US3656886A - Corrosion inhibitors - Google Patents
Corrosion inhibitors Download PDFInfo
- Publication number
- US3656886A US3656886A US2439A US3656886DA US3656886A US 3656886 A US3656886 A US 3656886A US 2439 A US2439 A US 2439A US 3656886D A US3656886D A US 3656886DA US 3656886 A US3656886 A US 3656886A
- Authority
- US
- United States
- Prior art keywords
- cuprous
- percent
- weight
- copper
- salicylic 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
- 238000005260 corrosion Methods 0.000 title description 15
- 230000007797 corrosion Effects 0.000 title description 15
- 239000003112 inhibitor Substances 0.000 title description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 229910052751 metal Inorganic materials 0.000 claims abstract description 17
- 239000002184 metal Substances 0.000 claims abstract description 17
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910001431 copper ion Inorganic materials 0.000 claims abstract description 8
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000003870 salicylic acids Chemical class 0.000 claims description 4
- 239000000243 solution Substances 0.000 abstract description 12
- 238000000926 separation method Methods 0.000 abstract description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 9
- 150000001336 alkenes Chemical class 0.000 abstract description 7
- 239000012457 nonaqueous media Substances 0.000 abstract description 3
- -1 ferrous metals Chemical class 0.000 description 8
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 7
- 238000007792 addition Methods 0.000 description 5
- 239000010949 copper Substances 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
- 229910000975 Carbon steel Inorganic materials 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000010962 carbon steel Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 229960001860 salicylate Drugs 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SUSANQWSCSKXPF-UHFFFAOYSA-N 2-(2-methylpropoxy)benzoic acid Chemical class CC(C)COC1=CC=CC=C1C(O)=O SUSANQWSCSKXPF-UHFFFAOYSA-N 0.000 description 1
- MQFDMZNZEHTLND-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]benzoic acid Chemical class CC(C)(C)OC1=CC=CC=C1C(O)=O MQFDMZNZEHTLND-UHFFFAOYSA-N 0.000 description 1
- UABHETFCVNRGNL-UHFFFAOYSA-N 2-butoxybenzoic acid Chemical class CCCCOC1=CC=CC=C1C(O)=O UABHETFCVNRGNL-UHFFFAOYSA-N 0.000 description 1
- XDZMPRGFOOFSBL-UHFFFAOYSA-N 2-ethoxybenzoic acid Chemical class CCOC1=CC=CC=C1C(O)=O XDZMPRGFOOFSBL-UHFFFAOYSA-N 0.000 description 1
- HXISMZRZHNLOHG-UHFFFAOYSA-N 2-hydroxy-3,4-di(propan-2-yl)benzoic acid Chemical class CC(C)C1=CC=C(C(O)=O)C(O)=C1C(C)C HXISMZRZHNLOHG-UHFFFAOYSA-N 0.000 description 1
- WWPLDSOFBMZGIJ-UHFFFAOYSA-N 2-propan-2-yloxybenzoic acid Chemical class CC(C)OC1=CC=CC=C1C(O)=O WWPLDSOFBMZGIJ-UHFFFAOYSA-N 0.000 description 1
- KDZRUIVFVWCNFI-UHFFFAOYSA-N 3,4,5-triethyl-2-hydroxybenzoic acid Chemical compound C(C)C1=C(C(=C(C(C(=O)O)=C1)O)CC)CC KDZRUIVFVWCNFI-UHFFFAOYSA-N 0.000 description 1
- ZMOYRWRFFNYCNX-UHFFFAOYSA-N 3,4-diethyl-2-hydroxybenzoic acid Chemical class CCC1=CC=C(C(O)=O)C(O)=C1CC ZMOYRWRFFNYCNX-UHFFFAOYSA-N 0.000 description 1
- DUKPKQFHJQGTGU-UHFFFAOYSA-N Hexyl salicylic acid Chemical class CCCCCCOC(=O)C1=CC=CC=C1O DUKPKQFHJQGTGU-UHFFFAOYSA-N 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-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
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- FNLAYLGCSJCNIB-UHFFFAOYSA-N acetonitrile;ethane-1,2-diol Chemical compound CC#N.OCCO FNLAYLGCSJCNIB-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/12—Oxygen-containing compounds
- C23F11/124—Carboxylic acids
Definitions
- Preferred corrosion inhibitors according to the invention are metal salts of the alkyl substituted and unsubstituted salicyclic acids such as metal salts of salicylic acid, ethyl salicylic acid, isopropyl salicylic acid, n-butyl salicylic acid, isobutyl salicylic acid, tert-butyl salicylic acid, hexyl salicylic acid, diethyl salicylic acid, diisopropyl salicylic acid, ditertiarybutyl salicylic acid, diisobutyl salicylic acid, ditertiary-pentyl salicylic acid, tri-ethyl salicylic acid, and the like.
