US698355A - Process of making aromatic aldehyde and acid. - Google Patents
Process of making aromatic aldehyde and acid. Download PDFInfo
- Publication number
- US698355A US698355A US5149701A US1901051497A US698355A US 698355 A US698355 A US 698355A US 5149701 A US5149701 A US 5149701A US 1901051497 A US1901051497 A US 1901051497A US 698355 A US698355 A US 698355A
- Authority
- US
- United States
- Prior art keywords
- acid
- nickel
- peroxid
- aromatic aldehyde
- toluene
- 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 8
- 150000003934 aromatic aldehydes Chemical class 0.000 title description 6
- 238000000034 method Methods 0.000 title description 6
- 159000000032 aromatic acids Chemical class 0.000 title description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 21
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 229910052759 nickel Inorganic materials 0.000 description 8
- 239000005708 Sodium hypochlorite Substances 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 6
- 229960005076 sodium hypochlorite Drugs 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 4
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 2
- PLAZTCDQAHEYBI-UHFFFAOYSA-N 2-nitrotoluene Chemical compound CC1=CC=CC=C1[N+]([O-])=O PLAZTCDQAHEYBI-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 229960004365 benzoic acid Drugs 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229960000443 hydrochloric acid Drugs 0.000 description 2
- 235000011167 hydrochloric acid Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002815 nickel Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical compound [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Inorganic materials Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- -1 nickel oxid aldehyde Chemical class 0.000 description 1
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- SATVIFGJTRRDQU-UHFFFAOYSA-N potassium hypochlorite Chemical compound [K+].Cl[O-] SATVIFGJTRRDQU-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
Definitions
- aldehydes can be obtained from aromatic hydrocarbons containing a methyl group and certain of their derivatives, such as are mentioned in the specifications of Patents No. 613,460, November 1, 1898; No. 650,332, May 22, 1900; No. 661,872, November 13, 1900; No. 677,239, June 25, 1901- for example, toluene, xylene, nitro-toluene, and the like-by oxidizing the said bodies with manganese peroxid, with or without the addition of sulfuric acid.
- the body to be oxidized is heated with dry nickel peroxid (which can be prepared from nickel salts in the well-known manner by means of alkali and chlorin or bromin or sodium hypochlorite) in the boiling-water bath for from five (5) to six (6) hours, the oxidation product formed and unattached initial material are separated from the nickel oxid aldehyde is isolated from the filtrate or distillate in the well-known manner by means of sodium bisulfite.
- the oxidation can also be carried out by directly passing steam into the mixture of nickel oxid and the body to be oxidized, thus distilling off the aldehyde as it is formed, together with unchanged initial material.
- the amount of organic acid formed can be diminished by adding a nickel or cobalt saltfor example, nickel chlorid (NiOl )-or a small quantity of an acid, such as sulfuric acid, to the reaction mixture.
- the nickel peroxid is reduced in part or entirely to a lower oxid, which can be reconverted by means of asuitable oxidizing agent--for example, sodiumhypochlorite solution-into the original oxid and at once used again, or the lower oxid formed can be retransformed into the original peroxid during the course of the reaction by slowly adding a suitable oxidizing agent, such as sodium hypochlorite, to the reaction mixture.
- a suitable oxidizing agent for example, sodiumhypochlorite solution-into the original oxid and at once used again, or the lower oxid formed can be retransformed into the original peroxid during the course of the reaction by slowly adding a suitable oxidizing agent, such as sodium hypochlorite, to the reaction mixture.
- Example 1 Heat together three hundred (300) parts of toluene with one hundred and fifty (150) parts of nickel peroxid at a temperature of one hundred (100) degrees centigradefor from five (5) to six (6) hours. Filter the liquid from the nickel body and sep arate the benzaldehyde formed from unaltered toluene by shaking the mixture with by filtration or distillation in steam, and the aqueoussodium-bisulfite solution and isolate the aldehyde in the well-known manner.
