WO1995032265A1 - Temperature stable synthetic oil - Google Patents
Temperature stable synthetic oil Download PDFInfo
- Publication number
- WO1995032265A1 WO1995032265A1 PCT/GB1995/001182 GB9501182W WO9532265A1 WO 1995032265 A1 WO1995032265 A1 WO 1995032265A1 GB 9501182 W GB9501182 W GB 9501182W WO 9532265 A1 WO9532265 A1 WO 9532265A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- amide
- composition according
- ester
- polyamide
- polyester
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims abstract description 34
- 150000001408 amides Chemical class 0.000 claims abstract description 31
- 150000002148 esters Chemical class 0.000 claims abstract description 26
- 239000004952 Polyamide Substances 0.000 claims abstract description 22
- 229920002647 polyamide Polymers 0.000 claims abstract description 22
- 229920000728 polyester Polymers 0.000 claims abstract description 19
- 230000007062 hydrolysis Effects 0.000 claims abstract description 13
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 13
- 239000000314 lubricant Substances 0.000 claims abstract description 8
- 239000003921 oil Substances 0.000 claims description 23
- 150000001412 amines Chemical class 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 17
- 150000001721 carbon Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 238000006467 substitution reaction Methods 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 238000005553 drilling Methods 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 150000003333 secondary alcohols Chemical class 0.000 claims description 3
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000005265 dialkylamine group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229920006149 polyester-amide block copolymer Polymers 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 description 6
- 230000003301 hydrolyzing effect Effects 0.000 description 5
- 238000013112 stability test Methods 0.000 description 4
- -1 ester alcohols Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- WRYLYDPHFGVWKC-UHFFFAOYSA-N 4-terpineol Chemical compound CC(C)C1(O)CCC(C)=CC1 WRYLYDPHFGVWKC-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- OVKDFILSBMEKLT-UHFFFAOYSA-N alpha-Terpineol Natural products CC(=C)C1(O)CCC(C)=CC1 OVKDFILSBMEKLT-UHFFFAOYSA-N 0.000 description 2
- 229940088601 alpha-terpineol Drugs 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- PFURGBBHAOXLIO-WDSKDSINSA-N cyclohexane-1,2-diol Chemical compound O[C@H]1CCCC[C@@H]1O PFURGBBHAOXLIO-WDSKDSINSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical compound CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 description 1
- ZWNMRZQYWRLGMM-UHFFFAOYSA-N 2,5-dimethylhexane-2,5-diol Chemical compound CC(C)(O)CCC(C)(C)O ZWNMRZQYWRLGMM-UHFFFAOYSA-N 0.000 description 1
- WRYLYDPHFGVWKC-SNVBAGLBSA-N 4-Terpineol Natural products CC(C)[C@]1(O)CCC(C)=CC1 WRYLYDPHFGVWKC-SNVBAGLBSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
- 206010041349 Somnolence Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 231100000209 biodegradability test Toxicity 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- WMPOZLHMGVKUEJ-UHFFFAOYSA-N decanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCC(Cl)=O WMPOZLHMGVKUEJ-UHFFFAOYSA-N 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- IFYLVUHLOOCYBG-UHFFFAOYSA-N eticyclidine Chemical compound C=1C=CC=CC=1C1(NCC)CCCCC1 IFYLVUHLOOCYBG-UHFFFAOYSA-N 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229940066769 systemic antihistamines substituted alkylamines Drugs 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/36—Esters of polycarboxylic acids
-
- 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
- C09K8/34—Organic liquids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/34—Esters of monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/56—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing nitrogen
- C10M105/68—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/286—Esters of polymerised unsaturated acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/08—Amides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/08—Amides
- C10M2215/082—Amides containing hydroxyl groups; Alkoxylated derivatives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/28—Amides; Imides
Definitions
- the present invention relates to a temperature stable synthetic oil.
- the present invention relates to a synthetic oil based on alkyl esters or amides which are non-toxic and biodegradable and exhibit a high resistance to hydrolysis at elevated temperatures. These products are suitable for use as synthetic oils in applications where resistance to hydrolysis is important, such as in wellbore drilling.
