CA2809353C - High- and low-viscosity estolide base oils and lubricants - Google Patents

High- and low-viscosity estolide base oils and lubricants Download PDF

Info

Publication number
CA2809353C
CA2809353C CA2809353A CA2809353A CA2809353C CA 2809353 C CA2809353 C CA 2809353C CA 2809353 A CA2809353 A CA 2809353A CA 2809353 A CA2809353 A CA 2809353A CA 2809353 C CA2809353 C CA 2809353C
Authority
CA
Canada
Prior art keywords
alkyl
unbranched
saturated
branched
optionally substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CA2809353A
Other languages
English (en)
French (fr)
Other versions
CA2809353A1 (en
Inventor
Jakob Bredsguard
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Biosynthetic Technologies LLC
Original Assignee
Biosynthetic Technologies LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Biosynthetic Technologies LLC filed Critical Biosynthetic Technologies LLC
Publication of CA2809353A1 publication Critical patent/CA2809353A1/en
Application granted granted Critical
Publication of CA2809353C publication Critical patent/CA2809353C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05B—SPRAYING APPARATUS; ATOMISING APPARATUS; NOZZLES
    • B05B1/00—Nozzles, spray heads or other outlets, with or without auxiliary devices such as valves, heating means
    • B05B1/30—Nozzles, spray heads or other outlets, with or without auxiliary devices such as valves, heating means designed to control volume of flow, e.g. with adjustable passages
    • B05B1/32—Nozzles, spray heads or other outlets, with or without auxiliary devices such as valves, heating means designed to control volume of flow, e.g. with adjustable passages in which a valve member forms part of the outlet opening
    • B05B1/326—Gate valves; Sliding valves; Cocks
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05B—SPRAYING APPARATUS; ATOMISING APPARATUS; NOZZLES
    • B05B1/00—Nozzles, spray heads or other outlets, with or without auxiliary devices such as valves, heating means
    • B05B1/14—Nozzles, spray heads or other outlets, with or without auxiliary devices such as valves, heating means with multiple outlet openings; with strainers in or outside the outlet opening
    • B05B1/16—Nozzles, spray heads or other outlets, with or without auxiliary devices such as valves, heating means with multiple outlet openings; with strainers in or outside the outlet opening having selectively- effective outlets
    • B05B1/1627—Nozzles, spray heads or other outlets, with or without auxiliary devices such as valves, heating means with multiple outlet openings; with strainers in or outside the outlet opening having selectively- effective outlets with a selecting mechanism comprising a gate valve, a sliding valve or a cock
    • B05B1/1636—Nozzles, spray heads or other outlets, with or without auxiliary devices such as valves, heating means with multiple outlet openings; with strainers in or outside the outlet opening having selectively- effective outlets with a selecting mechanism comprising a gate valve, a sliding valve or a cock by relative rotative movement of the valve elements
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05B—SPRAYING APPARATUS; ATOMISING APPARATUS; NOZZLES
    • B05B1/00—Nozzles, spray heads or other outlets, with or without auxiliary devices such as valves, heating means
    • B05B1/30—Nozzles, spray heads or other outlets, with or without auxiliary devices such as valves, heating means designed to control volume of flow, e.g. with adjustable passages
    • B05B1/3026—Gate valves; Sliding valves; Cocks
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/465—Preparation of carboxylic acid esters by oligomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/604—Polycarboxylic acid esters, the acid moiety containing more than two carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic 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
    • C10M105/08—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
    • C10M105/08—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
    • 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
    • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
    • C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
    • C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
    • 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
    • C10M2207/2825—Esters of (cyclo)aliphatic oolycarboxylic acids used as base material
    • 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
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/102—Polyesters
    • C10M2209/1023—Polyesters used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/011—Cloud point
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/013—Iodine value
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/02—Viscosity; Viscosity index
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/069—Linear chain compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/071—Branched chain compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/081—Biodegradable compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/02—Pour-point; Viscosity index
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/64—Environmental friendly compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C11C3/08—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with fatty acids
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T137/00—Fluid handling
    • Y10T137/8593—Systems
    • Y10T137/86493—Multi-way valve unit
    • Y10T137/86549—Selective reciprocation or rotation
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T137/00—Fluid handling
    • Y10T137/8593—Systems
    • Y10T137/86493—Multi-way valve unit
    • Y10T137/86863—Rotary valve unit

