CN100519502C - 6-羟基-2-萘甲酸柱状晶体及其制备方法 - Google Patents
6-羟基-2-萘甲酸柱状晶体及其制备方法 Download PDFInfo
- Publication number
- CN100519502C CN100519502C CNB008023603A CN00802360A CN100519502C CN 100519502 C CN100519502 C CN 100519502C CN B008023603 A CNB008023603 A CN B008023603A CN 00802360 A CN00802360 A CN 00802360A CN 100519502 C CN100519502 C CN 100519502C
- Authority
- CN
- China
- Prior art keywords
- naphthoic acid
- hydroxyl
- styloid
- crystal
- aqueous medium
- 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.)
- Expired - Lifetime
Links
- 239000013078 crystal Substances 0.000 title claims abstract description 76
- 238000000034 method Methods 0.000 title abstract description 22
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- JCJUKCIXTRWAQY-UHFFFAOYSA-N 6-hydroxynaphthalene-1-carboxylic acid Chemical compound OC1=CC=C2C(C(=O)O)=CC=CC2=C1 JCJUKCIXTRWAQY-UHFFFAOYSA-N 0.000 title 1
- KAUQJMHLAFIZDU-UHFFFAOYSA-N 6-Hydroxy-2-naphthoic acid Chemical compound C1=C(O)C=CC2=CC(C(=O)O)=CC=C21 KAUQJMHLAFIZDU-UHFFFAOYSA-N 0.000 claims abstract description 66
- 238000002441 X-ray diffraction Methods 0.000 claims abstract description 27
- 239000012736 aqueous medium Substances 0.000 claims abstract description 21
- 238000001816 cooling Methods 0.000 claims abstract description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000012046 mixed solvent Substances 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- 230000005484 gravity Effects 0.000 abstract description 8
- 239000000203 mixture Substances 0.000 abstract description 7
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 17
- 230000000704 physical effect Effects 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 238000009826 distribution Methods 0.000 description 13
- 238000007670 refining Methods 0.000 description 12
- 239000002245 particle Substances 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000002994 raw material Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 2
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 2
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229950011260 betanaphthol Drugs 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000010079 rubber tapping Methods 0.000 description 2
- 239000012798 spherical particle Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
- 150000004786 2-naphthols Chemical class 0.000 description 1
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
- 238000007065 Kolbe-Schmitt synthesis reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000005260 alpha ray Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000005251 gamma ray Effects 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B7/00—Single-crystal growth from solutions using solvents which are liquid at normal temperature, e.g. aqueous solutions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
出发化合物 | 精制物 | |
6-羟基-2-萘甲酸 | >97.0 | >99.0 |
3-羟基-2-萘甲酸 | 0.83 | 0.07 |
3-羟基萘-2,7-二甲酸 | 0.26 | 0.04 |
2-羟基-1-萘甲酸 | 0.05 | 0.04 |
β—萘酚 | 0.02 | 0.00 |
Claims (6)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP236951/1999 | 1999-08-24 | ||
JP23695199 | 1999-08-24 | ||
JP236951/99 | 1999-08-24 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1335832A CN1335832A (zh) | 2002-02-13 |
CN100519502C true CN100519502C (zh) | 2009-07-29 |
Family
ID=17008185
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB008023603A Expired - Lifetime CN100519502C (zh) | 1999-08-24 | 2000-08-18 | 6-羟基-2-萘甲酸柱状晶体及其制备方法 |
Country Status (10)
Country | Link |
---|---|
US (1) | US6451109B1 (zh) |
EP (1) | EP1123914B1 (zh) |
JP (1) | JP3533386B2 (zh) |
KR (1) | KR100707752B1 (zh) |
CN (1) | CN100519502C (zh) |
AT (1) | ATE357426T1 (zh) |
CA (1) | CA2348401A1 (zh) |
DE (1) | DE60034020T2 (zh) |
TW (1) | TW527451B (zh) |
WO (1) | WO2001014307A1 (zh) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4878695B2 (ja) * | 2001-04-20 | 2012-02-15 | 上野製薬株式会社 | ナフトール誘導体の造粒物およびその製法 |