- esters or polyesters which are subject to severe hydrolysis at about 150°C which causes problems. For example, breakdown of the esters yields alcohols which being water soluble can upset the osmotic pressure of the aqueous phase. Many of these ester alcohols are volatile and flammable and may collect in airspaces, presenting a possible explosion risk. In addition they can be inhaled by the drilling rig operators causing drowsiness and other health problems.
- the present invention seeks to overcome these problems.
- a synthetic lubricant composition resistant to hydrolysis at high temperature which composition comprises any one or more of a C 16 _ 42 ester, a C 16 _ 42 polyester, a C 16 _ 42 amide or a C 16 _ 42 polyamide.
- a synthetic lubricant composition resistant to hydrolysis at high temperature which composition comprises any one or more of a non-aromatic C 16 _ 42 ester, a non-aromatic C 16 _ 42 polyester, a non-aromatic C ]6 _ 42 amide or a non-aromatic C l6 _ 42 polyamide.
- a synthetic lubricant composition resistant to hydrolysis at high temperature which composition comprises a non-aromatic C 16 _ 2 amide.
- the amide has one or more of the following features:
- the carbon adjacent the nitrogen of the amide group is not linked to a hydrogen.
- ester, polyester, amide or polyamide is prepared from a diacid.
- the amide or polyamide is prepared from a dialkylamine, preferably a N,N di-alkylamine.
- ester, polyester, amide or polyamide are prepared from a .- ⁇ , saturated or olefinic, mono or polyfunctional alcohol or amine, respectively, wherein the alcohol or amine can optionally have one or more alkyl substitutions on the primary carbon atom or on the secondary carbon atom relative to the functional group, preferably on the primary carbon atom.
- substitutions are cycloaliphatics with the functional groups attached to the ring.
- the alcohol or amine is a secondary or a tertiary alcohol or a secondary or a tertiary amine, respectively, more preferably the alcohol is a secondary alcohol and the amine is a secondary or tertiary amine.
- the amine is an N-alkyl alkylamine.
- the alcohol or amine has limited water solubility, low volatility and has a flash point >35°C.
- the ester, polyester, amide or polyamide are prepared from mono or polyfunctional, saturated or olefinic reactants comprising free acid groups and free amine groups or free hydroxl groups respectively, wherein the number of free acid groups matches the number of free amine or hydroxyl groups.
- ester, polyester, amide or polyamide are prepared from an acid having substituted on the secondary carbon one or more alkyl groups such that the total number of carbon atoms in the substitucnts exceeds 2.
- ester, polyester, amide or polyamide are prepared from an acid having the secondary carbon atom as part of a cyclic structure.
- ester, polyester, amide or polyamide is a cyclic structure.
- ester or amide is converted into a cyclic polyester or polyamide respectively.
- ester or amide is blended with other oils of similar or different structures, in order to achieve the desired physical characteristics.
- composition is or is part of a synthetic oil for use in, for example, oil- based wellbore drilling muds.
- a preferred aspect of the present invention therefore relates to the use of non- aromatic . - j ,, saturated or olefinic, mono or polyfunctional alcohols or amines with low volatility and low water solubility, with flash points >35°C, having substitution on the primary (relative to the functional group(s)), or less preferably on the secondary, carbon atom(s).
- the alcohols and amines can be derived from natural products such as terpineols or synthetic materials such as cyclohexane 1,2-diol.
- the alkyl amines may be N-substituted alkyl amines.
- organic acids that are reacted with the alcohols or amines are non-aromatic, saturated or olefinic and can be mono or polyfunctional, chosen such that the total number of carbon atoms in the molecules described by this invention is in the range 16-42 and the number of acid groups matches the number of free amine or alcohol groups.
- Optional substitution by bulky sidegroups (i.e. >C 2 e.g. as dimethyl or ethyl groups) on the secondary carbon atom in the acid aliphatic chain impart a small further improvement in hydrolytic stability.
