HU191909B - Process for production of 3,4,5-trimetoxi-benzonitril - Google Patents

Process for production of 3,4,5-trimetoxi-benzonitril Download PDF

Info

Publication number: HU191909B
Authority: HU; Hungary
Prior art keywords: trimethoxybenzonitrile; acid; trimethoxybenzoic acid; urea; trimethoxy
Prior art date: 1983-12-23

Application number

HU834438A

Other languages

English (en)

Hungarian (hu)

Other versions

HUT36085A (en

Inventor

Istvan Orban

Ferenc Nagy

Gyoezoene Molnarka

Tibor Galambos

Kalman Nagy

Laszlo Boda

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

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.)

1983-12-23

Filing date

1983-12-23

Publication date

1987-04-28

1983-12-23 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1983-12-23 Priority to HU834438A priority Critical patent/HU191909B/hu

1984-12-17 Priority to BE1/11154A priority patent/BE901284A/fr

1984-12-20 Priority to CH6072/84A priority patent/CH660730A5/de

1984-12-21 Priority to RO116816A priority patent/RO92934B/ro

1984-12-21 Priority to ES538924A priority patent/ES8600735A1/es

1984-12-21 Priority to FR8419641A priority patent/FR2557106A1/fr

1984-12-21 Priority to CS8410244A priority patent/CS1024484A2/cs

1984-12-21 Priority to JP59268716A priority patent/JPS60214767A/ja

1984-12-21 Priority to IT24230/84A priority patent/IT1178793B/it

1984-12-21 Priority to PL25114484A priority patent/PL251144A1/xx

1984-12-21 Priority to FI845107A priority patent/FI845107L/fi

1984-12-21 Priority to NL8403885A priority patent/NL8403885A/nl

1984-12-21 Priority to SE8406578A priority patent/SE8406578L/xx

1984-12-21 Priority to DE19843446871 priority patent/DE3446871A1/de

1984-12-21 Priority to GB08432498A priority patent/GB2151626B/en

1984-12-21 Priority to SU847773698A priority patent/SU1452477A3/ru

1985-04-01 Priority to CN198585101310A priority patent/CN85101310A/zh

1985-08-28 Publication of HUT36085A publication Critical patent/HUT36085A/hu

1987-04-28 Publication of HU191909B publication Critical patent/HU191909B/hu

Links

238000000034 method Methods 0.000 title claims abstract description 45
238000004519 manufacturing process Methods 0.000 title description 4
SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 claims abstract description 50
OSBQUSPVORCDCU-UHFFFAOYSA-N 3,4,5-trimethoxybenzonitrile Chemical compound COC1=CC(C#N)=CC(OC)=C1OC OSBQUSPVORCDCU-UHFFFAOYSA-N 0.000 claims abstract description 34
IWPZKOJSYQZABD-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Natural products COC1=CC(OC)=CC(C(O)=O)=C1 IWPZKOJSYQZABD-UHFFFAOYSA-N 0.000 claims abstract description 25
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 18
239000004202 carbamide Substances 0.000 claims abstract description 11
238000002360 preparation method Methods 0.000 claims abstract description 11
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 10
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 8
-1 3,4,5-trimethoxybenzonitrile 3.4.5-trimethoxybenzoic acid Chemical compound 0.000 claims description 5
239000000706 filtrate Substances 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
238000001704 evaporation Methods 0.000 claims description 2
230000008020 evaporation Effects 0.000 claims description 2
238000000605 extraction Methods 0.000 claims description 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
238000011084 recovery Methods 0.000 claims 1
125000003944 tolyl group Chemical group 0.000 claims 1
239000000126 substance Substances 0.000 abstract description 3
238000011065 in-situ storage Methods 0.000 abstract description 2
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 abstract 2
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 abstract 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 1
OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
235000013877 carbamide Nutrition 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000005119 centrifugation Methods 0.000 description 5
GGNMTJKRHHLJHH-UHFFFAOYSA-N Trimethylaethergallussaeure-amid Natural products COC1=CC(C(N)=O)=CC(OC)=C1OC GGNMTJKRHHLJHH-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
230000003213 activating effect Effects 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 2
229910000388 diammonium phosphate Inorganic materials 0.000 description 2
235000019838 diammonium phosphate Nutrition 0.000 description 2
230000007613 environmental effect Effects 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
150000002611 lead compounds Chemical class 0.000 description 2
239000000203 mixture Substances 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000000047 product Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000002002 slurry Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 2
QVZGKUBQTJBLKI-WDZFZDKYSA-N (nz)-n-[(3,4,5-trimethoxyphenyl)methylidene]hydroxylamine Chemical compound COC1=CC(\C=N/O)=CC(OC)=C1OC QVZGKUBQTJBLKI-WDZFZDKYSA-N 0.000 description 1
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
241000243320 Hydrozoa Species 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004880 explosion Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
239000000383 hazardous chemical Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
VRNINGUKUJWZTH-UHFFFAOYSA-L lead(2+);dithiocyanate Chemical compound [Pb+2].[S-]C#N.[S-]C#N VRNINGUKUJWZTH-UHFFFAOYSA-L 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
239000012071 phase Substances 0.000 description 1
LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
229960001082 trimethoprim Drugs 0.000 description 1
231100000925 very toxic Toxicity 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

