WO2024112545A1 - Alourdissants liquides pour fluides à base d'huile - Google Patents
Alourdissants liquides pour fluides à base d'huile Download PDFInfo
- Publication number
- WO2024112545A1 WO2024112545A1 PCT/US2023/079903 US2023079903W WO2024112545A1 WO 2024112545 A1 WO2024112545 A1 WO 2024112545A1 US 2023079903 W US2023079903 W US 2023079903W WO 2024112545 A1 WO2024112545 A1 WO 2024112545A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- fluid
- bromine
- weighting agent
- liquid weighting
- liquid
- Prior art date
Links
- 239000007788 liquid Substances 0.000 title claims abstract description 99
- 239000012530 fluid Substances 0.000 title claims description 112
- 239000000203 mixture Substances 0.000 claims abstract description 35
- 239000003795 chemical substances by application Substances 0.000 claims description 100
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 50
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 45
- 229910052794 bromium Inorganic materials 0.000 claims description 45
- 229920006395 saturated elastomer Chemical group 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
- 239000001301 oxygen Substances 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000001246 bromo group Chemical group Br* 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000004122 cyclic group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 239000000654 additive Substances 0.000 claims description 14
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 150000005690 diesters Chemical class 0.000 claims description 11
- 150000005691 triesters Chemical class 0.000 claims description 11
- 238000005553 drilling Methods 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 150000001336 alkenes Chemical group 0.000 claims description 5
- NGPBQLWHTVOGBS-UHFFFAOYSA-N BrCC1(COC(OC1)CC)CBr Chemical compound BrCC1(COC(OC1)CC)CBr NGPBQLWHTVOGBS-UHFFFAOYSA-N 0.000 claims description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical group CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 230000002459 sustained effect Effects 0.000 claims description 4
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 claims description 3
- 239000003921 oil Substances 0.000 description 35
- 238000012360 testing method Methods 0.000 description 18
- -1 n- propyl Chemical group 0.000 description 14
- 239000000306 component Substances 0.000 description 13
- 239000004615 ingredient Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- 238000002156 mixing Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000011435 rock Substances 0.000 description 4
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 238000005098 hot rolling Methods 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012956 testing procedure Methods 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 2
- OLSFTXUJEVKHAU-UHFFFAOYSA-N 5-acetyloxypent-3-enyl acetate Chemical compound CC(=O)OCCC=CCOC(C)=O OLSFTXUJEVKHAU-UHFFFAOYSA-N 0.000 description 2
- IQHMXMTVSLOWEX-UHFFFAOYSA-N CCOCCOC(C=CC(Br)=C1)=C1Br Chemical compound CCOCCOC(C=CC(Br)=C1)=C1Br IQHMXMTVSLOWEX-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000000844 transformation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OIXUJRCCNNHWFI-UHFFFAOYSA-N 1,2-dioxane Chemical compound C1CCOOC1 OIXUJRCCNNHWFI-UHFFFAOYSA-N 0.000 description 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CHUGKEQJSLOLHL-UHFFFAOYSA-N 2,2-Bis(bromomethyl)propane-1,3-diol Chemical compound OCC(CO)(CBr)CBr CHUGKEQJSLOLHL-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 description 1
- MPSNTHJGVYSBOS-UHFFFAOYSA-N CCOCCOC(C(Br)=CC=C1)=C1Br Chemical compound CCOCCOC(C(Br)=CC=C1)=C1Br MPSNTHJGVYSBOS-UHFFFAOYSA-N 0.000 description 1
- UWOWKJXUDQKASH-UHFFFAOYSA-N CCOCCOC(C=C(C(Br)=C1)OC)=C1Br Chemical compound CCOCCOC(C=C(C(Br)=C1)OC)=C1Br UWOWKJXUDQKASH-UHFFFAOYSA-N 0.000 description 1
- CYMXYQKFRXRYAG-UHFFFAOYSA-N CCOCCOC(C=C(C(Br)=C1)OCC)=C1Br Chemical compound CCOCCOC(C=C(C(Br)=C1)OCC)=C1Br CYMXYQKFRXRYAG-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- IRUCBBFNLDIMIK-UHFFFAOYSA-N oct-4-ene Chemical compound CCCC=CCCC IRUCBBFNLDIMIK-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/02—Well-drilling compositions
- C09K8/03—Specific additives for general use in well-drilling compositions
- C09K8/035—Organic additives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/02—Well-drilling compositions
- C09K8/32—Non-aqueous well-drilling compositions, e.g. oil-based
Definitions
- This invention relates to liquid weighting agents for oilfield applications.
