FI123683B - Menetelmä luonnollisen komposition katalyyttiseksi hapettamiseksi, joka kompositio sisältää tyydyttämättömiä rasvahappoja ja/tai niiden estereitä ja siitä saadun seoksen käyttö mono-, oligo- ja/tai polyestereiden valmistamiseksi - Google Patents

Menetelmä luonnollisen komposition katalyyttiseksi hapettamiseksi, joka kompositio sisältää tyydyttämättömiä rasvahappoja ja/tai niiden estereitä ja siitä saadun seoksen käyttö mono-, oligo- ja/tai polyestereiden valmistamiseksi Download PDF

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FI123683B
FI123683B FI20116188A FI20116188A FI123683B FI 123683 B FI123683 B FI 123683B FI 20116188 A FI20116188 A FI 20116188A FI 20116188 A FI20116188 A FI 20116188A FI 123683 B FI123683 B FI 123683B
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acid
mixture
process according
oil
group
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FI20116188A
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FI20116188A (fi
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Salme Koskimies
Jukka Tulisalo
Pauliina Pitkaenen
Minni Pirttimaa
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Teknologian Tutkimuskeskus Vtt
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Priority to PCT/FI2012/051175 priority patent/WO2013079791A1/en
Priority to EP12815719.5A priority patent/EP2785677A1/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/285—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with peroxy-compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • 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
    • C08K5/10—Esters; Ether-esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
    • C10G3/42—Catalytic treatment
    • 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
    • C10M105/42—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and 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
    • C10M105/42—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids
    • C10M105/44—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
    • 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
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/301—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic 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
    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
    • C10M2207/302—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
    • C10M2207/3025—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups 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
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/401—Fatty vegetable or animal oils 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
    • 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
    • C10N2040/25—Internal-combustion engines
    • 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
    • C10N2040/30—Refrigerators lubricants or compressors lubricants
    • 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
    • C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
    • C10N2060/04—Oxidation, e.g. ozonisation
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P30/00—Technologies relating to oil refining and petrochemical industry
    • Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock

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

Claims (18)

1. Menetelmä oligo- ja/tai polyesterien valmistamiseksi, tunnettu siitä, että menetelmä käsittää seuraavat vaiheet: a) hapetetaan luonnollinen koostumus, joka sisältää tyydyttymättömiä rasvahappoja ja/tai niiden estereitä kaksifaasisessa vesi-orgaanisessa järjestelmässä katalyyttisen järjestelmän läsnä ollessa, jossa orgaaninen faasi sisältää luonnollisen koostumuksen ja vesifaasi sisältää vesiliukoisen hapettavan aineen ja jossa katalyyttinen järjestelmä käsittää katalyytin ja faasinsiirtoaineen katalyyttiä varten; b) saatetaan seos, joka käsittää karboksyyli-, epoksi- ja/tai hydroksyylihappoja ja joka on saatavissa vaiheesta a), reagoimaan vähintään yhden alkoholin kanssa, jossa alkoholi valitaan joukosta, joka koostuu polyoleista, happokatalyytin läsnä ollessa re-aktioseoksen valmistamiseksi; ja c) neutraloidaan reaktioseos.
2. Patenttivaatimuksen 1 mukainen menetelmä, tunnettu siitä, että luonnollinen koostumus on mäntyöljyn rasvahapposeos (TOFA).
3. Patenttivaatimuksen 1 mukainen menetelmä, tunnettu siitä, että luonnollinen koostumus on kasviöljy, joka käsittää tyydyttymättömiä rasvahappoja triglyseridi- tai esteröityneessä muodossa. £2
4. Patenttivaatimuksen 1 tai 3 mukainen mene- o c\J telmä, tunnettu siitä, että luonnollinen koostu- o mus valitaan joukosta, joka koostuu seuraavista: pel- £2 lavaöljy, soijaöljy, rapsiöljy, rypsiöljy ja oliiviöl- x jy. CC
5. Patenttivaatimusten 3 tai 4 mukainen mene-oo oo telmä, tunnettu siitä, että luonnollinen koostuit mus on kasviöljystä saatavien rasvahappojen ja/tai ° niiden esterien seos.
6. Jonkin patenttivaatimuksista 1-5 mukainen menetelmä, tunnettu siitä, että vesiliukoinen hapettava aine käsittää vetyperoksidin.
7. Jonkin patenttivaatimuksista 1-6 mukainen menetelmä, tunnettu siitä, että vaihe a) toteutetaan 50 - 90 °C:n lämpötilassa, edullisesti 60 -80 °C:n lämpötilassa.
8. Jonkin patenttivaatimuksista 1-7 mukainen menetelmä, tunnettu siitä, että katalyytti valitaan joukosta, joka koostuu seuraavista: volframi-happo, molybdeenihappo, molybdeenihapon emäksiset suolat ja niiden mikä tahansa seos.
9. Jonkin patenttivaatimuksista 1-8 mukai nen menetelmä, tunnettu siitä, että faasinsiirto-aine katalyyttiä varten valitaan joukosta, joka koostuu seuraavista: di(hydrattu tali ) dimetyyliammoniumkloridi, pyridiniumsuolat, fos- foniumsuolat, kruunueetterit ja niiden mikä tahansa seos.
10. Jonkin patenttivaatimuksista 1-9 mukai nen menetelmä, tunnettu siitä, että vaihe b) toteutetaan liuottimen läsnä ollessa, jossa liuotin valitaan joukosta, joka koostuu seuraavista: tolueeni, ksyleeni ja niiden mikä tahansa seos.
11. Jonkin patenttivaatimuksista 1-10 mukainen menetelmä, tunnettu siitä, että vaihe b) „ toteutetaan 60 - 280 °C:n, edullisesti 90 - 260 °C:n o ja edullisemmin 100 - 200 °C:n lämpötilassa. l0
12. Jonkin patenttivaatimuksista 1-11 mu- O ^ kainen menetelmä, tunnettu siitä, että happokata- lyytti valitaan joukosta, joka koostuu seuraavista: £ rikkihappo (H2SO4) , metaanisulfonihappo (MeS03H) , suo- 00 lahappo (HC1) , fosforihappo (H3PO4) , p- cö tolueenisulfonihappo, titanaatit, (RO)4Ti, ti- 5 na(II)oksidi (SnO) ja ioninvaihtohartsit. c\j
13. Jonkin patenttivaatimuksista 1-12 mu kainen menetelmä, tunnettu siitä, että vähintään yksi alkoholi valitaan joukosta, joka koostuu seuraa-vista: neopentyyliglykoli, pentaerytritoli, trimetylo-lipropaani ja 2-butyyli-2-etyyli-l,3-propaanidioli .
14. Jonkin patenttivaatimuksista 1-13 mu kainen menetelmä, tunnettu siitä, että vaihe b) toteutetaan vähintään yhden propionihaposta, valeri-aanahaposta, kapronihaposta, adipiinihaposta, pelar-gonihaposta ja lauriinihaposta läsnä ollessa.
15. Jonkin patenttivaatimuksista 1-14 mu kainen menetelmä, tunnettu siitä, että vaihe c) käsittää reaktioseoksen käsittelemisen emäksellä, joka valitaan joukosta, joka koostuu seuraavista: trietyy- liamiini, dinatriumkarbonaatti (Na2<303) , natriumkarbonaatti (NaHC03) , natriumhydroksidi (NaOH), kaliumhydrok-sidi (KOH) ja niiden mikä tahansa seos.
16. Oligo- ja/tai polyesterit, jotka ovat saatavissa jonkin patenttivaatimuksista 1-15 mukaisella menetelmällä.
17. Oligo- ja/tai polyesterien, jotka ovat saatavissa jonkin patenttivaatimuksista 1-15 mukaisella menetelmällä, käyttö voiteluaineen valmistamiseksi .
18. Voiteluaine, tunnettu siitä, että se käsittää patenttivaatimuksen 16 mukaisia oligo- ja/tai co polyestereitä. δ (M m o i CO X cc CL CO CO δ δ (M
FI20116188A 2011-11-28 2011-11-28 Menetelmä luonnollisen komposition katalyyttiseksi hapettamiseksi, joka kompositio sisältää tyydyttämättömiä rasvahappoja ja/tai niiden estereitä ja siitä saadun seoksen käyttö mono-, oligo- ja/tai polyestereiden valmistamiseksi FI123683B (fi)

