CA1270853A - Preparation d'amines (hydrocarbylthio)aromatiques - Google Patents

Preparation d'amines (hydrocarbylthio)aromatiques

Info

Publication number: CA1270853A
Authority: CA; Canada
Prior art keywords: aromatic; iodide; metal halide; hydrocarbylthio; hydrocarbyl
Prior art date: 1987-03-06
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

CA000531365A

Other languages

English (en)

Inventor

Robert Lynn Davis

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.)

Albemarle Corp

Original Assignee

Ethyl 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.)

1987-03-06

Filing date

1987-03-06

Publication date

1990-06-26

1987-03-06 Application filed by Ethyl Corp filed Critical Ethyl Corp

1987-03-06 Priority to CA000531365A priority Critical patent/CA1270853A/fr

1990-06-26 Application granted granted Critical

1990-06-26 Publication of CA1270853A publication Critical patent/CA1270853A/fr

Status Expired legal-status Critical Current

Links

150000004982 aromatic amines Chemical class 0.000 title claims abstract description 8
238000004519 manufacturing process Methods 0.000 title abstract description 5
125000003118 aryl group Chemical group 0.000 claims abstract description 16
229920000768 polyamine Polymers 0.000 claims abstract description 13
-1 hydrocarbyl disulfide Chemical compound 0.000 claims abstract description 10
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims abstract description 5
229910052751 metal Inorganic materials 0.000 claims abstract description 5
239000002184 metal Substances 0.000 claims abstract description 5
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 3
150000001340 alkali metals Chemical class 0.000 claims abstract description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 18
229910001507 metal halide Inorganic materials 0.000 claims description 9
150000005309 metal halides Chemical class 0.000 claims description 9
UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical group I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 claims description 9
230000003197 catalytic effect Effects 0.000 claims description 5
VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims description 4
OKIIEJOIXGHUKX-UHFFFAOYSA-L cadmium iodide Chemical group [Cd+2].[I-].[I-] OKIIEJOIXGHUKX-UHFFFAOYSA-L 0.000 claims description 4
WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical group CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 claims description 4
RLYCRLGLCUXUPO-UHFFFAOYSA-N 2,6-diaminotoluene Chemical compound CC1=C(N)C=CC=C1N RLYCRLGLCUXUPO-UHFFFAOYSA-N 0.000 claims description 3
229910021584 Cobalt(II) iodide Inorganic materials 0.000 claims description 2
AVWLPUQJODERGA-UHFFFAOYSA-L cobalt(2+);diiodide Chemical group [Co+2].[I-].[I-] AVWLPUQJODERGA-UHFFFAOYSA-L 0.000 claims description 2
BQZGVMWPHXIKEQ-UHFFFAOYSA-L iron(ii) iodide Chemical group [Fe+2].[I-].[I-] BQZGVMWPHXIKEQ-UHFFFAOYSA-L 0.000 claims description 2
239000000203 mixture Substances 0.000 claims description 2
229910021595 Copper(I) iodide Inorganic materials 0.000 claims 1
229940075417 cadmium iodide Drugs 0.000 claims 1
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical group I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims 1
229940076136 ferrous iodide Drugs 0.000 claims 1
DYFXGORUJGZJCA-UHFFFAOYSA-N phenylmethanediamine Chemical compound NC(N)C1=CC=CC=C1 DYFXGORUJGZJCA-UHFFFAOYSA-N 0.000 claims 1
239000003054 catalyst Substances 0.000 abstract description 13
238000006243 chemical reaction Methods 0.000 description 19
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 14
239000000047 product Substances 0.000 description 8
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
230000000052 comparative effect Effects 0.000 description 6
VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 5
230000035484 reaction time Effects 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
150000001649 bromium compounds Chemical class 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
150000004694 iodide salts Chemical class 0.000 description 3
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
229910052793 cadmium Inorganic materials 0.000 description 2
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical compound [Co+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 MPMSMUBQXQALQI-UHFFFAOYSA-N 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
229910001509 metal bromide Inorganic materials 0.000 description 2
229910001511 metal iodide Inorganic materials 0.000 description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
229920002635 polyurethane Polymers 0.000 description 2
239000004814 polyurethane Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
ZIXXRXGPBFMPFD-UHFFFAOYSA-N 1-chloro-4-[(4-chlorophenyl)disulfanyl]benzene Chemical class C1=CC(Cl)=CC=C1SSC1=CC=C(Cl)C=C1 ZIXXRXGPBFMPFD-UHFFFAOYSA-N 0.000 description 1
KZXDETHBUVFJMZ-UHFFFAOYSA-N 2-ethylbenzene-1,3-diamine Chemical compound CCC1=C(N)C=CC=C1N KZXDETHBUVFJMZ-UHFFFAOYSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
229910021575 Iron(II) bromide Inorganic materials 0.000 description 1
229910021579 Iron(II) iodide Inorganic materials 0.000 description 1
229910021576 Iron(III) bromide Inorganic materials 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910001513 alkali metal bromide Inorganic materials 0.000 description 1
229910001516 alkali metal iodide Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
150000004984 aromatic diamines Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000005110 aryl thio group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000012467 final product Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 description 1
RQQRAHKHDFPBMC-UHFFFAOYSA-L lead(ii) iodide Chemical compound I[Pb]I RQQRAHKHDFPBMC-UHFFFAOYSA-L 0.000 description 1
239000011968 lewis acid catalyst Substances 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
YFDLHELOZYVNJE-UHFFFAOYSA-L mercury diiodide Chemical compound I[Hg]I YFDLHELOZYVNJE-UHFFFAOYSA-L 0.000 description 1
229910001510 metal chloride Inorganic materials 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000036647 reaction Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 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
FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229940102001 zinc bromide Drugs 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1

