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US 2026/0193531 A1Published application
Liquid weighting agents for oil-based fluids
AssigneeAlbemarle Corporation
InventorsYunqi LIU, Joseph BAKER, Huaxiang YANG, Garrett NIELSEN, Donovan THOMPSON, Gilles L. NUMKAM, Tse-Chong WU
Life of this patent
Estimating the term…
Abstract
This invention provides compositions that can be used as oil-miscible liquid weighting agents.
Claims23
A liquid weighting agent containing two or more bromine atoms and having a bromine content of about 35 wt % or more, which liquid weighting agent is selected from
- A) a bromine-containing monoester represented by the formula
- wherein R1 contains a quaternary carbon atom, a terminal alkene moiety, or an aromatic-alkyl moiety, wherein the oxygen atom adjacent to R1 is not bound to a quaternary carbon atom, an alkenyl carbon atom or an aromatic carbon atom, and R2 is a hydrocarbyl group or a bromine-containing hydrocarbyl group, wherein the bromine-containing monoester is
- i) a bromine-containing monoester that has seven or more carbon atoms and R1 contains a quaternary carbon atom,
- ii) a bromine-containing monoester that has five or more carbon atoms and R1 contains a terminal alkene moiety,
- iii) a bromine-containing monoester that has nine or more carbon atoms and R1 contains an aromatic-alkyl moiety;
- B) a bromine-containing diester represented by the formula
- wherein Rb contains a quaternary carbon atom or an internal alkene moiety, wherein the oxygen atoms adjacent to Rb are not bound to a quaternary carbon atom or an alkenyl carbon atom, and Ra and Rc are each, independently, a hydrocarbyl group or a bromine-containing hydrocarbyl group, wherein the bromine-containing diester is
- i) a bromine-containing diester that has nine or more carbon atoms and Rb contains a quaternary carbon atom,
- ii) a bromine-containing diester that has eight or more carbon atoms and Rb contains an internal alkene moiety,
- C) a bromine-containing triester which has at least seven carbon atoms and is represented by the formula
- wherein Rd, Re, Rf, and Rg are each, independently, a hydrocarbyl group or a bromine-containing hydrocarbyl group, and at least one of Rd, Re, Rf, and Rg is a bromine-containing hydrocarbyl group;
- and
- D) any two or more of the foregoing.
10 more elements
Each of the following molecules separately, as a new composition of matter:
- 3-bromo-2,2-bis(bromomethyl)propyl propionate;
- 3-bromo-2,2-bis(bromomethyl)propyl butyrate;
- 3-bromo-2,2-bis(bromomethyl)propyl 2-methylpropanoate;
- 3-bromo-2,2-bis(bromomethyl)propyl pentanoate;
- 3-bromo-2,2-bis(bromomethyl)propyl isovalerate;
- 3-bromo-2,2-bis(bromomethyl)propyl hexanoate;
- (3,5-dibromophenyl)methyl propionate;
- (3,5-dibromophenyl)methyl butyrate;
- (3,5-dibromophenyl)methyl 2-methylpropanoate;
- (3,5-dibromophenyl)methyl pentanoate;
- 2,2-bis(bromomethyl) 1,3-propanediol-1,3-dipropionate;
