US2913408A - Corrosion inhibitors for ferrous metals in aqueous solutions of non-oxidizing acids - Google Patents
Corrosion inhibitors for ferrous metals in aqueous solutions of non-oxidizing acids Download PDFInfo
- Publication number
- US2913408A US2913408A US631045A US63104556A US2913408A US 2913408 A US2913408 A US 2913408A US 631045 A US631045 A US 631045A US 63104556 A US63104556 A US 63104556A US 2913408 A US2913408 A US 2913408A
- Authority
- US
- United States
- Prior art keywords
- acid
- ferrous metals
- aqueous solutions
- corrosion inhibitors
- inhibitor
- 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
- 239000003112 inhibitor Substances 0.000 title claims description 24
- 239000002253 acid Substances 0.000 title claims description 21
- 238000005260 corrosion Methods 0.000 title claims description 9
- 230000007797 corrosion Effects 0.000 title claims description 9
- 239000007864 aqueous solution Substances 0.000 title claims description 5
- 239000002184 metal Substances 0.000 title description 10
- 229910052751 metal Inorganic materials 0.000 title description 10
- -1 ferrous metals Chemical class 0.000 title description 6
- 150000007513 acids Chemical class 0.000 title description 5
- 230000001590 oxidative effect Effects 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000000243 solution Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000011260 aqueous acid Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- CVFVGPVYIWNTJB-UHFFFAOYSA-N 1-prop-2-ynylcyclohexan-1-ol Chemical group C#CCC1(O)CCCCC1 CVFVGPVYIWNTJB-UHFFFAOYSA-N 0.000 description 2
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- NFBVHCPRWIEACF-UHFFFAOYSA-N 1-prop-2-ynylcyclopentan-1-ol Chemical group C#CCC1(O)CCCC1 NFBVHCPRWIEACF-UHFFFAOYSA-N 0.000 description 1
- QZVDGMCFHKNWNV-UHFFFAOYSA-N 2-(4-chlorophenyl)pent-4-yn-2-ol Chemical group C#CCC(O)(C)C1=CC=C(Cl)C=C1 QZVDGMCFHKNWNV-UHFFFAOYSA-N 0.000 description 1
- DPZSISAWBIQWLF-UHFFFAOYSA-N 4-methylhept-1-yn-4-ol Chemical group CCCC(C)(O)CC#C DPZSISAWBIQWLF-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- LYXYBSYXGARUEA-UHFFFAOYSA-N hept-1-yn-4-ol Chemical group CCCC(O)CC#C LYXYBSYXGARUEA-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
- C23G1/00—Cleaning or pickling metallic material with solutions or molten salts
- C23G1/02—Cleaning or pickling metallic material with solutions or molten salts with acid solutions
- C23G1/04—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors
- C23G1/06—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors organic inhibitors
- C23G1/068—Cleaning or pickling metallic material with solutions or molten salts with acid solutions using inhibitors organic inhibitors compounds containing a C=C bond
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S507/00—Earth boring, well treating, and oil field chemistry
- Y10S507/939—Corrosion inhibitor
Definitions
- This invention relates to corrosion inhibitors for use in aqueous solutions of non-oxidizing acids to inhibit the corrosion of ferrous metals by such acids.
- the inhibitors of the invention are acetylenic alcohols corresponding to the formula R CHEC-CHrJl-OH wherein the R substituents together contain 4 to 12 carbon atoms and are independently Selected from the group consisting of hydrogen, alkyl radicals containing 1 to 8 carbon atoms and which may be joined together to form a cycloalkyl ring containing 5 to 6 carbon atoms, phenyl and chlorophenyl radicals.
- an acetylenic alcohol corresponding to the above formula is dissolved or dispersed in the acid the corrosive action of which is to be inhibited.
- aqueous acid we mean a composition comprising acid and water and do not mean to exclude the presence of other substances.
- ferrous metals we mean iron, steel, stainless steel and, in general, any metal comprising a major proportion of iron.
- the inhibitors of the invention are effective not only at ordinary temperatures but also at elevated temperatures. All are effective at 150 degrees and some at 200 degrees F. Moreover, they are effective in various concentrations of acids, even including hydrochloric acid up to 37 percent, that is, commercial concentrated acid.
- inhibitors are particularly useful include metal-pickling, cleaning and polishing baths, oil well-acidizing solutions, boiler-cleaning compositions and the like.
- the inhibitors of this invention are either commercially available or are easily made from commercially available intermediates.
