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WO1992012120A1 - Bis(aminophenoxy)naphtalenes et bis(nitrophenoxy)naphtalenes - Google Patents

Bis(aminophenoxy)naphtalenes et bis(nitrophenoxy)naphtalenes Download PDF

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Publication number
WO1992012120A1
WO1992012120A1 PCT/US1992/000001 US9200001W WO9212120A1 WO 1992012120 A1 WO1992012120 A1 WO 1992012120A1 US 9200001 W US9200001 W US 9200001W WO 9212120 A1 WO9212120 A1 WO 9212120A1
Authority
WO
WIPO (PCT)
Prior art keywords
bis
aminophenoxy
naphthalenes
nitrophenoxy
naphthalene
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.)
Ceased
Application number
PCT/US1992/000001
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English (en)
Inventor
Carl Andrew Renner
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of WO1992012120A1 publication Critical patent/WO1992012120A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/90—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. amino-diphenylethers

Definitions

  • the present invention relates to bis(amino- phenoxy)naphthalenes which are derived from bis(nitro- phenoxy)naphthalenes and the preparation of bis(nitro- phenoxy)naphthalenes from dihydroxynaphthalenes with halonitrobenzenes.
  • the bis(aminophenoxy)naphthalenes are made by the reduction of the corresponding bis(nitrophenoxy)naphthalenes.
  • JP 63/126848, 30 May 1988 discloses 4,4'-bis(3-nitrophenoxy)-3,3',5,5'-tetramethylbipheny1 and reducing it.
  • U.S. 4,713,438 discloses alpha, alpha'-bis- (p-aminophenyl)-4,4 -bis(isopropyl)biphenyl.
  • JP 62/248635, 29 Oct. 1987 discloses 4,4'-bis(3-aminophenoxy)biphenyl and its use as a monomer in preparing polyimides.
  • U.S. 4,377,525 discloses l,3-bis(3-amino- phenoxy)benzene for use as a monomer in preparing polyimides.
  • U.S. 4,064,107 discloses p,p'-bis(4-amino ⁇ phenoxy)diphenyl ether.
  • 1,6-bis( -aminophenoxy)naphthalene 1,6-bis(4-nitro- phenoxy) aphthalene, 2,7-bis(4-nitrophenoxy)naphtha ⁇ lene, 2,7-bis(4-aminophenoxy)naphthalene, and their preparation.
  • the preparation involves reacting 1,6-dihydroxyna ⁇ hthalene or 2,7-dihydroxynaphthalene with para-nitrochlorobenzene in a polar organic solvent, such as dimethylacetamide, and a base, such as potassium carbonate.
  • a polar organic solvent such as dimethylacetamide
  • a base such as potassium carbonate.
  • the product diamino compounds are useful as monomers in the preparation of polyamides and polyimides.
  • the bis(nitrophenoxy)naphthalenes of the present invention are made by reaction of dihydroxynaphthalenes with a halonitrobenzene in a polar organic solvent in the presence of a base.
  • Suitable polar organic solvents include N,N-dimethylacetamide, N,N-dimethylformamide, -3- m-cresol, dimethyl sulfoxide and N-methylpyrrolidone. Of these, N-N-dimethylacetamide is the preferred solvent.
  • Suitable bases include the hydroxides, carbonates, bicarbonates, hydrides and lower alkoxides, of the alkali metals, particularly potassium, sodium and lithium.
  • potassium carbonate is the preferred base.
  • the reaction medium will contain from 2 to 19 weight percent and preferably 10 to 15 weight percent dihydroxynaphthalene.
  • the mole ratio of dihydroxynaphthalene to halonitrobenzene present is about 0.9:2 to about 1.1:2 and preferably about 1:2.
  • the amount of base present (calculated as K2CO 3 ) is preferably from 86 to 250 weight percent and preferably 86 to 130 weight percent, as based on dihydroxynaphthalene present.
  • the temperature is from 110* to 165*C with from 135* to 155*C being the preferred range.
  • the pressure is not critical and may be varied from 0.8 to 40 atmosphere. Atmospheric pressure is preferred for economic reasons.
  • the product can be separated from the solvent and base by filtration.
  • the solvent can be removed by distillation and the basic catalyst by extraction with a solvent which doesn't dissolve the product bis(4-nitrophenoxyphenyl)naphthalene.
  • the bis(4-nitrophenoxyphenyl)naphthalene is reduced to bis(4-aminophenoxy)naphthalene using hydrogen and a solid hydrogenation catalyst.
  • Suitable hydrogenation catalysts include palladium, platinum, nickel and rhodium.
  • the hydrogenation catalyst is a solid so that it can be readily separated from the product -4- bis(4-aminophenoxy)naphthalene by filtration.
  • the bis(4-nitrophenoxy)naphthalene can be melted and fed over a fixed bed of the hydrogenation catalyst along with hydrogen gas.
  • the hydrogenation reaction is carried out at 50* to 150 ⁇ C with 80* to 120"C being the preferred range.
  • the hydrogen pressure in the reactor generally will be from 1 to 600 psig (6.9 to 4200 kPag) with 50 to 400 psig (345 to 2758 kPag) being the preferred range.
  • the hydrogenation reaction can be carried out in a solvent such as 1-butanol, 2-butanol, N,N-dimethyl acetamide, 2-methoxyethanol, tetrahydrofuran, N,N-dimethylformamide or N-methylpyrrolidone.
  • the product bis(4-aminophenoxy)naphthalene can be reacted with dicarboxylic acids or dianhydrides of tetracarboxylic acids to make polyamides or polyimides which are useful in preparing gas separation membranes.
  • the resulting gas separation membranes are useful in separating a variety of gases but the most interesting one from a commercial viewpoint is separating nitrogen and oxygen from mixtures thereof such as air to produce nitrogen and oxygen of sufficient purity to be useful industrially.
  • nitrogen and oxygen of industrial grades it generally is necessary to use the membranes serially arranged to provide a plurality of separation stages.
  • the aromatic polyimides produced by reaction of 1,6-bis(4-aminophenoxy)naphthalene or 2,7-bis(4-aminophenoxy)naphthalene and bridged aromatic dianhydrides of the formula
  • the pressure was raised to 400 psig (2758 kPag) and held for thirty minutes.
  • the contents of the autoclave were poured under nitrogen to a 2-liter, three necked flask equipped with a mechanical stirrer, thermometer with a Thermowatch, which flask contained 600 ml of 1-butanol and 4 ml of 85% hydrazine hydrate in water at 80*C.
  • the autoclave was rinsed out with 100 ml of additional 1-butanol which was added to the 2-liter flask.
  • the mixture in the 2-liter flask was brought to a slow reflux.
  • the contents of the 2-liter flask was vacuum transferred to a 2-liter round bottom flask through a fritted glass filter covered with Celite* filtering aid. After the transfer, the contents of the second flask were heated to 105°C giving a clear solution. The second flask was cooled to O'C (crystallization of product began at 80 ⁇ C) .
  • the product was isolated by filtering through a fritted glass filter funnel, washed twice with 600 ml of hot water and one with 600 ml of deionized water. After drying overnight in a vacuum oven at 100"C and 125 mm Hg absolute pressure, -7-
  • the pressure was raised to 400 psig (2758 kPag) and held for 30 minutes.
  • the reaction mixture along with a wash of 200 ml 1-butanol was poured into a 2-liter, four necked flask equipped with a mechanical stirrer, heating mantle, thermometer with a Thermowatch, a condenser and a nitrogen supply, which flask contained 500 ml of 1-butanol and 2 ml of 85% hydrogen hydrate in water at 120"C.
  • the mixture was heated to reflux.
  • the mixture was vacuum transferred to a second similarly equipped flask through a steam jacketed enclosed fritted glass funnel which had a bed of Celite ® filtering aid.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Cette invention concerne des bis(aminophénoxy)naphtalènes, leur préparation par réduction catalytique de bis(nitrophénoxy)naphtalènes avec de l'hydrogène et la préparation de bis(nitrophénoxy)naphtalènes à partir de dihydroxynaphtalènes et de chloronitrobenzène dans un solvant organique polaire tel que du diméthylacétamide en utilisant un catalyseur basique tel que du carbonate de potassium. Les composés de produit préférés sont le 1,6-bis(4-aminophénoxy)naphtalène, le 2,7-bis(4-aminophénoxy)naphtalène, le 1,6-bis(4-nitrophénoxy)naphtalène et le 2,7-bis(4-nitrophénoxy)naphtalène.
PCT/US1992/000001 1991-01-10 1992-01-02 Bis(aminophenoxy)naphtalenes et bis(nitrophenoxy)naphtalenes Ceased WO1992012120A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US63978491A 1991-01-10 1991-01-10
US639,784 1991-01-10

