US1580709A - The-main - Google Patents
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- Publication number
- US1580709A US1580709A US1580709DA US1580709A US 1580709 A US1580709 A US 1580709A US 1580709D A US1580709D A US 1580709DA US 1580709 A US1580709 A US 1580709A
- Authority
- US
- United States
- Prior art keywords
- soluble
- acetoacetyl
- alcohol
- ether
- acetic acid
- Prior art date
- 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 - Lifetime
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 229960000583 Acetic Acid Drugs 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 12
- -1 acetoacetic acid ester Chemical class 0.000 description 10
- 239000002253 acid Substances 0.000 description 8
- 125000004432 carbon atoms Chemical group C* 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- HONMCSLFRKBQHG-UHFFFAOYSA-N 1,3-diamino-1,3-diphenylurea Chemical compound C=1C=CC=CC=1N(N)C(=O)N(N)C1=CC=CC=C1 HONMCSLFRKBQHG-UHFFFAOYSA-N 0.000 description 4
- OECJQXJWIDVMHA-UHFFFAOYSA-N C(CC(=O)C)(=O)C=1C(=C(C=CC1N)N=NC1=CC=C(C=C1)N)C(CC(=O)C)=O Chemical compound C(CC(=O)C)(=O)C=1C(=C(C=CC1N)N=NC1=CC=C(C=C1)N)C(CC(=O)C)=O OECJQXJWIDVMHA-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- OOTIEPZZGQFJME-UHFFFAOYSA-N NN(C1=C(C=CC=C1)N)C(C1=CC=CC=C1)=O Chemical compound NN(C1=C(C=CC=C1)N)C(C1=CC=CC=C1)=O OOTIEPZZGQFJME-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N Nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000875 corresponding Effects 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- YHYKLKNNBYLTQY-UHFFFAOYSA-N 1,1-diphenylhydrazine Chemical compound C=1C=CC=CC=1N(N)C1=CC=CC=C1 YHYKLKNNBYLTQY-UHFFFAOYSA-N 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4,4'-Oxydianiline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- KQIKKETXZQDHGE-UHFFFAOYSA-N 4-[(4-aminophenyl)diazenyl]aniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C(N)C=C1 KQIKKETXZQDHGE-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N Benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 102000004726 Connectin Human genes 0.000 description 2
- 108010002947 Connectin Proteins 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000004429 atoms Chemical group 0.000 description 2
- GAUZCKBSTZFWCT-UHFFFAOYSA-N azoxybenzene Chemical compound C=1C=CC=CC=1[N+]([O-])=NC1=CC=CC=C1 GAUZCKBSTZFWCT-UHFFFAOYSA-N 0.000 description 2
- XEPQAISLFOVRTP-UHFFFAOYSA-N bis(2-methylphenyl)methanediamine Chemical compound CC1=CC=CC=C1C(N)(N)C1=CC=CC=C1C XEPQAISLFOVRTP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229950005499 carbon tetrachloride Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002168 ethanoic acid esters Chemical class 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000000630 rising Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0815—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by -C(=O)-
Definitions
- R and Rf represent the same or difierent aryl residues
- Y any radicle of the hydrocarbon series containing at least one and not more than six carbon atoms
- X a connecting link of the character explained hereinafter.
- the vprocess of pounds consists in heating acylacetic acid making the com-- Application filed May 15,1923. Serial No. 639,214.
- esters such as acetoacetic acid ester or its homologues or analogues, with the corresponding diamins, such as e. g. thioanilin, dlaminodiphen lether, diaminoditolylmethan, diamino enzophenon, diaminodiphenylamm, aminobenzoylphenylenediamin, diaminoazobenzene, diammoazoxybenzene, diaminodiphenylurea, aminophenolethylene ether and others, preferably in a solvent or diluent.
- diamins such as e. g. thioanilin, dlaminodiphen lether, diaminoditolylmethan, diamino enzophenon, diaminodiphenylamm, aminobenzoylphenylenediamin, diaminoazobenzene, diammoazoxybenzene, diaminodiphen
- the new di-acylacetyl-diamino compounds may be used as primary products for the production of dyestuffs.
