DD212524A5 - Verfahren zur herstellung von methylenbruecken aufweisenden polyarylaminen - Google Patents

Verfahren zur herstellung von methylenbruecken aufweisenden polyarylaminen Download PDF

Info

Publication number: DD212524A5
Authority: DD; German Democratic Republic
Prior art keywords: condensate; formaldehyde; aniline; precondensate; acid
Prior art date: 1982-10-25

Application number

DD25591383A

Other languages

German (de)

English (en)

Inventor

Efim Biller

Original Assignee

Elprochine 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.)

1982-10-25

Filing date

1983-10-24

Publication date

1984-08-15

1983-10-24 Application filed by Elprochine Ag filed Critical Elprochine Ag

1984-08-15 Publication of DD212524A5 publication Critical patent/DD212524A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 18
125000001570 methylene group Chemical class [H]C([H])([*:1])[*:2] 0.000 title description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 171
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 102
238000006243 chemical reaction Methods 0.000 claims abstract description 46
238000000034 method Methods 0.000 claims abstract description 27
239000003377 acid catalyst Substances 0.000 claims abstract description 22
229920000768 polyamine Polymers 0.000 claims abstract description 20
239000000203 mixture Substances 0.000 claims abstract description 16
-1 polymethylene Polymers 0.000 claims abstract description 13
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims abstract description 11
238000002360 preparation method Methods 0.000 claims abstract description 9
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims abstract description 8
229920000265 Polyparaphenylene Polymers 0.000 claims abstract description 7
239000002253 acid Substances 0.000 claims description 40
230000002378 acidificating effect Effects 0.000 claims description 34
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 25
150000007513 acids Chemical class 0.000 claims description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
238000009833 condensation Methods 0.000 claims description 6
230000005494 condensation Effects 0.000 claims description 6
239000012266 salt solution Substances 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 4
230000008707 rearrangement Effects 0.000 claims description 3
239000011949 solid catalyst Substances 0.000 claims description 3
241000208150 Geraniaceae Species 0.000 claims 1
NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical compound NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 claims 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
239000012948 isocyanate Substances 0.000 abstract description 4
150000002513 isocyanates Chemical class 0.000 abstract description 4
230000003197 catalytic effect Effects 0.000 abstract description 3
238000012546 transfer Methods 0.000 abstract description 3
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
239000000047 product Substances 0.000 description 25
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
239000003054 catalyst Substances 0.000 description 13
239000000243 solution Substances 0.000 description 11
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
238000003756 stirring Methods 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
238000002156 mixing Methods 0.000 description 5
238000006386 neutralization reaction Methods 0.000 description 5
MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
150000004985 diamines Chemical class 0.000 description 4
229940098779 methanesulfonic acid Drugs 0.000 description 4
239000007787 solid Substances 0.000 description 4
230000005526 G1 to G0 transition Effects 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
238000009826 distribution Methods 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000012071 phase Substances 0.000 description 3
238000000926 separation method Methods 0.000 description 3
SQMOOVFBFVTTGF-UHFFFAOYSA-N 1-benzyl-1-phenylhydrazine Chemical compound C=1C=CC=CC=1N(N)CC1=CC=CC=C1 SQMOOVFBFVTTGF-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
QKZIVVMOMKTVIK-UHFFFAOYSA-N anilinomethanesulfonic acid Chemical compound OS(=O)(=O)CNC1=CC=CC=C1 QKZIVVMOMKTVIK-UHFFFAOYSA-N 0.000 description 2
238000013459 approach Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000001413 cellular effect Effects 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
229920001228 polyisocyanate Polymers 0.000 description 2
239000005056 polyisocyanate Substances 0.000 description 2
238000012545 processing Methods 0.000 description 2
230000005588 protonation Effects 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
ZEMCGIDMAMIJLF-UHFFFAOYSA-N 1-benzyl-2-phenylhydrazine Chemical class C=1C=CC=CC=1CNNC1=CC=CC=C1 ZEMCGIDMAMIJLF-UHFFFAOYSA-N 0.000 description 1
WLXGQMVCYPUOLM-UHFFFAOYSA-N 1-hydroxyethanesulfonic acid Chemical compound CC(O)S(O)(=O)=O WLXGQMVCYPUOLM-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000004653 carbonic acids Chemical class 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000002131 composite material Substances 0.000 description 1
238000010908 decantation Methods 0.000 description 1
230000008021 deposition Effects 0.000 description 1
238000013461 design Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000009434 installation Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
OHQOKJPHNPUMLN-UHFFFAOYSA-N n,n'-diphenylmethanediamine Chemical compound C=1C=CC=CC=1NCNC1=CC=CC=C1 OHQOKJPHNPUMLN-UHFFFAOYSA-N 0.000 description 1
238000013021 overheating Methods 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000002904 solvent Substances 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Phenolic Resins Or Amino Resins (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD25591383A 1982-10-25 1983-10-24 Verfahren zur herstellung von methylenbruecken aufweisenden polyarylaminen DD212524A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH618882		1982-10-25
CH136883		1983-03-14

Publications (1)

Publication Number	Publication Date
DD212524A5 true DD212524A5 (de)	1984-08-15

Family

ID=25687464

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD25591383A DD212524A5 (de)	1982-10-25	1983-10-24	Verfahren zur herstellung von methylenbruecken aufweisenden polyarylaminen

Country Status (4)

