CA1105059A - Procede d'obtention de polyols a partir d'acetals cycliques - Google Patents
Procede d'obtention de polyols a partir d'acetals cycliquesInfo
- Publication number
- CA1105059A CA1105059A CA293,719A CA293719A CA1105059A CA 1105059 A CA1105059 A CA 1105059A CA 293719 A CA293719 A CA 293719A CA 1105059 A CA1105059 A CA 1105059A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- nickel
- dioxane
- granular
- butanediol
- 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
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 title claims abstract 9
- -1 cyclic acetal Chemical class 0.000 title claims abstract 8
- 238000004519 manufacturing process Methods 0.000 title 1
- 229920005862 polyol Polymers 0.000 title 1
- 150000003077 polyols Chemical class 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract 19
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims abstract 12
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract 11
- 239000003054 catalyst Substances 0.000 claims abstract 9
- 230000007062 hydrolysis Effects 0.000 claims abstract 3
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract 3
- 239000011260 aqueous acid Substances 0.000 claims abstract 2
- 150000002009 diols Chemical class 0.000 claims abstract 2
- 229910052702 rhenium Inorganic materials 0.000 claims abstract 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 26
- 229910052759 nickel Inorganic materials 0.000 claims 10
- 239000007868 Raney catalyst Substances 0.000 claims 8
- 229910000564 Raney nickel Inorganic materials 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 7
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 6
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 6
- 239000010953 base metal Substances 0.000 claims 6
- 229910052804 chromium Inorganic materials 0.000 claims 6
- 239000011651 chromium Substances 0.000 claims 6
- 229910052750 molybdenum Inorganic materials 0.000 claims 6
- 239000011733 molybdenum Substances 0.000 claims 6
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 claims 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- 239000006227 byproduct Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/60—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in six-membered rings
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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75512276A | 1976-12-28 | 1976-12-28 | |
| US755,122 | 1976-12-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1105059A true CA1105059A (fr) | 1981-07-14 |
Family
ID=25037816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA293,719A Expired CA1105059A (fr) | 1976-12-28 | 1977-12-22 | Procede d'obtention de polyols a partir d'acetals cycliques |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5382712A (fr) |
| BE (1) | BE862367A (fr) |
| CA (1) | CA1105059A (fr) |
| DE (1) | DE2758500A1 (fr) |
| FR (1) | FR2376106A1 (fr) |
| GB (1) | GB1581379A (fr) |
| IT (1) | IT1089990B (fr) |
| NL (1) | NL7714433A (fr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4296739B2 (ja) | 2001-03-22 | 2009-07-15 | 昭和電工株式会社 | 両末端ジオール類製造用触媒、該触媒の製造方法、該触媒を用いた両末端ジオール類の製造方法及び該製造方法で得られた両末端ジオール類 |
| WO2006116193A1 (fr) | 2005-04-21 | 2006-11-02 | Shell Internationale Research Maatschappij B.V. | Catalyseur d'hydrogenation est procede d'hydrogenation |
| US7381852B2 (en) | 2006-04-13 | 2008-06-03 | Shell Oil Company | Process for hydrogenating an aldehyde |
| US7943792B2 (en) | 2007-04-02 | 2011-05-17 | Inventure Chemical Inc. | Production of biodiesel, cellulosic sugars, and peptides from the simultaneous esterification and alcoholysis/hydrolysis of materials with oil-containing substituents including phospholipids and peptidic content |
| US8212062B2 (en) | 2007-04-02 | 2012-07-03 | Inventure Chemical, Inc. | Production of biodiesel, cellulosic sugars, and peptides from the simultaneous esterification and alcoholysis/hydrolysis of oil-containing materials with cellulosic and peptidic content |
| US7777085B2 (en) | 2008-10-01 | 2010-08-17 | Inventure Chemical, Inc. | Method for conversion of oil-containing algae to 1,3-propanediol |
| DE102011118956A1 (de) * | 2011-11-19 | 2013-05-23 | Oxea Gmbh | Verfahren zur Gewinnung von Di-Trimethylolpropan und mit Trimethylolpropan angereicherten Produktströmen aus den Nebenströmen der Trimethylolpropanherstellung |
| CN110621663A (zh) | 2017-06-13 | 2019-12-27 | 巴斯夫欧洲公司 | 制备1,6-己二醇衍生物的加氢甲酰基化方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE626845A (fr) * | ||||
| FR1030806A (fr) * | 1950-01-19 | 1953-06-17 | British Ind Solvents Ltd | Procédé d'hydrogénation |
| US2618663A (en) * | 1951-01-17 | 1952-11-18 | Gen Aniline & Film Corp | Production of polyether alcohols |
| US2888492A (en) * | 1955-08-08 | 1959-05-26 | Shell Dev | Production of polyols |
| US3168579A (en) * | 1960-10-14 | 1965-02-02 | Shell Oil Co | Production of polyols from substituted aldehydes |
| GB966270A (en) * | 1961-09-27 | 1964-08-06 | Shell Int Research | Process for the production of polyols |
| DE2401553C2 (de) * | 1974-01-14 | 1984-05-03 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Butandiol-1,4 |
| US3929915A (en) * | 1974-07-31 | 1975-12-30 | Du Pont | Process for the production of butanediol |
| US3963755A (en) * | 1974-07-31 | 1976-06-15 | E. I. Du Pont De Nemours And Company | Mixture of 2(2'-propanal)-5-methyl-1,3-dioxane and 2(3'-propanal)-5-methyl-1,3-dioxane |
| FR2351935A1 (fr) * | 1974-07-31 | 1977-12-16 | Du Pont | Preparation d'acetals a partir d'aldehydes et d'alcools et/ou de diols |
| DE2524039A1 (de) * | 1974-08-02 | 1976-02-19 | Du Pont | Verfahren zum hydrolysieren und hydrieren von acetalaldehyden |
| DE2523840A1 (de) * | 1974-08-02 | 1976-02-12 | Du Pont | Einstufiges verfahren zum hydrolysieren und hydrieren von acetalaldehyden |
-
1977
- 1977-12-19 GB GB5274977A patent/GB1581379A/en not_active Expired
- 1977-12-22 CA CA293,719A patent/CA1105059A/fr not_active Expired
- 1977-12-27 IT IT3130977A patent/IT1089990B/it active
- 1977-12-27 NL NL7714433A patent/NL7714433A/xx not_active Application Discontinuation
- 1977-12-27 FR FR7739277A patent/FR2376106A1/fr active Granted
- 1977-12-27 JP JP15662177A patent/JPS5382712A/ja active Pending
- 1977-12-27 BE BE183886A patent/BE862367A/fr not_active IP Right Cessation
- 1977-12-28 DE DE19772758500 patent/DE2758500A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB1581379A (en) | 1980-12-10 |
| DE2758500A1 (de) | 1978-06-29 |
| NL7714433A (nl) | 1978-06-30 |
| JPS5382712A (en) | 1978-07-21 |
| BE862367A (fr) | 1978-06-27 |
| FR2376106B1 (fr) | 1983-11-18 |
| FR2376106A1 (fr) | 1978-07-28 |
| IT1089990B (it) | 1985-06-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |