GB1108043A - Production of epoxy compounds - Google Patents
Production of epoxy compoundsInfo
- Publication number
- GB1108043A GB1108043A GB2485865A GB2485865A GB1108043A GB 1108043 A GB1108043 A GB 1108043A GB 2485865 A GB2485865 A GB 2485865A GB 2485865 A GB2485865 A GB 2485865A GB 1108043 A GB1108043 A GB 1108043A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroperoxide
- cumene
- specified
- converted
- oil
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 5
- 239000004593 Epoxy Substances 0.000 title 1
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 abstract 10
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 abstract 6
- 239000003054 catalyst Substances 0.000 abstract 6
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 abstract 6
- 229930195733 hydrocarbon Natural products 0.000 abstract 5
- 150000002432 hydroperoxides Chemical class 0.000 abstract 5
- 229910052750 molybdenum Inorganic materials 0.000 abstract 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract 3
- 229940058172 ethylbenzene Drugs 0.000 abstract 3
- -1 ethylene-propylenecyclopentadiene Chemical class 0.000 abstract 3
- 150000002430 hydrocarbons Chemical class 0.000 abstract 3
- 239000001282 iso-butane Substances 0.000 abstract 3
- 239000000944 linseed oil Substances 0.000 abstract 3
- 235000021388 linseed oil Nutrition 0.000 abstract 3
- 229910052711 selenium Inorganic materials 0.000 abstract 3
- 239000011669 selenium Substances 0.000 abstract 3
- 229910052721 tungsten Inorganic materials 0.000 abstract 3
- 229910052720 vanadium Inorganic materials 0.000 abstract 3
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 abstract 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 abstract 2
- OIGWAXDAPKFNCQ-UHFFFAOYSA-N 4-isopropylbenzyl alcohol Chemical compound CC(C)C1=CC=C(CO)C=C1 OIGWAXDAPKFNCQ-UHFFFAOYSA-N 0.000 abstract 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 2
- 239000006227 byproduct Substances 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- QXYJCZRRLLQGCR-UHFFFAOYSA-N dioxomolybdenum Chemical compound O=[Mo]=O QXYJCZRRLLQGCR-UHFFFAOYSA-N 0.000 abstract 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 abstract 2
- 230000033444 hydroxylation Effects 0.000 abstract 2
- 238000005805 hydroxylation reaction Methods 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- 239000011733 molybdenum Substances 0.000 abstract 2
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 abstract 2
- 150000004965 peroxy acids Chemical class 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 abstract 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 abstract 1
- GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical compound OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 abstract 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 229910015427 Mo2O3 Inorganic materials 0.000 abstract 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 239000005062 Polybutadiene Substances 0.000 abstract 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 abstract 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 1
- 229910052770 Uranium Inorganic materials 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000001273 butane Substances 0.000 abstract 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 1
- 239000004359 castor oil Substances 0.000 abstract 1
- 235000019438 castor oil Nutrition 0.000 abstract 1
- 229910052804 chromium Inorganic materials 0.000 abstract 1
- 235000005687 corn oil Nutrition 0.000 abstract 1
- 239000002285 corn oil Substances 0.000 abstract 1
- 235000012343 cottonseed oil Nutrition 0.000 abstract 1
- 239000002385 cottonseed oil Substances 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 150000001993 dienes Chemical class 0.000 abstract 1
- 238000006735 epoxidation reaction Methods 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 125000005456 glyceride group Chemical group 0.000 abstract 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 abstract 1
- OYMKLTPMFOCLTL-UHFFFAOYSA-N hydrogen peroxide;2-methylpropane Chemical compound OO.CC(C)C OYMKLTPMFOCLTL-UHFFFAOYSA-N 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 abstract 1
- OYMJNIHGVDEDFX-UHFFFAOYSA-J molybdenum tetrachloride Chemical class Cl[Mo](Cl)(Cl)Cl OYMJNIHGVDEDFX-UHFFFAOYSA-J 0.000 abstract 1
- LNDHQUDDOUZKQV-UHFFFAOYSA-J molybdenum tetrafluoride Chemical compound F[Mo](F)(F)F LNDHQUDDOUZKQV-UHFFFAOYSA-J 0.000 abstract 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 abstract 1
