DE2045669B2 - Verfahren zur herstellung von hydroxypivalaldehyd - Google Patents
Verfahren zur herstellung von hydroxypivalaldehydInfo
- Publication number
- DE2045669B2 DE2045669B2 DE19702045669 DE2045669A DE2045669B2 DE 2045669 B2 DE2045669 B2 DE 2045669B2 DE 19702045669 DE19702045669 DE 19702045669 DE 2045669 A DE2045669 A DE 2045669A DE 2045669 B2 DE2045669 B2 DE 2045669B2
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- formaldehyde
- isobutyraldehyde
- hydroxypivalaldehyde
- neopentyl glycol
- 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.)
- Ceased
Links
- JJMOMMLADQPZNY-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanal Chemical compound OCC(C)(C)C=O JJMOMMLADQPZNY-UHFFFAOYSA-N 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 94
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 9
- 239000000376 reactant Substances 0.000 claims description 3
- 238000003541 multi-stage reaction Methods 0.000 claims 1
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 229940117969 neopentyl glycol Drugs 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 7
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- -1 cyclic acetal Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 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 3
- 238000005705 Cannizzaro reaction Methods 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical class CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- MWUFBHZBQXJHGM-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;2-methylpropanoic acid Chemical compound CC(C)C(O)=O.OCC(C)(C)CO MWUFBHZBQXJHGM-UHFFFAOYSA-N 0.000 description 1
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 238000006423 Tishchenko reaction Methods 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000006199 crossed Cannizzaro oxidation reduction reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination 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
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/75—Reactions with formaldehyde
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702045669 DE2045669B2 (de) | 1970-09-16 | 1970-09-16 | Verfahren zur herstellung von hydroxypivalaldehyd |
| GB3357571A GB1353761A (en) | 1970-09-16 | 1971-07-16 | Process for the production of hydroxypivalaldehyde |
| ZA714834A ZA714834B (en) | 1970-09-16 | 1971-07-20 | Process for the production of hydroxypivalaldehyde |
| AT641871A AT308714B (de) | 1970-09-16 | 1971-07-23 | Verfahren zur Herstellung von Hydroxypivalaldehyd |
| CA122,428A CA941842A (en) | 1970-09-16 | 1971-09-09 | Process for preparing hydroxypivalaldehyde |
| BE772538A BE772538A (fr) | 1970-09-16 | 1971-09-13 | Procede de preparation de l'aldehyde hydroxypivalique |
| NL7112570.A NL165449C (nl) | 1970-09-16 | 1971-09-13 | Werkwijze ter bereiding van hydroxypivalaldehyde uit isobutyraldehyde en formaldehyde. |
| FR7133249A FR2107705A5 (enrdf_load_stackoverflow) | 1970-09-16 | 1971-09-15 | |
| BR6041/71A BR7106041D0 (pt) | 1970-09-16 | 1971-09-15 | Processo para preparacao de hidroxi-pivalaldeido |
| JP46072109A JPS515367B1 (enrdf_load_stackoverflow) | 1970-09-16 | 1971-09-16 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702045669 DE2045669B2 (de) | 1970-09-16 | 1970-09-16 | Verfahren zur herstellung von hydroxypivalaldehyd |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2045669A1 DE2045669A1 (de) | 1972-03-23 |
| DE2045669B2 true DE2045669B2 (de) | 1977-06-23 |
Family
ID=5782519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702045669 Ceased DE2045669B2 (de) | 1970-09-16 | 1970-09-16 | Verfahren zur herstellung von hydroxypivalaldehyd |
Country Status (10)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101529828B1 (ko) * | 2013-07-26 | 2015-06-17 | 주식회사 엘지화학 | 메틸올알칸알의 제조방법 |
