CA2359459A1 - Method for the preparation of azoiminoethers and of azocarboxylic acid esters, and novel mixed esters of azocarboxylic acids - Google Patents
Method for the preparation of azoiminoethers and of azocarboxylic acid esters, and novel mixed esters of azocarboxylic acids Download PDFInfo
- Publication number
- CA2359459A1 CA2359459A1 CA002359459A CA2359459A CA2359459A1 CA 2359459 A1 CA2359459 A1 CA 2359459A1 CA 002359459 A CA002359459 A CA 002359459A CA 2359459 A CA2359459 A CA 2359459A CA 2359459 A1 CA2359459 A1 CA 2359459A1
- Authority
- CA
- Canada
- Prior art keywords
- alcohol
- preparation
- ester
- azoiminoether
- azocarboxylic
- 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.)
- Abandoned
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 64
- 238000000034 method Methods 0.000 title claims abstract description 57
- 239000002253 acid Substances 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims description 40
- 150000007513 acids Chemical class 0.000 title description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 103
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 84
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 72
- 239000000203 mixture Substances 0.000 claims abstract description 59
- 239000007788 liquid Substances 0.000 claims abstract description 22
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 17
- 230000007062 hydrolysis Effects 0.000 claims abstract description 16
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 16
- 239000003849 aromatic solvent Substances 0.000 claims abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 150000002367 halogens Chemical group 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 17
- 150000001298 alcohols Chemical class 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000012074 organic phase Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 238000001914 filtration Methods 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 238000011065 in-situ storage Methods 0.000 claims description 7
- -1 methyl butyl Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000004494 ethyl ester group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 238000002955 isolation Methods 0.000 claims description 5
- 239000003999 initiator Substances 0.000 claims description 4
- 239000003505 polymerization initiator Substances 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- MVPPADPHJFYWMZ-IDEBNGHGSA-N chlorobenzene Chemical group Cl[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 MVPPADPHJFYWMZ-IDEBNGHGSA-N 0.000 claims 1
- JSLCOZYBKYHZNL-UHFFFAOYSA-N isobutyric acid butyl ester Natural products CCCCOC(=O)C(C)C JSLCOZYBKYHZNL-UHFFFAOYSA-N 0.000 claims 1
- RGFNRWTWDWVHDD-UHFFFAOYSA-N sec-butyl ester of butyric acid Natural products CCCC(=O)OCC(C)C RGFNRWTWDWVHDD-UHFFFAOYSA-N 0.000 claims 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 11
- 238000001816 cooling Methods 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 239000008346 aqueous phase Substances 0.000 description 9
- 239000012467 final product Substances 0.000 description 8
- SYWIXHZXHQDFOO-UHFFFAOYSA-N methyl n-phenyliminocarbamate Chemical compound COC(=O)N=NC1=CC=CC=C1 SYWIXHZXHQDFOO-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- HOSVESHQDSFAST-UHFFFAOYSA-N 2-[2-(2-cyanopropan-2-yl)hydrazinyl]-2-methylpropanenitrile Chemical compound N#CC(C)(C)NNC(C)(C)C#N HOSVESHQDSFAST-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- 238000007711 solidification Methods 0.000 description 4
- 230000008023 solidification Effects 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 238000003482 Pinner synthesis reaction Methods 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000010952 in-situ formation Methods 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical group O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- YXGWBKCOOBHTPT-UHFFFAOYSA-N benzene;chlorobenzene Chemical compound C1=CC=CC=C1.ClC1=CC=CC=C1 YXGWBKCOOBHTPT-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- ZVQXQPNJHRNGID-UHFFFAOYSA-N tetramethylsuccinonitrile Chemical compound N#CC(C)(C)C(C)(C)C#N ZVQXQPNJHRNGID-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/12—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
- C07C245/04—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/04—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines without replacement of the other oxygen atom of the carboxyl group, e.g. imino-ethers