- Example 2 Mix together three hundred (300) parts of ortho-nitro-toluene, fifty (50) parts Ofnickel peroxid, and five (5) parts of nickel chlorid, (NiCl Pass steam into the mixture while slowly running in ten parts, by volume, of sodiuni-hypochlorite solution,(containing ten per cent. of active chlorin.) ⁇ Vhen nothing more comes over with the steam, isolate from the distillate the ortho-nitro-benzaldehyde formed by means of sodium bisulfite in the well-known manner. To obtain the ortho-nitro-benzoic acid formed, filter the contents of the distilling vessel, eoncentrate the filtrate, and acidify it with hydrochloricacid. The ortho-nitro-benzoicacid separates out.
- nickel chlorid in the above example can be replaced, for instance, by four (4) parts of sulfuric acid (containing one hundred per cent. of H 80 or by a suitable quantity of hydrochloric or other acid acting similarly.
- cobalt peroxid or a cobalt salt can be employed instead of nickel peroxid or a nickel salt, respectively.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
' PATENT GFFICE,
MAX BAZLEN, OF LUDWIGSI-IAFEN,
GERMANY, ASSIGNOR TO BADISCHE ANILIN & SODA FABRIK, OF LUDVVIGSHAFEN, GERMANY, A CORPO- RATION OF BADEN, GERMANY.
PROCESS OF MAKING AROMATIC ALDEHYDE AND ACID.
SPECIFICATION forming part of Letters Patent No. 698,355, dated April 22, 1902.
$erial No. 51,497. (No specimens.)
To all whom, it may concern:
Be it known that I, MAX BAZLEN, doctor of philosophy and chemist, a subject of the King of Wiirtemberg, residing at Ludwigshafen-on-the-Rhine, in the Kingdom of Bavaria and Empire of Germany, have invented new and useful Improvements in the Mannfacture of Aromatic Aldehydes and Acids, of which the following is a specification.
It is known that aldehydes can be obtained from aromatic hydrocarbons containing a methyl group and certain of their derivatives, such as are mentioned in the specifications of Patents No. 613,460, November 1, 1898; No. 650,332, May 22, 1900; No. 661,872, November 13, 1900; No. 677,239, June 25, 1901- for example, toluene, xylene, nitro-toluene, and the like-by oxidizing the said bodies with manganese peroxid, with or without the addition of sulfuric acid.
I have discovered that the oxidation of the substances to which I have above referred (to which I hereinafter apply the generic term toluene substance as including all of them) to aldehydes can be effected by means of certain oxide which have never been employed before for this purpose and which have the property of decomposing sodium-hypochlorite solution, (thereby generating 0xygen)- namely, the so-called peroxid of nickel or cobalt-the oxidation taking place in the presence or absence of sulfuric acid. In addition to aldehyde a certain amount of the corresponding carboxylic acid is, as a rule, formed during the reaction. Hereinafter I apply the term peroxid to that oxid which a can be obtained from the hydrochloric salt of the metal in question, caustic soda, and chlorin. The oxidation takes place in most cases at or below a temperature of one hundred (100) degrees centigrade; but the temperature can of course be varied without de parting from my invention. For example, the body to be oxidized is heated with dry nickel peroxid (which can be prepared from nickel salts in the well-known manner by means of alkali and chlorin or bromin or sodium hypochlorite) in the boiling-water bath for from five (5) to six (6) hours, the oxidation product formed and unattached initial material are separated from the nickel oxid aldehyde is isolated from the filtrate or distillate in the well-known manner by means of sodium bisulfite. The oxidation can also be carried out by directly passing steam into the mixture of nickel oxid and the body to be oxidized, thus distilling off the aldehyde as it is formed, together with unchanged initial material. The organic acid which is formed in addition to the aldehyde and which corresponds to the hydrocarbon used as initial material-for example, benzoic acid being obtained from toluene, ortho-nitro'benzoic acid from ortho-nitrotoluene, and so oil-can be isolated by filtering the liquid remaining in the distilling vessel, concentrating the filtrate, and acidifying the same with hydrochloric acid. The amount of organic acid formed can be diminished by adding a nickel or cobalt saltfor example, nickel chlorid (NiOl )-or a small quantity of an acid, such as sulfuric acid, to the reaction mixture. In the course of the reaction the nickel peroxid is reduced in part or entirely to a lower oxid, which can be reconverted by means of asuitable oxidizing agent--for example, sodiumhypochlorite solution-into the original oxid and at once used again, or the lower oxid formed can be retransformed into the original peroxid during the course of the reaction by slowly addinga suitable oxidizing agent, such as sodium hypochlorite, to the reaction mixture.