Priority Applications (3)

Application Number Priority Date Filing Date Title
FI20116188A FI123683B (fi) 2011-11-28 2011-11-28 Menetelmä luonnollisen komposition katalyyttiseksi hapettamiseksi, joka kompositio sisältää tyydyttämättömiä rasvahappoja ja/tai niiden estereitä ja siitä saadun seoksen käyttö mono-, oligo- ja/tai polyestereiden valmistamiseksi
PCT/FI2012/051175 WO2013079791A1 (en) 2011-11-28 2012-11-28 Method for catalytic oxidation of a natural composition including unsaturated fatty acids and/or esters thereof and the use of a mixture obtained therefrom for the production of mono-, oligo- and/or polyesters
EP12815719.5A EP2785677A1 (en) 2011-11-28 2012-11-28 Method for catalytic oxidation of a natural composition including unsaturated fatty acids and/or esters thereof and the use of a mixture obtained therefrom for the production of mono-, oligo- and/or polyesters

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FI20116188A FI123683B (fi) 2011-11-28 2011-11-28 Menetelmä luonnollisen komposition katalyyttiseksi hapettamiseksi, joka kompositio sisältää tyydyttämättömiä rasvahappoja ja/tai niiden estereitä ja siitä saadun seoksen käyttö mono-, oligo- ja/tai polyestereiden valmistamiseksi
FI20116188 2011-11-28

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CN103274930B (zh) * 2013-06-20 2015-05-27 南京工业大学 一种采用连续法制备植物油多元醇的方法
WO2015138803A1 (en) 2014-03-12 2015-09-17 Icahn School Of Medicine At Mount Sinai Method for identifying kidney allograft recipients at risk for chronic injury
CN113444783B (zh) 2014-06-26 2024-04-09 西奈山伊坎医学院 通过分析预示性基因集诊断亚临床和临床的急性排异的方法
CN112236137A (zh) 2018-04-16 2021-01-15 西奈山伊坎医学院 利用移植前接受者血液中转录组标志预测急性排斥反应和肾脏同种异体移植物丧失的方法和试剂盒
CN115746939B (zh) * 2019-03-28 2023-11-17 重庆宝篆新材料科技有限公司 一种可生物降解的环保型润滑剂的制备方法

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ES2381367T3 (es) * 2005-04-26 2012-05-25 Battelle Memorial Institute Métodos para la producción de polioles a partir de aceites y su uso en la producción de poliésteres y poliuretanos
US8419968B2 (en) * 2008-11-13 2013-04-16 Chemtura Corporation Lubricants for refrigeration systems
CA2748622C (en) * 2008-12-31 2016-11-01 Battelle Memorial Institute Preparation of esters and polyols by initial oxidative cleavage of fatty acids followed by esterification reactions
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