- C07C257/06—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines without replacement of the other oxygen atom of the carboxyl group, e.g. imino-ethers having carbon atoms of imino-carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms, or to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/14—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerization Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR99/00391 | 1999-01-15 | ||
| FR9900391A FR2788517B1 (fr) | 1999-01-15 | 1999-01-15 | Procede de preparation d'azoiminoethers et d'esters d'acides azocarboxyliques, et nouveaux esters mixtes d'acides azocarboxyliques |
| PCT/FR2000/000022 WO2000042000A1 (fr) | 1999-01-15 | 2000-01-07 | Procede de preparation d'azoiminoethers et d'esters d'acides azocarboxyliques, et nouveaux esters mixtes d'acides azocarboxyliques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2359459A1 true CA2359459A1 (en) | 2000-07-20 |
Family
ID=9540891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002359459A Abandoned CA2359459A1 (en) | 1999-01-15 | 2000-01-07 | Method for the preparation of azoiminoethers and of azocarboxylic acid esters, and novel mixed esters of azocarboxylic acids |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6407219B1 (enExample) |
| EP (1) | EP1147077B1 (enExample) |
| JP (1) | JP2002534495A (enExample) |
| KR (1) | KR100776703B1 (enExample) |
| CN (1) | CN1211356C (enExample) |
| AT (1) | ATE402139T1 (enExample) |
| AU (1) | AU3051200A (enExample) |
| CA (1) | CA2359459A1 (enExample) |
| DE (1) | DE60039582D1 (enExample) |
| FR (1) | FR2788517B1 (enExample) |
| IL (1) | IL144099A0 (enExample) |
| PL (1) | PL348863A1 (enExample) |
| RU (1) | RU2245872C2 (enExample) |
| WO (1) | WO2000042000A1 (enExample) |
| ZA (1) | ZA200105221B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2813319A1 (fr) * | 2000-08-29 | 2002-03-01 | Atofina | Procede de fabrication de fibres a base d'acrylonitrile |
| FR2870240B1 (fr) * | 2004-05-13 | 2006-07-07 | Arkema Sa | Procede de preparation d'une alcoxyamine ou de ses sels comprenant une etape de photolyse |
| CN103193686B (zh) * | 2013-04-26 | 2014-10-29 | 山东师范大学 | 酯化法制备偶氮二甲酸二烷基酯 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS582230B2 (ja) | 1974-01-29 | 1983-01-14 | 和光純薬工業 （株） | アゾグアニル化合物の製法 |
| GB2111979A (en) * | 1981-11-19 | 1983-07-13 | Ici Plc | Azoimindether hydrochloride production |
| DE3471664D1 (en) * | 1983-11-10 | 1988-07-07 | Nitto Boseki Co Ltd | Process for producing polymers of monoallylamine |
| JPH0625100B2 (ja) * | 1986-01-14 | 1994-04-06 | 和光純薬工業株式会社 | アゾイミノエ−テルの製造法 |
| JP4092739B2 (ja) * | 1996-09-27 | 2008-05-28 | 和光純薬工業株式会社 | アゾエステル化合物の新規な製造方法 |
-
1999
- 1999-01-15 FR FR9900391A patent/FR2788517B1/fr not_active Expired - Lifetime
-
2000
- 2000-01-07 JP JP2000593568A patent/JP2002534495A/ja active Pending
- 2000-01-07 AU AU30512/00A patent/AU3051200A/en not_active Abandoned
- 2000-01-07 CN CNB008027595A patent/CN1211356C/zh not_active Expired - Lifetime
- 2000-01-07 CA CA002359459A patent/CA2359459A1/en not_active Abandoned
- 2000-01-07 WO PCT/FR2000/000022 patent/WO2000042000A1/fr not_active Ceased
- 2000-01-07 US US09/889,147 patent/US6407219B1/en not_active Expired - Lifetime
- 2000-01-07 PL PL00348863A patent/PL348863A1/xx not_active Application Discontinuation
- 2000-01-07 KR KR1020017008907A patent/KR100776703B1/ko not_active Expired - Fee Related
- 2000-01-07 RU RU2001122813/04A patent/RU2245872C2/ru not_active IP Right Cessation
- 2000-01-07 AT AT00900534T patent/ATE402139T1/de not_active IP Right Cessation
- 2000-01-07 IL IL14409900A patent/IL144099A0/xx unknown
- 2000-01-07 DE DE60039582T patent/DE60039582D1/de not_active Expired - Fee Related
- 2000-01-07 EP EP00900534A patent/EP1147077B1/fr not_active Expired - Lifetime
-
2001
- 2001-06-25 ZA ZA200105221A patent/ZA200105221B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL348863A1 (en) | 2002-06-17 |
| JP2002534495A (ja) | 2002-10-15 |
| RU2245872C2 (ru) | 2005-02-10 |
| KR100776703B1 (ko) | 2007-11-16 |
| DE60039582D1 (de) | 2008-09-04 |
| ATE402139T1 (de) | 2008-08-15 |
| CN1336913A (zh) | 2002-02-20 |
| FR2788517A1 (fr) | 2000-07-21 |
| WO2000042000A1 (fr) | 2000-07-20 |
| EP1147077A1 (fr) | 2001-10-24 |
| EP1147077B1 (fr) | 2008-07-23 |
| ZA200105221B (en) | 2002-10-10 |
| US6407219B1 (en) | 2002-06-18 |
| CN1211356C (zh) | 2005-07-20 |
| IL144099A0 (en) | 2002-05-23 |
| FR2788517B1 (fr) | 2001-03-16 |
| KR20010101530A (ko) | 2001-11-14 |
| AU3051200A (en) | 2000-08-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |