CH382755A - Verfahren zur Herstellung von Diazoamino-Verbindungen - Google Patents

Verfahren zur Herstellung von Diazoamino-Verbindungen

Info

Publication number: CH382755A
Authority: CH; Switzerland
Prior art keywords: sep; compounds; diazoamino; carboxylic acid; methyl
Prior art date: 1958-07-09

Application number

CH7529359A

Other languages

German (de)

English (en)

Inventor

Kurt Dr Breig

Heinz Dr Gutjahr

Original Assignee

Bayer 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.)

1958-07-09

Filing date

1959-07-02

Publication date

1964-10-15

1959-07-02 Application filed by Bayer Ag filed Critical Bayer Ag

1964-10-15 Publication of CH382755A publication Critical patent/CH382755A/de

Links

-1 diazoamino compounds Chemical class 0.000 title claims description 23
238000000034 method Methods 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
239000003086 colorant Substances 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000000547 substituted alkyl group Chemical group 0.000 claims description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
WVMBPWMAQDVZCM-UHFFFAOYSA-N N-methylanthranilic acid Chemical compound CNC1=CC=CC=C1C(O)=O WVMBPWMAQDVZCM-UHFFFAOYSA-N 0.000 description 4
230000008878 coupling Effects 0.000 description 4
238000010168 coupling process Methods 0.000 description 4
238000005859 coupling reaction Methods 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
235000002639 sodium chloride Nutrition 0.000 description 4
238000003756 stirring Methods 0.000 description 4
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical group OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
239000000203 mixture Substances 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
206010039587 Scarlet Fever Diseases 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
150000003141 primary amines Chemical class 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
230000000087 stabilizing effect Effects 0.000 description 2
150000003457 sulfones Chemical class 0.000 description 2
230000008719 thickening Effects 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
OCISOSJGBCQHHN-UHFFFAOYSA-N 3-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC(O)=CC2=C1 OCISOSJGBCQHHN-UHFFFAOYSA-N 0.000 description 1
QFUZJHWRUZVIOF-UHFFFAOYSA-N 4,5-dichloro-2-methylaniline Chemical compound CC1=CC(Cl)=C(Cl)C=C1N QFUZJHWRUZVIOF-UHFFFAOYSA-N 0.000 description 1
WRZOMWDJOLIVQP-UHFFFAOYSA-N 5-Chloro-ortho-toluidine Chemical compound CC1=CC=C(Cl)C=C1N WRZOMWDJOLIVQP-UHFFFAOYSA-N 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 1
229920000297 Rayon Polymers 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
230000008021 deposition Effects 0.000 description 1
150000008049 diazo compounds Chemical class 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
238000002156 mixing Methods 0.000 description 1
MOUVJGIRLPZEES-UHFFFAOYSA-N n-(4-chloro-2,5-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(NC(=O)CC(C)=O)=C(OC)C=C1Cl MOUVJGIRLPZEES-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000003973 paint Substances 0.000 description 1
DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
239000002964 rayon Substances 0.000 description 1
239000004627 regenerated cellulose Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000007017 scission Effects 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000000344 soap Substances 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
125000000626 sulfinic acid group Chemical group 0.000 description 1
125000001174 sulfone group Chemical group 0.000 description 1

Landscapes

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

CH7529359A 1958-07-09 1959-07-02 Verfahren zur Herstellung von Diazoamino-Verbindungen CH382755A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF0026120		1958-07-09

Publications (1)

Publication Number	Publication Date
CH382755A true CH382755A (de)	1964-10-15

Family

ID=7091896

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH7529359A CH382755A (de)	1958-07-09	1959-07-02	Verfahren zur Herstellung von Diazoamino-Verbindungen

Country Status (2)

Country	Link
BE (1)	BE580476A (fr)
CH (1)	CH382755A (fr)

1959
- 1959-07-02 CH CH7529359A patent/CH382755A/de unknown
- 1959-07-08 BE BE580476A patent/BE580476A/fr unknown

Also Published As

Publication number	Publication date
BE580476A (fr)	1959-11-03

Publication	Publication Date	Title
DE1070313B (de)	1959-12-03	Verfahren zur Herstellung von 1-Amino-4- phenylamino- anthrachinon- 2- sulfonsäuren
DE1006988C2 (de)	1957-10-03	Verfahren zur Herstellung von chromhaltigen Azofarbstoffen
CH382755A (de)	1964-10-15	Verfahren zur Herstellung von Diazoamino-Verbindungen
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AT343243B (de)	1978-05-10	Verfahren zur herstellung von benzidinpigmenten
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