WO2004024826A2 - Procede pour produire de l'indigo de tres grande purete - Google Patents

Procede pour produire de l'indigo de tres grande purete Download PDF

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Publication number
WO2004024826A2
WO2004024826A2 PCT/EP2003/009363 EP0309363W WO2004024826A2 WO 2004024826 A2 WO2004024826 A2 WO 2004024826A2 EP 0309363 W EP0309363 W EP 0309363W WO 2004024826 A2 WO2004024826 A2 WO 2004024826A2
Authority
WO
WIPO (PCT)
Prior art keywords
indigo
leucoindigo
purity
solutions
production
Prior art date
Application number
PCT/EP2003/009363
Other languages
German (de)
English (en)
Inventor
Andreas Johann Schmidt
Wolfgang Schrott
Peter Miederer
Manfred GÄNG
Rudolf KRÜGER
Original Assignee
Dystar Textilfarben Gmbh & Co. Deutschland Kg
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.)
Filing date
Publication date
Application filed by Dystar Textilfarben Gmbh & Co. Deutschland Kg filed Critical Dystar Textilfarben Gmbh & Co. Deutschland Kg
Priority to AU2003260454A priority Critical patent/AU2003260454A1/en
Publication of WO2004024826A2 publication Critical patent/WO2004024826A2/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B7/00—Indigoid dyes
    • C09B7/02—Bis-indole indigos

Definitions

  • the invention is in the technical field of vat dyes.
  • Indigo is a vat dye that has been known for a long time and is used for dyeing textile material containing celiulose, in particular cotton cotton for blue denim articles.
  • indigo still contains impurities, for example up to 0.6% by weight of aniline and 0.4% by weight of N-methylaniline, as well as other organic impurities that one would like to remove. These impurities are firmly built into the crystal structure of the indigo and can therefore not be removed either by stirring with solvent or by steam distillation.
  • the water-insoluble indigo For dyeing, the water-insoluble indigo must first be converted into the water-soluble fiber-affine leuco form by reduction, which is then oxidized again to the water-insoluble indigo after being drawn onto the material to be colored.
  • An ecologically advantageous dyeing process is known from WO-A-94/23114, in which indigo is used in the form of the alkaline, aqueous leucoindigo solution obtained by catalytic reduction of an indigo suspension, and a drastic reduction in the wastewater pollution caused by sulfite / which occurs in the conventional dyeing processes. Allows sulfate or organic substances.
  • the invention thus relates to a process for the production of high-purity indigo, characterized in that aromatic amines, in particular aniline and N-methylaniline up to a content of ⁇ 200 ppm, are separated from leucoindigo solutions with exclusion of air.
  • aromatic amines in particular aniline and N-methylaniline up to a content of ⁇ 200 ppm
  • the leucoindigo solutions obtained in this way can be used directly for dyeing or oxidized to indigo.
  • all common methods for separating liquids are suitable.
  • Particular embodiments of the present invention relate, on the one hand, to extraction and, on the other hand, to distillation, it being possible for the distillation to be carried out with and without steam or by stripping with an inert gas.
  • a very special embodiment of the present invention relates to the separation by distillation of aromatic amines from highly concentrated leucoindigo solutions with exclusion of air at boiling temperature, high-purity leukoindigo solutions with a leukoindigo content of up to 55% by weight and A content of aromatic amines ⁇ 200 ppm are accessible.
  • the distillation can be carried out under normal pressure or reduced pressure.
  • Another very special embodiment of the present invention relates to steam distillation at normal pressure, high-purity dilute leucoindigo solutions containing aromatic amines below the detection limit being obtained
  • a very special embodiment of the present invention relates to extraction with a water-immiscible organic solvent, such as, for example, toluene, .xylenes, perchlorethylene, chlorobenzene, methylisopropyl ether, n-hexanol, 2-ethylhexanol, cyclohexane, cyclohexanone, petroleum ether of a suitable boiling range.
  • a water-immiscible organic solvent such as, for example, toluene, .xylenes, perchlorethylene, chlorobenzene, methylisopropyl ether, n-hexanol, 2-ethylhexanol, cyclohexane, cyclohexanone, petroleum ether of a suitable boiling range.
  • Aqueous solutions of leukoindigo are usually obtained by reducing an indigo suspension.
  • Dithionite, thiourea, hydroxyacetone and homologous organic reducing agents, electrochemical processes or hydrogen in combination with hydrogenation catalysts, such as Raney nickel, are suitable as reducing agents.
  • hydrogenation catalysts such as Raney nickel
  • EP 1097184 discloses highly concentrated leucoindigo solutions consisting of leukoindigo in the form of the leukoindigo salt of a mixture of at least two alkali metal hydroxides.
  • the separation process according to the invention is applied to these leucoindigo solutions, it is possible to obtain high-purity leukoindigo solutions whose leukoindigo content is up to 55% by weight, with aniline and N-methylaniline content ⁇ 200 ppm.
  • leuco indigo solutions purified by the processes according to the invention can be used directly for dyeing. They are advantageously suitable for dyeing cellulose-containing textile material, it being possible to proceed as described in WO-A-94/23114.
  • Leucoindigo solutions according to the invention can be used by oxidation for the production of high-purity indigo.
  • the leucoindigo solution thus prepared is subjected to distillation at normal pressure by passing a weak stream of nitrogen at a bath temperature of 140 ° C. to a concentration of 55% by weight of leucoindigo.
  • the leucoindigo solution prepared in this way contains ⁇ 200 ppm aniline and ⁇ 20 ppm N-methylaniline. It can be used directly for dyeing or oxidized to indigo in the conventional way.
  • the leucoindigo solution prepared according to Example 1 is stirred with 750 ml of toluene under nitrogen inertization for 1 hour at room temperature. Then the phases are separated. The aqueous phase contains the leuco indigo solution. It contains 1530 ppm aniline and 213 ppm N-methylaniline based on the indigo contained. The extraction is repeated twice, the aniline content dropping to 147 ppm, and N-methylaniline is no longer detectable
  • the leucoindigo solution prepared according to Example 1 is heated to 85 ° C. with nitrogen inerting and stripped with nitrogen for 5 hours with stirring. 1000 ml of water are distilled off. This amount is then through Fresh water replaced again. A 23% by weight leukoindigo solution with an aniline content of 113 ppm, based on leukoindigo, is obtained. N-methylaniline is no longer detectable.
  • the leucoindigo solution prepared according to Example 1 is distilled with steam for 3 hours. A 7% by weight leukoindigo solution is obtained in which neither aniline nor N-methylaniline can be detected.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)

