GB2104897A - Corrosion inhibitors - Google Patents
Corrosion inhibitors Download PDFInfo
- Publication number
- GB2104897A GB2104897A GB08125205A GB8125205A GB2104897A GB 2104897 A GB2104897 A GB 2104897A GB 08125205 A GB08125205 A GB 08125205A GB 8125205 A GB8125205 A GB 8125205A GB 2104897 A GB2104897 A GB 2104897A
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- United Kingdom
- Prior art keywords
- formula
- amino
- composition
- amide
- piperazine
- 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.)
- Granted
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- 238000005260 corrosion Methods 0.000 title claims abstract description 37
- 230000007797 corrosion Effects 0.000 title claims abstract description 37
- 239000003112 inhibitor Substances 0.000 title claims abstract description 26
- -1 ferrous metals Chemical class 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 20
- XPXMKIXDFWLRAA-UHFFFAOYSA-N hydrazinide Chemical compound [NH-]N XPXMKIXDFWLRAA-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 13
- 239000010452 phosphate Substances 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 8
- 239000012267 brine Substances 0.000 claims abstract description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims abstract description 8
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract description 7
- 229910052751 metal Inorganic materials 0.000 claims abstract description 6
- 239000002184 metal Substances 0.000 claims abstract description 6
- 230000000865 phosphorylative effect Effects 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 8
- 239000000194 fatty acid Substances 0.000 claims description 8
- 229930195729 fatty acid Natural products 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000004665 fatty acids Chemical class 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 3
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical group NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 claims description 3
- 239000003849 aromatic solvent Substances 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 235000011007 phosphoric acid Nutrition 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 19
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 239000003921 oil Substances 0.000 description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 239000003350 kerosene Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 3
- 239000003784 tall oil Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000011280 coal tar Substances 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003129 oil well Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000008039 phosphoramides Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-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
- 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
- C23F11/167—Phosphorus-containing compounds
- C23F11/1673—Esters of phosphoric or thiophosphoric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650952—Six-membered rings having the nitrogen atoms in the positions 1 and 4
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/54—Compositions for in situ inhibition of corrosion in boreholes or wells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Health & Medical Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
Abstract
A corrosion inhibitor for ferrous metals in the presence of oil/brine mixtures is obtained by reacting together an aminoamide and a phosphate ester. The amino amide is derived from an amino alkyl piperazine and the phosphate ester is obtained by phosphorylating an aliphatic alcohol/alkylene oxide adduct. The corrosion inhibitor may be of formula (5) or (6): <IMAGE> wherein n, n1, are greater than or equal to one; R, R<1>, R<2>, R<3>, R<4> are hydrogen or alkyl; and X is -NR-(CR2)n-.
Description
SPECIFICATION
Improvements in or relating to corrosion inhibitors
This invention relates to corrosion inhibitors and is concerned with corrosion inhibitors suitable for use in the oil producing industry.
It is well known to use corrosion inhibiting agents in the oil industry for inhibiting corrosion in, for example, oil producing wells, pipelines, and storage tanks. In such environments, articles made of ferrous metals are subject to corrosion by, for example, hydrogen sulphide, carbon dioxide and other acidic materials emanating from corrosive oil well brines and it is known to introduce into the oil/brine mixture corrosion inhibitors to reduce metal corrosion. Hitherto, corrosion inhibitors based on amines and amine derivatives, particularly fatty imidazolines and fatty amines have long been known. Such conventional corrosion inhibitors do, however, have their limitations.
According to the present invention there is provided a composition of matter suitable for use as a corrosion inhibitor for ferrous metals in the presence of oil/brine mixtures which composition of matter is the product obtained by reacting together
(i) an amino amide derived from an amino alkyl piperazine and
(ii) a phosphate ester obtained by reacting together (a) an adduct of an aliphatic alcohol and an
alkylene oxide and (b) a phosphorylating agent.
The amino alkyl piperazine used in accordance with the present invention may be substituted or unsubstituted and may have the formula:
wherein X = [NR2-(CR2); Y = X or hydrogen or (CR2)nH; n = 1 or more; the groups R, which may be the same or different, are hydrogen or lower alkyl groups; and R' represents eight substituents on the carbon atoms of the piperazine ring which substituents may be the same or different and are hydrogen or lower alkyl groups. Preferred lower alkyl groups are methyl, propyl and butyl groups.
