Method of forming alkoxylated fluoroalcohols

Patent metadata

Field	Value
Publication number	US-9950978-B2
Application number	US-201514613222-A
Country	US
Kind code	B2
Filing date	Feb 3, 2015
Priority date	Dec 3, 2007
Publication date	Apr 24, 2018
Grant date	Apr 24, 2018

Abstract

A method of forming an alkoxylated fluoroalcohol is accomplished by providing a boron compound having or providing at least one boron-oxygen bond and an iodine source. The boron compound and iodine source are combined with reactants of a fluoroalcohol and an alkylene oxide in the presence of a base. The reactants are allowed to react to form an alkoxylated fluoroalcohol reaction product.

First claim

I claim:

1. A process of forming alkoxylated fluoroalchohols, wherein the process comprises the steps of:
reacting
(A) a boron and iodine based catalyst system, wherein boron is provided by at least one boron compound selected from the group consisting of an oxide of boron, an alkyl borate, a boric acid, a boronic acid anhydride, a boronic acid, salts of said acids, esters of said acids, and combinations thereof, and iodine is provided by at least one iodine source selected from the group consisting of an alkali metal iodide, alkaline earth metal iodide, elemental iodine and combinations thereof;
(B) one or more fluoroalcohols of the formla F(CF 2 ) m —(CH 2 ) n —OH , where m is 2-20 and n is 1-6; and
(C) a 1,2 alkylene oxide of the formula

wherein R 9 , R 10 , R 11 , and R 12 are each independently hydrogen or alkyl,
at a temperature from about ambient to about 200° C.
and a pressure from ambient atmospheric pressure to reactant pressure.

2. The process of claim 1 , wherein the catalyst system comprises an alkyl borate.

3. The process of claim 1 , wherein said boron compound is selected from the group consisting of trimethyl borate, triethyl borate, triisopropyl borate, tripropyl borate, tributyl borate, sodium tetraborate, potassium tetraborate and combinations thereof.

4. The process of claim 1 , wherein the 1,2 alkylene oxide is used in an amount of from about 1 mole % to about 100 mole % by total moles of the fluoroalcohol.

5. The process of claim 1 , wherein said process is carried out in the presence of an aprotic solvent.

6. The process of claim 1 , wherein the iodine source is added in an amount from about 0.05% to 10% by weight of the fluoroalcohol.

7. The process of claim 1 , wherein the boron source is added in an amount from about 0.01 mole % to 20 mole % by moles of the fluoroalcohol.

8. The process of claim 1 , wherein the alkylene oxide comprises one or more alkylene oxides of ethylene oxide, propylene oxide or butylene oxide.

9. The process of claim 1 , wherein the alkylene oxide is ethylene oxide.

Assignees

• Tyco Fire & Security Gmbh

Inventors

• Martin Thomas Joseph

Classifications

• C07C231/12

  by reactions not involving the formation of carboxamide groups · CPC title

• C07C41/03 Primary

  by reaction of oxirane rings with hydroxy groups · CPC title

• C07C311/09

  the carbon skeleton being further substituted by at least two halogen atoms · CPC title

• C07C303/40

  by reactions not involving the formation of sulfonamide groups · CPC title

• C07C43/11

  Polyethers containing —O—(C—C—O—)n units with ≤ 2 n≤ 10 · CPC title