NO845279L - Fremgangsmaate for fremstilling av alkylenglykoler. - Google Patents
Fremgangsmaate for fremstilling av alkylenglykoler.Info
- Publication number
- NO845279L NO845279L NO845279A NO845279A NO845279L NO 845279 L NO845279 L NO 845279L NO 845279 A NO845279 A NO 845279A NO 845279 A NO845279 A NO 845279A NO 845279 L NO845279 L NO 845279L
- Authority
- NO
- Norway
- Prior art keywords
- formaldehyde
- secondary alcohol
- methanol
- weight
- peroxide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 30
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 82
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 39
- 150000001451 organic peroxides Chemical class 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 150000003333 secondary alcohols Chemical class 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 11
- -1 alkylene glycol Chemical compound 0.000 claims description 8
- 230000005670 electromagnetic radiation Effects 0.000 claims description 8
- 239000000376 reactant Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 5
- WFRBDWRZVBPBDO-UHFFFAOYSA-N 2-methyl-2-pentanol Chemical compound CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 claims description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 4
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 claims description 4
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 claims description 4
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 claims description 4
- 230000005855 radiation Effects 0.000 claims description 4
- IKECULIHBUCAKR-UHFFFAOYSA-N 2,3-dimethylbutan-2-ol Chemical compound CC(C)C(C)(C)O IKECULIHBUCAKR-UHFFFAOYSA-N 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- QCRFMSUKWRQZEM-UHFFFAOYSA-N cycloheptanol Chemical compound OC1CCCCCC1 QCRFMSUKWRQZEM-UHFFFAOYSA-N 0.000 claims description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 2
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 claims description 2
- 235000019256 formaldehyde Nutrition 0.000 description 22
- 238000004519 manufacturing process Methods 0.000 description 9
- 229920002866 paraformaldehyde Polymers 0.000 description 9
- 229930040373 Paraformaldehyde Natural products 0.000 description 8
- 150000002978 peroxides Chemical class 0.000 description 8
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 4
- KQBSGRWMSNFIPG-UHFFFAOYSA-N trioxane Chemical compound C1COOOC1 KQBSGRWMSNFIPG-UHFFFAOYSA-N 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 239000012969 di-tertiary-butyl peroxide Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- UYVWNPAMKCDKRB-UHFFFAOYSA-N 1,2,4,5-tetraoxane Chemical compound C1OOCOO1 UYVWNPAMKCDKRB-UHFFFAOYSA-N 0.000 description 2
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 229920006324 polyoxymethylene Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical group CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- OORRCVPWRPVJEK-UHFFFAOYSA-N 2-oxidanylethanoic acid Chemical compound OCC(O)=O.OCC(O)=O OORRCVPWRPVJEK-UHFFFAOYSA-N 0.000 description 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 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 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
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000011551 heat transfer agent Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000003079 shale oil Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000008247 solid mixture 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
- 239000013638 trimer Substances 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
- C07C29/38—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 by reaction with aldehydes or ketones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838334611A GB8334611D0 (en) | 1983-12-30 | 1983-12-30 | Production of alkylene glycols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO845279L true NO845279L (no) | 1985-07-01 |
Family
ID=10553923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO845279A NO845279L (no) | 1983-12-30 | 1984-12-28 | Fremgangsmaate for fremstilling av alkylenglykoler. |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4571289A (xx) |
| EP (1) | EP0147983A3 (xx) |
| JP (1) | JPS60172940A (xx) |
| AU (1) | AU3703084A (xx) |
| GB (1) | GB8334611D0 (xx) |
| NO (1) | NO845279L (xx) |
| ZA (1) | ZA849981B (xx) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4023255A1 (de) * | 1990-07-21 | 1992-01-23 | Basf Ag | Verfahren zur herstellung von glykolen, insbesondere propylenglykol aus formaldehyd |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4412084A (en) * | 1981-07-28 | 1983-10-25 | John Kollar | Process for producing ethylene glycol |
| JPS6019896B2 (ja) * | 1982-03-09 | 1985-05-18 | 工業技術院長 | エチレングリコ−ルの製造方法 |
-
1983
- 1983-12-30 GB GB838334611A patent/GB8334611D0/en active Pending
-
1984
- 1984-12-13 EP EP84308671A patent/EP0147983A3/en not_active Withdrawn
- 1984-12-13 US US06/681,006 patent/US4571289A/en not_active Expired - Fee Related
- 1984-12-21 ZA ZA849981A patent/ZA849981B/xx unknown
- 1984-12-21 AU AU37030/84A patent/AU3703084A/en not_active Abandoned
- 1984-12-28 NO NO845279A patent/NO845279L/no unknown
-
1985
- 1985-01-04 JP JP60000104A patent/JPS60172940A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0147983A3 (en) | 1986-06-25 |
| US4571289A (en) | 1986-02-18 |
| GB8334611D0 (en) | 1984-02-08 |
| AU3703084A (en) | 1985-07-04 |
| JPS60172940A (ja) | 1985-09-06 |
| EP0147983A2 (en) | 1985-07-10 |
| ZA849981B (en) | 1986-08-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2915529A (en) | Method for preparing glycerin carbonate | |
| US2925424A (en) | Fluoroketals and their preparation | |
| US2841624A (en) | Process for producing alkylated phenols | |
| US5177265A (en) | Process for the preparation of citral | |
| US4933500A (en) | Process for the preparation of citral | |
| FR2489307A1 (fr) | Procede de fabrication d'ethylene glycol | |
| NO845279L (no) | Fremgangsmaate for fremstilling av alkylenglykoler. | |
| Sanderson et al. | Free radicals in organic synthesis. A novel synthesis of glycerol based on ethylene glycol and formaldehyde | |
| US3607885A (en) | Preparation of lactones such as substituted delta valerolactones | |
| US3976700A (en) | Process for preparing methyl heptenone | |
| US4533774A (en) | Process for the production of ethylene glycol | |
| US3506722A (en) | Di(hydroxymethyl)methyl-cyclopentanes | |
| US2541747A (en) | Production of hydroxyl compounds by hydrolysis of tetrahydropyryl ethers | |
| EP0147133B1 (en) | Process for the production of alkylene glycols from secondary alcohols | |
| US2878265A (en) | Production of methylenedioxyphenyl derivatives | |
| EP1028952B1 (en) | Vinyl ether derivatives | |
| Ouchi et al. | Coal hydrogenolysis in the presence of NaOH | |
| US4602102A (en) | Production of alkyl glycolates | |
| US2105828A (en) | Production of morpholine ethanols | |
| US2792421A (en) | Condensation reaction | |
| US3140297A (en) | Production of cyclic acetals and ketals | |
| US4550184A (en) | Production of 2-hydroxymethyl-1,3-dioxolane | |
| CA1097360A (en) | Process for the preparation of 4-benzoyl-4 phenyldioxolane | |
| SU318293A1 (ru) | Способ получени третичных ацетиленовых спиртов | |
| CA1057775A (en) | Process for preparing methyl heptenone |