- the alcohols are easily prepared from propargyl bromide and the appropriate carbonyl compound by well known methods, such as that of Henbest et al., J. Chem. Soc., 1949, 2696-2700.
- the inhibitor When the inhibitor is not completely soluble in the aqueous acid in which it is to be used, as when the compounds of Examples 3-6 are desired to be used in amounts exceeding their solubility, it is usually advantageous to incorporate into the inhibitor-acid mixture a small amount of a suitable surfactant whereby the inhibitor is solubilized and/ or dispersed in the acid, thereby greatly increasing its effectiveness.
- a suitable surfactant are those that are stable in acid media under the conditions of use, the non-ionic surfactants being preferred for this reason.
- An aqueous solution of a non-oxidizing acid containing an effective amount of a corrosion inhibitor consisting solely of a compound corresponding to the formula wherein the R substituents together contain 4 to 12 carbon atoms and are independently selected from the group consisting of hydrogen, phenyl, chlorophenyl, alkyl groups containing 1 to 8 carbon atoms each and parts of a cycloalkyl ring containing 5 to 6 carbon atoms.
- a solution as defined in claim 7 wherein the in hibitor is 4-methyl-1-heptyn-4-ol.
- a process for inhibiting the corrosion of ferrous metals in contact with aqueous non-oxidizing acid consisting essentially of maintaining in said acid an efiective amount of a corrosion inhibitor consisting solely of a compound as defined in claim 1.”
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General 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)
- Cleaning And De-Greasing Of Metallic Materials By Chemical Methods (AREA)
Description
United States Patent CORROSION INHIBITORS FOR FERROUS lVIETALS t gunous SOLUTIONS OF NON-OXIDIZING Charles T. Pumpelly and Joseph L. Wasco, Midland,
Mich., assignors to The Dow Chemical Company, Midland, Mich., a corporation of Delaware No Drawing. Application December 28, 1956 Serial No. 631,045
14 Claims. (Cl. 252-855) This invention relates to corrosion inhibitors for use in aqueous solutions of non-oxidizing acids to inhibit the corrosion of ferrous metals by such acids.
The inhibitors of the invention are acetylenic alcohols corresponding to the formula R CHEC-CHrJl-OH wherein the R substituents together contain 4 to 12 carbon atoms and are independently Selected from the group consisting of hydrogen, alkyl radicals containing 1 to 8 carbon atoms and which may be joined together to form a cycloalkyl ring containing 5 to 6 carbon atoms, phenyl and chlorophenyl radicals.
According to the invention an acetylenic alcohol corresponding to the above formula is dissolved or dispersed in the acid the corrosive action of which is to be inhibited.
By aqueous acid we mean a composition comprising acid and water and do not mean to exclude the presence of other substances. By ferrous metals we mean iron, steel, stainless steel and, in general, any metal comprising a major proportion of iron.
Only a small amount of the inhibitor is needed. As little as a few thousandths of 1 percent, based on the aqueous acid, significantly reduces the corrosion of ferrous metals exposed to the acid. The degree of inhibition increases with the concentration of the inhibitor up to a level of about 1 percent. Beyond this point little added protection of the metal is obtained by the use of more inhibitor. We generally prefer to use our inhibitors at a level of about 0.1 to 0.4 percent, this amount being adequate for most purposes.
The inhibitors of the invention are effective not only at ordinary temperatures but also at elevated temperatures. All are effective at 150 degrees and some at 200 degrees F. Moreover, they are effective in various concentrations of acids, even including hydrochloric acid up to 37 percent, that is, commercial concentrated acid.
Applications in which the inhibitors are particularly useful include metal-pickling, cleaning and polishing baths, oil well-acidizing solutions, boiler-cleaning compositions and the like.
The inhibitors of this invention are either commercially available or are easily made from commercially available intermediates.
The alcohols are easily prepared from propargyl bromide and the appropriate carbonyl compound by well known methods, such as that of Henbest et al., J. Chem. Soc., 1949, 2696-2700.
In order to demonstrate the effectiveness of our inhibitors, a series of tests was run in which 0.4 percent of the inhibitor was put into a 10 percent aqueous solution of hydrochloric acid held at 150 degrees F. and a coupon of the metal to be tested was suspended in the solution for 16 hours. Thereafter the coupon was 2,913,408 Patented Nov. 17, 1959 cleaned, dried and weighed to determine the amount of metal dissolved by the acid. The results obtained in a series of such tests in which mild steel was used are shown in the following table.
a In the inhibitors of Examples 7 and 8 the 2 R's are joined to form cyclohexyl and eyclopentyl groups, respectively.
