JPS6212821B2 - - Google Patents

Info

Publication number: JPS6212821B2
Authority: JP; Japan
Prior art keywords: copper phthalocyanine; sulfur; chloride; highly chlorinated; solvent
Prior art date: 1979-07-02
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

JP8270379A

Other languages

English (en)

Japanese (ja)

Other versions

JPS568457A (en

Inventor

Akira Matsura

Tomio Segawa

Yukio Nomyama

Yoichi Kumada

Hideo Sawada

Ritsu Ninomya

Sakae Kuramoto

Genichi Suyama

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.)

Kawasaki Kasei Chemicals Ltd

Original Assignee

Kawasaki Kasei Chemicals Ltd

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.)

1979-07-02

Filing date

1979-07-02

Publication date

1987-03-20

1979-07-02 Application filed by Kawasaki Kasei Chemicals Ltd filed Critical Kawasaki Kasei Chemicals Ltd

1979-07-02 Priority to JP8270379A priority Critical patent/JPS568457A/ja

1981-01-28 Publication of JPS568457A publication Critical patent/JPS568457A/ja

1987-03-20 Publication of JPS6212821B2 publication Critical patent/JPS6212821B2/ja

Status Granted legal-status Critical Current

Links

RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical class [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 claims description 101
239000002904 solvent Substances 0.000 claims description 50
238000005660 chlorination reaction Methods 0.000 claims description 44
239000007795 chemical reaction product Substances 0.000 claims description 32
239000000460 chlorine Substances 0.000 claims description 32
239000007788 liquid Substances 0.000 claims description 32
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 30
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 claims description 29
239000003054 catalyst Substances 0.000 claims description 29
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 28
229910052717 sulfur Inorganic materials 0.000 claims description 28
239000011593 sulfur Substances 0.000 claims description 28
NNTJKSMVNWGFTB-UHFFFAOYSA-N disulfuryl chloride Chemical compound ClS(=O)(=O)OS(Cl)(=O)=O NNTJKSMVNWGFTB-UHFFFAOYSA-N 0.000 claims description 22
229910052801 chlorine Inorganic materials 0.000 claims description 19
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 claims description 17
238000004519 manufacturing process Methods 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 12
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 9
XOCUXOWLYLLJLV-UHFFFAOYSA-N [O].[S] Chemical compound [O].[S] XOCUXOWLYLLJLV-UHFFFAOYSA-N 0.000 claims description 7
238000000034 method Methods 0.000 description 46
235000017168 chlorine Nutrition 0.000 description 20
239000000049 pigment Substances 0.000 description 19
238000001914 filtration Methods 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
238000005406 washing Methods 0.000 description 12
239000000463 material Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
235000002639 sodium chloride Nutrition 0.000 description 8
230000007423 decrease Effects 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000004821 distillation Methods 0.000 description 6
238000000227 grinding Methods 0.000 description 6
238000002347 injection Methods 0.000 description 6
239000007924 injection Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
238000006467 substitution reaction Methods 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 5
239000007810 chemical reaction solvent Substances 0.000 description 5
125000001309 chloro group Chemical group Cl* 0.000 description 5
230000000052 comparative effect Effects 0.000 description 5
230000007797 corrosion Effects 0.000 description 5
238000005260 corrosion Methods 0.000 description 5
239000001056 green pigment Substances 0.000 description 5
239000011630 iodine Substances 0.000 description 5
229910052740 iodine Inorganic materials 0.000 description 5
239000000047 product Substances 0.000 description 5
238000000926 separation method Methods 0.000 description 5
239000003513 alkali Substances 0.000 description 4
-1 aluminum chloride-salt Chemical class 0.000 description 4
238000001035 drying Methods 0.000 description 4
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 4
229910001220 stainless steel Inorganic materials 0.000 description 4
239000010935 stainless steel Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 3
239000002994 raw material Substances 0.000 description 3
238000011084 recovery Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000003828 vacuum filtration Methods 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
150000001555 benzenes Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000005259 measurement Methods 0.000 description 2
239000007769 metal material Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
GUYIZQZWDFCUTA-UHFFFAOYSA-N (pentadecachlorophthalocyaninato(2-))-copper Chemical compound [Cu+2].N1=C([N-]2)C3=C(Cl)C(Cl)=C(Cl)C(Cl)=C3C2=NC(C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C22)=NC2=NC(C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C22)=NC2=NC2=C(C(Cl)=C(C(Cl)=C3)Cl)C3=C1[N-]2 GUYIZQZWDFCUTA-UHFFFAOYSA-N 0.000 description 1
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
DSPXASHHKFVPCL-UHFFFAOYSA-N 1-isocyanocyclohexene Chemical compound [C-]#[N+]C1=CCCCC1 DSPXASHHKFVPCL-UHFFFAOYSA-N 0.000 description 1
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 1
239000001055 blue pigment Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000012295 chemical reaction liquid Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000010949 copper Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
229960003280 cupric chloride Drugs 0.000 description 1
238000010908 decantation Methods 0.000 description 1
230000007547 defect Effects 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910000856 hastalloy Inorganic materials 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
235000021110 pickles Nutrition 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000011112 process operation Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
238000007789 sealing Methods 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000002351 wastewater Substances 0.000 description 1