- the products may optionally be arranged in cyclic structures (e.g. 2,7-dimethyl-l,8- dioxane-9,18-dione from sebacoyl chloride and 2,5-dimethyl, 2,5-hexane diol). This results in a structure with poor low temperature properties but with increased oxidation stability.
- cyclic structures e.g. 2,7-dimethyl-l,8- dioxane-9,18-dione from sebacoyl chloride and 2,5-dimethyl, 2,5-hexane diol.
- oils produced according to this invention may be blended with other oils in order to produce a final blend with the desired characteristics.
- the prefered alcohols or amines are chosen from either a) cycloaliphatics, with the functional group(s) attached to the ring (e.g. terpinen-4-ol, bomeol, cyclopentanol, cyclohexamine, cyclohexane 1,2— diol, 1,4-diamino cyclohexane); or b) secondary or tertiary alcohols or amines (e.g. ⁇ -terpineol, 2,3 dimethyl butane 2,3-diol, 2- aminoheptane).
- cycloaliphatics with the functional group(s) attached to the ring
- the functional group(s) attached to the ring e.g. terpinen-4-ol, bomeol, cyclopentanol, cyclohexamine, cyclohexane 1,2— diol, 1,4-diamino cyclohexane
- 2,3-dimethyl 2,3-butane dioleate has a viscosity of 40 cP at 25 °C and a value of 150 cP at 0°C.
- the oil showed an increase in acid value of 0.07 mgKOH/g after 48 hours at 93 °C.
- the oil showed 97 % biodegradability after 21 days in accordance with the European Community Biodegradability Test Method CEC-L-33-T-82.
- the ⁇ -terpineol diester of 1,8-octanedioic acid has a viscosity of 30 cP at 25°C and 60 cP at 0°C.
- the oil showed an increase in acid value of 0.06 mgKOH/g after 48 hours at 93 °C.
- the oil showed 90 % biodegradability after 21 days (CEC-L-33-T-82).
- the present invention relates to a synthetic lubricant composition resistant to hydrolysis at high temperature which composition comprises any one or more of a C 16 _ 42 ester, a C 16 _ 42 polyester, a C 16 _ 42 amide or a . ⁇ . ⁇ polyamide.
- the present invention relates to a synthetic oil based on alkyl esters or amides which are non-toxic and biodegradable and exhibit a high resistance to hydrolysis at elevated temperatures. These products are suitable for use as synthetic oils in applications where resistance to hydrolysis is important, such as in wellbore drilling.
- non-aromatic . ⁇ saturated or olefinic, mono or polyfunctional alcohols or amines having substitution on the primary carbon atom(s) or less preferably on the secondary carbon atom(s) are reacted with non-aromatic mono- or poly-functional acids to yield (poly)esters or (poly)amides with a total number of carbon atoms between 16 and 42.
- the acid may optionally have substitution on the secondary carbon atom(s).
Abstract
A synthetic lubricant composition resistant to hydrolysis at high temperature which composition comprises any one or more of a C16-42 ester, a C16-42 polyester, a C16-42 amide or a C16-42 polyamide.
Description
TEMPERATURE STABLE SYNTHETIC OIL
The present invention relates to a temperature stable synthetic oil.
In particular, the present invention relates to a synthetic oil based on alkyl esters or amides which are non-toxic and biodegradable and exhibit a high resistance to hydrolysis at elevated temperatures. These products are suitable for use as synthetic oils in applications where resistance to hydrolysis is important, such as in wellbore drilling.
Some synthetic oils for wellbore drilling are disclosed in EP-A-0386636, EP-A- 0386638 and WO 93/23491.
Current technology uses esters or polyesters which are subject to severe hydrolysis at about 150°C which causes problems. For example, breakdown of the esters yields alcohols which being water soluble can upset the osmotic pressure of the aqueous phase. Many of these ester alcohols are volatile and flammable and may collect in airspaces, presenting a possible explosion risk. In addition they can be inhaled by the drilling rig operators causing drowsiness and other health problems.