- the producti-obtainedin this example has ti" formula I cm.co.cm.oo.mz mmO-Nmooomcocm aryl residues, Z enact a group of connecting
- This product is one of a group corresponding to the general formula .l
- acetoacetic acid ester its analogues such as e. g. benzoylacetic acid ester, can be used for the process, as diamins e. g. thioanilin, diaminodiphenylether, di-
- aminodiphenylamin diaminodiphenylurea, aminobenzoylphenylenediamin and others are available.
- Di-acetoacetyl-4.4'-dlami- Yellow needles Dilute acetic acid: 233-234 under decom- Soluble in glacial acetic acid, nitronoazobenzene. position. benzene and pyridine, a little soluble in ether and toluene.
- Di acetoacetyl-4AJ-diaminoazoxybenzene has the formula CHa.C0.0Hg-CO.NH
- Di acetoacetylixl'-diamino-diphenylurea has the formula cmooomoonnOma.oomONHooomoooHi 2.
- R and R meaning the same or different aryl residues
- R and R meaning the same or different aryl residues
- Z one of a cup of connecting links, comprising --N" containing two N-atoms
- Y any radicle of the hy rocarbon series containing at least one and not more than six carbon atoms.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Patented Apr. 13, 1926.
UNITED STATES 1.580.1 9 PATENT. OFFICE.
ARTHUR ZITSOHER AN D ROBERT SOHMITT, OF OFFENBACH-OE-THE-MAIN, GERMANY,
ASSIGNORS TO OHEMISCHE FABRIK GRIESHEIM- ELEKTRON, OF FRANKFORT-ON- THE-MAIN GERMANY, A CORPORATION.
DI-AOYLAGETYL-DLAMINO COMPOUNDS OF THE ABOMATIG SERIES AND PROCESS OF MAKING SAME.
No Drawing.
wherein R and Rf represent the same or difierent aryl residues, Y any radicle of the hydrocarbon series containing at least one and not more than six carbon atoms, X a connecting link of the character explained hereinafter.
. Under the definition givenfor Y we include aliphatic as well as aromatic radicles, un-
derthe term connectin link for Xatoms and atom complexes suc as O, S, CH GOJ'T, 'NH1 "'a N' 2 N- NH- CHr-O- 1i- O NH-"(iH -AF and the like, which in our present invention form a. connection between the two aryl residues, as indicated by the general formula given above. The vprocess of pounds consists in heating acylacetic acid making the com-- Application filed May 15,1923. Serial No. 639,214.
esters, such as acetoacetic acid ester or its homologues or analogues, with the corresponding diamins, such as e. g. thioanilin, dlaminodiphen lether, diaminoditolylmethan, diamino enzophenon, diaminodiphenylamm, aminobenzoylphenylenediamin, diaminoazobenzene, diammoazoxybenzene, diaminodiphenylurea, aminophenolethylene ether and others, preferably in a solvent or diluent. i
The new di-acylacetyl-diamino compounds may be used as primary products for the production of dyestuffs.
The following examples illustrate the invention, the parts being byweight, and all temperatures in centigrade degrees.
' Ewample 1.
' Into a. mixture, heated to 175-180, of 205 parts of acetoacetic acid ester and 200 parts of mtrobenzene 76 parts of 4.4'-diaminobenzophenon are poured while stirring. The mixture is held at 170-180, until the reaction is finished. The pulp of crystals,
formed after cooling down, is filtered, freed of nitrobenzene by means of ether and dried.- Thedi-acetoacetyl-4.4-diaminobenzophenon,
obtained in a yleld of 68 p. 01,01 the theoreticalyield, is crystallized from much waterin colorless lustrous needles, melting at 175-176 C. (not corrected) with a feeble decomposition. The formula of this product is mcoomcoJiaOc -ONmco.cmoocrt,
acetic acid ester',g-kept-'boiling, 'until the. splitting off of alcohol is finished, and the product of the reaction is worked up in the usual manner. 116 parts of di-acetoacetyl- 4.4'-diaminoazobenzene, that, is 76 c.-of the theoretical yield, are obtained. rystallized from dilute acetic acid it forms an orange-yellow crystalline powder, decompos- .ing at 233-234 (not corrected). The producti-obtainedin this example has ti" formula I cm.co.cm.oo.mz mmO-Nmooomcocm aryl residues, Z enact a group of connecting This product is one of a group corresponding to the general formula .l
where R and R meanthe same or dilferent links comprising N=N O l| I and Y any radicle of the hydrocarbon series containing at least one and not more than six carbon atoms.