| EP3401301B1 (en) * | 2016-01-07 | 2021-03-31 | Mitsubishi Gas Chemical Company, Inc. | Hydroxypivalaldehyde production method |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH238328A (fr) * | 1942-03-20 | 1945-07-15 | Melle Usines Sa | Procédé de fabrication des aldols. |
| US3504042A (en) * | 1963-11-06 | 1970-03-31 | Mitsubishi Gas Chemical Co | Process for producing 2,2-dimethyl-1,3-propanediol |
| RO55309A (enrdf_load_stackoverflow) * | 1968-04-24 | 1973-07-20 |
-
1970
- 1970-09-16 DE DE19702045669 patent/DE2045669B2/de not_active Ceased
-
1971
- 1971-07-16 GB GB3357571A patent/GB1353761A/en not_active Expired
- 1971-07-20 ZA ZA714834A patent/ZA714834B/xx unknown
- 1971-07-23 AT AT641871A patent/AT308714B/de not_active IP Right Cessation
- 1971-09-09 CA CA122,428A patent/CA941842A/en not_active Expired
- 1971-09-13 NL NL7112570.A patent/NL165449C/xx not_active IP Right Cessation
- 1971-09-13 BE BE772538A patent/BE772538A/xx unknown
- 1971-09-15 FR FR7133249A patent/FR2107705A5/fr not_active Expired
- 1971-09-15 BR BR6041/71A patent/BR7106041D0/pt unknown
- 1971-09-16 JP JP46072109A patent/JPS515367B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA941842A (en) | 1974-02-12 |
| BR7106041D0 (pt) | 1973-04-19 |
| NL165449B (nl) | 1980-11-17 |
| DE2045669A1 (de) | 1972-03-23 |
| NL165449C (nl) | 1981-04-15 |
| GB1353761A (en) | 1974-05-22 |
| NL7112570A (enrdf_load_stackoverflow) | 1972-03-20 |
| FR2107705A5 (enrdf_load_stackoverflow) | 1972-05-05 |
| ZA714834B (en) | 1972-04-26 |
| BE772538A (fr) | 1972-03-13 |
| JPS515367B1 (enrdf_load_stackoverflow) | 1976-02-19 |
| AT308714B (de) | 1973-07-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0876316B1 (de) | Verfahren zur herstellung von polyalkoholen | |
| EP0412337B1 (de) | Verfahren zur Herstellung von 1,3-Propandiol | |
| DE1957591A1 (de) | Verfahren zur Herstellung von 2,2-Dimethylpropandiol | |
| DE19653093A1 (de) | Verfahren zur Herstellung von Polyalkoholen | |
| EP1103538B1 (de) | Verfahren zur Durchführung von Aldolkondensationen | |
| DE2054601C3 (de) | Verfahren zur Herstellung von zweiwertigen Alkoholen | |
| WO2014067602A1 (de) | Kontinuierliches verfahren zur herstellung von neopentylglykol | |
| EP0317909A2 (de) | Verfahren zur Herstellung von alpha-Alkylacroleinen | |
| DE10317543A1 (de) | Verfahren zur Hydrierung von Methylolalkanalen | |
| EP0062291B1 (de) | Verbessertes Verfahren zur Herstellung mehrfach ungesättigter Ketone | |
| DE69214026T2 (de) | Herstellung von Neopentylglykol (III) | |
| DE69904048T2 (de) | Cross-Aldolkondensation für Hydroxypivaldehyd | |
| EP0151241B1 (de) | Verfahren zur Herstellung von 1,4 Butandial | |
| DE2045669B2 (de) | Verfahren zur herstellung von hydroxypivalaldehyd | |
| DE102019209233A1 (de) | Verfahren zur Herstellung eines β-Hydroxyketons | |
| DE19753157A1 (de) | Verfahren zur Herstellung von gesättigten Alkoholen | |
| EP0561213B1 (de) | Verfahren zur Herstellung von Hydroxypivalinsäureneopentylglykolester | |
| EP3315484B1 (de) | Verfahren zur koppelproduktion von polyolen in gegenwart einer anorganischen base | |
| DE1768274C3 (de) | Verfahren zur kontinuierlichen Herstellung von Hydroxypivalinaldehyd | |
| DE554949C (de) | Verfahren zur Herstellung von Alkoxyaldehyden | |
| DE2431814C3 (de) | Verfahren zur Herstellung von Di- bis Polyhydroxyverbindungen durch Reaktion von Formaldehyd mit Aldehyden oder Ketonen | |
| DE1816042A1 (de) | Verfahren zur Herstellung von Acetylenglykolen | |
| DE1593005C3 (de) | Verfahren zur Herstellung von Methylacrylat oder Methyl- bzw. Äthylmethacrylat | |
| AT371131B (de) | Verfahren zur herstellung von mischungen teilver- aetherter methylolmelamine | |
| DE964858C (de) | Verfahren zur Herstellung eines Polyendialdehyds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8235 | Patent refused |