CN1068565A - Preparation method of alkynyloxymethylamine and quaternary ammonium salt thereof and corrosion inhibitor - Google Patents
Preparation method of alkynyloxymethylamine and quaternary ammonium salt thereof and corrosion inhibitor Download PDFInfo
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- CN1068565A CN1068565A CN 92106258 CN92106258A CN1068565A CN 1068565 A CN1068565 A CN 1068565A CN 92106258 CN92106258 CN 92106258 CN 92106258 A CN92106258 A CN 92106258A CN 1068565 A CN1068565 A CN 1068565A
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- quaternary ammonium
- methylamine
- alkynes oxygen
- ethanol
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- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims abstract description 11
- 239000003112 inhibitor Substances 0.000 title claims abstract description 7
- 230000007797 corrosion Effects 0.000 title abstract description 20
- 238000005260 corrosion Methods 0.000 title abstract description 20
- 238000002360 preparation method Methods 0.000 title description 4
- 238000000034 method Methods 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 238000003756 stirring Methods 0.000 claims abstract description 7
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims abstract description 3
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract 2
- 239000003899 bactericide agent Substances 0.000 claims abstract 2
- 230000015572 biosynthetic process Effects 0.000 claims abstract 2
- 238000003786 synthesis reaction Methods 0.000 claims abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
- IUPDNGMVUVUNNH-UHFFFAOYSA-N methanamine;oxygen Chemical compound [O].NC IUPDNGMVUVUNNH-UHFFFAOYSA-N 0.000 claims description 29
- 150000001345 alkine derivatives Chemical class 0.000 claims description 21
- -1 propine methyl alkyl amine Chemical class 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 9
- 238000010189 synthetic method Methods 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- 150000001350 alkyl halides Chemical class 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000002131 composite material Substances 0.000 claims description 3
- 239000006185 dispersion Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 238000005660 chlorination reaction Methods 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000011874 heated mixture Substances 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 239000012258 stirred mixture Substances 0.000 claims description 2
- 239000012747 synergistic agent Substances 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 22
- 230000005764 inhibitory process Effects 0.000 abstract description 11
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 5
- 238000010438 heat treatment Methods 0.000 abstract description 3
- 230000002378 acidificating effect Effects 0.000 abstract description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- VKFAUCPBMAGVRG-UHFFFAOYSA-N dipivefrin hydrochloride Chemical compound [Cl-].C[NH2+]CC(O)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1 VKFAUCPBMAGVRG-UHFFFAOYSA-N 0.000 description 10
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 9
- 229930040373 Paraformaldehyde Natural products 0.000 description 8
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 8
- 229940073608 benzyl chloride Drugs 0.000 description 8
- 229920002866 paraformaldehyde Polymers 0.000 description 8
- 230000000116 mitigating effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 231100000572 poisoning Toxicity 0.000 description 2
- 230000000607 poisoning effect Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- 241000208340 Araliaceae Species 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000000274 adsorptive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002461 imidazolidines Chemical class 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000837 restrainer Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
Abstract
A method for preparing alkynyloxymethylamine and quaternary ammonium salt thereof adopts a mode of direct synthesis by heating and stirring, and the reaction formulas are respectively as follows:
the compound components of the product are as follows:
alkynyloxymethylamines alkynyloxymethylbenzylammonium chloride
15～30 15～30
Bactericide ethanol water
5-1040-605-10 of the acidic medium corrosion inhibitor has the advantages of simple production process, low cost and good corrosion inhibition effect.
Description
The present invention relates to chemical field, specifically just provided the manufacture method of a kind of alkynes oxygen methylamine and quaternary ammonium salt thereof, reaching with it is the acid inhibitor of major ingredient preparation.
