DE3442938C2 - Verfahren zur kontinuierlichen Herstellung vicinaler Diole - Google Patents
Verfahren zur kontinuierlichen Herstellung vicinaler DioleInfo
- Publication number
- DE3442938C2 DE3442938C2 DE3442938A DE3442938A DE3442938C2 DE 3442938 C2 DE3442938 C2 DE 3442938C2 DE 3442938 A DE3442938 A DE 3442938A DE 3442938 A DE3442938 A DE 3442938A DE 3442938 C2 DE3442938 C2 DE 3442938C2
- Authority
- DE
- Germany
- Prior art keywords
- oxide
- water
- epoxides
- solvent
- saponification
- 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
- 150000002009 diols Chemical group 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims description 18
- 238000010924 continuous production Methods 0.000 title claims description 5
- 238000007127 saponification reaction Methods 0.000 claims abstract description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- -1 cyclic epoxides Chemical class 0.000 claims abstract description 8
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 21
- 239000004593 Epoxy Substances 0.000 claims description 9
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 claims description 7
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 150000008282 halocarbons Chemical class 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims 3
- 239000002253 acid Substances 0.000 abstract description 7
- 150000005826 halohydrocarbons Chemical class 0.000 abstract 1
- 150000002924 oxiranes Chemical class 0.000 description 23
- 239000000243 solution Substances 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- PKXHXOTZMFCXSH-UHFFFAOYSA-N 3,3-dimethylbut-1-ene Chemical compound CC(C)(C)C=C PKXHXOTZMFCXSH-UHFFFAOYSA-N 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 4
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 3
- BCJPEZMFAKOJPM-UHFFFAOYSA-N 2-ethyl-3-methyloxirane Chemical compound CCC1OC1C BCJPEZMFAKOJPM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical class CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
- 229940031723 1,2-octanediol Drugs 0.000 description 1
- LFKLPJRVSHJZPL-UHFFFAOYSA-N 1,2:7,8-diepoxyoctane Chemical compound C1OC1CCCCC1CO1 LFKLPJRVSHJZPL-UHFFFAOYSA-N 0.000 description 1
- QPBYBLZYMNWGMO-UHFFFAOYSA-N 2,2,3-trimethyloxirane Chemical compound CC1OC1(C)C QPBYBLZYMNWGMO-UHFFFAOYSA-N 0.000 description 1
- PCGTXZMDZGOMJG-UHFFFAOYSA-N 2,3-diethyloxirane Chemical compound CCC1OC1CC PCGTXZMDZGOMJG-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- QZXUQPKFNQQQAJ-UHFFFAOYSA-N 2-ethyl-2-methyloxirane Chemical compound CCC1(C)CO1 QZXUQPKFNQQQAJ-UHFFFAOYSA-N 0.000 description 1
- ZNAFWUJVHGNGIF-UHFFFAOYSA-N 2-ethyl-3-propyloxirane Chemical compound CCCC1OC1CC ZNAFWUJVHGNGIF-UHFFFAOYSA-N 0.000 description 1
- LIESJAYIOKBLIL-UHFFFAOYSA-N 2-methyl-3-propyloxirane Chemical compound CCCC1OC1C LIESJAYIOKBLIL-UHFFFAOYSA-N 0.000 description 1
- NMOFYYYCFRVWBK-UHFFFAOYSA-N 2-pentyloxirane Chemical class CCCCCC1CO1 NMOFYYYCFRVWBK-UHFFFAOYSA-N 0.000 description 1
- REYZXWIIUPKFTI-UHFFFAOYSA-N 2-propan-2-yloxirane Chemical compound CC(C)C1CO1 REYZXWIIUPKFTI-UHFFFAOYSA-N 0.000 description 1
- SYURNNNQIFDVCA-UHFFFAOYSA-N 2-propyloxirane Chemical class CCCC1CO1 SYURNNNQIFDVCA-UHFFFAOYSA-N 0.000 description 1
- ZQDPJFUHLCOCRG-UHFFFAOYSA-N 3-hexene Chemical compound CCC=CCC ZQDPJFUHLCOCRG-UHFFFAOYSA-N 0.000 description 1
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- XAYDWGMOPRHLEP-UHFFFAOYSA-N 6-ethenyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCCC2OC21C=C XAYDWGMOPRHLEP-UHFFFAOYSA-N 0.000 description 1
- GJEZBVHHZQAEDB-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hexane Chemical compound C1CCC2OC21 GJEZBVHHZQAEDB-UHFFFAOYSA-N 0.000 description 1
- MLOZFLXCWGERSM-UHFFFAOYSA-N 8-oxabicyclo[5.1.0]octane Chemical compound C1CCCCC2OC21 MLOZFLXCWGERSM-UHFFFAOYSA-N 0.000 description 1
- FHRVMGIEUUPKQO-UHFFFAOYSA-N 9-oxabicyclo[6.1.0]nonan-6-ol Chemical compound C1C(O)CCCCC2OC21 FHRVMGIEUUPKQO-UHFFFAOYSA-N 0.000 description 1
- MELPJGOMEMRMPL-UHFFFAOYSA-N 9-oxabicyclo[6.1.0]nonane Chemical compound C1CCCCCC2OC21 MELPJGOMEMRMPL-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- VEFXTGTZJOWDOF-UHFFFAOYSA-N benzene;hydrate Chemical compound O.C1=CC=CC=C1 VEFXTGTZJOWDOF-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical compound CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- GWHJZXXIDMPWGX-UHFFFAOYSA-N pseudo-cymene Natural products CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000004448 titration Methods 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
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
- C07C29/103—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers
- C07C29/106—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers of oxiranes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3442938A DE3442938C2 (de) | 1984-11-24 | 1984-11-24 | Verfahren zur kontinuierlichen Herstellung vicinaler Diole |
| DE8585113046T DE3568422D1 (en) | 1984-11-24 | 1985-10-15 | Process for the continuous preparation of vicinal diols |
| EP85113046A EP0183028B1 (de) | 1984-11-24 | 1985-10-15 | Verfahren zur kontinuierlichen Herstellung vicinaler Diole |
| AT85113046T ATE40983T1 (de) | 1984-11-24 | 1985-10-15 | Verfahren zur kontinuierlichen herstellung vicinaler diole. |
| US06/798,797 US4626603A (en) | 1984-11-24 | 1985-11-15 | Process for the continuous production of vicinal diols |
| BE6/48165A BE903691A (fr) | 1984-11-24 | 1985-11-21 | Procede pour la preparation en continu de diols vicinaux. |
| JP60262723A JPS61130248A (ja) | 1984-11-24 | 1985-11-25 | ビシナルの低分子量ジオールの連続的製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3442938A DE3442938C2 (de) | 1984-11-24 | 1984-11-24 | Verfahren zur kontinuierlichen Herstellung vicinaler Diole |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3442938A1 DE3442938A1 (de) | 1986-05-28 |
| DE3442938C2 true DE3442938C2 (de) | 1986-11-06 |
Family
ID=6251090
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3442938A Expired DE3442938C2 (de) | 1984-11-24 | 1984-11-24 | Verfahren zur kontinuierlichen Herstellung vicinaler Diole |
| DE8585113046T Expired DE3568422D1 (en) | 1984-11-24 | 1985-10-15 | Process for the continuous preparation of vicinal diols |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8585113046T Expired DE3568422D1 (en) | 1984-11-24 | 1985-10-15 | Process for the continuous preparation of vicinal diols |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4626603A (https=) |
| EP (1) | EP0183028B1 (https=) |
| JP (1) | JPS61130248A (https=) |
| AT (1) | ATE40983T1 (https=) |
| BE (1) | BE903691A (https=) |
| DE (2) | DE3442938C2 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0226799B1 (en) * | 1985-11-18 | 1992-01-02 | MITSUI TOATSU CHEMICALS, Inc. | Method for preparing ethylene glycol and/or propylene glycol |
| ATE68779T1 (de) * | 1986-08-23 | 1991-11-15 | Degussa | Verfahren zur herstellung vicinaler diole. |
| DE3628674A1 (de) * | 1986-08-23 | 1988-02-25 | Degussa | Kontinuierliches verfahren zur herstellung von 1,2-diolen |
| US5250743A (en) * | 1992-12-31 | 1993-10-05 | Eastman Kodak Company | Method of intercoversion of enantiomers of acyclic 1,2-dihydroxy-3-alkenes |
| ES2125496T3 (es) * | 1993-10-22 | 1999-03-01 | Dow Chemical Co | Alquilenglicoles que tienen un contenido aumentado de hidroxilo primario. |
