DD145911A5 - Verfahren zur gleichzeitigen herst llung von monomeren 4,4'-methylendiarylamin und methyle bruecken aufweisenden polyarylaminen - Google Patents

Verfahren zur gleichzeitigen herst llung von monomeren 4,4'-methylendiarylamin und methyle bruecken aufweisenden polyarylaminen Download PDF

Info

Publication number: DD145911A5
Authority: DD; German Democratic Republic
Prior art keywords: mda; acid; mixture; acids; crystallization
Prior art date: 1978-09-12

Application number

DD79215412A

Other languages

German (de)

English (en)

Inventor

Efim Biller

Original Assignee

Sulzer Ag

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.)

1978-09-12

Filing date

1979-09-07

Publication date

1981-01-14

1979-09-07 Application filed by Sulzer Ag filed Critical Sulzer Ag

1981-01-14 Publication of DD145911A5 publication Critical patent/DD145911A5/de

Links

238000000034 method Methods 0.000 title claims description 20
239000000178 monomer Substances 0.000 title description 6
238000002360 preparation method Methods 0.000 title description 4
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 title 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 45
239000000203 mixture Substances 0.000 claims abstract description 36
150000003839 salts Chemical class 0.000 claims abstract description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
238000002425 crystallisation Methods 0.000 claims abstract description 17
230000008025 crystallization Effects 0.000 claims abstract description 17
239000007864 aqueous solution Substances 0.000 claims abstract description 9
239000007859 condensation product Substances 0.000 claims abstract description 9
150000004982 aromatic amines Chemical class 0.000 claims abstract description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 48
239000013078 crystal Substances 0.000 claims description 24
239000002253 acid Substances 0.000 claims description 23
239000000243 solution Substances 0.000 claims description 17
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 14
229920000768 polyamine Polymers 0.000 claims description 14
150000007513 acids Chemical class 0.000 claims description 10
230000005588 protonation Effects 0.000 claims description 9
ABDBNWQRPYOPDF-UHFFFAOYSA-N carbonofluoridic acid Chemical class OC(F)=O ABDBNWQRPYOPDF-UHFFFAOYSA-N 0.000 claims description 7
229940098779 methanesulfonic acid Drugs 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 5
238000000605 extraction Methods 0.000 claims description 4
230000002209 hydrophobic effect Effects 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 3
-1 arylamine salt Chemical class 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 3
150000003460 sulfonic acids Chemical class 0.000 claims description 3
125000005266 diarylamine group Chemical group 0.000 claims description 2
238000011084 recovery Methods 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 43
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 abstract description 15
238000009833 condensation Methods 0.000 abstract description 11
230000005494 condensation Effects 0.000 abstract description 11
239000003377 acid catalyst Substances 0.000 abstract description 4
239000000047 product Substances 0.000 description 11
239000012452 mother liquor Substances 0.000 description 6
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
150000001448 anilines Chemical class 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000010626 work up procedure Methods 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000002156 mixing Methods 0.000 description 3
229920001228 polyisocyanate Polymers 0.000 description 3
239000005056 polyisocyanate Substances 0.000 description 3
239000004814 polyurethane Substances 0.000 description 3
229920002635 polyurethane Polymers 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000012266 salt solution Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000006260 foam Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
102100040141 Aminopeptidase O Human genes 0.000 description 1
108050008333 Aminopeptidase O Proteins 0.000 description 1
239000004970 Chain extender Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
VNNRSPGTAMTISX-UHFFFAOYSA-N chromium nickel Chemical compound [Cr].[Ni] VNNRSPGTAMTISX-UHFFFAOYSA-N 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
DTIYPFOXKXUYLD-UHFFFAOYSA-N cyclohexa-2,4-dien-1-amine Chemical compound NC1CC=CC=C1 DTIYPFOXKXUYLD-UHFFFAOYSA-N 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000010586 diagram Methods 0.000 description 1
KIQKWYUGPPFMBV-UHFFFAOYSA-N diisocyanatomethane Chemical compound O=C=NCN=C=O KIQKWYUGPPFMBV-UHFFFAOYSA-N 0.000 description 1
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
238000009776 industrial production Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
239000002991 molded plastic Substances 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
238000013021 overheating Methods 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920006389 polyphenyl polymer Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000004064 recycling Methods 0.000 description 1
238000005201 scrubbing Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/78—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton from carbonyl compounds, e.g. from formaldehyde, and amines having amino groups bound to carbon atoms of six-membered aromatic rings, with formation of methylene-diarylamines
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/06—Amines
- C08G12/08—Amines aromatic
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L59/00—Compositions of polyacetals; Compositions of derivatives of polyacetals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Phenolic Resins Or Amino Resins (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