Results similar to those shown in the above table are obtained when other non-oxidizing acids, such as sulfuric, phosphoric and acetic acid, are used instead of hydrochloric acid; when other concentrations of the acid up to the commercial concentrated acid (37 percent) are used; and when other ferrous metals are used instead of mild steel. The inhibitors are also effective at elevated temperatures up to about degrees F.
When the inhibitor is not completely soluble in the aqueous acid in which it is to be used, as when the compounds of Examples 3-6 are desired to be used in amounts exceeding their solubility, it is usually advantageous to incorporate into the inhibitor-acid mixture a small amount of a suitable surfactant whereby the inhibitor is solubilized and/ or dispersed in the acid, thereby greatly increasing its effectiveness. In general, the suitable surfactants are those that are stable in acid media under the conditions of use, the non-ionic surfactants being preferred for this reason.
We claim:
1. An aqueous solution of a non-oxidizing acid containing an effective amount of a corrosion inhibitor consisting solely of a compound corresponding to the formula wherein the R substituents together contain 4 to 12 carbon atoms and are independently selected from the group consisting of hydrogen, phenyl, chlorophenyl, alkyl groups containing 1 to 8 carbon atoms each and parts of a cycloalkyl ring containing 5 to 6 carbon atoms.
2. A solution as defined in claim 1 wherein at least one of the R groups is an alkyl group.
3. A solution as defined in claim 1 wherein the two R substituents are joined to form a cycloalkyl group.
4. A solution as defined in claim 1 wherein the inhibitor is 2-(p-chlorophenyl)-4-pentyn-2-ol.
5. A solution as defined in claim 1 wherein the acid is hydrochloric acid.
6. solution as defined in claim 2 wherein one R is a I i 1 hydrogen and the other is an alkyl group.
7. A solution as defined in claim 2 wherein both R groups are alkyl groups. p
8. A solution as defined in claim 3 wherein the inhibitor is 1-(2-propynyl)cyclohexanol.
9. A solution as defined in claim 3 whereinthe-im hibitor is 1-(2-propynyl)cyclopentanol.
10. A solution as defined in claim 6 wherein the inhibitor is 1-heptyn-4-ol.
11. A solution as defined in claim 7 wherein the in hibitor is 4-methyl-1-heptyn-4-ol.
12. A process for inhibiting the corrosion of ferrous metals in contact with aqueous non-oxidizing acid, said process consisting essentially of maintaining in said acid an efiective amount of a corrosion inhibitor consisting solely of a compound as defined in claim 1."
4 t 13. A process as defined in claim 12 wherein the inhibitor is 1-(2-propynyl)cyclohexanol.
14. A process as defined in claim 13 wherein the acid is hydrochloric acid.
References Cited in the file of this patent 'UNITED STATES PATENTS Mascre May 30, 1939 2,204,597 Humphreys et a1. June 18,1940 2,355,599 Walker Aug. 8, 1944 "2,474,603 Viles et a1. June 28, 1949 2,564,757 Glasebrook Aug. 21, 1951 2,603,622 Berger July 15, 1952 2,806,067 Monroe et al. Sept. 10, 1957 2,814,593
Beiswanger et al. Nov. 26, 1957
Claims (1)
1. AN AQUEOUS SOLUTION OF A NON-OXIDIZING ACID CONCTAINING AN EFFECTIVE AMOUNT OF A CORROSION INHIBITOR CONSISTING SOLELY OF A COMPOUND CORRSPONDING TO THE FORMULA
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US631045A US2913408A (en) | 1956-12-28 | 1956-12-28 | Corrosion inhibitors for ferrous metals in aqueous solutions of non-oxidizing acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US631045A US2913408A (en) | 1956-12-28 | 1956-12-28 | Corrosion inhibitors for ferrous metals in aqueous solutions of non-oxidizing acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2913408A true US2913408A (en) | 1959-11-17 |
