IL94030A - Oxidiphthalic anhydride derivatives and their preparation - Google Patents

Oxidiphthalic anhydride derivatives and their preparation

Info

Publication number: IL94030A
Authority: IL; Israel
Prior art keywords: anhydride; formula; process according; preparation; dihalo
Prior art date: 1989-05-15

Application number

IL9403090A

Other languages

English (en)

Hebrew (he)

Other versions

IL94030A0 (en

Original Assignee

Occidental Chem 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.)

1989-05-15

Filing date

1990-04-06

Publication date

1994-11-11

1990-04-06 Application filed by Occidental Chem Co filed Critical Occidental Chem Co

1991-01-31 Publication of IL94030A0 publication Critical patent/IL94030A0/xx

1994-11-11 Publication of IL94030A publication Critical patent/IL94030A/en

Links

238000002360 preparation method Methods 0.000 title claims description 24
BCJIMAHNJOIWKQ-UHFFFAOYSA-N 4-[(1,3-dioxo-2-benzofuran-4-yl)oxy]-2-benzofuran-1,3-dione Chemical class O=C1OC(=O)C2=C1C=CC=C2OC1=CC=CC2=C1C(=O)OC2=O BCJIMAHNJOIWKQ-UHFFFAOYSA-N 0.000 title claims description 9
150000008064 anhydrides Chemical class 0.000 claims description 74
238000000034 method Methods 0.000 claims description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
150000001339 alkali metal compounds Chemical class 0.000 claims description 11
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 10
239000011698 potassium fluoride Substances 0.000 claims description 9
229910052794 bromium Inorganic materials 0.000 claims description 8
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 8
-1 oxydiphthalic anhydride compound Chemical class 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 6
229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
235000003270 potassium fluoride Nutrition 0.000 claims description 4
BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000003880 polar aprotic solvent Substances 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims 2
239000003444 phase transfer catalyst Substances 0.000 claims 1
229920001721 polyimide Polymers 0.000 description 15
239000004642 Polyimide Substances 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
239000000376 reactant Substances 0.000 description 9
125000006159 dianhydride group Chemical class 0.000 description 8
239000002904 solvent Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
229920005575 poly(amic acid) Polymers 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000002253 acid Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 5
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
XJHCXCQVJFPJIK-UHFFFAOYSA-M cesium fluoride Substances [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
229940113088 dimethylacetamide Drugs 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
239000000178 monomer Substances 0.000 description 4
PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 3
150000004985 diamines Chemical class 0.000 description 3
230000009477 glass transition Effects 0.000 description 3
238000006068 polycondensation reaction Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
HOLXVIZWJDORKM-UHFFFAOYSA-N 4,5-difluoro-2-benzofuran-1,3-dione Chemical compound FC1=CC=C2C(=O)OC(=O)C2=C1F HOLXVIZWJDORKM-UHFFFAOYSA-N 0.000 description 2
ULSOWUBMELTORB-UHFFFAOYSA-N 5,6-dichloro-2-benzofuran-1,3-dione Chemical compound C1=C(Cl)C(Cl)=CC2=C1C(=O)OC2=O ULSOWUBMELTORB-UHFFFAOYSA-N 0.000 description 2
UATBWQQFLABWKR-UHFFFAOYSA-N 5,6-difluoro-2-benzofuran-1,3-dione Chemical compound C1=C(F)C(F)=CC2=C1C(=O)OC2=O UATBWQQFLABWKR-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
101100010166 Mus musculus Dok3 gene Proteins 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
NUVDFTCNJBNRQR-UHFFFAOYSA-N 4-bromo-5-sulfanylphthalic acid Chemical compound OC(=O)C1=CC(S)=C(Br)C=C1C(O)=O NUVDFTCNJBNRQR-UHFFFAOYSA-N 0.000 description 1
ROFZMKDROVBLNY-UHFFFAOYSA-N 4-nitro-2-benzofuran-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC2=C1C(=O)OC2=O ROFZMKDROVBLNY-UHFFFAOYSA-N 0.000 description 1
BONIIQYTWOPUQI-UHFFFAOYSA-N 4-nitroisoindole-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC2=C1C(=O)NC2=O BONIIQYTWOPUQI-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
238000005384 cross polarization magic-angle spinning Methods 0.000 description 1
RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001362 electron spin resonance spectrum Methods 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000003063 flame retardant Substances 0.000 description 1
238000013467 fragmentation Methods 0.000 description 1
238000006062 fragmentation reaction Methods 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
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000009413 insulation Methods 0.000 description 1
239000012035 limiting reagent Substances 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000004377 microelectronic Methods 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
150000004986 phenylenediamines Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000005361 soda-lime glass Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
RHCCVKFZDQPUOY-UHFFFAOYSA-N thianthrene-2,3,7,8-tetracarboxylic acid Chemical compound S1C2=CC(C(O)=O)=C(C(O)=O)C=C2SC2=C1C=C(C(=O)O)C(C(O)=O)=C2 RHCCVKFZDQPUOY-UHFFFAOYSA-N 0.000 description 1
YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
238000007740 vapor deposition Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Furan Compounds (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Polyesters Or Polycarbonates (AREA)
Epoxy Resins (AREA)

IL9403090A 1989-05-15 1990-04-06 Oxidiphthalic anhydride derivatives and their preparation IL94030A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/352,070 US4943642A (en)	1989-05-15	1989-05-15	Halo-oxydiphthalic anhydrides

Publications (2)

