US815193A - Production of aromatic alcohols. - Google Patents
Production of aromatic alcohols. Download PDFInfo
- Publication number
- US815193A US815193A US28232105A US1905282321A US815193A US 815193 A US815193 A US 815193A US 28232105 A US28232105 A US 28232105A US 1905282321 A US1905282321 A US 1905282321A US 815193 A US815193 A US 815193A
- Authority
- US
- United States
- Prior art keywords
- cathode
- aromatic alcohols
- production
- parts
- hundred
- 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
- 238000004519 manufacturing process Methods 0.000 title description 6
- -1 aromatic alcohols Chemical class 0.000 title description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229940032330 sulfuric acid Drugs 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- 235000012501 ammonium carbonate Nutrition 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- AFPHTEQTJZKQAQ-UHFFFAOYSA-N 3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1 AFPHTEQTJZKQAQ-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- 241001527902 Aratus Species 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229940001593 sodium carbonate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/25—Reduction
Definitions
- Example 1 Introduce into the cathode- 3 5 compartment of an electrolyticapparatus a solution of two hundred (200) parts of benzoic acid in four hundred (400) parts of concentrated sulfuric acid and fourteen hundred (1 ,400) parts ofalcohol.
- the cathode should o consist of sheet-lead pre are'dfaccording to the receipt given by Tafe inthe Berichte, 33, 2,215.
- the anode should consist of pure lead, and the anode-compartment should be filled With dilute sulfuric acid, Send through the liquid, an electric currentof from six (6) to twelve (12) amperes per one hundred I (100) s uare centimeters of cathode-surface and coo by means of water, so that the temperature remains between twenty (20) and. I 5o forty (40) degrees centigrade.
- an electric currentof from six (6) to twelve (12) amperes per one hundred I (100) s uare centimeters of cathode-surface and coo by means of water, so that the temperature remains between twenty (20) and. I 5o forty (40) degrees centigrade.
- As soon as no more hydro en is absorbed neutralize the cathode li u1d with caustic soda andextract the alcoho which is'form ed by means of ether.
- Example 2 Introduce into the cathode compartment of an electrolytic apparatus a solution of twenty (20) parts of para-hydroXy-benzoic acid, fifty-five parts of concentrated sulfuric acid, and fifty-six (56) parts of alcohol.
- the cathode and the anode should ,consist of pure lead, and the anode compartment should be filled with thirty I (30) per cent. sulfuric acid.
- Example .3 Introduce into the cathodecompartment of an electrolytic app aratus a solution of one (1) part of anthranilic acid in fifteen (15) parts of sulfuricacid and carry out the electrolysis in the manner described- .in the-foregoing'example 2, taking care that the temperature ofthe cathode liquid does not exceedthirty (30) degrees centigrade. Then add solid ammonium carbonate to the Filter,
- Example, 4 Dissolve one hundred grams of meta-nitro-benzoic acid in one (1) liter of thirty (30) per cent. alcoholic sulfuric acid and reduce th s in themanner described in the foregoing examples, maintaining the temperature at about forty (40) de rees ICO Centigrade. After passing about three undred (300) I ampere hours through the cell .make the reaction liquid alkaline by means.
- boxylic acids making use of a lead cathode.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Description
To all whore it may concern:
4 UNITED STATES PA 'rENT Oman CARL METTLER; "OF MUNICH,
"GERMANY, ASSIGNORITO simsm ANI'LIN & OD I F 'LUDWlGSHAFEN-ON THERHINE, ER NY, ,A'
" CORPORATION.
, No.e 193.,,
Be it known thatgI, OARL'METTLER, doctor of philosophy and chemist, a citizen of the SWISS Republic, residing at Munich, in the 5 Kingdom'of Bavaria, German Empire, have invented new and useful Improvements in the Production of Aromatic Alcohols, of-
metal of high cathodic tension, and for this purpose lead is particularly useful, although of course other metalssuch,for instance, as mercurywhich fulfil the above condition maybeemployed. The courseof the reac- 2 5 tioncan be convenientlyillustrated by the following equation: p I iacooHHH':ctntcnzormn o.
l I 'The'foll owing examples will serve tofur o 'ther illustrate the nature of my invention and the manner of carrying it into practical effect ;-but-my invention is not confined to these examples. The parts are by- Weight. Example 1: Introduce into the cathode- 3 5 compartment of an electrolyticapparatus a solution of two hundred (200) parts of benzoic acid in four hundred (400) parts of concentrated sulfuric acid and fourteen hundred (1 ,400) parts ofalcohol. The cathode should o consist of sheet-lead pre are'dfaccording to the receipt given by Tafe inthe Berichte, 33, 2,215. The anode should consist of pure lead, and the anode-compartment should be filled With dilute sulfuric acid, Send through the liquid, an electric currentof from six (6) to twelve (12) amperes per one hundred I (100) s uare centimeters of cathode-surface and coo by means of water, so that the temperature remains between twenty (20) and. I 5o forty (40) degrees centigrade. As soon as no more hydro en is absorbed neutralize the cathode li u1d with caustic soda andextract the alcoho which is'form ed by means of ether. The yield of benzyl alcoholboiling at A Specification of Letters Patent. I Applioationfiledootober11,19 05. Se rial:1lo. 282,32ll. T
meters of the cathode-surface.
residue'by means of ether.