Abstract

L'invention concerne un procédé pour produire de l'indigo de très grande pureté, ledit procédé étant caractérisé en ce que des amines aromatiques, notamment de l'aniline et de la N-méthylaniline, sont séparées de solutions de leuco-indigo dans une atmosphère sans air, pour permettre l'obtention d'une solution présentant une concentration en amine aromatique inférieure à 200 ppm, et en ce que les solutions de leuco-indigo ainsi purifiées sont oxydées en indigo ou éventuellement utilisées telles quelles pour teindre un matériau textile cellulosique puis oxydées en indigo.
PCT/EP2003/009363 2002-08-31 2003-08-23 Procede pour produire de l'indigo de tres grande purete WO2004024826A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2003260454A AU2003260454A1 (en) 2002-08-31 2003-08-23 Method for the production of high-purity indigo

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10240258.2 2002-08-31
DE10240258 2002-08-31

Publications (1)

Publication Number Publication Date
WO2004024826A2 true WO2004024826A2 (fr) 2004-03-25

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2003/009363 WO2004024826A2 (fr) 2002-08-31 2003-08-23 Procede pour produire de l'indigo de tres grande purete

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AU (1) AU2003260454A1 (fr)
WO (1) WO2004024826A2 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104897665A (zh) * 2015-06-10 2015-09-09 山东出入境检验检疫局检验检疫技术中心 染色纺织品中禁用偶氮染料的一步显色筛查法
EP3441431A1 (fr) 2017-08-11 2019-02-13 Archroma IP GmbH Procédés de fabrication de solutions de sel leucoindigo avec très faible contenu d'aniline
EP3441429A1 (fr) 2017-08-11 2019-02-13 Archroma IP GmbH Sel purifié de solutions leucoindigo aqueuse concentrée
EP3441430A1 (fr) 2017-08-11 2019-02-13 Archroma IP GmbH Solution de sel leucoindigo à très faible teneur d'aniline et son procédé de fabrication
WO2019030391A1 (fr) 2017-08-11 2019-02-14 Archroma Ip Gmbh Solution de sel de leucoindigo présentant une très faible teneur en aniline et son procédé de préparation
EP3569660A1 (fr) 2018-05-18 2019-11-20 Archroma IP GmbH Procédé et dispositif pour fabriquer des solutions de sel de leucoindigo sans aniline
EP3754053A1 (fr) 2020-05-04 2020-12-23 Lenzing Aktiengesellschaft Fibre cellulosique teinte dans la masse
WO2021102530A1 (fr) 2019-11-28 2021-06-03 Bann Química Ltda. Procédé de purification de solutions de sel de leuco-indigo faisant appel à un gaz inerte
US12024633B2 (en) 2019-11-28 2024-07-02 Bann Quimica Ltda. Process for purifying leucoindigo salt solutions using an inert gas

