CA1066302A - Methode de production d'acides aromatiques - Google Patents

Methode de production d'acides aromatiques

Info

Publication number: CA1066302A
Authority: CA; Canada
Prior art keywords: acid; hydrolysis; equilibrium; reboiler; aromatic
Prior art date: 1976-04-14
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

Application number

CA250,254A

Other languages

English (en)

Inventor

Raymond Wynkoop

Allen W. Hancock (Ii)

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sun Ventures Inc

Original Assignee

Sun Ventures Inc

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.)

1976-04-14

Filing date

1976-04-14

Publication date

1979-11-13

1976-04-14 Application filed by Sun Ventures Inc filed Critical Sun Ventures Inc

1976-04-14 Priority to CA250,254A priority Critical patent/CA1066302A/fr

1979-11-13 Application granted granted Critical

1979-11-13 Publication of CA1066302A publication Critical patent/CA1066302A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 27
159000000032 aromatic acids Chemical class 0.000 title description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 51
230000007062 hydrolysis Effects 0.000 claims abstract description 36
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 36
229910021529 ammonia Inorganic materials 0.000 claims abstract description 25
239000002253 acid Substances 0.000 claims abstract description 23
239000000203 mixture Substances 0.000 claims abstract description 20
238000004821 distillation Methods 0.000 claims abstract description 14
-1 aromatic nitrile Chemical class 0.000 claims abstract description 13
238000000066 reactive distillation Methods 0.000 claims abstract description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 8
150000002825 nitriles Chemical class 0.000 claims abstract description 8
239000007864 aqueous solution Substances 0.000 claims abstract description 5
239000000243 solution Substances 0.000 claims abstract description 5
238000001816 cooling Methods 0.000 claims abstract description 4
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
BHXFKXOIODIUJO-UHFFFAOYSA-N benzene-1,4-dicarbonitrile Chemical group N#CC1=CC=C(C#N)C=C1 BHXFKXOIODIUJO-UHFFFAOYSA-N 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 5
239000012535 impurity Substances 0.000 claims description 4
150000002790 naphthalenes Chemical class 0.000 claims description 4
229920006391 phthalonitrile polymer Polymers 0.000 claims description 4
XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 claims description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 1
239000000047 product Substances 0.000 description 10
150000001408 amides Chemical class 0.000 description 4
150000003863 ammonium salts Chemical class 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000000413 hydrolysate Substances 0.000 description 4
150000007513 acids Chemical class 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
FUKWTMJZHKZKFA-UHFFFAOYSA-N 4-cyanobenzamide Chemical compound NC(=O)C1=CC=C(C#N)C=C1 FUKWTMJZHKZKFA-UHFFFAOYSA-N 0.000 description 1
ADCUEPOHPCPMCE-UHFFFAOYSA-N 4-cyanobenzoic acid Chemical compound OC(=O)C1=CC=C(C#N)C=C1 ADCUEPOHPCPMCE-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
CKOAELPFZQZJHS-UHFFFAOYSA-N [NH4+].NC(=O)C1=CC=C(C([O-])=O)C=C1 Chemical compound [NH4+].NC(=O)C1=CC=C(C([O-])=O)C=C1 CKOAELPFZQZJHS-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
238000010420 art technique Methods 0.000 description 1
XSOHCQBMTDEBAD-UHFFFAOYSA-N azane Chemical compound N.N.N XSOHCQBMTDEBAD-UHFFFAOYSA-N 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229920006158 high molecular weight polymer Polymers 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
ZNPWYAMBOPRTHW-UHFFFAOYSA-N naphthalene-1,2-dicarbonitrile Chemical compound C1=CC=CC2=C(C#N)C(C#N)=CC=C21 ZNPWYAMBOPRTHW-UHFFFAOYSA-N 0.000 description 1
ZBFVJRBOKDTSMO-UHFFFAOYSA-N naphthalene-2,6-dicarbonitrile Chemical compound C1=C(C#N)C=CC2=CC(C#N)=CC=C21 ZBFVJRBOKDTSMO-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
238000001577 simple distillation Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000010408 sweeping Methods 0.000 description 1
MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA250,254A 1976-04-14 1976-04-14 Methode de production d'acides aromatiques Expired CA1066302A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA250,254A CA1066302A (fr)	1976-04-14	1976-04-14	Methode de production d'acides aromatiques

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA250,254A CA1066302A (fr)	1976-04-14	1976-04-14	Methode de production d'acides aromatiques

Publications (1)

Publication Number	Publication Date
CA1066302A true CA1066302A (fr)	1979-11-13

Family

ID=4105714

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA250,254A Expired CA1066302A (fr)	1976-04-14	1976-04-14	Methode de production d'acides aromatiques

Country Status (1)

Country	Link
CA (1)	CA1066302A (fr)

1976
- 1976-04-14 CA CA250,254A patent/CA1066302A/fr not_active Expired

Publication	Publication Date	Title
US2301964A (en)	1942-11-17	Method of preparing lactams
US2768132A (en)	1956-10-23	Process for purification of an adiponitrile
JP2002515478A (ja)	2002-05-28	アミノニトリル及びジアミンの製造方法
KR100527321B1 (ko)	2005-11-09	헥사메틸렌 디아민을 함유하는 혼합물에서 이를 회수하는 방법
CA1065339A (fr)	1979-10-30	Procede pour la fabrication d'acides aromatiques
RU2221770C2 (ru)	2004-01-20	Способ кристаллизации карбоновой кислоты
US3776949A (en)	1973-12-04	Production of aromatic polycarboxylic acids
US4551208A (en)	1985-11-05	Recovery of formic acid by distillation
JP3579428B2 (ja)	2004-10-20	ラクタムの処理法
US6252115B1 (en)	2001-06-26	Method for separating an imine from a mixture containing an amine and an imine
CA2247463A1 (fr)	1997-08-28	Procede de preparation de .epsilon.-caprolactame a partir de l'acide 6-aminocaproique
US4069248A (en)	1978-01-17	Hydrolysis of aromatic nitriles to carboxylic acids
US3781343A (en)	1973-12-25	Hydrolysis of aromatic dinitriles
KR100480409B1 (ko)	2005-04-06	헥사메틸렌디아민 및 2-아미노메틸시클로펜틸아민 함유 혼합물로 부터 2-아미노메틸시클로펜틸아민의 분리 방법
WO2003097583A1 (fr)	2003-11-27	Ammoxydation d'acides carboxyliques en un melange de nitriles
US4086270A (en)	1978-04-25	Process for making terephthalic acid
CA1126762A (fr)	1982-06-29	Hydrogenation de dinitriles aromatiques
DE2241365A1 (de)	1973-03-08	Verfahren zur dampfphasenammonoxydation von m-xylol zu isophthalonitril
US3873610A (en)	1975-03-25	Process for aromatic carboxylic acids
JPH01190667A (ja)	1989-07-31	Ｎ−メチル−２−ピロリドンの製造方法
US3123632A (en)	1964-03-03	Process for the production of the
GB1570076A (en)	1980-06-25	Process for making aromatic acids
US3839402A (en)	1974-10-01	Purification of aromatic nitriles
US4220592A (en)	1980-09-02	Synthesis of substituted phenylacetic acid
CA2407812C (fr)	2008-12-02	Procede pour la production de lactames cycliques