DE2151535A1 - Zerlegung von Dicarbonsaeuremischungen - Google Patents
Zerlegung von DicarbonsaeuremischungenInfo
- Publication number
- DE2151535A1 DE2151535A1 DE19712151535 DE2151535A DE2151535A1 DE 2151535 A1 DE2151535 A1 DE 2151535A1 DE 19712151535 DE19712151535 DE 19712151535 DE 2151535 A DE2151535 A DE 2151535A DE 2151535 A1 DE2151535 A1 DE 2151535A1
- Authority
- DE
- Germany
- Prior art keywords
- adipic acid
- acid
- ammonia
- glutaric
- mixture
- 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 22
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title 1
- 230000015556 catabolic process Effects 0.000 title 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 77
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 43
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 41
- 239000001361 adipic acid Substances 0.000 claims description 38
- 235000011037 adipic acid Nutrition 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 24
- 239000001384 succinic acid Substances 0.000 claims description 21
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 20
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 20
- 229910021529 ammonia Inorganic materials 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 claims description 12
- 150000003949 imides Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 150000007513 acids Chemical class 0.000 claims description 7
- 239000012452 mother liquor Substances 0.000 claims description 7
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 235000011044 succinic acid Nutrition 0.000 claims 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- 150000001991 dicarboxylic acids Chemical class 0.000 claims 1
- 150000002311 glutaric acids Chemical class 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 150000003444 succinic acids Chemical class 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000005587 bubbling Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 3
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000589614 Pseudomonas stutzeri Species 0.000 description 1
- 150000001278 adipic acid derivatives Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- -1 cyclic lactams Chemical class 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying 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
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052720 vanadium Chemical class 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical class [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 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
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA95668 | 1970-10-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2151535A1 true DE2151535A1 (de) | 1972-04-20 |
Family
ID=4087793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712151535 Pending DE2151535A1 (de) | 1970-10-15 | 1971-10-15 | Zerlegung von Dicarbonsaeuremischungen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3818081A (OSRAM) |
| BE (1) | BE773931A (OSRAM) |
| CA (1) | CA955876A (OSRAM) |
| DE (1) | DE2151535A1 (OSRAM) |
| FR (1) | FR2111380A5 (OSRAM) |
| GB (1) | GB1352738A (OSRAM) |
| IT (1) | IT945991B (OSRAM) |
| NL (1) | NL7114238A (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0033851B1 (de) * | 1980-01-23 | 1983-03-09 | BASF Aktiengesellschaft | Verfahren zur Abtrennung von Adipinsäure aus Gemischen mit Glutarsäuren und/oder Bernsteinsäuren |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3983208A (en) * | 1975-01-27 | 1976-09-28 | Celanese Corporation | Recovery of vanadium and copper catalyst metals using ketones |
| CA1208239A (en) * | 1983-06-07 | 1986-07-22 | Christian Leboeuf | Semi-refined mixed dicarboxylic acids |
| DE4106937A1 (de) * | 1991-03-05 | 1992-09-10 | Bayer Ag | Verfahren zur rueckgewinnung von adipinsaeure |
| US5296639A (en) * | 1992-12-18 | 1994-03-22 | E. I. Du Pont De Nemours And Company | Adipic acid purification |
| DE4441175A1 (de) * | 1994-11-18 | 1996-05-23 | Bayer Ag | Verfahren zur Gewinnung von Adipinsäure |
| MY137537A (en) * | 2002-05-10 | 2009-02-27 | Mitsubishi Chem Corp | Method for producing organic acid |
| CN100412048C (zh) * | 2002-05-10 | 2008-08-20 | 三菱化学株式会社 | 分解有机酸铵盐的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2283991A (en) * | 1939-11-25 | 1942-05-26 | American Cyanamid Co | Separation of sulphuric acid from carboxylic acids |
| US2776990A (en) * | 1953-01-26 | 1957-01-08 | Du Pont | Separation of a dibasic acid from a mixture of mono and dibasic acids |
| DE954330C (de) * | 1953-11-29 | 1956-12-13 | Bayer Ag | Verfahren zur Aufarbeitung von Dicarbonsaeuregemischen |
| US2962527A (en) * | 1957-12-24 | 1960-11-29 | Texaco Inc | Purification of dibasic acids |
| NL289024A (OSRAM) * | 1962-02-19 |
-
1970
- 1970-10-15 CA CA095,668A patent/CA955876A/en not_active Expired
-
1971
- 1971-09-30 GB GB4563871A patent/GB1352738A/en not_active Expired
- 1971-10-07 US US00187511A patent/US3818081A/en not_active Expired - Lifetime
- 1971-10-11 IT IT29757/71A patent/IT945991B/it active
- 1971-10-14 FR FR7136962A patent/FR2111380A5/fr not_active Expired
- 1971-10-14 BE BE773931A patent/BE773931A/xx unknown
- 1971-10-15 DE DE19712151535 patent/DE2151535A1/de active Pending
- 1971-10-15 NL NL7114238A patent/NL7114238A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0033851B1 (de) * | 1980-01-23 | 1983-03-09 | BASF Aktiengesellschaft | Verfahren zur Abtrennung von Adipinsäure aus Gemischen mit Glutarsäuren und/oder Bernsteinsäuren |
Also Published As
| Publication number | Publication date |
|---|---|
| BE773931A (fr) | 1972-01-31 |
| CA955876A (en) | 1974-10-08 |
| FR2111380A5 (OSRAM) | 1972-06-02 |
| US3818081A (en) | 1974-06-18 |
| GB1352738A (en) | 1974-05-08 |
| IT945991B (it) | 1973-05-10 |
| NL7114238A (OSRAM) | 1972-04-18 |
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