The present invention seeks to overcome these problems.
According to a first aspect of the present invention there is provided a synthetic lubricant composition resistant to hydrolysis at high temperature which composition comprises any one or more of a C16_42 ester, a C16_42 polyester, a C16_42 amide or a C16_ 42 polyamide.
According to a second aspect of the present invention there is provided a synthetic lubricant composition resistant to hydrolysis at high temperature which composition comprises any one or more of a non-aromatic C16_42 ester, a non-aromatic C16_42 polyester, a non-aromatic C]6_42 amide or a non-aromatic Cl6_42 polyamide.
According to a third aspect of the present invention there is provided a synthetic lubricant composition resistant to hydrolysis at high temperature which composition comprises a non-aromatic C16_ 2 amide.
Preferably the amide has one or more of the following features:
1. the carbon atom adjacent the carbonyl group is not linked to a hydrogen
2. the carbon adjacent the nitrogen of the amide group is not linked to a hydrogen.
Preferably the ester, polyester, amide or polyamide is prepared from a diacid.
Preferably the amide or polyamide is prepared from a dialkylamine, preferably a N,N di-alkylamine.
Preferably the ester, polyester, amide or polyamide are prepared from a .-^, saturated or olefinic, mono or polyfunctional alcohol or amine, respectively, wherein the alcohol or amine can optionally have one or more alkyl substitutions on the primary carbon atom or on the secondary carbon atom relative to the functional group, preferably on the primary carbon atom.
Preferably the substitutions are cycloaliphatics with the functional groups attached to the ring.
Preferably the alcohol or amine is a secondary or a tertiary alcohol or a secondary or a tertiary amine, respectively, more preferably the alcohol is a secondary alcohol and the amine is a secondary or tertiary amine. Preferably the amine is an N-alkyl alkylamine.
Preferably the alcohol or amine has limited water solubility, low volatility and has a flash point >35°C.
Preferably the ester, polyester, amide or polyamide are prepared from mono or polyfunctional, saturated or olefinic reactants comprising free acid groups and free amine groups or free hydroxl groups respectively, wherein the number of free acid groups matches the number of free amine or hydroxyl groups.
Preferably the ester, polyester, amide or polyamide are prepared from an acid having substituted on the secondary carbon one or more alkyl groups such that the total number of carbon atoms in the substitucnts exceeds 2.
Preferably the ester, polyester, amide or polyamide are prepared from an acid having the secondary carbon atom as part of a cyclic structure.
Preferably the ester, polyester, amide or polyamide is a cyclic structure.
Preferably the ester or amide is converted into a cyclic polyester or polyamide respectively.
Preferably the ester or amide is blended with other oils of similar or different structures, in order to achieve the desired physical characteristics.
Preferably the composition is or is part of a synthetic oil for use in, for example, oil- based wellbore drilling muds.
A preferred aspect of the present invention therefore relates to the use of non- aromatic .-j,, saturated or olefinic, mono or polyfunctional alcohols or amines with low volatility and low water solubility, with flash points >35°C, having substitution on the primary (relative to the functional group(s)), or less preferably on the secondary, carbon atom(s). The alcohols and amines can be derived from natural products such as terpineols or synthetic materials such as cyclohexane 1,2-diol. Optionally, the alkyl amines may be N-substituted alkyl amines. The organic acids that are reacted with the alcohols or amines (either by direct reaction with the acid or via the acid chloride or a suitable ester (e.g. methyl)) are non-aromatic, saturated or
olefinic and can be mono or polyfunctional, chosen such that the total number of carbon atoms in the molecules described by this invention is in the range 16-42 and the number of acid groups matches the number of free amine or alcohol groups. Optional substitution by bulky sidegroups (i.e. >C2 e.g. as dimethyl or ethyl groups) on the secondary carbon atom in the acid aliphatic chain impart a small further improvement in hydrolytic stability. Where the structure of the components permits, the products may optionally be arranged in cyclic structures (e.g. 2,7-dimethyl-l,8- dioxane-9,18-dione from sebacoyl chloride and 2,5-dimethyl, 2,5-hexane diol). This results in a structure with poor low temperature properties but with increased oxidation stability.
