GB1529762A - Process for synthesizing specific complete polyol mixed esters - Google Patents
Process for synthesizing specific complete polyol mixed estersInfo
- Publication number
- GB1529762A GB1529762A GB5389/76A GB538976A GB1529762A GB 1529762 A GB1529762 A GB 1529762A GB 5389/76 A GB5389/76 A GB 5389/76A GB 538976 A GB538976 A GB 538976A GB 1529762 A GB1529762 A GB 1529762A
- Authority
- GB
- United Kingdom
- Prior art keywords
- anhydride
- prepared
- propylene glycol
- oleic
- stearoyl
- 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.)
- Expired
Links
- 229920005862 polyol Polymers 0.000 title abstract 9
- 150000002148 esters Chemical class 0.000 title abstract 7
- 150000003077 polyols Chemical class 0.000 title abstract 6
- 230000002194 synthesizing effect Effects 0.000 title 1
- -1 Polyol esters Chemical class 0.000 abstract 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 5
- OCNZHGHKKQOQCZ-CLFAGFIQSA-N [(z)-octadec-9-enoyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC(=O)CCCCCCC\C=C/CCCCCCCC OCNZHGHKKQOQCZ-CLFAGFIQSA-N 0.000 abstract 5
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 abstract 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- 239000004386 Erythritol Substances 0.000 abstract 4
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 abstract 4
- 150000008064 anhydrides Chemical class 0.000 abstract 4
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 abstract 4
- 229940009714 erythritol Drugs 0.000 abstract 4
- 235000019414 erythritol Nutrition 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 229960004063 propylene glycol Drugs 0.000 abstract 3
- FWNZKPKGBYWNJO-KVVVOXFISA-N (z)-octadec-9-enoic acid;propane-1,2-diol Chemical compound CC(O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O FWNZKPKGBYWNJO-KVVVOXFISA-N 0.000 abstract 2
- JEJLGIQLPYYGEE-UHFFFAOYSA-N 1,2-dipalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCCCCCC JEJLGIQLPYYGEE-UHFFFAOYSA-N 0.000 abstract 2
- GFAZGHREJPXDMH-UHFFFAOYSA-N 1,3-dipalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCC GFAZGHREJPXDMH-UHFFFAOYSA-N 0.000 abstract 2
- VDJAHYCCXYNHDE-UHFFFAOYSA-N 2-hydroxypropyl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(C)O VDJAHYCCXYNHDE-UHFFFAOYSA-N 0.000 abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 2
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 abstract 2
- QSQLTHHMFHEFIY-UHFFFAOYSA-N methyl behenate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OC QSQLTHHMFHEFIY-UHFFFAOYSA-N 0.000 abstract 2
- 238000005809 transesterification reaction Methods 0.000 abstract 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- BQNHSMJWMBBIEQ-UHFFFAOYSA-N (2-hydroxy-3-propanoyloxypropyl) propanoate Chemical compound CCC(=O)OCC(O)COC(=O)CC BQNHSMJWMBBIEQ-UHFFFAOYSA-N 0.000 abstract 1
- JEIBXSGPFSSXOY-CLCOLTQESA-N (z)-19,20-dihydroxy-19-methyldotetracont-9-ene-18,21-dione Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)C(O)C(C)(O)C(=O)CCCCCCC\C=C/CCCCCCCC JEIBXSGPFSSXOY-CLCOLTQESA-N 0.000 abstract 1
- XNUZWIXOUNSBLL-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl benzoate Chemical class OCC(CO)OC(=O)C1=CC=CC=C1 XNUZWIXOUNSBLL-UHFFFAOYSA-N 0.000 abstract 1
- QXRKTZLOURTFPJ-UHFFFAOYSA-N 1-(oxan-2-yl)ethyl 2-hydroxypropanoate Chemical compound C(C(O)C)(=O)OC(C)C1OCCCC1 QXRKTZLOURTFPJ-UHFFFAOYSA-N 0.000 abstract 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 abstract 1
- FCWGFTAUZVCLAK-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl docosanoate Chemical class CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC FCWGFTAUZVCLAK-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 abstract 1
- 229910010082 LiAlH Inorganic materials 0.000 abstract 1
- 235000019482 Palm oil Nutrition 0.000 abstract 1
- 235000019484 Rapeseed oil Nutrition 0.000 abstract 1
