DE3628674A1 - Kontinuierliches verfahren zur herstellung von 1,2-diolen - Google Patents
Kontinuierliches verfahren zur herstellung von 1,2-diolenInfo
- Publication number
- DE3628674A1 DE3628674A1 DE19863628674 DE3628674A DE3628674A1 DE 3628674 A1 DE3628674 A1 DE 3628674A1 DE 19863628674 DE19863628674 DE 19863628674 DE 3628674 A DE3628674 A DE 3628674A DE 3628674 A1 DE3628674 A1 DE 3628674A1
- Authority
- DE
- Germany
- Prior art keywords
- column
- solubilizer
- water
- epoxy
- 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.)
- Granted
Links
- 238000010924 continuous production Methods 0.000 title claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000007127 saponification reaction Methods 0.000 claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 230000002378 acidificating effect Effects 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 6
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 239000007788 liquid Substances 0.000 claims abstract description 4
- 150000002118 epoxides Chemical class 0.000 claims abstract 5
- 150000000180 1,2-diols Chemical class 0.000 claims abstract 2
- 150000002009 diols Chemical class 0.000 claims description 16
- 239000004593 Epoxy Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- 238000009835 boiling Methods 0.000 claims description 12
- 239000003377 acid catalyst Substances 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 5
- 239000012071 phase Substances 0.000 claims description 5
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- 239000011260 aqueous acid Substances 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 150000003509 tertiary alcohols Chemical class 0.000 claims 1
- 150000002924 oxiranes Chemical class 0.000 description 9
- 239000002253 acid Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- -1 tertiary Amine salts Chemical class 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- YKNKDKHJZIUQBL-TWTPFVCWSA-N bartanol Chemical compound CC1C\C=C\C(=O)OC(C)CC(CO)\C=C\C(=O)O1 YKNKDKHJZIUQBL-TWTPFVCWSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 238000009529 body temperature measurement Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000012856 packing Methods 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
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002699 waste material 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
- C07C29/09—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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Epoxy Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863628674 DE3628674A1 (de) | 1986-08-23 | 1986-08-23 | Kontinuierliches verfahren zur herstellung von 1,2-diolen |
| EP87110975A EP0257332B1 (de) | 1986-08-23 | 1987-07-29 | Kontinuierliches Verfahren zur Herstellung von 1,2-Diolen |
| DE8787110975T DE3765883D1 (de) | 1986-08-23 | 1987-07-29 | Kontinuierliches verfahren zur herstellung von 1,2-diolen. |
| AT87110975T ATE57907T1 (de) | 1986-08-23 | 1987-07-29 | Kontinuierliches verfahren zur herstellung von 1,2-diolen. |
| US07/082,516 US4762954A (en) | 1986-08-23 | 1987-08-07 | Continuous method for the production of 1,2-diols |
| CA000545071A CA1312095C (en) | 1986-08-23 | 1987-08-21 | Continuous process for producing 1,2-diols |
| JP62206637A JP2585618B2 (ja) | 1986-08-23 | 1987-08-21 | 高い炭素原子数の１，２−ジオ−ルの連続的製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863628674 DE3628674A1 (de) | 1986-08-23 | 1986-08-23 | Kontinuierliches verfahren zur herstellung von 1,2-diolen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3628674A1 true DE3628674A1 (de) | 1988-02-25 |
| DE3628674C2 DE3628674C2 (enExample) | 1988-07-28 |
Family
ID=6308041
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19863628674 Granted DE3628674A1 (de) | 1986-08-23 | 1986-08-23 | Kontinuierliches verfahren zur herstellung von 1,2-diolen |
| DE8787110975T Expired - Lifetime DE3765883D1 (de) | 1986-08-23 | 1987-07-29 | Kontinuierliches verfahren zur herstellung von 1,2-diolen. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8787110975T Expired - Lifetime DE3765883D1 (de) | 1986-08-23 | 1987-07-29 | Kontinuierliches verfahren zur herstellung von 1,2-diolen. |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4762954A (enExample) |