- 2,2-bis(bromomethyl) 1,3-propanediol-1,3-di(2-methylpropanoate);
- 2,2-bis(bromomethyl) 1,3-propanediol-1,3-dihexanoate;
- 2,2-bis(bromomethyl) 1,3-propanediol-1,3-bis-(bromoacetate);
- (2E)-2,3-dibromobut-2-ene-1,4-diyl bis(propanoate);
- (2E)-2,3-dibromobut-2-ene-1,4-diyl bis(2-methylpropanoate);
- (2Z)-but-2-ene-1,4-diyl bis(bromoacetate);
- 3-bromo-2-{[(bromoacetyl)oxy]methyl}-2-(bromomethyl)propyl hexanoate;
- 3-bromo-2-{[acetyloxy]methyl}-2-(bromomethyl)propyl propionate;
- 3-bromo-2-{[acetyloxy]methyl}-2-(bromomethyl)propyl 2-methylpropanoate;
- 3-bromo-2-{[(propionyl)oxy]methyl}-2-(bromomethyl)propyl 2-methylpropanoate;
- 3-bromo-2-{[(propionyl)oxy]methyl}-2-(bromomethyl)propyl butyrate;
- 3-bromo-2-[(butyryloxy)methyl]-2-(bromomethyl)propyl 2-methylpropanoate;
- (2E)-2,3-dibromo-4-[(propionyl)oxy]but-2-en-1-yl butanoate;
- (2E)-2,3-dibromo-4-[(propionyl)oxy]but-2-en-1-yl 2-methylpropanoate;
- (2E)-2,3-dibromo-4-[(bromoacetyl)oxy]but-2-en-1-yl hexanoate;
- (2E)-2,3-dibromo-4-[(bromoacetyl)oxy]but-2-en-1-yl 2-methylpropanoate;
- (2E)-2,3-dibromo-4-[(2-methylpropionyl)oxy]but-2-en-1-yl 3-methylbutanoate, (2E)-2,3-dibromo-4-[(propionyl)oxy]but-2-ene-1-yl lineolate;
- (2E)-2,3-dibromo-4-[(propionyl)oxy]but-2-en-1-yl acetate;
- (2E)-2,3-dibromo-4-[(2-methylpropionyl)oxy]but-2-en-1-yl acetate;
- (2E)-2,3-dibromo-4-[(2-methylpropionyl)oxy]but-2-en-1-yl butyrate;
- (2Z)-1-[(propionyl)oxy]but-2-ene-4-yl acetate;
- (2Z)-1-[(2-methylpropionyl)oxy]but-2-ene-4-yl acetate;
- propane-1,2,3-triyl bis(bromoacetate)(hexanoate);
- propane-1,2,3-triyl (bromoacetate)bis(hexanoate),
- 2,2-bis(bromomethyl)propane-1,3-diyl di (bromoacetate);
- 2,2-bis(bromomethyl)propane-1,3-diyl dibutanoate;
- (2E)-2,3-dibromobut-2-ene-1,4-diyl bis(bromoacetate);
- (2E)-2,3-dibromobut-2-ene-1,4-diyl dibutanoate;
- (2E)-2,3-dibromobut-2-ene-1,4-diyl bis(3-methylbutanoate);
- (2E)-2,3-dibromobut-2-ene-1,4-diyl dihexanoate;
- (2E)-2,3-dibromobut-2-ene-1,4-diyl dilineolate;
- (2Z)-but-2-ene-1,4-diyl diacetate;
- (2Z)-but-2-ene-1,4-diyl dipropionate;
- (2Z)-but-2-ene-1,4-diyl di(2-methylpropionate);
- propane-1,2,3-triyl tris (bromoacetate).
43 more elements
Each of the following mixtures of molecules, as a new composition of matter:
- a) 2,2-bis(bromomethyl)propane-1,3-diyl di (bromoacetate), 3-bromo-2-{[(bromoacetyl)oxy]methyl}-2-(bromomethyl)propyl hexanoate, and 2,2-bis(bromomethyl)propane-1,3-diyl dihexanoate;
- b) (2E)-2,3-dibromobut-2-ene-1,4-diyl dipropanoate, (2E)-2,3-dibromobut-2-ene-1,4-diyl dibutanoate, and (2E)-2,3-dibromo-4-[(propionyl)oxy]but-2-en-1-yl butanoate;
- c) (2E)-2,3-dibromobut-2-ene-1,4-diyl dipropanoate, (2E)-2,3-dibromobut-2-ene-1,4-diyl bis(2-methylpropanoate), and (2E)-2,3-dibromo-4-[(propionyl)oxy]but-2-en-1-yl 2-methylpropanoate;
- d) (2E)-2,3-dibromobut-2-ene-1,4-diyl bis(bromoacetate), (2E)-2,3-dibromo-4-[(bromoacetyl)oxy]but-2-en-1-yl hexanoate, and (2E)-2,3-dibromobut-2-ene-1,4-diyl dihexanoate;