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Emergency Medicine (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Lubricants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
CA2809353A 2010-08-31 2011-08-31 High- and low-viscosity estolide base oils and lubricants Active CA2809353C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US37889110P 2010-08-31 2010-08-31
US61/378,891 2010-08-31
US201161498499P 2011-06-17 2011-06-17
US61/498,499 2011-06-17
PCT/US2011/001537 WO2012030395A1 (en) 2010-08-31 2011-08-31 High-and low-viscosity estolide base oils and lubricants

Publications (2)

Publication Number Publication Date
CA2809353A1 CA2809353A1 (en) 2012-03-08
CA2809353C true CA2809353C (en) 2019-03-19

Family

ID=45773189

Family Applications (2)

Application Number Title Priority Date Filing Date
CA2809361A Expired - Fee Related CA2809361C (en) 2010-08-31 2011-08-31 Catalytic processes for preparing estolide base oils
CA2809353A Active CA2809353C (en) 2010-08-31 2011-08-31 High- and low-viscosity estolide base oils and lubricants

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CA2809361A Expired - Fee Related CA2809361C (en) 2010-08-31 2011-08-31 Catalytic processes for preparing estolide base oils

Country Status (6)

Country Link
US (14) US8455412B2 (enExample)
EP (3) EP2727982B1 (enExample)
JP (5) JP5890417B2 (enExample)
AU (3) AU2011296578B2 (enExample)
CA (2) CA2809361C (enExample)
WO (3) WO2012031048A1 (enExample)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2809361C (en) 2010-08-31 2018-11-06 Biosynthetic Technologies, Llc Catalytic processes for preparing estolide base oils
JP2014517123A (ja) 2011-06-17 2014-07-17 バイオシンセティック テクノロジーズ，リミティド ライアビリティ カンパニー エストリド基油を含むグリース組成物
US8268199B1 (en) * 2011-06-17 2012-09-18 Lubrigreen Biosynthetics, Llc Electrical devices and dielectric fluids containing estolide base oils
EP2702123A1 (en) * 2011-06-17 2014-03-05 Biosynthetic Technologies, LLC Epoxidized estolides, sulfurized estolides, and methods of making the same
MY191912A (en) 2011-06-17 2022-07-18 Biosynthetic Technologies Llc Estolide compositions exhibiting high oxidative stability
WO2012173671A1 (en) * 2011-06-17 2012-12-20 Lubrigreen Biosynthetics, Llc Compositions comprising estolide compounds and methods of making and using the same
CN103649282A (zh) * 2011-06-28 2014-03-19 陶氏环球技术有限责任公司 可用作生物润滑剂的酸酐衍生物
US20130065970A1 (en) * 2011-07-08 2013-03-14 Jakob BREDSGUARD Compositions and products containing estolide compounds
WO2013033519A1 (en) 2011-08-31 2013-03-07 Lubrigreen Biosynthetics, Llc Hydroxy estolides, poly-capped estolides, and methods of making the same
CA2894831C (en) 2011-12-19 2020-09-08 Biosynthetic Technologies, Llc Processes for preparing estolide base oils and oligomeric compounds that include cross metathesis
US20130234059A1 (en) * 2012-03-09 2013-09-12 Bob Lee Davis Haloalkene Complexes
US9145535B2 (en) 2012-04-04 2015-09-29 Biosynthetic Technologies, Llc Estolide compounds, estamide compounds, and lubricant compositions containing the same
WO2013184255A1 (en) * 2012-06-04 2013-12-12 Biosynthetic Technologies, Llc Processes for preparing estolide base oils and lubricants that include transesterification
WO2013191750A1 (en) 2012-06-18 2013-12-27 Biosynthetic Technologies, Llc Processes of preparing estolide compounds that include removing sulfonate residues
CN107267272A (zh) * 2012-11-19 2017-10-20 生物合成技术有限责任公司 基于第尔斯‑阿尔德的交内酯和润滑剂组合物
US10731064B1 (en) * 2012-12-31 2020-08-04 Bob Lee Davis Heat transfer fluid coordination entities
US9365796B2 (en) * 2013-09-25 2016-06-14 Biosynthetic Technologies, Llc Two-cycle lubricants comprising estolide compounds
EP3052600B1 (en) * 2013-10-02 2018-02-21 Biosynthetic Technologies, LLC Estolide compositions exhibiting superior properties in lubricant compositions
US20150144403A1 (en) * 2013-11-27 2015-05-28 Biosynthetic Technologies, Llc Drilling and fracturing fluids comprising estolide compounds
WO2015126624A1 (en) 2014-02-18 2015-08-27 Elevance Renewable Sciences, Inc. Branched-chain esters and methods of making and using the same
KR20160005904A (ko) 2014-07-08 2016-01-18 에스케이이노베이션 주식회사 에스톨라이드 화합물 및 그 제조방법
KR20160005905A (ko) 2014-07-08 2016-01-18 에스케이이노베이션 주식회사 케톤기 함유 에스톨라이드 화합물 및 그 제조방법
US9790138B2 (en) * 2014-09-01 2017-10-17 Boisynthetic Technologies, LLC Conversion of polyester-containing feedstocks into hydrocarbon products
US9624454B2 (en) 2014-09-25 2017-04-18 Biosynthetic Technologies, Llc Reclamation of estolide base oils from compositions comprising immiscible components
JP6345577B2 (ja) * 2014-11-26 2018-06-20 株式会社ユニバーサルエンターテインメント 情報提供システム、情報提供方法、プログラム、及びデータ構造
EP3383983A1 (en) * 2015-11-30 2018-10-10 Biosynthetic Technologies, LLC Ultra high-viscosity estolide base oils and method of making the same
EP3417015A4 (en) * 2016-02-19 2019-12-04 Rohm and Haas Company HIGH-PURE DISORBATESTER FROM TRIETHYLENE GLYCOL
WO2020152286A2 (de) * 2019-01-23 2020-07-30 Peter Greven GmbH & Co. KG Estolidester und ihre verwendung als basisöl in schmierstoffen
AU2020346578B2 (en) 2019-09-12 2023-07-13 Nihon Nohyaku Co., Ltd. Agricultural or horticultural insecticide or animal ectoparasite or endoparasite control agent each comprising an imidazopyridazine compound having a substituted cyclopropane-oxadiazole group or a salt thereof as active ingredient, and method for using the insecticide or the control agent
US12484581B2 (en) 2019-09-12 2025-12-02 Nihon Nohyaku Co., Ltd. Agricultural or horticultural insecticide or animal ectoparasite or endoparasite control agent each comprising a condensed heterocyclic compound having a substituted cyclopropane-oxadiazole group or a salt thereof as active ingredient, and method for using the insecticide or the control agent
WO2024058963A1 (en) 2022-09-12 2024-03-21 Heritage Research Group, Llc Rejuvenator for an asphalt pavement that leaves the surface black for an extended period of time

