DE2233590C2 - Verfahren zur Herstellung von geradkettigen Alkandicarbonsäuren mit 4 bis 12 C-Atomen - Google Patents
Verfahren zur Herstellung von geradkettigen Alkandicarbonsäuren mit 4 bis 12 C-AtomenInfo
- Publication number
- DE2233590C2 DE2233590C2 DE2233590A DE2233590A DE2233590C2 DE 2233590 C2 DE2233590 C2 DE 2233590C2 DE 2233590 A DE2233590 A DE 2233590A DE 2233590 A DE2233590 A DE 2233590A DE 2233590 C2 DE2233590 C2 DE 2233590C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- mother liquor
- oxidation
- urea
- alcohol
- 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
- 239000002253 acid Substances 0.000 title claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 9
- 150000007513 acids Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims 4
- 239000012452 mother liquor Substances 0.000 claims description 23
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 17
- 239000004202 carbamide Substances 0.000 claims description 17
- 229910017604 nitric acid Inorganic materials 0.000 claims description 17
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 17
- 230000003647 oxidation Effects 0.000 claims description 16
- 238000007254 oxidation reaction Methods 0.000 claims description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 229910001868 water Inorganic materials 0.000 claims description 9
- SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- 150000002576 ketones Chemical class 0.000 claims description 7
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 claims description 4
- SFVWPXMPRCIVOK-UHFFFAOYSA-N cyclododecanol Chemical compound OC1CCCCCCCCCCC1 SFVWPXMPRCIVOK-UHFFFAOYSA-N 0.000 claims description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 230000000977 initiatory effect Effects 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 6
- 150000003997 cyclic ketones Chemical class 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 230000001590 oxidative effect Effects 0.000 claims 3
- 238000004064 recycling Methods 0.000 claims 3
- 238000000926 separation method Methods 0.000 claims 3
- DDTBPAQBQHZRDW-UHFFFAOYSA-N cyclododecane Chemical compound C1CCCCCCCCCCC1 DDTBPAQBQHZRDW-UHFFFAOYSA-N 0.000 claims 2
- BAUZLFKYYIVGPM-UHFFFAOYSA-N cyclononanone Chemical compound O=C1CCCCCCCC1 BAUZLFKYYIVGPM-UHFFFAOYSA-N 0.000 claims 2
- 239000007791 liquid phase Substances 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- WTKWFNIIIXNTDO-UHFFFAOYSA-N 3-isocyanato-5-methyl-2-(trifluoromethyl)furan Chemical compound CC1=CC(N=C=O)=C(C(F)(F)F)O1 WTKWFNIIIXNTDO-UHFFFAOYSA-N 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 238000009825 accumulation Methods 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 230000015556 catabolic process Effects 0.000 claims 1
- 239000004927 clay Substances 0.000 claims 1
- 238000010924 continuous production Methods 0.000 claims 1
- WFRBMXFCEAHLGH-UHFFFAOYSA-N cyclodecanol Chemical compound OC1CCCCCCCCC1 WFRBMXFCEAHLGH-UHFFFAOYSA-N 0.000 claims 1
- FHADSMKORVFYOS-UHFFFAOYSA-N cyclooctanol Chemical compound OC1CCCCCCC1 FHADSMKORVFYOS-UHFFFAOYSA-N 0.000 claims 1
- IIRFCWANHMSDCG-UHFFFAOYSA-N cyclooctanone Chemical compound O=C1CCCCCCC1 IIRFCWANHMSDCG-UHFFFAOYSA-N 0.000 claims 1
- UPOSSYJVWXLPTA-UHFFFAOYSA-N cycloundecanone Chemical compound O=C1CCCCCCCCCC1 UPOSSYJVWXLPTA-UHFFFAOYSA-N 0.000 claims 1
- JDPQWHLMBJZURR-UHFFFAOYSA-N decan-5-one Chemical compound CCCCCC(=O)CCCC JDPQWHLMBJZURR-UHFFFAOYSA-N 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 238000006731 degradation reaction Methods 0.000 claims 1
- 238000012217 deletion Methods 0.000 claims 1
- 230000037430 deletion Effects 0.000 claims 1
- 239000003344 environmental pollutant Substances 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 231100001261 hazardous Toxicity 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- ZAJNGDIORYACQU-UHFFFAOYSA-N methyl n-octyl ketone Natural products CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 claims 1