- e) (2E)-2,3-dibromobut-2-ene-1,4-diyl bis(2-methylpropanoate), (2E)-2,3-dibromobut-2-ene-1,4-diyl bis(bromoacetate), and (2E)-2,3-dibromo-4-[(bromoacetyl)oxy]but-2-en-1-yl 2-methylpropanoate;
- f) (2E)-2,3-dibromobut-2-ene-1,4-diyl bis(2-methylpropanoate), (2E)-2,3-dibromobut-2-ene-1,4-diyl bis(3-methylbutanoate), and (2E)-2,3-dibromo-4-[(2-methylpropionyl)oxy]but-2-en-1-yl 3-methylbutanoate;
- g) (2E)-2,3-dibromobut-2-ene-1,4-diyl dipropionate, (2E)-2,3-dibromobut-2-ene-1,4-diyl dilineolate, and (2E)-2,3-dibromo-4-[(propionyl)oxy]but-2-en-1-yl lineolate;
- h) (2E)-2,3-dibromobut-2-ene-1,4-diyl diacetate, (2E)-2,3-dibromobut-2-ene-1,4-diyl propionate, (2E)-2,3-dibromo-4-[(propionyl)oxy]but-2-en-1-yl acetate, (2Z)-2,3-dibromobut-2-ene-1,4-diyl diacetate, (2Z)-2,3-dibromobut-2-ene-1,4-diyl dipropionate, and (2Z)-2,3-dibromo-4-[(propionyl)oxy]but-2-en-1-yl acetate;
- i) (2E)-2,3-dibromobut-2-ene-1,4-diyl diacetate, (2E)-2,3-dibromobut-2-ene-1,4-diyl di(2-methylpropanoate), (2E)-2,3-dibromo-4-[2-methylpropionyl)oxy]but-2-en-1-yl acetate, (2Z)-3-but-2-ene-1,4-diyl diacetate, (2Z)-but-2-ene-1,4-diyl dipropionate, and (2Z)-but-2-ene-4-[(propionyl)oxy]but-2-en-1-yl acetate;
- j) (2E)-2,3-dibromobut-2-ene-1,4-diyl dibutanoate and 2,2-bis(bromomethyl)propane-1,3-diyl dibutanoate;
- k) 2,2-bis(bromomethyl)propane-1,3-diyl diacetate, 2,2-bis(bromomethyl)propane-1,3-diyl dipropionate, 2,2-bis(bromomethyl)propane-1,3-diyl di(2-methylpropanoate), 3-bromo-2-{[acetyloxy]methyl}-2-(bromomethyl)propyl propionate, 3-bromo-2-{[acetyloxy]methyl}-2-(bromomethyl)propyl 2-methylpropanoate, 3-bromo-2-{[(propionyl)oxy]methyl}-2-(bromomethyl)propyl 2-methylpropanoate, (2E)-2,3-dibromobut-2-ene-1,4-diyl diacetate, (2E)-2,3-dibromobut-2-ene-1,4-diyl dipropionate, (2E)-2,3-dibromobut-2-ene-1,4-diyl di(2-methylpropanoate), (2E)-2,3-dibromo-4-[(2-methylpropionyl)oxy]but-2-en-1-yl acetate, (2E)-2,3-dibromo-4-[(2-methylpropionyl)oxy]but-2-en-1-yl propionate, and (2E)-2,3-dibromo-4-[(propionyl)oxy]but-2-en-1-yl acetate;
- l) 2,2-bis(bromomethyl)propane-1,3-diyl dipropionate, 2,2-bis(bromomethyl)propane-1,3-diyl dibutyrate, 2,2-bis(bromomethyl)propane-1,3-diyl di(2-methylpropanoate), 3-bromo-2-{[(propionyl)oxy]methyl}-2-(bromomethyl)propyl butyrate, 3-bromo-2-[((propionyl)oxy)methyl]-2-(bromomethyl)propyl 2-methylpropanoate, 3-bromo-2-[(butyryloxy)methyl]-2-(bromomethyl)propyl 2-methylpropanoate, (2E)-2,3-dibromobut-2-ene-1,4-diyl dipropionate, (2E)-2,3-dibromobut-2-ene-1,4-diyl dibutyrate, (2E)-2,3-dibromobut-2-ene-1,4-diyl di(2-methylpropanoate), (2E)-2,3-dibromo-4-[(2-methylpropionyl)oxy]but-2-en-1-yl propionate, (2E)-2,3-dibromo-4-[(2-methylpropionyl)oxy]but-2-en-1-yl butyrate, and (2E)-2,3-dibromo-4-[(butyryl)oxy]but-2-en-1-yl propionate;
- m) propane-1,2,3-triyl tris (bromoacetate), propane-1,2,3-triyl tris (hexanoate), propane-1,2,3-triyl bis(bromoacetate)(hexanoate), and propane-1,2,3-triyl (bromoacetate)bis(hexanoate).
10 more elements
Dependencies are inferred from the claim text.