ATE556996T1 (de) * | 2001-11-30 | 2012-05-15 | Nippon Catalytic Chem Ind | ßOPTISCH AKTIVE MANDELS URE UND DEREN DERIVATE, UND VERFAHREN ZU DEREN KRISTALLISIERUNGß |
WO2011115136A1 (ja) | 2010-03-16 | 2011-09-22 | 三菱化学株式会社 | コハク酸の製造方法 |
CN102173988B (zh) * | 2011-03-25 | 2013-05-01 | 衢州英特高分子材料有限公司 | 一种6-羟基-2-萘甲酸的纯化方法 |
CN103360242A (zh) * | 2012-04-09 | 2013-10-23 | 盐城拜克化学工业有限公司 | 一种6-羟基-2-萘甲酸的制备方法 |
CN102659576A (zh) * | 2012-05-02 | 2012-09-12 | 苏州思睿屹新材料股份有限公司 | 2-羟基-6-萘甲酸的精制方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH599096A5 (zh) * | 1974-06-04 | 1978-05-12 | Hoechst Ag | |
DE3800989A1 (de) * | 1988-01-15 | 1989-07-27 | Hoechst Ag | Verfahren zur reinigung von 2-hydroxy-naphthalin-6-carbonsaeure |
JPH10120624A (ja) * | 1996-10-18 | 1998-05-12 | Sugai Kagaku Kogyo Kk | 2−ヒドロキシナフタレン−6−カルボン酸の精製方法 |
-
2000
- 2000-08-16 TW TW089116518A patent/TW527451B/zh not_active IP Right Cessation
- 2000-08-18 CA CA002348401A patent/CA2348401A1/en not_active Abandoned
- 2000-08-18 AT AT00953491T patent/ATE357426T1/de not_active IP Right Cessation
- 2000-08-18 KR KR1020017004833A patent/KR100707752B1/ko active IP Right Grant
- 2000-08-18 EP EP00953491A patent/EP1123914B1/en not_active Expired - Lifetime
- 2000-08-18 CN CNB008023603A patent/CN100519502C/zh not_active Expired - Lifetime
- 2000-08-18 US US09/830,119 patent/US6451109B1/en not_active Expired - Lifetime
- 2000-08-18 WO PCT/JP2000/005535 patent/WO2001014307A1/ja active IP Right Grant
- 2000-08-18 DE DE60034020T patent/DE60034020T2/de not_active Expired - Lifetime
- 2000-08-18 JP JP2001518400A patent/JP3533386B2/ja not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
EP1123914A1 (en) | 2001-08-16 |
JP3533386B2 (ja) | 2004-05-31 |
DE60034020D1 (de) | 2007-05-03 |
EP1123914A4 (en) | 2005-06-08 |
CA2348401A1 (en) | 2001-03-01 |
TW527451B (en) | 2003-04-11 |
EP1123914B1 (en) | 2007-03-21 |
CN1335832A (zh) | 2002-02-13 |
KR100707752B1 (ko) | 2007-04-17 |
US6451109B1 (en) | 2002-09-17 |
DE60034020T2 (de) | 2007-12-13 |
ATE357426T1 (de) | 2007-04-15 |
WO2001014307A1 (fr) | 2001-03-01 |
KR20010080213A (ko) | 2001-08-22 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
ASS | Succession or assignment of patent right |
Owner name: UENO FINE CHEMICALS INDUSTRY Free format text: FORMER OWNER: CO., LTD. UENO SCIENCE Effective date: 20080926 |
|
C41 | Transfer of patent application or patent right or utility model | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20080926 Address after: Osaka City, Osaka of Japan Applicant after: Ueno Seiyaku K. K. Address before: Osaka City, Osaka of Japan Applicant before: Ueno Technology Co., Ltd. |
|
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
EE01 | Entry into force of recordation of patent licensing contract |
Assignee: Suzhou Lintong New Material Technology Co., Ltd. Assignor: Ueno Seiyaku K. K. Contract record no.: 2011990000137 Denomination of invention: Columnar crystals of 6-hydroxy-Naphthoic acid and process for the production thereof Granted publication date: 20090729 License type: Exclusive License Open date: 20020213 Record date: 20110309 |
|
EM01 | Change of recordation of patent licensing contract |
Change date: 20120110 Contract record no.: 2011990000137 Assignee after: Suzhou 3e New Material Corporation Assignee before: Suzhou Lintong New Material Technology Co., Ltd. |
|
ASS | Succession or assignment of patent right |
Owner name: MASAYA KITAYAMA Free format text: FORMER OWNER: UENO SEIYAKU K.K. Effective date: 20140609 |
|
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20140609 Address after: Hyogo Patentee after: Kitayama Masaya Address before: Osaka City, Osaka of Japan Patentee before: Ueno Seiyaku K. K. |
|
CX01 | Expiry of patent term | ||
CX01 | Expiry of patent term |
Granted publication date: 20090729 |