Family
ID=24529548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US631045A Expired - Lifetime US2913408A (en) | 1956-12-28 | 1956-12-28 | Corrosion inhibitors for ferrous metals in aqueous solutions of non-oxidizing acids |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2913408A (en) |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2975125A (en) * | 1957-03-01 | 1961-03-14 | Amchem Prod | Inhibitor compositions |
| US3047511A (en) * | 1959-08-24 | 1962-07-31 | Dow Chemical Co | Mineral acid inhibitor |
| US3049496A (en) * | 1959-04-30 | 1962-08-14 | Dow Chemical Co | Propargyl compounds as corrosion inhibitors |
| US3077454A (en) * | 1960-07-14 | 1963-02-12 | Dow Chemical Co | Compositions for inhibiting corrosion |
| US3077453A (en) * | 1961-09-01 | 1963-02-12 | Dow Chemical Co | Corrosion inhibition |
| US3079345A (en) * | 1959-04-30 | 1963-02-26 | Dow Chemical Co | Propargyl compounds as corrosion inhibitors |
| US3095381A (en) * | 1959-08-28 | 1963-06-25 | Air Reduction | Cleaning compositions |
| US3107221A (en) * | 1958-04-18 | 1963-10-15 | Dow Chemical Co | Corrosion inhibitor composition |
| US3108069A (en) * | 1961-01-26 | 1963-10-22 | Dow Chemical Co | Ethynyl compounds for use in the inhibition of silicate swelling |
| US3231507A (en) * | 1960-04-21 | 1966-01-25 | Dow Chemical Co | Corrosion inhibitors for aqueous acids |
| US3249548A (en) * | 1958-10-31 | 1966-05-03 | Cumberland Chemical Corp | Corrosion inhibiting composition comprising 4-ethyl-1-octyn-3-ol |
| US3979311A (en) * | 1974-05-30 | 1976-09-07 | Universal Oil Products Company | Corrosion inhibitor compositions |
| US4039336A (en) * | 1975-12-03 | 1977-08-02 | Exxon Research And Engineering Company | Diacetylenic alcohol corrosion inhibitors |
| WO2017066571A1 (en) | 2015-10-15 | 2017-04-20 | Agios Pharmaceuticals, Inc. | Combination therapy for treating malignancies |
| WO2020092894A1 (en) | 2018-11-02 | 2020-05-07 | Celgene Corporation | Solid forms of 2-methyl-1-[(4-[6-(trifluoromethyl) pyridin-2-yl]-6-{[2-(trifluoromethyl)pyridin-4-yl]amino}-1,3,5-triazin-2-yl) amino]propan-2-ol |
| EP3692983A1 (en) | 2008-05-15 | 2020-08-12 | Celgene Corporation | Oral formulations of cytidine analogs and methods of use thereof |
| US11591511B2 (en) | 2018-05-11 | 2023-02-28 | Fluid Energy Group Ltd | Methods for stimulating a hydrocarbon-bearing formation by perforating a wellbore and introducing and acidic composition in the wellbore |
| US12241021B2 (en) | 2018-05-11 | 2025-03-04 | Dorf Ketal Chemicals Fze | Method for fracking of simulation of hydrocarbon bearing formation |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2160406A (en) * | 1939-04-29 | 1939-05-30 | Lambiotte Freres Ets | Product for inhibiting the attack on metals by acids or salts and its applications |
| US2204597A (en) * | 1937-02-23 | 1940-06-18 | Standard Oil Co | Compounded lubricant |
| US2355599A (en) * | 1941-01-23 | 1944-08-08 | Du Pont | Acid metal treating baths |
| US2474603A (en) * | 1946-12-20 | 1949-06-28 | Standard Oil Dev Co | Inhibition of corrosion in wells |
| US2564757A (en) * | 1950-06-03 | 1951-08-21 | Hercules Powder Co Ltd | Corrosion inhibitor composition |
| US2603622A (en) * | 1948-10-01 | 1952-07-15 | Berger Heinrich | Halogen containing resin stabilized with an acetylene alcohol |
| US2806067A (en) * | 1956-08-02 | 1957-09-10 | Dow Chemical Co | Alpha-ethynyl-2, 4, 6-trimethyl-3-cyclohexene-1-methanol |
| US2814593A (en) * | 1953-12-18 | 1957-11-26 | Gen Aniline & Film Corp | Corrosion inhibition |
-
1956
- 1956-12-28 US US631045A patent/US2913408A/en not_active Expired - Lifetime
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2204597A (en) * | 1937-02-23 | 1940-06-18 | Standard Oil Co | Compounded lubricant |