Family Cites Families (80)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2049072A (en) 1933-08-29 1936-07-28 Standard Oil Dev Co Lubricants
US2652411A (en) 1952-07-18 1953-09-15 Howard M Teeter Alkyl acyloxy stearates
US2862884A (en) 1954-03-23 1958-12-02 Texas Co Process for anhydrous calcium 12-hydroxy stearate and estolide containing grease
US3056818A (en) * 1955-10-13 1962-10-02 Goodrich Co B F Titanium and zirconium esterification catalysts
US3184480A (en) * 1962-12-04 1965-05-18 Eastman Kodak Co Process for preparing esters of 2, 2, 4, 4-tetramethyl-tetrahydro-3-furanol
US3299110A (en) 1963-08-22 1967-01-17 Exxon Research Engineering Co Condensation of carboxylic acids and olefins to produce esters
US3842019A (en) * 1969-04-04 1974-10-15 Minnesota Mining & Mfg Use of sulfonic acid salts in cationic polymerization
US4016200A (en) * 1974-03-12 1977-04-05 Mitsubishi Chemical Industries Ltd. Process for preparing carboxylic acid esters from toluene and xylene
US4431673A (en) 1980-05-02 1984-02-14 Revlon, Inc. Cosmetic compositions
CA1185260A (en) * 1981-04-24 1985-04-09 Kazuhisa Nakajima Process for preparing acetic acid esters
US4428850A (en) 1982-01-28 1984-01-31 Texaco Inc. Low foaming railway diesel engine lubricating oil compositions
US4567037A (en) 1984-11-20 1986-01-28 Revlon, Inc. Fatty acid diesters
US4639369A (en) 1986-03-03 1987-01-27 Revlon, Inc. Higher acyl lower alkyl hydroxystearates useful in cosmetics
US4867965A (en) 1986-10-02 1989-09-19 Revlon, Inc. Fatty acid diesters
US4806572A (en) 1987-05-04 1989-02-21 Creative Products Resource Asociates, Ltd. Hydrophilic foam pad for makeup removal
IT1226550B (it) * 1988-07-29 1991-01-24 Enichem Anic Spa Processo di oligomerizzazione selettiva di olefine e nuovo catalizzatore per tale processo.
US5011629A (en) * 1989-04-17 1991-04-30 Bilbo Raymond E Hydroxystearic polyesters of guerbet alcohols as polycarbonate lubricants
JP3171863B2 (ja) 1991-01-16 2001-06-04 伊藤製油株式会社 両性界面活性剤組成物
US5380894A (en) 1991-03-01 1995-01-10 The United States Of America As Represented By The Secretary Of Agriculture Production of hydroxy fatty acids and estolide intermediates
JP2916551B2 (ja) 1991-11-26 1999-07-05 富士写真フイルム株式会社 静電写真用液体現像剤
US5451332A (en) 1994-01-28 1995-09-19 The Lubrizol Corporation Estolides of hydroxy-containing triglycerides that contain a performance additive
US5427704A (en) 1994-01-28 1995-06-27 The Lubrizol Corporation Triglyceride oils thickened with estolides of hydroxy-containing triglycerides
US5458795A (en) 1994-01-28 1995-10-17 The Lubrizol Corporation Oils thickened with estolides of hydroxy-containing triglycerides
JPH07228881A (ja) 1994-02-17 1995-08-29 Ito Seiyu Kk エステル組成物
JPH0827473A (ja) * 1994-07-15 1996-01-30 Ito Seiyu Kk 潤滑剤
US5518728A (en) 1994-08-08 1996-05-21 L'oreal S.A. Cosmetic compositions for non-white pigmented skin
CA2208217A1 (en) 1994-12-08 1996-06-13 Exxon Chemical Patents, Inc. Biodegradable branched synthetic ester base stocks and lubricants formed therefrom
DE4444137A1 (de) * 1994-12-12 1996-06-13 Henkel Kgaa Synthetische Ester aus Alkoholen und Fettsäuregemischen aus ölsäurereichen, stearinsäurearmen Pflanzenölen
US6398986B1 (en) 1995-12-21 2002-06-04 Cooper Industries, Inc Food grade vegetable oil based dielectric fluid and methods of using same
