DE852993C - Verfahren zur Herstellung von 2, 4, 4-Trimethylpentanal - Google Patents
Verfahren zur Herstellung von 2, 4, 4-TrimethylpentanalInfo
- Publication number
- DE852993C DE852993C DED7394A DED0007394A DE852993C DE 852993 C DE852993 C DE 852993C DE D7394 A DED7394 A DE D7394A DE D0007394 A DED0007394 A DE D0007394A DE 852993 C DE852993 C DE 852993C
- Authority
- DE
- Germany
- Prior art keywords
- epoxy
- acidic substance
- treatment
- yield
- minutes
- 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 14
- PJLOOIXLBYOPHW-UHFFFAOYSA-N 2,4,4-trimethylpentanal Chemical compound O=CC(C)CC(C)(C)C PJLOOIXLBYOPHW-UHFFFAOYSA-N 0.000 title description 4
- 239000004593 Epoxy Substances 0.000 claims description 15
- 230000002378 acidificating effect Effects 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 6
- 239000012298 atmosphere Substances 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 229910015900 BF3 Inorganic materials 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- WZHRVCOCPMCGEA-UHFFFAOYSA-N 2-(2,2-dimethylpropyl)-2-methyloxirane Chemical compound CC(C)(C)CC1(C)CO1 WZHRVCOCPMCGEA-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical group [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 2
- 238000005342 ion exchange Methods 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 239000011135 tin Substances 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- FTZILAQGHINQQR-UHFFFAOYSA-N 2-Methylpentanal Chemical compound CCCC(C)C=O FTZILAQGHINQQR-UHFFFAOYSA-N 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 238000006317 isomerization reaction Methods 0.000 description 5
- 150000002924 oxiranes Chemical class 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical class O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910021623 Tin(IV) bromide Inorganic materials 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- -1 a-diisobutylene epoxide Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 239000010457 zeolite Substances 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
- C07C45/56—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
- C07C45/58—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 three-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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB31092/49A GB690383A (en) | 1949-12-03 | 1949-12-03 | Manufacture of 2:4:4-trimethylpentanal |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE852993C true DE852993C (de) | 1952-10-20 |
Family
ID=10317838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED7394A Expired DE852993C (de) | 1949-12-03 | 1950-11-26 | Verfahren zur Herstellung von 2, 4, 4-Trimethylpentanal |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2694090A (en:Method) |
| BE (1) | BE499678A (en:Method) |
| DE (1) | DE852993C (en:Method) |
| FR (1) | FR1028400A (en:Method) |
| GB (1) | GB690383A (en:Method) |
| NL (1) | NL77227C (en:Method) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3068291A (en) * | 1958-08-18 | 1962-12-11 | Exxon Research Engineering Co | Conversion of epoxides |
| DE2252719C3 (de) * | 1972-10-27 | 1981-02-19 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Aldehyden aus Oxiranverbindungen |
| FR2273789A2 (fr) * | 1974-06-06 | 1976-01-02 | Rhone Poulenc Ind | Procede pour la preparation de l'hexene-2 al |
| IT1152297B (it) * | 1982-07-28 | 1986-12-31 | Anic Spa | Procedimento per l'isomerizzazione di ossido di stirene od omologhi a beta-fenilaldeidi |
| US4517386A (en) * | 1984-05-11 | 1985-05-14 | Givaudan Corporation | Process for the rearrangement of epoxides |
| US4593130A (en) * | 1985-06-24 | 1986-06-03 | American Cyanamid Company | Synthesis of 10-hydroxymethyl-9-anthraldehyde |
| DE3632529A1 (de) * | 1986-09-25 | 1988-04-07 | Basf Ag | Verfahren zur herstellung von aldehyden und/oder ketonen durch umsetzung von epoxiden |
| US4925987A (en) * | 1989-04-13 | 1990-05-15 | Eastman Kodak Company | Preparation of aldehydes from unsaturated terminal epoxides |
| US4925986A (en) * | 1989-04-13 | 1990-05-15 | Eastman Kodak Company | Preparation of aldehydes from unsaturated terminal epoxides |
| US5312995A (en) * | 1993-04-23 | 1994-05-17 | Arco Chemical Technology, L.P. | Process for isomerizing epoxides to aldehydes |
| DE19538206A1 (de) * | 1995-10-13 | 1997-04-17 | Erdoelchemie Gmbh | Verfahren zur Herstellung von Propanal |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2031200A (en) * | 1929-02-05 | 1936-02-18 | Union Carbide & Carbon Corp | Process of making products including aliphatic aldehydes |
| US2159507A (en) * | 1936-01-22 | 1939-05-23 | Carbide & Carbon Chem Corp | Isomerization of alkylene oxides |
-
0
- BE BE499678D patent/BE499678A/fr unknown
- NL NL77227D patent/NL77227C/xx active
-
1949
- 1949-12-03 GB GB31092/49A patent/GB690383A/en not_active Expired
-
1950
- 1950-11-22 US US197168A patent/US2694090A/en not_active Expired - Lifetime
- 1950-11-25 FR FR1028400D patent/FR1028400A/fr not_active Expired
- 1950-11-26 DE DED7394A patent/DE852993C/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1028400A (fr) | 1953-05-21 |
| NL77227C (en:Method) | |
| GB690383A (en) | 1953-04-22 |
| US2694090A (en) | 1954-11-09 |
| BE499678A (en:Method) |
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