JP2013502391A5 - - Google Patents
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- Publication number
- JP2013502391A5 JP2013502391A5 JP2012525122A JP2012525122A JP2013502391A5 JP 2013502391 A5 JP2013502391 A5 JP 2013502391A5 JP 2012525122 A JP2012525122 A JP 2012525122A JP 2012525122 A JP2012525122 A JP 2012525122A JP 2013502391 A5 JP2013502391 A5 JP 2013502391A5
- Authority
- JP
- Japan
- Prior art keywords
- sulfuric acid
- organic phase
- aqueous base
- reaction
- temperature
- Prior art date
- 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.)
- Withdrawn
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 239000012074 organic phase Substances 0.000 claims description 11
- 239000012454 non-polar solvent Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- CYMPUOGZUXAIMY-UHFFFAOYSA-N 4-methoxy-2-methyl-n-phenylaniline Chemical compound CC1=CC(OC)=CC=C1NC1=CC=CC=C1 CYMPUOGZUXAIMY-UHFFFAOYSA-N 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- QPNFUBAIQZJEPO-UHFFFAOYSA-N 2-[4-(dibutylamino)-2-hydroxybenzoyl]benzoic acid Chemical compound OC1=CC(N(CCCC)CCCC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O QPNFUBAIQZJEPO-UHFFFAOYSA-N 0.000 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000012467 final product Substances 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 239000002585 base Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09168288A EP2289896A1 (en) | 2009-08-20 | 2009-08-20 | Process for the manufacture of 3-dibutylamino-6-methyl-7-anilinofluoran |
| EP09168288.0 | 2009-08-20 | ||
| PCT/EP2010/061530 WO2011020726A1 (en) | 2009-08-20 | 2010-08-09 | Process for the manufacture of 3-dibutylamino-6-methyl-7-anilinofluoran |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013502391A JP2013502391A (ja) | 2013-01-24 |
| JP2013502391A5 true JP2013502391A5 (cg-RX-API-DMAC10.html) | 2013-03-14 |
Family
ID=41314566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012525122A Withdrawn JP2013502391A (ja) | 2009-08-20 | 2010-08-09 | ３−ジブチルラミノ−６−メチル−７−アニリノフルオランの製造方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20120149918A1 (cg-RX-API-DMAC10.html) |
| EP (2) | EP2289896A1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP2013502391A (cg-RX-API-DMAC10.html) |
| KR (1) | KR20120062795A (cg-RX-API-DMAC10.html) |
| CN (1) | CN102471348A (cg-RX-API-DMAC10.html) |
| WO (1) | WO2011020726A1 (cg-RX-API-DMAC10.html) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105838105B (zh) * | 2016-04-23 | 2017-12-05 | 浙江鸿盛化工有限公司 | 一步法制备黑色荧烷类热压敏染料的方法 |
| CN112010868B (zh) * | 2020-09-02 | 2021-07-27 | 华烁科技股份有限公司 | 一种制备黑色可逆热致变色染料的方法 |
| CN114349765B (zh) * | 2022-01-21 | 2023-05-16 | 内蒙古源宏精细化工有限公司 | 2-苯氨基-3-甲基-6-二丁氨基荧烷高效绿色合成的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5166350A (en) | 1989-06-10 | 1992-11-24 | Ciba-Geigy Corporation | Process for the manufacture of fluoran compounds |
| GB9827569D0 (en) | 1998-12-16 | 1999-02-10 | Ciba Geigy Ag | Heat sensitive recording material |
| WO2003035245A1 (en) | 2001-10-25 | 2003-05-01 | Ciba Specialty Chemicals Holding Inc. | Process for the preparation of microcapsules |
| JP5194526B2 (ja) * | 2007-04-06 | 2013-05-08 | コニカミノルタホールディングス株式会社 | 薄膜トランジスタの製造方法、画素アレイの製造方法 |
| CN101323619A (zh) * | 2007-06-12 | 2008-12-17 | 上海瑞年精细化工有限公司 | 荧烷类化合物的制造方法 |
-
2009
- 2009-08-20 EP EP09168288A patent/EP2289896A1/en not_active Ceased
-
2010
- 2010-08-09 KR KR1020127007031A patent/KR20120062795A/ko not_active Ceased
- 2010-08-09 US US13/391,130 patent/US20120149918A1/en not_active Abandoned
- 2010-08-09 CN CN2010800367241A patent/CN102471348A/zh active Pending
- 2010-08-09 JP JP2012525122A patent/JP2013502391A/ja not_active Withdrawn
- 2010-08-09 WO PCT/EP2010/061530 patent/WO2011020726A1/en not_active Ceased
- 2010-08-09 EP EP10742481A patent/EP2467386A1/en not_active Withdrawn