DE1111163B - Verfahren zur Herstellung von Gemischen aus ª‡, ª‡, ª†- und ª‡, ª†, ª†-Trimethyladipinsaeure - Google Patents
Verfahren zur Herstellung von Gemischen aus ª‡, ª‡, ª†- und ª‡, ª†, ª†-TrimethyladipinsaeureInfo
- Publication number
- DE1111163B DE1111163B DEB54181A DEB0054181A DE1111163B DE 1111163 B DE1111163 B DE 1111163B DE B54181 A DEB54181 A DE B54181A DE B0054181 A DEB0054181 A DE B0054181A DE 1111163 B DE1111163 B DE 1111163B
- Authority
- DE
- Germany
- Prior art keywords
- acid
- nitric acid
- temperature
- mixtures
- preparation
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 17
- 229910017604 nitric acid Inorganic materials 0.000 claims description 17
- 230000003647 oxidation Effects 0.000 claims description 12
- 238000007254 oxidation reaction Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 2
- WDBZEBXYXWWDPJ-UHFFFAOYSA-N 3-(2-methylphenoxy)propanoic acid Chemical compound CC1=CC=CC=C1OCCC(O)=O WDBZEBXYXWWDPJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 8
- GBURUDXSBYGPBL-UHFFFAOYSA-N 2,2,3-trimethylhexanedioic acid Chemical class OC(=O)C(C)(C)C(C)CCC(O)=O GBURUDXSBYGPBL-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- UENOQWSWMYJKIW-UHFFFAOYSA-N 1,2,2-trimethylcyclohexan-1-ol Chemical class CC1(C)CCCCC1(C)O UENOQWSWMYJKIW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 2
- -1 alkyl adipic acids Chemical class 0.000 description 2
- UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- DOBUSJIVSSJEDA-UHFFFAOYSA-L 1,3-dioxa-2$l^{6}-thia-4-mercuracyclobutane 2,2-dioxide Chemical compound [Hg+2].[O-]S([O-])(=O)=O DOBUSJIVSSJEDA-UHFFFAOYSA-L 0.000 description 1
- HKNMYDUELTUXOL-UHFFFAOYSA-N 2,2,3-trimethylpentanedioic acid Chemical compound OC(=O)CC(C)C(C)(C)C(O)=O HKNMYDUELTUXOL-UHFFFAOYSA-N 0.000 description 1
- BTVZFIIHBJWMOG-UHFFFAOYSA-N 2,2-dimethylhexanedioic acid Chemical class OC(=O)C(C)(C)CCCC(O)=O BTVZFIIHBJWMOG-UHFFFAOYSA-N 0.000 description 1
- KLZYRCVPDWTZLH-UHFFFAOYSA-N 2,3-dimethylsuccinic acid Chemical compound OC(=O)C(C)C(C)C(O)=O KLZYRCVPDWTZLH-UHFFFAOYSA-N 0.000 description 1
- JZUMVFMLJGSMRF-UHFFFAOYSA-N 2-Methyladipic acid Chemical class OC(=O)C(C)CCCC(O)=O JZUMVFMLJGSMRF-UHFFFAOYSA-N 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- 206010021703 Indifference Diseases 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910000474 mercury oxide Inorganic materials 0.000 description 1
- 229910000370 mercury sulfate Inorganic materials 0.000 description 1
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/31—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting
- C07C51/316—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting with oxides of nitrogen or nitrogen-containing mineral acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL132123D NL132123C (enrdf_load_stackoverflow) | 1959-07-25 | ||
| LU38674D LU38674A1 (enrdf_load_stackoverflow) | 1959-07-25 | ||
| DEB54181A DE1111163B (de) | 1959-07-25 | 1959-07-25 | Verfahren zur Herstellung von Gemischen aus ª‡, ª‡, ª†- und ª‡, ª†, ª†-Trimethyladipinsaeure |
| DE1418067A DE1418067C3 (de) | 1959-07-25 | 1959-09-26 | Verfahren zur Herstellung von Trialkyladiplnsäuren |
| DE1959B0056111 DE1418074B2 (de) | 1959-07-25 | 1959-12-31 | Verfahren zur herstellung von trimethyladipinsaeuren |
| CH584060A CH388283A (de) | 1959-07-25 | 1960-05-20 | Verfahren zur Herstellung von Trialkyladipinsäuren |
| GB20177/60A GB915510A (en) | 1959-07-25 | 1960-06-08 | Improvements in or relating to the production of trialkyladipic acids |
| BE592408A BE592408A (fr) | 1959-07-25 | 1960-06-29 | Procédé de préparation d'acide triméthyl-adipique et produit obtenu |
| FR833223A FR1262501A (fr) | 1959-07-25 | 1960-07-18 | Procédé de préparation d'acides trialcoyladipiques et produits conformes à ceux obtenus |
| DK290560AA DK106549C (da) | 1959-07-25 | 1960-07-23 | Fremgangsmåde til fremstilling af trialkyladipinsyrer, navnlig trimethyladipinsyre. |
| NL254152D NL254152A (enrdf_load_stackoverflow) | 1959-07-25 | 1960-07-25 | |
| SE1273761A SE302455B (sv) | 1959-07-25 | 1961-12-20 | Framställning av trialkyladipinsyror |
