IP Library Granted Patent US 9,738,662
Granted Patent B2
US 9,738,662 · App. 14/434,132 · Granted Aug 22, 2017

Process for producing tetrakis(

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Quick Facts
Patent No.
US 9,738,662
App. No.
14/434,132
Granted
Aug 22, 2017
Kind
B2
Abstract

This invention provides processes for forming halomagnesium tetrakis( F aryl)borates, which processes comprise bringing together, in an anhydrous liquid organic medium, at least one boron trihalide; at least one F aryl Grignard reagent; and at least one copper compound. Also provided are processes for forming halomagnesium tetrakis( F aryl)borates, which processes comprise bringing together, in an anhydrous liquid organic medium, at least one boron trihalide; at least one copper compound; magnesium metal; and at least one polyhaloaromatic compound.

Claims (31)

1. A process comprising bringing together, in an anhydrous liquid organic medium, either

A) at least one boron trihalide;

at least one F aryl Grignard reagent; and

at least one copper compound,

or

B) at least one boron trihalide;

at least one copper compound;

magnesium metal; and

at least one polyhaloaromatic compound,

to form a halomagnesium tetrakis( F aryl)borate.

2. A process as in claim 1 wherein in B) either

i) at least one boron trihalide, magnesium metal, and at least one copper compound are brought together to form a mixture, and

ii) at least a portion of the mixture formed in i) and at least one polyhaloaromatic compound are brought together;

or

a) at least one copper compound and magnesium metal are brought together to form a mixture, and

b) at least a portion of the mixture formed in a) and a mixture of at least one boron trihalide and at least one polyhaloaromatic compound are brought together.

3. A process as in claim 1 wherein in A),

the copper compound is in an amount that provides about 0.001 mmol or more of copper per mole of F aryl Grignard reagent;

the F aryl Grignard reagent is pentafluorophenyl chloromagnesium, pentafluorophenyl bromomagnesium, heptafluoronaphthyl chloromagnesium, or heptafluoronaphthyl bromomagnesium; and/or

the F aryl Grignard reagent and the boron trihalide are in amounts that provide a molar ratio of about 3.9:1 to about 4.5:1.

4. A process as in claim 1 wherein the copper compound is a copper(I) halide and/or a copper(II) halide.

5. A process as in claim 1 wherein the copper compound is selected from copper(I) chloride, copper(I) bromide, bromotris(triphenylphosphine)copper(I), copper(II) chloride, copper(II) bromide, or mixtures of any two or more of the foregoing.

6. A process as in claim 3 wherein the copper compound is in an amount that provides about 0.001 mmol to about 40 mmol of copper per mole of F aryl Grignard reagent.

7. A process as in claim 1 wherein in B)

the polyhaloaromatic compound is chloropentafluorobenzene, bromopentafluorobenzene, chloroheptafluoronaphthylene, or bromoheptafluoronaphthylene;

the copper compound is in an amount that provides about 0.001 mmol or more of copper per mole of polyhaloaromatic compound; and/or

the polyhaloaromatic compound and the boron trihalide are in amounts that provide a molar ratio of about 3.9:1 to about 4.5:1.

8. A process as in claim 7 wherein the copper compound is in an amount that provides about 0.001 mmol to about 40 mmol of copper per mole of polyhaloaromatic compound.

9. A process as in claim 1 wherein the liquid organic medium is an ether-containing medium, and/or wherein the boron trihalide is boron trifluoride or a boron trifluoride-solvent complex.

10. A process as in claim 1 wherein the boron trihalide is boron trifluoride diethyl etherate complex.

11. A process as in claim 1 wherein the process is conducted at a temperature in the range of about −20° C. to about 60° C.

Assignments (7)
RELEASE OF SECURITY INTEREST SUPPLEMENT NO. 1, RECORDED AT REEL/FRAME 063237/0252 Recorded Feb 2, 2026
From: WILMINGTON TRUST, NATIONAL ASSOCIATION
To: W. R. GRACE & CO.-CONN.
Reel/Frame 074612/0939 →
NOTES SECURITY INTEREST Recorded Jan 29, 2026
From: W. R. GRACE & CO.-CONN.; ADVANCED REFINING TECHNOLOGIES LLC
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 074532/0229 →
SECURITY AGREEMENT (NOTES) Recorded Aug 19, 2025
From: W. R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 072520/0653 →
SECURITY INTEREST Recorded Apr 2, 2023
From: W. R. GRACE & CO.-CONN.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 063237/0262 →
SECURITY INTEREST Recorded Apr 2, 2023
From: W. R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 063237/0252 →
SECURITY INTEREST Recorded Feb 17, 2023
From: W.R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 062792/0510 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 31, 2018
From: ALBEMARLE CORPORATION
To: W. R. GRACE & CO-CONN.
Reel/Frame 045946/0786 →