- the well fluids need to have a relatively high density, so one or more ingredients are added to the well fluid to increase the density of the well fluid.
- Brines are typically used to increase the density of aqueous well fluids, but some well fluids are oil-based.
- solid weighting agents are often used to increase the well fluid density, but solid weighting agents often block pores and decrease production from the formation.
- Liquid weighting agents are an alternative to solid weighting agents for oil-based well fluids, but may not be miscible with the oil-based fluid, may form emulsions with the oil-based well fluid, and/or cause solids formation. There is a need for liquid weighting agents that do not form emulsions and/or cause precipitation.
- This invention provides liquid weighting agents that increase the density of oilbased well fluids, and can provide high density fluids.
- the liquid weighting agent is made part of the oil-based well fluid.
- the liquid weighting agents of the invention can increase the densities of an oil-based well fluid to about 14.5 pounds per gallon (1.74 kg/L) or more.
- liquid weighting agents permit use of increased drill speeds.
- Another advantage of these liquid weighting agents is a greater amount of oil produced from the formation.
- Still another advantage of the liquid weighting agents of the present invention is that they do not significantly alter the fluid loss properties of formulations in which they are present.
- liquid weighting agents of the invention are a minimal effect on the viscosity of the fluids to which they are introduced or combined; in some instances, liquid weighting agents of the invention reduce the viscosity of the fluids to which they are introduced or combined, so a change of equipment to larger pumps is not required.
- Another advantage provided by the liquid weighting agents of the invention is that they can be a component of optically clear fluids.
- An embodiment of this invention is a liquid weighting agent containing two or more bromine atoms and having a bromine content of about 35 wt% or more.
- the liquid weighting agent is selected from a) a bromine-containing saturated cyclic diether comprising two or more bromine atoms, and a saturated ring comprising two oxygen atoms and four or more carbon atoms, the saturated ring having one or more hydrocarbyl substituents, each bound to a carbon atom of the saturated ring, wherein each bromine atom is bound to a hydrocarbyl substituent in a position on the hydrocarbyl substituent that does not have beta hydrogen atoms; b) a bromine-containing aromatic diether comprising one phenyl ring having two or three bromine atoms bound to the phenyl ring and at least one oxygen-containing group bound to the phenyl ring via an oxygen atom, with the proviso that when there is only one oxygen-containing group, the oxygen-containing group is an alkoxyether group; and c) any two or more of the foregoing.
- Another embodiment of this invention is an oil-based well fluid comprising a liquid weighting agent selected from the bromine-containing ethers described above.
- aromatic carbon atom refers to a carbon atom that is part of an aromatic ring.
- liquid weighting agents of this invention are usable as oil-miscible weighting agents (OMWA).
- OMWA oil-miscible weighting agents
- the term "miscible” means that emulsions and/or separate phases are not observed in a 50:50 weight mixture of one or more of the liquid weighting agents of this invention (total of 50 wt%) and an oil (50 wt%) after the mixture has been kept at 0°C for one week.
- the term “partially miscible” means that emulsions and/or separate phases are not observed in a 50:50 weight mixture of one or more of the liquid weighting agents of this invention (total of 50 wt%) and an oil (50 wt%) after the mixture has been kept at room temperature for one week.
- the liquid weighting agents of the present invention are generally miscible with oil-based well fluids.
- the liquid weighting agents are often in a mixture with an oil.
- Oils with which the liquid weighting agents are optionally mixed are oils which usually have a viscosity of about 7 cP or less, and a density typically about 0.7 g/mL to about 0.9 g/mL.
- the amount of liquid weighting agent in the oil can be about 0.1 wt% to 100 wt%; when more than one liquid weighting agent is used, the amount refers to the total amount of liquid weighting agents. When there is 100 wt% liquid weighting agent of the invention, no other substance is present with the liquid weighting agent.
- liquid weighting agent in the oil depend on the desired density, and there is typically about 0. 1 wt% to 100 wt% liquid weighting agent in a mixture with an oil, more often about 0.1 to about 99.9 wt%, preferably about 2 wt% to about 99.9 wt% liquid weighting agent in a mixture with an oil.
- the mixture of oil and the liquid weighting agent(s) usually have a viscosity of about 10 cP or less, and a density typically about 0.7 g/mL to about 1.8 g/mL.
- the liquid weighting agents of this invention share some overall characteristics.
