CH426773A - Verfahren zur Herstellung von Imidochloriden und/oder salzsauren Salzen von Imidochloriden - Google Patents

Verfahren zur Herstellung von Imidochloriden und/oder salzsauren Salzen von Imidochloriden

Info

Publication number: CH426773A
Authority: CH; Switzerland
Prior art keywords: reaction; phosgene; bonded; imidochlorides; temperature
Prior art date: 1960-10-31

Application number

CH1253561A

Other languages

German (de)

English (en)

Inventor

Hubertus Ottenheym Johannes

Willem Garritsen Johan

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.)

1960-10-31

Filing date

1961-10-30

Publication date

1966-12-31

1961-10-30 Application filed by Stamicarbon filed Critical Stamicarbon

1966-12-31 Publication of CH426773A publication Critical patent/CH426773A/de

Links

238000000034 method Methods 0.000 title claims description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims description 20
238000004519 manufacturing process Methods 0.000 title claims description 4
238000006243 chemical reaction Methods 0.000 claims description 70
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 46
150000001408 amides Chemical class 0.000 claims description 30
239000011541 reaction mixture Substances 0.000 claims description 18
125000003118 aryl group Chemical group 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 13
125000002877 alkyl aryl group Chemical group 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
150000001721 carbon Chemical group 0.000 claims description 10
125000005521 carbonamide group Chemical group 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 7
125000003710 aryl alkyl group Chemical group 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
239000007795 chemical reaction product Substances 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
239000000470 constituent Substances 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 54
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
239000000126 substance Substances 0.000 description 18
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 14
238000004566 IR spectroscopy Methods 0.000 description 11
239000007788 liquid Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
238000000921 elemental analysis Methods 0.000 description 7
239000000047 product Substances 0.000 description 7
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 6
-1 PC15 Chemical class 0.000 description 6
238000004821 distillation Methods 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 4
150000001409 amidines Chemical class 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
150000001805 chlorine compounds Chemical class 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229960001413 acetanilide Drugs 0.000 description 3
230000007717 exclusion Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000007787 solid Substances 0.000 description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
YUMCRXLLWKQDJY-UHFFFAOYSA-N n-propylpropanamide Chemical compound CCCNC(=O)CC YUMCRXLLWKQDJY-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
NTLKAXQBFYZMAH-UHFFFAOYSA-N 2-methylpentanamide Chemical compound CCCC(C)C(N)=O NTLKAXQBFYZMAH-UHFFFAOYSA-N 0.000 description 1
LHNFFCJQGALMQI-UHFFFAOYSA-N 7-chloro-3,4,5,6-tetrahydro-2h-azepine Chemical compound ClC1=NCCCCC1 LHNFFCJQGALMQI-UHFFFAOYSA-N 0.000 description 1
CCJYKQOINYXBTG-UHFFFAOYSA-N C(CCC)NC(C(C)(C)C)=O.C(CCC)NC(C(C)(C)C)=O Chemical compound C(CCC)NC(C(C)(C)C)=O.C(CCC)NC(C(C)(C)C)=O CCJYKQOINYXBTG-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
101100520660 Drosophila melanogaster Poc1 gene Proteins 0.000 description 1
DYZWXBMTHNHXML-UHFFFAOYSA-N N-propylbenzamide Chemical compound CCCNC(=O)C1=CC=CC=C1 DYZWXBMTHNHXML-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
101100520662 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) PBA1 gene Proteins 0.000 description 1
GJMMXPXHXFHBPK-UHFFFAOYSA-N [P].[Cl] Chemical class [P].[Cl] GJMMXPXHXFHBPK-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000008043 acidic salts Chemical class 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
239000000975 dye Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
229940047889 isobutyramide Drugs 0.000 description 1
239000000463 material Substances 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
239000000203 mixture Substances 0.000 description 1
JSKYQRAQUAQJSW-UHFFFAOYSA-N n-butyl-2,2-dimethylpropanamide Chemical compound CCCCNC(=O)C(C)(C)C JSKYQRAQUAQJSW-UHFFFAOYSA-N 0.000 description 1
XQZDWKBCGAJXLC-UHFFFAOYSA-N n-butylpropanamide Chemical compound CCCCNC(=O)CC XQZDWKBCGAJXLC-UHFFFAOYSA-N 0.000 description 1
NCCHARWOCKOHIH-UHFFFAOYSA-N n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1 NCCHARWOCKOHIH-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

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

CH1253561A 1960-10-31 1961-10-30 Verfahren zur Herstellung von Imidochloriden und/oder salzsauren Salzen von Imidochloriden CH426773A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL257447		1960-10-31
NL257446		1960-10-31

Publications (1)

Publication Number	Publication Date
CH426773A true CH426773A (de)	1966-12-31

Family

ID=26641742

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1253561A CH426773A (de)	1960-10-31	1961-10-30	Verfahren zur Herstellung von Imidochloriden und/oder salzsauren Salzen von Imidochloriden

Country Status (2)

Country	Link
BE (1)	BE609822A (fr)
CH (1)	CH426773A (fr)

1961
- 1961-10-30 CH CH1253561A patent/CH426773A/de unknown
- 1961-10-31 BE BE609822A patent/BE609822A/fr unknown

Also Published As

Publication number	Publication date
BE609822A (fr)	1962-04-30

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DE1620392B2 (de)	1980-02-28	Polynitrilsulfite, Verfahren zu ihrer Herstellung und deren Verwendung zur Herstellung von Polyisocyanaten
DE1001980B (de)	1957-02-07	Verfahren zur Herstellung von 2, 2-Bis-(p-carboxyphenyl)-propan sowie dessen Dimethylester
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CH426773A (de)	1966-12-31	Verfahren zur Herstellung von Imidochloriden und/oder salzsauren Salzen von Imidochloriden
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