JP3925958B2 (ja) * 1996-07-18 2007-06-06 出光興産株式会社 軸受油組成物
US20020036283A1 (en) 1997-04-11 2002-03-28 Neste Chemicals Oy Complex esters for use with fluorinated refrigerants
ATE337390T1 (de) 1997-11-14 2006-09-15 Us Agriculture Verwendung biologisch abbaubarer olsäure-estolid- ester als basisöl und schmieröl
US6018063A (en) 1998-11-13 2000-01-25 The United States Of America As Represented By The Secretary Of Agriculture Biodegradable oleic estolide ester base stocks and lubricants
GB9823853D0 (en) * 1998-10-30 1998-12-23 Bp Chem Int Ltd A process for making n-butyl esters from butadiene
US6316649B1 (en) 1998-11-13 2001-11-13 The United States Of America As Represented By The Secretary Of Agriculture Biodegradable oleic estolide ester having saturated fatty acid end group useful as lubricant base stock
DE19935914A1 (de) * 1999-07-30 2001-02-01 Sued Chemie Ag Verfahren zur Herstellung von Katalysatoren durch Säureaktivierung
JP3860942B2 (ja) 1999-11-18 2006-12-20 株式会社ジャパンエナジー 冷凍装置用潤滑油組成物、作動流体及び冷凍装置
CA2336513C (en) * 2000-02-17 2010-08-24 Tatsuo Tateno Process for producing fatty acid esters and fuels comprising fatty acid ester
EP1307422B1 (en) 2000-08-02 2016-09-21 MJ Research & Development, L.P. of which MJRD, LLC is a General Partner Transesterified fatty esters for lubricant and refrigerant oil system
RU2289568C2 (ru) 2001-03-26 2006-12-20 Дау Глобал Текнолоджиз Инк. Способ метатезиса сложных эфиров ненасыщенных жирных кислот или ненасыщенных жирных кислот с низшими олефинами и композиция гетерогенного катализатора, предназначенная для способа метатезиса
EP1423195B1 (en) 2001-08-01 2016-03-02 California Institute Of Technology Hexacoordinated ruthenium or osmium metal carbene metathesis catalysts
KR100556337B1 (ko) * 2002-02-05 2006-03-03 주식회사 가야에너지 단일단계 연속공정을 통한 고순도 지방산 알킬에스테르의제조방법
CA2512815A1 (en) 2003-01-13 2004-07-29 Cargill, Incorporated Method for making industrial chemicals
JP2005068077A (ja) * 2003-08-25 2005-03-17 Mitsubishi Chemicals Corp （メタ）アクリル酸エステル類の製造方法
CN100528827C (zh) 2003-10-02 2009-08-19 独立行政法人科学技术振兴机构 酯的制备方法
US20070092475A1 (en) 2005-10-24 2007-04-26 Alan Wohlman Methods for enhancing the morphology, tone, texture and/or appearance of skin using a Meadowestolide
US7998339B2 (en) 2005-12-12 2011-08-16 Neste Oil Oyj Process for producing a hydrocarbon component
WO2007081987A2 (en) 2006-01-10 2007-07-19 Elevance Renewable Sciences, Inc. Method of making hydrogenated metathesis products
WO2007094211A1 (ja) 2006-02-14 2007-08-23 National Institute Of Advanced Industrial Science And Technology カルボン酸エステルおよびエーテル化合物の製造方法
US7897884B2 (en) 2006-05-11 2011-03-01 Ypoint Capital, Inc. Method and system of a multi-zone capacitive force-measuring based load sensing platform
US7897798B2 (en) * 2006-08-04 2011-03-01 Mcneff Research Consultants, Inc. Methods and apparatus for producing alkyl esters from lipid feed stocks and systems including same
EP1889641A1 (de) 2006-08-18 2008-02-20 Cognis IP Management GmbH Kosmetische Zusammensetzungen enthaltend Ester auf Basis von 2-Ethylbutanol
FR2906530B1 (fr) * 2006-09-29 2012-02-17 Stearinerie Dubois Fils Procede de synthese d'esters d'estolides.
US8501973B2 (en) 2006-10-13 2013-08-06 Elevance Renewable Sciences, Inc. Synthesis of terminal alkenes from internal alkenes via olefin metathesis