Publication Number	Publication Date
IL94030A0 IL94030A0 (en)	1991-01-31
IL94030A true IL94030A (en)	1994-11-11

Family

ID=23383672

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9403090A IL94030A (en)	1989-05-15	1990-04-06	Oxidiphthalic anhydride derivatives and their preparation

Country Status (7)

Country	Link
US (1)	US4943642A (fr)
EP (1)	EP0398206A1 (fr)
JP (1)	JPH02311472A (fr)
BR (1)	BR9002177A (fr)
CA (1)	CA2015164A1 (fr)
IL (1)	IL94030A (fr)
NO (1)	NO902094L (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5003031A (en) *	1989-05-15	1991-03-26	Occidental Chemical Corporation	Polyimides and co-polyimides based on dioxydiphthalic anhydride
EP0438382A1 (fr) *	1990-01-19	1991-07-24	Ciba-Geigy Ag	Dianhydrides aromatiques disubstitués et polyimides préparés à partir de ceux-ci
US20060293528A1 (en) *	2005-06-24	2006-12-28	General Electric Company	Method of purifying dianhydrides
CN103044371B (zh) *	2012-12-12	2015-05-06	巨化集团技术中心	一种4-氟代苯酐的制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5975056A (ja) *	1982-10-20	1984-04-27	テルモ株式会社	医療用具
US4697023A (en) *	1986-10-03	1987-09-29	Occidental Chemical Corporation	Process for the preparation of oxy-diphthalic anhydrides
US4837404A (en) *	1987-08-24	1989-06-06	Occidental Chemical Corporation	Process for the preparation of oxy-diphthalic anhydrides
US4808731A (en) *	1988-03-04	1989-02-28	General Electric Company	Method for making oxydiphthalic anhydride

1989
- 1989-05-15 US US07/352,070 patent/US4943642A/en not_active Expired - Lifetime
1990
- 1990-04-06 IL IL9403090A patent/IL94030A/en not_active IP Right Cessation
- 1990-04-23 CA CA002015164A patent/CA2015164A1/fr not_active Abandoned
- 1990-05-08 JP JP2118494A patent/JPH02311472A/ja active Pending
- 1990-05-10 BR BR909002177A patent/BR9002177A/pt not_active Application Discontinuation
- 1990-05-11 NO NO90902094A patent/NO902094L/no unknown
- 1990-05-14 EP EP90109010A patent/EP0398206A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
BR9002177A (pt)	1991-08-13
US4943642A (en)	1990-07-24
NO902094D0 (no)	1990-05-11
IL94030A0 (en)	1991-01-31
EP0398206A1 (fr)	1990-11-22
NO902094L (no)	1990-11-16
JPH02311472A (ja)	1990-12-27
CA2015164A1 (fr)	1990-11-15

Legal Events

Date	Code	Title	Description
1997-01-10	RH	Patent void

Publication	Publication Date	Title
US3956320A (en)	1976-05-11	Aromatic bis(ether phthalis anhydride) compounds
US4134895A (en)	1979-01-16	Imidyl-benzenedicarboxylic acid derivatives
US4017511A (en)	1977-04-12	Preparation of aromatic bisimides
JP3053462B2 (ja)	2000-06-19	９，９−ビス（パーフルオロアルキル）キサンテン、９−アリール−９−パーフルオロアルキルキサンテン、それより誘導されるモノマーおよびポリマー
US5003086A (en)	1991-03-26	Process of preparing dioxydiphthalic anhydride
US4054577A (en)	1977-10-18	Preparation of aromatic bisimides
US4933469A (en)	1990-06-12	Method for preparing oxybisphthalimides
US5185451A (en)	1993-02-09	Bis-imides of dioxydiphthalic acid
US4943642A (en)	1990-07-24	Halo-oxydiphthalic anhydrides
JPS5835512B2 (ja)	1983-08-03	アセチレン置換ポリイミドオリゴマ−の製造方法
US4002645A (en)	1977-01-11	Bis aromatic anhydrides
US5003031A (en)	1991-03-26	Polyimides and co-polyimides based on dioxydiphthalic anhydride
US5089631A (en)	1992-02-18	Dioxydiphthalic anhydride
JPH01294662A (ja)	1989-11-28	ポリマレイミド化合物およびその製造方法
JPH0637555B2 (ja)	1994-05-18	スピロ（ビス）インダン共ポリアミドの製造法
US3992406A (en)	1976-11-16	Preparation of aromatic bisimides
JPH021426A (ja)	1990-01-05	スピロビスインダンビス―オキシフタル酸及びそれらの官能性誘導体
US5434240A (en)	1995-07-18	Poly (imide-ethers)
US3956322A (en)	1976-05-11	Dianhydrides of bis-(orthodicarboxyphenyloxyphenyl)acetylene and bis-(ortho-dicarboxyphenyloxyphenyl)2,2-dichloroethylene
US5166404A (en)	1992-11-24	Dioxydiphthalic acid esters
US2558675A (en)	1951-06-26	N-acyl polyimides of polycarboxylic acids
US5101006A (en)	1992-03-31	Polyimides and copolyimides based on halo-oxydiphthalic anhydrides
EP0142800A2 (fr)	1985-05-29	Procédé de préparation de N-alkylphtalimide et copolymère qui en dérive
US4994579A (en)	1991-02-19	Aromatic ether imides
Morikawa et al.	2000	Synthesis and characterization of novel aromatic polyimides from aromatic diamine and 3, 3''''', 4, 4'''''-p-sexiphenyltetracarboxylic dianhydride