In general, the use of unsaturatcd compounds results in oils with better low temperature rheology, improved biodegradability, but poorer oxidation stability. The oils produced according to this invention may be blended with other oils in order to produce a final blend with the desired characteristics.
Thus the prefered alcohols or amines are chosen from either a) cycloaliphatics, with the functional group(s) attached to the ring (e.g. terpinen-4-ol, bomeol, cyclopentanol, cyclohexamine, cyclohexane 1,2— diol, 1,4-diamino cyclohexane); or b) secondary or tertiary alcohols or amines (e.g. α-terpineol, 2,3 dimethyl butane 2,3-diol, 2- aminoheptane).
The present invention will now be described only by way of example.
Examples:
1. 2,3-dimethyl 2,3-butane dioleate has a viscosity of 40 cP at 25 °C and a value of 150 cP at 0°C. In the ASTM D2619 hydrolytic stability test, the oil showed an increase in acid value of 0.07 mgKOH/g after 48 hours at 93 °C. The oil showed 97 % biodegradability after 21 days in accordance with the European Community Biodegradability Test Method CEC-L-33-T-82.
2. The α-terpineol diester of 1,8-octanedioic acid has a viscosity of 30 cP at 25°C and 60 cP at 0°C. In the ASTM D2619 hydrolytic stability test, the oil showed an increase in acid value of 0.06 mgKOH/g after 48 hours at 93 °C. The oil showed 90 % biodegradability after 21 days (CEC-L-33-T-82).
3. The reaction product of two moles of dicyclohexylamine with dimethyl adipate yields an oil with a viscosity of 35 cP at 25 °C and 200 cP at 0 °C. In the ASTM D2619 hydrolytic stability test the acid value increase was 0.01 mgKOH/g after 48 hours at 93 °C. The oil showed 80 % biodegradability after 21 days (CEC-L-33-T- 82).
4. The reaction product of two moles of Versatic 10® acid chloride with 2,5-dimethyl 2,5-hexane diol yields and oil with a viscosity of 10 cP at 25 °C and a value of 40 cP at 0 °C. The ASTM hydrolytic stability test gave an increase in acid of 0.05 mgKOH/g after 48 hours at 93 °C. The oil showed 90 % biodegradability after 21 days (CEC-L-33-T-82).
In summation the present invention relates to a synthetic lubricant composition resistant to hydrolysis at high temperature which composition comprises any one or more of a C16_42 ester, a C16_42 polyester, a C16_42 amide or a .^.^ polyamide. Preferably the present invention relates to a synthetic oil based on alkyl esters or amides which are non-toxic and biodegradable and exhibit a high resistance to hydrolysis at elevated temperatures. These products are suitable for use as synthetic oils in applications where resistance to hydrolysis is important, such as in wellbore drilling. Preferably non-aromatic .^ saturated or olefinic, mono or polyfunctional alcohols or amines, having substitution on the primary carbon atom(s) or less preferably on the secondary carbon atom(s), are reacted with non-aromatic mono- or poly-functional acids to yield (poly)esters or (poly)amides with a total number of carbon atoms between 16 and 42. The acid may optionally have substitution on the secondary carbon atom(s).
Other modifications of the present invention will be apparent to those skilled in the art.
Claims
1. A synthetic lubricant composition resistant to hydrolysis at high temperature which composition comprises any one or more of a Ci6_A2 ester, a Ci6_42 polyester, a Ci6_42 amide or a C-l6_42 polyamide.
2. A synthetic lubricant composition resistant to hydrolysis at high temperature which composition comprises any one or more of a non-aromatic C16_42 ester, a non- aromatic C16_42 polyester, a non-aromatic Cι6_42 amide or a non-aromatic C16_42 polyamide.
3. A synthetic lubricant composition resistant to hydrolysis at high temperature which composition comprises a non-aromatic C16_ 2 amide.
