadienyl rings, of the empirical formula, C 5 H 5 , wherein the ring hydrogens may be independently substituted with one or more groups inert toward lithium metal, said rings being bonded to titanium by sigma-bonds, pi-bonds or mixtures thereof, and said catalyst exhibiting a 13 C nuclear magnetic resonance spectrum in deuterated benzene in which observed values for the chemical shifts of the ring carbons in R are different from the observed values for ring carbon atoms in R', and said catalyst exhibiting an infrared spectrum in deuterated n-hexadecane in which a titanium metal-hydride absorption band is observed in the region of about 1250-1450 cm -1 , at a temperature at about -120° to +200° C., under a pressure of about 0.01 to 10 atmospheres, in the absence of elemental oxygen and water.
Claim 2
Dependent Claim
168 words
A process for producing polyacetylene comprising contacting acetylene with a solution comprised of a liquid inert organic solvent and a lithium dicyclopentadienyl titanium hydride catalyst of the formula, LiRR'TiH, wherein R and R' are cyclopentadienyl rings, of the empirical formula, C 5 H 5 , wherein the ring hydrogens may be independently substituted with one or more groups inert toward lithium metal, said rings being bonded to titanium by sigma-bonds, pi-bonds or mixtures thereof, and said catalyst exhibiting a 13 C nuclear magnetic resonance spectrum in deuterated benzene in which observed values for the chemical shifts of the ring carbons in R are different from the observed values for ring carbon atoms in R', and said catalyst exhibiting an infrared spectrum in deuterated n-hexadecane in which a titanium metal-hydride absorption band is observed in the region of about 1250-1450 cm -1 , at a temperature at about -120° to +200° C., under a pressure of about 0.01 to 10 atmospheres, in the absence of elemental oxygen and water.
Claim 3
Dependent Claim
34 words
The process of claim 1 wherein R and R' of said catalyst are both unsubstituted cyclopentadienyl rings, said catalyst having the formula, Li (η-C 5 H 5 ) (C 5 H 5 ) TiH.
Claim 4
Dependent Claim
24 words
the process of claim 1 wherein said temperature is about 60° to 200° C. and the resulting polyacetylene is substantially in the trans configuration.
Claim 5
Dependent Claim
24 words
The process of claim 1 wherein said temperature is about -110° to -60° C. and the resulting polyacetylene is substantially in the cis configuration.
Claim 6
Dependent Claim
12 words
The process of claim 1 conducted at about 1 atmosphere of pressure.
Claim 7
Dependent Claim
89 words
The process of claim 1 wherein said solvent is a C 6 -C 14 aromatic hydrocarbon, C 5 -C 18 linear or branched acyclic or cyclic saturated aliphatic hydrocarbon, C 4 -C 6 saturated aliphatic cyclic mono- or diether, C 2 -C 6 linear or branched acyclic saturated aliphatic mono- or diether, C 7 -C 10 aromatic mono- or diether, C 3 -C 8 linear or branched saturated aliphatic tertiary amine, C 4 -C 12 cyclic monoolefin, C 5 -C 8 linear or branched acyclic alpha-olefin, or mixtures thereof.
Claim 8
Dependent Claim
26 words
The process of claim 6 wherein said solvent is toluene, hexane, benzene, tetrahydrofuran, dioxane, diethyl ether, 1,2-dimethoxyethane, anisole, n-hexadecane, cyclohexane, triethylamine, cyclohexene, hexene, or mixtures thereof.
Claim 9
Dependent Claim
18 words
the process of claim 1 wherein said solution is further comprised of a chelating agent for lithium cation.
Claim 10
Dependent Claim
11 words
The process of claim 8 wherein said chelating agent is N,N,N',N'-tetramethylethylenediamine.
Claim 11
Dependent Claim
26 words
The process of claim 1 wherein said catalyst is present in an amount of about 1 part catalyst per 1000 to 10,000 parts by weight solvent.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-04-29 | 1983-10-29 | 1984-04-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-04-29 | 1987-10-29 | 1988-04-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-04-29 | 1991-10-29 | 1992-04-29 | $7700.00 | Window Closed / Lapsed |