{PRODUCTION OF ARomArioiALcoi-ioLsi.
ented March 13,
a temperatureof two hundred and one (201) degrees centigr'ade is almost quantitative.
Example 2: Introduce into the cathode compartment of an electrolytic apparatus a solution of twenty (20) parts of para-hydroXy-benzoic acid, fifty-five parts of concentrated sulfuric acid, and fifty-six (56) parts of alcohol. The cathode and the anode should ,consist of pure lead, and the anode compartment should be filled with thirty I (30) per cent. sulfuric acid. Pass through the cell an electric current of ten (10) amperes per one "hundred (100) square centifrom two (2) to three, (3) times the theoretically-necessary quantity of electricity has been passed through the cell work up the cathode liquid by adding sodium-carbonate solution untilit is alkaline and drive ed the alcohol employed by distilling with steam.
Then extract the reaction productfromthe As soon as The reduction of meta-hydroxy-benzoic acid can be carried out in a'manner s1m1lar to that above described.
Example .3: Introduce into the cathodecompartment of an electrolytic app aratus a solution of one (1) part of anthranilic acid in fifteen (15) parts of sulfuricacid and carry out the electrolysis in the manner described- .in the-foregoing'example 2, taking care that the temperature ofthe cathode liquid does not exceedthirty (30) degrees centigrade. Then add solid ammonium carbonate to the Filter,
cathodev liquid until it is alkaline. 'saturate'the filtratewith ammonium sulfate, and extract with ether; On distilling off the other ortho-amido-benzylalcohol' remains" behind in theform of an oil which solidifies and can bepurified by crystallization from lightpetroleum.
Example, 4: Dissolve one hundred grams of meta-nitro-benzoic acid in one (1) liter of thirty (30) per cent. alcoholic sulfuric acid and reduce th s in themanner described in the foregoing examples, maintaining the temperature at about forty (40) de rees ICO Centigrade. After passing about three undred (300) I ampere hours through the cell .make the reaction liquid alkaline by means.
of ammonium carbonate, saturate with ammonium sulfate,,and extract several times with ether. Upon :distillation the ether leaves behind tan oil which rapidly solidifies,
and by crystallization alcohol can be obtained crystalline needles.
N 0w what I claim is- 5 1. The manufacture of aromatic alcohols by electrolytically reducing aromatic carmeta-amido-benzyl l 3. The manufacture of para-hydroxy-benhydroXy-benzoic acid, cathode. y
In testimony whereof I have hereunto set I my hand in the presence of two subscrihin making use of a lead boxylic acids making use of a cathode of high Witnesses. cathodic tension CARL METTLER.
2. The manufacture of aromatic alcohols Witnesses:
MATHILDE K. HELD,
ro by electrolytically reducing aromatic car- GEORG KoRNER.
boxylic acids, making use of a lead cathode.
in the form of white l zyl alcohol by electrolytically reducing para-
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28232105A US815193A (en) | 1905-10-11 | 1905-10-11 | Production of aromatic alcohols. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28232105A US815193A (en) | 1905-10-11 | 1905-10-11 | Production of aromatic alcohols. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US815193A true US815193A (en) | 1906-03-13 |
Family
ID=2883674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US28232105A Expired - Lifetime US815193A (en) | 1905-10-11 | 1905-10-11 | Production of aromatic alcohols. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US815193A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3755101A (en) * | 1970-11-19 | 1973-08-28 | Rhone Poulenc Sa | Process for the preparation of saligenol |
| US3947500A (en) * | 1969-11-07 | 1976-03-30 | Halcon International, Inc. | Process for treating reaction mixtures by chemical reduction |
| US3947501A (en) * | 1969-11-07 | 1976-03-30 | Halcon International, Inc. | Process for treatment of reaction mixtures by hydrogenation |
| US3984293A (en) * | 1974-09-02 | 1976-10-05 | Smith Kline & French Laboratories Limited | Process of reduction |
| US4055573A (en) * | 1976-05-06 | 1977-10-25 | Smithkline Corporation | Electrochemical reduction of imidazolecarboxylic esters |
-
1905
- 1905-10-11 US US28232105A patent/US815193A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3947500A (en) * | 1969-11-07 | 1976-03-30 | Halcon International, Inc. | Process for treating reaction mixtures by chemical reduction |
| US3947501A (en) * | 1969-11-07 | 1976-03-30 | Halcon International, Inc. | Process for treatment of reaction mixtures by hydrogenation |
| US3755101A (en) * | 1970-11-19 | 1973-08-28 | Rhone Poulenc Sa | Process for the preparation of saligenol |
| US3984293A (en) * | 1974-09-02 | 1976-10-05 | Smith Kline & French Laboratories Limited | Process of reduction |
| US4055573A (en) * | 1976-05-06 | 1977-10-25 | Smithkline Corporation | Electrochemical reduction of imidazolecarboxylic esters |
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