SG177150A1 (en) 2006-12-26 2012-01-30 Denki Kagaku Kogyo Kk Tubular forming material and its heat-shrinkable film
US8268187B2 (en) 2007-12-21 2012-09-18 Chevron U.S.A. Inc. Refrigeration oil from gas-to-liquid-derived and bio-derived diesters
CN101903508B (zh) 2007-12-21 2014-12-03 雪佛龙美国公司 来自气变液衍生的二酯和生物衍生的二酯的致冷油
CN101932685B (zh) 2007-12-21 2014-12-03 雪佛龙美国公司 来自气变液衍生的三酯和生物衍生的三酯的制冷油
US7666828B2 (en) 2008-01-22 2010-02-23 Stepan Company Sulfonated estolides and other derivatives of fatty acids, methods of making them, and compositions and processes employing them
US8530684B2 (en) 2008-04-01 2013-09-10 Sk Chemicals Co., Ltd. Method for preparing fatty acid alkyl ester using fatty acid
JP5646460B2 (ja) * 2008-05-14 2014-12-24 カウンシル オブ サイエンティフィック アンド インダストリアル リサーチ 有効な潤滑剤ベースストックとしてのヒマシ油脂肪酸系エストリドエステルおよびそれらの誘導体
BRPI0803361A2 (pt) 2008-06-30 2010-03-09 Petroleo Brasileiro Sa processo de extração lìquido-lìquido para a purificação de estolides para uso como lubrificantes
US8273694B2 (en) 2008-07-28 2012-09-25 Jeffrey A Brown Synthetic compositions obtained from algae
US8119588B2 (en) 2009-01-21 2012-02-21 Stepan Company Hard surface cleaner compositions of sulfonated estolides and other derivatives of fatty acids and uses thereof
EP2451768A1 (en) 2009-07-10 2012-05-16 Dow Global Technologies LLC Esters of secondary hydroxy fatty acid oligomers and preparation thereof
EP2480642A1 (en) 2009-09-24 2012-08-01 Dow Global Technologies LLC Estolide compositions having excellent low temperature properties
EP2539422A1 (en) 2010-02-26 2013-01-02 Dow Global Technologies LLC Estolide derivatives useful as biolubricants
JP5996527B2 (ja) 2010-05-28 2016-09-21 テラヴィア ホールディングス， インコーポレイテッド 用途に応じた油を含む食品成分
CA2809361C (en) 2010-08-31 2018-11-06 Biosynthetic Technologies, Llc Catalytic processes for preparing estolide base oils
WO2012061101A1 (en) 2010-10-25 2012-05-10 Stepan Company Sulfonates from natural oil metathesis
MY191912A (en) 2011-06-17 2022-07-18 Biosynthetic Technologies Llc Estolide compositions exhibiting high oxidative stability
WO2012173671A1 (en) 2011-06-17 2012-12-20 Lubrigreen Biosynthetics, Llc Compositions comprising estolide compounds and methods of making and using the same
US8268199B1 (en) 2011-06-17 2012-09-18 Lubrigreen Biosynthetics, Llc Electrical devices and dielectric fluids containing estolide base oils
EP2702123A1 (en) 2011-06-17 2014-03-05 Biosynthetic Technologies, LLC Epoxidized estolides, sulfurized estolides, and methods of making the same
JP2014517123A (ja) 2011-06-17 2014-07-17 バイオシンセティック テクノロジーズ，リミティド ライアビリティ カンパニー エストリド基油を含むグリース組成物
US20130065970A1 (en) 2011-07-08 2013-03-14 Jakob BREDSGUARD Compositions and products containing estolide compounds
WO2013033519A1 (en) 2011-08-31 2013-03-07 Lubrigreen Biosynthetics, Llc Hydroxy estolides, poly-capped estolides, and methods of making the same
CA2894831C (en) 2011-12-19 2020-09-08 Biosynthetic Technologies, Llc Processes for preparing estolide base oils and oligomeric compounds that include cross metathesis
WO2013184255A1 (en) 2012-06-04 2013-12-12 Biosynthetic Technologies, Llc Processes for preparing estolide base oils and lubricants that include transesterification
WO2013191750A1 (en) 2012-06-18 2013-12-27 Biosynthetic Technologies, Llc Processes of preparing estolide compounds that include removing sulfonate residues