- metal salts of salicylic acid having at least one but not more than two alkyl substituents each of from about two to about six carbon atoms.
- Metal salts of dialkyl substituted salicylic acids having from two to six carbons per alkyl substituent are most preferred.
- metal ions in the metal salt inhibitors according to the invention may be used monovalent metal ions such as ions of the alkali metals and transition metals, for example, Sodium 1, Potassium I, Lithium 1, Copper 1, and Silver 1,.
- Cuprous (Copper 1) is a preferred metal for inhibitor salts according to the invention.
- Most preferred as inhibitor salts are the cuprous salts of dialkyl substituted salicyclic acids having from two to six carbon atoms per substituent, such as cuprous diisopropyl salicylate, cuprous ditertiary-butyl salicylate, and cuprous ditertiary-pentyl .salicylate. Mixtures of inhibitor salts may be employed.
- the inhibitors according to the invention may be used to prevent corrosion in any non-aqueous solvented cuprous ion olefin separation process. They are especially useful in preventing corrosion in processes which use propionitrile as cuprous salt solvent and which contain a minimum of about 5 percent by weight of cuprous copper such as that described in U-.S.Pat.No. 3,401,112.
- the amount of inhibitor salt added to olefin separation systems may vary widely. Generally suitable for additions of inhibitor salt equivalent to from about 1 to about 20 percent by mole of the cuprous salt present in such cuprous olefin separation systems. When the preferred alkyl substituted metal salicylates are employed, additions of from about 2 percent to about 15 .percent by mole (based on the total-moles of cuprous ion present) are preferred. Especially preferred are additions of from about 3 percent to about 10 percent by mole based on the total moles of cuprous ion present.
- EXAMPLE I A sample of mild carbon steel was prepared and immersed in a non-aqueous solution of cuprous salt suitable for use in olefin separation processes.
- the solution contained 12 percent by weight cuprous ion, supplied as triiluoroacetate and about 1.5 percent by weight of cupric ion.
- Propionitrile was the solvent. Corrosion rate of the steel samples was determined by weight loss of the sample after a measured time interval. The sample was held at C during the test. Without the addition of inhibitor, the corrosion rate as 34 m.p.y. A second sample was immersed in a similar cuprous trifluoroacetate solution in propionitrile to which had been added 5 percent by weight of an inhibitor according to the invention, cuprous ditertiary-butyl salicylate. This propionitrile solution contained 12 percent by weight of cuprous ion and 1.3 percent by weight of cupric ion. The corrosion rate at 100 C. was 3m.p.y.
- nonaqueous solution of copper ions is a propionitrile solution which contains a minimum of about 5 percent by weight of cuprous copper.
- metal salts are selected from the group consisting of cuprous salts of salicylic acids having two alkyl substituents each of from about two to about six carbon atoms and such salt is added in amount equivalent to from about 1 to about 20 percent by mole of the copper ion present.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Organic Chemistry (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US243970A | 1970-01-12 | 1970-01-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3656886A true US3656886A (en) | 1972-04-18 |
Family
ID=21700768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2439A Expired - Lifetime US3656886A (en) | 1970-01-12 | 1970-01-12 | Corrosion inhibitors |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3656886A (enrdf_load_stackoverflow) |
| JP (1) | JPS5335010B1 (enrdf_load_stackoverflow) |
| BE (1) | BE761426A (enrdf_load_stackoverflow) |
| CA (1) | CA970954A (enrdf_load_stackoverflow) |
| DE (1) | DE2100968C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2076046B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1296015A (enrdf_load_stackoverflow) |
