DE1921441C - - Google Patents
Info
- Publication number
- DE1921441C DE1921441C DE19691921441 DE1921441A DE1921441C DE 1921441 C DE1921441 C DE 1921441C DE 19691921441 DE19691921441 DE 19691921441 DE 1921441 A DE1921441 A DE 1921441A DE 1921441 C DE1921441 C DE 1921441C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- mixture
- methylcyclohexanol
- oxidation
- cyclohexanol
- 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
- 239000000203 mixture Substances 0.000 claims description 15
- 230000003647 oxidation Effects 0.000 claims description 9
- 238000007254 oxidation reaction Methods 0.000 claims description 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 8
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 8
- 229910017604 nitric acid Inorganic materials 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 4
- 229930003836 cresol Natural products 0.000 claims description 4
- VTBOTOBFGSVRMA-UHFFFAOYSA-N 1-Methylcyclohexanol Chemical class CC1(O)CCCCC1 VTBOTOBFGSVRMA-UHFFFAOYSA-N 0.000 claims description 3
- SYEOWUNSTUDKGM-UHFFFAOYSA-N beta-methyladipic acid Natural products OC(=O)CC(C)CCC(O)=O SYEOWUNSTUDKGM-UHFFFAOYSA-N 0.000 claims description 3
- NDVWOBYBJYUSMF-UHFFFAOYSA-N 2-methylcyclohexan-1-ol Chemical compound CC1CCCCC1O NDVWOBYBJYUSMF-UHFFFAOYSA-N 0.000 claims description 2
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 claims description 2
- GAYWCADKXYCKCG-UHFFFAOYSA-N 5-pyridin-3-yl-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1NC(=S)N=C1C1=CC=CN=C1 GAYWCADKXYCKCG-UHFFFAOYSA-N 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000012452 mother liquor Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WDBZEBXYXWWDPJ-UHFFFAOYSA-N 3-(2-methylphenoxy)propanoic acid Chemical compound CC1=CC=CC=C1OCCC(O)=O WDBZEBXYXWWDPJ-UHFFFAOYSA-N 0.000 description 1
- SYEOWUNSTUDKGM-YFKPBYRVSA-N 3-methyladipic acid Chemical compound OC(=O)C[C@@H](C)CCC(O)=O SYEOWUNSTUDKGM-YFKPBYRVSA-N 0.000 description 1
- HTSABYAWKQAHBT-UHFFFAOYSA-N 3-methylcyclohexanol Chemical compound CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentoxide Inorganic materials [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691921441 DE1921441A1 (de) | 1969-04-26 | 1969-04-26 | Verfahren zur Herstellung von 3-Methyladipinsaeure |
| NL6918332A NL6918332A (enrdf_load_stackoverflow) | 1969-04-26 | 1969-12-05 | |
| AT1153569A AT293352B (de) | 1969-04-26 | 1969-12-11 | Verfahren zur Herstellung von β-Methyladipinsäure |
| BE743359D BE743359A (enrdf_load_stackoverflow) | 1969-04-26 | 1969-12-18 | |
| FR6944450A FR2030928A5 (enrdf_load_stackoverflow) | 1969-04-26 | 1969-12-22 | |
| GB63099/69A GB1300398A (en) | 1969-04-26 | 1969-12-29 | METHOD OF PREPARING beta-METHYL ADIPIC ACID |
| US19494A US3705921A (en) | 1969-04-26 | 1970-03-13 | Method of preparing {62 -methyl adipic acid |
| JP45032407A JPS4823423B1 (enrdf_load_stackoverflow) | 1969-04-26 | 1970-04-17 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691921441 DE1921441A1 (de) | 1969-04-26 | 1969-04-26 | Verfahren zur Herstellung von 3-Methyladipinsaeure |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1921441A1 DE1921441A1 (de) | 1972-04-06 |
| DE1921441C true DE1921441C (enrdf_load_stackoverflow) | 1973-05-10 |
Family
ID=5732531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691921441 Granted DE1921441A1 (de) | 1969-04-26 | 1969-04-26 | Verfahren zur Herstellung von 3-Methyladipinsaeure |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3705921A (enrdf_load_stackoverflow) |