Cited By (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104897665A (zh) * 2015-06-10 2015-09-09 山东出入境检验检疫局检验检疫技术中心 染色纺织品中禁用偶氮染料的一步显色筛查法
CN111133057B (zh) * 2017-08-11 2022-09-13 昂高知识产权有限公司 用于制备不含苯胺的靛白盐溶液的方法和设备
JP2023014157A (ja) * 2017-08-11 2023-01-26 アルフローマ アイピー ゲゼルシャフト ミット ベシュレンクテル ハフツング アニリン不含ロイコインジゴ塩溶液を製造するための方法およびデバイス
EP3441430A1 (fr) 2017-08-11 2019-02-13 Archroma IP GmbH Solution de sel leucoindigo à très faible teneur d'aniline et son procédé de fabrication
KR102636594B1 (ko) * 2017-08-11 2024-02-13 아르크로마 아이피 게엠베하 아닐린 불포함 류코인디고 염 용액을 제조하기 위한 방법 및 디바이스
WO2019030396A1 (fr) 2017-08-11 2019-02-14 Archroma Ip Gmbh Procédés de fabrication de solutions de sel de leuco-indigo à très faible teneur en aniline
TWI755558B (zh) * 2017-08-11 2022-02-21 瑞士商亞齊羅馬Ｉｐ公司 製作極低苯胺含量之靛白溶液的方法、及對應之穩定的水性靛白溶液及製備靛藍的方法
WO2019030389A1 (fr) 2017-08-11 2019-02-14 Archroma Ip Gmbh Solutions aqueuses concentrées purifiées de sel de leucoindigo
JP7011042B2 (ja) 2017-08-11 2022-01-26 アルフローマ アイピー ゲゼルシャフト ミット ベシュレンクテル ハフツング 精製した濃縮水性ロイコインジゴ塩溶液
KR20200037853A (ko) * 2017-08-11 2020-04-09 아르크로마 아이피 게엠베하 아닐린 함량이 매우 낮은 류코인디고 염 용액 및 이의 제조 방법
KR20200040279A (ko) * 2017-08-11 2020-04-17 아르크로마 아이피 게엠베하 아닐린 불포함 류코인디고 염 용액을 제조하기 위한 방법 및 디바이스
CN111065690A (zh) * 2017-08-11 2020-04-24 昂高知识产权有限公司 纯化的浓靛白盐水溶液
CN111094460A (zh) * 2017-08-11 2020-05-01 昂高知识产权有限公司 制备具有很低苯胺含量的靛白盐溶液的方法
CN111108156A (zh) * 2017-08-11 2020-05-05 昂高知识产权有限公司 具有很低苯胺含量的靛白盐溶液及其制备方法
CN111133057A (zh) * 2017-08-11 2020-05-08 昂高知识产权有限公司 用于制备不含苯胺的靛白盐溶液的方法和设备
JP2020530518A (ja) * 2017-08-11 2020-10-22 アルフローマ アイピー ゲゼルシャフト ミット ベシュレンクテル ハフツング 非常に低いアニリン含有量を有するロイコインジゴ塩溶液を製造する方法
JP2020530516A (ja) * 2017-08-11 2020-10-22 アルフローマ アイピー ゲゼルシャフト ミット ベシュレンクテル ハフツング 非常に低いアニリン含有量を有するロイコインジゴ塩溶液とその製造方法
JP2020530517A (ja) * 2017-08-11 2020-10-22 アルフローマ アイピー ゲゼルシャフト ミット ベシュレンクテル ハフツング アニリン不含ロイコインジゴ塩溶液を製造するための方法およびデバイス
KR102636591B1 (ko) * 2017-08-11 2024-02-13 아르크로마 아이피 게엠베하 아닐린 함량이 매우 낮은 류코인디고 염 용액 및 이의 제조 방법
JP2020537700A (ja) * 2017-08-11 2020-12-24 アルフローマ アイピー ゲゼルシャフト ミット ベシュレンクテル ハフツング 精製した濃縮水性ロイコインジゴ塩溶液
JP7295844B2 (ja) 2017-08-11 2023-06-21 アルフローマ アイピー ゲゼルシャフト ミット ベシュレンクテル ハフツング 非常に低いアニリン含有量を有するロイコインジゴ塩溶液とその製造方法
WO2019030391A1 (fr) 2017-08-11 2019-02-14 Archroma Ip Gmbh Solution de sel de leucoindigo présentant une très faible teneur en aniline et son procédé de préparation
