CH422794A - Verfahren zur Herstellung von Additionsverbindungen - Google Patents

Verfahren zur Herstellung von Additionsverbindungen

Info

Publication number: CH422794A
Authority: CH; Switzerland
Prior art keywords: ketene; reaction; preparation; sulfoisocyanate; formula
Prior art date: 1958-11-08

Application number

CH8032359A

Other languages

German (de)

English (en)

Inventor

Roderich Dr Graf

Eberhard Dr Mundlos

Original Assignee

Hoechst Ag

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.)

1958-11-08

Filing date

1959-11-06

Publication date

1966-10-31

1959-11-06 Application filed by Hoechst Ag filed Critical Hoechst Ag

1966-10-31 Publication of CH422794A publication Critical patent/CH422794A/de

Links

150000001875 compounds Chemical class 0.000 title claims description 8
238000000034 method Methods 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title description 4
-1 hydrocarbon radical Chemical class 0.000 claims description 10
DXDUKPXLDUXKGB-UHFFFAOYSA-N sulfuroisocyanatidic acid Chemical class OS(=O)(=O)N=C=O DXDUKPXLDUXKGB-UHFFFAOYSA-N 0.000 claims description 8
150000002561 ketenes Chemical class 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical group 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 4
150000005840 aryl radicals Chemical class 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
239000000047 product Substances 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 5
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
PKCJINSDQGCYOU-UHFFFAOYSA-N S(=O)(=O)(O)N=C=O.C1=CC=CC2=CC=CC=C12 Chemical compound S(=O)(=O)(O)N=C=O.C1=CC=CC2=CC=CC=C12 PKCJINSDQGCYOU-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
ZAVAYOULWNNSDM-UHFFFAOYSA-N chloro N-(oxomethylidene)sulfamate Chemical compound ClOS(=O)(=O)N=C=O ZAVAYOULWNNSDM-UHFFFAOYSA-N 0.000 description 2
239000012043 crude product Substances 0.000 description 2
ZWJPCOALBPMBIC-UHFFFAOYSA-N diphenylketene Chemical compound C=1C=CC=CC=1C(=C=O)C1=CC=CC=C1 ZWJPCOALBPMBIC-UHFFFAOYSA-N 0.000 description 2
230000008030 elimination Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
NWXORMWIWGSYJJ-UHFFFAOYSA-N 2-ethylbut-1-en-1-one Chemical compound CCC(CC)=C=O NWXORMWIWGSYJJ-UHFFFAOYSA-N 0.000 description 1
MCJYFCRORMMYBR-UHFFFAOYSA-N 2-methylbut-1-en-1-one Chemical compound CCC(C)=C=O MCJYFCRORMMYBR-UHFFFAOYSA-N 0.000 description 1
VDOKWPVSGXHSNP-UHFFFAOYSA-N 2-methylprop-1-en-1-one Chemical compound CC(C)=C=O VDOKWPVSGXHSNP-UHFFFAOYSA-N 0.000 description 1
RZGZTQYTDRQOEY-UHFFFAOYSA-N 2-phenylethenone Chemical compound O=C=CC1=CC=CC=C1 RZGZTQYTDRQOEY-UHFFFAOYSA-N 0.000 description 1
APFRIPBQCVUZNP-UHFFFAOYSA-N 2-phenylprop-1-en-1-one Chemical compound O=C=C(C)C1=CC=CC=C1 APFRIPBQCVUZNP-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
YSJJFCFKEXSWSB-UHFFFAOYSA-N C1(=CC=CC=C1)NC(C(C(=O)O)(C1=CC=CC=C1)C1=CC=CC=C1)=O Chemical compound C1(=CC=CC=C1)NC(C(C(=O)O)(C1=CC=CC=C1)C1=CC=CC=C1)=O YSJJFCFKEXSWSB-UHFFFAOYSA-N 0.000 description 1
RDSAXXOTGAWTQO-UHFFFAOYSA-N C1=CC=CC=C1.S(=O)(=O)(O)N=C=O Chemical compound C1=CC=CC=C1.S(=O)(=O)(O)N=C=O RDSAXXOTGAWTQO-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
DLQGOQQYZRUHTC-UHFFFAOYSA-N S(=O)(=O)(O)N=C=O.C1(=CC=CC=C1)C Chemical compound S(=O)(=O)(O)N=C=O.C1(=CC=CC=C1)C DLQGOQQYZRUHTC-UHFFFAOYSA-N 0.000 description 1
GWWMVTZOQIPUFH-UHFFFAOYSA-N S(=O)(=O)(O)N=C=O.ClCC1=CC=CC2=CC=CC=C12 Chemical compound S(=O)(=O)(O)N=C=O.ClCC1=CC=CC2=CC=CC=C12 GWWMVTZOQIPUFH-UHFFFAOYSA-N 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
JSEMCPMTAXQTJN-UHFFFAOYSA-N but-1-en-1-one Chemical compound CCC=C=O JSEMCPMTAXQTJN-UHFFFAOYSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
UYLUJGRCKKSWHS-UHFFFAOYSA-N prop-1-en-1-one Chemical compound CC=C=O UYLUJGRCKKSWHS-UHFFFAOYSA-N 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1

