CA1248969A - Chlorures de trifluoromethylbenzal et methode de preparation - Google Patents

Chlorures de trifluoromethylbenzal et methode de preparation

Info

Publication number: CA1248969A
Authority: CA; Canada
Prior art keywords: trifluoromethyl; benzal; trichloromethyl; xylene; benzal chloride
Prior art date: 1981-10-30
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.): Expired

Application number

CA000389124A

Other languages

English (en)

Inventor

R. Simon Bierenbaum

David Y. Tang

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.)

Occidental Chemical Corp

Original Assignee

Occidental Chemical Corp

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.)

1981-10-30

Filing date

1981-10-30

Publication date

1989-01-17

1981-10-30 Application filed by Occidental Chemical Corp filed Critical Occidental Chemical Corp

1981-10-30 Priority to CA000389124A priority Critical patent/CA1248969A/fr

1989-01-17 Application granted granted Critical

1989-01-17 Publication of CA1248969A publication Critical patent/CA1248969A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 29
238000002360 preparation method Methods 0.000 title claims abstract description 12
VCGJIIDFWDVVQE-UHFFFAOYSA-N (1,1-dichloro-2,2,2-trifluoroethyl)benzene Chemical class FC(F)(F)C(Cl)(Cl)C1=CC=CC=C1 VCGJIIDFWDVVQE-UHFFFAOYSA-N 0.000 title claims description 7
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims abstract description 23
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims abstract description 21
239000003054 catalyst Substances 0.000 claims abstract description 16
AXVLZOYLQOEKAO-UHFFFAOYSA-N 1,1,2,2,2-pentachloroethylbenzene Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)C1=CC=CC=C1 AXVLZOYLQOEKAO-UHFFFAOYSA-N 0.000 claims abstract description 14
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 14
229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 14
229910052736 halogen Inorganic materials 0.000 claims abstract description 10
150000002367 halogens Chemical group 0.000 claims abstract description 10
239000008096 xylene Substances 0.000 claims abstract description 8
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 6
VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical group Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 8
GDZMMXXMEMTSJY-UHFFFAOYSA-N 1-(dichloromethyl)-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(C(Cl)Cl)C=C1 GDZMMXXMEMTSJY-UHFFFAOYSA-N 0.000 claims description 7
CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 claims description 6
BEOBZEOPTQQELP-UHFFFAOYSA-N 4-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=C(C=O)C=C1 BEOBZEOPTQQELP-UHFFFAOYSA-N 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
NMTUHPSKJJYGML-UHFFFAOYSA-N 3-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC(C=O)=C1 NMTUHPSKJJYGML-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
YHSJPSUQWJNGQJ-UHFFFAOYSA-N 1-(dichloromethyl)-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(C(Cl)Cl)=C1 YHSJPSUQWJNGQJ-UHFFFAOYSA-N 0.000 claims 2
ZDVRPKUWYQVVDX-UHFFFAOYSA-N 2-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC=C1C=O ZDVRPKUWYQVVDX-UHFFFAOYSA-N 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 abstract description 10
239000000047 product Substances 0.000 abstract description 5