- these liquid weighting agents there are two or more bromine atoms in the molecule, and a bromine content of about 35 wt% or more.
- the bromine content in the liquid weighting agent is preferably about 35 wt% to about 70 wt%, more preferably about 40 wt% to about 65 wt%, relative to the total weight of the liquid weighting agent.
- the liquid weighting agent is a bromine-containing saturated cyclic diether comprising two or more bromine atoms, and a saturated ring comprising two oxygen atoms and three or more carbon atoms, the saturated ring having one or more hydrocarbyl substituents, each bound to a carbon atom of the saturated ring, wherein each bromine atom is bound to a hydrocarbyl substituent.
- the bromine- containing saturated cyclic diether has four or more carbon atoms, preferably four to about fifteen carbon atoms, more preferably four to about twelve carbon atoms, still more preferably five to about ten carbon atoms, in the molecule.
- the saturated ring of the cyclic diether can be a five-membered, six-membered, seven-membered ring, or a larger ring; five-membered and six-membered rings are preferred, and the saturated ring is often a 1,2-dioxololane, 1,3-dioxololane, 1,4- dioxololane, 1,2-dioxane, 1,3-dioxane, or 1,4-dioxane ring; preferred is a 1.3 dioxane ring.
- hydrocarbyl substituents on the saturated ring there are one or more hydrocarbyl substituents on the saturated ring; when there is more than one hydrocarbyl substituent, they can be on the same or different carbon atoms of the saturated ring.
- the saturated ring has one to about three hydrocarbyl substituents.
- the hydrocarbyl substituents on the saturated ring can be saturated or unsaturated, straight chain, branched, or aromatic; preferably the hydrocarbyl portions are saturated straight chains.
- Suitable hydrocarbyl portions include methyl, ethyl, ethenyl, n- propyl, 2-propyl, n-butyl, pentyl, cyclopentyl, hexyl, cyclohexyl, and phenyl; methyl and phenyl are preferred.
- the bromine atoms are located on the hydrocarbyl substituent(s) of the saturated ring.
- the bromine atoms can be on the same or different hydrocarbyl substituent; preferably, the bromine atoms are on different hydrocarbyl substituents.
- the bromine atoms are in positions on the hydrocarbyl substituent which do not have beta hydrogen atoms.
- bromine-containing saturated cyclic diethers of the invention typically have a bromine content of about 40 wt% or more, preferably about 45 wt% or more, and often have densities of about 1.50 g/mL or more.
- Suitable cyclic diethers in the practice of this invention include 4,4-bis(2- bromoethyl)- 1 ,2-dioxolane, 4,5 -bis(3 -bromo-n-propyl)- 1 ,3 -dioxolane, 5,5- bis(bromomethyl)-l,2-dioxane, 5,5-bis(bromomethyl)-2-ethyl-l,3-dioxane, and 2-methyl- 5-(l,2-dibromoethyl)-l,4-dioxane.
- Preferred cyclic diethers include 5,5-bis(bromomethyl)- 1,2-dioxane and 5,5-bis(bromomethyl)-2-ethyl-l,3-dioxane, especially 5,5- bis(bromomethyl)-2-ethyl- 1 ,3-dioxane.
- the liquid weighting agent is a bromine-containing aromatic diether comprising one phenyl ring having two or three bromine atoms bound to the phenyl ring and at least one oxygen-containing group bound to the phenyl ring via an oxygen atom, with the proviso that when there is only one oxygen-containing group, the oxygencontaining group is an alkoxyether group.
- the bromine atoms are preferably ortho or para relative to each other.
- the bromine-containing aromatic diethers typically have a bromine content of about 35 wt% or more, preferably about 40 wt% or more, more preferably about 45 wt% or more.
- the alkoxyether groups When there is only one oxygen-containing group in the bromine-containing aromatic diether, the hydrocarbyl portions of the groups are saturated.
- the alkoxyether groups have two to about eight carbon atoms, preferably three to about six carbon atoms, more preferably two to about three oxygen atoms. More preferably, the alkoxyether group containing two or more oxygen atoms has an ethylene unit between each pair of oxygen atoms, and the terminal group is preferably methyl or ethyl.
- Preferred alkoxyether groups include 2-methoxyethoxy and 2-ethoxyethoxy.
- At least one bromine atom is preferably adjacent ortho) to the group containing two or more oxygen atoms; in some preferred embodiments, two bromine atoms are adjacent to the alkoxyether group.