4. A composition according to any one of claims 1 to 3 wherein the amide has one or more of the following features:
1. the carbon atom adjacent the carbonyl group is not linked to a hydrogen
2. the carbon adjacent the nitrogen of the amide group is not linked to a hydrogen.
5. A composition according to any one of claims 1 to 4 wherein the ester, polyester, amide or polyamide is prepared from a diacid.
6. A composition according to any one of claims 1 to 5 wherein the amide or polyamide is prepared from a dialkylamine, preferably a N,N di-alkylamine.
7. A composition according to any one of the preceding claims wherein the ester, polyester, amide or polyamide are prepared from a Cj.^ saturated or olefinic, mono or polyfunctional alcohol or amine, respectively, wherein the alcohol or amine can optionally have one or more alkyl substitutions on the primary carbon
atom or on the secondary carbon atom relative to the functional group, preferably on the primary carbon atom.
8. A composition according to claim 7 wherein the substitutions are cycloaliphatics with the functional groups attached to the ring.
9. A composition according to claim 7 or claim 8 wherein the alcohol or amine is a secondary or tertiary alcohol or amine, respectively.
10. A composition according to any one of claims 7 to 9 wherein the alcohol or amine has limited water solubility, low volatility and has a flash point >35°C.
11. A composition according to any one of claims 7 to 10 wherein the amine is an N-alkyl alkylamine.
12. A composition according to any one of the preceding claims wherein the ester, polyester, amide or polyamide are prepared from mono or polyfunctional, saturated or olefinic reactants comprising free acid groups and free amine groups or free hydroxl groups respectively, wherein the number of free acid groups matches the number of free amine or hydroxyl groups.
13. A composition according to any one of claims 7 to 12 wherein the ester, polyester, amide or polyamide are prepared from an acid having substituted on the secondary carbon one or more alkyl groups such that the total number of carbon atoms in the substituents exceeds 2.
14. A composition according to any one of claims 7 to 12 wherein the ester, polyester, amide or polyamide are prepared from an acid having the secondary carbon atom as part of a cyclic structure.
15. A composition according to any one of the preceding claims wherein the ester, polyester, amide or polyamide is a cyclic structure.
16. A composition according to any one of the preceding claims wherein the ester or amide is converted into a cyclic polyester or polyamide respectively.
17. A composition according to any one of the preceding claims wherein the ester or amide is blended with other oils of similar or different structures, in order to achieve the desired physical characteristics.
18. A composition according to any one of the preceding claims wherein the composition is or is part of a synthetic oil for use in, for example, oil-based wellbore drilling muds.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU25335/95A AU2533595A (en) | 1994-05-25 | 1995-05-24 | Temperature stable synthetic oil |
| GB9622225A GB2302098B (en) | 1994-05-25 | 1995-05-24 | Temperature stable synthetic oil |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9410511.1 | 1994-05-25 | ||
| GB9410511A GB9410511D0 (en) | 1994-05-25 | 1994-05-25 | Temperature stable synthetic oil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1995032265A1 true WO1995032265A1 (en) | 1995-11-30 |
Family
ID=10755725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/GB1995/001182 WO1995032265A1 (en) | 1994-05-25 | 1995-05-24 | Temperature stable synthetic oil |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU2533595A (en) |
| GB (2) | GB9410511D0 (en) |
| WO (1) | WO1995032265A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110872498A (en) * | 2018-08-30 | 2020-03-10 | 中石化石油工程技术服务有限公司 | Biomass synthetic base drilling fluid and preparation method thereof |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0374672A1 (en) * | 1988-12-19 | 1990-06-27 | Henkel Kommanditgesellschaft auf Aktien | Use of selected fatty esters in drilling fluids, especially in offshore oil or gas recovery |
| EP0386636A1 (en) * | 1989-03-08 | 1990-09-12 | Henkel Kommanditgesellschaft auf Aktien | Esters of medium chain size carboxylie acids as components of the oil phase of invert emulsion drilling fluids |
| EP0398113A1 (en) * | 1989-05-16 | 1990-11-22 | Henkel Kommanditgesellschaft auf Aktien | Use of selected ester oils in water based drilling fluids of the oil in water emulsion type, and drilling fluids with improved ecological qualities |
| DE4018228A1 (en) * | 1990-06-07 | 1991-12-12 | Henkel Kgaa | FLOWABLE DRILL TREATMENT AGENTS BASED ON CARBONIC DIESTERS |
| WO1991019771A1 (en) * | 1990-06-16 | 1991-12-26 | Henkel Kommanditgesellschaft Auf Aktien | Fluid borehole-conditioning agent based on polycarboxylic acid esters |
| WO1993023491A1 (en) * | 1992-05-18 | 1993-11-25 | Exxon Chemical Patents Inc. | Functional fluid |
| EP0606553A2 (en) * | 1993-01-11 | 1994-07-20 | Conoco Inc. | An ester base oil for lubricant compounds and process of making an ester base oil from an organic reaction by-product |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3903785A1 (en) * | 1989-02-09 | 1990-08-16 | Henkel Kgaa | OLEOPHILIC BASE AMINE COMPOUNDS AS ADDITIVES IN INVERT DRILLING CLOSURES |
| AU2350195A (en) * | 1994-05-04 | 1995-11-29 | Burwood Corporation Limited, The | Surfactant composition |
| GB2303133B (en) * | 1994-05-04 | 1998-12-09 | Burwood Corp Ltd The | Amide and imide compounds and their use as lubricant oils |
-
1994
- 1994-05-25 GB GB9410511A patent/GB9410511D0/en active Pending
-
1995
- 1995-05-24 AU AU25335/95A patent/AU2533595A/en not_active Abandoned
- 1995-05-24 WO PCT/GB1995/001182 patent/WO1995032265A1/en active Application Filing
- 1995-05-24 GB GB9622225A patent/GB2302098B/en not_active Expired - Lifetime
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0374672A1 (en) * | 1988-12-19 | 1990-06-27 | Henkel Kommanditgesellschaft auf Aktien | Use of selected fatty esters in drilling fluids, especially in offshore oil or gas recovery |
| EP0386636A1 (en) * | 1989-03-08 | 1990-09-12 | Henkel Kommanditgesellschaft auf Aktien | Esters of medium chain size carboxylie acids as components of the oil phase of invert emulsion drilling fluids |
| EP0398113A1 (en) * | 1989-05-16 | 1990-11-22 | Henkel Kommanditgesellschaft auf Aktien | Use of selected ester oils in water based drilling fluids of the oil in water emulsion type, and drilling fluids with improved ecological qualities |
| DE4018228A1 (en) * | 1990-06-07 | 1991-12-12 | Henkel Kgaa | FLOWABLE DRILL TREATMENT AGENTS BASED ON CARBONIC DIESTERS |
| WO1991019771A1 (en) * | 1990-06-16 | 1991-12-26 | Henkel Kommanditgesellschaft Auf Aktien | Fluid borehole-conditioning agent based on polycarboxylic acid esters |
| WO1993023491A1 (en) * | 1992-05-18 | 1993-11-25 | Exxon Chemical Patents Inc. | Functional fluid |
| EP0606553A2 (en) * | 1993-01-11 | 1994-07-20 | Conoco Inc. | An ester base oil for lubricant compounds and process of making an ester base oil from an organic reaction by-product |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110872498A (en) * | 2018-08-30 | 2020-03-10 | 中石化石油工程技术服务有限公司 | Biomass synthetic base drilling fluid and preparation method thereof |
| CN110872498B (en) * | 2018-08-30 | 2021-11-02 | 中石化石油工程技术服务有限公司 | Biomass synthetic base drilling fluid and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2533595A (en) | 1995-12-18 |
| GB9410511D0 (en) | 1994-07-13 |
| GB9622225D0 (en) | 1996-12-18 |
| GB2302098A (en) | 1997-01-08 |
| GB2302098B (en) | 1998-09-30 |
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