DE1065831B - Verfahren zur einstufigen Epoxydierung von Estern unge sattigter höherer Fettsauren - Google Patents
Verfahren zur einstufigen Epoxydierung von Estern unge sattigter höherer FettsaurenInfo
- Publication number
- DE1065831B DE1065831B DENDAT1065831D DE1065831DA DE1065831B DE 1065831 B DE1065831 B DE 1065831B DE NDAT1065831 D DENDAT1065831 D DE NDAT1065831D DE 1065831D A DE1065831D A DE 1065831DA DE 1065831 B DE1065831 B DE 1065831B
- Authority
- DE
- Germany
- Prior art keywords
- acid
- hydrogen peroxide
- reaction
- esters
- epoxidation
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 25
- 150000002148 esters Chemical class 0.000 title claims description 15
- 238000006735 epoxidation reaction Methods 0.000 title claims description 13
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 7
- 229930195729 fatty acid Natural products 0.000 title claims description 7
- 239000000194 fatty acid Substances 0.000 title claims description 7
- 150000004665 fatty acids Chemical class 0.000 title claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 43
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 13
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 11
- 229920005989 resin Polymers 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 9
- 239000003729 cation exchange resin Substances 0.000 claims description 9
- -1 ester butyl oleate Chemical class 0.000 claims description 4
- 239000003921 oil Substances 0.000 claims description 4
- 235000019198 oils Nutrition 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 235000012424 soybean oil Nutrition 0.000 claims description 2
- 239000003549 soybean oil Substances 0.000 claims description 2
- 150000004671 saturated fatty acids Chemical class 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 229960000583 acetic acid Drugs 0.000 description 13
- 235000011054 acetic acid Nutrition 0.000 description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 9
- 239000011630 iodine Substances 0.000 description 9
- 229910052740 iodine Inorganic materials 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 150000004965 peroxy acids Chemical class 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000003456 ion exchange resin Substances 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000001195 (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000004674 formic acids Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 150000004672 propanoic acids Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
- B01J31/10—Ion-exchange resins sulfonated
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
- B01J2231/72—Epoxidation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US463060A US2919283A (en) | 1954-10-18 | 1954-10-18 | Process of epoxidation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1065831B true DE1065831B (de) | 1959-09-24 |
Family
ID=23838721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1065831D Pending DE1065831B (de) | 1954-10-18 | Verfahren zur einstufigen Epoxydierung von Estern unge sattigter höherer Fettsauren |
Country Status (6)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1135458B (de) * | 1960-07-11 | 1962-08-30 | Henkel & Cie Gmbh | Verfahren zum Epoxydieren von ungesaettigten aliphatischen Verbindungen |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL107618C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1955-04-26 | 1900-01-01 | ||
| US3169139A (en) * | 1960-01-20 | 1965-02-09 | Du Pont | Hydroxylation process for olefinic higher fatty acid and fatty acid ester |
| US3156709A (en) * | 1962-03-06 | 1964-11-10 | Du Pont | Oxidation process |
| US3242196A (en) * | 1963-02-20 | 1966-03-22 | Du Pont | Partially epoxidized drying oils and derivatives thereof and their preparation |
| US3404163A (en) * | 1965-07-02 | 1968-10-01 | Ashalnd Oil & Refining Company | Epoxidation process |
| DE3426792A1 (de) * | 1984-07-20 | 1986-01-23 | Degussa Ag, 6000 Frankfurt | Verfahren zur herstellung von monoperoxydicarbonsaeuren und deren salze |
| US6010729A (en) | 1998-08-20 | 2000-01-04 | Ecolab Inc. | Treatment of animal carcasses |
| US8075857B2 (en) | 2006-10-18 | 2011-12-13 | Ecolab Usa Inc. | Apparatus and method for making a peroxycarboxylic acid |
| US7547421B2 (en) | 2006-10-18 | 2009-06-16 | Ecolab Inc. | Apparatus and method for making a peroxycarboxylic acid |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2801253A (en) * | 1957-07-30 | In situ epoxidation of organic esters | ||
| US2443280A (en) * | 1946-05-29 | 1948-06-15 | Us Agriculture | Hydroxylation process |
| GB676891A (en) * | 1948-10-18 | 1952-08-06 | Alais & Froges & Camarque Cie | Process for the preparation of ª‡-glycols and their derivatives |
| US2485160A (en) * | 1948-10-23 | 1949-10-18 | Rohm & Haas | Process for the epoxidation of esters of oleic and linoleic acids |
| US2629735A (en) * | 1949-12-28 | 1953-02-24 | Standard Oil Dev Co | Reaction of ethers with acids using ion exchange resins catalysts |
-
0
- IT IT543296D patent/IT543296A/it unknown
- DE DENDAT1065831D patent/DE1065831B/de active Pending
- BE BE541953D patent/BE541953A/xx unknown
-
1954
- 1954-10-18 US US463060A patent/US2919283A/en not_active Expired - Lifetime
-
1955
- 1955-10-10 CH CH344710D patent/CH344710A/de unknown
- 1955-10-10 FR FR1132216D patent/FR1132216A/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1135458B (de) * | 1960-07-11 | 1962-08-30 | Henkel & Cie Gmbh | Verfahren zum Epoxydieren von ungesaettigten aliphatischen Verbindungen |
Also Published As
| Publication number | Publication date |
|---|---|
| IT543296A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| US2919283A (en) | 1959-12-29 |
| FR1132216A (fr) | 1957-03-06 |
| BE541953A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| CH344710A (de) | 1960-02-29 |
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