IL95426A - Preparation of Lupetal Acid Derivatives - Google Patents

Preparation of Lupetal Acid Derivatives

Info

Publication number: IL95426A
Authority: IL; Israel
Prior art keywords: process according; formula; temperature; anhydride; bromine
Prior art date: 1989-09-11

Application number

IL9542690A

Other languages

English (en)

Hebrew (he)

Other versions

IL95426A0 (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.)

1989-09-11

Filing date

1990-08-20

Publication date

1996-01-19

1990-08-20 Application filed by Occidental Chem Co filed Critical Occidental Chem Co

1991-06-30 Publication of IL95426A0 publication Critical patent/IL95426A0/xx

1996-01-19 Publication of IL95426A publication Critical patent/IL95426A/en

Links

238000002360 preparation method Methods 0.000 title claims description 19
239000002253 acid Substances 0.000 title description 11
150000008064 anhydrides Chemical group 0.000 claims description 97
238000000034 method Methods 0.000 claims description 70
229910052794 bromium Inorganic materials 0.000 claims description 56
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 54
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 52
238000006243 chemical reaction Methods 0.000 claims description 32
150000002367 halogens Chemical group 0.000 claims description 28
229910052736 halogen Inorganic materials 0.000 claims description 27
239000000376 reactant Substances 0.000 claims description 22
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical group ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 17
239000011541 reaction mixture Substances 0.000 claims description 16
239000003795 chemical substances by application Substances 0.000 claims description 14
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 11
239000003999 initiator Substances 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 11
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical group BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 10
150000003254 radicals Chemical class 0.000 claims description 10
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 9
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 5
239000007791 liquid phase Substances 0.000 claims description 5
239000007858 starting material Substances 0.000 claims description 5
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical class CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 4
229920006391 phthalonitrile polymer Polymers 0.000 claims description 4
SZSLISKYJBQHQC-UHFFFAOYSA-N 4-chlorobenzene-1,2-dicarbonitrile Chemical compound ClC1=CC=C(C#N)C(C#N)=C1 SZSLISKYJBQHQC-UHFFFAOYSA-N 0.000 claims description 3
RNOVZBXRHVJOCI-UHFFFAOYSA-N 4-chlorobenzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1C(Cl)=O RNOVZBXRHVJOCI-UHFFFAOYSA-N 0.000 claims description 3
CJCLZEXTJARVTC-UHFFFAOYSA-N 5-chlorocyclohex-3-ene-1,2-dicarbonitrile Chemical compound ClC1CC(C#N)C(C#N)C=C1 CJCLZEXTJARVTC-UHFFFAOYSA-N 0.000 claims description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
LCZHQERVPVTGHA-UHFFFAOYSA-N 5-chlorocyclohex-3-ene-1,2-dicarbonyl chloride Chemical compound ClC1CC(C(Cl)=O)C(C(Cl)=O)C=C1 LCZHQERVPVTGHA-UHFFFAOYSA-N 0.000 claims description 2
XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical class N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 claims description 2
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims description 2
230000005855 radiation Effects 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 4
125000001246 bromo group Chemical group Br* 0.000 claims 2
239000000047 product Substances 0.000 description 16
-1 halogen Chemical class 0.000 description 10
229920006395 saturated elastomer Polymers 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
238000006356 dehydrogenation reaction Methods 0.000 description 8
239000000203 mixture Substances 0.000 description 8
238000004458 analytical method Methods 0.000 description 7
238000005899 aromatization reaction Methods 0.000 description 7
238000004817 gas chromatography Methods 0.000 description 7
239000000543 intermediate Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
239000007789 gas Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
238000004821 distillation Methods 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
238000003756 stirring Methods 0.000 description 4
150000001993 dienes Chemical class 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
238000005698 Diels-Alder reaction Methods 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
239000004642 Polyimide Substances 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
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 2
150000001408 amides Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
239000012467 final product Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000012535 impurity Substances 0.000 description 2
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
239000000178 monomer Substances 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
229920001721 polyimide Polymers 0.000 description 2
238000000926 separation method Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical class C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 1
WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
ZDFBKZUDCQQKAC-UHFFFAOYSA-N 1-bromo-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Br)C=C1 ZDFBKZUDCQQKAC-UHFFFAOYSA-N 0.000 description 1
COXCGWKSEPPDAA-UHFFFAOYSA-N 2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)C#N COXCGWKSEPPDAA-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
CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 1
SUDNYBFCHLZMQX-UHFFFAOYSA-N 4-chloro-4-fluorocyclohexane-1,2-dicarbonitrile Chemical compound FC1(Cl)CCC(C#N)C(C#N)C1 SUDNYBFCHLZMQX-UHFFFAOYSA-N 0.000 description 1
JDBDDNFATWXGQZ-UHFFFAOYSA-N 5-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1=CC(C)CC2C(=O)OC(=O)C12 JDBDDNFATWXGQZ-UHFFFAOYSA-N 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
229910014265 BrCl Inorganic materials 0.000 description 1
GBFZNJZPOZUUAJ-UHFFFAOYSA-N C(C1C(C(=O)Cl)C[ClH]CC1)(=O)Cl Chemical compound C(C1C(C(=O)Cl)C[ClH]CC1)(=O)Cl GBFZNJZPOZUUAJ-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical class F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
238000006136 alcoholysis reaction Methods 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
238000005915 ammonolysis reaction Methods 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
150000004768 bromobenzenes Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
YBNZGVPRVTWANT-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarbonitrile Chemical class N#CC1CCC=CC1C#N YBNZGVPRVTWANT-UHFFFAOYSA-N 0.000 description 1
MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexediene Natural products C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
239000000975 dye Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
MUTGBJKUEZFXGO-UHFFFAOYSA-N hexahydrophthalic anhydride Chemical class C1CCCC2C(=O)OC(=O)C21 MUTGBJKUEZFXGO-UHFFFAOYSA-N 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
238000007348 radical reaction Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000007787 solid 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
238000005292 vacuum distillation Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/567—Preparation of carboxylic acid anhydrides by reactions not involving carboxylic acid anhydride groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Furan Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL9542690A 1989-09-11 1990-08-20 Preparation of Lupetal Acid Derivatives IL95426A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/405,606 US5049682A (en)	1989-09-11	1989-09-11	Process for the preparation of halophthalic anhydrides

