UA73646C2 - A method for the preparation of alkanedicarboxylic acid - Google Patents
A method for the preparation of alkanedicarboxylic acid Download PDFInfo
- Publication number
- UA73646C2 UA73646C2 UA2003087999A UA2003087999A UA73646C2 UA 73646 C2 UA73646 C2 UA 73646C2 UA 2003087999 A UA2003087999 A UA 2003087999A UA 2003087999 A UA2003087999 A UA 2003087999A UA 73646 C2 UA73646 C2 UA 73646C2
- Authority
- UA
- Ukraine
- Prior art keywords
- nitric acid
- specified
- acid
- reactor
- temperature
- Prior art date
Links
- 239000002253 acid Substances 0.000 title abstract description 46
- 238000000034 method Methods 0.000 title abstract description 29
- 238000002360 preparation method Methods 0.000 title description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract description 146
- 229910017604 nitric acid Inorganic materials 0.000 abstract description 146
- 238000002156 mixing Methods 0.000 abstract description 84
- 230000001590 oxidative effect Effects 0.000 abstract description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 84
- 239000007864 aqueous solution Substances 0.000 description 49
- 238000006243 chemical reaction Methods 0.000 description 49
- 239000001361 adipic acid Substances 0.000 description 42
- 235000011037 adipic acid Nutrition 0.000 description 42
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 39
- 230000003068 static effect Effects 0.000 description 26
- 239000000243 solution Substances 0.000 description 25
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 23
- 238000002425 crystallisation Methods 0.000 description 21
- 230000008025 crystallization Effects 0.000 description 21
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 20
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 14
- 238000007254 oxidation reaction Methods 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 238000003795 desorption Methods 0.000 description 12
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 7
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 7
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 7
- 239000001272 nitrous oxide Substances 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000009529 body temperature measurement Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- SETMGIIITGNLAS-UHFFFAOYSA-N spizofurone Chemical compound O=C1C2=CC(C(=O)C)=CC=C2OC21CC2 SETMGIIITGNLAS-UHFFFAOYSA-N 0.000 description 3
- 229950001870 spizofurone Drugs 0.000 description 3
- SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241001611408 Nebo Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 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
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- SFVWPXMPRCIVOK-UHFFFAOYSA-N cyclododecanol Chemical compound OC1CCCCCCCCCCC1 SFVWPXMPRCIVOK-UHFFFAOYSA-N 0.000 description 1
- FHADSMKORVFYOS-UHFFFAOYSA-N cyclooctanol Chemical compound OC1CCCCCCC1 FHADSMKORVFYOS-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- LZDSILRDTDCIQT-UHFFFAOYSA-N dinitrogen trioxide Chemical compound [O-][N+](=O)N=O LZDSILRDTDCIQT-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 235000013842 nitrous oxide Nutrition 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 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
-
- 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)
- Physical Or Chemical Processes And Apparatus (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001016819 | 2001-01-25 | ||
| PCT/JP2002/000513 WO2002059071A1 (fr) | 2001-01-25 | 2002-01-24 | Procédé de production d'un acide alcanedicarboxylique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA73646C2 true UA73646C2 (en) | 2005-08-15 |
Family
ID=18883121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2003087999A UA73646C2 (en) | 2001-01-25 | 2002-01-24 | A method for the preparation of alkanedicarboxylic acid |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7019167B2 (zh) |
| EP (1) | EP1354866B1 (zh) |
| JP (1) | JP4004407B2 (zh) |
| KR (1) | KR100527655B1 (zh) |
| CN (1) | CN1221508C (zh) |
| AT (1) | ATE486837T1 (zh) |
| BR (1) | BR0206659B1 (zh) |
| CA (1) | CA2434894C (zh) |
| DE (1) | DE60238176D1 (zh) |
| MY (1) | MY136690A (zh) |
| TW (1) | TWI238157B (zh) |
| UA (1) | UA73646C2 (zh) |
| WO (1) | WO2002059071A1 (zh) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101190784B (zh) * | 2006-11-22 | 2010-08-11 | 中国石油天然气股份有限公司 | 己二酸生产中稀硝酸浓缩方法 |
| FR2939131B1 (fr) * | 2008-12-01 | 2010-12-17 | Rhodia Operations | Procede de fabrication d'acide adipique |
| FR2939052B1 (fr) * | 2008-12-01 | 2010-12-10 | Rhodia Operations | Installation de cristallisation d'acide adipique |
| GB201019701D0 (en) * | 2010-11-19 | 2011-01-05 | Invista Tech Sarl | Reaction process |
| WO2013008637A1 (ja) * | 2011-07-12 | 2013-01-17 | 旭化成ケミカルズ株式会社 | シクロヘキサノール、シクロヘキサノールの製造方法及びアジピン酸の製造方法 |
| CN104478702B (zh) * | 2014-11-24 | 2018-01-05 | 常州大学 | 一种采用微通道反应器合成己二酸的方法 |
| CN104478701B (zh) * | 2014-11-24 | 2016-08-24 | 常州大学 | 连续流微通道反应器中醇酮油硝酸氧化合成己二酸的方法 |
| CN107108414A (zh) | 2014-12-22 | 2017-08-29 | 罗地亚经营管理公司 | 环烷烃氧化催化剂以及生产醇和酮的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR86366E (zh) * | 1961-08-25 | 1966-04-08 | ||
| US3359308A (en) | 1963-05-17 | 1967-12-19 | Du Pont | Preparation of dicarboxylic acids by nitric acid oxidation |
| DE1238000C2 (de) | 1964-03-11 | 1980-06-26 | Basf Ag, 6700 Ludwigshafen | Verfahren zur kontinuierlichen herstellung von gesaettigten aliphatischen dicarbonsaeuren |
| GB1511438A (en) * | 1976-04-12 | 1978-05-17 | Ici Ltd | Treatment of residues from the oxidation process for the preparation of adipic acid |
| JPS61257940A (ja) | 1985-05-13 | 1986-11-15 | Asahi Chem Ind Co Ltd | ジカルボン酸の製造法 |
-
2002
- 2002-01-22 TW TW091100977A patent/TWI238157B/zh not_active IP Right Cessation
- 2002-01-24 BR BRPI0206659-9A patent/BR0206659B1/pt not_active IP Right Cessation
- 2002-01-24 AT AT02716362T patent/ATE486837T1/de not_active IP Right Cessation
- 2002-01-24 CA CA002434894A patent/CA2434894C/en not_active Expired - Lifetime
- 2002-01-24 DE DE60238176T patent/DE60238176D1/de not_active Expired - Lifetime
- 2002-01-24 JP JP2002559376A patent/JP4004407B2/ja not_active Expired - Lifetime
- 2002-01-24 MY MYPI20020267A patent/MY136690A/en unknown
- 2002-01-24 KR KR10-2003-7009855A patent/KR100527655B1/ko active IP Right Grant
- 2002-01-24 EP EP02716362A patent/EP1354866B1/en not_active Expired - Lifetime
- 2002-01-24 US US10/470,163 patent/US7019167B2/en not_active Expired - Lifetime
- 2002-01-24 UA UA2003087999A patent/UA73646C2/uk unknown
- 2002-01-24 CN CNB028040414A patent/CN1221508C/zh not_active Expired - Lifetime
- 2002-01-24 WO PCT/JP2002/000513 patent/WO2002059071A1/ja active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| EP1354866A4 (en) | 2005-05-11 |
| MY136690A (en) | 2008-11-28 |
| CN1487914A (zh) | 2004-04-07 |
| EP1354866A1 (en) | 2003-10-22 |
| EP1354866B1 (en) | 2010-11-03 |
| WO2002059071A1 (fr) | 2002-08-01 |
| CN1221508C (zh) | 2005-10-05 |
| CA2434894A1 (en) | 2002-08-01 |
| DE60238176D1 (de) | 2010-12-16 |
| ATE486837T1 (de) | 2010-11-15 |
| JP4004407B2 (ja) | 2007-11-07 |
| BR0206659B1 (pt) | 2012-08-21 |
| CA2434894C (en) | 2008-02-19 |
| KR20030074738A (ko) | 2003-09-19 |
| TWI238157B (en) | 2005-08-21 |
| BR0206659A (pt) | 2004-02-03 |
| US7019167B2 (en) | 2006-03-28 |
| KR100527655B1 (ko) | 2005-11-09 |
| JPWO2002059071A1 (ja) | 2004-05-27 |
| US20040073061A1 (en) | 2004-04-15 |
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