Landscapes

Nitrogen Condensed Heterocyclic Rings (AREA)

JP8270379A 1979-07-02 1979-07-02 Production of highly chlorinated copper phthalocyanine Granted JPS568457A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP8270379A JPS568457A (en)	1979-07-02	1979-07-02	Production of highly chlorinated copper phthalocyanine

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP8270379A JPS568457A (en)	1979-07-02	1979-07-02	Production of highly chlorinated copper phthalocyanine

Publications (2)

Publication Number	Publication Date
JPS568457A JPS568457A (en)	1981-01-28
JPS6212821B2 true JPS6212821B2 (ko)	1987-03-20

Family

ID=13781752

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP8270379A Granted JPS568457A (en)	1979-07-02	1979-07-02	Production of highly chlorinated copper phthalocyanine

Country Status (1)

Country	Link
JP (1)	JPS568457A (ko)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP4649689B2 (ja)	1999-07-09	2011-03-16	ダイキン工業株式会社	ポリフルオロアルキルエステル類の製造方法およびこのエステルを用いる含フッ素アクリル共重合体の製造方法

1979
- 1979-07-02 JP JP8270379A patent/JPS568457A/ja active Granted

Also Published As

Publication number	Publication date
JPS568457A (en)	1981-01-28

Publication	Publication Date	Title
JPH0259819B2 (ko)	1990-12-13
US2662085A (en)	1953-12-08	Process for preparation of chlorinated copper phthalocyanine
CA1058626A (en)	1979-07-17	Manufacture of canthaxanthin
US4221734A (en)	1980-09-09	Process for the preparation of derivatives of fluoroalkane-carboxylic and perfluoroalkane-sulfinic acids
EP0009205B2 (de)	1985-07-24	Verfahren zur Herstellung von gegebenenfalls substituiertem Benzoylchlorid
EP0008548B1 (fr)	1982-06-09	Nouveau procédé de préparation du disulfure de benzothiazyle
US4218376A (en)	1980-08-19	Process for producing highly chlorinated copper phthalocyanine
JPS6212821B2 (ko)	1987-03-20
US2608591A (en)	1952-08-26	Substitution chlorination of aromatic compounds with liquid chlorine
JP2930774B2 (ja)	1999-08-03	キノフタロンの製造方法
US4067881A (en)	1978-01-10	Manufacture of polychloro-copper phthalocyanines
JPS6228820B2 (ko)	1987-06-23
KR950004889B1 (ko)	1995-05-15	1,3,6,8-데트라브로모피렌의 제조방법
US4246180A (en)	1981-01-20	Process for separating off 1-amino-4-bromoanthraquinone-2-sulphonic acid
JPS6210266B2 (ko)	1987-03-05
CA1211128A (en)	1986-09-09	Process for the manufacture of 2,6-dichloro-4- nitroaniline
JPS63196539A (ja)	1988-08-15	高純度のテトラクロロ−１，４−ベンゾキノンの製造方法
JP2730991B2 (ja)	1998-03-25	１―アミノ―２―クロル―４―ヒドロキシ―アントラキノンの製造方法
US2099781A (en)	1937-11-23	Halogenation process and product
JPS6299339A (ja)	1987-05-08	クロルアニルの製造法
US2002988A (en)	1935-05-28	Preparation of methyl-anthra-quinone
US4031116A (en)	1977-06-21	Process for preparing pure 1-nitroanthraquinone
JPH06737B2 (ja)	1994-01-05	アルキル―〔３クロロフェニル〕―スルホンの製造方法
JPS637547B2 (ko)	1988-02-17
JPS61118378A (ja)	1986-06-05	テトラクロロフタル酸無水物の製造法