In recent years, in petroleum industry in order further to improve oil and gas production, reduce production costs, make full use of the underground oil and gas resource, increase economic efficiency, the exploitation in oil field develops towards deep-well high temperature and secondary and tertiary oil recovery direction, adopting concentrated hydrochloric acid (or mud acid) fracture acidizing to handle is that an effective volume increase joint props up the great technical measures of utilizing resource more fully, and this measure only could realize under the inhibiter condition that has extremely strong inhibition metallic corrosion effect under the High Temperature High Pressure concentrated acid condition developing, present widely used acid inhibitor, adopt has the intramolecularly of absorption and complexing action to contain N more, O, S, carboxyl, the organism of sulfydryl and ginseng key.As organic amine, tetrahydroglyoxaline, acid amides, thiocarbamide, heterocyclic ketone, committee's ammonium salt, natural organic matter and some inorganics, corrosion mitigating effect is all not satisfactory.Alkynes oxyalkyl amine and alkynes oxyalkyl season ingot salt are the novel acid inhibitors that the late nineteen seventies early eighties grows up, with alkynes oxygen methylamine is example, alkynes oxygen methylamine is itself to have the alkylamine of the appropriate configuration of certain corrosion inhibition, alkynol and carbonyl compound, the more good new compound of performance that produces by condensation reaction.Promptly contain O in the compound; N active atomic group; easily produce chemistry and physical adsorption in the metallic surface; contain big towering key again; electronic cloud easily moves; be easy to generate adsorption; thereby improved greatly at ironing surface complex ability; strengthened adsorption; shown the corrosion inhibition that is better than independent organic amine and propiolic alcohol; in addition; alkynes oxygen methylamine also can be by precipitation; hydrogen bond and polymerization etc. act on the metallic surface and form protective membrane, add the suitable chain length of organic amine and the shielding effect that alkyl rose of structure, and alkynes oxygen methylamine has higher corrosion inhibition in acid and CO 2 medium.But the synthetic of alkynes oxygen methylamine normally adopts a certain amount of benzene to make the branch aqua in the document, by the backwash of certain hour, tells the theoretical water that reaction generates, and steams benzene then, reduces pressure and tells product.Because heated time is longer in the reaction process, can cause the polymerization of organism decomposition and acetylene bond, so yield is lower.Make the branch aqua with benzene on the other hand, can bring many troubles to synthetic operation, long as reaction time, can cause the loss (the benzene rate of recovery is 80%) of benzene in the operating process, production cost is increased.Benzene easily catches fire, and can increase the danger that industrialness is produced; Benzene is toxic substance to human body in addition, can cause environmental pollution.Quaternary ammonium salt is in acidic medium in general, corrosion inhibition and solubility property are better than organic amine, committee's ammonium compound can stop the infiltration of hydrogen atom to metal inside effectively, therefore have intensive and suppress the ability that steel produces hydrogen embrittlement, but also do not seen the report of relevant alkynoxide methyl quaternary ammonium salt at present.Particularly, be that the inhibiter of composite other compositions of major ingredient does not have research as yet with alkynes oxygen methylamine and committee's ammonium salt thereof.
The objective of the invention is to, a kind of method of producing alkynes oxygen methylamine and quaternary ammonium salt thereof at first is provided, make its operation more simple, and fundamentally eliminate in the operating process benzene to the murder by poisoning of human body and the industrial danger that is caused, institute's synthetic compound corrosion inhibition is also more superior simultaneously.Also will provide more than one to state synthetic compound in addition is main component, the comprehensive all more good inhibiter of use properties such as corrosion inhibition and solubility property.
The propine oxygen methyl alkyl amine molecule formula of the synthetic preparation of method provided by the invention is as follows:
Wherein R is a substituting group, as alkyl, cycloalkyl, aryl and substitutive derivative.Its synthetic concrete grammar is that formaldehyde and alkynol have been put into the backwash prolong, and in the reaction vessel of stirring motor and dropper, the heated and stirred mixture injects organic amine more gradually up to the beginning backwash, and its reaction formula is as follows:
The alkynes oxygen methyl alkyl amine that does not dewater and the haloalkane reaction that are gone out by method for preparing have generated alkynes oxygen methyl quaternary ammonium compounds, and molecular formula is:
Wherein R ' is alkyl, aryl etc., and X is a halogen atom, and concrete synthetic method is, alkynes oxygen methyl alkyl amine and haloalkane and ethanol are put into above-mentioned reactor jointly, and heated and stirred finally obtains reactant, and its reaction formula is as follows:
RN(CH
2OCH
2C≡CH)
2+
No matter be alkynes oxygen methylamine or its quaternary ammonium salt, increase, the adsorptive power of metallic surface is increased with carbonatoms in the alkylamine, and be adsorbed between the compound molecule of metallic surface gravitation also along with increasing, thereby corrosion mitigating effect raises gradually, but along with the increase of carbon amount, the compound dissolution degree is variation gradually, can cause the decline of corrosion inhibition rate, the quantity of general carbon is selected less than 14, and the best is 6-10, this kind alkynes oxygen methylamine and quaternary ammonium salt, raw material sources are convenient, moderate cost.When synthesizing quaternary ammonium salt, as adopting Benzyl Chloride C
6H
5CH
2Cl is as haloalkane, and its corrosion mitigating effect of alkynes oxygen methyl alkyl aryl ammonium chloride that synthesizes is the most obvious.