| US2160406A (en) * | 1939-04-29 | 1939-05-30 | Lambiotte Freres Ets | Product for inhibiting the attack on metals by acids or salts and its applications |
| US2355599A (en) * | 1941-01-23 | 1944-08-08 | Du Pont | Acid metal treating baths |
| US2474603A (en) * | 1946-12-20 | 1949-06-28 | Standard Oil Dev Co | Inhibition of corrosion in wells |
| US2603622A (en) * | 1948-10-01 | 1952-07-15 | Berger Heinrich | Halogen containing resin stabilized with an acetylene alcohol |
| US2564757A (en) * | 1950-06-03 | 1951-08-21 | Hercules Powder Co Ltd | Corrosion inhibitor composition |
| US2814593A (en) * | 1953-12-18 | 1957-11-26 | Gen Aniline & Film Corp | Corrosion inhibition |
| US2806067A (en) * | 1956-08-02 | 1957-09-10 | Dow Chemical Co | Alpha-ethynyl-2, 4, 6-trimethyl-3-cyclohexene-1-methanol |
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2975125A (en) * | 1957-03-01 | 1961-03-14 | Amchem Prod | Inhibitor compositions |
| US3107221A (en) * | 1958-04-18 | 1963-10-15 | Dow Chemical Co | Corrosion inhibitor composition |
| US3249548A (en) * | 1958-10-31 | 1966-05-03 | Cumberland Chemical Corp | Corrosion inhibiting composition comprising 4-ethyl-1-octyn-3-ol |
| US3079345A (en) * | 1959-04-30 | 1963-02-26 | Dow Chemical Co | Propargyl compounds as corrosion inhibitors |
| US3049496A (en) * | 1959-04-30 | 1962-08-14 | Dow Chemical Co | Propargyl compounds as corrosion inhibitors |
| US3047511A (en) * | 1959-08-24 | 1962-07-31 | Dow Chemical Co | Mineral acid inhibitor |
| US3095381A (en) * | 1959-08-28 | 1963-06-25 | Air Reduction | Cleaning compositions |
| US3231507A (en) * | 1960-04-21 | 1966-01-25 | Dow Chemical Co | Corrosion inhibitors for aqueous acids |
| US3077454A (en) * | 1960-07-14 | 1963-02-12 | Dow Chemical Co | Compositions for inhibiting corrosion |
| US3108069A (en) * | 1961-01-26 | 1963-10-22 | Dow Chemical Co | Ethynyl compounds for use in the inhibition of silicate swelling |
| US3077453A (en) * | 1961-09-01 | 1963-02-12 | Dow Chemical Co | Corrosion inhibition |
| US3979311A (en) * | 1974-05-30 | 1976-09-07 | Universal Oil Products Company | Corrosion inhibitor compositions |
| US4039336A (en) * | 1975-12-03 | 1977-08-02 | Exxon Research And Engineering Company | Diacetylenic alcohol corrosion inhibitors |
| EP3692983A1 (en) | 2008-05-15 | 2020-08-12 | Celgene Corporation | Oral formulations of cytidine analogs and methods of use thereof |
| EP3782612A1 (en) | 2008-05-15 | 2021-02-24 | Celgene Corporation | Oral formulations of cytidine analogs and methods of use thereof |
| WO2017066571A1 (en) | 2015-10-15 | 2017-04-20 | Agios Pharmaceuticals, Inc. | Combination therapy for treating malignancies |
| US11591511B2 (en) | 2018-05-11 | 2023-02-28 | Fluid Energy Group Ltd | Methods for stimulating a hydrocarbon-bearing formation by perforating a wellbore and introducing and acidic composition in the wellbore |
| US12018210B2 (en) | 2018-05-11 | 2024-06-25 | Dorf Ketal Chemicals Fze | Methods for stimulating a hydrocarbon-bearing formation by perforating a wellbore and introducing an acidic composition in the wellbore |
| US12241021B2 (en) | 2018-05-11 | 2025-03-04 | Dorf Ketal Chemicals Fze | Method for fracking of simulation of hydrocarbon bearing formation |
| US12497557B2 (en) | 2018-05-11 | 2025-12-16 | Dorf Ketal Chemicals Fze | Methods for stimulating a hydrocarbon-bearing formation by perforating a wellbore and introducing an acidic composition in the wellbore |
| WO2020092894A1 (en) | 2018-11-02 | 2020-05-07 | Celgene Corporation | Solid forms of 2-methyl-1-[(4-[6-(trifluoromethyl) pyridin-2-yl]-6-{[2-(trifluoromethyl)pyridin-4-yl]amino}-1,3,5-triazin-2-yl) amino]propan-2-ol |
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