The amino alkyl piperazine may be converted into the desired amino amide by reaction with a suitable carboxylic acid or amide forming derivative thereof. Thus, for example, it may be reacted with a free fatty acid or with a fatty acid glyceride or other ester or with a fatty acid chloride. Typically, the amino amide has the formula.
wherein X, Y and R1 have the meanings given above and R2 is an aliphatic hydrocarbon chain containing from 12 to 20, preferably 1 6 to 18, carbon atoms.
The aliphatic alcohol/alkylene oxide adducts used in accordance with the present invention are quite conventional and are formed in known manner by condensing the alkylene oxide with the aliphatic alcohol (e.g. a primary alcohol) in the presence of a suitable catalyst and under suitable conditions of temperature and pressure. Typically, the adduct has the formula:
wherein R3 is an aliphatic chain containing from 12 to 1 5 carbon atoms, R4 is hydrogen or lower alkyl, and n, is from 1 to 1 5, preferably 3 to 5.
The phosphorylating agent used for reaction with the adduct to form the phosphate ester is quite conventional and may be, for example, a polyphosphoric acid, phosphorus pentoxide, or orthophosphoric acid and typically the phosphate ester has the formula:
wherein R3, R4 and n, have the meanings specified above.
In one embodiment, the corrosion inhibitor of the invention is a salt of the amino amide and the phosphate ester and typical examples of the salt have the formula:
wherein R', R2, R3 R4, n1 and X have the meanings specified above.
In an alternative embodiment, the corrosion inhibitor of the invention is the corresponding phosphoramidate and typical examples of this embodiment have the formula:
wherein R', R2, R3 R4, X and n, have the meanings above specified.
Ordinarily, the residual amino amide present in the composition of the present invention is completely neutralised with glacial acetic acid in order that there is no precipitation on storage of the product. Generally, the product will be supplied in low cost aromatic solvents.
The following Examples illustrate the invention.
EXAMPLE 1
300 grm of a Tall Oil Fatty Acid (rosin content 4%) was reacted with 130 grm of amino ethyl piperazine (NH2. CH2 CH2 NC4H8NH). The water of reaction was allowed to distil off and the reaction temperature allowed to reach a maximum of 2200C which was held for 3 hours. The resultant fatty amino amide was then cooled to 500C and 200 grm of a phosphate ester based on a fatty alcohol ethoxylate was added in the presence of 260 grm of ethylene glycol monomethyl ether. The phosphate ester used was of Formula (4) wherein R3 was C12-C151 n1 was from 3 to 5; and R4 was hydrogen. The reaction mixture was held at 55"C for 1 hour.The resultant salt (Formula 5) was then dissolved in a coal tar solvent to give a final active content of 30% and was ready for use.
EXAMPLE 2
A mixture of 1 50 grm of a Tall Oil Fatty Acid and 1 50 grm of a petroleum oxidate was reacted with 130 grm of amino ethyl piperazine (NH2 CH2 CH2 NO4H8NH). The petroleum oxidate was that known as Texaco (registered Trade Mark) TC-8244 which consists primarily of organic acids and esters. The water of reaction was allowed to distil off and the reaction temperature allowed to reach a maximum of 220"C which was held for 3 hours. The resultant amino amide was then cooled to 50 C and 200 grm of a phosphate ester based on the fatty alcohol ethoxylate of Example 1 was added in the presence of 260 grm of ethylene glycol monoethyl ether. The reaction mixture was held at 55 C for 1 hour.The resultant salt (Formula 5) was dissolved in a coal tar solvent to give a final active content of approximately 30%. The product was ready for use.
EXAMPLE 3
Example 1 was repeated but in this case the fatty amino amide and the phosphate ester were reacted at 100 to 1 2000 instead of 50 C. This resulted in the formation of the corresponding phosphoramidate (Formula 6) instead of the salt (Formula 5).
EXAMPLE 4
Example 2 was repeated but in this case the amino amide and the phosphate ester were reacted at 100 to 120"C instead of 500C. This resulted in the formation of the corresponding phosphoramidate (Formula 6) instead of the salt (Formula 5).
The salts (Formulae 5) obtained in accordance with Examples 1 and 2 were tested for their corrosion inhibiting properties in a synthetic crude oil environment against two currently used corrosion inhibitors viz. Inhibitor A (which was an ethoxylated phosphoramide of the type described in U.S. Patent No. 3,584,008) and Inhibitor B (which was a fatty imidazoline based on tall oil fatty acid and diethylene triamine.
