CA1312095C - Continuous process for producing 1,2-diols - Google Patents
Continuous process for producing 1,2-diolsInfo
- Publication number
- CA1312095C CA1312095C CA000545071A CA545071A CA1312095C CA 1312095 C CA1312095 C CA 1312095C CA 000545071 A CA000545071 A CA 000545071A CA 545071 A CA545071 A CA 545071A CA 1312095 C CA1312095 C CA 1312095C
- Authority
- CA
- Canada
- Prior art keywords
- column
- water
- epoxide
- solubilizing agent
- set forth
- 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 - Lifetime
Links
- 150000000180 1,2-diols Chemical class 0.000 title claims abstract 3
- 238000010924 continuous production Methods 0.000 title abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000007127 saponification reaction Methods 0.000 claims abstract description 15
- 239000003377 acid catalyst Substances 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 5
- 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 11
- 238000000034 method Methods 0.000 claims description 24
- 150000002009 diols Chemical class 0.000 claims description 16
- 238000009835 boiling Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical group OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000011149 sulphuric acid Nutrition 0.000 claims description 3
- 239000001117 sulphuric acid Substances 0.000 claims description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims 11
- 230000002378 acidificating effect Effects 0.000 claims 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 238000011437 continuous method Methods 0.000 claims 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 150000003509 tertiary alcohols Chemical class 0.000 claims 1
- 230000003381 solubilizing effect Effects 0.000 abstract description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000002924 oxiranes Chemical class 0.000 description 18
- 239000011260 aqueous acid Substances 0.000 description 5
- 230000000875 corresponding effect Effects 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N methyl heptene Natural products CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 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
- 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
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 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
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002576 ketones Chemical class 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
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000004064 recycling Methods 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
- -1 tertiary amine salts Chemical class 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)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863628674 DE3628674A1 (de) | 1986-08-23 | 1986-08-23 | Kontinuierliches verfahren zur herstellung von 1,2-diolen |
| DEP3628674.5-42 | 1986-08-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1312095C true CA1312095C (en) | 1992-12-29 |
Family
ID=6308041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000545071A Expired - Lifetime CA1312095C (en) | 1986-08-23 | 1987-08-21 | Continuous process for producing 1,2-diols |
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) |
Families Citing this family (9)
| 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 |
| JP4045774B2 (ja) * | 2000-10-27 | 2008-02-13 | 住友化学株式会社 | カルボン酸類の製造法とその触媒 |
| 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 |
| DE102005009133B4 (de) * | 2005-03-01 | 2007-02-08 | Clariant Produkte (Deutschland) Gmbh | Verfahren zur Herstellung von Alkylenglykolen |
| 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 |
Family Cites Families (9)
| 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 |
| DE2256907C3 (de) * | 1972-11-20 | 1982-03-18 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur Herstellung von vicinalen Di- und Polyolen |
| 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 |
| DE3442938C2 (de) * | 1984-11-24 | 1986-11-06 | Degussa Ag, 6000 Frankfurt | Verfahren zur kontinuierlichen Herstellung vicinaler Diole |
| 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 AT AT87110975T patent/ATE57907T1/de not_active IP Right Cessation
- 1987-07-29 DE DE8787110975T patent/DE3765883D1/de not_active Expired - Lifetime
- 1987-07-29 EP EP87110975A patent/EP0257332B1/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
Also Published As
| Publication number | Publication date |
|---|---|
| DE3628674A1 (de) | 1988-02-25 |
| ATE57907T1 (de) | 1990-11-15 |
| US4762954A (en) | 1988-08-09 |
| JP2585618B2 (ja) | 1997-02-26 |
| EP0257332A1 (de) | 1988-03-02 |
| JPS6357542A (ja) | 1988-03-12 |
| EP0257332B1 (de) | 1990-10-31 |
| DE3765883D1 (de) | 1990-12-06 |
| DE3628674C2 (enExample) | 1988-07-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |