GB765903A - Partial epoxidation of naturally occurring oils - Google Patents
Partial epoxidation of naturally occurring oilsInfo
- Publication number
- GB765903A GB765903A GB6429/55A GB642955A GB765903A GB 765903 A GB765903 A GB 765903A GB 6429/55 A GB6429/55 A GB 6429/55A GB 642955 A GB642955 A GB 642955A GB 765903 A GB765903 A GB 765903A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oil
- acid
- epoxidizing
- per cent
- mol
- 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
- 239000003921 oil Substances 0.000 title abstract 10
- 238000006735 epoxidation reaction Methods 0.000 title abstract 2
- 235000019198 oils Nutrition 0.000 abstract 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 6
- 239000003153 chemical reaction reagent Substances 0.000 abstract 4
- 229920005989 resin Polymers 0.000 abstract 4
- 239000011347 resin Substances 0.000 abstract 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- 241000273930 Brevoortia tyrannus Species 0.000 abstract 2
- 244000068988 Glycine max Species 0.000 abstract 2
- 235000010469 Glycine max Nutrition 0.000 abstract 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 abstract 2
- 235000019485 Safflower oil Nutrition 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- -1 Unsaturated fatty acid esters Chemical class 0.000 abstract 2
- LBAYFEDWGHXMSM-UHFFFAOYSA-N butaneperoxoic acid Chemical compound CCCC(=O)OO LBAYFEDWGHXMSM-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 235000005687 corn oil Nutrition 0.000 abstract 2
- 239000002285 corn oil Substances 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 239000000944 linseed oil Substances 0.000 abstract 2
- 235000021388 linseed oil Nutrition 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- 239000003813 safflower oil Substances 0.000 abstract 2
- 235000005713 safflower oil Nutrition 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 abstract 1
- 235000019341 magnesium sulphate Nutrition 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 235000010755 mineral Nutrition 0.000 abstract 1
- 235000021281 monounsaturated fatty acids Nutrition 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 abstract 1
- 230000035484 reaction time Effects 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 150000003626 triacylglycerols Chemical class 0.000 abstract 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Epoxy Resins (AREA)
Abstract
Halogen-containing resins and specifically vinyl-type resins are plasticized with partially epoxidized triglycerides obtained by heating naturally occurring unsaturated oils under epoxidizing conditions with only sufficient epoxidizing agent to epoxidize the mono-unsaturated fatty acid radicals and one double bond only of each poly-unsaturated fatty acid radical in the oil (see Group IV (b)).ALSO:Unsaturated fatty acid esters contained in naturally occurring oils are partially epoxidized by heating said oils under epoxidizing conditions with an epoxidizing reagent, the amount of which corresponds to 1 to 1.3 mol. of epoxidizing reagent for each double bond in each mol. of mono-unsaturated ester plus 1 to 1.3 mol. of epoxidizing reagent for one double bond only of each mol. of poly-unsaturated ester. The epoxidizing agent may be an aliphatic peracid containing from 1 to 10 carbon atoms, e.g. peracetic, performic or perbutyric acid, or may be hydrogen peroxide and an aliphatic carboxylic acid containing from 1 to 10 carbon atoms in the presence of 0.5 to 5 per cent by weight of sulphuric acid, and the reaction may be carried out with or without a solvent such as hexane or benzene. When a peracid is used, the reaction temperature may vary from 15 DEG to 35 DEG C. with reaction times of 1 to 4 hours, and a buffer such as sodium acetate is added to neutralize any mineral acid. The amount of epoxidizing reagent varies with the composition of the oil, the amount of double bonds to be reacted in order to obtain the required partially epoxidized ester being, for example, linseed oil 43.3 per cent, corn oil 68 per cent, menhaden oil 33.2 per cent, safflower oil 55 per cent, and soyabean oil 57.7 per cent. On completion of the reaction, the product is washed with water, filtered through anhydrous sodium carbonate if necessary, dried with magnesium sulphate and filtered. Detailed examples are given for the partial epoxidation of safflower oil, corn oil, linseed oil, menhaden oil, and soya bean oil, using as epoxidizing agent peracetic acid, or hydrogen peroxide and glacial acetic acid with sulphuric acid, or perbutyric acid or hydrogen peroxide and formic acid, with or without benzene as a solvent. The products may be used as plasticizers in halogen-containing resins and specifically vinyl-type resins.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US765903XA | 1954-03-23 | 1954-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB765903A true GB765903A (en) | 1957-01-16 |
Family
ID=22133000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6429/55A Expired GB765903A (en) | 1954-03-23 | 1955-03-04 | Partial epoxidation of naturally occurring oils |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB765903A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106220900A (en) * | 2016-07-26 | 2016-12-14 | 玉林市武宁油茶种植有限公司 | A kind of preparation method and applications of camellia seed oil plasticiser |
| CN107488518A (en) * | 2017-10-16 | 2017-12-19 | 中山职业技术学院 | A kind of epoxidized soybean oil and preparation method thereof |
-
1955
- 1955-03-04 GB GB6429/55A patent/GB765903A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106220900A (en) * | 2016-07-26 | 2016-12-14 | 玉林市武宁油茶种植有限公司 | A kind of preparation method and applications of camellia seed oil plasticiser |
| CN107488518A (en) * | 2017-10-16 | 2017-12-19 | 中山职业技术学院 | A kind of epoxidized soybean oil and preparation method thereof |
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