Also Published As

Publication number Publication date
US20140171671A1 (en) 2014-06-19
US8975425B2 (en) 2015-03-10
US20160289163A1 (en) 2016-10-06
WO2012030398A8 (en) 2012-09-27
JP2018087194A (ja) 2018-06-07
US9328305B2 (en) 2016-05-03
US8450256B2 (en) 2013-05-28
CA2809361A1 (en) 2012-03-08
AU2011296575B2 (en) 2014-04-24
JP2013536887A (ja) 2013-09-26
EP2611891A1 (en) 2013-07-10
WO2012031048A1 (en) 2012-03-08
US9878973B2 (en) 2018-01-30
US20130245298A1 (en) 2013-09-19
US20130274493A1 (en) 2013-10-17
AU2014203810B2 (en) 2016-08-11
US20130118893A1 (en) 2013-05-16
EP2727982A1 (en) 2014-05-07
AU2014203810A1 (en) 2014-07-31
WO2012030395A1 (en) 2012-03-08
US9228146B2 (en) 2016-01-05
US8486875B2 (en) 2013-07-16
US9650328B2 (en) 2017-05-16
US20120178660A1 (en) 2012-07-12
US20170152205A1 (en) 2017-06-01
EP2727982B1 (en) 2021-11-10
US20180154378A1 (en) 2018-06-07
US8716206B2 (en) 2014-05-06
US20160318843A1 (en) 2016-11-03
WO2012030398A1 (en) 2012-03-08
AU2011296578A1 (en) 2013-02-21
US20150197477A1 (en) 2015-07-16
US20120083435A1 (en) 2012-04-05
US20120172609A1 (en) 2012-07-05
EP2611890B1 (en) 2016-04-27
JP2016153491A (ja) 2016-08-25
EP2611890A1 (en) 2013-07-10
US8455412B2 (en) 2013-06-04
JP2016104746A (ja) 2016-06-09
AU2011296578B2 (en) 2014-08-21
JP2013536838A (ja) 2013-09-26
US8637689B2 (en) 2014-01-28
US20150005212A1 (en) 2015-01-01
US20150210950A1 (en) 2015-07-30
CA2809353A1 (en) 2012-03-08
CA2809361C (en) 2018-11-06
JP5890417B2 (ja) 2016-03-22
AU2011296575A1 (en) 2013-02-21

Similar Documents

Publication Publication Date Title
CA2809353C (en) High- and low-viscosity estolide base oils and lubricants
AU2017203283B2 (en) Diels Alder based estolide and lubricant compositions
JP2013536887A5 (enExample)
AU2016364959A1 (en) Ultra high-viscosity estolide base oils and method of making the same

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20160401