• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
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    • 专利摘要:
    Neue Bisimidazoline der Formel wobei R das Alkylgerüst einer dimerisierten Fettsäure mit 22 bis 42, vorzugsweise 34 C-Atomen, X ein Sauerstoffatom oder eine Gruppe der Formel N-Bm, B Wasserstoff, Methyl, Ethyl, Benzyl oder eine Gruppe der Formel -(CH2CHYO)n-R1, Y Wasserstoff, Methyl oder Ethyl, R1 Wasserstoff oder eine Gruppe -COR2 R2 C1-C22-, vorzugsweise C8-C22-Alkyl, a 0 oder 1, b eine Zahl von 0 bis 4, m 1 oder 2, n eine Zahl von 0 bis 100, vorzugsweise 0 bis 20, i eine Zahl von 0 bis 2b + 2 und A ein Anion bedeutet, Verfahren zu deren Herstellung und deren Verwendung als Erdölemulsionsspalter.
    公开号:SU1199200A3
    申请号:SU823486422
    申请日:1982-09-03
    公开日:1985-12-15
    发明作者:Ричель Вернер；Дьери Хельмут；Хилле Мартин
    申请人:Хехст А.Г. (Фирма)；
    IPC主号:
    专利说明:

    This invention relates to a process for the preparation of new imidazline derivatives, namely, bisimidazolines of the general formula V. Jl- (C2HnX)) njRi NyR N-lC HfjiOr CH CHYOVjCOR N- / where R is an alkyl structure of dimerized fatty acids with 34 carbon atoms; 0.1; - H or CH or the oxygen atom group NCH; or - (CH2CHyo) -Ri; H or -COR - ff-alkyl Cg-C, 7 n, - numbers from O to 2, 2; 4; A CE CHjCOO Sp f with anti-emulsifying and ant-corrosive properties. The purpose of the invention is to obtain new compounds with valuable properties. The proposed method illustrates. with the following examples. Example 1. In a water separator, 0.5 mol of dimeric ® r-H3C-N; N-CH2R © and CH3-NN-CH2 are located, where R (here and in the following alkyl forms there is a structure with 34 carbon atoms of dienerized fatty acid Molecular weight 1299, X-ray 1610 with and 1740 cm. Calculated, Z: C 73.97; H 11.64, N6, 46. Found:%: 73.1; H 12.0; N 6.8; CE 4.6. CH2-C R. L HN M-CH2-C 002 fatty acid with 1 mol of amine in 30-150 ° C with reverse of 300 g of xylene with an inlet stream until about 36 ml of water is obtained. After distillation of xylene, a viscous product is obtained. Bisimidazolines IVa-IVc were made, respectively: from 285 g (0.5 mol) Pripol 1 022 and 105 g (1 mol) of diethylenetriamine; from 285 g (0.5 mol) of Pripol 1022 and 104 g (1 mol) of aminostillethanolamine; from 285 g (0.5 mol) of Pripol 1010 and 103 g (1 mol) dystilenetriamine. Bisimidazolines IVa-IVc exhibit an infrared spectrum characteristic C absorption line at 1610 cm. Example 2. 250 g (1 mol) of stearic acid is added to a solution prepared according to the general indication of bimimidazoline IVa in 300 g of xylene. 150 seconds with reverse flow. Heating is continued until 18 ml of water is dispensed. After the separation of xylene, 650 g of isobutanol are added and the mixture is quaternized in an autoclave at 70 ° C with methyl chloride. A brown pouring liquid is obtained containing 50% of a compound of the formula N-CO (CH7) iBCH3 and 2C1 I -CO (CH2libCH3 Example 3) After conversion of bimidazoline IVa with 250 g of stearyiic acid, as in Example 1, is performed, 60 g are added ( 1 mole) of acetic acid. After the separation of xylene and the addition of 650 g of isobutanol, a solution containing 50% of the compound of the formula —CO (CHr,) is CH3 2CH3Co6 H — CO (Molecular weight 1319, X-1610 erf and 1740 is calculated. Calculated: C 7.4.7; H 11.8; N 6.4., Found: C 75.2; H 11.1; N 6.7. Example 4. To the solution of imidazoline IVa in 300 xylene was added 125 g ( 0.5 mol) of stearic NZC lL -CH2-CH7 ) M H 6Molekul weight 1062.5; IR 1610 and 1740.
