DE1468282A1 - Verfahren zur Herstellung von Adipinsaeure durch Oxydation von Cyclohexan in fluessiger Phase mit molekularem Sauerstoff - Google Patents
Verfahren zur Herstellung von Adipinsaeure durch Oxydation von Cyclohexan in fluessiger Phase mit molekularem SauerstoffInfo
- Publication number
- DE1468282A1 DE1468282A1 DE19631468282 DE1468282A DE1468282A1 DE 1468282 A1 DE1468282 A1 DE 1468282A1 DE 19631468282 DE19631468282 DE 19631468282 DE 1468282 A DE1468282 A DE 1468282A DE 1468282 A1 DE1468282 A1 DE 1468282A1
- Authority
- DE
- Germany
- Prior art keywords
- adipic acid
- oxidation
- cyclohexane
- oil phase
- phase
- 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
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 title claims description 128
- 239000001361 adipic acid Substances 0.000 title claims description 64
- 235000011037 adipic acid Nutrition 0.000 title claims description 64
- 238000007254 oxidation reaction Methods 0.000 title claims description 60
- 230000003647 oxidation Effects 0.000 title claims description 59
- 238000000034 method Methods 0.000 title claims description 48
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 title claims description 38
- 239000007791 liquid phase Substances 0.000 title claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 title claims description 4
- 229910001882 dioxygen Inorganic materials 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000002243 precursor Substances 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 15
- 229910017604 nitric acid Inorganic materials 0.000 claims description 15
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 10
- 239000007800 oxidant agent Substances 0.000 claims description 6
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 3
- 239000012071 phase Substances 0.000 claims 13
- 239000008346 aqueous phase Substances 0.000 claims 10
- 238000001704 evaporation Methods 0.000 claims 9
- 230000008020 evaporation Effects 0.000 claims 9
- 238000001556 precipitation Methods 0.000 claims 2
- 150000002894 organic compounds Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 28
- 239000004215 Carbon black (E152) Substances 0.000 description 18
- 229930195733 hydrocarbon Natural products 0.000 description 18
- 150000002430 hydrocarbons Chemical class 0.000 description 18
- 238000007670 refining Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
- 239000002699 waste material Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 4
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- 206010067484 Adverse reaction Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 231100000621 toxification Toxicity 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000002351 wastewater Substances 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
- C07C51/313—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting with molecular oxygen
-
- 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
- C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
- C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22444362A | 1962-09-18 | 1962-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1468282A1 true DE1468282A1 (de) | 1969-01-02 |
Family
ID=22840703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631468282 Pending DE1468282A1 (de) | 1962-09-18 | 1963-09-17 | Verfahren zur Herstellung von Adipinsaeure durch Oxydation von Cyclohexan in fluessiger Phase mit molekularem Sauerstoff |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE637536A (forum.php) |
| CH (1) | CH435236A (forum.php) |
| DE (1) | DE1468282A1 (forum.php) |
| DK (1) | DK115251B (forum.php) |
| GB (1) | GB1013617A (forum.php) |
| LU (1) | LU44453A1 (forum.php) |
| NL (1) | NL298068A (forum.php) |
| NO (1) | NO116849B (forum.php) |
| SE (1) | SE312545B (forum.php) |
-
0
- NL NL298068D patent/NL298068A/xx unknown
- BE BE637536D patent/BE637536A/xx unknown
-
1963
- 1963-09-16 GB GB36395/63A patent/GB1013617A/en not_active Expired
- 1963-09-17 NO NO150127A patent/NO116849B/no unknown
- 1963-09-17 SE SE10171/63A patent/SE312545B/xx unknown
- 1963-09-17 CH CH1147163A patent/CH435236A/fr unknown
- 1963-09-17 DE DE19631468282 patent/DE1468282A1/de active Pending
- 1963-09-17 LU LU44453D patent/LU44453A1/xx unknown
- 1963-09-18 DK DK438563AA patent/DK115251B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| LU44453A1 (forum.php) | 1964-03-17 |
| NO116849B (forum.php) | 1969-06-02 |
| BE637536A (forum.php) | |
| NL298068A (forum.php) | |
| GB1013617A (en) | 1965-12-15 |
| CH435236A (fr) | 1967-05-15 |
| DK115251B (da) | 1969-09-22 |
| SE312545B (forum.php) | 1969-07-21 |
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