| EP (1) | EP0257332B1 (enExample) |
| JP (1) | JP2585618B2 (enExample) |
| AT (1) | ATE57907T1 (enExample) |
| CA (1) | CA1312095C (enExample) |
| DE (2) | DE3628674A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005009133A1 (de) * | 2005-03-01 | 2006-09-07 | Clariant Produkte (Deutschland) Gmbh | Verfahren zur Herstellung von Alkylenglykolen |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4960754A (en) * | 1987-01-09 | 1990-10-02 | International Flavors & Fragrances Inc. | 3,7-dimethyl-6,7-dioxo-1,3-octadiene derivatives and organoleptic uses thereof |
| DE4115146A1 (de) * | 1991-05-08 | 1992-11-12 | Henkel Kgaa | Verfahren zur herstellung von epoxid-ringoeffnungsprodukten mit einem definierten rest-epoxidsauerstoffgehalt |
| JP4013522B2 (ja) * | 2000-10-27 | 2007-11-28 | 住友化学株式会社 | β−ヒドロキシヒドロペルオキシド類またはカルボン酸類の製造方法とその触媒 |
| 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 |
| US20080227993A1 (en) * | 2007-03-17 | 2008-09-18 | Matthew Mark Zuckerman | Synthesizing and compounding molecules from and with plant oils to improve low temperature behavior of plant oils as fuels, oils and lubricants |
| 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 |
| CN111718236B (zh) * | 2020-07-10 | 2022-04-19 | 万华化学集团股份有限公司 | 一种脂肪族二元醇的制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2256907A1 (de) * | 1972-11-20 | 1974-05-22 | Henkel & Cie Gmbh | Verfahren zur herstellung von vicinalen glykolen |
| DE3442938A1 (de) * | 1984-11-24 | 1986-05-28 | Degussa Ag, 6000 Frankfurt | Verfahren zur kontinuierlichen herstellung vicinaler diole |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2650940A (en) * | 1953-09-01 | Manufacture of glycols | ||
| US2686817A (en) * | 1951-01-02 | 1954-08-17 | Gen Aniline & Film Corp | Production of 1, 4-butanediol from tetrahydrofuran |
| US3576890A (en) * | 1968-12-23 | 1971-04-27 | Monsanto Co | Process for the preparation of alkylene glycols |
| CA1133522A (en) * | 1978-06-20 | 1982-10-12 | Glenn A. Taylor | Process for hydrolyzing alkylene oxides to alkylene glycols |
| DE2931753C2 (de) * | 1979-08-04 | 1984-10-04 | Akzo Gmbh, 5600 Wuppertal | Verfahren zur Herstellung von vicinalen Alkylenglykolen |
| 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 |
| DE3442937C2 (de) * | 1984-11-24 | 1986-11-06 | Degussa Ag, 6000 Frankfurt | Verfahren zur kontinuierlichen Herstellung von 1,2-Pentandiol |
-
1986
- 1986-08-23 DE DE19863628674 patent/DE3628674A1/de active Granted
-
1987
- 1987-07-29 EP EP87110975A patent/EP0257332B1/de not_active Expired - Lifetime
- 1987-07-29 AT AT87110975T patent/ATE57907T1/de not_active IP Right Cessation
- 1987-07-29 DE DE8787110975T patent/DE3765883D1/de not_active Expired - Lifetime
- 1987-08-07 US US07/082,516 patent/US4762954A/en not_active Expired - Lifetime
- 1987-08-21 CA CA000545071A patent/CA1312095C/en not_active Expired - Lifetime
- 1987-08-21 JP JP62206637A patent/JP2585618B2/ja not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2256907A1 (de) * | 1972-11-20 | 1974-05-22 | Henkel & Cie Gmbh | Verfahren zur herstellung von vicinalen glykolen |
| DE3442938A1 (de) * | 1984-11-24 | 1986-05-28 | Degussa Ag, 6000 Frankfurt | Verfahren zur kontinuierlichen herstellung vicinaler diole |
Non-Patent Citations (1)
| Title |
|---|
| HOUBEN-WEYL: Methoden der organischen Chemie, Bd. VI/1a, Teil 1, 1979, S. 357 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005009133A1 (de) * | 2005-03-01 | 2006-09-07 | Clariant Produkte (Deutschland) Gmbh | Verfahren zur Herstellung von Alkylenglykolen |
| DE102005009133B4 (de) * | 2005-03-01 | 2007-02-08 | Clariant Produkte (Deutschland) Gmbh | Verfahren zur Herstellung von Alkylenglykolen |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2585618B2 (ja) | 1997-02-26 |
| DE3765883D1 (de) | 1990-12-06 |
| US4762954A (en) | 1988-08-09 |
| EP0257332A1 (de) | 1988-03-02 |
| DE3628674C2 (enExample) | 1988-07-28 |
| EP0257332B1 (de) | 1990-10-31 |
| CA1312095C (en) | 1992-12-29 |
| JPS6357542A (ja) | 1988-03-12 |
| ATE57907T1 (de) | 1990-11-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |