DE1468280A1 - 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
- DE1468280A1 DE1468280A1 DE19631468280 DE1468280A DE1468280A1 DE 1468280 A1 DE1468280 A1 DE 1468280A1 DE 19631468280 DE19631468280 DE 19631468280 DE 1468280 A DE1468280 A DE 1468280A DE 1468280 A1 DE1468280 A1 DE 1468280A1
- Authority
- DE
- Germany
- Prior art keywords
- adipic acid
- oxidation
- cyclohexane
- phase
- oil 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 118
- 239000001361 adipic acid Substances 0.000 title claims description 59
- 235000011037 adipic acid Nutrition 0.000 title claims description 59
- 230000003647 oxidation Effects 0.000 title claims description 54
- 238000007254 oxidation reaction Methods 0.000 title claims description 54
- 238000000034 method Methods 0.000 title claims description 50
- 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
- 238000004519 manufacturing process Methods 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
- 239000002243 precursor Substances 0.000 claims description 37
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 16
- 229910017604 nitric acid Inorganic materials 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 238000004821 distillation Methods 0.000 claims description 14
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 12
- 238000000926 separation method Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 5
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 4
- 239000012071 phase Substances 0.000 claims 15
- 239000008346 aqueous phase Substances 0.000 claims 5
- 238000001704 evaporation Methods 0.000 claims 5
- 230000008020 evaporation Effects 0.000 claims 5
- 241000726221 Gemma Species 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000002894 organic compounds Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 description 24
- 239000004215 Carbon black (E152) Substances 0.000 description 17
- 229930195733 hydrocarbon Natural products 0.000 description 17
- 150000002430 hydrocarbons Chemical class 0.000 description 17
- 238000007670 refining Methods 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 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
- 239000007788 liquid Substances 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 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
- 241000220317 Rosa Species 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003351 stiffener Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001384 succinic acid Substances 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)
- Braking Arrangements (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22443562A | 1962-09-18 | 1962-09-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1468280A1 true DE1468280A1 (de) | 1969-01-02 |
Family
ID=22840667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631468280 Pending DE1468280A1 (de) | 1962-09-18 | 1963-09-17 | Verfahren zur Herstellung von Adipinsaeure durch Oxydation von Cyclohexan in fluessiger Phase mit molekularem Sauerstoff |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5019533B1 (en:Method) |
| BE (1) | BE637535A (en:Method) |
| CH (1) | CH426762A (en:Method) |
| DE (1) | DE1468280A1 (en:Method) |
| DK (1) | DK114764B (en:Method) |
| GB (1) | GB1013619A (en:Method) |
| LU (1) | LU44452A1 (en:Method) |
| NL (1) | NL298067A (en:Method) |
| NO (1) | NO116848B (en:Method) |
| SE (1) | SE312332B (en:Method) |
-
0
- NL NL298067D patent/NL298067A/xx unknown
- BE BE637535D patent/BE637535A/xx unknown
-
1963
- 1963-09-16 GB GB36397/63A patent/GB1013619A/en not_active Expired
- 1963-09-17 NO NO150126A patent/NO116848B/no unknown
- 1963-09-17 LU LU44452D patent/LU44452A1/xx unknown
- 1963-09-17 CH CH1147063A patent/CH426762A/fr unknown
- 1963-09-17 DK DK437763AA patent/DK114764B/da unknown
- 1963-09-17 SE SE10172/63A patent/SE312332B/xx unknown
- 1963-09-17 DE DE19631468280 patent/DE1468280A1/de active Pending
- 1963-09-18 JP JP38050087A patent/JPS5019533B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NO116848B (en:Method) | 1969-06-02 |
| DK114764B (da) | 1969-08-04 |
| LU44452A1 (en:Method) | 1964-03-17 |
| SE312332B (en:Method) | 1969-07-14 |
| GB1013619A (en) | 1965-12-15 |
| JPS5019533B1 (en:Method) | 1975-07-08 |
| NL298067A (en:Method) | |
| BE637535A (en:Method) | |
| CH426762A (fr) | 1966-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 |