JPS61200955A - テトラフルオロフタロニトリルの製造方法 - Google Patents

テトラフルオロフタロニトリルの製造方法

Info

Publication number: JPS61200955A
Authority: JP; Japan
Prior art keywords: benzonitrile; fraction; reaction; tetrafluorophthalonitrile; halogen exchange
Prior art date: 1985-03-01
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.): Granted

Application number

JP3881785A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0149346B2 (fr

Inventor

Osamu Kaieda

修海江田

Masaru Awashima

粟嶋　優

Koitsu Hirota

広田　幸逸

Tomoaki Nakamura

智明中村

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.)

Nippon Shokubai Co Ltd

Original Assignee

Nippon Shokubai Co 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.)

1985-03-01

Filing date

1985-03-01

Publication date

1986-09-05

1985-03-01 Application filed by Nippon Shokubai Co Ltd filed Critical Nippon Shokubai Co Ltd

1985-03-01 Priority to JP3881785A priority Critical patent/JPS61200955A/ja

1986-09-05 Publication of JPS61200955A publication Critical patent/JPS61200955A/ja

1989-10-24 Publication of JPH0149346B2 publication Critical patent/JPH0149346B2/ja

Status Granted legal-status Critical Current

Links

OFLRJMBSWDXSPG-UHFFFAOYSA-N 3,4,5,6-tetrafluorobenzene-1,2-dicarbonitrile Chemical compound FC1=C(F)C(F)=C(C#N)C(C#N)=C1F OFLRJMBSWDXSPG-UHFFFAOYSA-N 0.000 title claims description 14
238000004519 manufacturing process Methods 0.000 title claims description 6
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims abstract description 126
238000006243 chemical reaction Methods 0.000 claims abstract description 43
229910052736 halogen Inorganic materials 0.000 claims abstract description 18
150000002367 halogens Chemical class 0.000 claims abstract description 18
239000007788 liquid Substances 0.000 claims abstract description 12
239000007787 solid Substances 0.000 claims abstract description 7
OQHXZZGZASQSOB-UHFFFAOYSA-N 3,4,5,6-tetrachlorobenzene-1,2-dicarbonitrile Chemical compound ClC1=C(Cl)C(Cl)=C(C#N)C(C#N)=C1Cl OQHXZZGZASQSOB-UHFFFAOYSA-N 0.000 claims abstract description 4
238000004821 distillation Methods 0.000 claims description 21
238000000034 method Methods 0.000 claims description 20
239000012025 fluorinating agent Substances 0.000 claims description 11
239000007795 chemical reaction product Substances 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
239000000047 product Substances 0.000 claims description 7
229910001515 alkali metal fluoride Inorganic materials 0.000 claims description 3
229910001618 alkaline earth metal fluoride Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 2
238000004064 recycling Methods 0.000 claims description 2
150000002825 nitriles Chemical class 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 5
239000003153 chemical reaction reagent Substances 0.000 abstract 2
239000011541 reaction mixture Substances 0.000 abstract 2
239000000543 intermediate Substances 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 8
239000002994 raw material Substances 0.000 description 7
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
229910052700 potassium Inorganic materials 0.000 description 6
239000011591 potassium Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 5
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
239000003444 phase transfer catalyst Substances 0.000 description 4
235000003270 potassium fluoride Nutrition 0.000 description 4
239000011698 potassium fluoride Substances 0.000 description 4
239000006227 byproduct Substances 0.000 description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
238000006053 organic reaction Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
BMZDKPHJLPMINH-UHFFFAOYSA-N 3-chloro-4,5,6-trifluorobenzene-1,2-dicarbonitrile Chemical compound FC1=C(F)C(Cl)=C(C#N)C(C#N)=C1F BMZDKPHJLPMINH-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
229910001873 dinitrogen Inorganic materials 0.000 description 2
239000000203 mixture Substances 0.000 description 2
235000011164 potassium chloride Nutrition 0.000 description 2
239000001103 potassium chloride Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
239000013076 target substance Substances 0.000 description 2
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
UEMTWYSCHIRTMO-UHFFFAOYSA-N 4-chloro-3,5,6-trifluorobenzene-1,2-dicarbonitrile Chemical compound FC1=C(F)C(C#N)=C(C#N)C(F)=C1Cl UEMTWYSCHIRTMO-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
GUNJVIDCYZYFGV-UHFFFAOYSA-K antimony trifluoride Chemical compound F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 1
OYLGJCQECKOTOL-UHFFFAOYSA-L barium fluoride Chemical compound [F-].[F-].[Ba+2] OYLGJCQECKOTOL-UHFFFAOYSA-L 0.000 description 1
229910001632 barium fluoride Inorganic materials 0.000 description 1
WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
229910001634 calcium fluoride Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000001944 continuous distillation Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical class O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
150000004673 fluoride salts Chemical class 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
229920006391 phthalonitrile polymer Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000004904 shortening Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000013024 sodium fluoride Nutrition 0.000 description 1
239000011775 sodium fluoride Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
229910021561 transition metal fluoride Inorganic materials 0.000 description 1

Landscapes

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

JP3881785A 1985-03-01 1985-03-01 テトラフルオロフタロニトリルの製造方法 Granted JPS61200955A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP3881785A JPS61200955A (ja)	1985-03-01	1985-03-01	テトラフルオロフタロニトリルの製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP3881785A JPS61200955A (ja)	1985-03-01	1985-03-01	テトラフルオロフタロニトリルの製造方法

Publications (2)

Publication Number	Publication Date
JPS61200955A true JPS61200955A (ja)	1986-09-05
JPH0149346B2 JPH0149346B2 (fr)	1989-10-24

Family

ID=12535816

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP3881785A Granted JPS61200955A (ja)	1985-03-01	1985-03-01	テトラフルオロフタロニトリルの製造方法

Country Status (1)

Country	Link
JP (1)	JPS61200955A (fr)

1985
- 1985-03-01 JP JP3881785A patent/JPS61200955A/ja active Granted

Also Published As

Publication number	Publication date
JPH0149346B2 (fr)	1989-10-24

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Legal Events

Date	Code	Title	Description
2003-10-24	LAPS	Cancellation because of no payment of annual fees