CA1178621A - Production of ethylene glycol by reaction of methanol, an organic peroxide and formaldehyde - Google Patents
Production of ethylene glycol by reaction of methanol, an organic peroxide and formaldehydeInfo
- Publication number
- CA1178621A CA1178621A CA000384302A CA384302A CA1178621A CA 1178621 A CA1178621 A CA 1178621A CA 000384302 A CA000384302 A CA 000384302A CA 384302 A CA384302 A CA 384302A CA 1178621 A CA1178621 A CA 1178621A
- Authority
- CA
- Canada
- Prior art keywords
- weight percent
- reaction
- ethylene glycol
- methanol
- formaldehyde
- 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims abstract description 129
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims abstract description 81
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims abstract description 53
- 150000001451 organic peroxides Chemical class 0.000 title claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 title claims description 32
- 238000004519 manufacturing process Methods 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical group CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 239000012969 di-tertiary-butyl peroxide Substances 0.000 claims description 15
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims description 8
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 5
- 229960004279 formaldehyde Drugs 0.000 claims 2
- 235000019256 formaldehyde Nutrition 0.000 claims 2
- 230000006872 improvement Effects 0.000 claims 1
- 229940093476 ethylene glycol Drugs 0.000 description 35
- 239000000047 product Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 238000006471 dimerization reaction Methods 0.000 description 4
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229940093470 ethylene Drugs 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical group CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 240000001987 Pyrus communis Species 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- -1 dimethyl dichloro succinate Chemical compound 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- CDPPYCZVWYZBJH-UHFFFAOYSA-N 2,2,3,3-tetramethylbutanedioic acid Chemical compound OC(=O)C(C)(C)C(C)(C)C(O)=O CDPPYCZVWYZBJH-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
- 229940089960 chloroacetate Drugs 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- OYFJQPXVCSSHAI-QFPUQLAESA-N enalapril maleate Chemical compound OC(=O)\C=C/C(O)=O.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 OYFJQPXVCSSHAI-QFPUQLAESA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- KQVYJVGVOIRXDT-UHFFFAOYSA-N ethylperoxymethylbenzene Chemical compound CCOOCC1=CC=CC=C1 KQVYJVGVOIRXDT-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000011551 heat transfer agent Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004434 industrial solvent Substances 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000004058 oil shale Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006025 oxidative dimerization reaction Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
-
- 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
- C07C29/32—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/183,537 US4337371A (en) | 1980-09-02 | 1980-09-02 | Production of ethylene glycol by reaction of methanol, an organic peroxide and formaldehyde |
| US183,537 | 1980-09-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1178621A true CA1178621A (en) | 1984-11-27 |
Family
ID=22673227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000384302A Expired CA1178621A (en) | 1980-09-02 | 1981-08-20 | Production of ethylene glycol by reaction of methanol, an organic peroxide and formaldehyde |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4337371A (en, 2012) |
| JP (2) | JPS5781423A (en, 2012) |
| BE (2) | BE890171A (en, 2012) |
| BR (1) | BR8105592A (en, 2012) |
| CA (1) | CA1178621A (en, 2012) |
| DE (1) | DE3134047A1 (en, 2012) |
| ES (1) | ES505102A0 (en, 2012) |