Inhibiter provided by the present invention, be by do not dewater alkynes oxygen methylamine and not dewatering and alcoholic acid alkynes oxygen methyl-benzyl ammonium chloride with the aforesaid method synthetic, sterilant (as DDB, bromogeramine, 1231 etc.), the second alcohol and water mixes, its component content following (weight percent)
Alkynes oxygen methylamine alkynes oxygen methyl-benzyl ammonium chloride
15～30 15～30
Sterilant ethanol water
5-10 40-60 5-10
If wherein the add-on of alkynes oxygen methylamine and alkynes oxygen methyl-benzyl ammonium chloride is less than 15%, corrosion mitigating effect is relatively poor, if add-on is crossed the solvability variation of polyyne oxygen methylamine, and corrosion mitigating effect improves little, becomes original from inhibiter and considers that two kinds of component maximum constraints are 30%, sterilant is except that playing germicidal action, also have the algae removal effect, ethanol occurs as solvent, also is defoamer and dispersion agent.
Inhibiter provided by the present invention can mix arbitrarily with various dispersion agents (benzene,toluene,xylene etc.) and solvent (ethanol, ethers etc.), can unite use with synergistic agent such as nitrogenous compounds such as quinoline, pyridine and quaternary ammonium salts thereof, further improve corrosion inhibition.Embodiment is described in detail in detail below:
Embodiment 1
With 60.0g(2.0mol) Paraformaldehyde 96 and 114.0g(2.0mol) propiolic alcohol, putting into volume is the three-necked flask that 250ml is equipped with backwash prolong stirring motor and dropping funnel.Heating and stir and answer mixture up to the beginning backwash.In 1.0～1.5 hours, splash into 59.0g(1.0mol) Isopropylamine, backwash a few hours, obtain product sec.-propyl two propine oxygen methylamine, its structure is:
Embodiment 2
Similarly in the method, 60.0g(2.0mol) Paraformaldehyde 96,114.0g(2.0mol) propiolic alcohol and 73.0g(1.0mol) the butylamine reaction, prepare the compound of following structure:
Embodiment 3
Similarly in the method, 60.0g(2.0mol) Paraformaldehyde 96,114.0g(2.0mol) propiolic alcohol and 99.2g(1.0mol) the hexahydroaniline reaction, prepare the compound of following structure
Embodiment 4
Similarly in the method, 60.0g(2.0mol) Paraformaldehyde 96,114.0g(2.0mol) propiolic alcohol and 102.2g(1mol) the normal hexyl Amine reaction, prepare the compound of following structure:
Embodiment 5
Similarly in the method, 60.0g(2.0mol) Paraformaldehyde 96,114.0g(2.0mol) propiolic alcohol and 129.3g(1mol) the octylame reaction, prepare the compound of following structure:
Embodiment 6
Similarly in the method, 60.0g(2.0mol) Paraformaldehyde 96,114.0g(2.0mol) propiolic alcohol and 157.3g(1mol) the decyl amine reaction, prepare the compound of following structure:
Embodiment 7
Similarly in the method, 60.0g(2.0mol) Paraformaldehyde 96,114.0g(2.0mol) propiolic alcohol and 185.4g(1mol) the amino dodecane reaction, prepare the compound of following structure:
Embodiment 8
Similarly in the method, 60.0g(2.0mol) Paraformaldehyde 96,114.0g(2.0mol) propiolic alcohol and 213.4g(1mol) the tetradecy lamine reaction, prepare the compound of following structure:
Embodiment 9
With 39g(0.2mol) sec.-propyl two propine oxygen methylamine, 25.5g(0.2mol) Benzyl Chloride and the ethanol of 30-100ml, put into volume and be 250 milliliters reflux condensing tube is housed, in the three-necked flask of stirring motor, the reacting by heating mixture, backwash 24 hours obtains product sec.-propyl two propine oxygen methyl-benzyl ammonium chlorides, and its structure is:
Embodiment 10
In the similar method, 31.4g(0.15mol) butyl two propine oxygen methylamine, 19.1g(0.15mol) chlorination is stuck in the 30-100ml ethanol and refluxed 24 hours, prepares the compound of following structure:
Embodiment 11
In the similar method, ring ethyl two propine oxygen methylamine 23.5g(0.1mol), Benzyl Chloride 12.8g(0.1mol) refluxed 48 hours in 30-100ml ethanol, prepared the compound of following structure:
Embodiment 12
In the similar method, n-hexyl two propine oxygen methylamine 23.7g(0.1mol), 12.8g(0.1mol) Benzyl Chloride refluxed 48 hours in 30-100ml ethanol, prepared the compound of following structure:
