US815193A - Production of aromatic alcohols. - Google Patents

Production of aromatic alcohols. Download PDF

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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
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cathode
aromatic alcohols
production
parts
hundred
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US28232105A
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Carl Mettler
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BASF SE
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BASF SE
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    • 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.

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-
US28232105A 1905-10-11 1905-10-11 Production of aromatic alcohols. Expired - Lifetime US815193A (en)

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Cited By (5)

* Cited by examiner, † Cited by third party
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
US3947501A (en) * 1969-11-07 1976-03-30 Halcon International, Inc. Process for treatment of reaction mixtures by hydrogenation
US3947500A (en) * 1969-11-07 1976-03-30 Halcon International, Inc. Process for treating reaction mixtures by chemical reduction
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

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3947501A (en) * 1969-11-07 1976-03-30 Halcon International, Inc. Process for treatment of reaction mixtures by hydrogenation
US3947500A (en) * 1969-11-07 1976-03-30 Halcon International, Inc. Process for treating reaction mixtures by chemical reduction
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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