CA1040657A - Procede de preparation d'ethers aminophenyalkyl - Google Patents

Procede de preparation d'ethers aminophenyalkyl

Info

Publication number: CA1040657A
Authority: CA; Canada
Prior art keywords: process according; zero; salt; salts; disodium
Prior art date: 1973-10-30
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

CA212,489A

Other languages

English (en)

Other versions

CA212489S (en

Inventor

Kurt Habig

Konrad Baessler

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.)

Hoechst AG

Original Assignee

Hoechst AG

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.)

1973-10-30

Filing date

1974-10-29

Publication date

1978-10-17

1974-10-29 Application filed by Hoechst AG filed Critical Hoechst AG

1978-10-17 Application granted granted Critical

1978-10-17 Publication of CA1040657A publication Critical patent/CA1040657A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 20
150000002170 ethers Chemical class 0.000 title abstract 3
230000003197 catalytic effect Effects 0.000 claims abstract description 7
239000007864 aqueous solution Substances 0.000 claims abstract description 5
150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 4
238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 11
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
150000002828 nitro derivatives Chemical class 0.000 claims description 8
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 7
239000003054 catalyst Substances 0.000 claims description 6
229910052697 platinum Inorganic materials 0.000 claims description 5
229910052763 palladium Inorganic materials 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
150000002430 hydrocarbons Chemical class 0.000 claims description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
239000004280 Sodium formate Substances 0.000 claims description 2
GOBGCUAZYIPRTM-UHFFFAOYSA-N [Na+].[Na+].OB(O)OB([O-])[O-] Chemical compound [Na+].[Na+].OB(O)OB([O-])[O-] GOBGCUAZYIPRTM-UHFFFAOYSA-N 0.000 claims description 2
-1 aminophenyl alkylether Chemical class 0.000 claims description 2
229910021538 borax Inorganic materials 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims description 2
AJFXNBUVIBKWBT-UHFFFAOYSA-N disodium;boric acid;hydrogen borate Chemical compound [Na+].[Na+].OB(O)O.OB(O)O.OB(O)O.OB([O-])[O-] AJFXNBUVIBKWBT-UHFFFAOYSA-N 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
159000000001 potassium salts Chemical class 0.000 claims description 2
239000001632 sodium acetate Substances 0.000 claims description 2
235000017281 sodium acetate Nutrition 0.000 claims description 2
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims description 2
235000019254 sodium formate Nutrition 0.000 claims description 2
235000010339 sodium tetraborate Nutrition 0.000 claims description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims 2
239000004215 Carbon black (E152) Substances 0.000 claims 1
239000007858 starting material Substances 0.000 claims 1
239000000126 substance Substances 0.000 abstract description 6
230000000694 effects Effects 0.000 abstract description 3
150000005181 nitrobenzenes Chemical class 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
229910052759 nickel Inorganic materials 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
239000002904 solvent Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
150000007514 bases Chemical class 0.000 description 2
239000000872 buffer Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
150000003738 xylenes Chemical class 0.000 description 2
GEQNZVKIDIPGCO-UHFFFAOYSA-N 2,4-dimethoxyaniline Chemical compound COC1=CC=C(N)C(OC)=C1 GEQNZVKIDIPGCO-UHFFFAOYSA-N 0.000 description 1
HQBJSEKQNRSDAZ-UHFFFAOYSA-N 2,6-dimethoxyaniline Chemical compound COC1=CC=CC(OC)=C1N HQBJSEKQNRSDAZ-UHFFFAOYSA-N 0.000 description 1
GOJFAKBEASOYNM-UHFFFAOYSA-N 2-(2-aminophenoxy)aniline Chemical class NC1=CC=CC=C1OC1=CC=CC=C1N GOJFAKBEASOYNM-UHFFFAOYSA-N 0.000 description 1
GDTSJMKGXGJFGQ-UHFFFAOYSA-N 3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound O1B([O-])OB2OB([O-])OB1O2 GDTSJMKGXGJFGQ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000003139 buffering effect Effects 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
150000002830 nitrogen compounds Chemical class 0.000 description 1
229920001021 polysulfide Polymers 0.000 description 1
239000005077 polysulfide Substances 0.000 description 1
150000008117 polysulfides Polymers 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000047 product Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
DPUZPWAFXJXHBN-UHFFFAOYSA-N tetrasodium dioxidoboranyloxy(dioxido)borane Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]B([O-])OB([O-])[O-] DPUZPWAFXJXHBN-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA212,489A 1973-10-30 1974-10-29 Procede de preparation d'ethers aminophenyalkyl Expired CA1040657A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19732354288 DE2354288C2 (de)	1973-10-30	1973-10-30	Verfahren zur Herstellung von Aminophenylalkyläthern

Publications (1)

Publication Number	Publication Date
CA1040657A true CA1040657A (fr)	1978-10-17

Family

ID=5896833

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA212,489A Expired CA1040657A (fr)	1973-10-30	1974-10-29	Procede de preparation d'ethers aminophenyalkyl

Country Status (9)

Country	Link
JP (1)	JPS5126833A (fr)
BE (1)	BE821683R (fr)
CA (1)	CA1040657A (fr)
CH (1)	CH574392A5 (fr)
DE (1)	DE2354288C2 (fr)
FR (1)	FR2249072B1 (fr)
GB (1)	GB1493605A (fr)
IT (1)	IT1046401B (fr)
NL (1)	NL7413992A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE980216A1 (en) *	1989-04-17	2000-02-23	Scotia Holdings Plc	Anti-virals
US20030162230A1 (en)	2000-09-27	2003-08-28	Reagan Kevin J.	Method for quantifying phosphokinase activity on proteins

1973
- 1973-10-30 DE DE19732354288 patent/DE2354288C2/de not_active Expired
1974
- 1974-10-25 NL NL7413992A patent/NL7413992A/xx not_active Application Discontinuation
- 1974-10-25 CH CH1436474A patent/CH574392A5/xx not_active IP Right Cessation
- 1974-10-28 GB GB4652674A patent/GB1493605A/en not_active Expired
- 1974-10-28 IT IT2888474A patent/IT1046401B/it active
- 1974-10-29 JP JP12400674A patent/JPS5126833A/ja active Pending
- 1974-10-29 CA CA212,489A patent/CA1040657A/fr not_active Expired
- 1974-10-30 BE BE150060A patent/BE821683R/fr not_active IP Right Cessation
- 1974-10-30 FR FR7436283A patent/FR2249072B1/fr not_active Expired

Also Published As

Publication number	Publication date
CH574392A5 (fr)	1976-04-15
DE2354288B1 (de)	1975-03-20
IT1046401B (it)	1980-06-30
FR2249072B1 (fr)	1978-06-09
FR2249072A1 (fr)	1975-05-23
BE821683R (fr)	1975-04-30
DE2354288C2 (de)	1976-01-02
NL7413992A (nl)	1975-05-02
GB1493605A (en)	1977-11-30
JPS5126833A (ja)	1976-03-05

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