Mono-substituted cyclopentadienes and metal cyclopentadienyl complexes and synthesis methods thereof

Patent metadata

Field	Value
Publication number	US-12091374-B2
Application number	US-202217578512-A
Country	US
Kind code	B2
Filing date	Jan 19, 2022
Priority date	Aug 13, 2020
Publication date	Sep 17, 2024
Grant date	Sep 17, 2024

Abstract

A metal cyclopentadienyl complex has the formula:

wherein m≥0; M is a Group I, II or III main group metal, alkali or transition metal; C 5 H 4 represents a Cp ring where two hydrogens are substituted by M and R(F) m ; R(F) m is connected to any one of the carbon atoms of the Cp and selected from a hydrocarbyl, fluorohydrocarbyl, silyl group [SiR′ 3 ], or amino group [—NR 1 R 2 ]. The metal cyclopentadienyl complexes include Li(C 5 H 4 -2-C 5 H 11 ) (CAS No: 2413046-23-6), K(C 5 H 4 -2-C 5 H 11 ), Na(C 5 H 4 -2-C 5 H 11 ), K(C 5 H 4 -1-F—C 4 H 10 ), K(C 5 H 4 -1,1,1-3F—C 4 H 6 ), Li(C 5 H 4 -2-C 4 H 9 ), or In(C 5 H 4 -2-C 5 H 11 ) (CAS No.: 2364634-67-1).

A mono-substituted cyclopentadiene has the formula:

wherein m≥0; C 5 H 5 represents the Cp ring where one hydrogen is substituted R(F) m ; R(F) m is connected to any one of the carbon atoms of the Cp and selected from a hydrocarbyl, fluorohydrocarbyl, silyl group [SiR′ 3 ], or amino group [—NR 1 R 2 ]. The mono-substituted cyclopentadienes include C 5 H 5 -1-F—C 4 H 10 , C 5 H 5 -2-C 5 H 11 , C 5 H 5 -2-C 4 H 9 , or C 5 H 5 -1,1,1-3F—C 4 H 6 .

First claim

What is claimed is:

1. A metal cyclopentadienyl complex having the following formula:

wherein m≥0; M is an alkali or transition metal; C 5 H 4 represents a cyclopentadienyl (Cp) ring where two hydrogens are substituted by M and R(F) m , respectively; R(F) m is connected to any one of the carbon atoms of the Cp and selected from
a C 1 -C 8 linear or branched, saturated or unsaturated fluorohydrocarbyl group containing at least one fluorine.

2. The metal cyclopentadienyl complex of claim 1 , wherein R is selected from n-Pr, i-Pr, n-Bu, i-Bu, 2-Bu, n-Pent, i-Pent, 2-Pent, n-Hex, i-Hex, 2-Hex, n-Hept, i-Hept, 2-Hept, —CF 3 , −1,1,1-trifluoropropane (−1,1,1-PrF 3 ), −1,1,1-trifluorobutane (−1,1,1-BuF 3 ), or −1-fluorobutane (−1,1,1-BuF).

3. The metal cyclopentadienyl complex of claim 1 , wherein M is selected from K, Na, Sr, Ba, Ga, In, Y or Yb.

4. The metal cyclopentadienyl complex of claim 1 being Li(C 5 H 4 -2-C 5 H 11 ) (Li(Cp-2-Pent), CAS No: 2413046-23-6), K(C 5 H 4 -2-C 5 H 11 ) (K(Cp-2-Pent)), Na(C 5 H 4 -2-C 5 H 11 ) (Na(Cp-2-Pent)), K(C 5 H 4 -1-F—C 4 H 10 ) (K(Cp-1-F-Bu)), K(C 5 H 4 -1,1,1-3F—C 4 H 6 ) (K(Cp-1,1,1-3F-Bu)), Li(C 5 H 4 -2-C 4 H 9 ) (Li(Cp-2-Bu)), or In(C 5 H 4 -2-C 5 H 11 ) (In(Cp-2-Pent), CAS No.: 2364634-67-1).

5. The metal cyclopentadienyl complex of claim 1 being In(C 5 H 4 -2-C 5 H 11 ) (In(Cp-2-Pent), CAS No.: 2364634-67-1).

6. The metal cyclopentadienyl complex of claim 1 being Li(C 5 H 4 -2-C 5 H 11 ) (Li(Cp-2-Pent), CAS No: 2413046-23-6).

Assignees

• Air Liquide

Inventors

• Nikiforov Grigory

Classifications

• B01J31/0268

  Phosphonium compounds, i.e. phosphine with an additional hydrogen or carbon atom bonded to phosphorous so as to result in a formal positive charge on phosphorous · CPC title

• C07C22/02

  having unsaturation in the rings · CPC title

• C07C17/38

  Separation; Purification; Stabilisation; Use of additives · CPC title

• B01J2531/90

  Catalytic systems characterized by the solvent or solvent system used · CPC title

• C07F17/00 Primary

  Metallocenes · CPC title