| FR (1) | FR2489307B1 (en, 2012) |
| GB (1) | GB2083038B (en, 2012) |
| IT (1) | IT1138182B (en, 2012) |
| MX (1) | MX157218A (en, 2012) |
| NL (1) | NL8104053A (en, 2012) |
| PT (1) | PT73574B (en, 2012) |
| SE (1) | SE8105173L (en, 2012) |
| ZA (2) | ZA816056B (en, 2012) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4412085A (en) * | 1980-09-02 | 1983-10-25 | John Kollar | Process for producing ethylene glycol |
| AU559375B2 (en) * | 1981-07-28 | 1987-03-05 | Redox Technologies Inc. | Glycol from methanol |
| US4412084A (en) * | 1981-07-28 | 1983-10-25 | John Kollar | Process for producing ethylene glycol |
| DE3373650D1 (en) * | 1982-11-27 | 1987-10-22 | British Petroleum Co Plc | Process for the production of ethylene glycol |
| US4478694A (en) * | 1983-10-11 | 1984-10-23 | Ska Associates | Methods for the electrosynthesis of polyols |
| US4602102A (en) * | 1984-12-19 | 1986-07-22 | Texaco Inc. | Production of alkyl glycolates |
| US4628108A (en) * | 1984-12-19 | 1986-12-09 | Texaco Inc. | Production of 2-substituted-1,3-dioxolanes from 1,3-dioxolane and formaldehyde |
| US4554364A (en) * | 1984-12-19 | 1985-11-19 | Texaco Inc. | Production of 2-hydroxyalkyl-1,3-dioxolanes |
| US4550184A (en) * | 1984-12-19 | 1985-10-29 | Texaco Inc. | Production of 2-hydroxymethyl-1,3-dioxolane |
| DE4023255A1 (de) * | 1990-07-21 | 1992-01-23 | Basf Ag | Verfahren zur herstellung von glykolen, insbesondere propylenglykol aus formaldehyd |
| CN102417438B (zh) * | 2011-10-27 | 2013-11-06 | 大连理工大学 | 一种转化甲醇的方法 |
| CN115073300B (zh) * | 2021-03-10 | 2024-04-05 | 江西天宇化工有限公司 | 一种4-(全氟丙烷-2-基)-2-三氟甲基苯胺及其制备方法和应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3076846A (en) * | 1957-02-08 | 1963-02-05 | Du Pont | Coupling by hydroxyl radicals and new triamino compounds |
| US4076758A (en) * | 1976-12-09 | 1978-02-28 | Monsanto Company | Synthesis of vicinal glycols |
-
1980
- 1980-09-02 US US06/183,537 patent/US4337371A/en not_active Expired - Lifetime
-
1981
- 1981-08-20 CA CA000384302A patent/CA1178621A/en not_active Expired
- 1981-08-25 MX MX188877A patent/MX157218A/es unknown
- 1981-08-26 PT PT73574A patent/PT73574B/pt unknown
- 1981-08-28 DE DE19813134047 patent/DE3134047A1/de active Granted
- 1981-08-31 FR FR8116583A patent/FR2489307B1/fr not_active Expired
- 1981-09-01 JP JP56136198A patent/JPS5781423A/ja active Granted
- 1981-09-01 ZA ZA816056A patent/ZA816056B/xx unknown
- 1981-09-01 ES ES505102A patent/ES505102A0/es active Granted
- 1981-09-01 IT IT23719/81A patent/IT1138182B/it active
- 1981-09-01 BR BR8105592A patent/BR8105592A/pt unknown
- 1981-09-01 ZA ZA816055A patent/ZA816055B/xx unknown
- 1981-09-01 GB GB8126453A patent/GB2083038B/en not_active Expired
- 1981-09-01 BE BE0/205835A patent/BE890171A/fr not_active IP Right Cessation
- 1981-09-01 JP JP56136197A patent/JPS5781422A/ja active Pending
- 1981-09-01 BE BE0/205834A patent/BE890170A/fr not_active IP Right Cessation
- 1981-09-01 NL NL8104053A patent/NL8104053A/nl not_active Application Discontinuation
- 1981-09-01 SE SE8105173A patent/SE8105173L/ not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3134047A1 (de) | 1982-04-29 |
| DE3134047C2 (en, 2012) | 1989-12-07 |
| IT1138182B (it) | 1986-09-17 |
| SE8105173L (sv) | 1982-03-03 |
| BE890170A (fr) | 1982-03-01 |
| JPS5781423A (en) | 1982-05-21 |
| JPH0341451B2 (en, 2012) | 1991-06-24 |
| MX157218A (es) | 1988-11-04 |
| BR8105592A (pt) | 1982-05-18 |
| BE890171A (fr) | 1982-03-01 |
| GB2083038B (en) | 1984-08-15 |
| FR2489307B1 (fr) | 1987-01-09 |
| NL8104053A (nl) | 1982-04-01 |
| US4337371A (en) | 1982-06-29 |
| ZA816055B (en) | 1983-04-27 |
| GB2083038A (en) | 1982-03-17 |
| IT8123719A0 (it) | 1981-09-01 |
| ES8502071A1 (es) | 1984-12-16 |
| PT73574B (en) | 1982-11-09 |
| JPS5781422A (en) | 1982-05-21 |
| ES505102A0 (es) | 1984-12-16 |
| ZA816056B (en) | 1983-04-27 |
| FR2489307A1 (fr) | 1982-03-05 |
| PT73574A (en) | 1981-09-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |