CA1051025A - Process for the purification of decane dicarboxylic acid-(1,10) - Google Patents
Process for the purification of decane dicarboxylic acid-(1,10)Info
- Publication number
- CA1051025A CA1051025A CA225,645A CA225645A CA1051025A CA 1051025 A CA1051025 A CA 1051025A CA 225645 A CA225645 A CA 225645A CA 1051025 A CA1051025 A CA 1051025A
- Authority
- CA
- Canada
- Prior art keywords
- content
- weight
- acid
- dicarboxylic acid
- decreased
- 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
- 238000000034 method Methods 0.000 title claims abstract description 25
- FWQNYUYRXNWOOM-UHFFFAOYSA-N 2-nonylpropanedioic acid Chemical compound CCCCCCCCCC(C(O)=O)C(O)=O FWQNYUYRXNWOOM-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000000746 purification Methods 0.000 title claims abstract description 7
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 30
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 26
- 230000003247 decreasing effect Effects 0.000 claims abstract description 25
- 230000003647 oxidation Effects 0.000 claims abstract description 20
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 16
- SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- SFVWPXMPRCIVOK-UHFFFAOYSA-N cyclododecanol Chemical compound OC1CCCCCCCCCCC1 SFVWPXMPRCIVOK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 230000001590 oxidative effect Effects 0.000 claims abstract description 6
- 238000004821 distillation Methods 0.000 claims description 22
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 21
- 230000007423 decrease Effects 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 239000011552 falling film Substances 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 238000007669 thermal treatment Methods 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 125000001477 organic nitrogen group Chemical group 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 16
- 239000004952 Polyamide Substances 0.000 abstract description 6
- 229920002647 polyamide Polymers 0.000 abstract description 6
- 229920000728 polyester Polymers 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract 1
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 27
- 229940074355 nitric acid Drugs 0.000 description 23
- 239000000047 product Substances 0.000 description 18
- 241001550224 Apha Species 0.000 description 14
- 229960005419 nitrogen Drugs 0.000 description 14
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 8
- 230000009183 running Effects 0.000 description 6
- QJGNSTCICFBACB-UHFFFAOYSA-N 2-octylpropanedioic acid Chemical compound CCCCCCCCC(C(O)=O)C(O)=O QJGNSTCICFBACB-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 230000004927 fusion Effects 0.000 description 4
- 229910001385 heavy metal Inorganic materials 0.000 description 4
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 4
- 239000010408 film Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- XDXHAEQXIBQUEZ-UHFFFAOYSA-N Ropinirole hydrochloride Chemical compound Cl.CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2 XDXHAEQXIBQUEZ-UHFFFAOYSA-N 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002226 simultaneous effect Effects 0.000 description 1
- 150000003681 vanadium Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (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 |
|---|---|---|---|
| DE2420765A DE2420765C3 (de) | 1974-04-29 | 1974-04-29 | Verfahren zur Reinigung von Decandicarbonsäure- (l,lo) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1051025A true CA1051025A (en) | 1979-03-20 |
Family
ID=5914274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA225,645A Expired CA1051025A (en) | 1974-04-29 | 1975-04-28 | Process for the purification of decane dicarboxylic acid-(1,10) |
Country Status (11)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1138090B (it) * | 1980-07-17 | 1986-09-10 | Du Pont | Trattamento di esteri di acidi bibasici con boroidruri,permanganati o metilati di metalli alcalini |
| EP2365017B1 (en) | 2005-04-22 | 2019-07-03 | Mitsubishi Chemical Corporation | Biomass-resource-derived polyester and production process thereof |
| CN101525287B (zh) * | 2008-03-04 | 2012-02-08 | 上海芝东商务咨询有限公司 | 一种癸二酸的精制方法 |
| WO2009117498A2 (en) * | 2008-03-19 | 2009-09-24 | Invista Technologies S.A R.L. | Methods of making cyclododecatriene and methods of making laurolactone |
| US9120685B2 (en) * | 2010-12-14 | 2015-09-01 | Aquatech International Corporation | Method for recycling deoiled water using counterflow falling-film evaporators |
| US12017182B2 (en) | 2019-12-24 | 2024-06-25 | Cathay Biotech Inc. | Method and system for refining long chain dicarboxylic acid |
| CN119504415A (zh) * | 2019-12-24 | 2025-02-25 | 上海凯赛生物技术股份有限公司 | 一种长链二元酸的精制工艺及系统 |
| CN113307532B (zh) * | 2021-06-15 | 2022-04-22 | 西南石油大学 | 一种低温固井用控制水泥水化热的微胶囊的制备方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2522529A (en) * | 1946-01-08 | 1950-09-19 | Robert W Miller | Distillation of alcohols from dibasic acid diesters |
| US2791551A (en) * | 1952-05-01 | 1957-05-07 | Wyandotte Chemicals Corp | Removal of hno3 from carboxymethyl diethers of ethylene glycols |
| US2771482A (en) * | 1953-08-26 | 1956-11-20 | Gulf Research Development Co | Nitric acid oxidation of hydrocarbons |
| US2791598A (en) * | 1953-08-26 | 1957-05-07 | Gulf Research Development Co | Nitric acid oxidation of hydrocarbons |
| US2878276A (en) * | 1955-05-03 | 1959-03-17 | Gulf Research Development Co | Process for producing dibasic carboxylic acids |
| NL289024A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1962-02-19 | |||
| US3402108A (en) * | 1966-07-07 | 1968-09-17 | Emery Industries Inc | Process for the production of a purified grade of azelaic acid by treatment with ozone during purification |
| US3637832A (en) * | 1968-03-12 | 1972-01-25 | Du Pont | Preparation of straight chain dicarboxylic acids |
| DE1919228C3 (de) * | 1969-04-16 | 1984-04-12 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur kontinuierlichen Herstellung von gesättigten aliphatischen Dicarbonsäuren |
| JPS4834578A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1971-09-07 | 1973-05-19 | ||
| DE2217003C2 (de) * | 1972-04-08 | 1983-12-15 | Chemische Werke Hüls AG, 4370 Marl | Verfahren und Vorrichtung zur kontinuierlichen Herstellung von gesättigten aliphatischen Dicarbonsäuren |
| US3903152A (en) * | 1972-07-04 | 1975-09-02 | Toa Gosei Chem Ind | Process for producing highly pure 1,12-dodecanedioic acid |
| US3979450A (en) * | 1973-02-08 | 1976-09-07 | Jury Leonidovich Moskovich | Method for preparing dicarboxylic acids |
-
1974
- 1974-04-29 DE DE2420765A patent/DE2420765C3/de not_active Expired
-
1975
- 1975-04-17 FR FR7511934A patent/FR2268781B1/fr not_active Expired
- 1975-04-23 IT IT49257/75A patent/IT1035434B/it active
- 1975-04-25 JP JP50049859A patent/JPS582217B2/ja not_active Expired
- 1975-04-25 SU SU752127953A patent/SU623516A3/ru active
- 1975-04-28 DD DD185738A patent/DD119410A5/xx unknown
- 1975-04-28 GB GB17484/75A patent/GB1501997A/en not_active Expired
- 1975-04-28 CA CA225,645A patent/CA1051025A/en not_active Expired
- 1975-04-28 BE BE155883A patent/BE828508A/xx unknown
- 1975-04-29 US US05/572,857 patent/US4067779A/en not_active Expired - Lifetime
- 1975-04-29 NL NL7505111A patent/NL7505111A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2420765B2 (de) | 1980-05-29 |
| NL7505111A (nl) | 1975-10-31 |
| FR2268781B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-08-24 |
| IT1035434B (it) | 1979-10-20 |
| BE828508A (fr) | 1975-08-18 |
| FR2268781A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-11-21 |
| US4067779A (en) | 1978-01-10 |
| SU623516A3 (ru) | 1978-09-05 |
| JPS50149616A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-11-29 |
| DD119410A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-04-20 |
| GB1501997A (en) | 1978-02-22 |
| DE2420765A1 (de) | 1975-10-30 |
| JPS582217B2 (ja) | 1983-01-14 |
| DE2420765C3 (de) | 1981-02-12 |
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