- TVIDDXQYHWJXFK-UHFFFAOYSA-N n-Dodecanedioic acid Natural products OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 claims 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- 231100000719 pollutant Toxicity 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 239000002516 radical scavenger Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000007670 refining Methods 0.000 claims 1
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Natural products OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 claims 1
- 210000002700 urine Anatomy 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- 239000007788 liquid Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 3
- -1 Nftriumnitrlt Chemical compound 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- IDNHOWMYUQKKTI-UHFFFAOYSA-M lithium nitrite Chemical compound [Li+].[O-]N=O IDNHOWMYUQKKTI-UHFFFAOYSA-M 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003681 vanadium Chemical class 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16075771A | 1971-07-08 | 1971-07-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2233590A1 DE2233590A1 (de) | 1973-01-25 |
| DE2233590C2 true DE2233590C2 (de) | 1984-07-19 |
Family
ID=22578306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2233590A Expired DE2233590C2 (de) | 1971-07-08 | 1972-07-07 | Verfahren zur Herstellung von geradkettigen Alkandicarbonsäuren mit 4 bis 12 C-Atomen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3758564A (https=) |
| JP (1) | JPS5629650B1 (https=) |
| BE (1) | BE785993A (https=) |
| CA (1) | CA985703A (https=) |
| DE (1) | DE2233590C2 (https=) |
| FR (1) | FR2144887B1 (https=) |
| GB (1) | GB1371721A (https=) |
| IT (1) | IT962648B (https=) |
| NL (1) | NL179648C (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4014903A (en) * | 1975-08-11 | 1977-03-29 | Allied Chemical Corporation | Recovery of dicarboxylic acids from aqueous solution containing nitric acid |
| JPS60146562U (ja) * | 1984-03-09 | 1985-09-28 | 新日本製鐵株式会社 | タンデイツシユ用カセツト式フイルタ− |
| DE10215943B4 (de) * | 2002-04-11 | 2006-10-26 | Degussa Ag | Aufarbeitung von Rückständen bei der Herstellung von Carbonsäuren |
| EP2257516A4 (en) * | 2008-03-19 | 2012-12-12 | Invista Tech Sarl | METHODS FOR PREPARING CYCLODODECATRIENE AND METHODS FOR PREPARING LAUROLACTONE |
| CN108017533B (zh) * | 2016-11-01 | 2021-05-14 | 万华化学集团股份有限公司 | 一种制备十二碳二酸的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3637832A (en) * | 1968-03-12 | 1972-01-25 | Du Pont | Preparation of straight chain dicarboxylic acids |
-
1971
- 1971-07-08 US US00160757A patent/US3758564A/en not_active Expired - Lifetime
-
1972
- 1972-07-04 CA CA146,320A patent/CA985703A/en not_active Expired
- 1972-07-07 DE DE2233590A patent/DE2233590C2/de not_active Expired
- 1972-07-07 IT IT26779/72A patent/IT962648B/it active
- 1972-07-07 FR FR7224771A patent/FR2144887B1/fr not_active Expired
- 1972-07-07 JP JP6759072A patent/JPS5629650B1/ja active Pending
- 1972-07-07 NL NLAANVRAGE7209505,A patent/NL179648C/xx not_active IP Right Cessation
- 1972-07-07 BE BE785993A patent/BE785993A/xx not_active IP Right Cessation
- 1972-07-07 GB GB3188772A patent/GB1371721A/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| IT962648B (it) | 1973-12-31 |
| FR2144887A1 (https=) | 1973-02-16 |
| DE2233590A1 (de) | 1973-01-25 |
| JPS5629650B1 (https=) | 1981-07-09 |
| NL7209505A (https=) | 1973-01-10 |
| GB1371721A (en) | 1974-10-23 |
| NL179648C (nl) | 1986-10-16 |
| BE785993A (fr) | 1972-11-03 |
| FR2144887B1 (https=) | 1974-10-04 |
| US3758564A (en) | 1973-09-11 |
| CA985703A (en) | 1976-03-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |