UA73646C2 - A method for the preparation of alkanedicarboxylic acid - Google Patents

A method for the preparation of alkanedicarboxylic acid Download PDF

Info

Publication number: UA73646C2
Authority: UA; Ukraine
Prior art keywords: nitric acid; specified; acid; reactor; temperature
Prior art date: 2001-01-25

Application number

UA2003087999A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Asahi Chemical Ind

Priority date (The priority date 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 date listed.)

2001-01-25

Filing date

2002-01-24

Publication date

2005-08-15

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=18883121&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=UA73646(C2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2002-01-24 Application filed by Asahi Chemical Ind filed Critical Asahi Chemical Ind

2005-08-15 Publication of UA73646C2 publication Critical patent/UA73646C2/uk

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)

UA2003087999A 2001-01-25 2002-01-24 A method for the preparation of alkanedicarboxylic acid UA73646C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP2001016819		2001-01-25
PCT/JP2002/000513 WO2002059071A1 (en)	2001-01-25	2002-01-24	Process for producing alkanedicarboxylic acid

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 (de)
EP (1)	EP1354866B1 (de)
JP (1)	JP4004407B2 (de)
KR (1)	KR100527655B1 (de)
CN (1)	CN1221508C (de)
AT (1)	ATE486837T1 (de)
BR (1)	BR0206659B1 (de)
CA (1)	CA2434894C (de)
DE (1)	DE60238176D1 (de)
MY (1)	MY136690A (de)
TW (1)	TWI238157B (de)
UA (1)	UA73646C2 (de)
WO (1)	WO2002059071A1 (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
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
FR2939052B1 (fr) *	2008-12-01	2010-12-10	Rhodia Operations	Installation de cristallisation d'acide adipique
FR2939131B1 (fr) *	2008-12-01	2010-12-17	Rhodia Operations	Procede de fabrication d'acide adipique
GB201019701D0 (en) *	2010-11-19	2011-01-05	Invista Tech Sarl	Reaction process
KR101554409B1 (ko)	2011-07-12	2015-09-18	아사히 가세이 케미칼즈 가부시키가이샤	시클로헥산올, 시클로헥산올의 제조 방법 및 아디프산의 제조 방법
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
CN112961032A (zh) *	2014-12-22	2021-06-15	高性能聚酰胺有限公司	环烷烃氧化催化剂以及生产醇和酮的方法
HUE071121T2 (hu) *	2018-04-19	2025-08-28	Novoloop Inc	Eljárások szennyezett mûanyaghulladék lebontására

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR86366E (de) *	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 EP EP02716362A patent/EP1354866B1/de not_active Expired - Lifetime
- 2002-01-24 UA UA2003087999A patent/UA73646C2/uk unknown
- 2002-01-24 JP JP2002559376A patent/JP4004407B2/ja not_active Expired - Lifetime
- 2002-01-24 BR BRPI0206659-9A patent/BR0206659B1/pt not_active IP Right Cessation
- 2002-01-24 DE DE60238176T patent/DE60238176D1/de not_active Expired - Lifetime
- 2002-01-24 WO PCT/JP2002/000513 patent/WO2002059071A1/ja not_active Ceased
- 2002-01-24 CA CA002434894A patent/CA2434894C/en not_active Expired - Lifetime
- 2002-01-24 KR KR10-2003-7009855A patent/KR100527655B1/ko not_active Expired - Lifetime
- 2002-01-24 MY MYPI20020267A patent/MY136690A/en unknown
- 2002-01-24 AT AT02716362T patent/ATE486837T1/de not_active IP Right Cessation
- 2002-01-24 US US10/470,163 patent/US7019167B2/en not_active Expired - Lifetime
- 2002-01-24 CN CNB028040414A patent/CN1221508C/zh not_active Expired - Lifetime

Also Published As

Publication number	Publication date
EP1354866A4 (de)	2005-05-11
JPWO2002059071A1 (ja)	2004-05-27
EP1354866B1 (de)	2010-11-03
CN1487914A (zh)	2004-04-07
BR0206659A (pt)	2004-02-03
ATE486837T1 (de)	2010-11-15
TWI238157B (en)	2005-08-21
US7019167B2 (en)	2006-03-28
DE60238176D1 (de)	2010-12-16
CN1221508C (zh)	2005-10-05
MY136690A (en)	2008-11-28
WO2002059071A1 (en)	2002-08-01
US20040073061A1 (en)	2004-04-15
EP1354866A1 (de)	2003-10-22
JP4004407B2 (ja)	2007-11-07
KR100527655B1 (ko)	2005-11-09
BR0206659B1 (pt)	2012-08-21
CA2434894C (en)	2008-02-19
KR20030074738A (ko)	2003-09-19
CA2434894A1 (en)	2002-08-01

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