- one of the oxygen-containing groups is a hydrocarbyloxy group. More preferably, the hydrocarbyloxy group is an alkoxy group having one to about four carbon atoms, preferably one or two carbon atoms. Preferred hydrocarbyloxy groups include methoxy and ethoxy.
- one of the oxygen-containing groups is an alkoxyether group and the other oxygen- containing group is a hydrocarbyloxy group; preferences for alkoxyether groups and hydrocarbyloxy groups are as described above. More preferably, there are two bromine atoms on the phenyl ring when there are two oxygen-containing groups on the phenyl ring of the bromine-containing aromatic diether.
- Suitable bromine-containing aromatic diethers in the practice of this invention include l,3-dibromo-4-(2-ethoxy)ethoxybenzene, l,2-dibromo-4-butoxy-5-ethoxybenzene 2,4- dibromo-5 -methoxy- 1 -[(2-ethoxy)ethoxy]benzene, 2, 4-dibromo-5 -ethoxy- 1-[(2- ethoxy)ethoxy]benzene, 2,4-dibromo- 1 -[(2-ethoxy)ethoxy]benzene, 2,6-dibromo- 1 - [(2- ethoxy)ethoxy]benzene; preferred bromine-containing aromatic diethers include 1,3- dibromo-4-(2-ethoxy)ethoxybenzene, and 1 ,2-dibromo-4-butoxy-5-ethoxybenzene.
- liquid weighting agents of the invention have enough high- temperature thermal stability that they can be used in HPHT (high pressure, high temperature) conditions.
- HPHT conditions are usually defined as a temperature greater than about 250°F (121 °C) and a pore pressure greater than about 0.8 psi/ft (15.3 Ib/gal).
- the liquid weighting agents of the invention when used in offshore applications, need low-temperature thermal stability because temperatures at the sea floor can be around 5°C.
- Optional additives can include, for example, other weighting agents, corrosion inhibitors, lubricants, pH control additives, surfactants, and/or solvents.
- Preferred types of optional additives in the practice of this invention are unsaturated diesters and saturated triesters that do not contain bromine.
- the additive is an unsaturated diester
- the unsaturated diester has at least eight carbon atoms and is represented by the formula where R a and R c are hydrocarbyl groups, and R b is an alkene-containing moiety.
- R a and R c can be straight chain, branched, cyclic, or aromatic; preferably the hydrocarbyl group is a straight chain.
- Suitable hydrocarbyl groups include methyl, ethyl, n-propyl, 2-propyl, n- butyl, pentyl, cyclopentyl, hexyl, and cyclohexyl; ethyl and n-propyl are preferred.
- R b preferably has four to about eight carbon atoms, more preferably four to about six carbon atoms; suitable alkene-containing moieties include 2-butene, 2-pentene, 2-hexene, 3- hexene, 2-octene 3-octene, and 4-octene; preferred alkene-containing moieties include 2- butuene.
- the saturated triester has at least seven carbon atoms and is represented by the formula where R d , R c , R f , and R g are hydrocarbyl groups.
- R d , R f , and R g can be straight chain, branched, or cyclic; preferably the hydrocarbyl group is a straight chain.
- Suitable hydrocarbyl groups include methyl, ethyl, n-propyl, 2-propyl, n-butyl, pentyl, cyclopentyl, hexyl, cyclohexyl, and phenyl; ethyl and n-propyl are preferred.
- R c can be branched or cyclic, or aromatic; preferably R c is a saturated branched chain.
- Suitable hydrocarbyl groups include propyl, butyl, 2-pentyl, 3-pentyl, cyclopentyl, 2-hexyl, 3, -hexyl, and cyclohexyl; 2- propyl is a preferred group.
- Suitable unsaturated diesters that do not contain bromine include but-2-ene-l,4- diyl diacetate, but-2-ene- 1 ,4-diyl bis(propanoate), but-2-ene- 1 ,4-diyl bis(butyrate), but-2- ene-l,4-diyl bis(pentanoate), pent-2-ene- 1,5 -diyl diacetate, pent-3 -ene- 1,5 -diyl diacetate, pent-3-ene- 1 ,5-diyl bis(propanoate); preferred is but-2-ene- 1 ,4-diyl bis(butyrate).
- Suitable saturated triesters that do not contain bromine include propane- 1,2, 3 -triyl triacetate, propane- 1, 2, 3-triyl propanoate, propane- 1,2, 3 -triyl tributyrate; preferred is propane- 1,2,3 - triyl tributyrate.
- propane- 1,2,3 - triyl tributyrate propane- 1,2,3 - triyl tributyrate.
- Processes for forming mixtures of a liquid weighting agent and an oil comprise combining the oil and the liquid weighting agent in any order.
- an oil and the liquid weighting agent(s) can be added sequentially, or they can be introduced to a vessel or location simultaneously.
- any optional additives that are included can be combined with the liquid weighting agents in any convenient manner.
- optional additives can be added before, during, and/or after formation of the mixture of an oil and the liquid weighting agent.
- a mixture of an oil and one or more liquid weighting agents of the invention is solids-free.
- liquid weighting agents of the invention can be part of a mixture containing one or more solids, for example a solid weighting agent such as barite, if desired.
- a liquid weighting agent of the invention will reduce the amount of solid weighting agent needed to achieve the desired density.
- Calcium carbonate is often present as a suspension in a well fluid.
- the calcium carbonate often forms a filter cake that prevents the drilling fluid from entering the formation.
- an acid treatment can be used to remove the calcium carbonate filter cake.
- One or more liquid weighting agents of the invention can be combined with an oilbased well fluid.
- the oil-based well fluid can be a drilling fluid; completion fluids fluids including but not limited to a packer fluid, a screen running fluid, or a carrier fluid; a (reservoir) drill-in fluid; a tractor fluid; a camera fluid; or workover fluids fluids including but not limited to a coiled tubing drilling fluid.
- the liquid weighting agents of the invention can be combined with the well fluid alone or in admixture with one or more other additives and/or in a mixture with an oil.
- the liquid weighting agents of the invention can be used as secondary fluids ("kill fluids") to minimize or relieve sustained casing pressure in a wellbore annulus.
- active fluid refers to the first fluid, which is present in the wellbore annulus before the second fluid is introduced.
- the second fluid can be introduced at the wellhead or below the surface of the annular fluid; subsurface introduction of the kill fluid is generally preferred.
- immiscibility refers to the non-mixing or substantial non-mixing of the liquid weighting agents and the (aqueous) annular fluid. See in this connection International Publication WO 2015/100004.
- the liquid weighting agents of this invention can be used as additives for hydraulic fluids.
- the liquid weighting agent of the invention is about 35 wt% or more relative to the total weight of the hydraulic fluid and the liquid weighting agent of the invention.
- bromine content there is about 20 wt% to about 70 wt% bromine relative to the total weight of the hydraulic fluid and the liquid weighting agent of the invention.
- Other additives such as antioxidants, lubricity agents, and metal deactivators, may also be present in the hydraulic fluid.
- reaction mixture was washed with saturated sodium bicarbonate (4x300 mL) and then with water (400 mL). The phases were allowed to separate, and the separated organic layer was dried over MgSCL. After filtration to remove the solids, the toluene was removed from the organic layer on rotavap under vacuum ( ⁇ 60 torr), and 723 grams of the product were obtained as a colorless liquid with a density of 1.64 g/mL. A 50:50 wt/wt mixture of this product with an oil had not phase separated after one week at -18°C.
- Admixture preparation To a 600 mL beaker were added a synthetic oil fluid (Saraline® 185V), and a liquid weighting agent of the invention. An overhead lab mixer (Silverson, model L5M-A) is lowered into the liquid and slowly turned up to 4000 rpm. Various ingredients were then added sequentially, stirring for a period of time after each addition. The mixture was transferred to a stand mixer (Hamilton Beach), usually before the addition of calcium carbonate.
- Saraline® 185V synthetic oil fluid
- An overhead lab mixer Simverson, model L5M-A
- Various ingredients were then added sequentially, stirring for a period of time after each addition.
- the mixture was transferred to a stand mixer (Hamilton Beach), usually before the addition of calcium carbonate.
- Admixture testing The American Petroleum Institute Recommended Practice 13B-2 (API RP 13B-2) testing procedures for field testing oil-based drilling fluids were followed to obtain properties of the mixture formed as described above. The sample was then hot-rolled overnight to simulate heat aging of the sample in actual use. The properties of the sample were then tested again using the same testing procedures.
- Fluid loss testing The API Fluid Loss Experiment was conducted at approximately 250°F (121°C). The sample was heated to ⁇ 250°F (121°C) over 1.5 hours, and was passed through a 10-micron filter disk (Fann®) in a filter press (Model 387, Fann Instrument Company) at ⁇ 250°F for 30 minutes with a 500 psi (3.45 MPa) pressure differential. The API fluid loss volume for fluid loss is double the total volume measured due to the surface area of the filter disk. Results of the Fluid Loss Experiment are summarized in Table 3 below. The filter cake thickness was measured.