HU834438A 1983-12-23 1983-12-23 Process for production of 3,4,5-trimetoxi-benzonitril HU191909B (en)

Priority Applications (17)

Application Number	Priority Date	Filing Date	Title
HU834438A HU191909B (en)	1983-12-23	1983-12-23	Process for production of 3,4,5-trimetoxi-benzonitril
BE1/11154A BE901284A (fr)	1983-12-23	1984-12-17	Procede pour la preparation de 3,4,5-trimethoxy-benzonitrile.
CH6072/84A CH660730A5 (de)	1983-12-23	1984-12-20	Verfahren zur herstellung von 3,4,5-trimethoxy-benzonitril.
RO116816A RO92934B (ro)	1983-12-23	1984-12-21	Procedeu pentru prepararea 3,4,5-trimetoxibenzonitrilului
ES538924A ES8600735A1 (es)	1983-12-23	1984-12-21	Procedimiento para la preparacion de 3,4,5-trimetoxi-benzonitrilo
FR8419641A FR2557106A1 (fr)	1983-12-23	1984-12-21	Procede pour la preparation de 3,4,5-trimethoxy-benzonitrile
CS8410244A CS1024484A2 (en)	1983-12-23	1984-12-21	Zpusob vyroby 3,4,5 trimethoxybenzonitrilu
JP59268716A JPS60214767A (ja)	1983-12-23	1984-12-21	３，４，５−トリメトキシベンゾニトリルの製造方法
IT24230/84A IT1178793B (it)	1983-12-23	1984-12-21	Procedimento per la preparazione di 3,4,5-trimetossi-benzonitrile
PL25114484A PL251144A1 (en)	1983-12-23	1984-12-21	Method of obtaining 3,4,5-trimethoxybenzonitrile
FI845107A FI845107L (fi)	1983-12-23	1984-12-21	Foerfarande foer framstaellning av 3,4,5-trimetoxibensonitril.
NL8403885A NL8403885A (nl)	1983-12-23	1984-12-21	Werkwijze voor de bereiding van 3,4,5-trimethoxy-benzonitril.
SE8406578A SE8406578L (sv)	1983-12-23	1984-12-21	Forfarande for framstellning av 3,4,5-trimetoxi-bensonitril
DE19843446871 DE3446871A1 (de)	1983-12-23	1984-12-21	Verfahren zur herstellung von 3,4,5-tri-(methoxy)-benzonitril
GB08432498A GB2151626B (en)	1983-12-23	1984-12-21	Process for the preparation of 3,4,5-trimethoxy-benzonitrile
SU847773698A SU1452477A3 (ru)	1983-12-23	1984-12-21	Способ получени 3,4,5-триметоксибензонитрила
CN198585101310A CN85101310A (zh)	1983-12-23	1985-04-01	3，4，5-三甲氧基苯甲腈的制法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU834438A HU191909B (en)	1983-12-23	1983-12-23	Process for production of 3,4,5-trimetoxi-benzonitril

Publications (2)

Publication Number	Publication Date
HUT36085A HUT36085A (en)	1985-08-28
HU191909B true HU191909B (en)	1987-04-28