- KGSBKZXRGYMKBT-RZEXXKRKSA-N TG(18:1(9Z)/18:0/18:1(9Z)) Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC KGSBKZXRGYMKBT-RZEXXKRKSA-N 0.000 abstract 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- LENHYQCCISSXPD-UHFFFAOYSA-N [4-(4-octadecanoyloxybutanoyloxy)-4-oxobutyl] octadecanoate Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)OCCCC(=O)OC(CCCOC(CCCCCCCCCCCCCCCCC)=O)=O LENHYQCCISSXPD-UHFFFAOYSA-N 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical class C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 abstract 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract 1
- 239000004327 boric acid Substances 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229940110456 cocoa butter Drugs 0.000 abstract 1
- 235000019868 cocoa butter Nutrition 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 229940116333 ethyl lactate Drugs 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 239000001087 glyceryl triacetate Substances 0.000 abstract 1
- 235000013773 glyceryl triacetate Nutrition 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000002540 palm oil Substances 0.000 abstract 1
- 230000008707 rearrangement Effects 0.000 abstract 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 abstract 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 abstract 1
- 229960002622 triacetin Drugs 0.000 abstract 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
Classifications
-
- 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
-
- 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
- C11C3/02—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/549,400 US3989728A (en) | 1975-02-12 | 1975-02-12 | Process for synthesizing specific complete mixed polyol esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1529762A true GB1529762A (en) | 1978-10-25 |
Family
ID=24192878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5389/76A Expired GB1529762A (en) | 1975-02-12 | 1976-02-11 | Process for synthesizing specific complete polyol mixed esters |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3989728A (enExample) |
| JP (1) | JPS51136612A (enExample) |
| BE (1) | BE838443A (enExample) |
| CA (1) | CA1058202A (enExample) |
| DE (1) | DE2605329A1 (enExample) |
| DK (1) | DK57676A (enExample) |
| FR (1) | FR2300795A1 (enExample) |
| GB (1) | GB1529762A (enExample) |
| IE (1) | IE42637B1 (enExample) |
| IT (1) | IT1055219B (enExample) |
| LU (1) | LU74332A1 (enExample) |
| NL (1) | NL7601373A (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6015821A (en) * | 1995-05-01 | 2000-01-18 | Horrobin; David Frederick | Nicotinic acid esters and pharmaceutical compositions containing them |
| US6555700B1 (en) | 1995-05-01 | 2003-04-29 | Scotia Holdings Plc | 1,3-propane diol esters and ethers and methods for their use in drug delivery |
| USRE40546E1 (en) * | 1996-05-01 | 2008-10-21 | Scarista, Ltd. | 1,3-Propane diol esters and ethers and methods for their use in drug delivery |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0023062A1 (en) * | 1979-07-18 | 1981-01-28 | THE PROCTER & GAMBLE COMPANY | Hart butter fat composition, its preparation and use in chocolate manufacture |
| DE3041073C2 (de) * | 1980-10-31 | 1986-01-02 | Dynamit Nobel Ag, 5210 Troisdorf | Wollwachssubstitute |
| US4594259A (en) * | 1984-12-21 | 1986-06-10 | The Procter & Gamble Company | Temperable confectionery compositions having improved mouth melt suitable for chocolate |
| US4830787A (en) * | 1987-08-13 | 1989-05-16 | Nabisco Brands, Inc. | Low calorie fat mimetics comprising carboxy/carboxylate esters |
| IE65561B1 (en) * | 1989-10-05 | 1995-11-01 | Daiichi Seiyaku Co | Process for production of optically active 2-(tetrahydropyran-2-yloxy)-1-propanol |