Classifications

- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/402—Amides imides, sulfamic acids
- D06M13/438—Sulfonamides ; Sulfamic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/10—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F16/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F16/36—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by a ketonic radical
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Paper (AREA)

CH8032359A 1958-11-08 1959-11-06 Verfahren zur Herstellung von Additionsverbindungen CH422794A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF27001A DE1098515B (de)	1958-11-08	1958-11-08	Verfahren zur Herstellung von Additionsverbindungen aus Ketenen und Isocyanaten

Publications (1)

Publication Number	Publication Date
CH422794A true CH422794A (de)	1966-10-31

Family

ID=7092250

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH8032359A CH422794A (de)	1958-11-08	1959-11-06	Verfahren zur Herstellung von Additionsverbindungen

Country Status (4)

Country	Link
BE (1)	BE584473A (fr)
CH (1)	CH422794A (fr)
DE (1)	DE1098515B (fr)
GB (1)	GB939844A (fr)

1958
- 1958-11-08 DE DEF27001A patent/DE1098515B/de active Pending
1959
- 1959-11-06 CH CH8032359A patent/CH422794A/de unknown
- 1959-11-09 BE BE584473A patent/BE584473A/fr unknown
- 1959-11-09 GB GB3798659A patent/GB939844A/en not_active Expired

Also Published As

Publication number	Publication date
DE1098515B (de)	1961-02-02
BE584473A (fr)	1960-05-09
GB939844A (en)	1963-10-16

Publication	Publication Date	Title
DE1620392C3 (fr)	1980-11-06
DE1201839B (de)	1965-09-30	Verfahren zur Herstellung aliphatischer Cyansaeureester, die durch elektronen-anziehende Atome oder Gruppen substituiert sind
DE1470017C3 (de)	1973-09-27	Verfahren zur Herstellung von 1,2-Dihydrochi nolinen
DE2837341A1 (de)	1980-03-20	Verfahren zur herstellung von organischen mono- und polyisocyanaten durch thermische spaltung der hydrochloride trisubstituierter harnstoffe
CH622759A5 (fr)	1981-04-30
AT214425B (de)	1961-04-10	Verfahren zur Herstellung von N-substituierten Malonimiden und deren Polymeren
CH422794A (de)	1966-10-31	Verfahren zur Herstellung von Additionsverbindungen
DE2453365A1 (de)	1975-05-15	Verfahren zur herstellung von n-trimethylsilylacetamid
DE2854152C2 (fr)	1988-07-21
DE2336403A1 (de)	1974-03-21	Verfahren zur herstellung von isocyanaten
DE2054342A1 (de)	1972-05-10	Neue 1,2,4-Oxdiazole
CH453332A (de)	1968-06-14	Verfahren zur Herstellung von Carbaminsäureestern
AT228772B (de)	1963-08-12	Verfahren zur Herstellung von neuen basisch substituierten Malonsäuredinitrilen
DE2637580C2 (de)	1990-08-02	Verfahren zur herstellung von n-substituierten oxazolidinen
CH642617A5 (de)	1984-04-30	Verfahren zur herstellung von bromhexin.
DE1445733C (de)	1972-10-12	Verfahren zur Herstellung von Imidchloriden. Ausscheidung aus: 1179214
DE1768809C3 (de)	1976-05-26	Verfahren zur Herstellung aromatischer Isocyanate
DE3211663C2 (fr)	1990-12-13
DE1261855B (de)	1968-02-29	Verfahren zur Herstellung von reinem 2-N,N-Dimethylcarbamyl-3-methyl-pyrazolyl-(5)-N,N-dimethylcarbamat
AT234105B (de)	1964-06-10	Verfahren zur Herstellung von 4-Methyl-6-isobutenyl-pyron-(2)
DE2556039C2 (de)	1985-03-07	Verfahren zur Herstellung von N,N-Dialkylaminophenyl-chlorformiat-hydrochloriden
DE1793287B2 (de)	1976-08-26	Verfahren zur herstellung von n- substituierte n-acylcarbamidsaeurehalogeniden
AT236384B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzo-1,3-oxazin-dionen-(2,4)
CH396934A (de)	1965-08-15	Verfahren zur Herstellung basisch substituierter Malonsäuredinitrile
DE1670261A1 (de)	1971-01-28	Verfahren zur Herstellung von N-Hexahydropyrimidyl-(4)-carbamin-saeureestern