CA1116606A - Procede d'obtention de sels de diarylhalonium - Google Patents

Procede d'obtention de sels de diarylhalonium

Info

Publication number: CA1116606A
Authority: CA; Canada
Prior art keywords: diaryliodonium; bisulfate; salt; mixture; formula
Prior art date: 1978-02-09
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

CA000296756A

Other languages

English (en)

Inventor

James V. Crivello

Julia H. Lam

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.)

General Electric Co

Original Assignee

General Electric 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.)

1978-02-09

Filing date

1978-02-09

Publication date

1982-01-19

1978-02-09 Application filed by General Electric Co filed Critical General Electric Co

1978-02-09 Priority to CA000296756A priority Critical patent/CA1116606A/fr

1982-01-19 Application granted granted Critical

1982-01-19 Publication of CA1116606A publication Critical patent/CA1116606A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 32
150000003839 salts Chemical class 0.000 title claims abstract description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 57
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 40
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 33
239000000203 mixture Substances 0.000 claims abstract description 31
-1 diaryliodonium bisulfate salts Chemical class 0.000 claims abstract description 22
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims abstract description 20
125000005520 diaryliodonium group Chemical group 0.000 claims abstract description 17
239000012955 diaryliodonium Substances 0.000 claims abstract description 16
JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 claims abstract description 14
239000001230 potassium iodate Substances 0.000 claims abstract description 14
229940093930 potassium iodate Drugs 0.000 claims abstract description 14
235000006666 potassium iodate Nutrition 0.000 claims abstract description 14
150000001491 aromatic compounds Chemical class 0.000 claims abstract description 12
230000035484 reaction time Effects 0.000 claims abstract description 9
125000003118 aryl group Chemical group 0.000 claims abstract description 8
238000005859 coupling reaction Methods 0.000 claims abstract description 8
229910052751 metal Inorganic materials 0.000 claims abstract description 7
239000002184 metal Substances 0.000 claims abstract description 7
239000002253 acid Substances 0.000 claims abstract description 6
239000011541 reaction mixture Substances 0.000 claims abstract description 6
230000015572 biosynthetic process Effects 0.000 claims abstract description 5
229910052785 arsenic Inorganic materials 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
229910052698 phosphorus Inorganic materials 0.000 claims abstract description 4
150000001450 anions Chemical group 0.000 claims abstract description 3
229910052787 antimony Inorganic materials 0.000 claims abstract description 3
229910052736 halogen Inorganic materials 0.000 claims abstract description 3
238000005649 metathesis reaction Methods 0.000 claims abstract description 3
125000000623 heterocyclic group Chemical group 0.000 claims abstract 3
229910021645 metal ion Inorganic materials 0.000 claims abstract 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 claims description 4
HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 3
229940078552 o-xylene Drugs 0.000 claims description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims 1
150000001805 chlorine compounds Chemical group 0.000 claims 1
239000011574 phosphorus Substances 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 9
229940032330 sulfuric acid Drugs 0.000 description 7
JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
229910000343 potassium bisulfate Inorganic materials 0.000 description 6
238000003756 stirring Methods 0.000 description 6
PWGVOCGNHYMDLS-UHFFFAOYSA-N 3-(2-methoxyethoxy)propan-1-amine Chemical compound COCCOCCCN PWGVOCGNHYMDLS-UHFFFAOYSA-N 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
235000021028 berry Nutrition 0.000 description 2
YCZWJBIXAUQULS-UHFFFAOYSA-M bis(4-methylphenyl)iodanium;bromide Chemical compound [Br-].C1=CC(C)=CC=C1[I+]C1=CC=C(C)C=C1 YCZWJBIXAUQULS-UHFFFAOYSA-M 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
229960004132 diethyl ether Drugs 0.000 description 2
BCQKUSCWNFMCKI-UHFFFAOYSA-M diphenyliodanium;hydrogen sulfate Chemical compound OS([O-])(=O)=O.C=1C=CC=CC=1[I+]C1=CC=CC=C1 BCQKUSCWNFMCKI-UHFFFAOYSA-M 0.000 description 2
229940035423 ethyl ether Drugs 0.000 description 2
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000000243 solution Substances 0.000 description 2
PQLLEAYSRJFMFF-UHFFFAOYSA-N sulfuric acid;hydroiodide Chemical compound I.OS(O)(=O)=O PQLLEAYSRJFMFF-UHFFFAOYSA-N 0.000 description 2
SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 description 1
229910017048 AsF6 Inorganic materials 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
229910019391 Mg(AsF6)2 Inorganic materials 0.000 description 1
229910019398 NaPF6 Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007806 chemical reaction intermediate Substances 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
230000002301 combined effect Effects 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
MBAKFIZHTUAVJN-UHFFFAOYSA-I hexafluoroantimony(1-);hydron Chemical compound F.F[Sb](F)(F)(F)F MBAKFIZHTUAVJN-UHFFFAOYSA-I 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
239000003999 initiator Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
JLUCVDLESNBWQK-UHFFFAOYSA-N iodyl hydrogen sulfate Chemical compound I(=O)(=O)OS(O)(=O)=O JLUCVDLESNBWQK-UHFFFAOYSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229940073584 methylene chloride Drugs 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000006501 nitrophenyl group Chemical group 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229910001546 potassium hexafluoroantimonate(V) Inorganic materials 0.000 description 1
229910001541 potassium hexafluoroarsenate(V) Inorganic materials 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
229910001542 sodium hexafluoroarsenate(V) Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000296756A 1978-02-09 1978-02-09 Procede d'obtention de sels de diarylhalonium Expired CA1116606A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000296756A CA1116606A (fr)	1978-02-09	1978-02-09	Procede d'obtention de sels de diarylhalonium

