US938132A - Guaiacol carbonate sulfo-acid derivative. - Google Patents
Guaiacol carbonate sulfo-acid derivative. Download PDFInfo
- Publication number
- US938132A US938132A US43984208A US1908439842A US938132A US 938132 A US938132 A US 938132A US 43984208 A US43984208 A US 43984208A US 1908439842 A US1908439842 A US 1908439842A US 938132 A US938132 A US 938132A
- Authority
- US
- United States
- Prior art keywords
- sulfo
- guaiacol
- acid
- carbonate
- salt
- 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
- 239000002253 acid Substances 0.000 title description 27
- ORUJFMPWKPVXLZ-UHFFFAOYSA-N guaiacol carbonate Chemical compound COC1=CC=CC=C1OC(=O)OC1=CC=CC=C1OC ORUJFMPWKPVXLZ-UHFFFAOYSA-N 0.000 title description 11
- 229950010370 guaiacol carbonate Drugs 0.000 title description 11
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 20
- 150000003839 salts Chemical class 0.000 description 20
- 229960001867 guaiacol Drugs 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 10
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000003513 alkali Substances 0.000 description 8
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 8
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 8
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- LULCPJWUGUVEFU-UHFFFAOYSA-N Phthiocol Natural products C1=CC=C2C(=O)C(C)=C(O)C(=O)C2=C1 LULCPJWUGUVEFU-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003518 caustics Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- 229960004889 salicylic acid Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- -1 aliphatic creosote ester Chemical class 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- HJEINPVZRDJRBY-UHFFFAOYSA-N Disul Chemical compound OS(=O)(=O)OCCOC1=CC=C(Cl)C=C1Cl HJEINPVZRDJRBY-UHFFFAOYSA-N 0.000 description 1
- 235000006173 Larrea tridentata Nutrition 0.000 description 1
- 244000073231 Larrea tridentata Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229960002126 creosote Drugs 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
Definitions
- the objects of the invention are to obtain .such salts of this character as are adapted .for therapeutic purposes, and which can be used together Withferric preparations with-- out inconvenience, producing no color reactions with them as is the case with guaiacol sulfo-acidsalts, and which, moreover, are more pleasant to the taste than the latter.
- Salts of the sulfo acids of guaiacol carbonate have heretofore remained unknown.
- salts of the sulfo acids of the aliphatic creosote ester are described. These, howeven'are in no way uniforn'i. and are most probably Sincethey give a color reaction when treated with ferric chlorid, and separatet-he sulfo group when heated with caustic solutions. and further change to amino, dcrivatcs when treated with to a totally different class of combinations reaction with ferric chlorid and which do with annnonia and caustic solut.ions,'separate the sulfo group.
- the salts of the sulfo acids of guaiacol carbonate are intermediate between the. two preparations of guaiacol inostused for medicinal purposes, namely, the guaiacol carbonate and the ,g'uaiacol sulfo acid salts (for instance. thiocol);
- the guaiacol carbonate and the ,g'uaiacol sulfo acid salts for instance. thiocol
- guaiacol In cont ardistinction to guaiacol"carbonate they have the advantage of being easily soluble in water, ,aiid-coinpared with t-hiocol they taste better and give no color reaction with ferric salts and can reparations for medicinal purposes.
- Example I Phosgen is passed into a cooled solution consist ng of 5 grams of the potassium salt of guaiacol sulfo acid (thiocol) and 3 grams ofcaustic potash i112? grams of water, until an acid reaction is shown; hereby the greater mass of the potassium salt of guaiacol carbonate disulfo acid is directly precipitated, and the remainder can phosgen in the presence of Cit . therefore be used in combination with ferric be separated from thefiltered solution with chlorid of potassium.
- the potassium salt of guaiacol carbonate di-sulfo acid crystallizes out-of a watery solution, and it gives no color reaction with zferricchlorid, and does.
- the potassium salt of aiacolcarbonate mono-sulfo acid is 'c stallized out of a watery solution, from which it separates in the form of fatty, lustrous,
- guaiacol carbonate sul o-acids which consists 1n causing phosgen to react on an alkaeasily soluble inwater and line bath containing the potassium salt of 'guaiacol sulfo-acid until the bath reacts acid.
- an alkali metal salt of a sulfo-acid of guaiacol-car- 'bonate which has the properties of being reaction with ferric saltsan when heated with ammonia .or with caustic alkali solution, does not split ofi the sulfo-group.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
, tains to nake anduse the same.