DD79215412A 1978-09-12 1979-09-07 Verfahren zur gleichzeitigen herst llung von monomeren 4,4'-methylendiarylamin und methyle bruecken aufweisenden polyarylaminen DD145911A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH953778		1978-09-12

Publications (1)

Publication Number	Publication Date
DD145911A5 true DD145911A5 (de)	1981-01-14

Family

ID=4353041

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79215412A DD145911A5 (de)	1978-09-12	1979-09-07	Verfahren zur gleichzeitigen herst llung von monomeren 4,4'-methylendiarylamin und methyle bruecken aufweisenden polyarylaminen

Country Status (8)

Country	Link
US (1)	US4297511A (pt)
EP (1)	EP0009094B1 (pt)
JP (1)	JPS5555144A (pt)
AT (1)	ATE848T1 (pt)
BR (1)	BR7905790A (pt)
DD (1)	DD145911A5 (pt)
DE (1)	DE2962512D1 (pt)
PT (1)	PT70004A (pt)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3142529A1 (de) *	1981-10-27	1983-05-05	Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München	Verfahren zur herstellung von diaminen der diphenylmethanreihe
DE19513269A1 (de) *	1995-04-07	1996-10-10	Bayer Ag	Fraktionierung und Reinigung von aromatischen Polyamingemischen und deren Verwendung

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2938054A (en) *	1958-02-18	1960-05-24	Allied Chem	Process for purification of 4, 4'-methylenedianiline
FR1549769A (pt) *	1966-12-20	1968-12-13
US3954867A (en) *	1969-10-20	1976-05-04	Funk Jr Bernard D	Continuous process for preparing methylene dianilines
DE2127263A1 (de) *	1971-06-02	1973-01-04	Bayer Ag	Verfahren zur herstellung von aromatischen polyaminen
US4025557A (en) *	1972-06-03	1977-05-24	Bayer Aktiengesellschaft	Process for the production of polyamines
CA1004234A (en) *	1972-08-04	1977-01-25	Bayer Aktiengesellschaft	Process for the production of polyamines
DE2500573A1 (de) *	1975-01-09	1976-07-15	Bayer Ag	Verfahren zur herstellung von polyaminen
DE2528694C2 (de) *	1975-06-27	1982-04-22	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung von mehrkernigen aromatischen Polyaminen
DE2648982C2 (de) *	1975-11-11	1985-07-11	Efim Zürich Biller	Verfahren zur Herstellung von Methylenbrücken aufweisenden Polyarylaminen
US4201722A (en) *	1976-06-04	1980-05-06	The Upjohn Company	Process for separating 4,4'-diaminodiphenylmethane
DE2748968A1 (de) *	1976-11-06	1978-05-11	Elprochine Ag	Verfahren zur herstellung von methylenbruecken aufweisenden polyarylaminen
US4130588A (en) *	1977-02-02	1978-12-19	The Dow Chemical Company	Process for producing methylene dianiline

1979
- 1979-07-21 DE DE7979102584T patent/DE2962512D1/de not_active Expired
- 1979-07-21 AT AT79102584T patent/ATE848T1/de not_active IP Right Cessation
- 1979-07-21 EP EP79102584A patent/EP0009094B1/de not_active Expired
- 1979-07-31 PT PT70004A patent/PT70004A/pt unknown
- 1979-09-04 US US06/072,313 patent/US4297511A/en not_active Expired - Lifetime
- 1979-09-07 DD DD79215412A patent/DD145911A5/de unknown
- 1979-09-11 JP JP11663179A patent/JPS5555144A/ja active Pending
- 1979-09-11 BR BR7905790A patent/BR7905790A/pt unknown

Also Published As

Publication number	Publication date
ATE848T1 (de)	1982-04-15
EP0009094B1 (de)	1982-04-14
EP0009094A2 (de)	1980-04-02
PT70004A (de)	1979-08-01
DE2962512D1 (en)	1982-05-27
BR7905790A (pt)	1980-07-15
EP0009094A3 (en)	1980-04-16
US4297511A (en)	1981-10-27
JPS5555144A (en)	1980-04-22

Publication	Publication Date	Title
EP1616890B1 (de)	2016-11-30	Verfahren zur Herstellung von Polyaminen der Diphenylmethanreihe bei niedriger Protonierung
DE1937685C2 (de)	1982-07-01	Verfahren zur Herstellung von an o,p'- und o,o'-Isomeren reichen Di(aminophenyl)methan
DE2623681A1 (de)	1977-01-20	Verfahren zur herstellung eines gemisches aus di(aminophenyl)methan und oligomeren polymethylenpolyphenylpolyaminen
DE1242623B (de)	1967-06-22	Verfahren zur Herstellung von primaeren Polyaminen
DE2631034A1 (de)	1977-02-10	Verfahren zur herstellung eines gemisches aus di(aminophenyl)methan und oligomeren polymethylenpolyphenylpolyaminen
EP0567881A2 (de)	1993-11-03	Verfahren zur Herstellung von Gemischen von Polyaminen der Polyamino-polyaryl-polymethylenreihe
EP0597361A1 (de)	1994-05-18	Verfahren zur Herstellung von Dinitrotoluol
DE2426116B2 (de)	1978-05-11	Verfahren zur Herstellung von Methylenbrücken aufweisenden PoIyarylaminen
DE69213678T2 (de)	1997-01-23	Verfahren zur Herstellung von Polyaminen für helleren auf Polyisocyanat basierenden Schaum
DE2500573A1 (de)	1976-07-15	Verfahren zur herstellung von polyaminen
DE2238920C3 (de)	1984-09-27	Verfahren zur Herstellung von Polyaminen
DE2500574A1 (de)	1976-07-15	Verfahren zur herstellung von polyaminen
DD295628A5 (de)	1991-11-07	Verfahren zur diskontinuierlichen herstellung von methylendianilin/polyamingemischen
DE2750975A1 (de)	1978-05-24	Verfahren zur herstellung von polyaminen der diphenylmethan-reihe
DE2557500C2 (pt)	1988-07-21
DD145911A5 (de)	1981-01-14	Verfahren zur gleichzeitigen herst llung von monomeren 4,4'-methylendiarylamin und methyle bruecken aufweisenden polyarylaminen
DE2343658C2 (de)	1982-06-03	Verfahren zur Herstellung von Polyaminen
DE1793137A1 (de)	1972-03-09	Verfahren zur Herstellung von Di(aminophenyl)methan
DE2517301A1 (de)	1975-11-06	Verfahren zur herstellung von aromatischen polyaminen
EP0109931A2 (de)	1984-05-30	Verfahren zur Herstellung von Methylenbrücken aufweisenden Polyarylaminen
EP0736520B1 (de)	1999-01-20	Fraktionierung und Reinigung von aromatischen Polyamingemischen und deren Verwendung
DD238042A1 (de)	1986-08-06	Verfahren zur kontinuierlichen herstellung von mda/polyamingemischen
EP0078414B1 (de)	1984-12-19	Verfahren zur Herstellung von Diaminen der Diphenylmethanreihe
DE2648982C2 (de)	1985-07-11	Verfahren zur Herstellung von Methylenbrücken aufweisenden Polyarylaminen
DE2719996C2 (de)	1986-06-26	Verfahren zum Abtrennen von 4,4'-Diaminodiphenylmethan in praktisch reiner Form aus Mischungen desselben mit dem entsprechenden 2,4'-Isomeren