Landscapes

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

CA000531365A 1987-03-06 1987-03-06 Preparation d'amines (hydrocarbylthio)aromatiques Expired CA1270853A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000531365A CA1270853A (fr)	1987-03-06	1987-03-06	Preparation d'amines (hydrocarbylthio)aromatiques

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000531365A CA1270853A (fr)	1987-03-06	1987-03-06	Preparation d'amines (hydrocarbylthio)aromatiques

Publications (1)

Publication Number	Publication Date
CA1270853A true CA1270853A (fr)	1990-06-26

Family

ID=4135113

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000531365A Expired CA1270853A (fr)	1987-03-06	1987-03-06	Preparation d'amines (hydrocarbylthio)aromatiques

Country Status (1)

Country	Link
CA (1)	CA1270853A (fr)

1987
- 1987-03-06 CA CA000531365A patent/CA1270853A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2002-06-26	MKLA	Lapsed

Publication	Publication Date	Title
US5068445A (en)	1991-11-26	Process for the preparation of organic disulphides and polysulphides
US4594453A (en)	1986-06-10	Process for preparing (hydrocarbylthio)aromatic amines
US4670598A (en)	1987-06-02	Process for preparing (hydrocarbylthio)aromatic amines
JPH09100265A (ja)	1997-04-15	芳香族カルバメートの製造方法
EP0281697B1 (fr)	1990-01-24	Procédé de préparation d'amines hydrocarbylthioiques et leur utilisation
US6683204B1 (en)	2004-01-27	Method for producing monoisocyanates and oligoisocyanates
US4670597A (en)	1987-06-02	Process for preparing (hydrocarbylthio) aromatic amines
CA1270853A (fr)	1990-06-26	Preparation d'amines (hydrocarbylthio)aromatiques
KR900008118B1 (ko)	1990-10-31	티오에테르로부터 메르캅탄의 촉매적 제조방법
US4889955A (en)	1989-12-26	Preparation of (hydrocarbylthio)aromatic amines
US5015770A (en)	1991-05-14	Process for preparing (hydrocarbylthio) aromatic amines
EP0576468B1 (fr)	1995-08-09	Procede de preparation d'amines aromatiques hydrocarbylthio
US4092369A (en)	1978-05-30	Process for the preparation of chloroalkylbenzene chlorides
EP0150587B1 (fr)	1988-02-03	Préparation de dérivés de trifluorure de chloro-toluène
JPH0351701B2 (fr)	1991-08-07
US6077973A (en)	2000-06-20	Process for the preparation of anilines which contain fluorine and new anilines which contain fluorine
EP0172612A1 (fr)	1986-02-26	Procédé de préparation d'amides aromatiques substituées par des groupes hydrocarbylthio
US6376716B1 (en)	2002-04-23	Process for the preparation of aromatic sulfur compounds
US3644515A (en)	1972-02-22	Benzenesulfonyl chloride process
US4647700A (en)	1987-03-03	Process for the preparation of meta-chloroanilines
EP0156352B1 (fr)	1988-08-03	Procédé pour la préparation de (alkylthio-, cycloalkylthio- ou arylthio)-phénols
JP2002114719A (ja)	2002-04-16	パラジクロロベンゼンの製造方法
US3071622A (en)	1963-01-01	Sulfide cleavage
US3071624A (en)	1963-01-01	aluminum o-ckesoxide catalyst
US4288628A (en)	1981-09-08	Process for the production of mono-halothiophenols and thiophenols