- 125000005609 naphthenate group Chemical group 0.000 abstract 1
- 229910052758 niobium Inorganic materials 0.000 abstract 1
- 239000004006 olive oil Substances 0.000 abstract 1
- 235000008390 olive oil Nutrition 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 abstract 1
- 229920002857 polybutadiene Polymers 0.000 abstract 1
- 229920001522 polyglycol ester Polymers 0.000 abstract 1
- 229920001195 polyisoprene Polymers 0.000 abstract 1
- 159000000001 potassium salts Chemical class 0.000 abstract 1
- 229910052702 rhenium Inorganic materials 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000003784 tall oil Substances 0.000 abstract 1
- 229910052715 tantalum Inorganic materials 0.000 abstract 1
- 229920001897 terpolymer Polymers 0.000 abstract 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 abstract 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 abstract 1
- 239000010937 tungsten Substances 0.000 abstract 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 abstract 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 abstract 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 abstract 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 abstract 1
- 229910052726 zirconium Inorganic materials 0.000 abstract 1
Classifications
-
- 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
- C07D301/19—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic hydroperoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
- C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
- C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
- C07C15/46—Styrene; Ring-alkylated styrenes
-
- 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
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37530964A | 1964-06-15 | 1964-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1108043A true GB1108043A (en) | 1968-03-27 |
Family
ID=23480363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2485865A Expired GB1108043A (en) | 1964-06-15 | 1965-06-11 | Production of epoxy compounds |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE665239A (enrdf_load_stackoverflow) |
| DE (1) | DE1518997C3 (enrdf_load_stackoverflow) |
| ES (1) | ES314228A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1460574A (enrdf_load_stackoverflow) |
| GB (1) | GB1108043A (enrdf_load_stackoverflow) |
| NL (1) | NL6507248A (enrdf_load_stackoverflow) |
| SE (1) | SE338669B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1209155A1 (de) * | 2000-11-20 | 2002-05-29 | Degussa AG | Koppelprodukt freies Verfahren zur Herstellung von Propylenoxid |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008014558A1 (de) * | 2008-03-15 | 2009-09-17 | Dracowo Forschungs- Und Entwicklungs Gmbh | Polycarbonsäure modifizierte native Epoxide |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB682067A (en) * | 1949-03-26 | 1952-11-05 | Distillers Co Yeast Ltd | Manufacture of 1,2-epoxy-2,4,4-trimethylpentane |
| US2644837A (en) * | 1951-04-27 | 1953-07-07 | Du Pont | Oxidation of olefinic compounds |
| DE942088C (de) * | 1952-03-13 | 1956-04-26 | Distillers Co Yeast Ltd | Verfahren zur Herstellung von 2, 3-Epoxybutan |
| US2870171A (en) * | 1956-05-21 | 1959-01-20 | Shell Dev | Epoxidation process |
| US3062841A (en) * | 1958-09-18 | 1962-11-06 | Shell Oil Co | Epoxidation of alpha, beta ethylenic ketones with organic hydroperoxides |
| NL300753A (enrdf_load_stackoverflow) * | 1962-11-20 |
-
1965
- 1965-06-08 NL NL6507248A patent/NL6507248A/xx unknown
- 1965-06-10 BE BE665239D patent/BE665239A/xx unknown
- 1965-06-11 GB GB2485865A patent/GB1108043A/en not_active Expired
- 1965-06-14 FR FR20652A patent/FR1460574A/fr not_active Expired
- 1965-06-15 ES ES0314228A patent/ES314228A1/es not_active Expired
- 1965-06-15 SE SE785665A patent/SE338669B/xx unknown
- 1965-06-15 DE DE19651518997 patent/DE1518997C3/de not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1209155A1 (de) * | 2000-11-20 | 2002-05-29 | Degussa AG | Koppelprodukt freies Verfahren zur Herstellung von Propylenoxid |
Also Published As
| Publication number | Publication date |
|---|---|
| BE665239A (enrdf_load_stackoverflow) | 1965-12-10 |
| DE1518997A1 (de) | 1969-11-27 |
| NL6507248A (enrdf_load_stackoverflow) | 1965-12-16 |
| DE1518997C3 (de) | 1982-04-01 |
| DE1518997B2 (de) | 1981-07-23 |
| ES314228A1 (es) | 1965-10-16 |
| SE338669B (enrdf_load_stackoverflow) | 1971-09-13 |
| FR1460574A (fr) | 1966-12-10 |
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