| NL (1) | NL7100290A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5417725A (en) * | 1994-02-01 | 1995-05-23 | Graves; Gordon C. | Penetration and fixture freeing agent |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3758606A (en) * | 1972-06-02 | 1973-09-11 | Exxon Research Engineering Co | Corrosion inhibitors for cuprous tetrachloroaluminate complexes |
| JPS55122250A (en) * | 1979-01-17 | 1980-09-19 | Hitachi Ltd | Cassette tape recorder |
| US5643534A (en) * | 1995-07-20 | 1997-07-01 | Betzdearborn Inc. | Corrosion inhibitor for alkanolamine units |
| MD4321C1 (ro) * | 2014-01-21 | 2015-09-30 | Институт Химии Академии Наук Молдовы | Inhibitor de coroziune a oţelului în apă |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1940041A (en) * | 1931-09-30 | 1933-12-19 | Avis Braxton Davenport | Process and product for preventing rust and corrosion |
| US2182612A (en) * | 1937-01-30 | 1939-12-05 | American Distilling Company In | Product for use as nonrusting and noncorroding antifreezing mixtures |
| US2197832A (en) * | 1938-05-07 | 1940-04-23 | Socony Vacuum Oil Co Inc | Mineral oil composition |
| US2258591A (en) * | 1938-12-05 | 1941-10-14 | Shell Dev | Lubricating oil composition |
| US2311931A (en) * | 1941-12-27 | 1943-02-23 | American Cyanamid Co | Lubricant |
| US2714092A (en) * | 1953-03-04 | 1955-07-26 | Texas Co | Lithium base grease containing group ii divalent metal alkyl salicylate, such as zinc alkyl salicylate, as copper corrosion inhibitor |
| US3349043A (en) * | 1966-01-19 | 1967-10-24 | Manning Dev Corp | Methods and compositions for controlling oxidation of metal surfaces |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2623835A (en) * | 1941-03-14 | 1952-12-30 | Shell Dev | Anticorrosive metal article and method of making same |
| DE1256513B (de) * | 1962-09-21 | 1967-12-14 | Westinghouse Electric Corp | Verfahren zur Entseuchung von mit radioaktiven Korrosionsprodukten verunreinigten Metalloberflaechen |
-
1970
- 1970-01-12 US US2439A patent/US3656886A/en not_active Expired - Lifetime
-
1971
- 1971-01-11 NL NL7100290A patent/NL7100290A/xx not_active Application Discontinuation
- 1971-01-11 GB GB1296015D patent/GB1296015A/en not_active Expired
- 1971-01-11 FR FR7100629A patent/FR2076046B1/fr not_active Expired
- 1971-01-11 DE DE2100968A patent/DE2100968C2/de not_active Expired
- 1971-01-11 JP JP71305A patent/JPS5335010B1/ja active Pending
- 1971-01-11 CA CA102,398A patent/CA970954A/en not_active Expired
- 1971-01-11 BE BE761426A patent/BE761426A/xx unknown
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1940041A (en) * | 1931-09-30 | 1933-12-19 | Avis Braxton Davenport | Process and product for preventing rust and corrosion |
| US2182612A (en) * | 1937-01-30 | 1939-12-05 | American Distilling Company In | Product for use as nonrusting and noncorroding antifreezing mixtures |
| US2197832A (en) * | 1938-05-07 | 1940-04-23 | Socony Vacuum Oil Co Inc | Mineral oil composition |
| US2258591A (en) * | 1938-12-05 | 1941-10-14 | Shell Dev | Lubricating oil composition |
| US2311931A (en) * | 1941-12-27 | 1943-02-23 | American Cyanamid Co | Lubricant |
| US2714092A (en) * | 1953-03-04 | 1955-07-26 | Texas Co | Lithium base grease containing group ii divalent metal alkyl salicylate, such as zinc alkyl salicylate, as copper corrosion inhibitor |
| US3349043A (en) * | 1966-01-19 | 1967-10-24 | Manning Dev Corp | Methods and compositions for controlling oxidation of metal surfaces |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5417725A (en) * | 1994-02-01 | 1995-05-23 | Graves; Gordon C. | Penetration and fixture freeing agent |
Also Published As
| Publication number | Publication date |
|---|---|
| CA970954A (en) | 1975-07-15 |
| FR2076046B1 (enrdf_load_stackoverflow) | 1973-10-19 |
| NL7100290A (enrdf_load_stackoverflow) | 1971-07-14 |
| JPS5335010B1 (enrdf_load_stackoverflow) | 1978-09-25 |
| BE761426A (fr) | 1971-07-12 |
| DE2100968C2 (de) | 1981-10-01 |
| FR2076046A1 (enrdf_load_stackoverflow) | 1971-10-15 |
| DE2100968A1 (de) | 1972-07-13 |
| GB1296015A (enrdf_load_stackoverflow) | 1972-11-15 |
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