Publications (2)

Publication Number	Publication Date
IL95426A0 IL95426A0 (en)	1991-06-30
IL95426A true IL95426A (en)	1996-01-19

Family

ID=23604397

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9542690A IL95426A (en)	1989-09-11	1990-08-20	Preparation of Lupetal Acid Derivatives

Country Status (6)

Country	Link
US (1)	US5049682A (fr)
EP (1)	EP0417691A3 (fr)
JP (1)	JP3020575B2 (fr)
BR (1)	BR9004479A (fr)
CA (1)	CA2023724A1 (fr)
IL (1)	IL95426A (fr)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5233054A (en) *	1989-09-11	1993-08-03	Occidental Chemical Corporation	Process for the preparation of halophthalic anhydrides
US5206391A (en) *	1989-09-11	1993-04-27	Occidental Chemical Corporation	Process for the preparation of halophthalic anhydrides
JP3191489B2 (ja) *	1993-05-27	2001-07-23	三菱化学株式会社	ハロゲン化無水フタル酸の製造法
US5322954A (en) *	1993-05-28	1994-06-21	Occidental Chemical Corporation	Synthesis of 4-substituted phthalic anhydrides
US6498224B1 (en)	2001-12-05	2002-12-24	General Electric Company	Methods for the preparation poly(etherimide)s
US6576770B1 (en)	2001-12-05	2003-06-10	General Electric Company	Preparation of substituted phthalic anhydrides and substituted phthalimides
US6528663B1 (en)	2001-12-05	2003-03-04	General Electric Company	Methods for the preparation of 4-chlorophthalic anhydride
US6649773B2 (en)	2002-03-22	2003-11-18	General Electric Company	Method for the manufacture of halophthalic acids and anhydrides
US6657067B2 (en)	2002-03-22	2003-12-02	General Electric Company	Method for the manufacture of chlorophthalic anhydride
US6657068B2 (en)	2002-03-22	2003-12-02	General Electric Company	Liquid phase oxidation of halogenated ortho-xylenes
US6881815B2 (en) *	2002-09-25	2005-04-19	General Electric Company	Method for the preparation poly(etherimide)s
US7541489B2 (en)	2004-06-30	2009-06-02	Sabic Innovative Plastics Ip B.V.	Method of making halophthalic acids and halophthalic anhydrides
CN101857582A (zh) *	2010-04-21	2010-10-13	大连理工大学	一种4-氯代苯酐的制备方法
CN115521279B (zh) *	2021-06-25	2024-03-26	中国石油化工股份有限公司	一种4-卤代苯酐的制备方法及利用该方法得到的4-卤代苯酐

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4560773A (en) *	1984-04-16	1985-12-24	Stauffer Chemical Company	Process for preparing substituted phthalic anhydrides
US4559405A (en) *	1984-04-16	1985-12-17	Stauffer Chemical Company	Process for preparing substituted phthalic anhydrides
BR8900447A (pt) *	1988-02-24	1989-09-26	Occidental Chem Co	Processo aperfeicoado de desidrogenacao

1989
- 1989-09-11 US US07/405,606 patent/US5049682A/en not_active Expired - Lifetime
1990
- 1990-08-20 IL IL9542690A patent/IL95426A/en not_active IP Right Cessation
- 1990-08-21 CA CA002023724A patent/CA2023724A1/fr not_active Abandoned
- 1990-09-10 BR BR909004479A patent/BR9004479A/pt not_active Application Discontinuation
- 1990-09-10 EP EP19900117382 patent/EP0417691A3/en not_active Ceased
- 1990-09-11 JP JP2241068A patent/JP3020575B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
BR9004479A (pt)	1991-09-10
CA2023724A1 (fr)	1991-03-12
JP3020575B2 (ja)	2000-03-15
JPH03106871A (ja)	1991-05-07
US5049682A (en)	1991-09-17
IL95426A0 (en)	1991-06-30
EP0417691A3 (en)	1992-01-02
EP0417691A2 (fr)	1991-03-20

Legal Events

Date	Code	Title
1996-06-18	FF	Patent granted
1996-11-14	KB	Patent renewed
2001-06-14	RH	Patent void

Publication	Publication Date	Title
IL95426A (en)	1996-01-19	Preparation of Lupetal Acid Derivatives
US5233054A (en)	1993-08-03	Process for the preparation of halophthalic anhydrides
US5489694A (en)	1996-02-06	Preparation of R/S-γ-lipoic acid or R/S-α-lipoic acid
US5206391A (en)	1993-04-27	Process for the preparation of halophthalic anhydrides
EP0614874B1 (fr)	1999-01-27	Procédé de fabrication d'esters halogénés d'acides carboxyliques ou dicarboxyliques
Henne et al.	1951	Positive Bromine from Perfluorinated N-Bromoimides1
US4962206A (en)	1990-10-09	Process for the preparation of 4-bromophthalic anhydride
US6187952B1 (en)	2001-02-13	Two-step production of 3-chloro-4-fluoro-benzoyl chloride by chlorination
US2841593A (en)	1958-07-01	Reaction of substituted benzene, chlorine, and substituted maleic anhydride and products thereof
US5047553A (en)	1991-09-10	Tetrafluoro-N-phenylphthalimide
Barusch et al.	1953	Preparation of β-Hydroxydialkyl Peroxides
US5502261A (en)	1996-03-26	Process for preparing 2,2'-bis(halomethyl)-1,1'-binaphthyl
US4968830A (en)	1990-11-06	Aromatization process
US4424393A (en)	1984-01-03	Process of preparation of substituted diphenyl ethers
CA2214637A1 (fr)	1996-09-12	Procede de preparation d'esters d'acide stilbene-dicarboxylique
JPS625899B2 (fr)	1987-02-07
EP0007154A1 (fr)	1980-01-23	Procédé de préparation de dérivés cyclopropaniques, intermédiaires dans la synthèse d'insecticides pyréthroides
US5153334A (en)	1992-10-06	Partially fluorinated tetracarboxylic acid and the dianhydride thereof
CS208795B2 (en)	1981-09-15	Method of making the 3-phenoxybenzaldehydes
US5274126A (en)	1993-12-28	Partially fluorinated tetracarboxylic acid and the dianhydride thereof, a process for their preparation and their use
US3009947A (en)	1961-11-21	Production of chloralkyl esters of acrylic acid and its substitution products
US3428672A (en)	1969-02-18	4-substituted-2,3,5,6-tetrafluoronitrosobenzene
CA1149821A (fr)	1983-07-12	Trichlorophloroglucinol, tripropylether, trichlorophloroglucinol triisopropylether, leur preparation et hydrolyse en trichlorophloroglucinol
CA1195695A (fr)	1985-10-22	Preparation de meta-aryloxy-benzaldehydes
JPS6043051B2 (ja)	1985-09-26	ｍ−フェノキシトルエンの側鎖の臭素化方法