DE2054601C3 - Verfahren zur Herstellung von zweiwertigen Alkoholen - Google Patents
Verfahren zur Herstellung von zweiwertigen AlkoholenInfo
- Publication number
- DE2054601C3 DE2054601C3 DE2054601A DE2054601A DE2054601C3 DE 2054601 C3 DE2054601 C3 DE 2054601C3 DE 2054601 A DE2054601 A DE 2054601A DE 2054601 A DE2054601 A DE 2054601A DE 2054601 C3 DE2054601 C3 DE 2054601C3
- Authority
- DE
- Germany
- Prior art keywords
- hydrogenation
- oxyaldehyde
- oxyaldehydes
- carbon atoms
- alcohols
- 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
- 238000000034 method Methods 0.000 title claims description 10
- 150000001298 alcohols Chemical class 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000002894 organic compounds Chemical class 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000003333 secondary alcohols Chemical class 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 15
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
- JJMOMMLADQPZNY-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanal Chemical compound OCC(C)(C)C=O JJMOMMLADQPZNY-UHFFFAOYSA-N 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000005882 aldol condensation reaction Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- BSABBBMNWQWLLU-UHFFFAOYSA-N hydroxypropionaldehyde Natural products CC(O)C=O BSABBBMNWQWLLU-UHFFFAOYSA-N 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 239000003513 alkali Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- SZCWBURCISJFEZ-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) 3-hydroxy-2,2-dimethylpropanoate Chemical compound OCC(C)(C)COC(=O)C(C)(C)CO SZCWBURCISJFEZ-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000011144 upstream manufacturing 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
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
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)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2054601A DE2054601C3 (de) | 1970-11-06 | 1970-11-06 | Verfahren zur Herstellung von zweiwertigen Alkoholen |
| RO7100068545A RO63376A (fr) | 1970-11-06 | 1971-10-22 | Procede pour la preparation des diols |
| FI3087/71A FI55646C (fi) | 1970-11-06 | 1971-10-28 | Saett att tillverka smaomolekylaera 1,3-dioler |
| GB5047571A GB1363677A (en) | 1970-11-06 | 1971-10-29 | Process for the production of dihydric alcohols |
| FR7139098A FR2113422A5 (enExample) | 1970-11-06 | 1971-10-29 | |
| SE7113807A SE391919B (sv) | 1970-11-06 | 1971-10-29 | Sett for framstellning av tvaverda alkoholer genom katalytisk hydrering av motsvarande oxialdhyder |
| BR7283/71A BR7107283D0 (pt) | 1970-11-06 | 1971-10-29 | Processo para preparacao de alcoois bivolentes |
| AT936671A AT313247B (de) | 1970-11-06 | 1971-10-29 | Verfahren zur Herstellung von zweiwertigen Alkoholen |
| AU35170/71A AU457369B2 (en) | 1970-11-06 | 1971-10-29 | A process forthe preparation of dihydric alcohols |
| IT53820/71A IT942249B (it) | 1970-11-06 | 1971-10-30 | Procedimento per la preparazione di alcoli bivalenti |
| CA126,962A CA948217A (en) | 1970-11-06 | 1971-11-05 | Process for the production of divalent alcohols |
| JP46088636A JPS5118928B1 (enExample) | 1970-11-06 | 1971-11-06 | |
| US05/685,899 US4094914A (en) | 1970-11-06 | 1976-05-12 | Process for the production of divalent alcohols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2054601A DE2054601C3 (de) | 1970-11-06 | 1970-11-06 | Verfahren zur Herstellung von zweiwertigen Alkoholen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2054601A1 DE2054601A1 (de) | 1972-05-10 |
| DE2054601C3 true DE2054601C3 (de) | 1980-02-14 |
Family
ID=5787310
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2054601A Expired DE2054601C3 (de) | 1970-11-06 | 1970-11-06 | Verfahren zur Herstellung von zweiwertigen Alkoholen |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4094914A (enExample) |
| JP (1) | JPS5118928B1 (enExample) |
| AT (1) | AT313247B (enExample) |
| BR (1) | BR7107283D0 (enExample) |
| CA (1) | CA948217A (enExample) |
| DE (1) | DE2054601C3 (enExample) |
| FI (1) | FI55646C (enExample) |
| FR (1) | FR2113422A5 (enExample) |
| GB (1) | GB1363677A (enExample) |
| IT (1) | IT942249B (enExample) |
| RO (1) | RO63376A (enExample) |
| SE (1) | SE391919B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4855515A (en) * | 1987-08-12 | 1989-08-08 | Eastman Kodak Company | Process for the production of neopentyl glycol |
| US4851592A (en) * | 1987-10-27 | 1989-07-25 | Eastman Kodak Company | Triethylamine catalyzed neopentyl glycol production utilizing a gas sparged reactor |
| DE3926136A1 (de) * | 1989-08-08 | 1991-02-14 | Degussa | Verfahren zur herstellung von 1,3-propandiol |
| DE4038192A1 (de) * | 1990-11-30 | 1992-06-04 | Degussa | Verfahren zur herstellung von 1,3-propandiol |