| JP (1) | JPS4823423B1 (enrdf_load_stackoverflow) |
| AT (1) | AT293352B (enrdf_load_stackoverflow) |
| BE (1) | BE743359A (enrdf_load_stackoverflow) |
| DE (1) | DE1921441A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2030928A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1300398A (enrdf_load_stackoverflow) |
| NL (1) | NL6918332A (enrdf_load_stackoverflow) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB265959A (en) * | 1926-02-12 | 1927-12-08 | Riedel J D Ag | A process for producing adipic acid and its alkyl substitution products |
| US2300955A (en) * | 1939-05-06 | 1942-11-03 | Meier Gerhard | Process for the production of adipic acid and alkyladipic acids |
| DE1205516B (de) * | 1962-07-06 | 1965-11-25 | Hibernia Chemie Ges Mit Beschr | Verfahren zur Herstellung von Alkyladipinsaeuren |
-
1969
- 1969-04-26 DE DE19691921441 patent/DE1921441A1/de active Granted
- 1969-12-05 NL NL6918332A patent/NL6918332A/xx unknown
- 1969-12-11 AT AT1153569A patent/AT293352B/de not_active IP Right Cessation
- 1969-12-18 BE BE743359D patent/BE743359A/xx unknown
- 1969-12-22 FR FR6944450A patent/FR2030928A5/fr not_active Expired
- 1969-12-29 GB GB63099/69A patent/GB1300398A/en not_active Expired
-
1970
- 1970-03-13 US US19494A patent/US3705921A/en not_active Expired - Lifetime
- 1970-04-17 JP JP45032407A patent/JPS4823423B1/ja active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3207746A1 (de) | Verfahren zur herstellung von trimethylolpropan | |
| DE1921441C (enrdf_load_stackoverflow) | ||
| DE842198C (de) | Verfahren zur Herstellung von Vinylsulfonen | |
| DE3435392A1 (de) | Verfahren zur herstellung von 2,4-dichlor-5-fluor-benzoesaeure | |
| DE2060218A1 (de) | Verfahren zur Herstellung von 1-Phenyl-vinyl-1-phosphonsaeure | |
| DE2237750C2 (de) | Verfahren zur Herstellung von Brenzcatechin | |
| DE851194C (de) | Verfahren zur Herstellung von monomerem ªŠ-Caprolactam | |
| DE753046C (de) | Verfahren zur Umlagerung von Ketoximen | |
| DE1921441B (de) | Verfahren zur Herstellung von beta-Methyladipinsäure | |
| DE907172C (de) | Verfahren zur Herstellung von Thiosemicarbazid | |
| DE2118493C3 (de) | Verfahren zur Herstellung von Aminostilbenen | |
| DE3813452A1 (de) | Verfahren zur herstellung von trifluormethylbenzoesaeure aus hexafluorxylol | |
| DE885846C (de) | Verfahren zur Herstellung von Alkoholen der Acetylenreihe | |
| DE2012434C3 (de) | Verfahren zur Herstellung von mindestens 10 Ringglieder aufweisenden N-Alkyllactam | |
| DE2321332C2 (de) | Verfahren zur Herstellung von 2-Nitro-5-chlor-benzolsulfonsäurechlorid oder von 2-Nitro-5-chlor-benzolsulfonsäure | |
| DE962527C (de) | Verfahren zur Herstellung von Oxyhydroperoxyden | |
| DE1168408B (de) | Verfahren zur Herstellung von ª‰-Methylmercaptopropionaldehyd | |
| DE1097429B (de) | Verfahren zur Herstellung niedermolekularer Acetondicarbonsaeuredialkylester | |
| DE2225367C3 (de) | Verfahren zur Herstellung von Diglykolsäure | |
| DE1232573B (de) | Verfahren zur Herstellung von Alkinolen | |
| DE740445C (de) | Verfahren zur Herstellung von p,p-Diaminodiphenylsulfon | |
| DE1156400B (de) | Verfahren zur Herstellung von Mucochlorsaeure und Tetrachlorbutandiol | |
| DE1921441A1 (de) | Verfahren zur Herstellung von 3-Methyladipinsaeure | |
| DE835596C (de) | Verfahren zur Aufarbeitung der bei der Umwandlung von p-Oxyalkylphenonen in Pinakonverbindungen anfallenden Mutterlaugen | |
| DE765787C (de) | Verfahren zur Herstellung von Umsetzungsprodukten von Formaldehyd mit Blausaeure |