Embodiment 13
In the similar method, octyl group two propine oxygen methylamine 26.5g(0.1mol), Benzyl Chloride 12.8g(0.1mol) refluxed 60 hours in 30-100ml ethanol, prepared the compound of following structure:
Embodiment 14
In the similar method, 29.3g(0.1mol) ten alkyl, two propine oxygen methylamine, Benzyl Chloride 12.8g(0.1mol) refluxed 60 hours in 30-100ml ethanol, prepared the compound of following structure:
Embodiment 15
In the similar method, 32.1g(0.1mol) dodecyl two propine oxygen methylamine, Benzyl Chloride 12.8g(0.1mol) refluxed 60 hours in 30-100ml ethanol, was prepared as follows the compound of structure:
Embodiment 16
In the similar method, 35.0g(0.1mol) tetradecyl two propine oxygen methylamine, Benzyl Chloride 12.8g(0.1mol) refluxed 60 hours in 30-100ml ethanol, prepared the compound of following structure:
Embodiment 17
With content is 20% ring ethyl two propine oxygen methylamine, 20% ring ethyl two propine oxygen methyl-benzyl ammonium chlorides, and 10% fungicide 1227,6% water and 44% ethanol mix mutually, stir.
Embodiment 18
Implement 17 inhibiter that obtain, composite again pyridine quaternary ammonium salt and imidazolidine derivatives were with 2: 1: 1 mixed.
The corrosion inhibition of compound and inhibiter sees Table 1.
Table 2 is the corrosion test results of several inhibiter under acidulated condition.
In a word, the present invention has adopted the method for directly synthetic alkynes oxygen methylamine, make to divide aqua without benzene, need not from reaction product, tell the water that reaction generates, therefore the distillation of benzene and the vacuum distillation process of product have also been removed from, simplified operation, shortened the reaction times greatly, reduced production cost to a great extent, and eradicated murder by poisoning and pollution operator and environment.The alkynes oxygen methylamine that is regardless of water that synthesizes by the synthetic method of having simplified is quaternized synthesizes the quaternary ammonium salt that, removed the process that solvent is steamed in the decompression of revolution vaporizer in synthetic again from, promptly simplified synthetic operation, can further reduce production costs again to a certain extent.Inhibiter provided by the present invention is under similarity condition, and consumption is significantly less than the acid inhibitor of other type, and effect obviously is better than other type inhibiter.In addition, inhibiter provided by the present invention can also be as restrainers such as chemical industry equipment, boiler, heat exchanger, sewage disposals.
The corrosion test result of several inhibiter of table 2 under acidulated condition
Annotate: test conditions is 65 ℃, 4 hours, and normal pressure, N-80 steel
Claims (7)
1, a kind of synthetic method for preparing propine methyl alkyl amine, its molecular formula is:
Wherein R is a substituting group, as alkyl, cycloalkyl, aryl and substitutive derivative, it is characterized in that, concrete synthetic method is: formaldehyde and alkynol have been put into reflux condensing tube, in the reactor of stirring motor and dropper, the heated and stirred mixture injects organic amine more gradually up to beginning backflow, and reaction formula is as follows:
2, a kind of method of the propine methylamine synthesis of quaternary ammonium compounds of preparing with the described method of claim 1, it is characterized in that: the molecular formula of synthetics is
Wherein R ' is alkyl, aryl etc., and X is a halogen atom, and concrete synthetic method is: alkynes oxygen methyl alkyl alkanamine and haloalkane and ethanol are put into reactor jointly, and heated and stirred finally obtains reactant, and reaction formula is as follows:
RN(CH
2OCH
2C≡CH)
2+
3,, it is characterized in that the quantity of carbon in the substituent R is selected less than 14 by claim 1,2 described synthetic methods.
4,, it is characterized in that the quantity of carbon in the substituent R is selected to be preferably between 6～10 by the described synthetic method of claim 3.