. 2111110311, '01 Munro 1 RINGER so To' alto/7 0m it may concern:
'Beit known that I, ALF ED EINHORN, citizen-of Germany, residing at Munich, Ba-
varia, Gern any, have invented certain new and useful Improvements in the Art of Making Guaiacol- Carbonate Sulforcid Derivatives; and do'hereby declare the follow ng to be a full, clear, and exact description of the invention, such as will enable others. skilled in the art to which it apper- This invention relates to the manufacture of guaiacol sulfo-acid derivatives and in particular to", the preparation of the salts of the sulfo-acids of gruaiacol carbonate.
a .The objects of the invention are to obtain .such salts of this character as are adapted .for therapeutic purposes, and which can be used together Withferric preparations with-- out inconvenience, producing no color reactions with them as is the case with guaiacol sulfo-acidsalts, and which, moreover, are more pleasant to the taste than the latter.
Viththese objects in view my invention consists in the class of compounds hereinafter described-and claimed and also in the process for making them as hereinafter dey ammonia, they are obviously not what th'ey have beensupposed'to be, but belong rather scribed and covered in the claims.
I have found-that the salts of the ninnoanddi-sulfo acids of guaiacol carbonate,
which are soluble inv water are formed when phosgen acts upon gualacol sulfo acids or known substitutes, as. for instance. bases of pyridin etc., according ,to the following formulae i QH d o -coo err nt-0on ooon=o nroon omoo.m+2no1 Up to now it has not been possible to proderivatives of the Specification (if-Letters Patent.-
inixtures of several salts.
not, when-"heated STATES PATENT OFF CE H, GERMANYWASSIGNQR TO THE FIRM. or o. jl isoim- OFYNIEDER'. INV'GELHEIM, ERMANY.
GUAIlACOL CARBONATE SULFO-ACID DERIVATIVE.
Patented 0a. 26, 1909.
Application filed June 22, 1908. Serial No. 439,842.
and tetrasali'cylid are formed from salicylic acid. but in no case the'carbonate of salicylic acid. In cooperation With Gustav Haas (Bcrz'chts dcr De-utshe'n' Ohe-mischcn GcseZZ- s(:/Laft,.vol. 38, page 3627,- see also his dissertation, Munich 1905, pages 15 and 30) it was pointed out that salicylic acid is not acted upon at all by alkali carbonates or hydrates. It was therefore to be expected that the-sulfoacids of guaiacol would, when treated withphosgen, behave similarly to salicylic acid, and it could not be foreseen that the very reverse would take place, and that they are capable of forming carbonates, in spite of the-acid sulfo group.
Salts of the sulfo acids of guaiacol carbonate have heretofore remained unknown. In the German patent specification No. 91078 salts of the sulfo acids of the aliphatic creosote ester are described. These, howeven'are in no way uniforn'i. and are most probably Sincethey give a color reaction when treated with ferric chlorid, and separatet-he sulfo group when heated with caustic solutions. and further change to amino, dcrivatcs when treated with to a totally different class of combinations reaction with ferric chlorid and which do with annnonia and caustic solut.ions,'separate the sulfo group.
The salts of the sulfo acids of guaiacol carbonate are intermediate between the. two preparations of guaiacol inostused for medicinal purposes, namely, the guaiacol carbonate and the ,g'uaiacol sulfo acid salts (for instance. thiocol); In cont ardistinction to guaiacol"carbonate they have the advantage of being easily soluble in water, ,aiid-coinpared with t-hiocol they taste better and give no color reaction with ferric salts and can reparations for medicinal purposes. Example I: Phosgen is passed into a cooled solution consist ng of 5 grams of the potassium salt of guaiacol sulfo acid (thiocol) and 3 grams ofcaustic potash i112? grams of water, until an acid reaction is shown; hereby the greater mass of the potassium salt of guaiacol carbonate disulfo acid is directly precipitated, and the remainder can phosgen in the presence of Cit . therefore be used in combination with ferric be separated from thefiltered solution with chlorid of potassium. The potassium salt of guaiacol carbonate di-sulfo acid crystallizes out-of a watery solution, and it gives no color reaction with zferricchlorid, and does. not reduce silver nitrate solutions, whereby it is distinguished from the potassium salt of guaiacol sulfo'acid (thiocol). From diluted alcohol. it-separates in fthe 'form of needles; in methyhc alcohol it is only very slightly soluble and .in." eth'yli'c alcohol quite insoluble: Neither hydrochloric acid nor sulfuric acid" alter the. concentrated watery solution f th Salt- Example II: Phosgen 1s'passedintoja cooled solution consisting of grams of the potassium salt of guaiacolsulfo acid (thiocol) and 10.4 grams of guaiacol in -L20 sium salt 'of guaiacol. carbonate mono-sulfo from methylic alcohol, in which it is only acid separates in the form of crystals, and finally, when alcohol is added to the filtered solution, the otassium sa t of guaia'col carbonate disul 0 acid is pr cipitated.