239000000126 substance Substances 0.000 abstract description 5
-1 TRIFLUOROMETHYL BENZAL Chemical class 0.000 abstract description 4
150000001875 compounds Chemical class 0.000 abstract description 4
239000000543 intermediate Substances 0.000 abstract description 4
239000007858 starting material Substances 0.000 abstract description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 11
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
ADZRLHZKUYJIOM-UHFFFAOYSA-N 1-(dichloromethyl)-4-(trichloromethyl)benzene Chemical compound ClC(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 ADZRLHZKUYJIOM-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000000306 component Substances 0.000 description 5
238000003682 fluorination reaction Methods 0.000 description 5
239000000376 reactant Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
VCNFMVBDSQQJSO-UHFFFAOYSA-N 1-(dichloromethyl)-3-(trichloromethyl)benzene Chemical compound ClC(Cl)C1=CC=CC(C(Cl)(Cl)Cl)=C1 VCNFMVBDSQQJSO-UHFFFAOYSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
238000004821 distillation Methods 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
QICXTGCEPZAKNJ-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5-(chloromethyl)-6-methylbenzene Chemical group CC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1CCl QICXTGCEPZAKNJ-UHFFFAOYSA-N 0.000 description 2
FXYNMGAFYPNJIZ-UHFFFAOYSA-N 1-(dichloromethyl)-2,5-difluoro-3-(trichloromethyl)benzene Chemical compound FC1=CC(C(Cl)Cl)=C(F)C(C(Cl)(Cl)Cl)=C1 FXYNMGAFYPNJIZ-UHFFFAOYSA-N 0.000 description 2
OHHANDXPWMGPQC-UHFFFAOYSA-N 2,5-dichloro-1-(dichloromethyl)-3-(trichloromethyl)benzene Chemical compound ClC(Cl)C1=CC(Cl)=CC(C(Cl)(Cl)Cl)=C1Cl OHHANDXPWMGPQC-UHFFFAOYSA-N 0.000 description 2
JNEGPINFRRYWDC-UHFFFAOYSA-N 2-chloro-1-(dichloromethyl)-4-(trichloromethyl)benzene Chemical compound ClC(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1Cl JNEGPINFRRYWDC-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
CINIYRNQWGWFPX-UHFFFAOYSA-N 1,2,3-trichloro-4-(1,1-dichloroethyl)benzene Chemical class ClC1=C(C(=C(C(C)(Cl)Cl)C=C1)Cl)Cl CINIYRNQWGWFPX-UHFFFAOYSA-N 0.000 description 1
BDUGOKVYMIOQIH-UHFFFAOYSA-N 1,3-dichloro-4-(dichloromethyl)-2-(trichloromethyl)benzene Chemical compound ClC(Cl)C1=CC=C(Cl)C(C(Cl)(Cl)Cl)=C1Cl BDUGOKVYMIOQIH-UHFFFAOYSA-N 0.000 description 1
UXMNSLMVCBBGCW-UHFFFAOYSA-N 1-(dichloromethyl)-2-(trichloromethyl)benzene Chemical compound ClC(Cl)C1=CC=CC=C1C(Cl)(Cl)Cl UXMNSLMVCBBGCW-UHFFFAOYSA-N 0.000 description 1
JIJFXGFHPXLJME-UHFFFAOYSA-N 1-(dichloromethyl)-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1C(Cl)Cl JIJFXGFHPXLJME-UHFFFAOYSA-N 0.000 description 1
UBZYFZDZTIHKQN-UHFFFAOYSA-N 1-(dichloromethyl)-2-fluoro-3-(trichloromethyl)benzene Chemical compound FC1=C(C(Cl)Cl)C=CC=C1C(Cl)(Cl)Cl UBZYFZDZTIHKQN-UHFFFAOYSA-N 0.000 description 1
IRQXUHCPHJDFTD-UHFFFAOYSA-N 1-(dichloromethyl)-2-fluoro-4-(trichloromethyl)benzene Chemical compound FC1=CC(C(Cl)(Cl)Cl)=CC=C1C(Cl)Cl IRQXUHCPHJDFTD-UHFFFAOYSA-N 0.000 description 1
ICPWLCJCJOBNJW-UHFFFAOYSA-N 1-(dichloromethyl)-3-fluoro-5-(trichloromethyl)benzene Chemical compound FC1=CC(C(Cl)Cl)=CC(C(Cl)(Cl)Cl)=C1 ICPWLCJCJOBNJW-UHFFFAOYSA-N 0.000 description 1