| US5532417A (en) * | 1991-04-26 | 1996-07-02 | Aristech Chemical Corporation | Manufacture of neopentyl glycol (IV) |
| US5146012A (en) * | 1991-04-26 | 1992-09-08 | Aristech Chemical Corporation | Manufacture of neopentyl glycol (III) |
| JPH05201898A (ja) * | 1991-06-28 | 1993-08-10 | Aristech Chem Corp | ネオペンチルグリコールの製造方法 |
| US5248752A (en) * | 1991-11-12 | 1993-09-28 | Union Carbide Chemicals & Plastics Technology Corporation | Polyurethane (meth)acrylates and processes for preparing same |
| DE4218282A1 (de) * | 1992-06-03 | 1993-12-09 | Degussa | Verfahren zur Herstellung von 1,3-Propandiol |
| EP0614453A4 (en) * | 1992-09-25 | 1994-09-21 | Aristech Chemical Corp | Manufacture of trimethylolpropane. |
| TWI266760B (en) | 2000-03-20 | 2006-11-21 | Kvaerner Process Tech Ltd | Process for the preparation of propane-1,3-diol |
| EP1384709A1 (de) * | 2002-07-26 | 2004-01-28 | Sika Technology AG | Polyaldimine |
| DE102012021276A1 (de) | 2012-10-29 | 2014-04-30 | Oxea Gmbh | Kontinuierliches Verfahren zur Herstellung von Neopentylglykol |
| PL3400208T3 (pl) * | 2016-01-07 | 2021-12-27 | Haldor Topsøe A/S | Sposób wytwarzania glikolu etylenowego z cukrów |
| MX2018007748A (es) * | 2016-01-07 | 2018-11-14 | Topsoe Haldor As | Proceso para la preparacion de etilenglicol a partir de azucares. |
| KR102680195B1 (ko) * | 2020-10-16 | 2024-06-28 | 주식회사 엘지화학 | 네오펜틸 글리콜의 제조방법 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3173959A (en) * | 1965-03-16 | Process for the production of saturated fatty alcohols | ||
| GB309200A (en) * | 1927-09-28 | 1929-03-28 | Ig Farbenindustrie Ag | A process for the manufacture and production of mono- and polyhydric alcohols |
| FR707356A (fr) * | 1929-12-13 | 1931-07-07 | Lonza Ag | Procédé de production de 1:3-butylèneglycol |
| GB348248A (en) * | 1930-02-22 | 1931-05-14 | Ig Farbenindustrie Ag | Improvements in the manufacture and production of 1.3-butylene glycol |
| DE664270C (de) * | 1936-04-12 | 1938-09-29 | Wacker Chemie Gmbh | Verfahren zum katalytischen Hydrieren von aliphatischen niedrigmolekularen Oxyoxoverbindungen |
| US2419300A (en) * | 1944-08-10 | 1947-04-22 | Air Reduction | Production of 1, 3-butylene glycol |
| US2549416A (en) * | 1948-02-04 | 1951-04-17 | Du Pont | Preparation of alcohols |
| US2921940A (en) * | 1955-11-28 | 1960-01-19 | Metal & Thermit Corp | Grignard preparation of certain hydroxy compounds |
| DE1014089B (de) * | 1956-05-05 | 1957-08-22 | Basf Ag | Verfahren zur Herstellung von 2,2-Dimethylpropandiol-(1,3) |
| US2978467A (en) * | 1957-01-22 | 1961-04-04 | Aerojet General Co | Nitro keto alcohols and esters |
| US2951854A (en) * | 1957-06-12 | 1960-09-06 | Gen Aniline & Film Corp | Bis-epoxides obtained from 2, 2, 3, 3-tetrahalo-1, 4-butanediol and methods of manufacture of the same |
| US2921957A (en) * | 1957-09-16 | 1960-01-19 | Jacques G O'rear | Process for the production of fluoroesters |
| US2942031A (en) * | 1958-10-06 | 1960-06-21 | Dow Chemical Co | 3, 3-dichloro-2-methylacroleins |
| US2989568A (en) * | 1958-12-31 | 1961-06-20 | Air Reduction | Preparation of halogenated acetylenic alcohols |
| FR1451677A (fr) * | 1964-10-21 | 1966-01-07 | Eastman Kodak Co | Fabrication de néopentyl-glycol et d'isobutanol |
| DE1804984A1 (de) * | 1967-10-27 | 1969-05-22 | Eastman Kodak Co | Verfahren zur Herstellung von 2,2-Dimethyl-1,3-propandiol |
-
1970
- 1970-11-06 DE DE2054601A patent/DE2054601C3/de not_active Expired
-
1971
- 1971-10-22 RO RO7100068545A patent/RO63376A/ro unknown
- 1971-10-28 FI FI3087/71A patent/FI55646C/fi active
- 1971-10-29 FR FR7139098A patent/FR2113422A5/fr not_active Expired
- 1971-10-29 GB GB5047571A patent/GB1363677A/en not_active Expired
- 1971-10-29 SE SE7113807A patent/SE391919B/xx unknown
- 1971-10-29 BR BR7283/71A patent/BR7107283D0/pt unknown
- 1971-10-29 AT AT936671A patent/AT313247B/de not_active IP Right Cessation
- 1971-10-30 IT IT53820/71A patent/IT942249B/it active
- 1971-11-05 CA CA126,962A patent/CA948217A/en not_active Expired
- 1971-11-06 JP JP46088636A patent/JPS5118928B1/ja active Pending
-
1976
- 1976-05-12 US US05/685,899 patent/US4094914A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| RO63376A (fr) | 1978-07-15 |
| GB1363677A (en) | 1974-08-14 |
| US4094914A (en) | 1978-06-13 |
| IT942249B (it) | 1973-03-20 |
| SE391919B (sv) | 1977-03-07 |
| FI55646C (fi) | 1979-09-10 |
| BR7107283D0 (pt) | 1973-06-14 |
| CA948217A (en) | 1974-05-28 |
| FI55646B (fi) | 1979-05-31 |
| FR2113422A5 (enExample) | 1972-06-23 |
| AU3517071A (en) | 1973-05-03 |
| JPS5118928B1 (enExample) | 1976-06-14 |
| DE2054601A1 (de) | 1972-05-10 |
| AT313247B (de) | 1974-02-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: HOECHST AG, 6230 FRANKFURT, DE |