The following examples will serve to further illustrate the nature of my invention and the best manner I know of carrying it into practical effect; but I do not confine myself to the details therein given. The parts are by Weight.
Example 1: Heat together three hundred (300) parts of toluene with one hundred and fifty (150) parts of nickel peroxid at a temperature of one hundred (100) degrees centigradefor from five (5) to six (6) hours. Filter the liquid from the nickel body and sep arate the benzaldehyde formed from unaltered toluene by shaking the mixture with by filtration or distillation in steam, and the aqueoussodium-bisulfite solution and isolate the aldehyde in the well-known manner.
Example 2: Mix together three hundred (300) parts of ortho-nitro-toluene, fifty (50) parts Ofnickel peroxid, and five (5) parts of nickel chlorid, (NiCl Pass steam into the mixture while slowly running in ten parts, by volume, of sodiuni-hypochlorite solution,(containing ten per cent. of active chlorin.) \Vhen nothing more comes over with the steam, isolate from the distillate the ortho-nitro-benzaldehyde formed by means of sodium bisulfite in the well-known manner. To obtain the ortho-nitro-benzoic acid formed, filter the contents of the distilling vessel, eoncentrate the filtrate, and acidify it with hydrochloricacid. The ortho-nitro-benzoicacid separates out.
The nickel chlorid in the above example can be replaced, for instance, by four (4) parts of sulfuric acid (containing one hundred per cent. of H 80 or by a suitable quantity of hydrochloric or other acid acting similarly. In every case cobalt peroxid or a cobalt salt can be employed instead of nickel peroxid or a nickel salt, respectively.
In place of the sodium hypochlorite employed in the preceding examples there may be employed calcium hypochlorite, potassium hypochlorite or sodium, potassium or calcium 'hypobromites, to all of which I hereinafter apply the generic term oxidizing agent.
Now what I claim is- 1. The process of making aromatic aldehyde and acid which consists in treating a hereinbefore-defined toluene substance with the peroxid of a metal of the nickel group, a salt of a mctalof the nickel group and asuitable oxidizing agent.
2. The process of making aromatic aldehyde and acid which consists in treating a hereinbefore-defined toluene substance with the peroxid of a metal of the nickel group and a salt of a metal of the nickel group.
3. The process of making aromatic aldehyde and acid which consists in treating a hereinbefore-defined toluene substance with the peroxid of a metal of the nickel group.
4. The process of making ortho-nitro-benzaldehyde and ortho-nitro-benzoic acid which consists in treating ortho-nitr0-to1uene with nickel peroxid, nickel chlorid and sodium hypochlorite.
In testimony whereof I have hereunto set my hand in the presence of two subscribing witnesses.
MAX BAZLEN.
\Vitnesses:
JOHN L. IIEMKE, PAUL JULIUS.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5149701A US698355A (en) | 1901-03-16 | 1901-03-16 | Process of making aromatic aldehyde and acid. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5149701A US698355A (en) | 1901-03-16 | 1901-03-16 | Process of making aromatic aldehyde and acid. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US698355A true US698355A (en) | 1902-04-22 |
Family
ID=2766888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US5149701A Expired - Lifetime US698355A (en) | 1901-03-16 | 1901-03-16 | Process of making aromatic aldehyde and acid. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US698355A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2416350A (en) * | 1944-02-11 | 1947-02-25 | Standard Oil Dev Co | Production of phthalic acid |
| US2544562A (en) * | 1947-07-18 | 1951-03-06 | Stanolind Oil & Gas Co | Process for recovering aldehydes and ketones |
| US3791345A (en) * | 1972-05-09 | 1974-02-12 | Itek Corp | Liquid toner applicator |
-
1901
- 1901-03-16 US US5149701A patent/US698355A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2416350A (en) * | 1944-02-11 | 1947-02-25 | Standard Oil Dev Co | Production of phthalic acid |
| US2544562A (en) * | 1947-07-18 | 1951-03-06 | Stanolind Oil & Gas Co | Process for recovering aldehydes and ketones |
| US3791345A (en) * | 1972-05-09 | 1974-02-12 | Itek Corp | Liquid toner applicator |
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