    Calculated,%: C, 72.3; H 11.2; N 5.3; C1 6.7 „
    . Found,%: C 71.9; H 10.9; N 5.5; ce 5.0.
    Example 5 In a bi-imidazoline IVJ in an autoclave, after the introduction of 1.3 g of powdered sodium hydroxide is added at 160 ° C and 15 bar.
    g-
    NZS-li K-CH CH2CISN.1CHN.0) p17CO (
    R
    © A T4 N-CHoTfN-CH-CH20-1CH., SNg, 0) pgN
    n, +
    Molecular weight 1512; 2 ZhS 1610 cm- and 1740.
    Calculated,%: C 66.7; H 11.2; N 3.7; Cf 4.7.
    Found,%: C 67.2, H 11.9; N 4.0; cf 4.2.
    Example 6, Bisimidazolinium 1Uv, known in an autoclave at 150 ° C AS
    НЗС-тО СНтр-1СНгСН20) pg About SVD1bSNz
    ®
    НСС-1 -СН -СНгр- (СНгСН20) pg-CO (cNg) 1b СНз
    P,
    Molecular weight 2648.7; IKS 1610 and 1740.
    Calculated,%: C 64.4; H 10.3; N 2.1; Ct 2.7.
    Found,%: C 64.5; H 10.5; N 2.4; Cf 1.9. CH-iCH OH
    220 g (5 mol) of ethylene oxide Then 125 g (0.5 mol) of stearic acid are added. The composition is kept in distillation apparatus at 160 ° C before 9 ml of water is distilled off. After the addition of 730 g of isobutanol, the composition is quaternized in an autoclave at 70 ° C with methyl chloride. A 50% solution in isotane is obtained of a compound of the formula
    2С1
    and 4–5 bars of 660 g (15 mol) of ethylene oxide are added. Then 250 g (1 mol) of stearic acid are added and 18 ml of water are distilled off in distillation apparatus at 160-180 ° C. After the addition of 1300 g of isobutanol, it is quaternized at 60-70 C with methylene chloride. The resulting solution sogs1
    Example 7. Bisimidazoline in the usual way under pressure of 5 bar is introduced first 220 g (5 mol) of ethylene oxide at 150 ° C, and then 280 g (5 mol) of propylene oxide at 160 ° C and the subtophes of the same pressure. Then, 380 rfl, 5 moles of fatty acids of fat are added. The acid is kept at 130-150 ° C with reverse flow and 5 ml of water are removed from the water separator. After the separation of xylene, 570 g of isobutanol are added and the reaction is carried out in an autoclave at 70 ° C with chloride of metal to stop its consumption for the reaction. A 50% solution in Isobutanol of the compound of the formula O is obtained (CH2.1iBCH3, 2C1 holds 50% of the compound according to the formula: The composition is taken out of the caulking apparatus, and doused up. 27 ml of water will be distilled. Then 1200 gisobutanol ipo (CH2CH2-CH2N
    СНг-СН М- (СН2СН20) pg-СН2СНО), 2-СОВ
    .СНз
    (CH2-CH20) n2- (FUTURE bHH where R2 is fatty acid alkyl fat, 2 (n, + P2) 10, 2 (t, -Nn2) 10 p hectares., T2 2.54, molecular weight 2501.8 IRS 1610 cm- and 1740 cm. Calculated,%: C 71.1 H 10.9; N 3.4. C 70.9; H n, l; N 3.7, Found, Kj4-CH2C % NN-CH3CH H where R is fatty acid alkyl fat 2 {n, + P2) 5 1.2 5. Molecular weight 1882.5J X 1610 cm- and 1740. Calculated,%: 080.4; H 7.5, N 5 Found,%: C 80.9; H 7.8; N 4, Example 9. 420 g (0.5 mol of dimeric fatty acid Fatty Lot 7002 is heated with 104 g F / CHo-N NY K F Js. C where R is 2-ethylhexyl. Molecular weight 961.5; IKS 1610 cm- and 1740. Calculated,%: C 68.7; H 10.5; N 5.8; Ct 3,3. Found,%: C 69.2; H 9, 9; N 6.2; C1 3.1. Example 10. To bisimidazoline IVB after the addition of 1.5 g of porous shN