- HPHT fluid loss procedure was as follows:
- a synthetic disk or rock core was placed into the testing cell.
- the fluid to be tested was poured into the testing cell (typically 350 to 500 mL of fluid).
- the testing cell was placed in a heating jacket and heated to the testing temperature (300°F for most fluids).
- valves were closed, and the heating jacket was turned off.
- the testing cell was allowed to cool before removing the remaining fluid.
- the synthetic disk or rock core was removed and examined to observe the filter cake (solids left by the fluid as it traveled into or through the disk or rock core).
- 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 saturated cyclic diether comprising two or more bromine atoms, and a saturated ring comprising two oxygen atoms and four or more carbon atoms, the saturated ring having one or more hydrocarbyl substituents, each bound to a carbon atom of the saturated ring, wherein each bromine atom is bound to a hydrocarbyl substituent in a position on the hydrocarbyl substituent that does not have beta hydrogen atoms; b) a bromine-containing aromatic diether comprising one phenyl ring having two or three bromine atoms bound to the phenyl ring and at least one oxygen-containing group bound to the phenyl ring via an oxygen atom, with the proviso that when there is only one oxygen-containing group, the oxygen-containing group is an alkoxyether group;
- a liquid weighting agent as in any of A)-H) which is in a mixture with an oil, wherein there is about 0. 1 to about 99.9 wt% liquid weighting agent in the mixture with the oil; or in combination with a hydraulic fluid.
- An oil-based well fluid comprising a liquid weighting agent of any of A)-H), optionally wherein the well fluid is a drilling fluid, a completion fluid, a drill-in fluid, a tractor fluid, a camera fluid, or a workover fluid.
- K) A method of treating a wellbore comprising introducing into the wellbore a fluid comprising a liquid weighting agent as in any of A)-H), optionally wherein the fluid is a drilling fluid, a completion fluid, a drill-in fluid, a tractor fluid, a camera fluid, or a workover fluid.
- the fluid is a drilling fluid, a completion fluid, a drill-in fluid, a tractor fluid, a camera fluid, or a workover fluid.
- the invention may comprise, consist, or consist essentially of the materials and/or procedures recited herein.
- the term "about" modifying the quantity of an ingredient in the compositions of the invention or employed in the methods of the invention refers to variation in the numerical quantity that can occur, for example, through typical measuring and liquid handling procedures used for making concentrates or use solutions in the real world; through inadvertent error in these procedures; through differences in the manufacture, source, or purity of the ingredients employed to make the compositions or carry out the methods; and the like.
- the term about also encompasses amounts that differ due to different equilibrium conditions for a composition resulting from a particular initial mixture. Whether or not modified by the term "about”, the claims include equivalents to the quantities.
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Abstract
La présente invention concerne des compositions qui peuvent être utilisées en tant qu'alourdissants liquides.
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US202263427150P | 2022-11-22 | 2022-11-22 | |
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US202363537599P | 2023-09-11 | 2023-09-11 | |
US63/537,599 | 2023-09-11 |
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Citations (3)
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WO2015100004A1 (fr) | 2013-12-23 | 2015-07-02 | Albemarle Corporation | Régulation de pression soutenue sur un tubage dans des espaces annulaires de puits de forage |
WO2021101922A1 (fr) * | 2019-11-18 | 2021-05-27 | Albemarle Corporation | Agents ignifuges pour électrolytes de batterie |
WO2022212637A1 (fr) * | 2021-04-01 | 2022-10-06 | Albemarle Corporation | Agents ignifuges pour électrolytes de batterie |
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- 2023-11-15 WO PCT/US2023/079903 patent/WO2024112545A1/fr unknown
Patent Citations (3)
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WO2015100004A1 (fr) | 2013-12-23 | 2015-07-02 | Albemarle Corporation | Régulation de pression soutenue sur un tubage dans des espaces annulaires de puits de forage |
WO2021101922A1 (fr) * | 2019-11-18 | 2021-05-27 | Albemarle Corporation | Agents ignifuges pour électrolytes de batterie |
WO2022212637A1 (fr) * | 2021-04-01 | 2022-10-06 | Albemarle Corporation | Agents ignifuges pour électrolytes de batterie |
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