WO2015002746A3 - Biobased epoxidized fatty acid ester plasticizers - Google Patents

Biobased epoxidized fatty acid ester plasticizers Download PDF

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Publication number
WO2015002746A3
WO2015002746A3 PCT/US2014/043122 US2014043122W WO2015002746A3 WO 2015002746 A3 WO2015002746 A3 WO 2015002746A3 US 2014043122 W US2014043122 W US 2014043122W WO 2015002746 A3 WO2015002746 A3 WO 2015002746A3
Authority
WO
WIPO (PCT)
Prior art keywords
biobased
fatty acid
acid ester
ester plasticizers
epoxidized fatty
Prior art date
Application number
PCT/US2014/043122
Other languages
French (fr)
Other versions
WO2015002746A2 (en
Inventor
George F. Schaefer
John D. Bradshaw
Larry J. Baldwin
Ronald J. Raleigh
Brenda Hollo
Original Assignee
Ferro Corporation
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 Ferro Corporation filed Critical Ferro Corporation
Priority to EP14820291.4A priority Critical patent/EP3016938A4/en
Publication of WO2015002746A2 publication Critical patent/WO2015002746A2/en
Publication of WO2015002746A3 publication Critical patent/WO2015002746A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
    • C07D303/42—Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
    • C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1515—Three-membered rings
    • 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
    • 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
    • C11C3/006—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by oxidation

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Compounds useful as plasticizers and the synthesis thereof are disclosed. In general, the invention includes process of esterifying biobased alcohols to make biobased ester plasticizers and the plasticizers made by such processes.
PCT/US2014/043122 2013-07-01 2014-06-19 Biobased epoxidized fatty acid ester plasticizers WO2015002746A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP14820291.4A EP3016938A4 (en) 2013-07-01 2014-06-19 Biobased epoxidized fatty acid ester plasticizers

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201361841483P 2013-07-01 2013-07-01
US61/841,483 2013-07-01

Publications (2)

Publication Number Publication Date
WO2015002746A2 WO2015002746A2 (en) 2015-01-08
WO2015002746A3 true WO2015002746A3 (en) 2015-02-26

Family

ID=52144262

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2014/043122 WO2015002746A2 (en) 2013-07-01 2014-06-19 Biobased epoxidized fatty acid ester plasticizers

Country Status (2)

Country Link
EP (1) EP3016938A4 (en)
WO (1) WO2015002746A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107794122A (en) * 2017-11-16 2018-03-13 武汉工程大学 A kind of synthesis method of epoxidized soybean oil
CN108753466B (en) * 2018-05-24 2021-06-08 华南理工大学 Tea oil linoleic acid and preparation method and application thereof

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3377304A (en) * 1959-04-22 1968-04-09 Swift & Co High oxirane fatty esters
US3483247A (en) * 1960-04-28 1969-12-09 Monsanto Co Preparation of aliphatic benzyl esters
WO2006012917A1 (en) * 2004-08-06 2006-02-09 Cognis Ip Management Gmbh Use of fatty alcohols as plasticizer to improve the physical-mechanical properties and processability of phb and its co-polymers
US20090149586A1 (en) * 2007-12-10 2009-06-11 Nexoleum Bioderivados Ltda. Primary pvc plasticizers derived from vegetable oils, process for obtaining primary pvc plasticizers derived from vegetable oils and plasticized pvc composition
WO2009152068A1 (en) * 2008-06-11 2009-12-17 Ferro Corporation Asymmetric cyclic diester compounds
US20120277357A1 (en) * 2010-01-22 2012-11-01 Archer Daniels Midland Company Processes for making high purity renewable source-based plasticizers and products made therefrom

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3574160A (en) * 1967-12-07 1971-04-06 American Cyanamid Co Processing aids
US9034965B2 (en) * 2010-08-06 2015-05-19 Arkema Inc. Epoxidized composition and methods for making the same
MX341216B (en) * 2011-09-30 2016-08-11 Dow Global Technologies Llc Process for mixing polyvinyl chloride with a bio-based plasticizer.
SG10201508216WA (en) * 2011-10-14 2015-11-27 Galata Chemicals Llc Plasticizers derived from renewable feedstock

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3377304A (en) * 1959-04-22 1968-04-09 Swift & Co High oxirane fatty esters
US3483247A (en) * 1960-04-28 1969-12-09 Monsanto Co Preparation of aliphatic benzyl esters
WO2006012917A1 (en) * 2004-08-06 2006-02-09 Cognis Ip Management Gmbh Use of fatty alcohols as plasticizer to improve the physical-mechanical properties and processability of phb and its co-polymers
US20090149586A1 (en) * 2007-12-10 2009-06-11 Nexoleum Bioderivados Ltda. Primary pvc plasticizers derived from vegetable oils, process for obtaining primary pvc plasticizers derived from vegetable oils and plasticized pvc composition
WO2009152068A1 (en) * 2008-06-11 2009-12-17 Ferro Corporation Asymmetric cyclic diester compounds
US20120277357A1 (en) * 2010-01-22 2012-11-01 Archer Daniels Midland Company Processes for making high purity renewable source-based plasticizers and products made therefrom

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
GOMBERG, M. ET AL.: "The preparation of benzyl esters and other benzyl-derivatives from benzyl chloride.", J. AM. CHEM. SOC., vol. 42, no. 10, 1920, pages 2059 - 2072, XP055306414 *
HASLAM, EDWIN.: "Recent developments in methods for the esterification and protection of the carboxyl group.", TETRAHEDRON, vol. 36, 1980, pages 2409 - 2433, XP000652204 *
JAIME DE LA ZERDA ET AL.: "Selective monoetherification and monoesterification of diols and diacids under phase-transfer conditions.", TETRAHEDRON, vol. 45, no. 5, 1989, pages 1533 - 1536, XP002138240 *
MILINSK, MARIA CRISTINA ET AL.: "Influence of the esterification method on the quantification of olive oil fatty acids.", SEMINA: CIENCIAS EXATAS E TECNOLOGICAS, LANDARINA, vol. 32, no. 2, 2011, pages 139 - 150, XP008182666 *
See also references of EP3016938A4 *

Also Published As

Publication number Publication date
WO2015002746A2 (en) 2015-01-08
EP3016938A4 (en) 2017-05-24
EP3016938A2 (en) 2016-05-11

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