In these tests, mild steel coupons enclosed within bottles containing a synthetic oil medium were slowly rotated under controlled conditions and the effect of varying levels of corrosion inhibitors were recorded visually by observing the amount of corrosion on each coupon. This simulates a continuous injection treatment. The synthetic oil medium consisted of a blend of Kerosene and a synthetic brine solution. For 'sour' conditions both phases were saturated with hydrogen sulphide and for 'sweet' conditions with carbon dioxide. The composition of the synthetic brine was as follows:- Sodium Chloride 4.2%
Calcium Chloride 1.4%
Sodium Sulphate 0.1%
Magnesium Chloride 1.7%
Demineralised water 92.6%
The attitudes of the coupons in the bottles were such that the coupons repeatedly passed through both liquid phases of the synthetic oil mixture.In each case the corrosion inhibitor under test (diluted to 25% active solids in a suitable aromatic solvent) was introduced by means of a pipette into the kerosene phase of the synthetic oil medium.
Each test was in three parts viz. the coating cycle, the rinsing cycle and the corrosion cycle.
THE COATING CYCLE
The inhibitor under test was introduced into the synthetic oil medium as previously described and the bottle was rotated for 4 hours. After this period the coupon was removed from the bottle and examined for corrosion.
THE RINSING CYCLE
The coupon was then fixed into a bottle containing untreated synthetic oil medium and then rotated for 1 hour. After this period the coupon was removed from the bottle and examined for corrosion.
THE CORROSION CYCLE
The inhibitor under test was introduced into a fresh synthetic oil medium at a level intended to reflect the dosage used in continuous injection treatment. The coupon was then firmly fixed into the bottle which was rotated as before. The coupon was visually examined at intervals of 5 hours and the extent of corrosion recorded.
The results obtained are set out in Tables I and II.
TABLE 1 'Sweet' conditions (ratio of Kerosene/Brine-50/50)
COATING CYCLE RINSING CYCLE CORROSION CYCLE % CORROSION PRODUCT ACTIVE DOSAGE % DOSAGE % DOSAGE 5 10 15 20 REF. CONC. ppm CORROSION ppm CORROSION ppm hrs hrs hrs hrs Example 1 25% 200 0 0 0 50 0 0 0 10 Example 2 25% 200 0 0 0 50 0 0 0 0 Inhibitor A 25% 200 0 0 0 50 0 0 10 25 Inhibitor B 25% 200 0 0 0 50 0 10 25 35 TABLE 2 'Sour' conditions (ratio of Kerosene/Brine - 50/50)
COATING CYCLE RINSING CYCLE CORROSION CYCLE % CORROSION PRODUCT ACTIVE DOSAGE % DOSAGE % DOSAGE 5 10 15 20 REF. CONC. ppm CORROSION ppm CORROSION ppm hrs hrs hrs hrs Example 1 25% 200 0 0 0 50 0 0 10 20 Example 2 25% 200 0 0 0 50 0 0 0 5 Inhibitor A 25% 200 0 0 0 50 0 10 25 35 Inhibitor B 25% 200 0 0 5 50 10 20 40 65 It can be seen that the compositions of the invention have better corrosion inhibiting properties than the conventional inhibitors.
Claims (22)
1. A method of manufacturing a composition of matter suitable for use as a corrosion inhibitor for ferrous metals in the presence of oil/brine mixtures, which method comprises reacting together
(i) an amino amide derived from an amino alkyl piperazine and
(ii) a phosphate ester obtained by reaction together (a) an adduct of an aliphatic alcohol and an
alkylene oxide and (b) a phosphorylating agent.
2. A method according to claim 1 wherein the amino alkyl piperazine has the formula:
wherein X = NR2-(CR2); Y = X or hydrogen or (CR2)nH; n = 1 or more; the groups R, which may be the same or different, are hydrogen or lower alkyl groups; and R' represents eight substituents on the carbon atoms of the piperazine ring which substituents may be the same or different and are hydrogen or lower alkyl groups.
3. A method according to claim 2 wherein R and R' are methyl, propyl or butyl groups.
4. A method according to claim 2 wherein the amino alkyl piperazine is amino ethyl piperazine.
5. A method according to any one of claims 1 to 4 wherein the amino alkyl piperazine is converted into the desired amino amide by reaction with a carboxylic acid or amide forming derivative thereof.