| NL717100724A NL143896B (nl) | 1959-07-25 | 1971-01-19 | Werkwijze voor de bereiding van de alfa,alfa,gamma- en alfa,gamma,gamma,- isomeren van trialkyladipinezuren. |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB54181A DE1111163B (de) | 1959-07-25 | 1959-07-25 | Verfahren zur Herstellung von Gemischen aus ª‡, ª‡, ª†- und ª‡, ª†, ª†-Trimethyladipinsaeure |
| DEB0054955 | 1959-09-26 | ||
| DE1959B0056111 DE1418074B2 (de) | 1959-07-25 | 1959-12-31 | Verfahren zur herstellung von trimethyladipinsaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1111163B true DE1111163B (de) | 1961-07-20 |
Family
ID=27209092
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB54181A Pending DE1111163B (de) | 1959-07-25 | 1959-07-25 | Verfahren zur Herstellung von Gemischen aus ª‡, ª‡, ª†- und ª‡, ª†, ª†-Trimethyladipinsaeure |
| DE1418067A Expired DE1418067C3 (de) | 1959-07-25 | 1959-09-26 | Verfahren zur Herstellung von Trialkyladiplnsäuren |
| DE1959B0056111 Granted DE1418074B2 (de) | 1959-07-25 | 1959-12-31 | Verfahren zur herstellung von trimethyladipinsaeuren |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1418067A Expired DE1418067C3 (de) | 1959-07-25 | 1959-09-26 | Verfahren zur Herstellung von Trialkyladiplnsäuren |
| DE1959B0056111 Granted DE1418074B2 (de) | 1959-07-25 | 1959-12-31 | Verfahren zur herstellung von trimethyladipinsaeuren |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE592408A (enrdf_load_stackoverflow) |
| CH (1) | CH388283A (enrdf_load_stackoverflow) |
| DE (3) | DE1111163B (enrdf_load_stackoverflow) |
| DK (1) | DK106549C (enrdf_load_stackoverflow) |
| FR (1) | FR1262501A (enrdf_load_stackoverflow) |
| GB (1) | GB915510A (enrdf_load_stackoverflow) |
| LU (1) | LU38674A1 (enrdf_load_stackoverflow) |
| NL (2) | NL254152A (enrdf_load_stackoverflow) |
| SE (1) | SE302455B (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1229510B (de) * | 1963-01-26 | 1966-12-01 | Scholven Chemie Ag | Verfahren zur Reinigung von fluessigen Gemischen aus alpha, alpha, gamma-alpha, gammaTrimethyladipinsaeure |
| US3297736A (en) * | 1963-02-11 | 1967-01-10 | Scholven Chemie Ag | Production of trimethyl adipic dinitrile |
| US3297741A (en) * | 1963-02-11 | 1967-01-10 | Scholven Chemie Ag | Process for the purification of trimethyl adipic dinitrile |
| US3297740A (en) * | 1963-02-11 | 1967-01-10 | Scholven Chemie Ag | Process for the production of trimethyl adipic acid dinitrile |
-
0
- LU LU38674D patent/LU38674A1/xx unknown
- NL NL132123D patent/NL132123C/xx active
-
1959
- 1959-07-25 DE DEB54181A patent/DE1111163B/de active Pending
- 1959-09-26 DE DE1418067A patent/DE1418067C3/de not_active Expired
- 1959-12-31 DE DE1959B0056111 patent/DE1418074B2/de active Granted
-
1960
- 1960-05-20 CH CH584060A patent/CH388283A/de unknown
- 1960-06-08 GB GB20177/60A patent/GB915510A/en not_active Expired
- 1960-06-29 BE BE592408A patent/BE592408A/fr unknown
- 1960-07-18 FR FR833223A patent/FR1262501A/fr not_active Expired
- 1960-07-23 DK DK290560AA patent/DK106549C/da active
- 1960-07-25 NL NL254152D patent/NL254152A/xx unknown
-
1961
- 1961-12-20 SE SE1273761A patent/SE302455B/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1229510B (de) * | 1963-01-26 | 1966-12-01 | Scholven Chemie Ag | Verfahren zur Reinigung von fluessigen Gemischen aus alpha, alpha, gamma-alpha, gammaTrimethyladipinsaeure |
| US3297736A (en) * | 1963-02-11 | 1967-01-10 | Scholven Chemie Ag | Production of trimethyl adipic dinitrile |
| US3297741A (en) * | 1963-02-11 | 1967-01-10 | Scholven Chemie Ag | Process for the purification of trimethyl adipic dinitrile |
| US3297740A (en) * | 1963-02-11 | 1967-01-10 | Scholven Chemie Ag | Process for the production of trimethyl adipic acid dinitrile |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1418067A1 (de) | 1968-10-24 |
| SE302455B (sv) | 1968-07-22 |
| DE1418074B2 (de) | 1976-05-06 |
| CH388283A (de) | 1965-02-28 |
| DE1418067B2 (enrdf_load_stackoverflow) | 1974-08-22 |
| LU38674A1 (enrdf_load_stackoverflow) | |
| DE1418067C3 (de) | 1975-06-19 |
| DE1418074A1 (de) | 1968-10-24 |
| NL254152A (enrdf_load_stackoverflow) | |
| DK106549C (da) | 1967-02-20 |
| FR1262501A (fr) | 1961-05-26 |
| BE592408A (fr) | 1960-10-17 |
| NL132123C (enrdf_load_stackoverflow) | |
| GB915510A (en) | 1963-01-16 |
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