JP7250762B2 (ja) 2017-08-11 2023-04-03 アルフローマ アイピー ゲゼルシャフト ミット ベシュレンクテル ハフツング 非常に低いアニリン含有量を有するロイコインジゴ塩溶液を製造する方法
WO2019030397A1 (fr) 2017-08-11 2019-02-14 Archroma Ip Gmbh Procédé et dispositif de préparation de solutions de sel de leucoindigo exemptes d'aniline
TWI760544B (zh) * 2017-08-11 2022-04-11 瑞士商亞齊羅馬Ｉｐ公司 極低苯胺含量之靛白溶液及其製備方法及對應之製備靛藍的方法
US11299633B2 (en) 2017-08-11 2022-04-12 Archroma Ip Gmbh Leucoindigo salt solution with very low content of aniline and method of making same
TWI763903B (zh) * 2017-08-11 2022-05-11 瑞士商亞齊羅馬Ｉｐ公司 製備無苯胺之靛白溶液的方法以及製得之穩定的水性靛白溶液、製備靛藍之方法、整合設備和一裝置之用途
CN111065690B (zh) * 2017-08-11 2022-06-28 昂高知识产权有限公司 纯化的浓靛白盐水溶液
US11384245B2 (en) 2017-08-11 2022-07-12 Archroma Ip Gmbh Purified concentrated aqueous leucoindigo salt solutions
JP7245227B2 (ja) 2017-08-11 2023-03-23 アルフローマ アイピー ゲゼルシャフト ミット ベシュレンクテル ハフツング アニリン不含ロイコインジゴ塩溶液を製造するための方法およびデバイス
EP3441431A1 (fr) 2017-08-11 2019-02-13 Archroma IP GmbH Procédés de fabrication de solutions de sel leucoindigo avec très faible contenu d'aniline
CN115627081A (zh) * 2017-08-11 2023-01-20 昂高知识产权有限公司 用于制备不含苯胺的靛白盐溶液的方法和设备
EP3441429A1 (fr) 2017-08-11 2019-02-13 Archroma IP GmbH Sel purifié de solutions leucoindigo aqueuse concentrée
EP3569660A1 (fr) 2018-05-18 2019-11-20 Archroma IP GmbH Procédé et dispositif pour fabriquer des solutions de sel de leucoindigo sans aniline
CN114787290A (zh) * 2019-11-28 2022-07-22 班恩化工公司 使用惰性气体纯化靛白盐溶液的方法
US20230123640A1 (en) * 2019-11-28 2023-04-20 Bann Química Ltda. Process for purifying leucoindigo salt solutions using an inert gas
WO2021102530A1 (fr) 2019-11-28 2021-06-03 Bann Química Ltda. Procédé de purification de solutions de sel de leuco-indigo faisant appel à un gaz inerte
CN114787290B (zh) * 2019-11-28 2024-04-05 班恩化工公司 纯化靛白盐溶液的方法与惰性气体的用途
EP4067440A4 (fr) * 2019-11-28 2024-05-22 Bann Química Ltda. Procédé de purification de solutions de sel de leuco-indigo faisant appel à un gaz inerte
US12024633B2 (en) 2019-11-28 2024-07-02 Bann Quimica Ltda. Process for purifying leucoindigo salt solutions using an inert gas
EP3754053A1 (fr) 2020-05-04 2020-12-23 Lenzing Aktiengesellschaft Fibre cellulosique teinte dans la masse
WO2021224112A1 (fr) 2020-05-04 2021-11-11 Lenzing Aktiengesellschaft Fibre cellulosique teinte dans la masse

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