NO121946B - - Google Patents
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- Publication number
- NO121946B NO121946B NO168810A NO16881067A NO121946B NO 121946 B NO121946 B NO 121946B NO 168810 A NO168810 A NO 168810A NO 16881067 A NO16881067 A NO 16881067A NO 121946 B NO121946 B NO 121946B
- Authority
- NO
- Norway
- Prior art keywords
- glycidol
- azeotropic agent
- allyl alcohol
- column
- distillation
- Prior art date
Links
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 86
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 76
- 239000003795 chemical substances by application Substances 0.000 claims description 39
- 238000004821 distillation Methods 0.000 claims description 31
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 19
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 12
- 238000009835 boiling Methods 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 238000011084 recovery Methods 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000005292 vacuum distillation Methods 0.000 claims 3
- 239000000047 product Substances 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000006735 epoxidation reaction Methods 0.000 description 20
- 238000010992 reflux Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000000605 extraction Methods 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical compound OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- OIGWAXDAPKFNCQ-UHFFFAOYSA-N 4-isopropylbenzyl alcohol Chemical compound CC(C)C1=CC=C(CO)C=C1 OIGWAXDAPKFNCQ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- -1 fatty acid monoglycerides Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
- JRLPEMVDPFPYPJ-UHFFFAOYSA-N 1-ethyl-4-methylbenzene Chemical compound CCC1=CC=C(C)C=C1 JRLPEMVDPFPYPJ-UHFFFAOYSA-N 0.000 description 1
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
- DYPJJAAKPQKWTM-UHFFFAOYSA-N 2-chloropropane-1,3-diol Chemical compound OCC(Cl)CO DYPJJAAKPQKWTM-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001233242 Lontra Species 0.000 description 1
- 238000010793 Steam injection (oil industry) Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000005194 ethylbenzenes Chemical class 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003681 vanadium Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C29/82—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by azeotropic distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/32—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US567430A US3374153A (en) | 1966-07-25 | 1966-07-25 | Process for recovery of glycidol from alcohol by azeotropic distillation with a hydrocarbon |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO121946B true NO121946B (sv) | 1971-05-03 |
Family
ID=24267116
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO168810A NO121946B (sv) | 1966-07-25 | 1967-06-28 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3374153A (sv) |
| JP (1) | JPS517646B1 (sv) |
| BE (1) | BE701443A (sv) |
| BR (1) | BR6791509D0 (sv) |
| CH (1) | CH476716A (sv) |
| DK (1) | DK128162B (sv) |
| ES (1) | ES343385A1 (sv) |
| GB (1) | GB1183360A (sv) |
| IL (1) | IL28384A (sv) |
| LU (1) | LU54135A1 (sv) |
| NL (1) | NL159380B (sv) |
| NO (1) | NO121946B (sv) |
| SE (1) | SE349800B (sv) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3520907A (en) * | 1967-01-13 | 1970-07-21 | Celanese Corp | Recovery of hydrophilic oxirane compounds |
| US3655524A (en) * | 1970-04-27 | 1972-04-11 | Fmc Corp | Glycidol isolation by azeotropic distillation with a lower-boiling entrainer |
| US4082777A (en) * | 1970-05-22 | 1978-04-04 | Fmc Corporation | Glycidol process |
| IT1027410B (it) * | 1974-02-25 | 1978-11-20 | Degussa | Procedimento continuc per la produzione di glicide |
| JPS5515194U (sv) * | 1979-03-08 | 1980-01-30 | ||
| US4544453A (en) * | 1983-03-17 | 1985-10-01 | Atlantic Richfield Company | Stripping of unreacted glycol ethers and acids from an esterification reaction mixture |
| JP2686975B2 (ja) * | 1987-09-14 | 1997-12-08 | アルコ・ケミカル・カンパニー | 不斉エポキシン化法におけるキラルエポキシアルコールの採取法 |
| US4935101A (en) * | 1989-10-13 | 1990-06-19 | Arco Chemical Technology, Inc. | Process for the recovery of a water-insoluble epoxy alcohol |
| US5288882A (en) * | 1992-12-21 | 1994-02-22 | Arco Chemical Technology, L.P. | Process for recovering an optically active epoxy alcohol |
| CN116041281A (zh) * | 2022-12-01 | 2023-05-02 | 杭州蔚远医药科技有限公司 | 一种缩水甘油的工业化生产方法及其装置 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2903465A (en) * | 1959-09-08 | Epoxidation | ||
| US2224849A (en) * | 1937-11-06 | 1940-12-17 | Shell Dev | Process and products relating to glycidols |
| US2248635A (en) * | 1939-06-20 | 1941-07-08 | Shell Dev | Treatment of halogenated polyhydric alcohols |
| US3039940A (en) * | 1959-11-02 | 1962-06-19 | Celanese Corp | Purification |
| FR1306120A (fr) * | 1961-09-01 | 1962-10-13 | Electrochimie Soc | Procédé de récupération de catalyseur tungstique |
| NL6513621A (sv) * | 1964-11-09 | 1966-05-10 |
-
1966
- 1966-07-25 US US567430A patent/US3374153A/en not_active Expired - Lifetime
-
1967
- 1967-06-28 NO NO168810A patent/NO121946B/no unknown
- 1967-07-17 NL NL6709883.A patent/NL159380B/xx not_active IP Right Cessation
- 1967-07-17 BE BE701443D patent/BE701443A/xx unknown
- 1967-07-19 LU LU54135D patent/LU54135A1/xx unknown
- 1967-07-20 GB GB33346/67A patent/GB1183360A/en not_active Expired
- 1967-07-24 CH CH1044667A patent/CH476716A/fr not_active IP Right Cessation
- 1967-07-24 DK DK379567AA patent/DK128162B/da unknown
- 1967-07-24 ES ES343385A patent/ES343385A1/es not_active Expired
- 1967-07-24 IL IL28384A patent/IL28384A/en unknown
- 1967-07-25 BR BR191509/67A patent/BR6791509D0/pt unknown
- 1967-07-25 JP JP42047429A patent/JPS517646B1/ja active Pending
- 1967-07-25 SE SE10821/67*A patent/SE349800B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6709883A (sv) | 1968-01-26 |
| NL159380B (nl) | 1979-02-15 |
| LU54135A1 (sv) | 1969-05-21 |
| BE701443A (fr) | 1968-01-17 |
| IL28384A (en) | 1971-03-24 |
| BR6791509D0 (pt) | 1973-08-14 |
| DE1668198A1 (de) | 1971-08-05 |
| CH476716A (fr) | 1969-08-15 |
| DE1668198B2 (de) | 1975-08-28 |
| ES343385A1 (es) | 1968-09-01 |
| JPS517646B1 (sv) | 1976-03-10 |
| US3374153A (en) | 1968-03-19 |
| SE349800B (sv) | 1972-10-09 |
| DK128162B (da) | 1974-03-11 |
| GB1183360A (en) | 1970-03-04 |
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