| US6214888B1 (en) * | 1996-09-18 | 2001-04-10 | Applied Genetics Incorporated | Dermatological compounds |
| DE19949717A1 (de) * | 1999-10-14 | 2001-04-26 | Nopco Paper Technology Holding | Verwendung von Alkandiolen und/oder Alkantriolen |
| NZ515366A (en) * | 2001-11-08 | 2004-07-30 | Univ Waikato | Method for producing vicinal diols of compounds (especially lanosterol and cyclohexane derivatives) by reacting compounds with acids with pKa of less than or equal to 2 in the presence of one or more reagents capable of supplying hydroxy groups |
| JP4592258B2 (ja) * | 2003-05-07 | 2010-12-01 | 出光興産株式会社 | ２−アルキルアルカン−１，２−ジオール類の製造方法 |
| DE102004060541A1 (de) * | 2004-12-15 | 2006-06-29 | Degussa Ag | Verfahren zur Herstellung von Alkandiolen und Alkantriolen mit einer vicinalen Diol-Gruppe |
| JP2010106039A (ja) * | 2010-01-12 | 2010-05-13 | Idemitsu Kosan Co Ltd | ２−アルキルアルカン−１，２−ジオール類の製造方法 |
| JP5685033B2 (ja) * | 2010-09-17 | 2015-03-18 | 住化バイエルウレタン株式会社 | 水を原料としたポリエーテルポリオールの製造方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2784202A (en) * | 1957-03-05 | Liquid phase oxidation of propylene using | ||
| US1641710A (en) * | 1926-06-11 | 1927-09-06 | Frederick H Untiedt | Process of preparing glycols |
| US2236919A (en) * | 1937-12-17 | 1941-04-01 | Shell Dev | Process for the production of polyhydric alcohols and derivatives thereof |
| US2623909A (en) * | 1950-07-12 | 1952-12-30 | Celanese Corp | Hydrolysis of 1, 2-propylene oxide to 1, 2-propylene glycol |
| US3405093A (en) * | 1966-12-05 | 1968-10-08 | Dow Chemical Co | Process for hydrolyzing polyepoxide resins |
| US3576890A (en) * | 1968-12-23 | 1971-04-27 | Monsanto Co | Process for the preparation of alkylene glycols |
| DE2256907C3 (de) * | 1972-11-20 | 1982-03-18 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur Herstellung von vicinalen Di- und Polyolen |
| US3991126A (en) * | 1975-09-11 | 1976-11-09 | Chevron Research Company | Hydroxylation of unsaturated diols to prepare novel tetraols |
| US4087474A (en) * | 1977-06-06 | 1978-05-02 | Continental Oil Company | Process for the purification of 1,2-dichloroethane |
| US4107221A (en) * | 1977-07-28 | 1978-08-15 | The Dow Chemical Company | Removal of olefin oxide from chlorinated solvents |
| DE2938154A1 (de) * | 1979-09-21 | 1981-04-09 | Degussa Ag, 6000 Frankfurt | Verfahren zur herstellung von 1,2-diolen hoeherer kohlenstoffzahl |
| EP0043192A1 (en) * | 1980-06-26 | 1982-01-06 | Imperial Chemical Industries Plc | Process for the oxidation of olefinic compounds to olefine oxides or derivatives thereof |
| JPS6041646B2 (ja) * | 1980-10-02 | 1985-09-18 | 日本パ−オキサイド株式会社 | 高純度１，２−アルカングリコ−ル製造法 |
-
1984
- 1984-11-24 DE DE3442938A patent/DE3442938C2/de not_active Expired
-
1985
- 1985-10-15 AT AT85113046T patent/ATE40983T1/de not_active IP Right Cessation
- 1985-10-15 DE DE8585113046T patent/DE3568422D1/de not_active Expired
- 1985-10-15 EP EP85113046A patent/EP0183028B1/de not_active Expired
- 1985-11-15 US US06/798,797 patent/US4626603A/en not_active Expired - Lifetime
- 1985-11-21 BE BE6/48165A patent/BE903691A/fr not_active IP Right Cessation
- 1985-11-25 JP JP60262723A patent/JPS61130248A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3442938A1 (de) | 1986-05-28 |
| JPS61130248A (ja) | 1986-06-18 |
| EP0183028A3 (en) | 1987-08-05 |
| EP0183028B1 (de) | 1989-03-01 |
| ATE40983T1 (de) | 1989-03-15 |
| BE903691A (fr) | 1986-05-21 |
| EP0183028A2 (de) | 1986-06-04 |
| DE3568422D1 (en) | 1989-04-06 |
| JPH0564934B2 (https=) | 1993-09-16 |
| US4626603A (en) | 1986-12-02 |
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