MFIOEEWGBMJNGG-UHFFFAOYSA-N 1-(dichloromethyl)-4-fluorobenzene Chemical compound FC1=CC=C(C(Cl)Cl)C=C1 MFIOEEWGBMJNGG-UHFFFAOYSA-N 0.000 description 1
OUNFMIAANXWNKM-UHFFFAOYSA-N 1-bromo-3-(dichloromethyl)-5-(trichloromethyl)benzene Chemical compound ClC(Cl)C1=CC(Br)=CC(C(Cl)(Cl)Cl)=C1 OUNFMIAANXWNKM-UHFFFAOYSA-N 0.000 description 1
NRUFSQOCJJSPRZ-UHFFFAOYSA-N 1-chloro-2-(dichloromethyl)-4-(trichloromethyl)benzene Chemical compound ClC(Cl)C1=CC(C(Cl)(Cl)Cl)=CC=C1Cl NRUFSQOCJJSPRZ-UHFFFAOYSA-N 0.000 description 1
AMFRNCWLOKTDFW-UHFFFAOYSA-N 1-chloro-3-(dichloromethyl)-5-(trichloromethyl)benzene Chemical compound ClC(Cl)C1=CC(Cl)=CC(C(Cl)(Cl)Cl)=C1 AMFRNCWLOKTDFW-UHFFFAOYSA-N 0.000 description 1
KQQYGFHQWABLOK-UHFFFAOYSA-N 1-chloro-4-(dichloromethyl)-2-(trichloromethyl)benzene Chemical compound ClC(Cl)C1=CC=C(Cl)C(C(Cl)(Cl)Cl)=C1 KQQYGFHQWABLOK-UHFFFAOYSA-N 0.000 description 1
VYTJUXVSBPCLKK-UHFFFAOYSA-N 2,5-dichloro-1-(dichloromethyl)-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Cl)=CC(C(Cl)Cl)=C1Cl VYTJUXVSBPCLKK-UHFFFAOYSA-N 0.000 description 1
ZGOYGRFFVTZXCB-UHFFFAOYSA-N 2-(dichloromethyl)-1-fluoro-4-(trichloromethyl)benzene Chemical compound FC1=CC=C(C(Cl)(Cl)Cl)C=C1C(Cl)Cl ZGOYGRFFVTZXCB-UHFFFAOYSA-N 0.000 description 1
SKRIOGWKQFGJRJ-UHFFFAOYSA-N 2-bromo-1-(dichloromethyl)-3-(trichloromethyl)benzene Chemical compound ClC(Cl)C1=CC=CC(C(Cl)(Cl)Cl)=C1Br SKRIOGWKQFGJRJ-UHFFFAOYSA-N 0.000 description 1
MIBMFCRHHADYPF-UHFFFAOYSA-N 2-bromo-1-(dichloromethyl)-4-(trichloromethyl)benzene Chemical compound ClC(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1Br MIBMFCRHHADYPF-UHFFFAOYSA-N 0.000 description 1
LNCLDJOAGRXHOX-UHFFFAOYSA-N 2-bromo-4-(dichloromethyl)-1-(trichloromethyl)benzene Chemical compound ClC(Cl)C1=CC=C(C(Cl)(Cl)Cl)C(Br)=C1 LNCLDJOAGRXHOX-UHFFFAOYSA-N 0.000 description 1
QZMLDQPTXYRVKO-UHFFFAOYSA-N 2-chloro-1-(dichloromethyl)-3-(trichloromethyl)benzene Chemical compound ClC(Cl)C1=CC=CC(C(Cl)(Cl)Cl)=C1Cl QZMLDQPTXYRVKO-UHFFFAOYSA-N 0.000 description 1
JRGPZGQUSSNNPY-UHFFFAOYSA-N 2-chloro-1-(dichloromethyl)-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(C(Cl)Cl)C(Cl)=C1 JRGPZGQUSSNNPY-UHFFFAOYSA-N 0.000 description 1
ASTGADBUDORAJG-UHFFFAOYSA-N 2-chloro-4-(dichloromethyl)-1-(trichloromethyl)benzene Chemical compound ClC(Cl)C1=CC=C(C(Cl)(Cl)Cl)C(Cl)=C1 ASTGADBUDORAJG-UHFFFAOYSA-N 0.000 description 1
PAYMGCUXRKCOCU-UHFFFAOYSA-N 4-(dichloromethyl)-2-fluoro-1-(trichloromethyl)benzene Chemical compound FC1=CC(C(Cl)Cl)=CC=C1C(Cl)(Cl)Cl PAYMGCUXRKCOCU-UHFFFAOYSA-N 0.000 description 1
229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
230000002730 additional effect Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
GICWIDZXWJGTCI-UHFFFAOYSA-I molybdenum pentachloride Chemical compound Cl[Mo](Cl)(Cl)(Cl)Cl GICWIDZXWJGTCI-UHFFFAOYSA-I 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA000389124A 1981-10-30 1981-10-30 Chlorures de trifluoromethylbenzal et methode de preparation Expired CA1248969A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000389124A CA1248969A (fr)	1981-10-30	1981-10-30	Chlorures de trifluoromethylbenzal et methode de preparation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000389124A CA1248969A (fr)	1981-10-30	1981-10-30	Chlorures de trifluoromethylbenzal et methode de preparation