5, by the described synthetic method of claim 2, it is characterized in that with chlorination card C
6H
5CH
2Cl is as haloalkane.
6, a kind of acid inhibitor, it is characterized in that inhibiter is made up of alkynes oxygen methylamine and alkynes oxygen methyl-benzyl ammonium chloride that right 1 and right 5 provide, composite bactericide (DDB, bromogeramine, 1231 etc.), the second alcohol and water, its concrete content following (weight percent): alkynes oxygen methylamine alkynes oxygen methyl-benzyl ammonium chloride
15～30 15～30
Sterilant ethanol water
5-10 40-60 5-10
7, by the described inhibiter of claim 6, it is characterized in that it can mix arbitrarily with various dispersion agents (benzene,toluene,xylene etc.) and solvent (ethanol, ethers etc.), also can unite use with synergistic agent such as nitrogenous compounds such as quinoline, pyridine and quaternary ammonium salts thereof.
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| CN92106258A CN1086381C (en) | 1992-06-18 | 1992-06-18 | Preparation method of alkynyloxymethylamine and quaternary ammonium salt thereof and corrosion inhibitor |
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| CN92106258A CN1086381C (en) | 1992-06-18 | 1992-06-18 | Preparation method of alkynyloxymethylamine and quaternary ammonium salt thereof and corrosion inhibitor |
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| CN1068565A true CN1068565A (en) | 1993-02-03 |
| CN1086381C CN1086381C (en) | 2002-06-19 |
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Cited By (8)
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| CN1296519C (en) * | 2004-03-26 | 2007-01-24 | 沈阳市铭阳防腐研究所 | Corrosion inhibitor anti corrosion of sulfureted hydrogen |
| CN101892042A (en) * | 2010-06-30 | 2010-11-24 | 中国海洋石油总公司 | High temperature acidizing corrosion inhibitor and preparation method thereof |
| CN101654303B (en) * | 2008-08-18 | 2011-05-04 | 天津大港油田科远石油工程有限责任公司 | Corrosion inhibitor suitable for complex wastewater of oilfield and preparation method thereof |
| CN102049213A (en) * | 2010-11-12 | 2011-05-11 | 西华师范大学 | Propargyl alcohol type quaternary ammonium salt surfactant and preparation method thereof |
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Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1015918B (en) * | 1988-06-23 | 1992-03-18 | 山东新华制药厂劳动服务公司 | Utilization of the colloidal by product from pyrazolong drugs |
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| CN1296519C (en) * | 2004-03-26 | 2007-01-24 | 沈阳市铭阳防腐研究所 | Corrosion inhibitor anti corrosion of sulfureted hydrogen |
| CN101654303B (en) * | 2008-08-18 | 2011-05-04 | 天津大港油田科远石油工程有限责任公司 | Corrosion inhibitor suitable for complex wastewater of oilfield and preparation method thereof |
| CN101892042A (en) * | 2010-06-30 | 2010-11-24 | 中国海洋石油总公司 | High temperature acidizing corrosion inhibitor and preparation method thereof |
| CN102049213A (en) * | 2010-11-12 | 2011-05-11 | 西华师范大学 | Propargyl alcohol type quaternary ammonium salt surfactant and preparation method thereof |
| CN102049213B (en) * | 2010-11-12 | 2013-06-19 | 西华师范大学 | Propargyl alcohol type quaternary ammonium salt surfactant and preparation method thereof |
| CN104630784A (en) * | 2015-02-09 | 2015-05-20 | 西安华诺石油技术开发有限公司 | Anti-carbon dioxide corrosion inhibitor and preparation method thereof |
| CN106083613A (en) * | 2016-06-17 | 2016-11-09 | 华中科技大学 | A kind of alkynol class Mannich base corrosion inhibiter and synthetic method thereof and application |
| CN106083613B (en) * | 2016-06-17 | 2018-07-03 | 华中科技大学 | A kind of alkynol class Mannich base corrosion inhibiter and its synthetic method and application |
| CN108300452A (en) * | 2018-02-27 | 2018-07-20 | 山东科瑞油田服务集团股份有限公司 | A kind of acid solution multipurpose additive and preparation method thereof |
| CN109355666A (en) * | 2018-06-05 | 2019-02-19 | 天津市职业大学 | A kind of carbon steel pickling corrosion inhibitor and its preparation method and application |
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|---|---|
| CN1086381C (en) | 2002-06-19 |
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