Publications (1)

Publication Number Publication Date
WO1992012120A1 true WO1992012120A1 (fr) 1992-07-23

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Application Number Title Priority Date Filing Date
PCT/US1992/000001 Ceased WO1992012120A1 (fr) 1991-01-10 1992-01-02 Bis(aminophenoxy)naphtalenes et bis(nitrophenoxy)naphtalenes

Country Status (2)

Country Link
AU (1) AU1186092A (fr)
WO (1) WO1992012120A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0537589A3 (en) * 1991-10-16 1993-06-23 Basf Aktiengesellschaft Process for the preparation of dinitro- and diaminophenoxy compounds
US5340904A (en) * 1992-12-29 1994-08-23 National Science Council Bis(4-aminophenoxy)naphthalene and its polymers
CN104744268A (zh) * 2015-03-04 2015-07-01 湖南工业大学 具有高平面性的含萘结构功能二胺单体及其合成方法和应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2148279A (en) * 1983-10-18 1985-05-30 Mitsui Toatsu Chemicals Process for preparing 1,3-bis(3-aminophenoxy)benzene
EP0192480A1 (fr) * 1985-02-22 1986-08-27 MITSUI TOATSU CHEMICALS, Inc. Bis(amino-3 phénoxy)aromatiques et procédé pour leur préparation
EP0357558A1 (fr) * 1988-09-02 1990-03-07 Ciba-Geigy Ag Bisimides de l'acide allyl- ou méthallylbicyclo-[2.2.1]heptène-5 dicarboxylique-2,3
EP0387203A2 (fr) * 1989-03-10 1990-09-12 Ciba-Geigy Ag Polyamides et polyimides ayant des groupements terminaux non-réactives
GB2229180A (en) * 1989-01-14 1990-09-19 British Petroleum Co Plc Novel polyimides and diamines

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2148279A (en) * 1983-10-18 1985-05-30 Mitsui Toatsu Chemicals Process for preparing 1,3-bis(3-aminophenoxy)benzene
EP0192480A1 (fr) * 1985-02-22 1986-08-27 MITSUI TOATSU CHEMICALS, Inc. Bis(amino-3 phénoxy)aromatiques et procédé pour leur préparation
EP0357558A1 (fr) * 1988-09-02 1990-03-07 Ciba-Geigy Ag Bisimides de l'acide allyl- ou méthallylbicyclo-[2.2.1]heptène-5 dicarboxylique-2,3
GB2229180A (en) * 1989-01-14 1990-09-19 British Petroleum Co Plc Novel polyimides and diamines
EP0387203A2 (fr) * 1989-03-10 1990-09-12 Ciba-Geigy Ag Polyamides et polyimides ayant des groupements terminaux non-réactives

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0537589A3 (en) * 1991-10-16 1993-06-23 Basf Aktiengesellschaft Process for the preparation of dinitro- and diaminophenoxy compounds
US5340904A (en) * 1992-12-29 1994-08-23 National Science Council Bis(4-aminophenoxy)naphthalene and its polymers
CN104744268A (zh) * 2015-03-04 2015-07-01 湖南工业大学 具有高平面性的含萘结构功能二胺单体及其合成方法和应用

Also Published As

Publication number Publication date
AU1186092A (en) 1992-08-17

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