    CH20) pg (CH2-CHO) mi- COH. A brown pouring liquid containing 50% of the active substance is obtained using the following formula: Example 8 To bisimidazoline IVa in the usual way add PO (g) (2.5 mol) to ethylene oxide. Then, at 160-180 s, 500 g (2 mol) of fatty acid is produced in fat. After the addition of 925 g of iso-butanol, a 50% solution of the compound of the formula 2CHaO) ni-CX) Ri) nuCOKi 2 (1 mol) with ethioethylethanolamine without solvent is obtained, until 36 ml of water is distilled off. Then 72 g (0.5 mol) of 2-ethylhexanoic acid are added and another 9 ml of water are distilled off. After the introduction of 630 g of isobutanol, it is bacterized with 80 g of dimethyl sulfate from 65 C. As a result, a 50% solution in isobutanol is obtained of a compound of the following formula CH20COK | CH380 / 1 CH20H shaped NaOH was added 880 g (20 mol) of ethylene oxide at 150 ° C and 5 bar. Then 250 g (1 mol) of stearic acid are added and pressurized until until 18 mp are distilled off. Then, in an autoclave, it is injected at 70 C CH, CE to the extent of absorption. J 1550 g of compound are obtained
    F / -
    3 / CWi-W2-0 - () rfrC- (CH) l6-CH3
    СНгСН -0- (СНг-СН2-0) pg-С- (СН2) 1B-СНз
    x 1610), 1730 cm () o
    Calculated,%: C 62.5; H 10.4; N 1.8; From 2.3.
    Found,%: C 61.8; H 10.9; N 1.7; Ct 1.9.
    Tables 1–4 show the anti-emulsifying effect of the compounds according to the invention on oil emulsions in conventional oil fields.
    Emulsifiers are used in 50% isobutanol solutions injected with microdissection equipment. The separation of emulsified water occurs in closed conical calibrated beakers with chemical stoppers. The amount of emulsion is in each case 100 cm.
    The absolute water content of the emulsion is determined in each case.
    ABOUT
    2С1
    , 0
    I p, 20; p, 20 preliminary experiments on DinStar.
    Inhibition of corrosion. To define By dividing the corrosion inhibition effect, experienced carbon steel strips with a surface of 20 cm were immersed for 6 hours at 60 ° C in a 20% solution of sodium chloride containing an additive of 10 mg / l, 20 mg / l, or 30 mg / l of the test product. During the test, a continuous stream of carbon dioxide bubbles was passed through the test solution. The measure of corrosivity is then the absolute weight loss of the metal strip that is established.
    The results obtained are summarized in table 5.
    Thus, the products used according to the invention have the properties of a good splitter and at the same time a corrosion inhibitor.
    Table i
    Note: De-emulsification temperature: water content of the emulsion is 43%, the dosage amount is 40 ppm; the origin of Neuti is the North Sea.
    21233
    32154
    42562
    51748
    61638
    72454
    82048
    92243 Supplements, Note,
    2 3 4 5
    40
    15
    85 78 85 85 90 88 88 79 O.