Family

ID=10967960

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU834438A HU191909B (en)	1983-12-23	1983-12-23	Process for production of 3,4,5-trimetoxi-benzonitril

Country Status (17)

Country	Link
JP (1)	JPS60214767A (it)
CN (1)	CN85101310A (it)
BE (1)	BE901284A (it)
CH (1)	CH660730A5 (it)
CS (1)	CS1024484A2 (it)
DE (1)	DE3446871A1 (it)
ES (1)	ES8600735A1 (it)
FI (1)	FI845107L (it)
FR (1)	FR2557106A1 (it)
GB (1)	GB2151626B (it)
HU (1)	HU191909B (it)
IT (1)	IT1178793B (it)
NL (1)	NL8403885A (it)
PL (1)	PL251144A1 (it)
RO (1)	RO92934B (it)
SE (1)	SE8406578L (it)
SU (1)	SU1452477A3 (it)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN103772236B (zh) *	2014-01-15	2016-04-13	华侨大学	一种苯甲腈衍生物的制备方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH494210A (de) *	1968-03-27	1970-07-31	Sandoz Ag	Verfahren zur Herstellung von Nitrilen
JPS5476544A (en) *	1977-11-26	1979-06-19	Sumitomo Chem Co Ltd	Preparation of p-cyanophenol
JPS5495541A (en) *	1978-01-06	1979-07-28	Sumitomo Chem Co Ltd	Production of cyanophenol

1983
- 1983-12-23 HU HU834438A patent/HU191909B/hu not_active IP Right Cessation
1984
- 1984-12-17 BE BE1/11154A patent/BE901284A/fr not_active IP Right Cessation
- 1984-12-20 CH CH6072/84A patent/CH660730A5/de not_active IP Right Cessation
- 1984-12-21 SE SE8406578A patent/SE8406578L/xx not_active Application Discontinuation
- 1984-12-21 SU SU847773698A patent/SU1452477A3/ru active
- 1984-12-21 JP JP59268716A patent/JPS60214767A/ja active Pending
- 1984-12-21 NL NL8403885A patent/NL8403885A/nl not_active Application Discontinuation
- 1984-12-21 FI FI845107A patent/FI845107L/fi not_active Application Discontinuation
- 1984-12-21 GB GB08432498A patent/GB2151626B/en not_active Expired
- 1984-12-21 IT IT24230/84A patent/IT1178793B/it active
- 1984-12-21 DE DE19843446871 patent/DE3446871A1/de not_active Withdrawn
- 1984-12-21 RO RO116816A patent/RO92934B/ro unknown
- 1984-12-21 CS CS8410244A patent/CS1024484A2/cs unknown
- 1984-12-21 FR FR8419641A patent/FR2557106A1/fr active Pending
- 1984-12-21 PL PL25114484A patent/PL251144A1/xx unknown
- 1984-12-21 ES ES538924A patent/ES8600735A1/es not_active Expired
1985
- 1985-04-01 CN CN198585101310A patent/CN85101310A/zh active Pending

Also Published As

Publication number	Publication date
FI845107L (fi)	1985-06-24
FR2557106A1 (fr)	1985-06-28
FI845107A0 (fi)	1984-12-21
IT1178793B (it)	1987-09-16
CH660730A5 (de)	1987-06-15
ES538924A0 (es)	1985-11-01
CN85101310A (zh)	1987-01-24
PL251144A1 (en)	1985-10-08
DE3446871A1 (de)	1985-07-11
SU1452477A3 (ru)	1989-01-15
IT8424230A0 (it)	1984-12-21
RO92934A (ro)	1987-12-31
SE8406578D0 (sv)	1984-12-21
GB2151626A (en)	1985-07-24
GB2151626B (en)	1987-04-29
GB8432498D0 (en)	1985-02-06
CS1024484A2 (en)	1988-07-15
BE901284A (fr)	1985-06-17
RO92934B (ro)	1988-01-01
HUT36085A (en)	1985-08-28
SE8406578L (sv)	1985-06-24
ES8600735A1 (es)	1985-11-01
NL8403885A (nl)	1985-07-16
JPS60214767A (ja)	1985-10-28

Legal Events

Date	Code	Title	Description
1990-06-28	HU90	Patent valid on 900628
1999-08-30	HMM4	Cancellation of final prot. due to non-payment of fee

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