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000296756A CA1116606A (fr)	1978-02-09	1978-02-09	Procede d'obtention de sels de diarylhalonium

Publications (1)

Publication Number	Publication Date
CA1116606A true CA1116606A (fr)	1982-01-19

Family

ID=4110755

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000296756A Expired CA1116606A (fr)	1978-02-09	1978-02-09	Procede d'obtention de sels de diarylhalonium

Country Status (1)

Country	Link
CA (1)	CA1116606A (fr)

1978
- 1978-02-09 CA CA000296756A patent/CA1116606A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-01-19	MKEX	Expiry

Publication	Publication Date	Title
US4151175A (en)	1979-04-24	Method for making diarylhalonium salts
US3981897A (en)	1976-09-21	Method for making certain halonium salt photoinitiators
US4250311A (en)	1981-02-10	P, As, and Sb hexafluoride onium salts as photoinitiators
US4238394A (en)	1980-12-09	Method for making diaryliodonium salts
GB1433460A (en)	1976-04-28	Process for the manufacture of aromatic 1,3-diketones
US5012001A (en)	1991-04-30	Triaryl sulfonium photoinitiators
JP2711491B2 (ja)	1998-02-10	スルホニウム錯体またはオキソスルホニウム錯体
CA1116606A (fr)	1982-01-19	Procede d'obtention de sels de diarylhalonium
US4131617A (en)	1978-12-26	Preparation of new isobutylramide derivatives
EP0020896B1 (fr)	1983-11-16	Procédé pour la préparation de dithiafulvènes géminaux dithiolates et leurs analogues séléniés
JPS61100557A (ja)	1986-05-19	トリアリールスルホニウム塩およびその製法
Kober	1959	A New Class of Sulfenyl Derivatives; Perhalogenated Aliphatic Sulfenyl Fluorides1
US4659840A (en)	1987-04-21	Method for preparing diaryl iodonium salts
US4786441A (en)	1988-11-22	Preparation of iodonium and sulfonium triflates
US4197417A (en)	1980-04-08	Process for the manufacture of o-benzyl toluenes
US4329300A (en)	1982-05-11	Method for making diaryliodonium polyhalometalloid salts
US2994711A (en)	1961-08-01	Triorganosiloxymetal oxides
JPH0348654A (ja)	1991-03-01	スルホニウム化合物の製造方法
US4061660A (en)	1977-12-06	Process for synthesis of coenzyme Q compounds
GILMAN et al.	1959	Cleavage studies of some organogermanium compounds
US3953531A (en)	1976-04-27	Alkylhydroquinone and process for producing the same
FR2476078A1 (fr)	1981-08-21	Procede de fabrication d'un sel complexe de triarylsulfonium
KR850005838A (ko)	1985-09-26	1,3,2-디옥사보리난의 제조방법
US4062879A (en)	1977-12-13	Process for synthesis of coenzyme Q compounds
US4353836A (en)	1982-10-12	4-(2,5-Dihydroxyphen-1-yl)-crotonic acid and its derivatives, and the preparation of these compounds