For purifying, the potassium salt of aiacolcarbonate mono-sulfo acid is 'c stallized out of a watery solution, from which it separates in the form of fatty, lustrous,
prismatic crystals; with ferric chlorid' it 'ves no color reaction; from diluted alcohol, m'which it dissolves'with difliculty, it crystallizes in the form of small lustrous needles;
with difficulty soluble, it separates in the form of long needles, and from absolutealc'ohol, in which it is only soluble with the greatest difliculty, it separates as microscopic indistinct crystals. An addition of hydrochloric acid or sulfuric acid to a concentrated solution of the salt produces no change.
The products obtained by this process are.
to be used for therapeutic purposes.
What I claim as my invention and desire to secure by Letters Patent, is:
1. The process for the roduction of salt LoUIs F. MUELLER,
'of guaiacol carbonate sul o-acids, which consists 1n causing phosgen to react on an alkaeasily soluble inwater and line bath containing the potassium salt of 'guaiacol sulfo-acid until the bath reacts acid.
'2. The process for the production of a salt" of guaiaeol carbonate sulfo-acids, which consists in passing phosgen into a cooled aqueous bath of a salt of aiacol sulfo-acid tog 'etherwith an alkali, until the bathreacts ac1d.. Y
3. The process for the production of asalt ofjguaiacol carbonate sulfo-acids, which con sists in passing hosgen into a' cooled aqueaiacol s'ulfo-acid toa of guaiacol carbonate sul o-a'cid's, which consists in passing phosgen into acooled aqueous bath of a'salt ofjguaicol sulfo-acid together "with an alkali, nntilthe bathreacts acid,
then separating the resulting precipitate and. finally treating the remainder of the bath" with potassium chlorid.
s a. new chemicalcompound, a salt ofa sulfo-acid of .guaiacol-carbonate, having the following properties 2-- It is easily soluble in waterand gives no color react-ion with ferric salts and, when heated with ammonia or with caustic alkali solution, does not split oil the sulfo-group.
6. As a new chemical compound, an alkali" metal salt of a sulfo-acid of guaiacol-car- 'bonate which has the properties of being reaction with ferric saltsan when heated with ammonia .or with caustic alkali solution, does not split ofi the sulfo-group.
7 As a new chemical compound the potassium salt. of the :disulfo-aicid of guaiacol: carbonate, which crystallizes out of water .and dilute alcohol, which crystallizes out of the latter in the form'of pointed needles, is
thebath with a halogen salt of an alkali... '4. The process for the roduction'of a salt giving no color only slightly soluble in methyl-alcohol and insoluble in concentrated ethyl-alcohol, which gives no color reaction with ferric salts and which is not altered by dilute mineral acids but is altered by alkalies.
In testimony whereof. I hereunto aflix my ALFRED EINHORN. Witnesses MATHILDE K. HELD.
signature in the presence of two witnesses;
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43984208A US938132A (en) | 1908-06-22 | 1908-06-22 | Guaiacol carbonate sulfo-acid derivative. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43984208A US938132A (en) | 1908-06-22 | 1908-06-22 | Guaiacol carbonate sulfo-acid derivative. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US938132A true US938132A (en) | 1909-10-26 |
Family
ID=3006552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US43984208A Expired - Lifetime US938132A (en) | 1908-06-22 | 1908-06-22 | Guaiacol carbonate sulfo-acid derivative. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US938132A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3299115A (en) * | 1963-06-26 | 1967-01-17 | Fmc Corp | Preparation of bis (trichloroethyl) carbonate |
| US3396187A (en) * | 1964-06-03 | 1968-08-06 | Atomic Energy Commission Usa | Beta-di and trinitro carbonates and method for their production |
-
1908
- 1908-06-22 US US43984208A patent/US938132A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3299115A (en) * | 1963-06-26 | 1967-01-17 | Fmc Corp | Preparation of bis (trichloroethyl) carbonate |
| US3396187A (en) * | 1964-06-03 | 1968-08-06 | Atomic Energy Commission Usa | Beta-di and trinitro carbonates and method for their production |
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