Publications (1)

Publication Number	Publication Date
CA1248969A true CA1248969A (fr)	1989-01-17

Family

ID=4121306

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000389124A Expired CA1248969A (fr)	1981-10-30	1981-10-30	Chlorures de trifluoromethylbenzal et methode de preparation

Country Status (1)

Country	Link
CA (1)	CA1248969A (fr)

1981
- 1981-10-30 CA CA000389124A patent/CA1248969A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2006-01-17	MKEX	Expiry

Publication	Publication Date	Title
US4590315A (en)	1986-05-20	Process for the preparation of halo aromatic compounds
US4367348A (en)	1983-01-04	Novel trifluoromethyl benzal chlorides and process for the preparation thereof
JPS60228429A (ja)	1985-11-13	核塩素化化合物の製造法
US4780559A (en)	1988-10-25	Process for preparing organic fluorides
US4847442A (en)	1989-07-11	Process for the preparation of difluorobenzenes
CA1248969A (fr)	1989-01-17	Chlorures de trifluoromethylbenzal et methode de preparation
US4575571A (en)	1986-03-11	Process for the simultaneous halogenation and fluorination of aromatic derivatives
US4500471A (en)	1985-02-19	Preparation of trifluoromethyl-benzoyl halides
US4568781A (en)	1986-02-04	Preparation of fluorine-substituted aromatic compounds
JP3557624B2 (ja)	2004-08-25	４，６−ジニトロハロベンゼンの製造方法
EP0460639B1 (fr)	1995-12-27	Procédé de préparation de 3,5-difluoroaniline et son dérivé
US4952719A (en)	1990-08-28	Process for the preparation of halo aromatic compounds
JPH0822851B2 (ja)	1996-03-06	２，３，５−トリクロロピリジンの製造方法
EP0038223B1 (fr)	1984-08-08	Procédé pour la préparation d'halogénures d'acides trifluorométhylbenzoiques
EP0155093B1 (fr)	1987-10-21	Procédé pour la préparation de dérivés aromatiques contenant du fluor
US5208394A (en)	1993-05-04	Process for producing chlorofluorobenzenes
EP0355719A1 (fr)	1990-02-28	Procédé pour la fabrication de chlorofluorobenzènes
EP0493030A1 (fr)	1992-07-01	Procédé pour la préparation de difluorobenzènes
US5648570A (en)	1997-07-15	Process for preparing substituted chloroaromatics
JPS6147426A (ja)	1986-03-07	フツ素化環式炭化水素類の製法
US5233104A (en)	1993-08-03	Process for trifluoromethylation of aromatic compounds
JPS63203636A (ja)	1988-08-23	ハロゲン化芳香族化合物のフツ素化方法
JPS62289547A (ja)	1987-12-16	４−フルオロアニリンの製法
JPS6236336A (ja)	1987-02-17	ベンゾトリフルオライド誘導体の製法
JPH0155253B2 (fr)	1989-11-22