6. A method according to claim 5 wherein the carboxylic acid is a fatty acid.
7. A method according to claim 5 wherein the amide forming derivative is a fatty acid glyceride or other ester or a fatty acid chloride.
8. A method according to any one of the preceding claims wherein the amino amide has the formula:
wherein X, Y and R1 have the meanings given above and R2 is an aliphatic hydrocarbon chain containing from 12 to 20 carbon atoms.
9. A method according to claim 8 wherein R2 is an aliphatic hydrocarbon chain containing from 1 6 to 18 carbon atoms.
10. A method according to any one of the preceding claims wherein the aliphatic alcohol/alkylene oxide adduct is formed by condensing together an alkylene oxide with an aliphatic primary alcohol.
11. A method according to any one of the preceding claims wherein the aliphatic alcohol/alkylene oxide adduct has the formula:
wherein R3 is an aliphatic chain containing from 1 2 to 1 5 carbon atoms, R4 is hydrogen or lower alkyl, and n1 is from 1 to 15.
12. A method according to claim 11 wherein, in the formula, n, is from 3 to 5.
1 3. A method according to any one of the preceding claims wherein the phosphorylating aent is a polyphosphoric acid, phosphorus pentoxide, or orthophosphoric acid.
14. A method according to any one of the preceding claims wherein the phosphate ester has the formula:
wherein R3, R4 and n, have the meanings specified above.
1 5. A method according to any one of the preceding claims and including the additional step of neutralising residual amino amide present in the composition.
1 6. A method according to claim 1 5 wherein the residual amino amide is neutralised with acetic acid.
1 7. A method according to any one of the preceding claims and including the additional step of dissolving the composition in an aromatic solvent.
18. A method according to claim 1 substantially as hereinbefore described in any one of Examples 1 to4.
19. A composition of matter whenever obtained by the method claimed in any one of the preceding claims.
20. A composition of matter which is a salt having the formula:
wherein R', R2, R3, R4, n1 and X have the meanings specified above.
21. A composition of matter which is a phosphoramidate having the formula:
wherein R1, R2, R3, R4, X and n1 have the meanings above specified.
22. The use of a composition of matter as claimed in any one of claims 19 to 21 as a corrosion inhibitor for ferrous metals in the presence of oil/brine mixtures.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08125205A GB2104897B (en) | 1981-08-18 | 1981-08-18 | Corrosion inhibitors |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08125205A GB2104897B (en) | 1981-08-18 | 1981-08-18 | Corrosion inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2104897A true GB2104897A (en) | 1983-03-16 |
| GB2104897B GB2104897B (en) | 1985-01-30 |
Family
ID=10524019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08125205A Expired GB2104897B (en) | 1981-08-18 | 1981-08-18 | Corrosion inhibitors |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2104897B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0567212A1 (en) * | 1992-04-21 | 1993-10-27 | Petrolite Corporation | The reaction product of nitrogen bases and phosphate esters as corrosion inhibitors |
| US5393464A (en) * | 1993-11-02 | 1995-02-28 | Martin; Richard L. | Biodegradable corrosion inhibitors of low toxicity |
| WO2006120694A1 (en) | 2005-05-13 | 2006-11-16 | Anil Kelkar | Organic compound and process for inhibiting corrosion on metals |
-
1981
- 1981-08-18 GB GB08125205A patent/GB2104897B/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0567212A1 (en) * | 1992-04-21 | 1993-10-27 | Petrolite Corporation | The reaction product of nitrogen bases and phosphate esters as corrosion inhibitors |
| US5380466A (en) * | 1992-04-21 | 1995-01-10 | Petrolite Corporation | Reaction product of nitrogen bases and phosphate esters as corrosion inhibitors |
| USRE36291E (en) * | 1992-04-21 | 1999-09-07 | Baker Hughes Incorporated | Reaction product of nitrogen bases and phosphate esters as corrosion inhibitors |
| US5393464A (en) * | 1993-11-02 | 1995-02-28 | Martin; Richard L. | Biodegradable corrosion inhibitors of low toxicity |
| US5785895A (en) * | 1993-11-02 | 1998-07-28 | Petrolite Corporation | Biodegradable corrosion inhibitors of low toxicity |
| WO2006120694A1 (en) | 2005-05-13 | 2006-11-16 | Anil Kelkar | Organic compound and process for inhibiting corrosion on metals |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2104897B (en) | 1985-01-30 |
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| PCNP | Patent ceased through non-payment of renewal fee |