Country	Link
EP (1)	EP0109931A3 (fr)
BR (1)	BR8305870A (fr)
DD (1)	DD212524A5 (fr)
PT (1)	PT77551B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4792624A (en) *	1987-02-26	1988-12-20	The Dow Chemical Company	Process for polymeric MDA, recycle of finished polymeric MDA
JP2825604B2 (ja) *	1990-04-11	1998-11-18	三井化学株式会社	メチレン架橋されたポリアリールアミンの製造方法
CZ296966B6 (cs)	1997-02-24	2006-08-16	Boehringer Ingelheim Pharma Gmbh & Co. Kg.	Farmaceutický prostredek
DE10111337A1 (de) *	2001-03-08	2002-09-12	Basf Ag	Verfahren zur Herstellung von MDI, insbesondere von 2.4'-MDI
DE10331772A1 (de) *	2003-07-11	2005-02-03	Basf Ag	Verfahren zur Herstellung von Diaminodiarylmethanen
WO2025073928A1 (fr)	2023-10-06	2025-04-10	Basf Se	Procédé de préparation de mda

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3676497A (en) *	1968-08-06	1972-07-11	Upjohn Co	Process for preparing di(aminophenyl)-methanes
GB1287141A (en) *	1969-01-01	1972-08-31	Ici Ltd	Manufacture of methylene-bridged polyarylamines
DE2127263A1 (de) *	1971-06-02	1973-01-04	Bayer Ag	Verfahren zur herstellung von aromatischen polyaminen
DE2426116B2 (de) *	1973-06-01	1978-05-11	Efim Freiburg Biller (Schweiz)	Verfahren zur Herstellung von Methylenbrücken aufweisenden PoIyarylaminen
DE2750975A1 (de) *	1976-11-19	1978-05-24	Mobay Chemical Corp	Verfahren zur herstellung von polyaminen der diphenylmethan-reihe

1983
- 1983-10-24 EP EP83810491A patent/EP0109931A3/fr not_active Withdrawn
- 1983-10-24 DD DD25591383A patent/DD212524A5/de unknown
- 1983-10-24 PT PT7755183A patent/PT77551B/pt unknown
- 1983-10-24 BR BR8305870A patent/BR8305870A/pt unknown

Also Published As

Publication number	Publication date
BR8305870A (pt)	1984-05-29
EP0109931A3 (fr)	1984-10-03
PT77551A (de)	1983-11-01
PT77551B (de)	1986-02-12
EP0109931A2 (fr)	1984-05-30

Publication	Publication Date	Title
EP1616890B1 (fr)	2016-11-30	Procédé de préparation de polyamines de la série du diphénylméthane par faible protonation
DE2631034A1 (de)	1977-02-10	Verfahren zur herstellung eines gemisches aus di(aminophenyl)methan und oligomeren polymethylenpolyphenylpolyaminen
EP0014927B1 (fr)	1981-09-16	Procédé pour la préparation de mélanges de polyamines de la série des polyamino-polyaryl-polyméthylènes
EP0288892B1 (fr)	1992-06-03	Procédé pour la préparation de polyamines aromatiques contenant plusieurs noyaux
DE3044389C2 (fr)	1987-11-19
DE2426116B2 (de)	1978-05-11	Verfahren zur Herstellung von Methylenbrücken aufweisenden PoIyarylaminen
EP0003303B1 (fr)	1980-09-17	Procédé pour la préparation de polyamines de la série du diphénylméthane, riches en isomères ortho
DE2947531A1 (de)	1981-06-04	Verfahren zur herstellung von polyphenylpolymethylenpolyaminen
DE2238920C3 (de)	1984-09-27	Verfahren zur Herstellung von Polyaminen
DE69213678T2 (de)	1997-01-23	Verfahren zur Herstellung von Polyaminen für helleren auf Polyisocyanat basierenden Schaum
DD212524A5 (de)	1984-08-15	Verfahren zur herstellung von methylenbruecken aufweisenden polyarylaminen
DE2750975A1 (de)	1978-05-24	Verfahren zur herstellung von polyaminen der diphenylmethan-reihe
DE2500574C3 (de)	1980-05-22	Verfahren zur Herstellung von Polyaminen
DE2500573A1 (de)	1976-07-15	Verfahren zur herstellung von polyaminen
EP1167343B1 (fr)	2003-05-21	Procédé pour la production d'un mélange de polyamines aromatiques
DE2343658C2 (de)	1982-06-03	Verfahren zur Herstellung von Polyaminen
DE2557500A1 (de)	1977-06-30	Verfahren zur herstellung von polyaminen
DE2227110C3 (de)	1984-08-23	Verfahren zur Herstellung von Polyaminen
DE2238379A1 (de)	1974-02-14	Verfahren zur herstellung von polyaminen
DE2648982C2 (de)	1985-07-11	Verfahren zur Herstellung von Methylenbrücken aufweisenden Polyarylaminen
DE2557501C2 (fr)	1988-07-21
DE1793137A1 (de)	1972-03-09	Verfahren zur Herstellung von Di(aminophenyl)methan
EP0078414B1 (fr)	1984-12-19	Procédé pour la préparation de diamines de la série de diphényl méthane
EP0009094B1 (fr)	1982-04-14	Procédé pour la préparation de polyarylamines à ponts méthylène
DE2307864A1 (de)	1974-08-22	Verfahren zur herstellung von diaminodiarylmethanen