Instead of the acetoacetic acid ester its analogues such as e. g. benzoylacetic acid ester, can be used for the process, as diamins e. g. thioanilin, diaminodiphenylether, di-
aminodiphenylamin, diaminodiphenylurea, aminobenzoylphenylenediamin and others are available.
The following table gives the properties of some of the compounds obtainable according to the present process:
Dl-acylaoetyl-. Crystalized Melting point C.
compound. Aspect from. not corrected. Solubmty' Di-acetoacetyl -4.4'-diami- Fine, colorless little Acetic acid 138-139f under decom- Soluble in alcohol and glacial acetic no -3.3- dichlorodiplienylcrystals. position. acid, insoluble in ether.
methan. Dl-acetoacetyl-Lfldiamino- Colorless clin gin g Alcohol 143-144 under dccom- Soluble in alcohol and nitrobcnzene, 3.3'-ditolylmethan. needles. position. insoluble in carbontetrachloride. Di-acetoacetyl-4.4-diamino- Colorless ln s t r o u 5 Much water 175-176 under feeble Wall soluble in alcohol and glacial acetic benzophenon. needles. decomposition. gglld, a little soluble in ether and uene. Di-acetoacetyl-4.4'-dlami- Yellow needles Dilute acetic acid: 233-234 under decom- Soluble in glacial acetic acid, nitronoazobenzene. position. benzene and pyridine, a little soluble in ether and toluene. Dl-aoetoacetyl-4.4-dlamino- Brownish yellow crys- Dilute acetic acid. 219-220 under decom- Soluble in alcohol and glacial acetic azoxybenzene. talline powder. position. acid insoluble in ether. Di-acetoacctyl-4.4-diami- Clearly yellow pow- Alcohol. 215 under decompo- Soluble in alcohol and glacial acetic no-3.3-a zotoluene. der. sltlon. acid, insoluble in ether. I Di-ncetoacetyl-4.4'-diainino- Colorless lustrous leaf- Acetic acid Over 320 Soluble in lacial acetic acid and diphenlym'ea. lets. pyridine, scarcely soluble in acetone,
alcohol and xylene.
The formulas of several of the products specified above are as follows: The formula of di-acetoacetyl-i.4-diamino-3.3-dichlorodiphenylmethane is omooomoounOwn NH.CO.CH,.CO.CH;
Di acetoacetyl-4AJ-diaminoazoxybenzene has the formula CHa.C0.0Hg-CO.NH
Di acetoacetylixl'-diamino-diphenylurea has the formula cmooomoonnOma.oomONHooomoooHi 2. As new articles the di-acylacetyl-diaminocompounds of the general formula:
R and R meaning the same or different aryl residues, X one of a group of connecting links com rising -O, -s-- CH,, -oo H -NH.oo-,-i-I=N-,
and Y any radicle of the hydrocarbon series containing at least one and not more than six carbon atoms.
3. As new articles the di-acylacetyl-diaminocompounds of the general formula:
R and R meaning the same or different aryl residues, Z one of a cup of connecting links, comprising --N" containing two N-atoms, and Y any radicle of the hy rocarbon series containing at least one and not more than six carbon atoms.
4. As a new article di-acetoacetyl-diaminoazobenzene of the formula:
In testimony, that we claim the foregoing as our invention, We have signed our names, this 28th day of April 1923.
ARTHUR ZITSCHER. [1,. 8.] ROBERT SGHMITT. [ns]
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1580709A true US1580709A (en) | 1926-04-13 |
Family
ID=3410258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US1580709D Expired - Lifetime US1580709A (en) | The-main |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1580709A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4568752A (en) * | 1978-06-20 | 1986-02-04 | Ciba-Geigy Ag | Recording material for color photography |
| JP6172693B1 (en) * | 2016-09-06 | 2017-08-02 | 小西化学工業株式会社 | Method for producing azo compound |
-
0
- US US1580709D patent/US1580709A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4568752A (en) * | 1978-06-20 | 1986-02-04 | Ciba-Geigy Ag | Recording material for color photography |
| JP6172693B1 (en) * | 2016-09-06 | 2017-08-02 | 小西化学工業株式会社 | Method for producing azo compound |
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