NL8303206A - Werkwijze voor de bereiding van 2-cyanomethylcyclohexanon. - Google Patents

Werkwijze voor de bereiding van 2-cyanomethylcyclohexanon. Download PDF

Info

Publication number: NL8303206A
Authority: NL; Netherlands
Prior art keywords: cyanohydrin; cyanide; process according; cyanomethylcyclohexanone; secondary amine
Prior art date: 1983-09-16

Application number

NL8303206A

Other languages

English (en)

Dutch (nl)

Original Assignee

Stamicarbon

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.)

1983-09-16

Filing date

1983-09-16

Publication date

1985-04-16

1983-09-16 Application filed by Stamicarbon filed Critical Stamicarbon

1983-09-16 Priority to NL8303206A priority Critical patent/NL8303206A/nl

1984-09-12 Priority to US06/649,653 priority patent/US4649211A/en

1984-09-14 Priority to DE8484201328T priority patent/DE3467573D1/de

1984-09-14 Priority to EP84201328A priority patent/EP0141449B1/de

1984-09-17 Priority to JP59192774A priority patent/JPS6087252A/ja

1985-04-16 Publication of NL8303206A publication Critical patent/NL8303206A/nl

Links

238000000034 method Methods 0.000 title claims description 23
NDKUZEVDMZDUGK-UHFFFAOYSA-N 2-(2-oxocyclohexyl)acetonitrile Chemical compound O=C1CCCCC1CC#N NDKUZEVDMZDUGK-UHFFFAOYSA-N 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title claims description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 19
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 13
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 13
-1 secondary amine salt Chemical class 0.000 claims description 10
238000000197 pyrolysis Methods 0.000 claims description 8
239000003880 polar aprotic solvent Substances 0.000 claims description 7
IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 claims description 5
238000009835 boiling Methods 0.000 claims description 4
XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 claims description 2
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 2
239000000243 solution Substances 0.000 claims 2
239000007864 aqueous solution Substances 0.000 claims 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims 1
239000010410 layer Substances 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
239000000539 dimer Substances 0.000 description 5
238000001030 gas--liquid chromatography Methods 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
238000004821 distillation Methods 0.000 description 4
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
VYTPDQSCOXJDJM-UHFFFAOYSA-N 2-methylidenecyclohexan-1-one Chemical compound C=C1CCCCC1=O VYTPDQSCOXJDJM-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
CJTRGWNHVKRZEB-UHFFFAOYSA-N cyclohexanone;formaldehyde Chemical compound O=C.O=C1CCCCC1 CJTRGWNHVKRZEB-UHFFFAOYSA-N 0.000 description 1
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010079 rubber tapping Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007738 vacuum evaporation Methods 0.000 description 1
239000002351 wastewater Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NL8303206A 1983-09-16 1983-09-16 Werkwijze voor de bereiding van 2-cyanomethylcyclohexanon. NL8303206A (nl)

Priority Applications (5)

Application Number	Priority Date	Filing Date	Title
NL8303206A NL8303206A (nl)	1983-09-16	1983-09-16	Werkwijze voor de bereiding van 2-cyanomethylcyclohexanon.
US06/649,653 US4649211A (en)	1983-09-16	1984-09-12	Process for the preparation of 2-cyanomethylcyclohexanone
DE8484201328T DE3467573D1 (en)	1983-09-16	1984-09-14	Process for the preparation of 2-cyanomethycyclohexanone
EP84201328A EP0141449B1 (de)	1983-09-16	1984-09-14	Verfahren zur Herstellung von 2-Cyanomethylcyclohexanon
JP59192774A JPS6087252A (ja)	1983-09-16	1984-09-17	２‐シアノメチルシクロヘキサノンの製法

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL8303206		1983-09-16
NL8303206A NL8303206A (nl)	1983-09-16	1983-09-16	Werkwijze voor de bereiding van 2-cyanomethylcyclohexanon.

Publications (1)

Publication Number	Publication Date
NL8303206A true NL8303206A (nl)	1985-04-16

Family

ID=19842415

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8303206A NL8303206A (nl)	1983-09-16	1983-09-16	Werkwijze voor de bereiding van 2-cyanomethylcyclohexanon.

Country Status (5)

Country	Link
US (1)	US4649211A (de)
EP (1)	EP0141449B1 (de)
JP (1)	JPS6087252A (de)
DE (1)	DE3467573D1 (de)
NL (1)	NL8303206A (de)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE959092C (de) *	1955-06-04	1957-02-28	Dragoco Gerberding Co Gmbh	Verfahren zur Herstellung von aliphatischen und cycloaliphatischen ª†-Ketonitrilen

1983
- 1983-09-16 NL NL8303206A patent/NL8303206A/nl not_active Application Discontinuation
1984
- 1984-09-12 US US06/649,653 patent/US4649211A/en not_active Expired - Fee Related
- 1984-09-14 EP EP84201328A patent/EP0141449B1/de not_active Expired
- 1984-09-14 DE DE8484201328T patent/DE3467573D1/de not_active Expired
- 1984-09-17 JP JP59192774A patent/JPS6087252A/ja active Pending

Also Published As

Publication number	Publication date
DE3467573D1 (en)	1987-12-23
US4649211A (en)	1987-03-10
JPS6087252A (ja)	1985-05-16
EP0141449B1 (de)	1987-11-19
EP0141449A1 (de)	1985-05-15

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Legal Events

Date	Code	Title	Description
1985-04-16	A1B	A search report has been drawn up
1986-08-18	DNT	Communications of changes of names of applicants whose applications have been laid open to public inspection	Free format text: STAMICARBON B.V. TE GELEEN
1987-05-04	BV	The patent application has lapsed