    18
    36
    42
    15
    42
    P 6 7 8 9
    51
    ten
    47
    12
    53
    eight
    40
    14
    100
    No additives About Note.
    table 2
    78
    93
    96,100
    100 100
    98,100
    98
    92
    98,100
    94,100
    91
    97 O
    ABOUT
    4 6 3
    93 90 98 98
    1.0
    98
    1.0 3.5
    96
    2.0 1.0
    100
    ABOUT
    2.5 0.3
    100
    About 1.0
    100 99 o
    100
    About 2.0
    0.2
    100
    ABOUT
    100 94 1.5 O
    100
    about 5 100
    1.5
    98
    1.5 .0 100
    About 100 Temperature of demulsification 40 ° C; water retention 65%; dosing amount of 50 ppm; iefty origin UK, demulsification temperature 52 ° C; water content. 20%, dosing amount 60 h / ml; the origin of the oil is Borneo; I - interfacial c.i sludge material; W - water separation. T a b l itz a 3 W2 I T 7 1 I L.) L 180 min
    1 Note.
    Table 5
    12
    1 199200 Table 4
    Continued Ta6h.5. Demulsification temperature 48 ° C; water content 19%; dosing amount of 50 ppm; the origin of the oil is Nigeria.
    权利要求:
    Claims (1)
    [1]
    (54) (57) METHOD FOR PRODUCING BISIMIDAZOLINE of general formula (1) ’1
    R 'B ( f : l {jHC ^ i4Kl 6 “(CH 2 CHYO) n / X) R2. X .
    where R is the alkyl structure of a dimerized fatty acid with 34 carbon atoms;
    Ba is H or s e , <) = 0.1; X is an oxygen atom or a group ^ NB;
    B is H, CH, or - (CH 2 CH UO) - R ,; y-H, CH 3 ; R, -H or -COR Z ; R 2 -H-alkyl Cd-C ^;
    B = 1; n ( , n 2 - numbers from 0 to 20; i = 0, 2,4; A - CE, CH 3 COO ~, ch so;, characterized in that the dimerized fatty acid of the formula (P)
    HOOC-R-COOH where R is as defined above, is reacted with a di- or polyamine of formula (w) h 2 n-ch 2 -ch 2 -nh- (CH 2 -CHx) 6 H to give a bisimidazoline of formula (IV)
    N
    RN ^ N-iCaH ^ H where R, x, b is indicated above and the obtained bisimidazoline is reacted with ethylene oxide or first with ethylene- and then with propylene oxide, the resulting product is esterified with an acid of the general formula R 2 -COOH, where R 2 has the indicated meaning, Quaternize or neutralize and isolate the target product.
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    引用文献:
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    US3246008A|1961-10-03|1966-04-12|Skelly Oil Co|Reaction products of ozonized fatty acids and alkylene polyamines|
    FR1412921A|1963-12-18|1965-10-01|New amphoteric imidazoline compounds|
    DE2210087B2|1972-03-02|1980-11-27|Hoechst Ag, 6000 Frankfurt|Imidazolinium salts and fabric softeners containing them|
    DE2930849A1|1979-07-30|1981-02-26|Henkel Kgaa|NEW N-HYDROXYALKYLIMIDAZOLINE DERIVATIVES, THEIR PRODUCTION AND USE|
    US4292046A|1979-08-10|1981-09-29|Mobil Oil Corporation|Detergent compositions|JPH0367233B2|1984-04-26|1991-10-22|Mitsubishi Electric Corp|
    CN104411805A|2012-05-25|2015-03-11|巴斯夫欧洲公司|Use of a reaction product of carboxylic acids with aliphatic polyamines for improving or boosting the separation of water from fuel oils|
    US9039791B2|2012-05-25|2015-05-26|Basf Se|Use of a reaction product of carboxylic acids with aliphatic polyamines for improving or boosting the separation of water from fuel oils|
    IN2013CH06134A|2013-12-27|2015-07-03|Dow Global Technologies Llc|
    CN105829579A|2013-12-27|2016-08-03|陶氏环球技术有限责任公司|Bis-imidazoline compounds as corrosion inhibitors and preparation thereof|
    IN2013CH06132A|2013-12-27|2015-07-03|Dow Global Technologies Llc|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19813135235|DE3135235A1|1981-09-05|1981-09-05|BISIMIDAZOLINES, METHOD FOR THE PRODUCTION AND USE THEREOF|
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