| US5188858A (en) * | 1991-01-18 | 1993-02-23 | The Procter & Gamble Company | Propylene glycol diesters of medium chain and long chain saturated fatty acids useful as reduced calorie cocoa butter substitutes and hard butters |
| US5137660A (en) * | 1991-03-15 | 1992-08-11 | The Procter & Gamble Company | Regioselective synthesis of 1,3-disubstituted glycerides |
| JP3000149B1 (ja) * | 1999-03-08 | 2000-01-17 | 工業技術院長 | 生分解性高分子量脂肪族ポリエステル及びその製造方法 |
| JP5519157B2 (ja) * | 2009-01-19 | 2014-06-11 | 株式会社ダイセル | （メタ）アクリル酸エステルの製造法 |
| US8299281B2 (en) * | 2009-03-27 | 2012-10-30 | Exxonmobil Research And Engineering Company | Process for making triglyceride plasticizer from crude glycerol |
| US20200369594A1 (en) * | 2018-02-16 | 2020-11-26 | Carnot3, Llc | Compounds comprising short-chain fatty acid moieties and compositions and methods thereof |
| CN115850110B (zh) * | 2022-12-27 | 2024-02-20 | 苏州元素集化学工业有限公司 | 一种含有甘油酯结构的类神经酰胺化合物的合成方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2759954A (en) * | 1949-02-02 | 1956-08-21 | Chemical Foundation Inc | Refining crude fatty acid monoglyceride |
| US3175916A (en) * | 1961-12-11 | 1965-03-30 | Canada Packers Ltd | Preparing edible oils from tall oil fatty acids |
| NL300326A (enExample) * | 1962-11-12 | 1900-01-01 | ||
| US3410881A (en) * | 1965-02-18 | 1968-11-12 | Procter & Gamble | Process for synthesizing specific complete mixed polyol esters |
| US3878231A (en) * | 1971-08-11 | 1975-04-15 | Scm Corp | Acylation of symmetrical diglycerides with fatty acid anhydride |
| US3882155A (en) * | 1973-11-12 | 1975-05-06 | Procter & Gamble | Process for synthesizing specific complete mixed polyol esters |
-
1975
- 1975-02-12 US US05/549,400 patent/US3989728A/en not_active Expired - Lifetime
-
1976
- 1976-02-03 CA CA244,868A patent/CA1058202A/en not_active Expired
- 1976-02-11 LU LU74332A patent/LU74332A1/xx unknown
- 1976-02-11 FR FR7603723A patent/FR2300795A1/fr active Granted
- 1976-02-11 NL NL7601373A patent/NL7601373A/xx not_active Application Discontinuation
- 1976-02-11 DE DE19762605329 patent/DE2605329A1/de not_active Withdrawn
- 1976-02-11 IT IT20095/76A patent/IT1055219B/it active
- 1976-02-11 BE BE164225A patent/BE838443A/xx not_active IP Right Cessation
- 1976-02-11 GB GB5389/76A patent/GB1529762A/en not_active Expired
- 1976-02-12 DK DK57676*#A patent/DK57676A/da not_active Application Discontinuation
- 1976-02-12 IE IE277/76A patent/IE42637B1/en unknown
- 1976-02-12 JP JP51014350A patent/JPS51136612A/ja active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6015821A (en) * | 1995-05-01 | 2000-01-18 | Horrobin; David Frederick | Nicotinic acid esters and pharmaceutical compositions containing them |
| US6555700B1 (en) | 1995-05-01 | 2003-04-29 | Scotia Holdings Plc | 1,3-propane diol esters and ethers and methods for their use in drug delivery |
| USRE40480E1 (en) * | 1995-05-01 | 2008-09-02 | Scarista Limited | 1,3-Propane diol esters and ethers and methods for their use in drug delivery |
| USRE43632E1 (en) * | 1995-05-01 | 2012-09-04 | Scarista, Ltd. | 1,3-propane diol esters and ethers and methods for their use in drug delivery |
| USRE40546E1 (en) * | 1996-05-01 | 2008-10-21 | Scarista, Ltd. | 1,3-Propane diol esters and ethers and methods for their use in drug delivery |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51136612A (en) | 1976-11-26 |
| IE42637B1 (en) | 1980-09-24 |
| IE42637L (en) | 1976-08-12 |
| LU74332A1 (enExample) | 1976-12-31 |
| CA1058202A (en) | 1979-07-10 |
| FR2300795A1 (fr) | 1976-09-10 |
| DK57676A (da) | 1976-08-13 |
| BE838443A (fr) | 1976-08-11 |
| FR2300795B1 (enExample) | 1979-05-18 |
| IT1055219B (it) | 1981-12-21 |
| DE2605329A1 (de) | 1976-08-26 |
| NL7601373A (nl) | 1976-08-16 |
| US3989728A (en) | 1976-11-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |